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
Show more names
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
- Formal charge
- 0
- Complexity
- 98.6
Experimental & physicochemical properties
Color/Form
NEEDLES FROM ALCOHOL
PLATES (WATER)
WHITE POWDER
Melting Point
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
- solubility
- 1 gm · cold water: soluble1gm in 6.5ml
- pka
- -1.27 · -1.27±0.10(Predicted)
- form
- Crystalline Powder
- color
- White to light cream
- Odor
- Odorless
- Water Solubility
- soluble
- Merck
- 14 · 14,2688
- BRN
- 878221 · 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 · 107-91-5(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 38 G2YXH · YBK38G2YXH
- NIST Chemistry Reference
- 2 · Acetamide, 2-cyano-(107-91-5)
- EPA Substance Registry System
- 2 · 2-Cyanoacetamide (107-91-5)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H335
- Precautionary statements
- 261 · P261-P264-P270-P301+P312-P302+P352-P305+P351+P338
- target organs
- Respiratory system
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xn
- Risk Statements
- 22 · 22-36/37/38-20/21/22
- Safety Statements
- 22 · 22-26-28A
- RIDADR
- 3439 · UN 3439 6.1/PG 3
- WGK Germany
- 2 · 2
- RTECS
- 5950000 · AB5950000
- TSCA
- TSCA listed
- PackingGroup
- III
- HS Code
- 29159080 · 29159080
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 4 OralEye · Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
- Hazardous Substances Data
- 107 · 107-91-5(Hazardous Substances Data)
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
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
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
Safety & protection
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/
Protective Action Criteria (PAC)
0.81 [mg/m3]
8.7 [mg/m3]
52 [mg/m3]
Toxicology
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)
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)
Non-Human Toxicity Values
LD50 RATS ORAL MORE THAN 3200 MG/KG
LD50 RATS INTRAPERITONEAL MORE THAN 800 MG/KG
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
- risk_code
- 22-36/37/38-20/21/22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- safety_code
- 22-26-28A
- Storage Class
- 11 - Combustible Solids
- packing_group
- III
- target organs
- Respiratory system
- Hazard statements
- H302-H315-H319-H335
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P261-P264-P270-P301+P312-P302+P352-P305+P351+P338
- Hazardous Substances Data
- 107-91-5(Hazardous Substances Data)
Chemistry & industry
Pharmacology
Metabolism/Metabolites
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
Used in the synthesis of pharmaceuticals and plastics; [Hawley]
IN ORGANIC SYNTHESES (EG STARTING MATERIAL FOR VITAMIN B6 SYNTHESIS)
Applications
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
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.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
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
Linked notes
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