2-Naphthol

2-Naphthol, or β-naphthol, is a fluorescent colorless (or occasionally yellow) crystalline solid

with the formula C10H7OH. It is an isomer of 1-naphthol, differing by the location of the hydroxyl
group on the naphthalene ring. The naphthols are naphthalene homologues of phenol, but more
reactive. Both isomers are soluble in simple alcohols, ethers, and chloroform. 2-Naphthol is a
widely used intermediate for the production of dyes and other compounds.

Production
Traditionally, 2-naphthol is produced by a two-step process that begins with the sulfonation of
naphthalene in sulfuric acid:[2]

C10H8 + H2SO4 → C10H7SO3H + H2O

The sulfonic acid group is then cleaved in molten sodium hydroxide:

C10H7(SO3H) + 3 NaOH → C10H7ONa +

Na2SO3 + 2 H2O
Neutralization of the product with acid gives 2-naphthol.
2-Naphthol can also be produced by a method
analogous to the cumene process.[2]
2-Naphthol
2-Naphthol-
derived dyes
The Sudan dyes are popular dyes noted for
being soluble in organic solvents. Several of
the Sudan dyes are derived from 2-naphthol
by coupling with diazonium salts.[3] Sudan
dyes I–IV and Sudan Red G consist of arylazo-
substituted naphthols.

Selected 2-
Names
Naphthol-derived
Preferred IUPAC
dyes
name
Naphthalen-2-ol

Other names
2-
Hydroxynaphthale
ne; 2-
 Naphthalenol;
beta-Naphthol;
Naphth-2-ol

Identifiers

CAS 135-19-3
Sudan I Number
(https://c
ommonc
hemistry.
cas.org/
detail?ca
s_rn=135
-19-3)
Sudan II
3D Interactive
model
image (htt
(JSmol)
ps://chem
apps.stola
 f.edu/jmo
l/jmol.ph
p?model=
Oc2ccc1
c%28cccc
Sudan III 1%29c2)
Interactive
image (htt
ps://chem
apps.stola
f.edu/jmo
l/jmol.ph
Sudan IV p?model=
c1ccc2c
c%28ccc2
c1%29O)
 Beilstein 742134
Reference

ChEBI CHEBI:10432
(https://ww
w.ebi.ac.uk/c
Oil Red O hebi/searchI
d.do?chebiId
=10432)

ChEMBL ChEMBL14
26 (https://w
ww.ebi.ac.u
k/chembldb
Naphthol AS
index.php/c
mpound/ins
Reactions pect/ChEM
Some reactions of 2-naphthol are explicable
L14126)
with reference to its tautomerism, which
produces a small amount of the keto
tautomer. ChemSpi 8341 (htt
der ps://ww
Tautomeric equilibrium for beta-naphthol w.chems
One consequence of this tautomerism is the pider.co
Bucherer reaction, the ammonolysis of 2-
naphthol to give 2-aminonaphthalene. m/Chemi
2-Naphthol can be oxidatively coupled to form
BINOL, a C2-symmetric ligand popularized for
cal-Struc
use in asymmetric catalysis.
ture.834
1.html)

ECHA 100.004.71
InfoCard (https://ech
a.europa.e
u/substanc
-informatio
n/-/substan
ceinfo/100.
004.712)
EC 205-182-
Number 7

Gmelin 27395
Reference

KEGG C11713
(https://
www.keg
g.jp/entr
y/C1171
3)

PubChem 8663 (htt

CID
ps://pub
chem.nc
bi.nlm.ni
h.gov/co
mpound/
8663)
RTECS QL2975000
number

UNII P2Z71CIK5H
(https://prec
ision.fda.go
v/uniisearc
h/srs/unii/P
2Z71CIK5
H)

UN 3077
number

CompTox DTXSID502
Dashboard
061 (https:/
(EPA)
comptox.ep
a.gov/dash
oard/chem
 al/details/D
XSID50270
1)

InChI
InChI=1S/C10H8
O/c11-10-6-5-8
-3-1-2-4-9(8)7-1
0/h1-7,11H
Key: JWAZRIHNYR
IHIV-UHFFFAO
YSA-N
InChI=1/C10H8O/
c11-10-6-5-8-3-
1-2-4-9(8)7-10/
h1-7,11H
Key: JWAZRIHNYR
IHIV-UHFFFAO
YAV

SMILES
Oc2ccc1c(cccc1)
c2
 c1ccc2cc(ccc2c1)
O

Properties

Chemical C10H8O
formula

Molar 144.173 g·m

mass ol−1

Appeara Colorless
nce crystalline
solid

Density 1.280
g/cm3

Melting 121 to
point 123 °C
(250 to
253 °F;
 394 to
396 K)

Boiling 285 °C
point (545 °F;
558 K)

Solubility 0.74 g/L

in water

Acidity 9.51
(pKa)

