2-Amino-4-methoxybenzothiazole

Name: 2-Amino-4-methoxybenzothiazole
Brand: ChemScene
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CAS No. 5464-79-9
Cat. No. CS-0054537
Purity≥97%
MDL No.None

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2-Amino-4-methoxybenzothiazole|CS-0054537

Structure of 5464-79-9

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General Information

CAS No. 5464-79-9
Cat. No. CS-0054537
Purity ≥97%
MDL No. None
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₈H₈N₂OS
Molecular Weight 180.23
Synonym(s) 4-methoxybenzothiazol-2-ylamine
SMILES C1=CC=C(C2=C1SC(=N2)N)OC

Description

2-Amino-4-methoxybenzothiazole features a benzothiazole core functionalized with an amino group at the 2-position and a methoxy substituent at the 4-position, delivering enhanced electron density and solubility. This combination enables efficient integration into fluorescent probes and bioactive scaffolds, particularly in photostable dye development and targeted protein labeling applications.

Application

2-Amino-4-methoxybenzothiazole serves as a versatile building block for heterocyclic scaffolds, enabling efficient access to biologically relevant benzothiazole derivatives. Its amino and methoxy groups offer orthogonal reactivity for selective functionalization, while the core structure exhibits robust bench stability and compatibility with standard coupling reactions. The compound facilitates rapid diversification in medicinal chemistry campaigns targeting kinase inhibitors and fluorescent probes.

Synthesis

Route1
- In-stock
  
  1516-37-6
- ~70%
- In-stock
  
  5464-79-9
References
- Sharma, Pratibha; Kumar, Ashok; Kumari, Prerna; Singh, Jitendra; Kaushik Medicinal Chemistry Research, 2012 , vol. 21, # 7 p. 1136 - 1148
Route2
- 333-20-0
- 90-04-0
- ~92%
- In-stock
  
  5464-79-9
References
- Telvekar, Vikas N.; Bachhav, Harshal M.; Bairwa, Vinod Kumar Synlett, 2012 , vol. 23, # 15 p. 2219 - 2222
Route3
- 1147550-11-5
- 90-04-0
- ~67%
- In-stock
  
  5464-79-9
References
- Patel, Navin B.; Agravat, Suresh N.; Shaikh, Faiyazalam M. Medicinal Chemistry Research, 2011 , vol. 20, # 7 p. 1033 - 1041

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+H332
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P501

Quality Control

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Computational Chemistry Data

TPSA 48.14
LogP 1.8871
H_Acceptors 4
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds Benzothiazole compounds

Key Words

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2-Amino-4-methoxybenzothiazole

CAS No. 5464-79-9

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