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Merck
CN

226319

Ethyl isocyanoacetate

95%

Synonym(s):

α-Isocyanoacetic acid ethyl ester, (Ethoxycarbonyl)methyl isonitrile, 2-Ethoxy-2-oxoethyl isocyanide, 2-Ethyloxycarbonylmethyl isocyanide, Ethoxycarbonylmethyl isocyanide, Ethyl α-isocyanoacetate, Ethyl 2-isocyanoacetate, Isocyanoacetic acid ethyl ester

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About This Item

Linear Formula:
CNCH2COOCH2CH3
CAS Number:
2999-46-4
Molecular Weight:
113.11
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24853557
EC Number:
221-077-9
Beilstein/REAXYS Number:
3588613
MDL number:
MFCD00000007

Key Documents

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Product Name

Ethyl isocyanoacetate, 95%

InChI key

FPULFENIJDPZBX-UHFFFAOYSA-N

InChI

1S/C5H7NO2/c1-3-8-5(7)4-6-2/h3-4H2,1H3

SMILES string

CCOC(=O)C[N+]#[C-]

assay

95%

form

liquid

refractive index

n20/D 1.418 (lit.)

bp

194-196 °C (lit.)

density

1.035 g/mL at 25 °C (lit.)

functional group

amine
ester
isonitrile

storage temp.

2-8°C

Quality Level

100

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Application

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

General description

Ethyl isocyanoacetate is an isocyanide ester that serves as a building block for the production of heterocycles.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Inhalation - Acute Tox. 4 Oral

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

183.2 °F - closed cup

flash_point_c

84 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Regulatory Information

危险化学品
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Certificates of Analysis (COA)

Lot/Batch Number
STBL1708
STBJ3749
STBH6685
STBH2264
STBG8437

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Flow-assisted synthesis of heterocycles via multicomponent reactions
Van MS, et al.
Syntheses of Heterocyclic Compounds. , 133-159 (2018)
Yifei Li et al.
Chemical communications (Cambridge, England), 48(100), 12228-12230 (2012-11-13)
A novel and efficient route for the synthesis of 7-aza-tetrahydroindoles from N-aryl/alkyl-alkenoylacetamides and ethyl isocyanoacetate is described. A mechanism, involving a stepwise [3+2] cycloaddition-intramolecular aza-Michael addition cascade, is proposed that explains the origin of the double nucleophilic attack on the
Tetrahedron Letters, 47, 5481-5481 (2006)
Z Q Gu et al.
Journal of medicinal chemistry, 36(8), 1001-1006 (1993-04-16)
A series of imidazo[1,5-a][1,4]benzodiazepine esters have been synthesized with varying ester side chains and 8-position substituents. The affinities of these compounds were evaluated at both "diazepam-insensitive" (DI) and diazepam-sensitive (DS) subtypes of the benzodiazepine receptor (BZR). A profound steric effect
Chikashi Kanazawa et al.
Journal of the American Chemical Society, 128(33), 10662-10663 (2006-08-17)
The copper-catalyzed reaction between two different isocyanides produces the corresponding heteroaromatization products, imidazoles, in good yields. The reaction proceeds most probably through the activation of the sp3 C-H bond in the isocyanides by a copper catalyst, followed by a [3
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