3-Bromothiophene

Base Information

• Chemical Name: 3-Bromothiophene
• CAS No.: 872-31-1
• Molecular Formula: C4H3BrS
• Molecular Weight: 163.038
• Hs Code.: 2934.99
• European Community (EC) Number: 212-821-3
• NSC Number: 96612
• UNII: G818Z74YV0
• DSSTox Substance ID: DTXSID2022129
• Nikkaji Number: J25.465G
• Wikipedia: 3-Bromothiophene
• Wikidata: Q927001
• Mol file: 872-31-1.mol

Synonyms:3-BROMOTHIOPHENE;872-31-1;Thiophene, 3-bromo-;3-Thienyl bromide;3-Bromothiofuran;3-bromo-thiophene;beta-Bromothiophene;.beta.-Bromothiophene;C4H3BrS;EINECS 212-821-3;NSC 96612;3-BROMO THIOPHENE;G818Z74YV0;NSC-96612;3-bromothiphene;3-bromthiophene;NSC96612;MFCD00005464;3-Bromothiophene, 97%;SCHEMBL7276;BIDD:GT0802;UNII-G818Z74YV0;DTXSID2022129;AKOS005257789;AC-4899;AM81213;CS-W009226;PB48063;PS-5773;LS-184900;B1067;FT-0600846;EN300-36196;A19254;P20051;Q927001;Q-101190;W-204354;F0001-2168;84928-93-8

Chemical Property of 3-Bromothiophene

Chemical Property:

• Appearance/Colour: clear to pale yellow liquid
• Vapor Pressure: 3.41mmHg at 25°C
• Melting Point: <-10 °C
• Refractive Index: 1.5863
• Boiling Point: 158.4 °C at 760 mmHg
• Flash Point: 56.7 °C
• PSA: 28.24000
• Density: 1.714 g/cm³
• LogP: 2.51060
• Storage Temp.: 0-6°C
• Sensitive.: Light Sensitive/Stench
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: IMMISCIBLE
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 161.91388
• Heavy Atom Count: 6
• Complexity: 46.8

Purity/Quality:

98% ^*data from raw suppliers

3-Bromothiofuran ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,N
• Hazard Codes: T,Xi,N,Xn
• Statements: 10-25-41-51/53-36/37/38-23/24/25-20/21/22-43-36/37
• Safety Statements: 26-36/37/39-45-61-38-28A-16-24/25-23-36-36/37-24/35

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CSC=C1Br
• Uses: 3-Bromothiophene is used in the preparation of derivatives such as thienylenic alpha, μ-diformyl-alpha-oligothiophenes and 3-lithiothiophene. It is also used in the synthesis of 3-lithiothiophene by reacting with n-butyllithium. 3-Bromothiophene can be used as a reactant to synthesize:3,3-Bithiophene via borylation followed by Suzuki coupling.3-Alkylthiophenes by NiDPPP++ catalyzed cross-coupling with Grignard reagents.3-Lithiothiophene by treating with n-butyllithium in hexane.Derivatives of thienylenic α, ω?diformyl?α?oligothiophenes.N-(2-(3-bromothiophen-2-yl)phenyl)methanesulfonamides by coupling at the 2-position with N-arylmethanesulfonamides, mediated by iodobenzene diacetate (178721).

Technology Process of 3-Bromothiophene

There total 38 articles about 3-Bromothiophene 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: 98.0%

2,3-dibromothiophen (3140-93-0) → 3-Bromothiophene (872-31-1)

Guidance literature:

With dibutylbis(cyclopentadienyl)zirconium; at 0 ℃; for 3h;

DOI:10.1246/cl.1997.1251

Reference yield: 90.0%

2,3,5-tribromothiophene (3141-24-0) → 3-Bromothiophene (872-31-1)

Guidance literature:

With acetic acid; zinc; In water; for 3h; Reflux;

DOI:10.1002/cjoc.201400077

Reference yield: 82.0%

Tetrabromothiophene (3958-03-0) → 3-Bromothiophene (872-31-1)

Guidance literature:

With hydrogen bromide; lead acetate; In methanol; electrolysis;

DOI:10.1055/s-1990-26887

upstream raw materials:

2,3-dibromothiophen

2,3,5-tribromothiophene

n-butyllithium

diethyl ether

Downstream raw materials:

3-(2-hydroxyethyl)thiophene

3-bromothiophene-2-carboxylic acid

3-Thiophene carboxylic acid

3-(methylthio)thiophene

Refernces

• 1、 Olivares, Astrid M.,Weix, Daniel J.. "Multimetallic Ni- and Pd-Catalyzed Cross-Electrophile Coupling to Form Highly Substituted 1,3-Dienes". supporting information. p. 2446 - 2449. Retrieved 2018/02/28.
• 2、 He, Lu-Ying,Urrego-Riveros, Sara,Gates, Paul J.,N?ther, Christian,Brinkmann, Maren,Abetz, Volker,Staubitz, Anne. "Synthesis of poly(thiophene-alt-pyrrole) from a difunctionalized thienylpyrrole by Kumada polycondensation". supporting information. p. 5399 - 5406. Retrieved 2015/07/15.