(4-Bromo-3,5-dimethylphenyl)methanol

Name: (4-Bromo-3,5-dimethylphenyl)methanol
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CAS No. 27006-02-6
Cat. No. CS-0195158
Molecule weight215.09
Purity≥95%
MDL No.None

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(4-Bromo-3,5-dimethylphenyl)methanol|CS-0195158

Structure of 27006-02-6

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General Information

CAS No. 27006-02-6
Cat. No. CS-0195158
Purity ≥95%
MDL No. None
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₉H₁₁BrO
Molecular Weight 215.09
Synonym(s) 4-BroMo-3,5-diMethylbenzyl alcohol
SMILES CC1=C(C(=CC(=C1)CO)C)Br

Description

This boronate moiety integrates a sterically hindered aryl scaffold with dual methyl groups flanking a bromo substituent, enabling selective cross-coupling under standard conditions. The hydroxymethyl functionality provides a handle for downstream derivatization and enhances solubility in polar solvents.

Application

(4-Bromo-3,5-dimethylphenyl)methanol serves as a versatile building block in medicinal chemistry and materials synthesis, offering a brominated aryl methyl alcohol functionality. Its bench-stable nature and tolerance to common reaction conditions enable straightforward derivatization via nucleophilic substitution or coupling reactions. The ortho-methyl groups provide steric protection and enhance metabolic stability, making it suitable for constructing complex heterocyclic scaffolds and functionalized aromatic intermediates.

Synthesis

Route1
- 74973-54-9
- ~99%
- In-stock
  
  27006-02-6
References
- Kawate, Tomohiko; Iwase, Noriaki; Shimizu, Motohisa; Stanley, Sarah A.; Wellington, Samantha; Kazyanskaya, Edward; Hung, Deborah T. Bioorganic and Medicinal Chemistry Letters, 2013 , vol. 23, # 22 p. 6052 - 6059
Route2
- In-stock
  
  576-83-0
- ~54%
- In-stock
  
  27006-02-6
References
- Wessig, Pablo; Teubner, Janek Synlett, 2006 , # 10 p. 1543 - 1546
Route3
- In-stock
  
  7697-32-7
- ~%
- In-stock
  
  27006-02-6
References
- Grisdale,P.J. et al. Journal of Organic Chemistry, 1971 , vol. 36, p. 544 - 549

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
Precautionary Statements : P264-P270-P330-P501

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Computational Chemistry Data

TPSA 20.23
LogP 2.55824
H_Acceptors 1
H_Donors 1
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-3,5-dimethylphenyl)methanol

CAS No. 27006-02-6

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