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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
Assay:
95%
Form:
liquid

Key Documents

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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

Quality Level

100

bp

194-196 °C (lit.)

density

1.035 g/mL at 25 °C (lit.)

functional group

amine, ester, isonitrile

storage temp.

2-8°C

Related Categories

General description

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

Application

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

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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Tetrahedron Letters, 47, 5481-5481 (2006)
Flow-assisted synthesis of heterocycles via multicomponent reactions
Van MS, et al.
Syntheses of Heterocyclic Compounds. , 133-159 (2018)
Tetrahedron Letters, 34, 5463-5463 (1993)
Marcus Baumann et al.
Organic letters, 8(23), 5231-5234 (2006-11-03)
[Structure: see text] A multipurpose mesofluidic flow reactor capable of producing gram quantities of material has been developed as an automated synthesis platform for the rapid on-demand synthesis of key building blocks and small exploratory libraries. The reactor is configured
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
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