(4-Bromo-5-methylthiophen-2-yl)boronic acid

Base Information

• Chemical Name: (4-Bromo-5-methylthiophen-2-yl)boronic acid
• CAS No.: 154566-69-5
• Molecular Formula: C5H6BBrO2S
• Molecular Weight: 220.882
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID10479526
• Nikkaji Number: J1.346.810I
• Wikidata: Q72448158
• Mol file: 154566-69-5.mol

Synonyms:154566-69-5;4-Bromo-5-methylthiophene-2-boronic acid;(4-Bromo-5-methylthiophen-2-yl)boronic acid;5-Methyl-4-bromothiophen-2-ylboronic acid;3-Bromo-2-methyl-5-thienylboronic acid;MFCD09952079;C5H6BBrO2S;(4-BROMO-5-METHYL-2-THIENYL)BORONIC ACID;SCHEMBL2186108;DTXSID10479526;CVCCYVWSTHTZFM-UHFFFAOYSA-N;AKOS015834571;AB55299;DS-10776;3-Bromo-2-methylthiophen-5-ylboronic acid;CS-0108818;FT-0655948;EN300-371193;10.14272/CVCCYVWSTHTZFM-UHFFFAOYSA-N.1;A809551;doi:10.14272/CVCCYVWSTHTZFM-UHFFFAOYSA-N.1;Z1269176948;(4-bromo-5-methyl-2-thienyl)boronic acid

Chemical Property of (4-Bromo-5-methylthiophen-2-yl)boronic acid

Chemical Property:

• Appearance/Colour: off-white solid
• Refractive Index: 1.61
• Boiling Point: 357.5 °C at 760 mmHg
• Flash Point: 170 °C
• PSA: 68.70000
• Density: 1.75 g/cm³
• LogP: 0.49880
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 219.93649
• Heavy Atom Count: 10
• Complexity: 124

Purity/Quality:

98%min ^*data from raw suppliers

4-Bromo-5-methylthiophene-2-boronicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC(=C(S1)C)Br)(O)O

Technology Process of (4-Bromo-5-methylthiophen-2-yl)boronic acid

There total 6 articles about (4-Bromo-5-methylthiophen-2-yl)boronic acid 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: 96.0%

3,5-dibromo-2-methylthiophene (29421-73-6) + boric acid tributyl ester (688-74-4) + water (7732-18-5) → 3-bromo-2-methylthiophene-5-boronic acid (154566-69-5)

Guidance literature:

3,5-dibromo-2-methylthiophene; With n-butyllithium; In diethyl ether; hexane; at -78 ℃; for 0.5h; Inert atmosphere;

boric acid tributyl ester; In diethyl ether; hexane; at 20 ℃; Inert atmosphere;

water; With hydrogenchloride; In diethyl ether; hexane; Inert atmosphere;

DOI:10.1021/acs.inorgchem.8b00146

Reference yield: 93.0%

3,5-dibromo-2-methylthiophene (29421-73-6) + boric acid tributyl ester (688-74-4) → 3-bromo-2-methylthiophene-5-boronic acid (154566-69-5)

Guidance literature:

3,5-dibromo-2-methylthiophene; With n-butyllithium; In diethyl ether; hexane; at -78 ℃; for 1h; Schlenk technique; Inert atmosphere;

boric acid tributyl ester; In diethyl ether; hexane; at 20 ℃; Schlenk technique; Inert atmosphere;

DOI:10.1002/chem.202103133

Reference yield: 90.0%

3,5-dibromo-2-methylthiophene (29421-73-6) → 3-bromo-2-methylthiophene-5-boronic acid (154566-69-5)

Guidance literature:

3,5-dibromo-2-methylthiophene; With n-butyllithium; In tetrahydrofuran; at -78 ℃; Inert atmosphere;

With Triisopropyl borate; In tetrahydrofuran; at -78 - 20 ℃; for 1h; Inert atmosphere;

With water; Inert atmosphere;

DOI:10.1002/ejoc.201100166

upstream raw materials:

3,5-dibromo-2-methylthiophene

2-Methylthiophene

boric acid tributyl ester

Triisopropyl borate

Downstream raw materials:

3-Bromo-5-(O-methoxymethyl-3',5'-di-tert-butyl-4'-hydroxyphenyl)-2-methylthiophene

[4-(4-Bromo-5-methyl-thiophen-2-yl)-phenyl]-methanol

3-bromo-2-methyl-5-(p-(N,N-dimethylamino)phenyl)thiophene

3-bromo-2-methyl-5-(3-methylphenyl)thiophene

Refernces

• 1、 Nikolayenko, Varvara I.,Castell, Dominic C.,van Heerden, Dewald P.,Barbour, Leonard J.. "Guest-Induced Structural Transformations in a Porous Halogen-Bonded Framework". . p. 12086 - 12091. Retrieved 2018.
• 2、 Presa, Andreu,Vázquez, Guillem,Barrios, Leoní A.,Roubeau, Olivier,Korrodi-Gregório, Luís,Pérez-Tomás, Ricardo,Gamez, Patrick. "Photoactivation of the cytotoxic properties of platinum(II) complexes through ligand photoswitching". . p. 4009 - 4022. Retrieved 2018.
• 3、 Adams, J?rg,Dahle, Sebastian,Hübner, Eike G.,Lederle, Felix,Maus-Friedrichs, Wolfgang,Nagorny, Sven,Schmidt, Andreas,Udachin, Viktor,Weingartz, Thea. "Switchable Mesomeric Betaines Derived from Pyridinium-Phenolates and Bis(thienyl)ethane". . p. 3178 - 3189. Retrieved 2021/07/02.
• 4、 Büllmann, Simon M.,J?schke, Andres. "Norbornadiene-bridged diarylethenes and their conversion into turn-off fluorescent photoswitches". . p. 7124 - 7127. Retrieved 2020/07/14.