Basic information
- CAS
1189-71-5- Standard SMILES
O=C=NS(=O)(=O)Cl- InChIKey
WRJWRGBVPUUDLA-UHFFFAOYSA-N- Molecular formula
- CClNO3S
- Average molar mass
- 141.53 g/mol
- Monoisotopic mass
- 140.92874154
Overview
Chlorosulfonyl isocyanate, also known as CSI, is a chemical compound of cyanide. It is used in organic synthesis for purposes such as the preparation of medically important preparation of beta-lactams. (L573)
Names & identifiers
- Preferred name
- Chlorosulfonyl isocyanate
- IUPAC
- N-(oxomethylidene)sulfamoyl chloride
- English name
- Chlorosulfonyl isocyanate
- Molecular formula
- CClNO3S
- Molecular weight
- 141.53
Names & synonyms
Show more names
Database identifiers
- CAS
1189-71-5- PubChem CID
- 70918
- DTXSID
DTXSID0061585- UNII
- 2903Y990SM
- EC Number
- 214-715-2
- Nikkaji
- J111.247C
Properties
Computed structural properties
- XLogP
- 1.5
- Topological polar surface area
- 72 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 1
- Heavy atoms
- 7
- Formal charge
- 0
- Complexity
- 181
Experimental & physicochemical properties
Physicochemical properties
- Melting point
- -44 °C · -44 °C (lit.)
- Boiling point
- 107 °C · 107 °C (lit.)
- Density
- 1.626 g/mL · 1.626 g/mL at 25 °C (lit.)
- vapor pressure
- 5.57 psi · 5.57 psi ( 20 °C)
- refractive index
- 20 · n20/D 1.447(lit.)
- Flash point
- 110 °C · >110°C
- storage temp.
- 2 · 2-8°C
- solubility
- Chloroform (Slightly, Heated)
- form
- Crystals, Crystalline Powder or Granules
- Specific Gravity
- 1.626 · 1.626 (20℃)
- color
- White
- Water Solubility
- reacts violently exothermic
- BRN
- 1237247 · 1237247
- InChI
- 1S/CClNO3S/c2-7(5,6)3-1-4
- InChIKey
- WRJWRGBVPUUDLA-UHFFFAOYSA-N
- SMILES
- ClS(=O)(=O)N=C=O
- CAS DataBase Reference
- 1189 · 1189-71-5(CAS DataBase Reference)
- FDA UNII
- 2903 Y990SM · 2903Y990SM
- EPA Substance Registry System
- Sulfuryl chloride isocyanate (1189-71-5)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 5 · GHS05,GHS07,GHS08
- Signal word
- Danger
- Hazard statements
- 302 · H302-H314-H317-H334
- Precautionary statements
- 261 · P261-P280-P301+P312-P303+P361+P353-P304+P340+P310-P305+P351+P338
- PPE
- Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
- Hazard Codes
- C
- Risk Statements
- 14 · 14-22-34-42-20/22
- Safety Statements
- 23 · 23-26-30-36/37/39-45
- RIDADR
- 3265 · UN 3265 8/PG 2
- WGK Germany
- 3 · 3
- F
- 10 · 10-21-19
- TSCA
- TSCA listed
- HazardClass
- 8 · 8
- PackingGroup
- II
- HS Code
- 28510080 · 28510080
- Storage Class
- 8 A · 8A - Combustible corrosive hazardous materials
- Hazard Classifications
- 4 OralEye · Acute Tox. 4 OralEye Dam. 1Resp. Sens. 1Skin Corr. 1BSkin Sens. 1
- Toxicity
- 50 orally · LD50 orally in Rabbit: 640 mg/kg
- REACH Registrations
- Active
- Limited Quantities
- 1 Kg · 1 Kg (2.2 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
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, P320, 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 88 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Sulfuryl chloride isocyanate
Status: Active Update: 28-11-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/10803
Chlorosulphonyl isocyanate: Does not have an individual approval but may be used under an appropriate group standard
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
- F
- 10-21-19
- PPE
- Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
- wgk
- 3
- tsca
- TSCA listed
- ridadr
- UN 3265 8/PG 2
- hs_code
- 28510080
- Toxicity
- LD50 orally in Rabbit: 640 mg/kg
- risk_code
- 14-22-34-42-20/22
- Signal word
- Danger
- Symbol(GHS)
- GHS05,GHS07,GHS08
- hazard_code
- C
- safety_code
- 23-26-30-36/37/39-45
- hazard_class
- 8
- Storage Class
- 8A - Combustible corrosive hazardous materials
- packing_group
- II
- Hazard statements
- H302-H314-H317-H334
- Limited Quantities
- 1 Kg (2.2 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 4 OralEye Dam. 1Resp. Sens. 1Skin Corr. 1BSkin Sens. 1
- Precautionary statements
- P261-P280-P301+P312-P303+P361+P353-P304+P340+P310-P305+P351+P338
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)
Uses & manufacturing
Applications
UsesChlorosulfonyl isocyanate, a highly reactive chemical for chemical synthesis, is used as an intermediate used for production of antibiotics (Cefuroxime, penems), polymers as well as agrochemicals. Product Data Sheet
UsesEmployed in a regio- and diastereoselective introduction of a protected amino group in a synthesis of chiral, polyhydroxylated piperidines. Generation of ureas from amino groups in a synthesis of benzimidazolones.
General DescriptionChlorosulfonyl isocyanate reacts with hydrocarbon alkenes via stepwise dipolar pathway to give N-chlorosulfonyl-β-lactams.
Upstream & downstream products
Downstream products
Suppliers100 total
Related reactions
Compound notes
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