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370460

Sigma-Aldrich

Diethoxyacetonitrile

97%

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About This Item

Linear Formula:
(C2H5O)2CHCN
CAS Number:
6136-93-2
Molecular Weight:
129.16
EC Number:
228-111-1
MDL number:
MFCD00043982
UNSPSC Code:
12352100
PubChem Substance ID:
24863070
NACRES:
NA.22

Assay

97%

form

liquid

refractive index

n20/D 1.4 (lit.)

bp

167.7 °C/773 mmHg (lit.)

mp

−19-−18 °C (lit.)

density

0.929 g/mL at 25 °C (lit.)

functional group

ether
nitrile

SMILES string

CCOC(OCC)C#N

InChI

1S/C6H11NO2/c1-3-8-6(5-7)9-4-2/h6H,3-4H2,1-2H3

InChI key

UDELMRIGXNCYLU-UHFFFAOYSA-N

General description

Diethoxyacetonitrile is a 2,2-dialkoxyalkanenitrile derivative. Reaction of hydrocyanic acid with various ortho esters of aliphatic and aromatic acids in the presence of acidic catalyst has been reported to afford diethoxyacetonitrile. Houben-Hoesch reaction of diethoxyacetonitrile with 1,2,4-trimethoxybenzene affords tris(2,4,5-trimethoxyphenyl)methane.

Application

Diethoxyacetonitrile may be used in the preparation of methyl 5-diethoxymethylimidazole-4-carboxylate, via anionic cycloaddition reaction with methyl isocyanoacetate.

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Warning

Hazard Statements

H226,H302 + H312 + H332

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Flam. Liq. 3

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

120.2 °F - closed cup

Flash Point(C)

49 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BGBC5426V
BGBC1918V
BGBC1526V
BGBB9791
MKBN7315V

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An anomalous Houben-Hoesch reaction and some applications in arylation reactions.
Sanchez-Viesca F, et al.
Organic Prep. and Proc. Int., 36(2), 135-140 (2004)
2, 2-Dialkoxyalkanenitriles.
Erickson JG.
Journal of the American Chemical Society, 73(3), 1338-1339 (1951)
An efficient synthesis of 5-diethoxymethylimidazole-4-carboxylate, a potential precursor for various imidazole derivatives.
Murakami T, et al.
Tetrahedron Letters, 23(45), 4729-4732 (1982)

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