4-Bromo-5-chloro-2-nitroaniline

Name: 4-Bromo-5-chloro-2-nitroaniline
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 827-33-8
Cat. No. CS-W005851
Purity≥96%
MDL No.MFCD11100159

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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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4-Bromo-5-chloro-2-nitroaniline|CS-W005851

Structure of 827-33-8

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General Information

CAS No. 827-33-8
Cat. No. CS-W005851
Purity ≥96%
MDL No. MFCD11100159
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₆H₄BrClN₂O₂
Molecular Weight 251.47
Synonym(s) 4-bromo-5-chloro-2-nitrophenylamine
SMILES NC1=CC(Cl)=C(Br)C=C1[N+]([O-])=O

Description

4-Bromo-5-chloro-2-nitroaniline features a highly functionalized aromatic core with complementary halogen and nitro groups, enabling direct coupling in cross-coupling reactions. The electron-deficient ring facilitates nucleophilic substitution, while the ortho-halogen positions support selective Pd-catalyzed transformations. This compound serves as a key intermediate in the synthesis of advanced pharmaceuticals and agrochemicals requiring precise substitution patterns.

Application

4-Bromo-5-chloro-2-nitroaniline serves as a versatile building block for the synthesis of heterocyclic scaffolds and functionalized aromatic compounds. Its complementary halogen and nitro groups enable sequential cross-coupling, nucleophilic substitution, and reduction strategies under standard reaction conditions. The molecule exhibits bench stability and facilitates straightforward purification, making it well-suited for iterative medicinal chemistry campaigns and API intermediate development.

Synthesis

Route1
- In-stock
  
  1635-61-6
- ~77%
- In-stock
  
  827-33-8
References
- BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; BAeRFACKER, Lars; KAST, Raimund; GRIEBENOW, Nils; MEIER, Heinrich; KOLKHOF, Peter; ALBRECHT-KUePPER, Barbara; NITSCHE, Adam; STASCH, Johannes-Peter; SCHNEIDER, Dirk; TEUSCH, Nicole; RUDOLPH, Joachim; WHELAN, James; BULLOCK, William; PLEASIC-WILLIAMS, Susan Patent: WO2010/20363 A1, 2010 ; Location in patent: Page/Page column 78-79 ;
Route2
- 956282-97-6
- ~%
- In-stock
  
  827-33-8
References
- US2007/259936 A1, ; Page/Page column 176 ; US 20070259936 A1
Route3
- 716-66-5
- ~95%
- In-stock
  
  827-33-8
References
- Britton, Doyle; Noland, Wayland E.; Pinnow, Matthew J.; Young Jr., Victor G. Helvetica Chimica Acta, 2003 , vol. 86, # 4 p. 1175 - 1192

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 69.16
LogP 2.5929
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Chloride

Building Blocks Functional Group Nitro compounds

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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4-Bromo-5-chloro-2-nitroaniline

CAS No. 827-33-8

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