2-Amino-3-chlorobenzonitrile

Name: 2-Amino-3-chlorobenzonitrile
Brand: ChemScene
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CAS No. 53312-77-9
Cat. No. CS-W008285
Purity≥97%
MDL No.MFCD03425881

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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 53312-77-9

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General Information

CAS No. 53312-77-9
Cat. No. CS-W008285
Purity ≥97%
MDL No. MFCD03425881
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₇H₅ClN₂
Molecular Weight 152.58
Synonym(s) benzonitrile, 2-amino-3-chloro-
SMILES NC1=C(C#N)C=CC=C1Cl

Description

2-Amino-3-chlorobenzonitrile features a strategically positioned amino group and chloro substituent on a nitrile-bearing benzene ring, enabling direct incorporation into pharmaceutical intermediates. The electron-rich amine facilitates nucleophilic coupling reactions, while the chloro handle permits palladium-catalyzed cross-coupling transformations under standard conditions. This scaffold delivers high functional group tolerance and stability during process development workflows.

Application

2-Amino-3-chlorobenzonitrile serves as a versatile building block in medicinal chemistry, enabling the synthesis of heterocyclic scaffolds via cyclization reactions. Its ortho-directed reactivity facilitates efficient functionalization, while the amino and nitrile groups offer complementary handles for further derivatization. The compound exhibits good bench stability and is compatible with standard purification methods, making it well-suited for iterative synthetic campaigns in API development.

Synthesis

Route1
- 544-92-3
- 608-31-1
- ~30%
- 63069-52-3
- In-stock
  
  53312-77-9
References
- Journal of the American Chemical Society, , vol. 125, # 47 p. 14296 - 14297
Route2
- 544-92-3
- 608-31-1
- ~31%
- In-stock
  
  53312-77-9
References
- Tetrahedron, , vol. 62, # 40 p. 9365 - 9372

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS06
Signal Word : Danger	UN#: 3439
Class : 6.1	Packing Group : Ⅲ
Hazard Statements : H302+H312-H315-H319-H331-H335
Precautionary Statements : P264-P270-P330-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 49.81
LogP 1.79388
H_Acceptors 2
H_Donors 1
Rotatable_Bonds 0

Other Classifications

Building Blocks Functional Group Chloride

Building Blocks Functional Group Cyanide/Nitrile

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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2-Amino-3-chlorobenzonitrile

CAS No. 53312-77-9

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