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Safety Information

239976

Sigma-Aldrich

Cyanoacetic acid

≥99%

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About This Item

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

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.)

SMILES string

OC(=O)CC#N

InChI

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

InChI key

MLIREBYILWEBDM-UHFFFAOYSA-N

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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

Signal Word

Danger

Hazard Statements

H302 + H332,H314

Hazard Classifications

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

Supplementary Hazards

EUH031

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 1

Flash Point(F)

224.6 °F - closed cup

Flash Point(C)

107 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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
Courtney N Riddles et al.
Inorganica chimica acta, 412, 94-103 (2014-04-08)
High-yield syntheses of N-piperidine-cyanacetamide (
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
S Kotha et al.
Amino acids, 32(3), 387-394 (2006-10-13)
Two synthetic routes to bis-armed-alpha-amino acid derivatives are described. The first route involves alkylation of dibromo derivatives with ethyl isocyanoacetate under phase-transfer catalysis (PTC) conditions. The second route uses a palladium-mediated Suzuki-Miyaura cross-coupling reaction between a DL-4-boronophenylalanine derivative and aromatic
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