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Cyanoacetic acid

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  • CAS:372-09-8
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Cyanoacetic acid Basic information
Product Name:Cyanoacetic acid
Synonyms:cyano-aceticaci;Kyselina kyanoctova;kyselinakyanoctova;Monocyanoacetic acid;monocyanoaceticacid;NCCH2COOH;USAF kf-17;usafkf-17
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
Cyanoacetic acid Structure
Cyanoacetic acid Chemical Properties
Melting point 65 °C
Boiling point 108 °C0.15 mm Hg(lit.)
density 1.3676 (rough estimate)
bulk density700kg/m3
vapor pressure 0.1 mm Hg ( 100 °C)
refractive index 1.3764 (estimate)
Fp 226 °F
storage temp. Store below +30°C.
solubility H2O: soluble50mg/mL, clear, colorless to very faintly yellow
pka2.45(at 25℃)
form Adhering Crystalline Solid
color White to light beige
PH1.6 (50g/l, H2O, 20℃)
Water Solubility 1000 g/L (20 ºC)
Sensitive Hygroscopic
Merck 14,2689
BRN 506325
Dielectric constant33.0(4℃)
InChI1S/C3H3NO2/c4-2-1-3(5)6/h1H2,(H,5,6)
InChIKeyMLIREBYILWEBDM-UHFFFAOYSA-N
SMILESOC(=O)CC#N
LogP-0.76
CAS DataBase Reference372-09-8(CAS DataBase Reference)
NIST Chemistry ReferenceAcetic acid, cyano-(372-09-8)
EPA Substance Registry SystemCyanoacetic 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
3-10-21
TSCA TSCA listed
HS Code 2926 90 70
HazardClass 8
PackingGroup II
Storage Class8A - Combustible corrosive hazardous materials
Hazard ClassificationsAcute Tox. 4 Inhalation
Acute Tox. 4 Oral
Eye Dam. 1
Skin Corr. 1B
Hazardous Substances Data372-09-8(Hazardous Substances Data)
ToxicityLD50 orally in Rabbit: 1500 mg/kg LD50 dermal Rabbit > 2000 mg/kg
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
ALFA English
Cyanoacetic acid Usage And Synthesis
DescriptionCyanoacetic 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 Propertieswhite to light beige adhering crystalline solid
UsesCyanoacetic 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.
UsesCyanoacetic 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.
UsesSynthesis of intermediates; manufacture of barbital.
DefinitionChEBI: A monocarboxylic acid that consists of acetic acid bearing a cyano substituent.
ApplicationCyanoacetic 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.
PreparationCyanoacetic 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.
General DescriptionYellow-brown liquid with an unpleasant odor. Sinks and mixes with water.
Air & Water ReactionsWater soluble.
Reactivity ProfileWhite, 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 HazardContact irritates eyes and may irritate skin.
Fire HazardSpecial Hazards of Combustion Products: Toxic oxides of nitrogen and toxic and flammable acetonitrile vapors may form in fire.
Purification MethodsRecrystallise 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.]
Tag:Cyanoacetic acid(372-09-8) Related Product Information
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