3-Amino-4-methoxybenzonitrile

Name: 3-Amino-4-methoxybenzonitrile
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CAS No. 60979-25-1
Cat. No. CS-W021835
Purity≥97%
MDL No.MFCD09745274

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
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3-Amino-4-methoxybenzonitrile|CS-W021835

Structure of 60979-25-1

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General Information

CAS No. 60979-25-1
Cat. No. CS-W021835
Purity ≥97%
MDL No. MFCD09745274
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₈H₈N₂O
Molecular Weight 148.16
Synonym(s) 2-Amino-4-cyanoanisole
SMILES N#CC1=CC=C(OC)C(N)=C1

Description

3-Amino-4-methoxybenzonitrile features a strategically positioned amino group and methoxy substituent on a benzonitrile scaffold, enabling selective coupling reactions in pharmaceutical synthesis. The electron-donating methoxy group enhances reactivity at the para position relative to the nitrile, while the amino functionality offers direct handle for derivatization. This compound serves as a key intermediate in developing bioactive heterocycles and functional materials.

Application

3-Amino-4-methoxybenzonitrile serves as a versatile building block in medicinal chemistry, enabling the construction of heterocyclic scaffolds through cyclization and coupling reactions. Its ortho-diamino-nitrile motif facilitates efficient transition-metal-catalyzed transformations, while the methoxy group enhances solubility and modulates electronic properties. Bench-stable and amenable to standard purification methods, it functions reliably in multi-step syntheses for API development.

Synthesis

Route1
- In-stock
  
  33224-23-6
- ~97%
- In-stock
  
  60979-25-1
References
- Bakunov, Stanislav A.; Bakunova, Svetlana M.; Wenzler, Tanja; Ghebru, Maedot; Werbovetz, Karl A.; Brun, Reto; Tidwell, Richard R. Journal of Medicinal Chemistry, 2010 , vol. 53, # 1 p. 254 - 272
Route2
- 939-80-0
- 124-41-4
- ~%
- In-stock
  
  60979-25-1
References
- Recueil des Travaux Chimiques des Pays-Bas, , vol. 66, p. 369 Chem.Abstr., , vol. 42, p. 148

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-H319
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

TPSA 59.04
LogP 1.14908
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Cyanide/Nitrile

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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3-Amino-4-methoxybenzonitrile

CAS No. 60979-25-1

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