Methyl 3-chlorosulfonylthiophene-2-carboxylate

Base Information

• Chemical Name: Methyl 3-chlorosulfonylthiophene-2-carboxylate
• CAS No.: 59337-92-7
• Molecular Formula: C6H5ClO4S2
• Molecular Weight: 240.688
• Hs Code.: 29349990
• European Community (EC) Number: 920-766-8,627-732-9
• DSSTox Substance ID: DTXSID90886355
• Nikkaji Number: J1.900.857F
• Wikidata: Q72489487
• Mol file: 59337-92-7.mol

Synonyms:2-(Carbomethoxy)thiophene-3-sulfonylchloride;2-Methoxycarbonyl-3-thiophenesulfonyl chloride;3-(Chlorosulfonyl)-2-(methoxycarbonyl)thiophene;3-Chlorosulfonylthiophene-2-carboxylic acid methyl ester;Methyl3-(chlorosulfonyl)-2-thiophenecarboxylate;2-thiophenecarboxylic acid, 3-(chlorosulfonyl)-, methyl ester;Methyl 3-(chlorosulfonyl)-2-thiophenecarboxylate;

Chemical Property of Methyl 3-chlorosulfonylthiophene-2-carboxylate

Chemical Property:

• Vapor Pressure: 1.65E-05mmHg at 25°C
• Melting Point: 61-64 °C(lit.)
• Refractive Index: 1.56
• Boiling Point: 364.8 °C at 760 mmHg
• Flash Point: 174.4 °C
• PSA: 97.06000
• Density: 1.568 g/cm³
• LogP: 2.54300
• Storage Temp.: 2-8°C
• Solubility.: soluble in Toluene
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 239.9317787
• Heavy Atom Count: 13
• Complexity: 294

Purity/Quality:

99% ^*data from raw suppliers

Methyl 3-chlorosulfonylthiophene-2-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C, Xi
• Hazard Codes: C,Xi
• Statements: 34
• Safety Statements: 26-27-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=C(C=CS1)S(=O)(=O)Cl

Technology Process of Methyl 3-chlorosulfonylthiophene-2-carboxylate

There total 8 articles about Methyl 3-chlorosulfonylthiophene-2-carboxylate 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: 95.0%

methanol (67-56-1) + 3-chlorosulfonyl-thiophene-2-carboxylic acid chloride (59337-91-6) → 2-(carbomethoxy)thiophene-3-sulfonyl chloride (59337-92-7)

Guidance literature:

In chloroform; for 3h; Heating;

DOI:10.1021/jm00387a017

Reference yield: 69.0%

Methyl 3-aminothiophene-2-carboxylate (22288-78-4) → 2-(carbomethoxy)thiophene-3-sulfonyl chloride (59337-92-7)

Guidance literature:

Methyl 3-aminothiophene-2-carboxylate; With tris(bipyridine)ruthenium(II) dichloride hexahydrate; isopentyl nitrite; In acetonitrile; at 20 ℃; for 0.0833333h; Sealed tube;

With thionyl chloride; In water; acetonitrile; at 20 ℃; for 20h; Irradiation;

DOI:10.1002/cssc.201601293

Reference yield: 69.0%

2-(methoxycarbonyl)thiophene-3-diazonium tetrafluoroborate → 2-(carbomethoxy)thiophene-3-sulfonyl chloride (59337-92-7)

Guidance literature:

With thionyl chloride; tris(bipyridine)ruthenium(II) dichloride hexahydrate; In water; acetonitrile; at 20 ℃; for 20h; Sealed tube; Irradiation;

DOI:10.1002/cssc.201601293

upstream raw materials:

methanol

3-chlorosulfonyl-thiophene-2-carboxylic acid chloride

Methyl 3-aminothiophene-2-carboxylate

3-chlorothiophene-2-carboxylic acid

Downstream raw materials:

3-(3-carboxyphenylsulfamoyl)thiophene-2-carboxylic acid methyl ester

3-nitrothiophene-2-carboxylic acid

methyl 3-[(4-{4-[((2R)-2-hydroxy-2-{4-hydroxy-3-[(methylsulfonyl)amino]phenyl}ethyl)amino]-1-piperidinyl}anilino)sulfonyl]-2-thiophenecarboxylate

Refernces

• 1、 Májek, Michal,Neumeier, Michael,Jacobi von Wangelin, Axel. "Aromatic Chlorosulfonylation by Photoredox Catalysis". . p. 151 - 155. Retrieved 2017/01/17.
• 2、 Bastide,Badon,Cambon,Vega. "Transformation rates of ortho-substituted thiophene and benzene carboxylic esters: Application to thifensulfuron-methyl and metsulfuron-methyl herbicides". . p. 293 - 297. Retrieved 2007/10/03.