5-Bromo-2-naphthonitrile

Name: 5-Bromo-2-naphthonitrile
Brand: ChemScene
Availability: InStock
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CAS No. 556107-64-3
Cat. No. CS-0155713
Purity≥97%
MDL No.MFCD17012556

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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 556107-64-3

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General Information

CAS No. 556107-64-3
Cat. No. CS-0155713
Purity ≥97%
MDL No. MFCD17012556
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₁H₆BrN
Molecular Weight 232.08
Synonym(s) 5-Bromonaphthalene-2-carbonitrile
SMILES C1=CC2=C(C=CC(=C2)C#N)C(=C1)Br

Description

5-Bromo-2-naphthonitrile features a naphthalene core with bromine at the 5-position and a nitrile group at the 2-position, delivering high reactivity for cross-coupling and functionalization. This electron-deficient scaffold enables efficient derivatization in synthetic routes targeting pharmaceutical intermediates and advanced materials.

Application

5-Bromo-2-naphthonitrile serves as a versatile building block in synthetic organic chemistry, enabling palladium-catalyzed cross-coupling reactions and nucleophilic substitution processes. Its nitrile group provides a handle for selective transformations, while the bromo substituent facilitates C–C bond formation under standard Suzuki, Stille, or Negishi conditions. The molecule exhibits good bench stability and is readily purified by recrystallization, making it suitable for scale-up and multi-step synthesis of functionalized naphthalene derivatives used in pharmaceutical and materials research.

Synthesis

Route1
- In-stock
  
  1013-83-8
- 124-63-0
- ~%
- In-stock
  
  556107-64-3
References
- Agejas-Chicharro, Javier; Belen Bueno Melendo, Ana; Camp, Nicholas Paul; Gilmore, Jeremy; Jimenez-Aguado, Alma Maria; Lamas-Peteira, Carlos; Marcos-Llorente, Alicia; Mazanetz, Michael Philip; Montero Salgado, Carlos; Timms, Graham Henry; Williams, Andrew Caerwyn Patent: US2004/122001 A1, 2004 ; US 20040122001 A1
Route2
- In-stock
  
  613-46-7
- ~%
- In-stock
  
  556107-64-3
References
- Hausamann Chemische Berichte, 1876 , vol. 9, p. 1519

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H315-H319
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P361-P405-P501

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Computational Chemistry Data

TPSA 23.79
LogP 3.47398
H_Acceptors 1
H_Donors 0
Rotatable_Bonds 0

Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic ring compounds Naphthalene compounds

Key Words

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5-Bromo-2-naphthonitrile

CAS No. 556107-64-3

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