Cyanoacetamide

CYANOACETAMIDE · ACETAMIDE, 2-CYANO- · Cyanacetamide · CYAC · Kyanacetamid · Cyanacetamid · CYANOACETIC AMIDE · 2-CAA

Identifikatoren & physikalische Daten

CAS No.	107-91-5
Summenformel	C3H4N2O
Durchschnittliche Molmasse	84,08 g/mol
Monoisotopische Masse	84,03236275 g/mol
SMILES	N#CCC(N)=O
InChIKey	DGJMPUGMZIKDRO-UHFFFAOYSA-N
PubChem CID	7898
ChEMBL	CHEMBL2333142
EC No.	203-531-8
DTXSID	DTXSID2051552
Lokaler Name	2-Cyanacetamid

Chemische & physikalische Eigenschaften

XLogP	-1
Polarare Oberfläche (TPSA)	66,9
H-Brücken-Donoren	1
H-Brücken-Akzeptoren	2
Frei drehbare Bindungen	1
Schwere Atome	6
Formalladung	0
Komplexität	98,6
Stoffklassen	Nitrogen Compounds -> Nitriles
SpringerMaterials Properties	Boiling point
Color/Form	NEEDLES FROM ALCOHOLPLATES (WATER)WHITE POWDER
Löslichkeit	1 G DISSOLVES IN 6.5 ML COLD WATER1.3 G @ 0 °C IN 100 ML OF 95% ALCOHOL3.1 G @ 26 °C IN 100 ML OF 95% ALCOHOL7.0 G @ 44 °C IN 100 ML OF 95% ALCOHOL14.0 G @ 62 °C IN 100 ML OF 95% ALCOHOL21.5 G @ 71 °C IN 100 ML OF 95% ALCOHOLcold water: soluble1gm in 6.5ml
Siedepunkt	BP: DECOMPOSES154.34°C (rough estimate)
Schmelzpunkt	119.5 °C121.5 °C119-121 °C(lit.)
Physical Description	White solid[Hawley] White powder[MSDSonline]
Dichte	1,4 g/cm3
Brechungsindex	1.5110 (estimate)
Flammpunkt	419 °F
Lagerbedingungen	Sealed in dry,Room Temperature
pKa (Säurekonstante)	-1.27±0.10(Predicted)
Aggregatzustand	Crystalline Powder
Farbe	White to light cream
Geruch	Odorless
Merck	14,2688
BRN	878221
InChI	1S/C3H4N2O/c4-2-1-3(5)6/h1H2,(H2,5,6)
InChIKey	DGJMPUGMZIKDRO-UHFFFAOYSA-N
SMILES	NC(=O)CC#N
CAS Datenbank	107-91-5(CAS DataBase Reference)
NIST chemische Informationen	Acetamide, 2-cyano-(107-91-5)
EPA chemische Informationen	2-Cyanoacetamide (107-91-5)

