3-Bromo-5-methoxyphenol

Name: 3-Bromo-5-methoxyphenol
Brand: ChemScene
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CAS No. 855400-66-7
Cat. No. CS-0030499
Purity≥98%
MDL No.MFCD12405420

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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 855400-66-7

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General Information

CAS No. 855400-66-7
Cat. No. CS-0030499
Purity ≥98%
MDL No. MFCD12405420
Storage RT, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₇H₇BrO₂
Molecular Weight 203.03
Synonym(s) 3-Brom-5-methoxy-phenol
SMILES OC1=CC(OC)=CC(Br)=C1

Description

3-Bromo-5-methoxyphenol features a bromine substituent at the meta position relative to a hydroxyl group, combined with a methoxy group at the para position, creating a uniquely activated aromatic scaffold. This electronic configuration enables selective coupling reactions in cross-coupling and functionalization workflows. The compound exhibits enhanced solubility in organic solvents and stability under standard bench conditions, facilitating its use in synthetic pathways requiring precise regiocontrol.

Application

3-Bromo-5-methoxyphenol serves as a versatile building block in medicinal chemistry and materials science, enabling direct functionalization via palladium-catalyzed cross-coupling reactions. Its bromine and phenolic hydroxyl groups offer orthogonal reactivity for sequential modifications, while the methoxy group enhances solubility and modulates electronic properties. Bench-stable and readily purified by recrystallization, it functions efficiently in Suzuki, Stille, and Negishi couplings, facilitating rapid access to substituted aromatic scaffolds relevant to pharmaceutical and agrochemical development.

Synthesis

Route1
- In-stock
  
  20469-65-2
- ~86%
- In-stock
  
  855400-66-7
References
- Daiichi Sankyo Company, Limited Patent: EP2239253 A1, 2010 ; Location in patent: Page/Page column 44 ; EP 2239253 A1
Route2
- In-stock
  
  16618-68-1
- ~%
- In-stock
  
  855400-66-7
References
- Hodgson; Wignall Journal of the Chemical Society, 1926 , p. 2827

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 29.46
LogP 2.1633
H_Acceptors 2
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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3-Bromo-5-methoxyphenol

CAS No. 855400-66-7

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