Methyl 2-bromo-5-hydroxybenzoate

Base Information

• Chemical Name: Methyl 2-bromo-5-hydroxybenzoate
• CAS No.: 154607-00-8
• Molecular Formula: C8H7BrO3
• Molecular Weight: 231.046
• Hs Code.: 2918290000
• European Community (EC) Number: 894-624-8
• Mol file: 154607-00-8.mol

Synonyms:methyl 2-bromo-5-hydroxybenzoate;154607-00-8;2-Bromo-5-hydroxybenzoic acid methyl ester;Methyl2-bromo-5-hydroxybenzoate;MFCD10566797;Methyl 2-bromo-5-hydroxybenzenecarboxylate;SCHEMBL177377;methyl-2-bromo-5-hydroxybenzoate;AIWIFVOBRBJANE-UHFFFAOYSA-N;CS-B1202;AKOS022170646;MS-9828;DA-09885;SY243192;Methyl-2-bromo-5-hydroxybenzene carboxylate;2-Bromo-5-hydroxy-benzoic acid methyl ester;EN300-3195978;A929408;Z1269174265

Chemical Property of Methyl 2-bromo-5-hydroxybenzoate

Chemical Property:

• Boiling Point: 326.9±22.0 °C(Predicted)
• PKA: 8.58±0.18(Predicted)
• PSA: 46.53000
• Density: 1.627±0.06 g/cm3(Predicted)
• LogP: 1.94130
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 229.95786
• Heavy Atom Count: 12
• Complexity: 172

Purity/Quality:

98%Min ^*data from raw suppliers

Methyl2-Bromo-5-hydroxybenzoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=C(C=CC(=C1)O)Br
• Uses: Methyl 2-Bromo-5-hydroxybenzoate is used in preparation of macrocyclic Mcl-1 inhibitors for the treatment of multiple myeloma.

Technology Process of Methyl 2-bromo-5-hydroxybenzoate

There total 6 articles about Methyl 2-bromo-5-hydroxybenzoate 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: 93.0%

methyl 3-hydroxybenzoate (19438-10-9) → methyl 3-hydroxy-6-bromobenzoate (154607-00-8)

Guidance literature:

With bromine; In dichloromethane; at 20 ℃; for 4h;

Reference yield: 83.0%

methyl 2-bromo-5-methoxybenzoate (35450-36-3) → methyl 3-hydroxy-6-bromobenzoate (154607-00-8)

Guidance literature:

With boron trichloride; In 1,2-dichloro-ethane; at -78 - 20 ℃;

DOI:10.1021/acs.oprd.9b00199

Reference yield: 36.2%

methyl 3-hydroxybenzoate (19438-10-9) → methyl 4-bromo-3-hydroxybenzoate (106291-80-9) + methyl 3-hydroxy-6-bromobenzoate (154607-00-8)

Guidance literature:

With bromine; In acetic acid; at 0 - 25 ℃; for 5h; Inert atmosphere;

DOI:10.1021/acs.jmedchem.7b00373

upstream raw materials:

methyl 2-bromo-5-methoxybenzoate

methyl 3-hydroxybenzoate

methanol

2-bromo-5-methoxy-benzoic acid

Downstream raw materials:

methyl 2-bromo-5-(4-fluorobenzyloxy)benzoate

5-benzyloxy-2-(3-hydroxyprop-1-ynyl)benzoic acid methyl ester

5-benzyloxy-2-[3-(tert-butyldimethylsilanyloxy)prop-1-ynyl]benzoic acid methyl ester

7-benzyloxy-4-bromo-3-(tert-butyldimethylsilanyloxymethyl)isochromen-1-one

Refernces

• 1、 Dressler, Justin J.,Charlesworth-Seiler, Eva M.,Dahl, Bart J.. "Synthesis of a triethylene glycol-capped benzo[1,2-c:4,5-c']bis[2]benzopyran-5,12-dione: A highly soluble dilactone-bridged p-terphenyl with a crankshaft architecture". supporting information. . Retrieved 2020/10/02.
• 2、 -. "Near infrared fluorescent probe capable of being used for responding to pH change in living cells in chronic wound development process and preparation method of probe". Paragraph 0039; 0041; 0043-0045. . Retrieved 2019/06/07.