Cyanoacetamide

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

Identifiers & Physical Properties

CAS No.	107-91-5
Molecular formula	C3H4N2O
Average molar mass	84.08 g/mol
Monoisotopic mass	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

Chemical & Physical Properties

XLogP	-1
Topological polar surface area	66.9
Hydrogen bond donors	1
Hydrogen bond acceptors	2
Rotatable bonds	1
Heavy atoms	6
Formal charge	0
Complexity	98.6
Chemical classes	Nitrogen Compounds -> Nitriles
SpringerMaterials Properties	Boiling point
Color/Form	NEEDLES FROM ALCOHOLPLATES (WATER)WHITE POWDER
Solubility	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
Boiling point	BP: DECOMPOSES154.34°C (rough estimate)
Melting point	119.5 °C121.5 °C119-121 °C(lit.)
Physical Description	White solid[Hawley] White powder[MSDSonline]
Density	1,4 g/cm3
Refractive index	1.5110 (estimate)
Flash point	419 °F
Storage conditions	Sealed in dry,Room Temperature
pKa (acidity coefficient)	-1.27±0.10(Predicted)
Physical state	Crystalline Powder
Color	White to light cream
Odor	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 DataBase Reference	107-91-5(CAS DataBase Reference)
EWG's Food Scores	1
FDA UNII	YBK38G2YXH
NIST Chemistry Reference	Acetamide, 2-cyano-(107-91-5)
EPA Substance Registry System	2-Cyanoacetamide (107-91-5)
UNSPSC Code	12352100
NACRES	NA.22
GHS pictogram	GHS07
Signal word	Warning
GHS hazard statements	H302-H315-H319-H335
GHS precautionary statements	P261-P264-P270-P301+P312-P302+P352-P305+P351+P338
Target organs	Respiratory system
Personal protective equipment (PPE)	dust mask type N95 (US), Eyeshields, Gloves
Hazard symbols	Xn
Risk statements (R)	22-36/37/38-20/21/22
Safety statements (S)	22-26-28A
UN transport number	UN 3439 6.1/PG 3
Water hazard class (WGK)	2
RTECS number	AB5950000
TSCA inventory status	TSCA listed
Packing group	III
Customs code	29159080
Storage class	11 - Combustible Solids
Hazard class	Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
Hazardous substances data	107-91-5(Hazardous Substances Data)
REACH registrations	Active

Safety & Regulations

GHS classification	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.
Regulatory information	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
Fire potential	SEE CYANIDES. MODERATE, BY CHEMICAL REACTION WITH HEAT, MOISTURE, ACID. /CYANIDES/
Hazards summary	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/
Storage conditions	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)
Health effects	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)
Adverse effects	Other Poison - Chemical Asphyxiant
Exposure routes	Oral (L96)inhalation (L96)dermal (L96)
Toxicity summary	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
Personal protective equipment (PPE)	dust mask type N95 (US), Eyeshields, Gloves
Water hazard class (WGK)	2
TSCA inventory status	TSCA listed
RTECS number	AB5950000
UN transport number	UN 3439 6.1/PG 3
Customs code	29269095
Risk statements (R)	22-36/37/38-20/21/22
Signal word	Warning
GHS pictogram	GHS07
Hazard symbols	Xn
Safety statements (S)	22-26-28A
Storage class	11 - Combustible Solids
Packing group	III
Target organs	Respiratory system
GHS hazard statements	H302-H315-H319-H335
REACH registrations	Active
Hazard class	Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
GHS precautionary statements	P261-P264-P270-P301+P312-P302+P352-P305+P351+P338
Hazardous substances data	107-91-5(Hazardous Substances Data)

Applications & Uses

Uses

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.

General Description

Cyanoacetamide is the starting reagent for vitamin B6 synthesis. It reacts with reducing carbohydrates in borate buffer to give intense fluorescence andis useful for the automated analysis of carbohydrates as borate complexes.

Preparation & Synthesis

Preparation

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.