2-Bromo-3-methylphenol

Base Information

• Chemical Name: 2-Bromo-3-methylphenol
• CAS No.: 22061-78-5
• Molecular Formula: C7H7BrO
• Molecular Weight: 187.036
• Hs Code.: 2908199090
• European Community (EC) Number: 824-462-5
• NSC Number: 100895
• DSSTox Substance ID: DTXSID10295268
• Nikkaji Number: J801.790E
• Wikidata: Q82035098
• Mol file: 22061-78-5.mol

Synonyms:2-bromo-3-methylphenol;22061-78-5;2-bromo-3-methyl-Phenol;Phenol, 2-bromo-3-methyl-;MFCD09991797;2-Bromo-3-hydroxytoluene;Brom-m-kresol;NSC100895;NCIOpen2_001879;SCHEMBL2046791;DTXSID10295268;HUGNLEZLTOVJLD-UHFFFAOYSA-N;BCP31084;CL8460;AKOS006310392;AM82854;CS-W004719;GS-3791;MB08359;NSC-100895;AC-22656;SY067392;FT-0708281;EN300-105060;J-014456;J-523926;Z1198267200;2-bromo-3-methyl-phenol

Chemical Property of 2-Bromo-3-methylphenol

Chemical Property:

• Vapor Pressure: 0.102mmHg at 25°C
• Melting Point: 58.5-59 °C
• Refractive Index: 1.59
• Boiling Point: 215.2 °C at 760 mmHg
• PKA: 8.54±0.10(Predicted)
• Flash Point: 83.9 °C
• PSA: 20.23000
• Density: 1.554 g/cm³
• LogP: 2.46310
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 185.96803
• Heavy Atom Count: 9
• Complexity: 94.9

Purity/Quality:

99% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(=CC=C1)O)Br
• Uses: 2-Bromo-3-methylphenol is a reagent used in chemoselective and regioselective oxybromination of phenols with dioxygen

Technology Process of 2-Bromo-3-methylphenol

There total 14 articles about 2-Bromo-3-methylphenol 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: 88.0%

3-methyl-phenol (108-39-4) → 2-bromo-3-methylphenol (22061-78-5)

Guidance literature:

With 1-butyl-3-methylpyridinium tribromide; at 20 ℃; for 0.5h;

DOI:10.1016/j.tetlet.2008.12.053

Reference yield: 88.0%

2-bromo-3-methylaniline (54879-20-8) → 2-bromo-3-methylphenol (22061-78-5)

Guidance literature:

2-bromo-3-methylaniline; With sulfuric acid; In water; at 0 ℃; Inert atmosphere;

With sodium nitrite; In water; at 0 - 5 ℃; Inert atmosphere;

With sodium hydrogen sulfate; sulfuric acid; urea; In water; at 0 - 140 ℃; Inert atmosphere;

DOI:10.1002/anie.201003549

Reference yield: 85.0%

3-methyl-phenol (108-39-4) → 4-bromo-3-methylphenol (14472-14-1) + 2-bromo-3-methylphenol (22061-78-5)

Guidance literature:

With N-Bromosuccinimide; at 0 ℃; for 2h; regioselective reaction;

DOI:10.1021/acs.joc.7b02920

upstream raw materials:

2-amino-3-methylphenol

3-methyl-phenol

2-bromo-3-methylaniline

sulfuric acid

Downstream raw materials:

2-formyl-6-hydroxy-benzoic acid

methyl 6-methylsalicylate

2-acetoxy-6-methylbenzoic acid

methyl 2-acetoxy-6-methylbenzoate

Refernces

• 1、 Munday, Samuel D.,Dezvarei, Shaghayegh,Lau, Ian C.-K.,Bell, Stephen G.. "Examination of Selectivity in the Oxidation of ortho- and meta-Disubstituted Benzenes by CYP102A1 (P450 Bm3) Variants". . p. 2512 - 2522. Retrieved 2017/07/12.
• 2、 Kitching, Matthew O.,Hurst, Timothy E.,Snieckus, Victor. "Copper-catalyzed cross-coupling interrupted by an opportunistic smiles rearrangement: An efficient domino approach to dibenzoxazepinones". supporting information; experimental part. p. 2925 - 2929. Retrieved 2012/05/04.