ETHYL DIAZOACETOACETATE Property

Boiling point:

102-103 °C(Press: 12 Torr)

Density 

1.131 g/mL at 25 °C (lit.)

vapor pressure 

0.36 psi ( 20 °C)

refractive index 

n20/D 1.474(lit.)

Flash point:

185 °F

form 

liquid

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

29270000

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H242Heating may cause a fire

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

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

P235Keep cool.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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

P403+P233Store in a well-ventilated place. Keep container tightly closed.

ETHYL DIAZOACETOACETATE Chemical Properties,Usage,Production

Uses

Ethyl diazoacetoacetate can be used as a reactant to synthesize:

• 1,4-oxathiocines and thiopyran derivatives via Rh-catalyzed reaction with 2-amino-4,5-dihydro-3-thiophenecarbonitriles.
• β-keto esters via C-H insertion reaction with aromatic aldehydes using NbCl5 as a catalyst.
• Diazoacetoacetate derivatives by reacting with aldehydes via aldol condensation and subsequent and in situ oxidation reaction.
• Isoquinolone and pyridone derivatives by Rh-catalyzed C-H activation/annulation reaction with various N-methoxybenzamides.

Synthesis Reference(s)

Tetrahedron Letters, 5, p. 2285, 1964 DOI: 10.1002/lipi.19640660210

General Description

Ethyl diazoacetoacetate is a diazo compound. It participates in Rh₂(OAc)₄-catalyzed reactions with arylalkylamines and diarylamines. Reaction of ethyl diazoacetoacetate with N-methyl pyrrole and pyrrole derivatives has been studied.