Isothiazole

Base Information

• Chemical Name: Isothiazole
• CAS No.: 288-16-4
• Molecular Formula: C3H3NS
• Molecular Weight: 85.1295
• Hs Code.: 2934999090
• European Community (EC) Number: 811-077-2
• UNII: 38FAO14250
• DSSTox Substance ID: DTXSID90182980
• Nikkaji Number: J102.085D
• Wikipedia: Isothiazole
• Wikidata: Q419746
• Metabolomics Workbench ID: 55155
• ChEMBL ID: CHEMBL2171712
• Mol file: 288-16-4.mol

Synonyms:Isothiazole;288-16-4;1,2-thiazole;2-azathiophene;C3H3NS;1,2-thiazol;UNII-38FAO14250;CHEBI:35600;38FAO14250;CHEMBL2171712;DTXSID90182980;AMY42108;BCP05147;CS-D1732;MFCD00020818;STK688931;AKOS005137880;AS-0796;SB36396;FT-0648927;I0982;EN300-67277;A23322;A819611;Q419746;J-017282

Chemical Property of Isothiazole

Chemical Property:

• Vapor Pressure: 908mmHg at 25°C
• Melting Point: 176 °C (decomp)(Solv: water (7732-18-5))
• Refractive Index: 1.542
• Boiling Point: 19.974 °C at 760 mmHg
• PKA: 4.00±0.12(Predicted)
• Flash Point: -31.787 °C
• PSA: 41.13000
• Density: 1.18 g/cm³
• LogP: 1.14310
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• Solubility.: Chloroform, Ethyl Acetate
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 84.99862027
• Heavy Atom Count: 5
• Complexity: 30.1

Purity/Quality:

99% ^*data from raw suppliers

Isothiazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Thiazoles
• Canonical SMILES: C1=CSN=C1
• Uses: Isothiazole, is a versatile building block that can be used in the synthesis of more complex compounds with biological activity such as the pharmaceutical drugs ziprasidone (Z485000), and perospirone (P288900).

Technology Process of Isothiazole

There total 1 articles about Isothiazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

2-bromo-1,3-thiazole (3034-53-5,215777-74-5) → isothiazol (288-16-4) + 1,3-thiazole (288-47-1)

Guidance literature:

In methanol; for 24h; Mechanism; Irradiation; other mono- and dibromothiazoles; var. solvents and additives;

Reference yield: 84.0%

isothiazol (288-16-4) + carbon dioxide (124-38-9,18923-20-1) → isothiazole-5-carboxylic acid (10271-85-9)

Guidance literature:

carbon dioxide; With AuOH(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene); potassium hydroxide; In tetrahydrofuran; at 20 ℃; for 0.25h; under 1125.11 Torr;

isothiazol; In tetrahydrofuran; at 20 ℃; for 12h; under 1125.11 Torr;

With hydrogenchloride; In tetrahydrofuran; water; regioselective reaction;

DOI:10.1021/ja103429q

Reference yield: 83.0%

isothiazol (288-16-4) + (triphenylphosphine)gold(I) chloride (14243-64-2) → [Au(C=CHCH=NS)(PPh3)] (167637-13-0)

Guidance literature:

With butyllithium; In tetrahydrofuran; hexane; N2-atmosphere; stirring isothiazole (in THF) with equimolar amt. of BuLi (in hexane) (45 min, -78°C), addn. of 1 equiv. Au-complex, stirring (1 h, -78°C; warming to -30°C during 2 h; 30 min, room temp.); solvent removal (vac.), dissoln. in CH2Cl2, filtration through SiO2, solvent removal, crystn. (pentane/benzene, vapour diffusion); elem. anal.;

DOI:10.1039/DT9950002067

upstream raw materials:

2-bromo-1,3-thiazole

Downstream raw materials:

(5-chloro-2-nitro-phenyl)-isothiazol-5-yl-methanol

5-Acetyl-isothiazol

2-Benzyl-isothiazolium - Bromid

(4-chloro-phenyl)-isothiazol-5-yl-methanol

Refernces