Methyl isocyanide

HCID 11646

Basic information

CAS
593-75-9
Standard SMILES
[C-]#[N+]C
InChIKey
ZRKSVHFXTRFQFL-UHFFFAOYSA-N
Molecular formula
C2H3N
Average molar mass
41.05 g/mol
Monoisotopic mass
41.0265491

Overview

Isocyanomethane is an isocyanide.

Names & identifiers

Preferred name
Methyl isocyanide
IUPAC
isocyanomethane
English name
METHYL ISOCYANIDE
Molecular formula
C2H3N
Molecular weight
41.05

Names & synonyms

IsocyanomethaneMETHYL ISOCYANIDE593-75-9Methyl isonitrileMethylisonitrileMethane, isocyano-B5B6DXM7GGCNMeMeNCCH3-NCDTXSID3075040CHEBI:44177
Show more names
CH3NCMETHANE,ISOCYANO
RefChem:149233DTXCID9042598209-806-9isoacetonitrileMFCD05864413Isoacetonitrile; Methyl IsonitrilemethylisocyanideEINECS 209-806-9

Database identifiers

CAS
593-75-9
PubChem CID
11646
DTXSID
DTXSID3075040
ChEBI
CHEBI:44177
UNII
B5B6DXM7GG
EC Number
209-806-9
Nikkaji
J2.698K

Properties

Computed structural properties

XLogP
0
Topological polar surface area
4.4 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
1
Rotatable bonds
0
Heavy atoms
3

Experimental & physicochemical properties

SpringerMaterials PropertiesSchoenflies notation

Physicochemical properties

Melting point
-45 °C · -45°C
Boiling point
81.65 °C · 81.65°C (estimate)
Density
0.7424 · 0.7424
refractive index
1.3427 · 1.3427
storage temp.
Refrigerator, Under inert atmosphere
solubility
Chloroform (Soluble), Methanol (Slightly)

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H302 (95%): Harmful if swallowed [Warning Acute toxicity, oral]

P260, P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P319, P321, P330, P362+P364, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 40 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (95%)

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)

Exposure RoutesOral (L96) ; inhalation (L96) ; dermal (L96)
Toxicity Summary · 1 item

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)
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Safety data

ridadr
UN2929
Signal word
Warning
Symbol(GHS)
GHS08,GHS07
hazard_class
6.1, 3
Hazard statements
H373-H332-H302-H312
Limited Quantities
100ml (liquid) or 0.5 Kg (solid)

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 1 item

Cyanide is rapidly alsorbed through oral, inhalation, and dermal routes 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

UsesMethyl isocyanide is used for the preparation of various heterocycles. It is also a ligand in organometallic chemistry. (L556)

Applications

UsesIsocyanomethane can be used as porous embolization microspheres comprising drugs.

Suppliers9 total

艾吉析科技(上海)有限公司17717235263 · [email protected]
江苏艾康生物医药研发有限公司025-025-66113011 15955137747 · [email protected]
上海迈瑞尔生化科技有限公司4006356688 18621169109 · [email protected]
上海皓鸿生物医药科技有限公司400-8210725 4008210725 · [email protected]
韶远科技(上海)有限公司021-50795510 4000665055 · [email protected]

Additional notes

DefinitionChEBI: Isocyanomethane is an isocyanide.

Related reactions

31 records

Compound notes

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