2-Bromo-4,6-dimethoxybenzaldehyde

Name: 2-Bromo-4,6-dimethoxybenzaldehyde
Brand: ChemScene
Availability: InStock
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CAS No. 81574-69-8
Cat. No. CS-0038407
Purity≥97%
MDL No.MFCD11110636

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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-4,6-dimethoxybenzaldehyde|CS-0038407

Structure of 81574-69-8

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General Information

CAS No. 81574-69-8
Cat. No. CS-0038407
Purity ≥97%
MDL No. MFCD11110636
Storage 4°C, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₉H₉BrO₃
Molecular Weight 245.07
Synonym(s) None
SMILES COC1=CC(=C(C=O)C(=C1)Br)OC

Description

2-Bromo-4,6-dimethoxybenzaldehyde features a brominated aromatic core with two methoxy groups positioned ortho to the aldehyde, delivering enhanced electron density and stability. This configuration supports efficient coupling in cross-coupling reactions and facilitates downstream functionalization in medicinal chemistry and materials synthesis.

Application

2-Bromo-4,6-dimethoxybenzaldehyde serves as a versatile building block in medicinal chemistry and agrochemical synthesis, enabling efficient Suzuki-Miyaura and Stille couplings due to its well-defined electronic profile and ortho-bromine reactivity. The dimethoxy substitution pattern enhances solubility and stability, while the aldehyde group facilitates downstream transformations such as reductive amination or condensation reactions. Its bench-stable nature and predictable regioselectivity make it ideal for multi-step syntheses requiring functional group compatibility.

Synthesis

Route1
- In-stock
  
  20469-65-2
- ~91%
- In-stock
  
  81574-69-8
References
- Persich, Peter; Llaveria, Josep; Lhermet, Rudy; Deharo, Teresa; Stade, Robert; Kondoh, Azusa; Fuerstner, Alois Chemistry - A European Journal, 2013 , vol. 19, # 39 p. 13047 - 13058
Route2
- In-stock
  
  20469-65-2
- 68-12-2
- ~99%
- In-stock
  
  81574-69-8
References
- THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK; SNYDER, Scott Alan; SHERWOOD, Trevor C.; ROSS, Audrey G.; OH, Hyunju; GHOSH, Sankar Patent: WO2011/103442 A2, 2011 ; Location in patent: Page/Page column 7; 61-62 ;

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-H332-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501

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Computational Chemistry Data

TPSA 35.53
LogP 2.2788
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 3

Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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2-Bromo-4,6-dimethoxybenzaldehyde

CAS No. 81574-69-8

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