2-Bromo-N-phenylaniline

CAS No. 61613-22-7
Cat. No. CS-0059965
Purity≥97%
MDL No.MFCD01851817

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
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Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
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General Information

CAS No. 61613-22-7
Cat. No. CS-0059965
Purity ≥97%
MDL No. MFCD01851817
Storage RT, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₂H₁₀BrN
Molecular Weight 248.12
Synonym(s) N-(2-Bromophenyl)aniline
SMILES BrC1=CC=CC=C1NC2=CC=CC=C2

Description

2-Bromo-N-phenylaniline features a bromine substituent at the ortho position relative to the aniline nitrogen, enhancing electrophilic reactivity in cross-coupling processes. The N-phenyl group imparts steric and electronic modulation, improving stability under standard conditions while enabling precise functionalization in pharmaceutical and materials synthesis.

Application

2-Bromo-N-phenylaniline serves as a versatile building block in cross-coupling chemistry, enabling efficient palladium-catalyzed C–N and C–C bond formations. Its bromine substituent provides high reactivity in Suzuki, Stille, and Buchwald–Hartwig reactions, while the aniline functionality offers moderate nucleophilicity and compatibility with common protecting groups. The compound exhibits excellent bench stability and is readily purified by recrystallization or column chromatography, facilitating its use in the synthesis of biaryl scaffolds, pharmaceutical intermediates, and functionalized heterocycles.

Synthesis

Route1
- In-stock
  
  583-55-1
- 74497-02-2
- ~96%
- In-stock
  
  61613-22-7
References
- Wheaton, Craig A.; Bow, John-Paul J.; Stradiotto, Mark Organometallics, 2013 , vol. 32, # 21 p. 6148 - 6161
Route2
- In-stock
  
  591-50-4
- 615-36-1
- ~99%
- In-stock
  
  61613-22-7
References
- Barbero, Nekane; Carril, Monica; SanMartin, Raul; Dominguez, Esther Tetrahedron, 2008 , vol. 64, # 30-31 p. 7283 - 7288
Route3
- 930-68-7
- 615-36-1
- ~91%
- In-stock
  
  61613-22-7
References
- Barros, M. Teresa; Dey, Suvendu S.; Maycock, Christopher D.; Rodrigues, Paula Chemical Communications (Cambridge, United Kingdom), 2012 , vol. 48, # 88 p. 10901 - 10903,3

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

Quality Control

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Computational Chemistry Data

TPSA 12.03
LogP 4.1927
H_Acceptors 1
H_Donors 1
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Material Science Material Composite Block Small Molecule Semiconductor Synthesis Building Block

Material Science Material Building Blocks Small Molecule Semiconductor Building Blocks Secondary Arylamines

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2-Bromo-N-phenylaniline

CAS No. 61613-22-7

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