…

Sear

Aniline

Aniline is an organic compound with the

formula C6H5NH2. Consisting of a phenyl
group attached to an amino group, aniline
is the simplest aromatic amine. Its main
use is in the manufacture of precursors to
polyurethane and other industrial
chemicals. Like most volatile amines, it
has the odor of rotten fish. It ignites
readily, burning with a smoky flame
characteristic of aromatic compounds.[6]
 Aniline

Names

Preferred IUPAC name

Aniline[1]
Systematic IUPAC name
Benzenamine
Other names
 Phenylamine
Aminobenzene
Identifiers
Benzamine
CAS Number 62-53-3  

142-04-1 (HCl) 
3D model (JSmol) Interactive image
Interactive image

3DMet B00082
Beilstein Reference 605631

ChEBI CHEBI:17296  

ChEMBL ChEMBL538  

ChemSpider 5889  
DrugBank DB06728  
ECHA InfoCard 100.000.491

EC Number 200-539-3
Gmelin Reference 2796

KEGG C00292  

PubChem CID 6115

8870  (HCl)

RTECS number BW6650000

UNII SIR7XX2F1K  

UN number 1547
CompTox Dashboard DTXSID8020090
(EPA)
InChI
InChI=1S /C6H7N/c 7-6-4-2-1-3-5-6/h1-5H,7H2 
Key: PAYRUJLWNCNPS J-UHFFFAOYS A-N 

InChI=1/C6H7N/c 7-6-4-2-1-3-5-6/h1-5H,7H2

SMILES Key: PAYRUJLWNCNPS J-UHFFFAOYAP

Nc 1c c c c c 1
c 1c c c (c c 1)N

Properties
Chemical formula C6H7N

Molar mass 93.129 g·mol−1

Appearance Colorless to yellow

liquid

Density 1.0297 g/mL

Melting point −6.3 °C (20.7 °F;

266.8 K)

Boiling point 184.13 °C (363.43 °F;

 457.28 K)
Solubility in water 3.6 g/100 mL at 20 °C

Vapor pressure 0.6 mmHg (20° C)[2]

Acidity (pKa) 4.87 (conjugate acid;

H2O)[3]
Magnetic −62.95·10−6 cm3/mol
susceptibility (χ)
Viscosity 3.71 cP (3.71 mPa·s
at 25 °C)

Thermochemistry
Std enthalpy of −3394 kJ/mol
combustion
(ΔcH⦵298)
Hazards
Main hazards potential occupational
carcinogen

Safety data sheet See: data page

GHS pictograms

GHS Signal word Danger

GHS hazard H301, H311, H317,
statements
H318, H331, H341,
H351, H372, H400
GHS precautionary P201, P202, P260,
statements
P261, P264, P270,
P271, P272, P273,
P280, P281,
P301+310, P302+352,
 P304+340,
P305+351+338,
P308+313, P310,
P311, P312, P314,
P321, P322, P330,
P333+313, P361

NFPA 704 2 [5]

3 0
(fire diamond)

Flash point 70 °C (158 °F; 343 K)

Autoignition 770 °C (1,420 °F;
temperature
1,040 K)

Explosive limits 1.3–11%[2]

Lethal dose or concentration (LD, LC):

 LDLo (lowest 195 mg/kg (dog, oral)
published) 250 mg/kg (rat, oral)
464 mg/kg (mouse,
oral)
440 mg/kg (rat, oral)
400 mg/kg (guinea
pig, oral)[4]
LC50 (median 175 ppm (mouse, 7
concentration) h)[4]
LCLo (lowest 250 ppm (rat, 4 h)
published) 180 ppm (cat, 8 h)[4]

NIOSH (US health exposure limits):

PEL (Permissible) TWA 5 ppm (19
 mg/m3) [skin][2]
REL (Recommended) Ca [potential
occupational
carcinogen][2]
IDLH (Immediate 100 ppm[2]
danger)
Related compounds
Related aromatic 1-Naphthylamine
amines
2-Naphthylamine
Related compounds Phenylhydrazine
Nitrosobenzene
Nitrobenzene

Supplementary data page

Structure and Refractive index (n),
properties Dielectric constant
(εr), etc.
Thermodynamic Phase behaviour
data
solid–liquid–gas
Spectral data UV, IR, NMR, MS
Except where otherwise noted, data are given
for materials in their standard state (at 25 °C
[77 °F], 100 kPa).

 verify (what is   ?)

