| Identification | More | [Name]
Cyanoacetic acid | [CAS]
372-09-8 | [Synonyms]
CYAD
CYANOACETIC ACID
CYANOCETIC ACID
MALONIC ACID MONONITRILE
MALONIC MONONITRILE
2-Cyanoacetic acid
Aceticacid,cyano-
Acide cyanacetique
acidecyanacetique
acidecyanacetique(french)
Cyanessigsaeure
cyano-aceticaci
Kyselina kyanoctova
kyselinakyanoctova
Monocyanoacetic acid
monocyanoaceticacid
NCCH2COOH
USAF kf-17
usafkf-17
Methyl and Ethyl esters | [EINECS(EC#)]
206-743-9 | [Molecular Formula]
C3H3NO2 | [MDL Number]
MFCD00002677 | [Molecular Weight]
85.06 | [MOL File]
372-09-8.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light beige adhering crystalline solid | [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) | [Fp ]
226 °F
| [storage temp. ]
Store at 0-5°C | [solubility ]
H2O: soluble50mg/mL, clear, colorless to very faintly yellow | [form ]
Adhering Crystalline Solid | [pka]
2.45(at 25℃) | [color ]
White to light beige | [PH]
1.6 (50g/l, H2O, 20℃) | [Water Solubility ]
1000 g/L (20 ºC) | [Sensitive ]
Hygroscopic | [Detection Methods]
T | [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]
372-09-8(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
C | [Risk Statements ]
R22:Harmful if swallowed.
R31:Contact with acids liberates toxic gas.
R34:Causes burns.
R52/53:Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
R20/22:Harmful by inhalation and if swallowed . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S61:Avoid release to the environment. Refer to special instructions safety data sheet .
S20:When using, do not eat or drink . | [RIDADR ]
UN 3261 8/PG 2
| [WGK Germany ]
2
| [RTECS ]
AG3675000
| [F ]
3-10-21 | [TSCA ]
Yes | [HazardClass ]
8 | [PackingGroup ]
II | [HS Code ]
29269090 | [Hazardous Substances Data]
372-09-8(Hazardous Substances Data) | [Toxicity]
LD50 orally in Rabbit: 1500 mg/kg LD50 dermal Rabbit > 2000 mg/kg |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
Dichloromethane-->Chloroacetic acid-->Sodium chloroacetate | [Preparation Products]
Ethyl cyanoacetate-->Diethyl malonate-->Malonic acid-->Dimethyl malonate-->Caffeine-->4-PYRIDIN-2-YLISOXAZOL-5-AMINE-->Sulindac-->2,4-Dichloro-5-cyanopyrimidine-->2,2-Dibromo-2-cyanoacetamide-->MALONIC ACID DISODIUM SALT-->6-AMINO-1,3-DIMETHYL-5-NITROSOURACIL-->1-methyl-4-[3,3,3-tris(4-chlorophenyl)propionyl]piperazine-->Cymoxanil-->Octyl cyanoacetate-->2-cyano-N-methyl-N-[(methylamino)carbonyl]acetamide-->2-cyano-N-[(ethylamino)carbonyl]acetamide-->Dichloroacetonitrile-->3,3,3-Tris(4-chlorophenyl)propionic acid-->ENPROFYLLINE-->3,3,3-tris(p-chlorophenyl)propionyl chloride-->5,6-Diamino-1,3-dimethyluracil hydrate |
| Hazard Information | Back Directory | [General Description]
Yellow-brown liquid with an unpleasant odor. Sinks and mixes with water. | [Reactivity Profile]
White, moderately toxic solid, combustible. When heated to decomposition CYANOACETIC ACID(372-09-8) emits toxic fumes of nitrile and oxides of nitrogen. A stirred mixture with furfuryl alcohol exploded violently upon heating [MCA Case History No 858]. | [Air & Water Reactions]
Water soluble. | [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. | [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]
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. | [Definition]
ChEBI: A monocarboxylic acid that consists of acetic acid bearing a cyano substituent. | [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. | [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.] |
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