2-Bromo-5-methylbenzaldehyde

Name: 2-Bromo-5-methylbenzaldehyde
Brand: ChemScene
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CAS No. 90221-55-9
Cat. No. CS-W004919
Purity≥98%
MDL No.MFCD08669550

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
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Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
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Structure of 90221-55-9

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General Information

CAS No. 90221-55-9
Cat. No. CS-W004919
Purity ≥98%
MDL No. MFCD08669550
Storage 4°C, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₈H₇BrO
Molecular Weight 199.05
Synonym(s) Bromo-5-methylbenzaldehyde
SMILES O=CC1=CC(C)=CC=C1Br

Description

2-Bromo-5-methylbenzaldehyde features a bromine atom at the ortho position relative to the aldehyde group and a methyl substituent at the meta position, creating a sterically accessible, electron-deficient aromatic ring. This configuration enables efficient coupling in cross-coupling reactions and facilitates downstream functionalization in synthetic sequences. The aldehyde functionality provides a reactive handle for nucleophilic additions and condensation chemistry.

Application

2-Bromo-5-methylbenzaldehyde serves as a versatile building block in synthetic organic chemistry, enabling palladium-catalyzed cross-coupling reactions due to its compatible bromo and aldehyde functionalities. The methyl group enhances electronic stability and directs ortho-selective functionalization. Its bench-stable nature and compatibility with common protecting groups facilitate efficient synthesis of complex aromatic scaffolds, including those found in pharmaceutical intermediates and agrochemicals.

Synthesis

Route1
- 1048108-06-0
- ~10%
- In-stock
  
  90221-55-9
References
- Bristol-Myers Squibb Company Patent: US2008/194535 A1, 2008 ; Location in patent: Page/Page column 31 ; US 20080194535 A1
Route2
- In-stock
  
  6967-82-4
- ~92%
- In-stock
  
  90221-55-9
References
- Barbasiewicz, Michal; Blocki, Krzysztof; Malinska, Maura; Pawlowski, Robert Dalton Transactions, 2013 , vol. 42, # 2 p. 355 - 358
Route3
- In-stock
  
  727985-37-7
- ~%
- In-stock
  
  90221-55-9
References
- Wurst, Jacqueline M.; Liu, Guodong; Tan, Derek S. Journal of the American Chemical Society, 2011 , vol. 133, # 20 p. 7916 - 7925

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 17.07
LogP 2.57002
H_Acceptors 1
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

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2-Bromo-5-methylbenzaldehyde

CAS No. 90221-55-9

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