Infobox references

Structure
Aniline is a slightly pyramidalized
molecule, with hybridization of the nitrogen
somewhere between sp3 and sp2. The
amine is flatter than an aliphatic amine,
owing to conjugation of the lone pair with
the aryl substituent. Thus, the experimental
geometry reflects a balance between the
stabilization of lone pairs in orbitals with
higher s character and better stabilization
via conjugation with the aryl ring for an
orbital of pure p character. The
pyramidalization angle between the C–N
bond and the bisector of the H–N–H angle
is 142.5°.[7] (For comparison, in more
strongly pyramidal methylamine, this value
is ~125°, while a planar nitrogen like that
of formamide has an angle of 180°.) The
C−N distance is correspondingly shorter.
In aniline, the C−N and C−C distances are
close to 1.39 Å, indicating the π-bonding
between N and C.[8]

Production
Industrial aniline production involves two
steps. First, benzene is nitrated with a
concentrated mixture of nitric acid and
sulfuric acid at 50 to 60 °C to yield
nitrobenzene. The nitrobenzene is then
hydrogenated (typically at 200–300 °C) in
the presence of metal catalysts:[9]

The reduction of nitrobenzene to aniline

was first performed by Nikolay Zinin in
1842, using inorganic sulfide as a
reductant (Zinin reaction). The reduction of
nitrobenzene to aniline was also
performed as part of reductions by
Antoine Béchamp in 1854, using iron as the
reductant (Bechamp reduction).

Aniline can alternatively be prepared from

ammonia and phenol derived from the
cumene process.[6]

In commerce, three brands of aniline are

distinguished: aniline oil for blue, which is
pure aniline; aniline oil for red, a mixture of
equimolecular quantities of aniline and
ortho- and para-toluidines; and aniline oil
for safranine, which contains aniline and
ortho-toluidine and is obtained from the
distillate (échappés) of the fuchsine
fusion.[10]

Related aniline derivatives …

Many analogues of aniline are known

where the phenyl group is further
substituted. These include toluidines,
xylidines, chloroanilines, aminobenzoic
acids, nitroanilines, and many others. They
often are prepared by nitration of the
substituted aromatic compounds followed
by reduction. For example, this approach is
used to convert toluene into toluidines and
chlorobenzene into 4-chloroaniline.[6]
Alternatively, using Buchwald-Hartwig
coupling or Ullmann reaction approaches,
aryl halides can be aminated with aqueous
or gaseous ammonia [11]

Reactions
The chemistry of aniline is rich because
the compound has been cheaply available
for many years. Below are some classes
of its reactions.

Oxidation …

The oxidation of aniline has been heavily

investigated, and can result in reactions
localized at nitrogen or more commonly
results in the formation of new C-N bonds.
In alkaline solution, azobenzene results,
whereas arsenic acid produces the violet-
coloring matter violaniline. Chromic acid
converts it into quinone, whereas
chlorates, in the presence of certain
metallic salts (especially of vanadium),
give aniline black. Hydrochloric acid and
potassium chlorate give chloranil.
Potassium permanganate in neutral
solution oxidizes it to nitrobenzene; in
alkaline solution to azobenzene, ammonia,
and oxalic acid; in acid solution to aniline
black. Hypochlorous acid gives 4-
aminophenol and para-amino
diphenylamine.[10] Oxidation with
persulfate affords a variety of polyanilines
compounds. These polymers exhibit rich
redox and acid-base properties.

Polyanilines can form upon oxidation of aniline.

