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6-Chloro-2-pyridinamine

6-Chloro-2-pyridinamine structure

CAS No:
45644-21-1
Formula:
C5H5ClN2
Chemical Name:
6-Chloro-2-pyridinamine
Synonyms:
2-Pyridinamine,6-chloro-;Pyridine,2-amino-6-chloro-;6-Chloro-2-pyridinamine;2-Amino-6-chloropyridine;2-Chloro-6-aminopyridine;6-Amino-2-chloropyridine;(6-Chloropyridin-2-yl)amine;6-Chloro-2-aminopyridine
Categories:
Organic Chemistry > Organic Fluorine Compound

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Description

White to light yellow powder

6-Chloro-2-pyridinamine Basic Attributes

Molecular Weight：

128.56

Exact Mass：

128.56

BRN：

108669

EC Number：

-0

DSSTox ID：

DTXSID20196575

HScode：

2933399090

Characteristics

PSA：

38.9

XLogP3：

0.8

Appearance：

Orange to light brown Powder or Low Melting Solid

Density：

1.3±0.1 g/cm3

Melting Point：

75 °C

Boiling Point：

255.7°C at 760 mmHg

Flash Point：

108.5±21.8 °C

Refractive Index：

1.607

Safety Information

Hazard category：

IRRITANT

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

22-36/37/38

safety instructions：

26-36/37-36

RTECS Number：

US1813350

Marks：

Xn,Xi

Hazard note：

Harmful/Irritant

Precautionary statement(s)：

P261-P305 + P351 + P338

Hazard Statements：

H302-H315-H319-H335

GHS Classification：

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 202 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

6-Chloro-2-pyridinamine Use and Manufacturing

Methods of Manufacturing

General procedure: TAPEHA-Pd (0.015 g) was added to a solution of nitroarenes (1.0 mmol) in EtOH/water (1/1) (20 mL). After NaBH4 (4.0 mmol) was slowly added to the mixture, the color of the reaction mixture turned gradually black in a few minutes, resulting in the formation of palladium nanoparticles (TAPEHA-PdNPs). 42 After being stirredfor 1.5 h at room temperature and atmospheric pressure, the catalyst was removed by ltering and the fitrate was extracted with 3 30 mL of EtOAc. The combined organic layers were dried over MgSO4 and concentrated in a vacuum.General procedure: SAC (300mg) and NaBHIn a 600 mL autoclave equipped with a gas entrapment stirrer 240 g aqueous ammonia (28percent NHIn a 600 mL autoclave equipped with a gas entrapment stirrer, a solution of 5 g CuI in 120 g aqueous ammonia (30percent NH3 by weight) was added and mixed with 77 g ammonium acetate and 60 g of 2, 6-dichloropyridine. After purging with nitrogen, 24 g of liquid ammonia were added resulting in a pressure of about 150 psi (1.03 MPa). Subsequently, the reaction mixture was heated to 150°C for 8 h under stirring. Over the course of the reaction, the pressure decreased from an initial pressure of 680 psi (4.69 MPa) to 450 psi (3.10 MPa). The reaction mixture was allowed to cool to room temperature, and the pressure was brought back to atmospheric pressure. The reaction mixture was analyzed using a quantitative GC analytical method. The conversion of 2, 6-dichloropyridine was greater than 99.5percent. The reaction mixture contained 0.37 mol 2, 6- diaminopyridine and 0.03 mol 2-chloro-6-amino pyridine. The yields for 2, 6-diaminopyridine and 2-chloro-6-amino pyridine were 91percent and 7percent, respectively.This reaction was conducted in the same manner as described in Example 1, but no ammonium acetate was added to the reaction mixture, demonstrating that lower selectivity is obtained in an unbuffered solution. The conversion of 2, 6-dichloropyridine was greater than 99.5percent. The reaction mixture contained 0.29 mol 2, 6-diaminopyridine and less than 0.005 mol 2-chloro-6-amino pyridine. The yield for 2, 6-diaminopyridine was 72percent.

Uses

Substrate used in a Ni(II)-catalyzed homo-coupling providing diamino-2,2′-bipyridine.1

Computed Properties

Molecular Weight:128.56
XLogP3:0.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:128.0141259
Monoisotopic Mass:128.0141259
Topological Polar Surface Area:38.9
Heavy Atom Count:8
Complexity:76.8
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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