Magnetic -98.25·10−6
susceptibility 3
cm /mol
(χ)

Hazards

Occupational safety
and health
(OHS/OSH):
 Main Harmful
hazards
when
inhaled or
swallowed
dangerous
to
environme
esp. aquat
organisms

GHS labelling:

Pictograms

Signal Warning
word

Hazard H302,
statements
H332,
H400
 Precautionary
P261, P26
statements
P270, P27
P273,
P301+P31
P304+P31
P304+P34
P312, P33
P391, P50

NFPA 2
1
0

704
(fire dia
mond)

Flash 161 °C
point (322 °F;
434 K)[1]
Except where
otherwise noted,
data are given for
materials in their
standard state (at
25 °C [77 °F],
100 kPa).
verify (https://en.w
ikipedia.org/w/inde
x.php?title=Special:
ComparePages&rev
1=477214746&page
2=2-Naphtho
l) (what is ?)
Infobox references
2-Naphthol converts to 2-naphthalenethiol by reaction with dimethylthiocarbamoyl chloride via
the Newman–Kwart rearrangement.[4] The OH→Br conversion has been described.[5]

Electrophilic attack occurs characteristically at the 1-position as indicated by nitrosylation to

give 1-nitroso-2-naphthol.[6] Bromination[7] and alkylations proceed with similar regiochemistry.[8]
Ring-opening reactions have been documented.[9]

Safety
2-Naphthol has been described as "moderately toxic.[2]

References

1. "MSDS safety data for 2-naphthol" (https://

web.archive.org/web/20110303133020/htt
ps://msds.chem.ox.ac.uk/NA/2-naphthol.ht
ml) . Archived from the original (https://ms
ds.chem.ox.ac.uk/NA/2-naphthol.html) on
3 March 2011.
2. Booth, Gerald (2005). "Naphthalene
Derivatives". Ullmann's Encyclopedia of
 Industrial Chemistry. Weinheim: Wiley-VCH.
doi:10.1002/14356007.a17_009 (https://do
i.org/10.1002%2F14356007.a17_009) .
ISBN 978-3527306732.. full-text PDF (http
s://pdfslide.net/documents/ullmanns-ency
clopedia-of-industrial-chemistry-naphthalen
e-derivatives.html)
3. Booth, Gerald; Zollinger, Heinrich; McLaren,
Keith; Sharples, William G.; Westwell, Alan
(2000). "Dyes, General Survey". Ullmann's
Encyclopedia of Industrial Chemistry. Wiley-
VCH. doi:10.1002/14356007.a09_073 (http
s://doi.org/10.1002%2F14356007.a09_07
3) . ISBN 9783527306732.
4. Melvin S. Newman; Frederick W. Hetzel
(1971). "Thiophenols from Phenols: 2-
Naphthalenethiol" (https://www.orgsyn.org/
 demo.aspx?prep=CV6P0824) . Organic
Syntheses. 51: 139.
doi:10.15227/orgsyn.051.0139 (https://doi.
org/10.15227%2Forgsyn.051.0139) .
5. J. P. Schaefer; Jerry Higgins; P. K. Shenoy
(1969). "2-Bromonaphthalene". Organic
Syntheses. 49: 6.
doi:10.15227/orgsyn.049.0006 (https://doi.
org/10.15227%2Forgsyn.049.0006) .
6. Marvel, C. S.; Porter, P. K. (1922). "Nitroso-β-
Naphthol". Organic Syntheses. 2: 61.
doi:10.15227/orgsyn.002.0061 (https://doi.
org/10.15227%2Forgsyn.002.0061) .
7. C. Frederick Koelsch (1940). "6-Bromo-2-
Naphthol". Organic Syntheses. 20: 18.
doi:10.15227/orgsyn.020.0018 (https://doi.
org/10.15227%2Forgsyn.020.0018) .
 8. Alfred Russell Luther B. Lockhart (1942). "2-
Hydroxy-1-Naphthaldehyde". Organic
Syntheses. 22: 63.
doi:10.15227/orgsyn.022.0063 (https://doi.
org/10.15227%2Forgsyn.022.0063) .
9. G. A. Page, D. S. Tarbell (1954). "β-(o-
Carboxyphenyl)propionic Acid". Organic
Syntheses. 34: 8.
doi:10.15227/orgsyn.034.0008 (https://doi.
org/10.15227%2Forgsyn.034.0008) .

External links

NIST Chemistry WebBook 2-

Naphthalenol (http://webbook.nist.gov/
cgi/cbook.cgi?Name=2-naphthol&Units=
SI)
 "Napthols" (https://en.wikisource.org/wi
ki/1911_Encyclop%C3%A6dia_Britannic
a/Napthols) . Encyclopædia Britannica.
Vol. 19 (11th ed.). 1911. pp. 168–169.

Retrieved from
"https://en.wikipedia.org/w/index.php?title=2-
Naphthol&oldid=1197756250"

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