Electrophilic reactions at carbon …

Like phenols, aniline derivatives are highly

susceptible to electrophilic substitution
reactions. Its high reactivity reflects that it
is an enamine, which enhances the
electron-donating ability of the ring. For
example, reaction of aniline with sulfuric
acid at 180 °C produces sulfanilic acid,
H2NC6H4SO3H.

If bromine water is added to aniline, the

bromine water is decolourised and a white
precipitate of 2,4,6-tribromoaniline is
formed. To generate the mono-substituted
product, a protection with acetyl chloride
is required:
Aniline can react with bromine even in room
temperatures in water. Acetyl chloride is added to
prevent tribromination.

The reaction to form 4-bromoaniline is to

protect the amine with acetyl chloride, then
hydrolyse back to reform aniline.
The largest scale industrial reaction of
aniline involves its alkylation with
formaldehyde. An idealized equation is
shown:

2 C6H5NH2 + CH2O → CH (C H NH )
2 6 4 2 2 +
H2O

The resulting diamine is the precursor to

4,4'-MDI and related diisocyanates.

Reactions at nitrogen …

Basicity …
Aniline is a weak base. Aromatic amines
such as aniline are, in general, much
weaker bases than aliphatic amines.
Aniline reacts with strong acids to form
anilinium (or phenylammonium) ion (C6H5-
NH3+).[12]

Traditionally, the weak basicity of aniline is

attributed to a combination of inductive
effect from the more electronegative sp2
carbon and resonance effects, as the lone
pair on the nitrogen is partially delocalized
into the pi system of the benzene ring. (see
the picture below):

The nitrogen's electron was delocalized to the ring.

This is why that aniline is less basic than most
amines.

Missing in such analysis is consideration

of solvation. Aniline is, for example, more
basic than ammonia in the gas phase, but
ten thousand times less so in aqueous
solution.[13]

Acylation …

Aniline reacts with acyl chlorides such as

acetyl chloride to give amides. The amides
formed from aniline are sometimes called
anilides, for example CH3-CO-NH-C6H5 is
acetanilide. At high temperatures aniline
and carboxylic acids react to give the
anilides.[14]

N-Alkylation …
N-Methylation of aniline with methanol at
elevated temperatures over acid catalysts
gives N-methylaniline and dimethylaniline:

C6H5NH2 + 2 CH3OH → C H N(CH )

6 5 3 2 +
2H2O

N-Methylaniline and dimethylaniline are

colorless liquids with boiling points of
193–195 °C and 192 °C, respectively.
These derivatives are of importance in the
color industry. Aniline combines directly
with alkyl iodides to form secondary and
tertiary amines.[10]
Carbon disulfide derivatives …

Boiled with carbon disulfide, it gives

sulfocarbanilide (diphenylthiourea)
(CS(NHC6H5)2), which may be
decomposed into phenyl isothiocyanate
(C6H5CNS), and triphenyl guanidine
(C6H5N=C(NHC6H5)2).[10]

Diazotization …

Aniline and its ring-substituted derivatives

react with nitrous acid to form diazonium
salts. Through these intermediates, aniline
can be conveniently converted to -OH, -CN,
or a halide via Sandmeyer reactions. This
diazonium salt can also be reacted with
NaNO2 and phenol to produce a dye
known as benzeneazophenol, in a process
called coupling. The reaction of converting
primary aromatic amine into diazonium
salt is called diazotisation. In this reaction
primary aromatic amine reacts with
sodium nitrile and with 2 moles of HCl
which is known as Ice cold mixture
because the temperature use to be 0.5°C
and it forms benzene diazonium salt as
major product and water and sodium
chloride.

Other reactions …

It reacts with nitrobenzene to produce

phenazine in the Wohl-Aue reaction.
Hydrogenation gives cyclohexylamine.

Being a standard reagent in laboratories,

aniline is used for many niche reactions.
Its acetate is used in the aniline acetate
test for carbohydrates, identifying
pentoses by conversion to furfural. It is
used to stain neural RNA blue in the Nissl
stain.

