Cyanoacetic acid Chemical Properties

Melting point:

65 °C

Boiling point:

108 °C0.15 mm Hg(lit.)

Density 

1.3676 (rough estimate)

vapor pressure 

0.1 mm Hg ( 100 °C)

refractive index 

1.3764 (estimate)

Flash point:

226 °F

storage temp. 

Store below +30°C.

solubility 

H2O: soluble50mg/mL, clear, colorless to very faintly yellow

pka

2.45(at 25℃)

form 

Adhering Crystalline Solid

color 

White to light beige

PH

1.6 (50g/l, H2O, 20℃)

Water Solubility 

1000 g/L (20 ºC)

Sensitive 

Hygroscopic

Merck 

14,2689

BRN 

506325

Dielectric constant

33.0（4℃）

InChIKey

MLIREBYILWEBDM-UHFFFAOYSA-N

LogP

-0.76

CAS DataBase Reference

372-09-8(CAS DataBase Reference)

NIST Chemistry Reference

Acetic acid, cyano-(372-09-8)

EPA Substance Registry System

Cyanoacetic acid (372-09-8)

Safety Information

Hazard Codes 

C

Risk Statements 

22-31-34-52/53-20/22

Safety Statements 

26-36/37/39-45-61-20

RIDADR 

UN 3261 8/PG 2

WGK Germany 

2

RTECS 

AG3675000

F 

3-10-21

TSCA 

Yes

HS Code 

2926 90 70

HazardClass 

8

PackingGroup 

II

Hazardous Substances Data

372-09-8(Hazardous Substances Data)

Toxicity

LD50 orally in Rabbit: 1500 mg/kg LD50 dermal Rabbit > 2000 mg/kg

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Cyanoacetic acid Usage And Synthesis

Description

Cyanoacetic acid is an organic compound. It is a white, hygroscopic solid. The compound contains two functional groups, a nitrile (C≡N) and a carboxylic acid. It is a precursor to cyanoacrylates, components of adhesives.
Cyanoacetic acid is used in pharmaceutical industry for producing vitamin B6 and caffeine. It is also used in making dyes, agricultural chemicals, and in the synthesis of phenylacetic acid esters. It acts as a precursor cyanoacrylates viz. ethyl cyanoacrylate.

Chemical Properties

white to light beige adhering crystalline solid

Uses

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.

Uses

Cyanoacetic acid is used in pharmaceutical industry for producing vitamin B6 and caffeine. It is also used in making dyes, agricultural chemicals, and in the synthesis of phenylacetic acid esters. It acts as a precursor cyanoacrylates viz. ethyl cyanoacrylate.

Uses

Synthesis of intermediates; manufacture of barbital.

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.

Preparation

Cyanoacetic acid is prepared by treatment of chloroacetate salts with sodium cyanide followed by acidification. Electrosynthesis by cathodic reduction of carbon dioxide and anodic oxidation of acetonitrile also affords cyanoacetic acid.

Definition

ChEBI: A monocarboxylic acid that consists of acetic acid bearing a cyano substituent.

General Description

Yellow-brown liquid with an unpleasant odor. Sinks and mixes with water.

Air & Water Reactions

Water soluble.

Reactivity Profile

White, moderately toxic solid, combustible. When heated to decomposition Cyanoacetic acid emits toxic fumes of nitrile and oxides of nitrogen. A stirred mixture with furfuryl alcohol exploded violently upon heating [MCA Case History No 858].

Health Hazard

Contact irritates eyes and may irritate skin.

Fire Hazard

Special Hazards of Combustion Products: Toxic oxides of nitrogen and toxic and flammable acetonitrile vapors may form in fire.

Purification Methods

Recrystallise the acid to constant melting point from *benzene/acetone (2:3), and dry it over silica gel. [Beilstein 2 H 583, 2 I 253, 2 II 530, 2 III 1626, 2 IV 1888.]

Cyanoacetic acid(372-09-8)Related Product Information

• Glycine
• Folic acid
• Citric acid
• Ethyl N-cyanoethanimideate
• CYANOACETIC ACID METHYL ESTER
• Ethyl 2-(Chlorosulfonyl)acetate
• 2-Chloro-3-cyanopyridine
• Methylene dithiocyanate
• CYANOACETIC ACID ETHYL ESTER
• Sodium cyanoborohydride
• ETHYL 2-CYANOACRYLATE
• 2-Ethylhexyl cyanoacetate
• Ascoric Acid
• 2-(ETHOXYMETHYLENE)-2-CYANOACETIC ACID ETHYL ESTER
• CYANOACETIC ACID ALLYL ESTER
• ETHYL 2-CYANO-3-METHYLCROTONATE
• Ethyl acetamidocyanoacetate
• tert-Butyl cyanoacetate