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Merck
CN

C88505

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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24893110
EC Number:
206-743-9
Beilstein/REAXYS Number:
506325
MDL number:
MFCD00002677
Assay:
99%
Form:
crystals

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%

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

Quality Level

100

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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

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

危险化学品
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Certificates of Analysis (COA)

Lot/Batch Number
MKCX2849
MKCT6916
MKCS4798
MKCS4797
MKCR6404

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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)
The Ugi Reaction of Cyanoacetic Acid as a Route to Tetramic Acid Derivatives
Alvarez-Rodriguez NV, et al.
Synlett, 26(16), 2253-2256 (2015)
Copper-catalyzed 1,4-addition of organoboronates to alkylidene cyanoacetates: mechanistic insight and application to asymmetric catalysis.
Keishi Takatsu et al.
Angewandte Chemie (International ed. in English), 50(24), 5548-5552 (2011-05-04)
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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