3-Bromo-4-hydroxybenzonitrile

Name: 3-Bromo-4-hydroxybenzonitrile
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CAS No. 2315-86-8
Cat. No. CS-W007522
Purity≥96%
MDL No.MFCD00143096

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Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
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3-Bromo-4-hydroxybenzonitrile|CS-W007522

Structure of 2315-86-8

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General Information

CAS No. 2315-86-8
Cat. No. CS-W007522
Purity ≥96%
MDL No. MFCD00143096
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₇H₄BrNO
Molecular Weight 198.02
Synonym(s) 2-Bromo-4-cyanophenol
SMILES C1=C(C(=CC=C1C#N)O)Br

Description

3-Bromo-4-hydroxybenzonitrile features a bromine substituent and a hydroxyl group flanking a nitrile moiety on a benzene ring, enabling diverse downstream transformations. This electron-deficient aromatic scaffold supports palladium-catalyzed cross-coupling reactions and serves as a key intermediate in the synthesis of bioactive compounds and functional materials.

Application

3-Bromo-4-hydroxybenzonitrile serves as a versatile building block in medicinal chemistry, enabling direct functionalization at the phenolic hydroxyl and brominated position. Its ortho-directed reactivity facilitates palladium-catalyzed cross-coupling and nucleophilic substitution reactions. The nitrile group offers synthetic flexibility for downstream transformations, including amidation or reduction. Bench-stable and readily purified by recrystallization, it functions effectively in standard synthetic workflows for heterocycle and API scaffold construction.

Synthesis

Route1
- 767-00-0
- ~93%
- In-stock
  
  2315-86-8
References
- CHEMO IBERICA, S.A.; CASTALDI, Graziano; RASPARINI, Marcello; SILLANI, Laura Patent: WO2010/142653 A1, 2010 ; Location in patent: Page/Page column 14 ;
Route2
- 938300-85-7
- ~83%
- In-stock
  
  2315-86-8
References
- Denton, Ross M.; An, Jie; Lindovska, Petra; Lewis, William Tetrahedron, 2012 , vol. 68, # 13 p. 2899 - 2905
Route3
- In-stock
  
  2973-78-6
- ~69%
- In-stock
  
  2315-86-8
References
- NATCO PHARMA LIMITED; Kompella, Amala; Gampa, Venue Gopala Krishna; Adibhatla, Kali Satya Bhujanga Rao; Nannapaneni, Venkaiah Chowdary Patent: US2013/172571 A1, 2013 ; Location in patent: Paragraph 0085; 0086; 0087; 0088 ;

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-P301+P310-P330-P501

Quality Control

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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

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3-Bromo-4-hydroxybenzonitrile

CAS No. 2315-86-8

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