4-Bromo-2,6-dimethylbenzaldehyde

Name: 4-Bromo-2,6-dimethylbenzaldehyde
Brand: ChemScene
Availability: InStock
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CAS No. 5769-33-5
Cat. No. CS-0028756
Purity≥98%
MDL No.MFCD11227151

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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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4-Bromo-2,6-dimethylbenzaldehyde|CS-0028756

Structure of 5769-33-5

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General Information

CAS No. 5769-33-5
Cat. No. CS-0028756
Purity ≥98%
MDL No. MFCD11227151
Storage 4°C, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₉H₉BrO
Molecular Weight 213.07
Synonym(s) 2,6-Dimethyl-4-bromobenzaldehyde
SMILES O=CC1=C(C)C=C(Br)C=C1C

Description

4-Bromo-2,6-dimethylbenzaldehyde features a sterically hindered aromatic core with electron-withdrawing bromine and electron-donating methyl groups, enabling selective functionalization. The aldehyde moiety facilitates efficient coupling reactions, while the ortho-methyl substitution enhances stability under standard conditions. This compound serves as a key building block in synthesizing bioactive molecules and advanced materials.

Application

4-Bromo-2,6-dimethylbenzaldehyde serves as a valuable building block in medicinal chemistry and agrochemical synthesis, offering enhanced steric shielding and electronic modulation via its ortho-methyl groups. The aldehyde functionality enables reliable transformations in reductive amination, Wittig reactions, and coupling processes, while the bromine substituent facilitates subsequent cross-coupling reactions such as Suzuki or Stille couplings. Bench-stable and readily purified by recrystallization, it functions as a versatile scaffold for constructing complex aromatic systems with controlled regiochemistry.

Synthesis

Route1
- In-stock
  
  5757-66-4
- ~88%
- In-stock
  
  5769-33-5
References
- Nakayama; Khorana Journal of Organic Chemistry, 1990 , vol. 55, # 16 p. 4953 - 4955
Route2
- 4885-02-3
- In-stock
  
  556-96-7
- ~19%
- In-stock
  
  5769-33-5
- 88174-53-2
References
- Ohsawa, Kosuke; Yoshida, Masahito; Doi, Takayuki Journal of Organic Chemistry, 2013 , vol. 78, # 7 p. 3438 - 3444

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

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Computational Chemistry Data

TPSA 17.07
LogP 2.87844
H_Acceptors 1
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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4-Bromo-2,6-dimethylbenzaldehyde

CAS No. 5769-33-5

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