3-Bromothiophene-2-carbonyl chloride

Base Information

• Chemical Name: 3-Bromothiophene-2-carbonyl chloride
• CAS No.: 25796-68-3
• Molecular Formula: C5H2BrClOS
• Molecular Weight: 225.493
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID00383926
• Nikkaji Number: J3.479.094I
• Wikidata: Q72513041
• Mol file: 25796-68-3.mol

Synonyms:3-bromothiophene-2-carbonyl chloride;25796-68-3;3-Bromothiophene-2-carbonylchloride;3-bromo-2-thiophenecarbonyl chloride;SCHEMBL1623886;DTXSID00383926;QMKGMTULPADQDK-UHFFFAOYSA-N;STR04738;MFCD00173836;3-Bromo-thiophene-2-carbonyl chloride;AKOS009159141;FT-0615257;A818032

Chemical Property of 3-Bromothiophene-2-carbonyl chloride

Chemical Property:

• Vapor Pressure: 0.0147mmHg at 25°C
• Melting Point: 65-68 °C
• Refractive Index: 1.618
• Boiling Point: 257.208 °C at 760 mmHg
• Flash Point: 109.356 °C
• PSA: 45.31000
• Density: 1.856 g/cm³
• LogP: 2.88960
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 223.86983
• Heavy Atom Count: 9
• Complexity: 130

Purity/Quality:

98%min ^*data from raw suppliers

3-Bromothiophene-2-carbonylchloride ^*data from reagent suppliers

Safty Information:

• Statements: 34
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CSC(=C1Br)C(=O)Cl

Technology Process of 3-Bromothiophene-2-carbonyl chloride

There total 6 articles about 3-Bromothiophene-2-carbonyl chloride 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:

3-bromo-2-thiophenecarboxaldehyde (930-96-1) → 3-bromo-thiophene-2-carbonyl chloride (25796-68-3)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. NaClO₂; NaH₂PO₄; 2-methyl-2-butene / acetone

2: (COCl)2; DMF / toluene

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; N,N-dimethyl-formamide; In acetone; toluene;

DOI:10.1055/s-2002-35577

Reference yield:

3-bromothiophene-2-carboxylic acid (7311-64-0) → 3-bromo-thiophene-2-carbonyl chloride (25796-68-3)

Guidance literature:

With thionyl chloride; In 1,4-dioxane; for 0.5h; Heating;

Reference yield:

methyl 3-bromothiophene-2-carboxylate (26137-08-6) → 3-bromo-thiophene-2-carbonyl chloride (25796-68-3)

Guidance literature:

Multi-step reaction with 2 steps

1: water / acetonitrile / Alkaline conditions; Inert atmosphere

2: thionyl chloride / Inert atmosphere

With thionyl chloride; water; In acetonitrile;

DOI:10.1016/j.tet.2013.02.069

upstream raw materials:

3-bromothiophene-2-carboxylic acid

3-bromo-2-thiophenecarboxaldehyde

methyl 3-bromothiophene-2-carboxylate

Methyl 3-aminothiophene-2-carboxylate

Downstream raw materials:

methyl 3-bromothiophene-2-carboxylate

1-(3-(4-(diethylamino)phenylamino)thiophen-2-yl)-3-phenylprop-2-yn-1-one

4,5-diphenylthieno[3,2-b]pyridin-7(4H)-one

5-Phenyl-4-p-tolylthieno[3,2-b]pyridin-7(4H)-one

Refernces

• 1、 Jin, Weiwei,Yu, Shouyun. "Photoinduced and Palladium-Catalyzed Remote Desaturation of Amide Derivatives". supporting information. p. 6931 - 6935. Retrieved 2021/09/11.
• 2、 Sun, Qi,Zhao, Mingming,Liang, Jingwei,Xiao, Junhai,Meng, Fanhao. "Design, synthesis and activity evaluation study of novel substituted N-sulfonyl homoserine lactone derivatives as bacterial quorum sensing inhibitors". . p. 3345 - 3353. Retrieved 2017/11/16.