2-Bromo-4,6-dimethylphenol

Name: 2-Bromo-4,6-dimethylphenol
Brand: ChemScene
Availability: InStock
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CAS No. 15191-36-3
Cat. No. CS-0153366
Purity≥97%
MDL No.MFCD08443978

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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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Structure of 15191-36-3

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General Information

CAS No. 15191-36-3
Cat. No. CS-0153366
Purity ≥97%
MDL No. MFCD08443978
Storage RT, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₈H₉BrO
Molecular Weight 201.06
Synonym(s) 2-BROMO-4,6-DIMETHYLBENZENOL
SMILES CC1=CC(=C(C(=C1)Br)O)C

Description

2-Bromo-4,6-dimethylphenol features a bromine substituent at the ortho position relative to the phenolic hydroxyl, combined with methyl groups at the 4- and 6-positions. This substitution pattern imparts enhanced stability and steric shielding around the reactive site. The compound serves as a selective electrophilic reagent in aromatic coupling reactions, particularly in the synthesis of functionalized heterocycles and advanced intermediates for agrochemicals and pharmaceuticals.

Application

2-Bromo-4,6-dimethylphenol serves as a versatile building block in synthetic organic chemistry, enabling efficient access to substituted aromatic systems via palladium-catalyzed cross-coupling reactions. Its bromine substituent exhibits high reactivity in Suzuki, Stille, and Negishi couplings, while the ortho-methyl groups provide steric protection and enhance bench stability. The phenolic hydroxyl group allows for selective derivatization, facilitating the construction of functionalized heterocycles and complex scaffolds relevant to medicinal chemistry and materials science.

Synthesis

Route1
- 105-67-9
- ~99%
- In-stock
  
  15191-36-3
References
- Azarifar, Davood; Khosravi, Kaveh; Najminejad, Zohreh; Soleimani, Khadijeh Journal of the Iranian Chemical Society, 2012 , vol. 9, # 3 p. 321 - 326
Route2
- In-stock
  
  556-96-7
- ~%
- In-stock
  
  2374-05-2
- In-stock
  
  15191-36-3
References
- Nature, , vol. 499, # 7457 p. 192 - 196
Route3
- 67-56-1
- 105-67-9
- ~60%
- In-stock
  
  15191-36-3
- 58661-34-0
References
- Angewandte Chemie - International Edition, , vol. 44, # 2 p. 310 - 313

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 20.23
LogP 2.77154
H_Acceptors 1
H_Donors 1
Rotatable_Bonds 0

Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

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2-Bromo-4,6-dimethylphenol

CAS No. 15191-36-3

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