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C88505

Sigma-Aldrich

Cyanoacetic acid

99%

Synonym(s):

2-Cyanoacetic acid, Cyanoethanoic acid, Malonic mononitrile, Monocyanoacetic acid

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About This Item

Linear Formula:
NCCH2COOH
CAS Number:
372-09-8
Molecular Weight:
85.06
Beilstein/REAXYS Number:
506325
EC Number:
206-743-9
MDL number:
MFCD00002677
UNSPSC Code:
12352100
PubChem Substance ID:
24893110
NACRES:
NA.22

vapor pressure

0.1 mmHg ( 100 °C)

Quality Level

100

assay

99%

form

crystals

bp

108 °C/0.15 mmHg (lit.)

mp

64-70 °C (lit.)

solubility

H2O: 50 mg/mL, clear, colorless to very faintly yellow

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 can be used as a reagent:
  • Along with acetic anhydride for cyanoacetylation of various pyrroles, indoles, and aniline derivatives. It can also be used in other reactions such as cyclizations, syntheses of coumarins and other heterocycles.
  • To prepare of key intermediate via Knoevenagel condensation in the total synthesis of 5-acetamido-substituted melatonin derivatives as MT3 receptor ligands.
  • In the synthesis of aminopyrrolinone derivatives by reacting Ugi adducts of cyanoacetic acid and aromatic aldehydes.

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_germany

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCT6916
MKCS4797
MKCS4798
MKCR6404
MKCN3741

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Cyanoacetylation of indoles, pyrroles and aromatic amines with the combination cyanoacetic acid and acetic anhydride
Slaett J, et al.
Synthesis, 2004(16), 2760-2765 (2004)
Synthesis of novel ??3 receptor ligands via an unusual Knoevenagel condensation
Volkova MS, et al.
Bioorganic & medicinal chemistry letters, 22(24), 7578-7581 (2012)
Structure-toxicity relationships for methyl esters of cyanoacetic acids to Tetrahymena pyriformis.
M B Cottrell et al.
Bulletin of environmental contamination and toxicology, 70(3), 549-556 (2003-02-20)
R H Denlinger et al.
Toxicology and applied pharmacology, 124(1), 59-66 (1994-01-01)
3,3'-Iminodipropionitrile (IDPN), a neurotoxicant that causes an excitatory CNS syndrome and a proximal axonopathy, is metabolized to beta-aminopropionitrile (BAPN), cyanoacetic acid (CAA), and beta-alanine (beta-ala) in rats. None of these metabolites are neurotoxic, suggesting that they are products of detoxification.
Synthesis of α-aryl nitriles through palladium-catalyzed decarboxylative coupling of cyanoacetate salts with aryl halides and triflates.
Rui Shang et al.
Angewandte Chemie (International ed. in English), 50(19), 4470-4474 (2011-04-08)
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