2-amino-5-chloronicotinaldehyde

Base Information

• Chemical Name: 2-amino-5-chloronicotinaldehyde
• CAS No.: 54856-61-0
• Molecular Formula: C6H5ClN2O
• Molecular Weight: 156.572
• Hs Code.: 2933399090
• Mol file: 54856-61-0.mol

Synonyms:2-Amino-5-chloropyridine-3-carbaldehyde;2-Amino-5-chloronicotinaldehyde;

Chemical Property of 2-amino-5-chloronicotinaldehyde

Chemical Property:

• Vapor Pressure: 0.001mmHg at 25°C
• Melting Point: 169-171°
• Refractive Index: 1.663
• Boiling Point: 301.877 °C at 760 mmHg
• Flash Point: 136.371 °C
• PSA: 55.98000
• Density: 1.442 g/cm³
• LogP: 1.71090
• Storage Temp.: 2-8°C

Purity/Quality:

99%, ^*data from raw suppliers

2-Amino-5-chloronicotinaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 2-Amino-5-chloronicotinaldehyde is an intermediate used to prepare benzopyrancarboxylates and quinolinecarboxylates as cyclooxygenase-2 inhibitors.

Technology Process of 2-amino-5-chloronicotinaldehyde

There total 5 articles about 2-amino-5-chloronicotinaldehyde which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.6%

2-Aminonicotinaldehyde (7521-41-7) → 2-amino-5-chloropyridine-3-carboxaldehyde (54856-61-0)

Guidance literature:

With N-chloro-succinimide; In acetonitrile; for 1.5h; Reflux;

Reference yield: 68.0%

→ 2-amino-5-chloropyridine-3-carboxaldehyde (54856-61-0)

Guidance literature:

Reference yield:

2-aminopyridine (504-29-0) → 2-amino-5-chloropyridine-3-carboxaldehyde (54856-61-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: tert-butyl alcohol / 30 - 40 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

2.2: -78 - -20 °C / Inert atmosphere

2.3: -78 - 20 °C / Inert atmosphere

3.1: trifluoroacetic acid / dichloromethane / 20 °C / Inert atmosphere

4.1: N-chloro-succinimide / acetonitrile / 2 h / Reflux; Inert atmosphere

With N-chloro-succinimide; n-butyllithium; trifluoroacetic acid; In tetrahydrofuran; hexane; dichloromethane; acetonitrile; tert-butyl alcohol;

DOI:10.1515/HC.2011.004

upstream raw materials:

2-Aminonicotinaldehyde

2-aminopyridine

N-(tert-butoxycarbonyl)-2-aminopyridine

2--3-pyridinecarboxaldehyde

Downstream raw materials:

(2-amino-5-chloro-3-pyridyl)-[1-[4-chloro-3-(trifluoromethyl)phenyl]pyrazol-4-yl]methanol

Refernces

• 1、 Hou, Chuan-Jin,Guo, Wei-Lei,Liu, Xiao-Ning,Yang, Da-Wei. "An efficient synthesis of 2-amino-5-chloro-3-pyridinecarbox-aldehyde and 5-amino-2-chloro-4-pyridinecarboxaldehyde". experimental part. p. 21 - 23. Retrieved 2011/10/02.
• 2、 -. "Substituted benzopyran derivatives for the treatment of inflammation". . . Retrieved 2008/06/13.