ChemicalBook > CAS DataBase List > Cyanoacetic acid

Cyanoacetic acid

Product Name
Cyanoacetic acid
CAS No.
372-09-8
Chemical Name
Cyanoacetic acid
Synonyms
2-Cyanoacetic acid;2-cyanoacetate;Cyanicycnab acid;CYAD;Cyanoacetic;NCCH2COOH;usafkf-17;USAF kf-17;Cyanessigsure;CYANOCETIC ACID
CBNumber
CB8217349
Molecular Formula
C3H3NO2
Formula Weight
85.06
MOL File
372-09-8.mol
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Cyanoacetic acid Property

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

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
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H314Causes severe skin burns and eye damage

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
C88505
Product name
Cyanoacetic acid
Purity
99%
Packaging
25g
Price
$68.2
Updated
2024/03/01
Sigma-Aldrich
Product number
C88505
Product name
Cyanoacetic acid
Purity
99%
Packaging
1kg
Price
$225
Updated
2024/03/01
Sigma-Aldrich
Product number
8.00252
Product name
Cyanoacetic acid
Purity
for synthesis
Packaging
1kg
Price
$122
Updated
2022/05/15
TCI Chemical
Product number
C0439
Product name
Cyanoacetic Acid
Purity
>98.0%(T)
Packaging
25g
Price
$34
Updated
2024/03/01
TCI Chemical
Product number
C0439
Product name
Cyanoacetic Acid
Purity
>98.0%(T)
Packaging
500g
Price
$271
Updated
2024/03/01
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Cyanoacetic acid Chemical Properties,Usage,Production

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 Preparation Products And Raw materials

Raw materials

Chloroacetic acid Suspending agent Dichloromethane Sodium chloroacetate

Preparation Products

ENPROFYLLINE Caffeine 3,3,3-Tris(4-chlorophenyl)propionic acid 2-cyano-N-methyl-N-[(methylamino)carbonyl]acetamide 1-methyl-4-[3,3,3-tris(4-chlorophenyl)propionyl]piperazine 2-cyano-N-[(ethylamino)carbonyl]acetamide Sulindac Dimethyl malonate 3,3,3-tris(p-chlorophenyl)propionyl chloride 4-PYRIDIN-2-YLISOXAZOL-5-AMINE 5,6-Diamino-1,3-dimethyluracil hydrate Cymoxanil 6-AMINO-1,3-DIMETHYL-5-NITROSOURACIL 2,4-Dichloro-5-cyanopyrimidine 2,2-Dibromo-2-cyanoacetamide Octyl cyanoacetate Dichloroacetonitrile MALONIC ACID DISODIUM SALT Diethyl malonate Malonic acid Ethyl cyanoacetate
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Cyanoacetic acid Suppliers

Americas 1 Belgium 4 Canada 1 China 248 Europe 4 France 2 Germany 12 India 56 Japan 8 Slovakia 1 South Korea 3 Sweden 1 Switzerland 2 The Netherlands 2 Ukraine 1 United Kingdom 12 United States 58 Global 416
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View Lastest Price from Cyanoacetic acid manufacturers

Hebei Weibang Biotechnology Co., Ltd
Product
Cyanoacetic acid 372-09-8
Price
US $10.00/KG
Min. Order
100KG
Purity
99%
Supply Ability
100 mt
Release date
2021-07-21
Zhuozhou Wenxi import and Export Co., Ltd
Product
Cyanoacetic acid 372-09-8
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-06-27
Career Henan Chemical Co
Product
Cyanoacetic acid 372-09-8
Price
US $1.00/KG
Min. Order
1KG
Purity
98%
Supply Ability
20tons
Release date
2019-09-05

372-09-8, Cyanoacetic acidRelated Search:

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

  • 2-Cyanoacetic acid
  • Aceticacid,cyano-
  • Acide cyanacetique
  • Cyanoacetic
  • CYANOACETICE ACID
  • MALONIC MONONITRILE
  • MALONIC ACID MONONITRILE
  • CYANOCETIC ACID
  • CYANOACETIC ACID
  • CYAD
  • Cyanicycnab acid
  • Cyanessigsure
  • CYANOACETIC ACID 30% SOLUTION IN WATER
  • Cyanoacetic acid ,95%
  • Cyanoacetic acid, 99% 25GR
  • Cyanoacetic Acid, 99 Percent
  • 2-cyanoacetate
  • acidecyanacetique
  • acidecyanacetique(french)
  • Cyanessigsaeure
  • cyano-aceticaci
  • Kyselina kyanoctova
  • kyselinakyanoctova
  • Monocyanoacetic acid
  • monocyanoaceticacid
  • NCCH2COOH
  • USAF kf-17
  • usafkf-17
  • CYANOACETIC ACID, 99+%
  • CyanoaceticAcid,>98%
  • Methyl and Ethyl esters
  • malonic mkononitrile
  • Cyanoacetic acid - 70% aqueous solution
  • Cyanoacetic Acid &gt
  • Acetic acid, 2-cyano-
  • Cyanoacetic acid ISO 9001：2015 REACH
  • Cyanoacetic acid, 55% solution
  • Milrinone Impurity U
  • Tolvaptan Impurity 53
  • Cyano Acetic Acid 70% / 98%
  • Cyanoacetic Acid 96% For Synthesis
  • 372-09-8
  • NCCH2CO2H
  • C3H3NO2
  • Organic Building Blocks
  • CARBOXYLIC ACID
  • Building Blocks
  • C1 to C5
  • Carboxylic Acids
  • Carbonyl Compounds
  • intermediates
  • C1 to C5
  • Carbonyl Compounds
  • Carboxylic Acids
  • Pharmaceutical Intermediates
  • K00001