2-Bromo-3-(bromomethyl)thiophene

Base Information

• Chemical Name: 2-Bromo-3-(bromomethyl)thiophene
• CAS No.: 40032-76-6
• Molecular Formula: C5H4 Br2 S
• Molecular Weight: 255.961
• Hs Code.: 2934999090
• European Community (EC) Number: 626-783-4
• DSSTox Substance ID: DTXSID80370778
• Nikkaji Number: J3.392.491G
• Wikidata: Q72452135
• Mol file: 40032-76-6.mol

Synonyms:2-bromo-3-(bromomethyl)thiophene;40032-76-6;2-Bromo-3-bromomethylthiophene;Thiophene, 2-bromo-3-(bromomethyl)-;MFCD02180908;SCHEMBL725380;3-bromomethyl-2-bromothiophene;DTXSID80370778;ZPWPMAAPQZXPDD-UHFFFAOYSA-N;AMY42046;2-Bromo-3-(Bromomethyl) Thiophene;AKOS015835995;PB14291;2-Bromo-3-(bromomethyl)thiophene, 96%;AC-29747;AS-36532;SY041583;A6690;FT-0649277;EN300-198005;Q-102489

Chemical Property of 2-Bromo-3-(bromomethyl)thiophene

Chemical Property:

• Vapor Pressure: 0.0289mmHg at 25°C
• Refractive Index: n20/D 1.638
• Boiling Point: 70-76/0.8mm
• Flash Point: 110 ºC
• PSA: 28.24000
• Density: 1.967
• LogP: 3.40550
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 255.83800
• Heavy Atom Count: 8
• Complexity: 76.8

Purity/Quality:

97% ^*data from raw suppliers

2-Bromo-3-(bromomethyl)thiophene ^*data from reagent suppliers

Safty Information:

• Hazard Codes: C,Xn
• Statements: 20/21/22-36/37/38-41-37/38-22-34
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CSC(=C1CBr)Br

Technology Process of 2-Bromo-3-(bromomethyl)thiophene

There total 7 articles about 2-Bromo-3-(bromomethyl)thiophene 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-bromo-3-methylbenzothiophene (5381-23-7) → 2-bromo-3-(bromomethyl)thiophene (40032-76-6)

Guidance literature:

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; for 0.5h; Reflux;

DOI:10.1021/acs.orglett.0c01043

Reference yield: 87.0%

2-bromo-3-methylthiophene (14282-76-9) → 2-bromo-3-(bromomethyl)thiophene (40032-76-6)

Guidance literature:

With N-Bromosuccinimide; dibenzoyl peroxide; In Carbon tetrachloride; for 8h; Reflux;

DOI:10.1021/acs.joc.6b01922

Reference yield: 82.0%

3-Bromomethylthiophene (34846-44-1) → 2-bromo-3-(bromomethyl)thiophene (40032-76-6)

Guidance literature:

With N-Bromosuccinimide; In chloroform; acetic acid; Ambient temperature;

DOI:10.1016/S0960-894X(97)00132-7

upstream raw materials:

2-bromo-3-methylthiophene

3-Methylthiophene

3-Bromomethylthiophene

3-hydroxymethyl-thiophene

Downstream raw materials:

2-bromo-3-(2,5,8-trioxanonyl)thiophene

[(2-bromo-3-thienyl)methyl]triphenylphosphonium bromide

2-bromothiophene-3-carbaldehyde

2-Bromo-3-(2,4,6-trimethyl-phenoxymethyl)-thiophene

Refernces

Heteroaryl radicals: A furyl radical in the synthesis of the tricyclic framework of eremophilane sesquiterpenoids

10.1055/s-2005-871925

The research investigates the intramolecular addition of thieno and furan radicals to alkenyl groups, resulting in the formation of a linearly annulated tricyclic moiety through a 6-endo-trig selective cyclization process. Key chemicals involved in the study include 2-bromo-3-bromomethyl thiophene derivatives, which serve as radical precursors. The desired alkene 6 is derived from Hagemann’s ester 1 through a series of reactions involving t-BuOK, KOH, Me2CuLi, and Ph3P+CH3I–. The radical cyclization of 6 in refluxing benzene with Bu3SnH and a catalytic amount of AIBN yields 5,5-dimethyl-4,4a,5,6,7,8,8a,9-octahydro-naphtho[2,3-b]thiophene (7). For furan derivatives, 3-bromo-2-chloromethylfuran is used to synthesize compound 9, which is then converted to 2-(3-bromofuran-2-ylmethyl)-3-methylcyclohex-2-enone (10) and further to 3-bromo-2-(2,2-dimethyl-6-methylenecyclohexylmethyl)furan (12). The radical cyclization of 12 with Bu3SnH and AIBN results in the formation of 8,8-dimethyl-4,4a,5,6,7,8,8a,9-octahydronaphtho[2,3b]furan (13). The study demonstrates the potential of using radical reactions to synthesize tricyclic frameworks, particularly for furanoeremophilane sesquiterpenoids, and explores the general applicability of this approach for creating new ring-fused heterocyclic structures.