3-Bromo-2-methylbenzoyl chloride

Base Information

• Chemical Name: 3-Bromo-2-methylbenzoyl chloride
• CAS No.: 21900-48-1
• Molecular Formula: C8H6 Br Cl O
• Molecular Weight: 233.492
• Hs Code.: 2916399090
• DSSTox Substance ID: DTXSID90598426
• Wikidata: Q82494183
• Mol file: 21900-48-1.mol

Synonyms:3-Bromo-2-methylbenzoyl chloride;21900-48-1;3-BROMO-2-METHYLBENZOYLCHLORIDE;3-BROMO-2-METHYL BENZOYL CHLORIDE;Benzoyl chloride,3-bromo-2-methyl-;SCHEMBL3710686;DTXSID90598426;JUNGKBUTMUFRGV-UHFFFAOYSA-N;3-bromo-2-methyl-benzoyl chloride;WAA90048;MFCD08543466;3-bromo-2-methylbenzoic acid chloride;AKOS013152077;PS-10787

Chemical Property of 3-Bromo-2-methylbenzoyl chloride

Chemical Property:

• PSA: 17.07000
• LogP: 3.13650
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 231.92906
• Heavy Atom Count: 11
• Complexity: 160

Purity/Quality:

98%Min ^*data from raw suppliers

3-Bromo-2-methylbenzoylChloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C=CC=C1Br)C(=O)Cl

Technology Process of 3-Bromo-2-methylbenzoyl chloride

There total 5 articles about 3-Bromo-2-methylbenzoyl chloride 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:

3-bromo-2-methylbenzoic acid (76006-33-2) → 3-bromo-2-methylbenzoic acid chloride (21900-48-1)

Guidance literature:

With thionyl chloride;

DOI:10.1016/j.bmcl.2004.06.041

Reference yield:

1-methyl-4-nitrobenzene (99-99-0) → 3-bromo-2-methylbenzoic acid chloride (21900-48-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: bromine; iron / chloroform / 48 h / 40 °C / Reflux

2.1: tin(II) chloride dihdyrate / tetrahydrofuran; ethanol / 3 h / 20 °C

2.2: 1.5 h

3.1: hydrogenchloride / water / 0.33 h

3.2: 2 h / 0 - 5 °C

3.3: 0 - 20 °C

4.1: tert.-butyl lithium / tetrahydrofuran; pentane / 2 h / -80 - -76 °C

4.2: -80 °C

4.3: pH 1

5.1: thionyl chloride / toluene / 2 h / Reflux

With hydrogenchloride; thionyl chloride; tin(II) chloride dihdyrate; bromine; tert.-butyl lithium; iron; In tetrahydrofuran; ethanol; chloroform; water; toluene; pentane;

Reference yield:

2,6-dibromotoluene (69321-60-4) → 3-bromo-2-methylbenzoic acid chloride (21900-48-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: tert.-butyl lithium / tetrahydrofuran; pentane / 2 h / -80 - -76 °C

1.2: -80 °C

1.3: pH 1

2.1: thionyl chloride / toluene / 2 h / Reflux

With thionyl chloride; tert.-butyl lithium; In tetrahydrofuran; toluene; pentane;

upstream raw materials:

3-bromo-2-methylbenzoic acid

1-methyl-4-nitrobenzene

2,6-dibromotoluene

1,3-dibromo-2-methyl-5-nitrobenzene

Downstream raw materials:

[(3-bromo-2-methylphenyl)methyl]amine hydrochloride

Refernces

• 1、 Liu, Sien,He, Bangyue,Li, Hongyi,Zhang, Xiaofeng,Shang, Yaping,Su, Weiping. "Facile Synthesis of Alkylidene Phthalides by Rhodium-Catalyzed Domino C?H Acylation/Annulation of Benzamides with Aliphatic Carboxylic Acids". supporting information. p. 15628 - 15633. Retrieved 2021/10/05.
• 2、 Carter, David S.,Jacobs, Robert T.,Freund, Yvonne R.,Berry, Pamela W.,Akama, Tsutomu,Easom, Eric E.,Lunde, Christopher S.,Rock, Fernando,Stefanakis, Rianna,Mckerrow, James,Fischer, Chelsea,Bulman, Christina A.,Lim, Kee Chong,Suzuki, Brian M.,Tricoche, Nancy,Sakanari, Judy A.,Lustigman, Sara,Plattner, Jacob J.. "Macrofilaricidal Benzimidazole-Benzoxaborole Hybrids as an Approach to the Treatment of River Blindness: Part 2. Ketone Linked Analogs". . p. 180 - 185. Retrieved 2020/02/13.