3-Bromo-1,2,4,5-tetramethylbenzene

Name: 3-Bromo-1,2,4,5-tetramethylbenzene
Brand: ChemScene
Availability: InStock
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CAS No. 1646-53-3
Cat. No. CS-0153349
Purity≥98%
MDL No.MFCD00000070

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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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3-Bromo-1,2,4,5-tetramethylbenzene|CS-0153349

Structure of 1646-53-3

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General Information

CAS No. 1646-53-3
Cat. No. CS-0153349
Purity ≥98%
MDL No. MFCD00000070
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₀H₁₃Br
Molecular Weight 213.11
Synonym(s) Duryl bromide
SMILES CC1=CC(=C(C)C(=C1C)Br)C

Description

3-Bromo-1,2,4,5-tetramethylbenzene features a sterically hindered aromatic core with four methyl groups and a bromine substituent at the 3-position. This configuration enhances stability and facilitates selective coupling reactions in transition-metal-catalyzed transformations. The molecule’s electron-rich framework supports efficient cross-coupling under mild conditions.

Application

3-Bromo-1,2,4,5-tetramethylbenzene serves as a versatile aryl halide building block in cross-coupling reactions, particularly Suzuki and Stille couplings, due to its stability and defined substitution pattern. The bromine substituent enables reliable functionalization under standard catalytic conditions, while the tetramethyl groups provide steric shielding and enhance solubility. Its bench-stable nature and predictable reactivity make it well-suited for iterative synthesis of complex aromatic scaffolds and pharmaceutical intermediates.

Synthesis

Route1
- 95-93-2
- ~62%
- In-stock
  
  1646-54-4
- In-stock
  
  1646-53-3
References
- Organic Letters, , vol. 15, # 9 p. 2108 - 2111
Route2
- 95-93-2
- ~98%
- In-stock
  
  1646-53-3
References
- Bovonsombat; McNelis Synthesis, 1993 , # 2 p. 237 - 241

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 0
LogP 3.68278
H_Acceptors 0
H_Donors 0
Rotatable_Bonds 0

Other Classifications

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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3-Bromo-1,2,4,5-tetramethylbenzene

CAS No. 1646-53-3

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