2-Bromothiophene

Base Information

• Chemical Name: 2-Bromothiophene
• CAS No.: 1003-09-4
• Molecular Formula: C4H3BrS
• Molecular Weight: 163.038
• Hs Code.: 29349990
• European Community (EC) Number: 213-699-4
• NSC Number: 4456
• UNII: GFF929NUW7
• DSSTox Substance ID: DTXSID4061389
• Nikkaji Number: J101.470F
• Wikipedia: 2-Bromothiophene
• Wikidata: Q17487944
• Mol file: 1003-09-4.mol

Synonyms:2-BROMOTHIOPHENE;1003-09-4;Thiophene, 2-bromo-;2-Thienyl bromide;Thiophene, bromo-;Bromothiophene;2-bromo-thiophene;2-bromo thiophene;GFF929NUW7;NSC 4456;NSC-4456;EINECS 213-699-4;60326-18-3;Thienyl bromide;5-bromothiophene;NSC4456;5-bromo-thiophene;2-bromanylthiophene;MFCD00005417;2-Bromothiophene, 98%;UNII-GFF929NUW7;SCHEMBL22395;BIDD:GT0231;DTXSID4061389;AMY21853;BCP21550;AC-194;AKOS000121588;CS-W020109;DS-1962;PS-5772;B0941;FT-0611618;FT-0611619;FT-0689817;EN300-20745;D77872;A800095;Q-200247;Q17487944;F0001-0036

Chemical Property of 2-Bromothiophene

Chemical Property:

• Appearance/Colour: colorless to light yellow transparent liquid
• Vapor Pressure: 4.99mmHg at 25°C
• Melting Point: -10 °C
• Refractive Index: n20/D 1.586(lit.)
• Boiling Point: 149.999 °C at 760 mmHg
• Flash Point: 47.052 °C
• PSA: 28.24000
• Density: 1.714 g/cm³
• LogP: 2.51060
• Storage Temp.: 2-8°C
• Sensitive.: Light Sensitive
• Water Solubility.: IMMISCIBLE
• XLogP3: 2.8
• 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:

99.5%min ^*data from raw suppliers

2-Bromothiophene ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Thiophenes
• Canonical SMILES: C1=CSC(=C1)Br
• Uses: 2-Bromothiophene has been used in electrochemical reduction of a number of mono- and dihalothiophenes at carbon cathodes in dimethylformamide containing tetramethylammonium per chlorate by cyclic voltammetry and controlled-potential electrolysis.

Technology Process of 2-Bromothiophene

There total 34 articles about 2-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: 94.0%

thiophene (188290-36-0,8014-23-1,25233-34-5) → 2-bromothiophene (1003-09-4)

Guidance literature:

With hydrogen bromide; dihydrogen peroxide; In diethyl ether; at 15 - 20 ℃; for 0.25h;

DOI:10.1055/s-1988-27740

Reference yield:

thiophene (188290-36-0,8014-23-1,25233-34-5) + bromocyane (506-68-3) → 2-bromothiophene (1003-09-4) + 2,5-dibromothiophen (3141-27-3)

Guidance literature:

at 45 - 50 ℃;

Reference yield:

thiophene (188290-36-0,8014-23-1,25233-34-5) + N-bromoacetamide (79-15-2) → 2-bromothiophene (1003-09-4)

Guidance literature:

upstream raw materials:

thiophene

bromocyane

N-bromoacetamide

2,5-dibromothiophen

Downstream raw materials:

2,3,4,5-tetrachlorothiophene

2,3,5-trichlorothiophene

2,2'-Bithiophene

2-thiophenone

Refernces

• 1、 Seconi, Giancarlo,Eaborn, Colin. "PROTIODESILYLATION OF SUBSTITUTED 2-TRIMETHYLSILYLTHIOPHENS". . p. 931 - 934. Retrieved 1981.
• 2、 Keegstra, M. A.,Brandsma, L.. "Convenient High-Yield Procedures for 2-Bromothiophene and 2,5-Dibromothiophene". . p. 890 - 891. Retrieved 1988.
• 3、 Muathen, Hussni A.. "Pyridinium dichlorobromate: A new stable brominating agent for aromatic compounds". . p. 169 - 171. Retrieved 2002.
• 4、 Hurd,Anderson. "-". . p. 3517. Retrieved 1953.
• 5、 Mubarak, Mohammad S.,Peters, Dennis G.. "Electrochemical reduction of mono- and dihalothiophenes at carbon cathodes in dimethylformamide. First example of an electrolytically induced halogen dance". . p. 8074 - 8078. Retrieved 1996.
• 6、 Gol'dfarb, Ya. L.,Dudinov, A. A.,Litvinov, V. P.. "NEW METHOD FOR PREPARATION OF 2-BROMOTHIOPHENE". . p. 2104 - 2105. Retrieved 1982.
• 7、 Li, Run,Wang, Zi Jun,Wang, Lei,Ma, Beatriz Chiyin,Ghasimi, Saman,Lu, Hao,Landfester, Katharina,Zhang, Kai. A. I.. "Photocatalytic Selective Bromination of Electron-Rich Aromatic Compounds Using Microporous Organic Polymers with Visible Light". . p. 1113 - 1121. Retrieved 2016.
• 8、 McKillop et al.. "-". . p. 88. Retrieved 1972.
• 9、 Canete, Alvaro F.,Salas, Cristian O.,Zacconi, Flavia C.. "Efficient indium-mediated dehalogenation of aromatics in ionic liquid media". . p. 398 - 407. Retrieved 2013.
• 10、 Collis, Gavin E.,Burrell, Anthony K.,Scott, Sonya M.,Officer, David L.. "Toward Functionalized Conducting Polymers: Synthesis and Characterization of Novel β-(Styryl)terthiophenes". . p. 8974 - 8983. Retrieved 2003.