2-Bromo-5-hydroxy-4-methoxybenzaldehyde

Name: 2-Bromo-5-hydroxy-4-methoxybenzaldehyde
Brand: ChemScene
Availability: InStock
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CAS No. 2973-59-3
Cat. No. CS-W002508
Purity≥98%
MDL No.MFCD00195552

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
Accessible (Haz class 3, 4, 5 or 8), International	$238.00+

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2-Bromo-5-hydroxy-4-methoxybenzaldehyde|CS-W002508

Structure of 2973-59-3

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General Information

CAS No. 2973-59-3
Cat. No. CS-W002508
Purity ≥98%
MDL No. MFCD00195552
Storage 4°C, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₈H₇BrO₃
Molecular Weight 231.04
Synonym(s) 6-Bromoisovanillin; 2-Bromo-5-hydroxy-4-methoxybenzaldehyde
SMILES O=CC1=CC(O)=C(OC)C=C1Br

Description

2-Bromo-5-hydroxy-4-methoxybenzaldehyde features a brominated aromatic core with complementary hydroxyl and methoxy substituents, enabling selective coupling in cross-coupling reactions. The aldehyde group provides a reactive handle for conjugation, while the electron-donating methoxy and hydroxyl groups enhance regioselectivity. This compound offers improved stability and solubility under standard bench conditions, facilitating efficient synthesis in medicinal chemistry workflows.

Application

2-Bromo-5-hydroxy-4-methoxybenzaldehyde serves as a versatile building block in the synthesis of bioactive heterocycles and functionalized aromatic scaffolds. Its orthogonal functionality—bromine for cross-coupling, hydroxyl for derivatization, methoxy for electronic modulation, and aldehyde for condensation reactions—enables efficient access to complex molecular architectures. Bench-stable and compatible with standard reaction protocols, it facilitates rapid diversification in medicinal chemistry and materials science applications.

Synthesis

Route1
- In-stock
  
  621-59-0
- ~%
- In-stock
  
  2973-59-3
References
- Journal of the Chemical Society, , p. 6914 - 6922
Route2
- In-stock
  
  5392-10-9
- ~88%
- In-stock
  
  2973-59-3
References
- Kueenburg, Bernhard; Czollner, Laszlo; Frohlich, Johannes; Jordis, Ulrich Organic Process Research and Development, 1999 , vol. 3, # 6 p. 425 - 431
Route3
- In-stock
  
  15930-53-7
- ~83%
- In-stock
  
  2973-59-3
References
- Imakura; Okimoto; Konishi; Hisazumi; Yamazaki; Kobayashi; Yamashita Chemical and Pharmaceutical Bulletin, 1992 , vol. 40, # 7 p. 1691 - 1696

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 1.9758
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Aldehyde

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Chemical Biology Pharmaceutical Development and Drug Discovery Research Reagents Building Blocks for Pharmaceutical Ingredients

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2-Bromo-5-hydroxy-4-methoxybenzaldehyde

CAS No. 2973-59-3

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