Ethyl diazoacetate Property

Melting point:

-22 °C (lit.)

Boiling point:

140-141 °C/720 mmHg (lit.)

Density 

1.085 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.46(lit.)

Flash point:

115 °F

storage temp. 

2-8°C

solubility 

Chloroform (Slightly), DMSO (Soluble), Hexane (Slightly), Methanol (Slightly)

form 

Oil

color 

Light Yellow to Orange

Merck 

13,3021

BRN 

107654

NIST Chemistry Reference

Ethyl diazoacetate(623-73-4)

Safety

Hazard Codes 

Xn,F

Risk Statements 

5-10-22-40-67-65-48/20-38-11-63

Safety Statements 

36/37-62-16

RIDADR 

UN 1993 3/PG 3

WGK Germany 

3

RTECS 

AG5775000

HazardClass 

3.2

PackingGroup 

III

HS Code 

29270000

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H226Flammable liquid and vapour

H242Heating may cause a fire

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H351Suspected of causing cancer

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P308+P313IF exposed or concerned: Get medical advice/attention.

P370+P378In case of fire: Use … for extinction.

P403+P235Store in a well-ventilated place. Keep cool.

Ethyl diazoacetate Chemical Properties,Usage,Production

Synthesis

Glycine ethyl ester hydrochloride can be dissolved in a buffer solution composed of acetic acid and sodium acetate, and then dichloroethane is added as a solvent, and sodium nitrite solution is added dropwise at 10 to 15 ° C. After the dropwise addition, continue stirring for 15min. The separated organic layer is a dichloroethane solution of ethyl diazoacetate.
NH2CH2COOC2H5·HCl+NaNO2+HCl→N2CHCOOC2H5+NaCl+H2O

Chemical Properties

Liquid.

Uses

Reagent for ruthenium-catalyzed asymmetric cyclopropanation of alkenes.1

Uses

New Diazoacetate Formulations

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.]