2000-93-3

Basic information

• Product Name: 3-Amino-4-chlor-1-hexyl-benzol
• CAS NO: 2000-93-3
• Molecular Weight: 211.735
• Mol File: 2000-93-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 3-Amino-4-chlor-1-hexyl-benzol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Amino-4-chlor-1-hexyl-benzol(2000-93-3)
• EPA Substance Registry System: 3-Amino-4-chlor-1-hexyl-benzol(2000-93-3)

Safety Data

• Hazardous Substances Data: 2000-93-3(Hazardous Substances Data)

Upstream product

• 60811-17-8 5-bromo-2-chloroaniline 
• 21369-64-2 n-hexyllithium 
• 449758-17-2 1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole 

Relevant articles and documents

Development of a Scalable Negishi Cross-Coupling Process for the Preparation of 2-Chloro-5-(1-(tetrahydro-2 H-pyran-2-yl)-1 H-pyrazol-5-yl)aniline

A scalable synthesis of 2-chloro-5-(1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl)aniline (1), a key intermediate in the synthesis of an immuno-oncology asset, is described. A Negishi cross-coupling between in situ generated heteroaryl zinc reagent 4 and 5-bromo-2-chloroaniline (3) catalyzed by Pd(Xantphos)Cl2 enabled the construction of the key aryl-heteroaryl bond. A scalable first-generation process was developed that delivered 1 in multikilogram quantities. Building upon knowledge from the initial process, a more efficient workup and isolation procedure was developed that controlled levels of residual Pd and Zn to consistent levels that were acceptable for downstream processing. The high-yielding optimized process offers streamlined metals remediation, a 30% reduction in the number of unit operations, and a 34% reduction in process mass intensity (PMI) compared to the initial process.