Uses
The largest application of aniline is for the
preparation of methylenedianiline and
related compounds by condensation with
formaldehyde. The diamines are
condensed with phosgene to give
methylene diphenyl diisocyanate, a
precursor to urethane polymers.[6]
 Most aniline is consumed in the production of
methylenedianiline, a precursor to polyurethanes.

Other uses include rubber processing

chemicals (9%), herbicides (2%), and dyes
and pigments (2%).[15] As additives to
rubber, aniline derivatives such as
phenylenediamines and diphenylamine, are
antioxidants. Illustrative of the drugs
prepared from aniline is paracetamol
(acetaminophen, Tylenol). The principal
use of aniline in the dye industry is as a
precursor to indigo, the blue of blue
jeans.[6]

Cake of indigo dye, which is prepared from aniline.

Aniline is also used at a smaller scale in

the production of the intrinsically
conducting polymer polyaniline.

Some early American rockets, such as the

Aerobee and WAC Corporal, used a
mixture of aniline and furfuryl alcohol as a
fuel, with nitric acid as an oxidizer. The
combination is hypergolic, igniting on
contact between fuel and oxidizer. It is
also dense, and can be stored for
extended periods.

History
Aniline was first isolated in 1826 by Otto
Unverdorben by destructive distillation of
indigo.[16] He called it Crystallin. In 1834,
Friedlieb Runge isolated a substance from
coal tar that turned a beautiful blue color
when treated with chloride of lime. He
named it kyanol or cyanol.[17] In 1840, Carl
Julius Fritzsche (1808–1871) treated
indigo with caustic potash and obtained an
oil that he named aniline, after an indigo-
yielding plant, anil (Indigofera
suffruticosa).[18][19] In 1842, Nikolay
Nikolaevich Zinin reduced nitrobenzene
and obtained a base that he named
benzidam.[20] In 1843, August Wilhelm von
Hofmann showed that these were all the
same substance, known thereafter as
phenylamine or aniline.[21]

Synthetic dye industry …

In 1856, while trying to synthesise quinine,

von Hofmann's student William Henry
Perkin discovered mauveine and went into
industry producing the first commercial
synthetic dye. Other aniline dyes followed,
such as fuchsin, safranin, and induline. At
the time of mauveine's discovery, aniline
was expensive. Soon thereafter, applying a
method reported in 1854 by Antoine
Béchamp,[22] it was prepared "by the
ton".[23] The Béchamp reduction enabled
the evolution of a massive dye industry in
Germany. Today, the name of BASF,
originally Badische Anilin- und Soda-Fabrik
(English: Baden Aniline and Soda Factory),
now the largest chemical supplier, echoes
the legacy of the synthetic dye industry,
built via aniline dyes and extended via the
related azo dyes. The first azo dye was
aniline yellow.[24]

Developments in medicine …

In the late 19th century, derivatives of

aniline such as acetanilide and phenacetin
emerged as analgesic drugs, with their
cardiac-suppressive side effects often
countered with caffeine.[25] During the first
decade of the 20th century, while trying to
modify synthetic dyes to treat African
sleeping sickness, Paul Ehrlich – who had
coined the term chemotherapy for his
magic bullet approach to medicine – failed
and switched to modifying Béchamp's
atoxyl, the first organic arsenical drug, and
serendipitously obtained a treatment for
syphilis – salvarsan – the first successful
chemotherapy agent. Salvarsan's targeted
microorganism, not yet recognized as a
bacterium, was still thought to be a
parasite, and medical bacteriologists,
believing that bacteria were not
susceptible to the chemotherapeutic
approach, overlooked Alexander Fleming's
report in 1928 on the effects of
penicillin.[26]

