Ethyl 5-bromo-2-hydroxybenzoate

Base Information

• Chemical Name: Ethyl 5-bromo-2-hydroxybenzoate
• CAS No.: 37540-59-3
• Molecular Formula: C9H9BrO3
• Molecular Weight: 245.073
• Hs Code.: 2918290000
• European Community (EC) Number: 696-580-3
• DSSTox Substance ID: DTXSID00403037
• Wikidata: Q82206576
• Mol file: 37540-59-3.mol

Synonyms:ETHYL 5-BROMO-2-HYDROXYBENZOATE;37540-59-3;ethyl 5-bromosalicylate;5-bromo-2-hydroxybenzoic acid ethyl ester;Benzoic acid, 5-bromo-2-hydroxy-, ethyl ester;Ethyl 5-bromo-2-hydroxy-benzoate;Ethyl-5-bromosalicylate;5-Bromo-2-hydroxy-benzoic acid ethyl ester;SCHEMBL2313707;DTXSID00403037;OGILVZCKMMXBJI-UHFFFAOYSA-N;BBL023338;MFCD01365749;STL033033;AKOS000319643;ETHYL5-BROMO-2-HYDROXYBENZOATE;LG-0705;BB 0257845;CS-0312692;EU-0099866;FT-0653269;A823747;SR-01000596925;SR-01000596925-1

Chemical Property of Ethyl 5-bromo-2-hydroxybenzoate

Chemical Property:

• PSA: 46.53000
• LogP: 2.33140
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 243.97351
• Heavy Atom Count: 13
• Complexity: 184

Purity/Quality:

98%min ^*data from raw suppliers

Ethyl5-bromo-2-hydroxybenzoate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCOC(=O)C1=C(C=CC(=C1)Br)O
• Uses: Ethyl 5-Bromo-2-hydroxybenzoate is used in preparation of chrysin-substituted salicylate ether compounds as nonsteroidal antiinflammatory agents and anticancer agents.

Technology Process of Ethyl 5-bromo-2-hydroxybenzoate

There total 7 articles about Ethyl 5-bromo-2-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: 90.0%

(benzotriazol-1-yl)(5-bromo-2-hydroxyphenyl)methanone (333747-08-3) + ethanol (64-17-5) → 2-hydroxy-5-bromobenzoic acid ethyl ester (37540-59-3)

Guidance literature:

In tetrahydrofuran; at 120 ℃; for 0.166667h; microwave irradiation;

DOI:10.1021/jo052293q

Reference yield: 89.0%

2-hydroxy-benzoic acid ethyl ester (118-61-6) → 2-hydroxy-5-bromobenzoic acid ethyl ester (37540-59-3)

Guidance literature:

With perchloric acid; dihydrogen peroxide; C₁₆H₁₀N₄O₄^(4-)*C₃H₇NO*6Na⁽¹⁺⁾*2OV⁽³⁺⁾*2O^(2-)*4HO^(1-); potassium bromide; In water; at 20 ℃; for 0.5h; Reagent/catalyst;

DOI:10.1016/j.ica.2020.120068

Reference yield: 84.0%

ethyl 3-bromobenzoate (24398-88-7) → 2-hydroxy-5-bromobenzoic acid ethyl ester (37540-59-3)

Guidance literature:

With [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; Selectfluor; trifluoroacetic acid; trifluoroacetic anhydride; at 105 ℃; for 10h;

DOI:10.1021/ol301104n

upstream raw materials:

2-hydroxy-benzoic acid ethyl ester

chloroform

bromine

(benzotriazol-1-yl)(5-bromo-2-hydroxyphenyl)methanone

Downstream raw materials:

C₁₃H₁₅BrO₅

ethyl 5-bromo-2-ethoxybenzoate

ethyl 5-bromo-2-methoxybenzoate

ethyl 2-acetoxy-5-bromobenzoate

Refernces

• 1、 Kurbah, Sunshine Dominic,Lal, Ram A.. "Bioinspired catalysis and bromoperoxidase like activity of a multistimuli-responsive supramolecular metallogel: Supramolecular assembly triggered by pi-pi stacking and hydrogen bonding interactions". . p. 5410 - 5418. Retrieved 2020/04/17.
• 2、 Syiemlieh, Ibanphylla,Asthana, Mrityunjaya,Lal, Ram A.. "Reactivity and Catalytic Activity of Homobimetallic Vanadium(V) Complex Derived from Bis(5-chlorosalicylaldehyde)oxaloyldihydrazone Ligand". . . Retrieved 2019/05/28.