Ethyl 3-bromo-4-hydroxybenzoate

Base Information

• Chemical Name: Ethyl 3-bromo-4-hydroxybenzoate
• CAS No.: 37470-58-9
• Molecular Formula: C9H9BrO3
• Molecular Weight: 245.073
• Hs Code.: 2918290000
• European Community (EC) Number: 692-064-7
• DSSTox Substance ID: DTXSID80406526
• Wikidata: Q82211526
• Mol file: 37470-58-9.mol

Synonyms:ETHYL 3-BROMO-4-HYDROXYBENZOATE;37470-58-9;MFCD06204654;Benzoic acid, 3-bromo-4-hydroxy-, ethyl ester;3-bromo-4-hydroxybenzoic acid ethyl ester;SCHEMBL2543424;DTXSID80406526;CMXRBHNFKLKRFS-UHFFFAOYSA-N;AKOS000319635;ETHYL3-BROMO-4-HYDROXYBENZOATE;AS-60508;SY060932;CS-0037718;FT-0655265;A823682

Chemical Property of Ethyl 3-bromo-4-hydroxybenzoate

Chemical Property:

• Melting Point: 102.2-103.1 °C(Solv: hexane (110-54-3))
• Boiling Point: 297.9±20.0 °C(Predicted)
• PKA: 6.82±0.18(Predicted)
• PSA: 46.53000
• Density: 1.546±0.06 g/cm3(Predicted)
• LogP: 2.33140
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 2.7
• 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

Ethyl 3-bromo-4-hydroxybenzoate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCOC(=O)C1=CC(=C(C=C1)O)Br

Technology Process of Ethyl 3-bromo-4-hydroxybenzoate

There total 3 articles about Ethyl 3-bromo-4-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%

Ethyl 4-hydroxybenzoate (120-47-8) → ethyl 2-bromo-4-hydroxybenzoate (37470-58-9)

Guidance literature:

With N-Bromosuccinimide; tetrafluoroboric acid;

DOI:10.1016/S0040-4039(03)00333-2

Reference yield: 89.0%

di(methyl)tert-butyl(ethoxy)silane (17348-65-1) + 4-hydroxy-benzaldehyde (123-08-0,65581-83-1) → ethyl 2-bromo-4-hydroxybenzoate (37470-58-9)

Guidance literature:

With Bromotrichloromethane; [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; In acetonitrile; at 20 ℃; for 6h; Irradiation;

DOI:10.1055/s-0037-1610717

Reference yield: 86.0%

ethanol (64-17-5) + 3-bromo-4-hydroxy-benzoic acid (14348-41-5) → ethyl 2-bromo-4-hydroxybenzoate (37470-58-9)

Guidance literature:

With sulfuric acid; for 3h; Reflux; Inert atmosphere;

DOI:10.1080/00304948.2020.1834819

upstream raw materials:

Ethyl 4-hydroxybenzoate

ethanol

3-bromo-4-hydroxy-benzoic acid

di(methyl)tert-butyl(ethoxy)silane

Downstream raw materials:

3-bromo-4-butoxy-benzoic acid ethyl ester

ethyl 3-bromo-4-(2-methylallyloxy)benzoate

C₁₄H₁₂BrNO₃

C₁₆H₁₅BrN₂O₄

Refernces

• 1、 Berlin, K. Darrell,Bryant, Daniel J.,Bunce, Richard A.. "1,3,3-Trimethylindolin-5-amine and 4-Formylphenyl 4,4-Dimethylchroman-6-carboxylate Thiosemicarbazone (OHet72)". . p. 68 - 77. Retrieved 2021/01/05.
• 2、 Talukdar, Ranadeep. "Single-Step Dual Functionalization: One-Pot Bromination-Cross-Dehydrogenative Esterification of Hydroxy Benzaldehydes with CCl 3 Br - A Comparison with Selectfluor". supporting information. p. 1713 - 1718. Retrieved 2019/08/28.