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Merck
CN

239976

Cyanoacetic acid

≥99%

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About This Item

Linear Formula:
NCCH2COOH
CAS Number:
372-09-8
Molecular Weight:
85.06
EC Number:
206-743-9
UNSPSC Code:
12352100
PubChem Substance ID:
24854397
Beilstein/REAXYS Number:
506325
MDL number:
MFCD00002677

Key Documents

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InChI key

MLIREBYILWEBDM-UHFFFAOYSA-N

InChI

1S/C3H3NO2/c4-2-1-3(5)6/h1H2,(H,5,6)

SMILES string

OC(=O)CC#N

vapor pressure

0.1 mmHg ( 100 °C)

assay

≥99%

bp

108 °C/0.15 mmHg (lit.)

mp

64-70 °C (lit.)

solubility

alcohol: soluble(lit.), benzene: slightly soluble(lit.), chloroform: slightly soluble(lit.), diethyl ether: soluble(lit.), water: soluble(lit.)

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Application

Cyanoacetic acid was used in the synthesis of N-piperidine-cyanacetamide and N-morpholyl-cyanacetamide. It was also used in the preparation of a panchromatic dye for dye-sensitized solar cells.

pictograms

CorrosionExclamation mark
GHS05,GHS07

signalword

Danger

Hazard Classifications

Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Dam. 1 - Skin Corr. 1B

supp_hazards

EUH031

Storage Class

8A - Combustible corrosive hazardous materials

wgk

WGK 1

flash_point_f

224.6 °F - closed cup

flash_point_c

107 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
SHBF1266V
SHBD1101V
SHBB8881V
1451656V
1451656

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Shao-Gang Li et al.
Chemical communications (Cambridge, England), 50(33), 4309-4311 (2014-03-19)
A panchromatic dye was synthesized with an isoindigo core as a linker to bridge with a bis(4-tert-butylphenyl)phenylamine donor and a cyanoacetic acid acceptor for dye-sensitized solar cells, showing a broad spectral response and a high conversion efficiency of 7.55% under
Yijun Huang et al.
Molecular diversity, 15(1), 3-33 (2010-03-02)
The Gewald reaction of sulfur, cyanoacetic acid derivatives, and oxo-component (G-3CR) yielding highly substituted 2-aminothiophene derivatives has seen diverse applications in combinatorial and medicinal chemistry. Its products are of great use in pharmaceutical industry mainly as small molecular weight inhibitors.
Hamad M Al-Matar et al.
Molecules (Basel, Switzerland), 17(1), 897-909 (2012-01-20)
3-Aroyl and 3-heteroaroyl substituted 3-oxoalkanenitriles were synthesized by the reactions of activated aromatic and hetero-aromatic substances with cyanoacetic acid in the presence of acetic anhydride. As part of studies focusing on the preparation of cyanoacetyl-1-N-methylbenzimidazole, we observed that reaction of
Tian-Yu Liu et al.
Organic & biomolecular chemistry, 4(11), 2097-2099 (2006-05-27)
The bifunctional thiourea-tertiary amine derivatives of simple chiral diamines serve as highly enantioselective catalysts for the Michael addition of alpha-substituted cyanoacetates to vinyl sulfones, giving an efficient protocol for the construction of an all-carbon substituted quaternary stereocentre.
Courtney N Riddles et al.
Inorganica chimica acta, 412, 94-103 (2014-04-08)
High-yield syntheses of N-piperidine-cyanacetamide (
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