4-Amino-3-bromo-5-nitrobenzonitrile

Name: 4-Amino-3-bromo-5-nitrobenzonitrile
Brand: ChemScene
Availability: InStock
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CAS No. 1239720-33-2
Cat. No. CS-0188052
Purity≥95%
MDL No.MFCD22383659

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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-Amino-3-bromo-5-nitrobenzonitrile|CS-0188052

Structure of 1239720-33-2

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General Information

CAS No. 1239720-33-2
Cat. No. CS-0188052
Purity ≥95%
MDL No. MFCD22383659
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₇H₄BrN₃O₂
Molecular Weight 242.03
Synonym(s) None
SMILES C1=C(C=C(C(=C1Br)N)[N+](=O)[O-])C#N

Description

4-Amino-3-bromo-5-nitrobenzonitrile features a strategically positioned nitro group and electron-deficient aromatic core, enabling direct incorporation into Suzuki-Miyaura cross-coupling reactions. The amino functionality facilitates downstream derivatization, while the bromine serves as a reliable coupling handle. This compound offers enhanced stability under standard conditions and is compatible with diverse reaction environments in synthetic organic chemistry workflows.

Application

4-Amino-3-bromo-5-nitrobenzonitrile serves as a versatile building block in medicinal chemistry and agrochemical synthesis, enabling efficient construction of substituted heterocycles via cyclization or coupling reactions. The molecule combines ortho-directed reactivity from the amino and nitrile groups with the electrophilic bromine site, facilitating palladium-catalyzed cross-couplings. Its bench-stable nature and compatibility with diverse functional groups make it well-suited for multi-step synthetic sequences in API development.

Synthesis

Route1
- In-stock
  
  6393-40-4
- ~35%
- In-stock
  
  1239720-33-2
References
- WO2010/89292 A1, ; Page/Page column 93-94 ; WO 2010/089292 A1

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-H312-H315-H319-H332-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 92.95
LogP 1.81118
H_Acceptors 4
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Cyanide/Nitrile

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-Amino-3-bromo-5-nitrobenzonitrile

CAS No. 1239720-33-2

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