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Safety Information

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:
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

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 Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

PDSCL

Deleterious substance

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

C88505-500G:4548173192758
C88505-BULK:
C88505-1KG:4548173192734
C88505-25G:4548173192741
C88505-VAR:
C88505-5KG:

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Certificates of Analysis (COA)

Lot/Batch Number
MKCN3741
MKCM6712
MKCL1238
SHBK5219
SHBJ4678

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The Ugi Reaction of Cyanoacetic Acid as a Route to Tetramic Acid Derivatives
Alvarez-Rodriguez NV, et al.
Synlett, 26(16), 2253-2256 (2015)
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)
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.
Isocyanoacetate derivatives: synthesis, reactivity, and application.
Anton V Gulevich et al.
Chemical reviews, 110(9), 5235-5331 (2010-07-09)
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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