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Ethyl isocyanoacetate

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Ethyl isocyanoacetate Basic information

Product Name:
Ethyl isocyanoacetate
Synonyms:
  • Acetic acid, isocyano-, ethyl ester
  • Ethylisocyanoacetate,98%
  • Isocyanoacetate
  • ethyl isocyanoacetate 2999-46-4
  • (2-Oxo-2-ethoxyethyl) isocyanide
  • 2-Oxo-2-ethoxyethyl isocyanide
  • Ethoxycarbonylmethyl isocyanide
  • Ethyl 2-isocyanoacetate
CAS:
2999-46-4
MF:
C5H7NO2
MW:
113.11
EINECS:
221-077-9
Product Categories:
  • Building Blocks
  • Chemical Synthesis
  • straight chain compounds
  • fine chemicals, specialty chemicals, intermediates, electronic chemical, organic synthesis
  • Nitrogen Compounds
  • Organic Building Blocks
  • pharmacetical
  • Naphthyridine,Quinoline
  • Isocyanides
  • Nitrogen Compounds
  • Organic Building Blocks
Mol File:
2999-46-4.mol
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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
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)
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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
8-9-21
HazardClass 
6.1
PackingGroup 
III
HS Code 
29299090

MSDS

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Ethyl isocyanoacetate Usage And Synthesis

Chemical Properties

Light yellow to brom liquid

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.

Uses

Ethyl isocyanoacetate was used in the synthesis of 7-aza-tetrahydroindoles. It was also used to prepare pyrroles, oxazolines, benzodiazepines, oxazoles and imidazoles.

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 Preparation Products And Raw materials

Preparation Products

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