In 1932, Bayer sought medical applications

of its dyes. Gerhard Domagk identified as
an antibacterial a red azo dye, introduced
in 1935 as the first antibacterial drug,
prontosil, soon found at Pasteur Institute
to be a prodrug degraded in vivo into
sulfanilamide – a colorless intermediate
for many, highly colorfast azo dyes –
already with an expired patent, synthesized
in 1908 in Vienna by the researcher Paul
Gelmo for his doctoral research.[26] By the
1940s, over 500 related sulfa drugs were
produced.[26] Medications in high demand
during World War II (1939–45), these first
miracle drugs, chemotherapy of wide
effectiveness, propelled the American
pharmaceutics industry.[27] In 1939, at
Oxford University, seeking an alternative to
sulfa drugs, Howard Florey developed
Fleming's penicillin into the first systemic
antibiotic drug, penicillin G. (Gramicidin,
developed by René Dubos at Rockefeller
Institute in 1939, was the first antibiotic,
yet its toxicity restricted it to topical use.)
After World War II, Cornelius P. Rhoads
introduced the chemotherapeutic
approach to cancer treatment.[28]

Rocket fuel …

In the 1940s and early 1950s, aniline was

used with nitric acid or dinitrogen tetroxide
as rocket fuel for small missiles and the
Aerobee rocket. The two fuel components
are hypergolic, producing a violent reaction
on contact. Aniline was later replaced by
hydrazine.[29]

Toxicology and testing

Aniline is toxic by inhalation of the vapour,
ingestion, or percutaneous
absorption.[30][31] The IARC lists it in Group
3 (not classifiable as to its carcinogenicity
to humans) due to the limited and
contradictory data available. The early
manufacture of aniline resulted in
increased incidents of bladder cancer, but
these effects are now attributed to
naphthylamines, not anilines.[6]

Aniline has been implicated as one

possible cause of forest dieback.[32]

Many methods exist for the detection of

aniline.[33]