Sicherheit & Vorschriften

GHS-Einstufung	WarningH302 (77.4%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 62 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Regulatorische Informationen	Chemical: Acetamide, 2-cyano-Status: Active Update: 26-05-2015 https://echa.europa.eu/registration-dossier/-/registered-dossier/11828Acetamide, 2-cyano-: Does not have an individual approval but may be used under an appropriate group standard
Brandpotenzial	SEE CYANIDES. MODERATE, BY CHEMICAL REACTION WITH HEAT, MOISTURE, ACID. /CYANIDES/
Gefahrenübersicht	Emergency treatment: Cyanide[HSDB] Subcutaneous LD50 (guinea pig) = 1155 mg/kgCauses tremor and muscle contractions[RTECS] An irritantHarmful by ingestion, inhalation, or skin absorption[Aldrich MSDS] See NITRILES.
Toxic Combustion Products	SEE CYANIDES. EMIT HYDROCYANIC ACID. /CYANIDES/
Hazard Classes and Categories	Acute Tox. 4 (77.4%)
Hazardous Reactivities and Incompatibilities	SEE CYANIDES. ON CONTACT WITH ACID, ACID FUMES, WATER OR STEAM, THEY WILL PRODUCE TOXIC & FLAMMABLE VAPORS. /CYANIDES/
Lagerbedingungen	SEE CYANIDES. ...MATERIALS WHICH ARE TOXIC AS STORED OR WHICH CAN DECOMP INTO TOXIC COMPONENTS...SHOULD BE STORED IN A COOL, WELL-VENTILATED PLACE, OUT OF DIRECT RAYS OF SUN, AWAY FROM AREAS OF HIGH FIRE HAZARD, & SHOULD BE PERIODICALLY INSPECTED... INCOMPATIBLE MATERIALS SHOULD BE ISOLATED FROM EACH OTHER. /CYANIDES/
Preventive Measures	SEE CYANIDES. VENTILATION CONTROL: THE BASIC VENTILATION METHODS ARE LOCAL & EXHAUST VENTILATION & DILUTION (GENERAL) VENTILATION. /CYANIDES/
Protective Action Criteria (PAC)	0.81 [mg/m3]8.7 [mg/m3]52 [mg/m3]
Treatment	Antidotes to cyanide poisoning include hydroxocobalamin and sodium nitrite, which release the cyanide from the cytochrome system, and rhodanase, which is an enzyme occurring naturally in mammals that combines serum cyanide with thiosulfate, producing comparatively harmless thiocyanate. Oxygen therapy can also be administered. (L97)
Gesundheitliche Auswirkungen	Exposure to high levels of cyanide for a short time harms the brain and heart and can even cause coma, seizures, apnea, cardiac arrest and death. Chronic inhalation of cyanide causes breathing difficulties, chest pain, vomiting, blood changes, headaches, and enlargement of the thyroid gland. Skin contact with cyanide salts can irritate and produce sores. (L96, L97)
Unerwünschte Wirkungen	Other Poison - Chemical Asphyxiant
Expositionspfade	Oral (L96)inhalation (L96)dermal (L96)
Toxizitätsübersicht	Organic nitriles decompose into cyanide ions both in vivo and in vitro. Consequently the primary mechanism of toxicity for organic nitriles is their production of toxic cyanide ions or hydrogen cyanide. Cyanide is an inhibitor of cytochrome c oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). It complexes with the ferric iron atom in this enzyme. The binding of cyanide to this cytochrome prevents transport of electrons from cytochrome c oxidase to oxygen. As a result, the electron transport chain is disrupted and the cell can no longer aerobically produce ATP for energy. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. (L97)
Signs and Symptoms	Cyanide poisoning is identified by rapid, deep breathing and shortness of breath, general weakness, giddiness, headaches, vertigo, confusion, convulsions/seizures and eventually loss of consciousness. (L96, L97)
Human Toxicity Excerpts	MANY ORGANIC NITRILES (OR CYANIDES) ARE DECOMP IN BODY TO YIELD TOXIC CYANIDE (CN- OR HCN). /CYANO ORGANIC COMPD/
Carcinogen Classification	No indication of carcinogenicity to humans (not listed by IARC).
Non-Human Toxicity Excerpts	CONTACT WITH SKIN OF GUINEA PIGS CAUSED SLIGHT IRRITATION WITH NO EVIDENCE OF TOXIC SYMPTOMS BY SKIN ABSORPTION. ...IT HAS VERY LOW TOXICITY.
Non-Human Toxicity Values	LD50 RATS ORAL MORE THAN 3200 MG/KGLD50 RATS INTRAPERITONEAL MORE THAN 800 MG/KG
Wassergefährdungsklasse (WGK)	2
TSCA-Inventar-Status	TSCA listed
UN-Transportnummer	UN 3439 6.1/PG 3
Zollcode	29269095
RTECS-Nr.	AB5950000
R-Sätze (R)	22-36/37/38-20/21/22
Gefahrensymbole	Xn
Sicherheitshinweise (S)	22-26-28A
Verpackungsgruppe	III
Lagerklasse	11 - Combustible Solids
Gefahrstoffdaten	107-91-5(Hazardous Substances Data)
Gefahrenklasse	Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3

Anwendungen & Verwendung

Verwenden

2-Cyanoacetamide was used in spectrofluorimetric method for the determination of some antihistaminic H1 receptor antagonist drugs such as ebastine, cetirizine dihydrochloride and fexofenadine hydrochloride. It may be used in fluorometric determination of 3,4-dihydroxyphenylalanine. It was used as post column fluorigenic derivatizing agent for the bio-analysis and pharmacokinetics of chitosan ester in rabbit serum. Cyanoacetamide is the starting reagent for vitamin B6 synthesis. It reacts with reducing carbohydrates in borate buffer to give intense fluorescence and is useful for the automated analysis of carbohydrates as borate complexes. It can also be used in the synthesis of heterocyclic compounds such as pyrazole, pyridine and pyrimidine derivatives. Moreover, it can also be applied for the spectrophotometric assay of the enzyme activity of cellulose in related host cells.

Herstellung & Synthese

synthetische

Cyanoacetamide can be prepared from ethyl cyanoacetate and ammonia. Cool the ethyl cyanoacetate to below 200°C, add concentrated ammonia water to react, and the mixture turns from turbid to clear. After cooling in cold water for 20 minutes, a precipitate is precipitated. After filtration and drying, the crude product is obtained, and then the crude product of cyanoacetamide is added. In the boiling ethanol, after dissolving it, add a small amount of activated carbon for decolorization and purification, filter, cool the filtrate to separate out the precipitate, and dry it at 80-100 ℃ to obtain the fine cyanoacetamide.