3,5-Dibromo-2-methylthiophene

Base Information

• Chemical Name: 3,5-Dibromo-2-methylthiophene
• CAS No.: 29421-73-6
• Molecular Formula: C5H4Br2S
• Molecular Weight: 255.961
• Hs Code.: 2934999090
• European Community (EC) Number: 249-617-9
• DSSTox Substance ID: DTXSID00183640
• Nikkaji Number: J250.837K
• Wikidata: Q72489990
• Mol file: 29421-73-6.mol

Synonyms:3,5-Dibromo-2-methylthiophene;29421-73-6;2-Methyl-3,5-dibromo-thiophene;THIOPHENE, 3,5-DIBROMO-2-METHYL-;EINECS 249-617-9;2-methyl-3,5-dibromothiophene;Dibromo-2-methylthiophene;2-methyl3,5-dibromothiophene;SCHEMBL566671;2,4-dibromo-5-methylthiophene;DTXSID00183640;AMY10881;BCP32742;MFCD07781197;AKOS015835489;MB04800;PS-3683;CS-0109443;D3999;FT-0655166;A819909;3,5-dibromo-2-methyl-thiophene;2-METHYL-3,5-DIBROMO-THIOPHENE

Chemical Property of 3,5-Dibromo-2-methylthiophene

Chemical Property:

• Vapor Pressure: 0.0928mmHg at 25°C
• Melting Point: -15°C(lit.)
• Refractive Index: 1.62
• Boiling Point: 231.8 °C at 760 mmHg
• Flash Point: 94 °C
• PSA: 28.24000
• Density: 2.006 g/cm³
• LogP: 3.58150
• Storage Temp.: 0-10°C
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 255.83800
• Heavy Atom Count: 8
• Complexity: 86.5

Purity/Quality:

98%,99%, ^*data from raw suppliers

3,5-Dibromo-2-methylthiophene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C=C(S1)Br)Br
• Uses: 3,5-Dibromo-2-methylthiophene is a useful reagent for the preparation of arylthiophene-substituted norbornadienes.

Technology Process of 3,5-Dibromo-2-methylthiophene

There total 7 articles about 3,5-Dibromo-2-methylthiophene 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: 99.7%

2-Methylthiophene (554-14-3) → 3,5-dibromo-2-methylthiophene (29421-73-6)

Guidance literature:

With bromine; acetic acid; at 20 ℃;

DOI:10.1002/anie.201304301

Reference yield: 83.0%

2,5-dibromothiophen (3141-27-3) + methyl iodide (74-88-4) → 3,5-dibromo-2-methylthiophene (29421-73-6)

Guidance literature:

2,5-dibromothiophen; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃;

methyl iodide; In tetrahydrofuran; at -78 ℃;

DOI:10.1002/ejoc.201402774

Reference yield:

2-Methylthiophene (554-14-3) → 2-bromo-5-methyl thiophene (765-58-2) + 3,5-dibromo-2-methylthiophene (29421-73-6)

Guidance literature:

With [bis(acetoxy)iodo]benzene; lithium bromide; In tetrahydrofuran; at 20 ℃; for 0.5h; Title compound not separated from byproducts;

DOI:10.1055/s-2004-815410

upstream raw materials:

2-Methylthiophene

carbon disulfide

2,3-dibromothiophen

methyl iodide

Downstream raw materials:

3-bromo-2-methylthiophene-5-boronic acid

C₁₆H₂₁BrSSi

C₃₇H₄₂F₆S₂Si₂

C₃₁H₂₄F₆I₂S₂

Refernces

• 1、 Zuckerman, Nathaniel B.,Kang, Xiongwu,Chen, Shaowei,Konopelski, Joseph P.. "Synthesis of a ferrocene-functionalized unsymmetrical benzo[b]thienyl- thienylethene photoswitch with a cyclopentene core". . p. 1482 - 1485. Retrieved 2013.
• 2、 Abboud, Mohamed. "Synthesis and characterization of 5,5′-bis-silylated dithienylethene as a new building block of novel photochromic periodic mesoporous organosilicas". . p. 2195 - 2204. Retrieved 2020.
• 3、 Wu, Huang,Chen, Yong,Dai, Xianyin,Li, Peiyu,Stoddart, J. Fraser,Liu, Yu. "In Situ Photoconversion of Multicolor Luminescence and Pure White Light Emission Based on Carbon Dot-Supported Supramolecular Assembly". . p. 6583 - 6591. Retrieved 2019.
• 4、 Wei, Shi-Chao,Pan, Mei,Fan, Yuan-Zhong,Liu, Haoliang,Zhang, Jianyong,Su, Cheng-Yong. "Creating coordination-based cavities in a multiresponsive supramolecular gel". . p. 7418 - 7427. Retrieved 2015.
• 5、 Gu, Luyan,Zhang, Lujia,Luo, Xiao,Zheng, Ying,Ye, Zhiwei,Lv, Meng,Chen, Jinquan,Chen, Chunlai,Xiao, Yi,Zhu, Weihong,Qian, Xuhong,Yang, Youjun. "The mechanodonor-acceptor coupling (MDAC) approach for unidirectional multi-state fluorochromism". . p. 253 - 262. Retrieved 2021/01/06.