AMITY INSTITUTE OF PHARMACY

SYNTHETIC REAGENTS AND APPLICATIONS

DIAZOMETHANE

Submitted To Presented by
Dr. Neerupma Dhiman Firuj Ahmed
Department of Pharmaceutical Chemistry Master of Pharmacy
1st Year
Index:
 1. Introduction
 2. Preparation
 3. Applications
 4. Reference
Synthetic Reagents:
Synthetic reagents consist of a broad range of chemicals with many
used in chemical synthesis.
They are the key components used for transforming functional group.
Diazomethane:
Diazomethane is the chemical compound CH2N2 discovered by
German chemist Sir Hans Von pechmann in 1894
Diazomethane is a yellow, poisonous, potentially, explosive
compound.
It is a gas at room temperature.

H 2C N N
IUPAC Name: Diazomethane
Other Name: Azimethylene, Azomethelene, Diazirine
Chemical Formula: CH2N2
Molar Mass: 42.04 gm/mol
Appearance: Yellow Gas
Odour: Musty
Solubility: Soluble in water

It is chemically very reactive and is, therefore, of

great value as synthetic reagent.
PREPARATION:
1.Pechmann’s method: By this method diazomethane is prepared from
methylamine by treating it with ethyl chlorofomate to form N-methyl
urethane.
This when treated with nitrous acid in ethereal solution yields N-methyl
N-nitrosourethane.
This on warming with alcoholic potassium hydroxide decompose into
diazomethane which is collect on cool ether.
HNO2
CH3NHCOOC2H5
CH3NH2 + ClCOOC2H5
NO

CH3 N COOC2H5

KOH

CH2N2+CO2+C2H5OH
2.Diazomethane is prepared by hydrolysis of an ethereal solution of an N
methyl nitrosamide with aqueous base:

O N CH2

S N NaOH
N

O
N

N-methyl-N-nitroso—p-toulenesulfonamide

N CH2
O N NH KOH
N
NO2
N

N-methyl-N-nitro-N-nitrosoguanidine
APPLICATIONS:
1.METHYLATION:
It is used as methylating agent for acidic compounds, alcohols, carbonyl
compounds, amines

CH2N2
RCOOH RCOOCH3
- N2
2. SYNTHESIS OF HETEROCYCLIC COMPOUNDS:
Diazomethane condense with ethylenic and acetylenic bonds to give
heterocyclic compounds

N N
CH2 UV Light
CH2 + N
+
CH2 N

Ethene Diazomethane Cyclopropane

REFERENCE:
1. Reaction and reagents by O.P.Agarwal, volume-1,USB
Publication,seventh edition (1995), page no.:840-844
2. Organic Chemistry by Robert Thornton Morrison, Robert Neilson Boyd,
Saibal Kanthi Bhattacharjee, Seventh Edition(2013), Published by Borling
Kinders Ley Pvt Ltd , Page no.: 331-334.
3. Text book of Organic Chemistry by I.L.Finar Volume 1,sixth
edition(1974),page no.392.
4. Textbook of Organic Reactions Reagents and Rearrangements by Sanyal,
published by Bharati Bhawan(2003),fourth edition,page no.:206-206.
THANK YOU