Ethyl 3-bromo-5-hydroxybenzoate

Base Information

• Chemical Name: Ethyl 3-bromo-5-hydroxybenzoate
• CAS No.: 870673-35-1
• Molecular Formula: C9H9BrO3
• Molecular Weight: 245.073
• DSSTox Substance ID: DTXSID00470946
• Wikidata: Q82299237
• Mol file: 870673-35-1.mol

Synonyms:ethyl 3-bromo-5-hydroxybenzoate;870673-35-1;SCHEMBL2208614;DTXSID00470946;GCHMYKMWYBHYSV-UHFFFAOYSA-N;MFCD10566802;3-Bromo-5-hydroxybenzoic acid ethyl ester;CS-0193208;FT-0734799;E88014

Chemical Property of Ethyl 3-bromo-5-hydroxybenzoate

Chemical Property:

• Melting Point: 96 °C(Solv: heptane (142-82-5))
• Boiling Point: 342.0±22.0 °C(Predicted)
• PKA: 8.23±0.10(Predicted)
• PSA: 46.53000
• Density: 1.546±0.06 g/cm3(Predicted)
• LogP: 2.33140
• 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:

95% ^*data from raw suppliers

Benzoicacid,3-bromo-5-hydroxy-,ethylester 95 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Ethyl 3-bromo-5-hydroxybenzoate

There total 5 articles about Ethyl 3-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: 99.0%

ethanol (64-17-5) + 3-bromo-5-hydroxy-benzoic acid (140472-69-1) → 3-bromo-5-hydroxybenzoic acid ethyl ester (870673-35-1)

Guidance literature:

With thionyl chloride; at 0 - 20 ℃;

Reference yield: 94.0%

→ 3-bromo-5-hydroxybenzoic acid ethyl ester (870673-35-1)

Guidance literature:

Reference yield:

3-bromo-5-nitro-benzoic acid (6307-83-1) → 3-bromo-5-hydroxybenzoic acid ethyl ester (870673-35-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: hydrogenchloride / ethanol; water / 0.08 h / 20 °C

1.2: 2 h / 50 °C

2.1: water; sulfuric acid; sodium nitrite / 1.67 h / Reflux

3.1: sulfuric acid / 5 h / 90 °C

With hydrogenchloride; sulfuric acid; water; sodium nitrite; In ethanol; water;

DOI:10.1021/acs.jmedchem.6b00829

upstream raw materials:

ethanol

3-bromo-5-hydroxy-benzoic acid

3-nitrobenzoic acid

3-bromo-5-nitro-benzoic acid

Downstream raw materials:

ethyl 3-hydroxy-5-[2-(trimethylsilyl)ethynyl]benzoate

ethyl 3-ethynyl-5-hydroxybenzoate

diethyl 5,5'-[benzene-1,4-diyl-bis(ethyne-2,1-diyl)]bis(3-hydroxybenzoate)

diethyl 5,5'-[tolan-4,4'-diyl-bis(ethyne-2,1-diyl)]bis(3-hydroxybenzoate)

Refernces

• 1、 Ciardiello, Joe J.,Galloway, Warren R.J.D.,O'Connor, Cornelius J.,Sore, Hannah F.,Stokes, Jamie E.,Wu, Yuteng,Spring, David R.. "An expedient strategy for the diversity-oriented synthesis of macrocyclic compounds with natural product-like characteristics". . p. 3567 - 3578. Retrieved 2016/07/06.
• 2、 Junker, Anna,Balasubramanian, Ramachandran,Ciancetta, Antonella,Uliassi, Elisa,Kiselev, Evgeny,Martiriggiano, Chiara,Trujillo, Kevin,Mtchedlidze, Giorgi,Birdwell, Leah,Brown, Kyle A.,Harden, T. Kendall,Jacobson, Kenneth A.. "Structure-Based Design of 3-(4-Aryl-1H-1,2,3-triazol-1-yl)-Biphenyl Derivatives as P2Y14 Receptor Antagonists". supporting information. p. 6149 - 6168. Retrieved 2016/07/26.