4-Bromo[2.2]paracyclophane

Name: 4-Bromo[2.2]paracyclophane
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 1908-61-8
Cat. No. CS-0098583
Molecule weight287.19
Purity≥95%
MDL No.None

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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 1908-61-8

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General Information

CAS No. 1908-61-8
Cat. No. CS-0098583
Purity ≥95%
MDL No. None
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₆H₁₅Br
Molecular Weight 287.19
Synonym(s) RACEMIC-4-BROMO[2,2]PARACYCLOPHANE
SMILES BrC1=C2C=CC(CCC3=CC=C(CC2)C=C3)=C1

Description

4-Bromo[2.2]paracyclophane features a rigid, strained bicyclic architecture with a bromine substituent at the para position, enabling precise spatial control in synthetic transformations. This electron-deficient platform integrates readily into cross-coupling reactions and serves as a steric probe in molecular design.

Application

4-Bromo[2.2]paracyclophane serves as a versatile building block in synthetic organic chemistry, offering a rigid, electron-deficient aromatic scaffold ideal for transition-metal-catalyzed cross-coupling reactions. The bromine substituent enables reliable Suzuki, Stille, and Negishi couplings, facilitating the construction of complex biaryl architectures. Its structural integrity and bench stability enhance utility in multi-step synthesis and medicinal chemistry campaigns requiring defined molecular topology.

Synthesis

Route1
- In-stock
  
  1633-22-3
- ~99%
- In-stock
  
  1908-61-8
References
- Parmar, Rakesh; Coles, Martyn P.; Hitchcock, Peter B.; Rowlands, Gareth J. Synthesis, 2010 , # 24 art. no. P12510SS, p. 4177 - 4187
Route2
- 735-65-9
- ~62%
- In-stock
  
  1908-61-8
References
- Mamyrbekova, Zh. A.; Bekro, Iv. A.; Soldatova, S. A.; Ageev, E. A.; Guryshev, V. N.; Soldatenkov, A. T. Pharmaceutical Chemistry Journal, 1994 , vol. 28, # 3 p. 203 - 208 Khimiko-Farmatsevticheskii Zhurnal, 1994 , vol. 28, # 3 p. 52 - 56

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 0
LogP 4.3329
H_Acceptors 0
H_Donors 0
Rotatable_Bonds 0

Key Words

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4-Bromo[2.2]paracyclophane

CAS No. 1908-61-8

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