Cyanoacetamide

HCID 7898CAS 107-91-5

Basic information

Standard SMILES
N#CCC(N)=O
InChIKey
DGJMPUGMZIKDRO-UHFFFAOYSA-N
Molecular formula
C3H4N2O
Average molar mass
84.08 g/mol
Monoisotopic mass
84.03236275

Overview

cyanoacetamide has been reported in Apis with data available.

Names & identifiers

Preferred name
Cyanoacetamide
IUPAC
2-cyanoacetamide
English name
2-Cyanoacetamide
Molecular formula
C3H4N2O
Molecular weight
84.08

Names & synonyms

2-Cyanoacetamide107-91-5CYANOACETAMIDEAcetamide, 2-cyano-CyanacetamideMalonamide nitrileMalonamonitrileNitrilomalonamide3-Nitrilo-propionamideCyanoiminoacetic acidKyanacetamidUSAF KF-14
Show more names
CYACCyanacetamidCYANOACETIC AMIDE2-CAAusafkf-14
Propionamide nitrileAmid kyseliny kyanoctoveYBK38G2YXHMalonic acid, monoamide mononitrileNSC-6285DTXSID2051552RefChem:129041DTXCID6030104

Database identifiers

CAS
107-91-5
PubChem CID
7898
DTXSID
DTXSID2051552
ChEMBL
CHEMBL2333142
UNII
YBK38G2YXH
EC Number
203-531-8
Nikkaji
J4.067C

Properties

Computed structural properties

XLogP
-1
Topological polar surface area
66.9 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
2
Rotatable bonds
1
Heavy atoms
6

Experimental & physicochemical properties

Chemical ClassesNitrogen Compounds -> Nitriles
SpringerMaterials PropertiesBoiling point
Color/Form · 3 items

NEEDLES FROM ALCOHOL

PLATES (WATER)

WHITE POWDER

Solubility1 G DISSOLVES IN 6.5 ML COLD WATER; 1.3 G @ 0 °C IN 100 ML OF 95% ALCOHOL; 3.1 G @ 26 °C IN 100 ML OF 95% ALCOHOL; 7.0 G @ 44 °C IN 100 ML OF 95% ALCOHOL; 14.0 G @ 62 °C IN 100 ML OF 95% ALCOHOL; 21.5 G @ 71 °C IN 100 ML OF 95% ALCOHOL
Boiling PointBP: DECOMPOSES
Melting Point · 2 items

119.5 °C

121.5 °C

Physicochemical properties

Melting point
119 · 119-121 °C(lit.)
Boiling point
154.34 °C · 154.34°C (rough estimate)
Density
1 · 1,4 g/cm3
refractive index
1.511 · 1.5110 (estimate)
Flash point
419 °F · 419 °F
storage temp.
Sealed in dry,Room Temperature

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H302 (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.

Hazard information

Regulatory Information · 3 items

Chemical: Acetamide, 2-cyano-

Status: Active Update: 26-05-2015 https://echa.europa.eu/registration-dossier/-/registered-dossier/11828

Acetamide, 2-cyano-: Does not have an individual approval but may be used under an appropriate group standard

Fire PotentialSEE CYANIDES. MODERATE, BY CHEMICAL REACTION WITH HEAT, MOISTURE, ACID. /CYANIDES/
Hazards SummaryEmergency treatment: Cyanide; [HSDB] Subcutaneous LD50 (guinea pig) = 1155 mg/kg; Causes tremor and muscle contractions; [RTECS] An irritant; Harmful by ingestion, inhalation, or skin absorption; [Aldrich MSDS] See NITRILES.
Toxic Combustion ProductsSEE CYANIDES. EMIT HYDROCYANIC ACID. /CYANIDES/
Hazard Classes and CategoriesAcute Tox. 4 (77.4%)
Hazardous Reactivities and IncompatibilitiesSEE CYANIDES. ON CONTACT WITH ACID, ACID FUMES, WATER OR STEAM, THEY WILL PRODUCE TOXIC & FLAMMABLE VAPORS. /CYANIDES/

Safety & protection

Storage Conditions · 1 item

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 MeasuresSEE CYANIDES. VENTILATION CONTROL: THE BASIC VENTILATION METHODS ARE LOCAL & EXHAUST VENTILATION & DILUTION (GENERAL) VENTILATION. /CYANIDES/
Protective Action Criteria (PAC) · 3 items

0.81 [mg/m3]

8.7 [mg/m3]

52 [mg/m3]

Toxicology

Treatment · 1 item

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 · 1 item

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 EffectsOther Poison - Chemical Asphyxiant
Exposure RoutesOral (L96) ; inhalation (L96) ; dermal (L96)
Toxicity Summary · 1 item

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 SymptomsCyanide 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)

Safety data

PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
2
tsca
TSCA listed
rtecs
AB5950000
ridadr
UN 3439 6.1/PG 3
hs_code
29269095

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 1 item

Organic nitriles are converted into cyanide ions through the action of cytochrome P450 enzymes in the liver. Cyanide is rapidly absorbed and distributed throughout the body. Cyanide is mainly metabolized into thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase. Cyanide metabolites are excreted in the urine. (L96)

Uses & manufacturing

Uses · 2 items

Used in the synthesis of pharmaceuticals and plastics; [Hawley]

IN ORGANIC SYNTHESES (EG STARTING MATERIAL FOR VITAMIN B6 SYNTHESIS)

Methods of ManufacturingPREPARED BY ACTION OF AQ OR ALCOHOLIC AMMONIA ON CYANOACETIC ESTER: HESSE, AM CHEM J 18, 724 (1896); THOLE, THORPE, J CHEM SOC 99, 429 (1911); OTT, LOPMANN, BER 55, 1258 (1922); CORSON ET AL, ORG SYN COLL VOL I (2ND ED, 1941) P 179.
General Manufacturing InformationAcetamide, 2-cyano-: ACTIVE
Applications · 2 items

Uses2-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 DescriptionCyanoacetamide 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 methods · 1 item

PreparationCyanoacetamide 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.

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
T&W GROUP021-61551611 13296011611 · [email protected]

Additional notes

Definition2-Cyanoacetamide is an acetic amide with a nitrile functional group. It is a codon of glutamine that directs the placement of glutamine into a polypeptide.

Related reactions

476 records

Linked notes

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Cyanoacetamide (HCID 7898)|Huagongshe