2,4-Dibromothiophene

Base Information

• Chemical Name: 2,4-Dibromothiophene
• CAS No.: 3140-92-9
• Molecular Formula: C4H2Br2S
• Molecular Weight: 241.934
• Hs Code.: 29349990
• European Community (EC) Number: 678-717-9
• DSSTox Substance ID: DTXSID20185323
• Nikkaji Number: J80.646C
• Wikidata: Q72465142
• Mol file: 3140-92-9.mol

Synonyms:2,4-Dibromothiophene;3140-92-9;Thiophene, 2,4-dibromo-;MFCD00043889;C4H2Br2S;2,4-DIBROMO THIOPHENE;2,4 dibromothiophene;SCHEMBL422305;AMY2556;DTXSID20185323;WAQFYSJKIRRXLP-UHFFFAOYSA-N;CS-M0432;BBL103778;STL557588;AKOS005216735;PS-3361;SB67022;SY031539;A5690;D4146;FT-0609994;EN300-83781;J-507107;InChI=1/C4H2Br2S/c5-3-1-4(6)7-2-3/h1-2;Z1245646694

Chemical Property of 2,4-Dibromothiophene

Chemical Property:

• Appearance/Colour: clear colorless to light brown liquid
• Vapor Pressure: 0.24mmHg at 25°C
• Melting Point: -26.3°C
• Refractive Index: 1.631-1.633
• Boiling Point: 213.4 °C at 760 mmHg
• Flash Point: 82.9 °C
• PSA: 28.24000
• Density: 2.174 g/cm³
• LogP: 3.27310
• Storage Temp.: 0-10°C
• Water Solubility.: It is insoluble in water.
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 241.82235
• Heavy Atom Count: 7
• Complexity: 66.7

Purity/Quality:

99% ^*data from raw suppliers

2,4-Dibromothiophene >90.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi,T
• Statements: 36/37/38-20/21/22-41-37/38-25
• Safety Statements: 36/37/39-26-36-45-39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(SC=C1Br)Br
• Uses: 2,4-Dibromothiophene is used as an important raw material and intermediate used in organic Synthesis, pharmaceuticals, agrochemicals and dyestuff. It is also used as an intermediate in organic synthesis.

Technology Process of 2,4-Dibromothiophene

There total 6 articles about 2,4-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: 17.0%

2,3,5-tribromothiophene (3141-24-0) + thiophen-2-yl magnesium bromide (5713-61-1) → 2,4-dibromothiophene (3140-92-9) + 4,5-dibromo-2,2'-bithiophene (1006384-44-6) + 2,2'-Bithiophene (492-97-7) + 3′-bromo-2,2′:5′,2″-terthiophene (105125-00-6)

Guidance literature:

With bis(triphenylphosphine)nickel(II) chloride; In tetrahydrofuran; at 20 ℃; regioselective reaction;

DOI:10.1002/ejoc.200701148

Reference yield: 8.0%

2,5-dibromothiophen (3141-27-3) + benzaldehyde (100-52-7) → 2,4-dibromothiophene (3140-92-9) + 2,5-dibromo-α-phenyl-3-thiophenemethanol (941609-28-5) + 3,5-dibromo-α-phenyl-2-thiophenemethanol

Guidance literature:

2,5-dibromothiophen; With lithium diisopropyl amide; In tetrahydrofuran; at 0 ℃; Flow reactor; Inert atmosphere;

benzaldehyde; In tetrahydrofuran; at 0 ℃; Flow reactor; Inert atmosphere;

DOI:10.1055/s-0040-1706479

Reference yield:

2,3,5-tribromothiophene (3141-24-0) → 3-Bromothiophene (872-31-1) + 2,3-dibromothiophen (3140-93-0) + 2,4-dibromothiophene (3140-92-9)

Guidance literature:

With sodium tetrahydroborate; In dimethyl sulfoxide; at 26 ℃; for 4h; Product distribution; Mechanism; other catalysts, var. solvent;

upstream raw materials:

2,3,5-tribromothiophene

ethylmagnesium bromide

thiophen-2-yl magnesium bromide

para-iodoanisole

Downstream raw materials:

4-bromo-thiophene-2-carboxylic acid

3,5-dibromothiophene-2-carboxylic acid

1-(3,5-dibromo-[2]thienyl)-ethanone

4-Bromothiophen-2-aldehyde

Refernces

• 1、 Okano, Kentaro,Yamane, Yoshiki,Nagaki, Aiichiro,Mori, Atsunori. "Trapping of Transient Thienyllithiums Generated by Deprotonation of 2,3-or 2,5-Dibromothiophene in a Flow Microreactor". supporting information. p. 1913 - 1918. Retrieved 2020/11/10.
• 2、 Amb, Chad M.,Rasmussen, Seth C.. "Sterics versus electronics: Regioselective cross-coupling of polybrominated thiophenes". body text. p. 801 - 804. Retrieved 2009/04/11.