2-Amino-5-chloropyridine Chemical Properties

Melting point:

135-138 °C (lit.)

Boiling point:

127-128 °C/11 mmHg (lit.)

Density 

1.2417 (rough estimate)

refractive index 

1.5110 (estimate)

Flash point:

160 °C

storage temp. 

2-8°C

solubility 

1.0g/l

pka

4.67±0.13(Predicted)

form 

Crystalline Powder

color 

Beige to beige-brown

Water Solubility 

1 g/L (20 ºC)

BRN 

108735

InChIKey

MAXBVGJEFDMHNV-UHFFFAOYSA-N

CAS DataBase Reference

1072-98-6(CAS DataBase Reference)

NIST Chemistry Reference

2-Amino-5-chloropyridine(1072-98-6)

EPA Substance Registry System

2-Amino-5-chloropyridine (1072-98-6)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-36/37/38

Safety Statements 

22-24/25-37/39-26-36

WGK Germany 

3

Hazard Note 

Harmful

HazardClass 

IRRITANT

HS Code 

29333999

MSDS

• Language:English Provider:2-Amino-5-chloropyridine
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2-Amino-5-chloropyridine Usage And Synthesis

Chemical Properties

beige to beige-brown crystalline powder

Uses

5-Chloro-2-pyridinamine is a useful synthetic intermediate. It can be used to synthesize zopiclone (Z700500) which is a cyclopyrrolone member of a family of non-benzodiazepine GABAA receptor agonists.

Reactions

2-Amino-5-chloropyridine can be used to electro-organically synthesize 6-aminonicotinic acid. 6-aminonicotinic acid is the main component of vitamin B3 and can be used to treat pellagra. The specific method is as follows:
In the presence of sulfuric acid and carbon dioxide, in dimethylformamide (DMF) solution, 5-chloro-2-nitropyridine 1 is electrochemically converted to 2-amino-5-chloropyridine 2 on a nickel cathode and a copper anode at an apparent current density of 10 mA/cm2 using a diaphragmless electrolytic cell, with a yield of up to 84%. Then 2 is reductively carboxylated to synthesize 6-aminonicotinic acid 3 on the cathode surface with a yield of 78%.

Synthesis Reference(s)

The Journal of Organic Chemistry, 41, p. 93, 1976 DOI: 10.1021/jo00863a020

Toxicology

2-Amino-5-chloropyridine is an irritant, causing severe eye irritation, possibly skin and respiratory irritation, and harmful if ingested. The substance is non-mutagenic, but has a relatively high toxicity to zebrafish embryonic development, with embryonic malformation and mortality rates being concentration-dependent.

Purification Methods

Recrystallise this base from pet ether. It sublimes at 50o/0.5mm. [Beilstein 22 II 332, 22/8 V 541.]

2-Amino-5-chloropyridine(1072-98-6)Related Product Information

• Pentachloropyridine
• Glycine
• Clopidol
• 2-Aminopyridine
• ALTRENOGEST
• 3-Aminopyridine
• 4-Dimethylaminopyridine
• 6-Aminocaproic acid
• 2-Chloro-3-cyanopyridine
• EthanediaMide iMpurity D
• 4,5,6,7-tetrahydro-5-methylthiazolo[5,4-c]pyridin-2-amine dihydrobromide
• Edoxaban Impurity 29
• INDEX NAME NOT YET ASSIGNED
• 2-Aminophenol
• Tris(hydroxymethyl)aminomethane
• 2-AMINO-6-CHLOROPYRIDINE (6-CHLOROPYRIDIN-2-YLAMINE),6-AMINO-2-CHLOROPYRIDINE
• 2-AMINO-3-CHLOROPYRIDINE
• 2-Amino-4-chloropyridine