See also
Toxic oil syndrome

Notes
1. Nomenclature of Organic Chemistry:
IUPAC Recommendations and
Preferred Names 2013 (Blue Book).
Cambridge: The Royal Society of
Chemistry. 2014. pp. 416, 668.
doi:10.1039/9781849733069-FP001 .
ISBN 978-0-85404-182-4. "Aniline, for
C6H5-NH2, is the only name for a
primary amine retained as a preferred
IUPAC name for which full substitution
is permitted on the ring and the
nitrogen atom. It is a Type 2a retained
name; for the rules of substitution see
 P-15.1.8.2. Substitution is limited to
substituent groups cited as prefixes in
accordance with the seniority of
functional groups explicitly expressed
or implied in the functional parent
compound name. The name
benzenamine may be used in general
nomenclature."
2. NIOSH Pocket Guide to Chemical
Hazards. "#0033" . National Institute
for Occupational Safety and Health
(NIOSH).
3. Haynes, William M., ed. (2016). CRC
Handbook of Chemistry and Physics
(97th ed.). CRC Press. p. 5–89.
ISBN 978-1498754286.
4. "Aniline" . Immediately Dangerous to
Life and Health Concentrations (IDLH).
National Institute for Occupational
Safety and Health (NIOSH).
5. GOV, NOAA Office of Response and
Restoration, US. "ANILINE | CAMEO
Chemicals | NOAA" .
cameochemicals.noaa.gov. Retrieved
2016-06-16.
6. Thomas Kahl, Kai-Wilfrid Schröder, F.
R. Lawrence, W. J. Marshall, Hartmut
Höke, Rudolf Jäckh "Aniline" in
Ullmann's Encyclopedia of Industrial
Chemistry, 2007. John Wiley & Sons:
New
York.doi:10.1002/14356007.a02_303
7. 1937-, Carey, Francis A. (2008).
Organic chemistry (7th ed.). Boston:
McGraw-Hill Higher Education.
ISBN 9780073047874.
OCLC 71790138 .
 8. G. M. Wójcik "Structural Chemistry of
Anilines" in Anilines (Patai's Chemistry
of Functional Groups), S. Patai, Ed.
2007, Wiley-VCH, Weinheim.
doi:10.1002/9780470682531.pat038
5.
9. Caskey, Douglas C.; Chapman,
Douglas W. (Apr 24, 1985), Process for
the preparation of
arylhydroxylamines , retrieved
2016-06-16
10. Chisholm 1911, p. 48.
11. https://www.organic-
chemistry.org/synthesis/C1N/amines/
anilines.shtm
12. McMurry, John E. (1992), Organic
Chemistry (3rd ed.), Belmont:
Wadsworth, ISBN 0-534-16218-5
13. Smith, Michael B.; March, Jerry (2007),
Advanced Organic Chemistry:
Reactions, Mechanisms, and
Structure (6th ed.), New York: Wiley-
Interscience, ISBN 978-0-471-72091-1
14. Carl N. Webb (1941). "Benzanilide" .
Organic Syntheses.; Collective Volume,
1, p. 82
15. "Aniline" . The Chemical Market
Reporter. Archived from the original
on 2002-02-19. Retrieved 2007-12-21.
16. Otto Unverdorben (1826). "Ueber das
Verhalten der organischen Körper in
höheren Temperaturen" [On the
behaviour of organic substances at
high temperatures]. Annalen der
Physik und Chemie. 8 (11): 397–410.
 Bibcode:1826AnP....84..397U .
doi:10.1002/andp.18260841109 .
17. F. F. Runge (1834) "Ueber einige
Produkte der Steinkohlendestillation"
(On some products of coal distillation),
Annalen der Physik und Chemie, 31:
65–77 (see page 65), 513–524 ; and
32: 308–332 (see page 331).
18. J. Fritzsche (1840) "Ueber das Anilin,
ein neues Zersetzungsproduct des
Indigo" (On aniline, a new
decomposition product of indigo),
Bulletin Scientifique [publié par
l'Académie Impériale des Sciences de
Saint-Petersbourg], 7 (12): 161–165.
Reprinted in:
J. Fritzsche (1840) "Ueber das
Anilin, ein neues
Zersetzungsproduct des Indigo,"
Justus Liebigs Annalen der
Chemie, 36 (1): 84–90.
J. Fritzsche (1840) "Ueber das
Anilin, ein neues
Zersetzungsproduct des Indigo" ,
Journal für praktische Chemie,
20: 453–457. In a postscript to
 this article, Erdmann (one of the
journal's editors) argues that
aniline and the "cristallin", which
was found by Unverdorben in
1826, are the same substance;
see pages 457–459 .
19. synonym I anil , ultimately from
Sanskrit "nīla", dark-blue.
20. N. Zinin (1842). "Beschreibung einiger
neuer organischer Basen, dargestellt
durch die Einwirkung des
Schwefelwasserstoffes auf
Verbindungen der Kohlenwasserstoffe
mit Untersalpetersäure" (Description
of some new organic bases, produced
by the action of hydrogen sulfide on
compounds of hydrocarbons and
hyponitric acid [H2N2O3]), Bulletin
