2,5-Dibromothiophene

Base Information

• Chemical Name: 2,5-Dibromothiophene
• CAS No.: 3141-27-3
• Molecular Formula: C4H2Br2S
• Molecular Weight: 241.934
• Hs Code.: 29349990
• European Community (EC) Number: 221-547-3
• NSC Number: 4488
• UNII: F0033K8CXM
• DSSTox Substance ID: DTXSID3062863
• Nikkaji Number: J25.468A
• Wikidata: Q27277452
• Mol file: 3141-27-3.mol

Synonyms:2,5-DIBROMOTHIOPHENE;3141-27-3;Thiophene, 2,5-dibromo-;2,5-dibromo-thiophene;UNII-F0033K8CXM;F0033K8CXM;NSC 4488;NSC-4488;EINECS 221-547-3;AI3-08106;NSC4488;MFCD00005420;Thiophene,5-dibromo-;2,5-bis(bromanyl)thiophene;2,5-Dibromothiophene, 95%;BIDD:GT0086;SCHEMBL147222;DTXSID3062863;CS-D1412;AKOS000119947;AC-4901;PS-7567;A5692;AM20090448;D1549;FT-0610283;EN300-19548;4,4-DIAMINOSTILBENE-2,2-DISULFONICACID;D71235;A820842;Q-101192;2,5-Dibromothiophene, Vetec(TM) reagent grade, 94%;Q27277452;73061-85-5

Chemical Property of 2,5-Dibromothiophene

Chemical Property:

• Appearance/Colour: light yellow liquid
• Vapor Pressure: 0.292mmHg at 25°C
• Melting Point: -6 °C
• Refractive Index: 1.627-1.63
• Boiling Point: 209.5 °C at 760 mmHg
• Flash Point: 99.4 °C
• PSA: 28.24000
• Density: 2.174 g/cm³
• LogP: 3.27310
• Storage Temp.: 0-6°C
• Solubility.: Chloroform, Methanol
• Water Solubility.: practically insoluble
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 241.82235
• Heavy Atom Count: 7
• Complexity: 58.7

Purity/Quality:

99% ^*data from raw suppliers

2,5-Dibromothiophene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+,Xi
• Hazard Codes: T+,Xi
• Statements: 68-43-36/37/38-28-20/21
• Safety Statements: 45-36/37/39-28A-26-36

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Thiophenes
• Canonical SMILES: C1=C(SC(=C1)Br)Br
• Uses: 2,5-Dibromothiophene, is mainly used as pharmaceutical intermediate and synthesis intermediate. 2,5-Dibromothiophene was used as starting reagent for the synthesis of α,α′-didecylquater-, -quinque- and -sexi-thiophenes. It was used in the preparation of soluble α,ω-diformyl-a-oligothiophenes.

Technology Process of 2,5-Dibromothiophene

There total 22 articles about 2,5-Dibromothiophene 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%

thiophene (188290-36-0,8014-23-1,25233-34-5) → 2,5-dibromothiophen (3141-27-3)

Guidance literature:

With N-Bromosuccinimide; In ethyl acetate; at 20 ℃; for 0.166667h; Ultrasonic irradiation;

DOI:10.1016/j.tetlet.2009.10.133

Reference yield: 98.0%

2-bromothiophene (1003-09-4) → 2,5-dibromothiophen (3141-27-3)

Guidance literature:

With N-Bromosuccinimide; perchloric acid; In tetrachloromethane; for 24h; Ambient temperature;

DOI:10.1021/jo00063a028

Reference yield: 92.0%

5-bromothiophene-2-carboxylic acid (7311-63-9) → 2,5-dibromothiophen (3141-27-3)

Guidance literature:

With potassium phosphate; tetrabuthylammonium tribromide; In acetonitrile; at 100 ℃;

DOI:10.1039/c8sc01016a

upstream raw materials:

thiophene

bromocyane

N-bromoacetamide

2-bromothiophene

Downstream raw materials:

2-bromo-5-trimethylsilylthiophene

2-Acetyl-5-bromothiophene

2-(5-bromo-[2]thienyl)-2-hydroxy-1,2-diphenyl-ethanone

5-bromo-2-thiophencarboxaldehyde

Refernces

• 1、 Ponomarenko,Muzafarov,Borshchev,Vodopyanov,Demchenko,Myakushev. "Synthesis of bithiophenesilane dendrimer of the first generation". . p. 684 - 690. Retrieved 2005.
• 2、 Calamante, Massimo,Coppola, Carmen,Dessì, Alessio,Franchi, Daniele,Goti, Giulio,Mordini, Alessandro,Reginato, Gianna,Sinicropi, Adalgisa,Zani, Lorenzo. "Donor-Acceptor-Donor Thienopyrazine-Based Dyes as NIR-Emitting AIEgens". . p. 2655 - 2664. Retrieved 2021/06/26.
• 3、 Roy, Sourav Saha,Chowdhury, Sabyasachi Roy,Mishra, Sabyashachi,Patra, Sanjib K.. "Role of Substituents at 3-position of Thienylethynyl Spacer on Electronic Properties in Diruthenium(II) Organometallic Wire-like Complexes". supporting information. p. 3304 - 3313. Retrieved 2020/09/09.