Methyl 5-bromo-2,3-dihydroxybenzoate

Base Information

• Chemical Name: Methyl 5-bromo-2,3-dihydroxybenzoate
• CAS No.: 105603-49-4
• Molecular Formula: C8H7BrO4
• Molecular Weight: 247.045
• Hs Code.: 2918290000
• DSSTox Substance ID: DTXSID70700141
• Wikidata: Q82631337
• Mol file: 105603-49-4.mol

Synonyms:METHYL 5-BROMO-2,3-DIHYDROXYBENZOATE;105603-49-4;5-Bromo-2,3-dihydroxybenzoic acid methyl ester;SCHEMBL856043;DTXSID70700141;MFCD01412199;AKOS022173708;DS-5942;METHYL5-BROMO-2,3-DIHYDROXYBENZOATE;CS-0150899;C71222;A895984;A1-01324

Chemical Property of Methyl 5-bromo-2,3-dihydroxybenzoate

Chemical Property:

• Melting Point: 119-123oC
• Boiling Point: 334.8±37.0 °C(Predicted)
• PKA: 8.02±0.15(Predicted)
• PSA: 66.76000
• Density: 1.759±0.06 g/cm3(Predicted)
• LogP: 1.64690
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: DMSO (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 245.95277
• Heavy Atom Count: 13
• Complexity: 197

Purity/Quality:

97% ^*data from raw suppliers

5-Bromo-2,3-dihydroxybenzoicAcidMethylEster ^*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)Br)O)O
• Uses: methyl 5-bromo-2,3-dihydroxybenzoate is used in the preparation of hydroxyalbuterol and bisubstrate inhibitors. Displays low inhibitory activity towards sn-glycerol-3-phosphate oxidase of Trypanosoma brucei brucei.

Technology Process of Methyl 5-bromo-2,3-dihydroxybenzoate

There total 2 articles about Methyl 5-bromo-2,3-dihydroxybenzoate 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: 84.0%

methanol (67-56-1) + 2,3-dihydroxy-5-bromobenzoic acid (72517-15-8) → methyl 5-bromo-2,3-dihydroxybenzoate (105603-49-4)

Guidance literature:

With sulfuric acid; for 16h; Heating;

DOI:10.1016/0960-894X(96)00413-1

Reference yield:

2,3-Dihydroxybenzoic acid (303-38-8) → methyl 5-bromo-2,3-dihydroxybenzoate (105603-49-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 71 percent / Br₂, HOAc / 20 h / Ambient temperature

2: 84 percent / H₂SO₄ / 16 h / Heating

With sulfuric acid; bromine; acetic acid;

DOI:10.1016/0960-894X(96)00413-1

Reference yield: 95.0%

1-chloro-2-(chloromethyl)benzene (611-19-8) + methyl 5-bromo-2,3-dihydroxybenzoate (105603-49-4) → C22H17BrCl2O4 (533897-62-0)

Guidance literature:

With potassium carbonate; tetra-(n-butyl)ammonium iodide; In DMF (N,N-dimethyl-formamide); at 60 ℃; for 4h;

upstream raw materials:

methanol

2,3-dihydroxy-5-bromobenzoic acid

2,3-Dihydroxybenzoic acid

Downstream raw materials:

methyl 2,3-bis(benzyloxy)-5-bromobenzoate

methyl 6-bromo-2,2-diphenyl-1,3-benzodioxole-4-carboxylate

6-bromo-2,2-diphenyl-1,3-benzodioxole-4-carboxylic acid

6-cyano-2,2-diphenyl-1,3-benzodioxole-4-carboxylic acid