4-Amino-3-bromobenzonitrile

Name: 4-Amino-3-bromobenzonitrile
Brand: ChemScene
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CAS No. 50397-74-5
Cat. No. CS-W002840
Purity≥97%
MDL No.MFCD01861386

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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 50397-74-5

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General Information

CAS No. 50397-74-5
Cat. No. CS-W002840
Purity ≥97%
MDL No. MFCD01861386
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₇H₅BrN₂
Molecular Weight 197.03
Synonym(s) Benzonitrile, 4-amino-3-bromo-
SMILES N#Cc1ccc(c(c1)Br)N

Description

4-Amino-3-bromobenzonitrile features a bromine atom at the meta position relative to a nitrile group, paired with an amino substituent ortho to the nitrile. This electron-rich scaffold enables direct coupling in cross-coupling reactions and serves as a key intermediate in pharmaceutical synthesis. The molecule exhibits enhanced solubility in polar solvents and stability under standard bench conditions.

Application

4-Amino-3-bromobenzonitrile serves as a versatile building block in medicinal chemistry, enabling palladium-catalyzed cross-coupling reactions due to its compatible bromo and nitrile functionalities. The amino group provides a handle for derivatization, while the nitrile offers synthetic flexibility for downstream transformations. Its bench-stable nature and compatibility with standard protecting group strategies facilitate efficient synthesis of heterocyclic scaffolds and API intermediates.

Synthesis

Route1
- In-stock
  
  873-74-5
- ~96%
- In-stock
  
  50397-74-5
References
- Alinezhad, Heshmatollah; Tavakkoli, Sahar Mohseni; Salehian, Fatemeh Synthetic Communications, 2010 , vol. 40, # 21 p. 3226 - 3232
Route2
- In-stock
  
  619-72-7
- ~%
- In-stock
  
  50397-74-5
References
- Illig, Carl R.; Manthey, Carl L.; Meegalla, Sanath K.; Wall, Mark J.; Chen, Jinsheng; Wilson, Kenneth J.; Desjarlais, Renee L.; Ballentine, Shelley K.; Schubert, Carsten; Crysler, Carl S.; Chen, Yanmin; Molloy, Christopher J.; Chaikin, Margery A.; Donatelli, Robert R.; Yurkow, Edward; Zhou, Zhao; Player, Mark R.; Tomczuk, Bruce E. Bioorganic and Medicinal Chemistry Letters, 2013 , vol. 23, # 23 p. 6363 - 6369

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-H317
Precautionary Statements : P261-P264-P270-P272-P280-P302+P352-P330-P362+P364-P501

Quality Control

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Computational Chemistry Data

TPSA 49.81
LogP 1.90298
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

Key Words

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4-Amino-3-bromobenzonitrile

CAS No. 50397-74-5

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