Ethyl 3-bromo-4-hydroxybenzoate

Name: Ethyl 3-bromo-4-hydroxybenzoate
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CAS No. 37470-58-9
Cat. No. CS-0037718
Purity≥97%
MDL No.None

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Ethyl 3-bromo-4-hydroxybenzoate|CS-0037718

Structure of 37470-58-9

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General Information

CAS No. 37470-58-9
Cat. No. CS-0037718
Purity ≥97%
MDL No. None
Storage 4°C, protect from light, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₉H₉BrO₃
Molecular Weight 245.07
Synonym(s) Benzoic acid, 3-bromo-4-hydroxy-, ethyl ester
SMILES CCOC(=O)C1=CC(=C(C=C1)O)Br

Description

Ethyl 3-bromo-4-hydroxybenzoate features a bromine substituent at the meta position relative to a hydroxyl group on a benzoate scaffold, enabling selective functionalization in synthetic sequences. The ethyl ester moiety enhances solubility and reactivity in cross-coupling reactions, while the phenolic hydroxyl supports hydrogen bonding and further derivatization. This compound serves as a key intermediate in pharmaceutical and agrochemical synthesis.

Application

Ethyl 3-bromo-4-hydroxybenzoate serves as a versatile building block for the synthesis of substituted aromatic systems, enabling direct functionalization at the bromo and hydroxyl positions. Its stability under standard reaction conditions facilitates coupling reactions, including Suzuki and Stille couplings, while the phenolic hydroxyl group permits selective derivatization or protection. The molecule functions effectively in the construction of bioactive heterocycles and pharmaceutical intermediates, offering predictable reactivity and straightforward purification.

Synthesis

Route1
- 888731-49-5
- 64-17-5
- ~97%
- In-stock
  
  37470-58-9
References
- KEMIA, INC. Patent: WO2007/75896 A2, 2007 ; Location in patent: Page/Page column 124 ;
Route2
- 120-47-8
- ~87%
- In-stock
  
  37470-58-9
References
- Greenfield; Butera; Caufield Tetrahedron Letters, 2003 , vol. 44, # 13 p. 2729 - 2732
Route3
- In-stock
  
  14348-41-5
- ~%
- In-stock
  
  37470-58-9
References
- Meyer,H. Monatshefte fuer Chemie, 1901 , vol. 22, p. 437

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 46.53
LogP 2.3314
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Functional Group Ester

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

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Ethyl 3-bromo-4-hydroxybenzoate

CAS No. 37470-58-9

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