Basic information
- Standard SMILES
N=C=O- InChIKey
OWIKHYCFFJSOEH-UHFFFAOYSA-N- Molecular formula
- CHNO
- Average molar mass
- 43.025 g/mol
- Monoisotopic mass
- 43.00581365
Overview
Isocyanic acid is a colourless, volatile, poisonous inorganic compound with the formula HNCO; the simplest stable chemical compound that contains carbon, hydrogen, nitrogen, and oxygen, the four most commonly-found elements in organic chemistry and biology. It is a hydracid and a one-carbon compound. It is a conjugate acid of a cyanate. It is a tautomer of a cyanic acid.
Names & identifiers
- Preferred name
- Isocyanic acid
- IUPAC
- isocyanic acid
- English name
- Isocyanic acid
- Molecular formula
- CHNO
- Molecular weight
- 43.02
Names & synonyms
Show more names
Database identifiers
- CAS
75-13-8- PubChem CID
- 6347
- DTXSID
DTXSID9073884- ChEBI
CHEBI:29202- UNII
- QKG6U31925
- EC Number
- 616-189-3
- Nikkaji
- J9.226F
Properties
Computed structural properties
- XLogP
- 1
- Topological polar surface area
- 40.9 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 0
- Heavy atoms
- 3
- Formal charge
- 0
- Complexity
- 27.8
Experimental & physicochemical properties
Physicochemical properties
- Melting point
- -86 °C · -86 °C
- Boiling point
- 41.91 °C · 41.91°C (rough estimate)
- Density
- 1.04 · 1.04±0.1 g/cm3(Predicted)
- refractive index
- 1.43 · 1.4300 (estimate)
- PH
- 3.35 · 3.35(1 mM solution);2.76(10 mM solution);2.23(100 mM solution)
- Specific Heat Capacity
- 1.04 J/ · Cp(gas): 1.04 J/(g·K), at 25℃
- Henry's Law Constant
- 2 · 2.0×10-1 mol/(m3Pa) at 25℃, Roberts and Liu (2019)
- InChI
- InChI=1S/CHNO/c2-1-3/h2H
- InChIKey
- OWIKHYCFFJSOEH-UHFFFAOYSA-N
- SMILES
- N=C=O
- FDA UNII
- 6 U31925 · QKG6U31925
- EPA Substance Registry System
- Isocyanic acid (75-13-8)
- Symbol(GHS)
- 8 · GHS08,GHS07,GHS05
- Signal word
- Danger
- Hazard statements
- 314 · H314-H335-H332-H302-H312-H334
- Precautionary statements
- 264 · P264-P270-P301+P312-P330-P501-P260-P264-P280-P301+P330+P331-P303+P361+P353-P363-P304+P340-P310-P321-P305+P351+P338-P405-P501-P280-P302+P352-P312-P322-P363-P501-P261-P285-P304+P341-P342+P311-P501-P261-P271-P304+P340-P312
Safety & regulation
GHS classification
GHS Classification
Danger
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P233, P260, P261, P264, P270, P271, P280, P284, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P319, P321, P330, P342+P316, P362+P364, P363, P403, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 38 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Safety & protection
Protective Action Criteria (PAC)
2.0 [ppm]
7.1 [ppm]
15 [ppm]
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
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)
Safety data
- Signal word
- Danger
- Symbol(GHS)
- GHS08,GHS07,GHS05
- Hazard statements
- H314-H335-H332-H302-H312-H334
- Precautionary statements
- P264-P270-P301+P312-P330-P501-P260-P264-P280-P301+P330+P331-P303+P361+P353-P363-P304+P340-P310-P321-P305+P351+P338-P405-P501-P280-P302+P352-P312-P322-P363-P501-P261-P285-P304+P341-P342+P311-P501-P261-P271-P304+P340-P312
Chemistry & industry
Pharmacology
Metabolism/Metabolites
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)
Applications
UsesThe primary use of methyl isocyanate (MIC, CAS no. 624-83-9) is as a chemical intermediate in the production of carbamate pesticides. MIC is also used to produce polyurethane foam and plastics (ATSDR, 2002). Isocyanic acid (ICA, Cas no. 75-13- 8) does not have commercial uses because of its instability. The potential for occupational exposure to ICA largely arises when it is generated as a thermal degradation product of other industrial processes. Ethyl isocyanate is a liquid used commercially to make pharmaceuticals and pesticides (NJDHSS, 2000). Phenyl isocyanate (PIC, CAS no. 103-71-9) is a trace constituent in commercial diphenyl methane diisocyanate products.
Preparation methods
PreparationIsocyanic acid was prepared in pure form by reaction of KOCN or NaOCN with stearic or oxalic acid in good yield.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
Additional notes
DefinitionChEBI: A colourless, volatile, poisonous inorganic compound with the formula HNCO; the simplest stable chemical compound that contains carbon, hydrogen, nitrogen, and oxygen, the four most commonly-found elements in organic chemistry and biology.
Related reactions
Linked notes
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