Scientifique [publié par l'Académie
Impériale des Sciences de Saint-
Petersbourg], 10 (18): 272–285.
Reprinted in: N. Zinin (1842)
"Beschreibung einiger neuer
organischer Basen, dargestellt durch
die Einwirkung des
Schwefelwasserstoffes auf
Verbindungen der Kohlenwasserstoffe
mit Untersalpetersäure," Journal für
praktische Chemie, 27 (1): 140–153.
Benzidam is named on page 150.
Fritzsche, Zinin's colleague, soon
recognized that "benzidam" was
actually aniline. See: Fritzsche (1842)
Bulletin Scientifique, 10: 352.
Reprinted as a postscript to Zinin's
article in: J. Fritzsche (1842)
"Bemerkung zu vorstehender
Abhandlung des Hrn. Zinin"
(Comment on the preceding article by
 Mr. Zinin), Journal für praktische
Chemie, 27 (1): 153.
See also: (Anon.) (1842) "Organische
Salzbasen, aus Nitronaphtalose und
Nitrobenzid mittelst
Schwefelwasserstoff entstehend"
(Organic bases originating from
nitronaphthalene and nitrobenzene via
hydrogen sulfide), Annalen der Chemie
und Pharmacie, 44: 283–287.
21. August Wilhelm Hofmann (1843)
"Chemische Untersuchung der
organischen Basen im Steinkohlen-
 Theeröl" (Chemical investigation of
organic bases in coal tar oil), Annalen
der Chemie und Pharmacie, 47: 37–
87. On page 48, Hofmann argues that
krystallin, kyanol, benzidam, and
aniline are identical.
22. A. Béchamp (1854) "De l'action des
protosels de fer sur la nitronaphtaline
et la nitrobenzine. Nouvelle méthode
de formation des bases organiques
artificielles de Zinin" (On the action of
iron protosalts on nitronaphthaline and
nitrobenzene. New method of forming
Zinin's synthetic organic bases.),
Annales de Chemie et de Physique,
3rd series, 42: 186 – 196. (Note: In the
case of a metal having two or more
distinct oxides (e.g., iron), a "protosalt"
is an obsolete term for a salt that is
obtained from the oxide containing the
lowest proportion of oxygen to metal;
e.g., in the case of iron, which has two
oxides – iron (II) oxide (FeO) and iron
(III) oxide (Fe2O3) – FeO is the
"protoxide" from which protosalts can
be made. See: Wiktionary: protosalt.)
23. Perkin, William Henry. 1861-06-08.
"Proceedings of Chemical Societies:
Chemical Society, Thursday, May 16,
1861." The Chemical News and
Journal of Industrial Science.
Retrieved on 2007-09-24.
24. Auerbach G, "Azo and naphthol dyes",
Textile Colorist, 1880 May;2(17):137-9,
p 138 .
25. Wilcox RW, "The treatment of influenza
in adults", Medical News, 1900 Dec
15;77():931-2, p 932 .
26. D J Th Wagener, The History of
Oncology (Houten: Springer, 2009), pp
150–1 .
27. John E Lesch, The First Miracle Drugs:
How the Sulfa Drugs Transformed
Medicine (New York: Oxford University
Press, 2007), pp 202–3 .
28. "Medicine: Spoils of war" , Time, 15
May 1950.
29. Brian Burnell. 2016.
http://www.nuclear-
weapons.info/cde.htm#Corporal SSM
30. Muir, GD (ed.) 1971, Hazards in the
Chemical Laboratory, The Royal
Institute of Chemistry, London.
31. The Merck Index. 10th ed. (1983),
p.96, Rahway: Merck & Co.
32. Krahl-Urban, B., Papke, H.E., Peters, K.
(1988) Forest Decline: Cause-Effect
Research in the United States of North
America and Federal Republic of
Germany. Germany: Assessment
Group for Biology, Ecology and Energy
of the Julich Nuclear Research Center.
33. Basic Analytical Toxicology (1995), R.
J. Flanagan, S. S. Brown, F. A. de Wolff,
R. A. Braithwaite, B. Widdop: World
Health Organization

References
 This article incorporates text from a
publication now in the public
domain: Chisholm, Hugh, ed. (1911),
"Aniline", Encyclopædia Britannica, 2
(11th ed.), Cambridge University Press,
pp. 47–48

External links
Look up aniline in Wiktionary, the free
dictionary.

Wikimedia Commons has media

related to Aniline.

 Baynes, T.S., ed. (1878), "Aniline"  ,

Encyclopædia Britannica, 2 (9th ed.),
New York: Charles Scribner's Sons,
pp. 47–48 short=x
International Chemical Safety Card
0011
 CDC - NIOSH Pocket Guide to Chemical
Hazrds
Aniline electropolymerisation
Aniline in the ChemIDplus database

Retrieved from
"https://en.wikipedia.org/w/index.php?
title=Aniline&oldid=936067618"

Last edited 2 days ago by Leyo

Content is available under CC BY-SA 3.0 unless

otherwise noted.