Ethyl isocyanoacetate Chemical Properties

Boiling point:

194-196 °C (lit.)

Density 

1.035 g/mL at 25 °C (lit.)

vapor pressure 

61.7Pa at 25℃

refractive index 

n20/D 1.418(lit.)

Flash point:

184 °F

storage temp. 

2-8°C

solubility 

Chloroform, Methanol (Slightly)

form 

Liquid

color 

Clear amber to dark brown

Water Solubility 

Miscible with organic solvents. Slightly miscible with water.

Sensitive 

Moisture & Light Sensitive

BRN 

3588613

Exposure limits

NIOSH: IDLH 25 mg/m3

LogP

0.91 at 25℃

CAS DataBase Reference

2999-46-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/22-20/21/22

Safety Statements 

36/37/39-26-36/37-24/25

RIDADR 

UN 2810 6.1/PG 3

WGK Germany 

3

F 

8-9-21

HazardClass 

6.1

PackingGroup 

III

HS Code 

29299090

MSDS

• Language:English Provider:Ethyl isocyanoacetate
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Ethyl isocyanoacetate Usage And Synthesis

Chemical Properties

Light yellow to brom liquid. Slightly soluble in water and lye, miscible in ethanol and ether.

Uses

Ethyl Isocyanoacetate, is a cyclization synthon used to prepare pyrroles, oxazolines, benzodiazepines, oxazoles and imidazoles. Ethyl isocyanoacetate can be used to prepare pyrroles,1,2 oxazolines, benzodiazepines, oxazoles and imidazoles.

Uses

Ethyl isocyanoacetate is used in the syntheses of 7-aza-tetrahydroindoles, oxazolines, benzodiazepines, imidazoles and oxazoles. For example, it is involved in the synthesis of 1H-indole-2-carboxylate by condensing with 2-bromo benzenealdehyde using CuI as a catalyst. It is a precursor used in the preparation of ethyl thiazole-4-carboxylate upon reaction with O-ethyl thioformate.

Preparation

synthesis of ethyl isocyanoacetate
A solution containing N-formyl glycine ethyl ester (1, 1.31 g, 10 mmol), DIPEA (2.62 g, 20 mmol) and DMAP (0.45 g, 3 mmol) in dry DCM (10 mL) was loaded in a sample loop and combined with a second stream containing triphosgene (2, 0.98 g, 3.3 mmol) also dissolved in dry DCM (10 mL) at individual channel flow rates of 0.5 mL/min. The combined stream was directed into two linked 10 mL FEP reactor vessels to achieve a 20 minutes residence time at ambient temperature. The output was collect and the solvent was carefully evaporated to 80% of its total volume. The crude material was filtered through silica (5 g) and washed with DCM (2 × 10 mL) to obtain the salt-free product. The desired product 3 was obtained as dark yellow oil after evaporation of the organic phase (1.03 g, 91 % isolated yield, >97% purity by 1H NMR).

General Description

Material may darken upon storage

Ethyl isocyanoacetate(2999-46-4)Related Product Information

• Ethyl cellulose
• Ethylparaben
• Ethyl methoxyacetate
• Ethyl acetoacetate
• Ethylbenzene
• 2-Methoxyethyl cyanoacetate
• Ethyl cyanoglyoxylate-2-oxime
• Ethyl N-cyanoethanimideate
• Ethyl isobutyrate
• METHYL ISOCYANOACETATE
• Tetraethyl orthosilicate
• Cyanoacetic acid
• Ethyl formate
• Ethyl acrylate
• Ethyl bromoacetate
• Ethanol
• Ethyl cyanoacetate
• CHLOROETHANE