Ethyl diazoacetate

Ethyl diazoacetate Basic information

Product Name:

Synonyms:

2-Diazoacetic acid ethyl;Diazoacetic acid ethyl;Ethyl diazoate;Acetic acid, 2-diazo-,ethyl ester;Ethyl diazoacetate contains >=13 wt. % dichloroMethane;Ethyl diazoacetate solution, 95%;2-Diazoacetic acid ethyl ester solution;Ethyl diazoacetate solution,90% wt in dichloromethane

CAS:

MF:

C4H6N2O2

MW:

114.1

EINECS:

210-810-8

Product Categories:

Azo/Diazo Compounds;Building Blocks;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks;Carboxylic;Azo/Diazo Compounds;Nitrogen Compounds;Organic Building Blocks

Mol File:

 

Ethyl diazoacetate Chemical Properties

Melting point 

−22 °C(lit.)

Boiling point 

140-141 °C720 mm Hg(lit.)

density 

1.085 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.46(lit.)

Fp 

115 °F

storage temp. 

2-8°C

Merck 

13,3021

BRN 

107654

NIST Chemistry Reference

 

Safety Information

Hazard Codes 

Risk Statements 

Safety Statements 

RIDADR 

UN 1993 3/PG 3

WGK Germany 

3

RTECS 

AG5775000

HazardClass 

3.2

PackingGroup 

III

HS Code 

29270000

MSDS Information

 

Ethyl diazoacetate Usage And Synthesis

Chemical Properties

Liquid.

Uses

Reagent for ruthenium-catalyzed asymmetric cyclopropanation of alkenes.1

Hazard

Flammable liquid that explodes when heated.

Safety Profile

Poison by ingestion and intravenous routes. Questionable carcinogen with experimental carcinogenic and tumorigenic data. Can explode. Explodes on contact with tris(dimethy1amino) antimony. When heated to decomposition it emits toxic fumes of NOx. See also ESTERS.

Purification Methods

It is a very volatile yellow oil with a strong pungent odour. EXPLOSIVE [distillation even under reduced pressure is dangerous and may result in an explosion — TAKE ALL THE NECESSARY PRECAUTIONS IF DISTILLATION IS TO BE CARRIED OUT]. It explodes in contact with conc H2SO4-trace acid causes rapid decomposition. It is slightly soluble in H2O, but is miscible with EtOH, *C6H6, pet ether and Et2O. To purify, dissolve it in Et2O [using CH2Cl2 instead of Et2O, protects the ester from acid], wash it with 10% aqueous Na2CO3, dry (MgSO4), filter and repeat as many times as possible until the Et2O layer loses its yellow colour, then remove the solvent below 20o (vacuum). Note that prolonged heating may lead to rapid decomposition and low yields. It can also be purified by steam distillation under reduced pressure but with considerable loss in yield. Place the residual oil in a brown bottle, keep below 10o, and use as soon as possible without distilling. For preparing esters usually the ethereal solution is used directly without purification. [Womack & Nelson Org Synth Coll Vol III 392 1955, UV: Miller & White J Am Chem Soc 79 5974 1957, Fieser 1 367 1967, Beilstein 3 IV 1495.]

 

Ethyl diazoacetate Preparation Products And Raw materials

Raw materials

Ethyl acetate-->Glycine ethyl ester hydrochloride-->Permethric acid-->Buffer solution, pH 1.00 (±0.01 at 25°C), No Color, Specpure, NIST Traceable

Preparation Products

Ethyl chrysanthemumate-->2,2-Dimethyl-3-(2-methylpropyl)cyclopropanecarboxylic acid p-(methoxymethyl)benzyl ester