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Cyanoacetic acid

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Cyanoacetic acid Basic information

Product Name:
Cyanoacetic acid
Synonyms:
  • 2-Cyanoacetic acid
  • Aceticacid,cyano-
  • Acide cyanacetique
  • Cyanoacetic
  • CYANOACETICE ACID
  • MALONIC MONONITRILE
  • MALONIC ACID MONONITRILE
  • CYANOCETIC ACID
CAS:
372-09-8
MF:
C3H3NO2
MW:
85.06
EINECS:
206-743-9
Product Categories:
  • intermediates
  • C1 to C5
  • Pharmaceutical Intermediates
  • Carbonyl Compounds
  • Carboxylic Acids
  • K00001
Mol File:
372-09-8.mol
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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)
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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
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

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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 acidSupplier

-Hebei Integrity Group Co., Ltd. Gold
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0311-84626641 18630108591
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Shanghai Kaisai Chemical Co., Ltd Gold
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021-33516722 13701817765
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Qufu Haida Tiancheng Biochemical Co., Ltd. Gold
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0537-0537-4531868 18553729317
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Weifang QianJin Fine Chemical Co., Ltd. Gold
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0536-2457064 13031698386
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Shanghai Yolne Chemical Co., Ltd. Gold
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021-62960152
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934678158@qq.com