Methyl 2-bromo-4-hydroxybenzoate

Name: Methyl 2-bromo-4-hydroxybenzoate
Brand: ChemScene
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CAS No. 101085-03-4
Cat. No. CS-0133272
Purity≥98%
MDL No.None

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Methyl 2-bromo-4-hydroxybenzoate|CS-0133272

Structure of 101085-03-4

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General Information

CAS No. 101085-03-4
Cat. No. CS-0133272
Purity ≥98%
MDL No. None
Storage RT, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₈H₇BrO₃
Molecular Weight 231.04
Synonym(s) Methyl2-bromo-4-hydroxybenzoate
SMILES O=C(OC)C1=CC=C(O)C=C1Br

Description

Methyl 2-bromo-4-hydroxybenzoate features a bromine atom at the ortho position relative to the ester group and a hydroxyl moiety at the para position, creating a uniquely reactive scaffold. This electronic asymmetry enables selective functionalization in cross-coupling and derivatization workflows. The molecule exhibits good stability under standard conditions and integrates readily into synthetic sequences requiring halogen-directed transformations.

Application

Methyl 2-bromo-4-hydroxybenzoate serves as a versatile building block in synthetic organic chemistry, enabling regioselective functionalization at the aromatic ring. The bromo group facilitates Suzuki, Stille, and Negishi couplings, while the hydroxyl and ester functionalities offer orthogonal handles for further derivatization. Bench-stable and readily purified by recrystallization, it functions effectively in standard cross-coupling and heterocycle construction workflows.

Synthesis

Route1
- In-stock
  
  98545-64-3
- ~40%
- In-stock
  
  101085-03-4
References
- Jung, Kwan-Young; Vanommeslaeghe, Kenno; Lanning, Maryanna E.; Yap, Jeremy L.; Gordon, Caryn; Wilder, Paul T.; Mackerell, Alexander D.; Fletcher, Steven Organic Letters, 2013 , vol. 15, # 13 p. 3234 - 3237
Route2
- 67-56-1
- In-stock
  
  28547-28-6
- ~96%
- In-stock
  
  101085-03-4
References
- Masiero, Stefano; Lena, Stefano; Pieraccini, Silvia; Spada, Gian Piero Angewandte Chemie - International Edition, 2008 , vol. 47, # 17 p. 3184 - 3187
Route3
- In-stock
  
  100959-22-6
- ~%
- In-stock
  
  101085-03-4
References
- Jung, Kwan-Young; Vanommeslaeghe, Kenno; Lanning, Maryanna E.; Yap, Jeremy L.; Gordon, Caryn; Wilder, Paul T.; Mackerell, Alexander D.; Fletcher, Steven Organic Letters, 2013 , vol. 15, # 13 p. 3234 - 3237

Safety Information

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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 1.9413
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Ester

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

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Methyl 2-bromo-4-hydroxybenzoate

CAS No. 101085-03-4

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