2-Bromo-5-hydroxybenzonitrile

Name: 2-Bromo-5-hydroxybenzonitrile
Brand: ChemScene
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CAS No. 189680-06-6
Cat. No. CS-W019014
Purity≥97%
MDL No.MFCD08061922

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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+
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2-Bromo-5-hydroxybenzonitrile|CS-W019014

Structure of 189680-06-6

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General Information

CAS No. 189680-06-6
Cat. No. CS-W019014
Purity ≥97%
MDL No. MFCD08061922
Storage RT, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₇H₄BrNO
Molecular Weight 198.02
Synonym(s) 2-BroMo-5-hydroxybenzonitrle
SMILES BrC1=C(C#N)C=C(C=C1)O

Description

2-Bromo-5-hydroxybenzonitrile features a hydroxyl group flanked by bromine and nitrile substituents on a benzene ring, enabling selective functionalization in synthetic sequences. This electron-deficient scaffold supports efficient coupling reactions under mild conditions, offering high stability during intermediate processing. The molecule integrates readily into pharmaceutical and agrochemical scaffolds where halogenated phenolic motifs are required.

Application

2-Bromo-5-hydroxybenzonitrile serves as a versatile building block in medicinal chemistry, enabling direct functionalization at the hydroxyl and nitrile positions. Its bromine atom facilitates Suzuki-Miyaura and Stille couplings, while the phenolic OH allows for etherification or esterification. The nitrile group provides a handle for reductive amination or hydrolysis to carboxylic acids. Bench-stable and amenable to purification by recrystallization, it functions effectively in multi-step syntheses of heterocyclic scaffolds and bioactive molecules.

Synthesis

Route1
- In-stock
  
  873-62-1
- ~22%
- In-stock
  
  189680-06-6
References
- SANOFI-AVENTIS; GEORGE, Pascal; HALL, Daniel; HARTUNG, Ryan; KOSLEY, JR., Raymond W.; SCOTESE, Anthony C. Patent: WO2011/34828 A1, 2011 ; Location in patent: Page/Page column 80 ; WO 2011/034828 A1

Safety Information

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GHS Pictogram :	GHS No : GHS06
Signal Word : Danger	UN#: 3439
Class : 6.1	Packing Group : Ⅲ
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 44.02
LogP 2.02638
H_Acceptors 2
H_Donors 1
Rotatable_Bonds 0

Other Classifications

Building Blocks Functional Group Cyanide/Nitrile

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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2-Bromo-5-hydroxybenzonitrile

CAS No. 189680-06-6

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