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626-60-8

Basic Information
CAS No.: 626-60-8
Name: 3-Chloropyridine
Article Data: 63
Molecular Structure:
Molecular Structure of 626-60-8 (3-Chloropyridine)
Formula: C5H4ClN
Molecular Weight: 113.546
Synonyms: m-Chloropyridine;Pyridine, 3-chloro-;5-20-05-00406 (Beilstein Handbook Reference);3-Pyridinyl chloride;
EINECS: 210-955-7
Density: 1.2 g/cm3
Melting Point: -0.5oC
Boiling Point: 143.1 °C at 760 mmHg
Flash Point: 49.7 °C
Solubility: Soluble in water 10 g/L.
Appearance: clear colorless to yellow liquid
Hazard Symbols: HarmfulXn,IrritantXi
Risk Codes: 20/21/22-36/37/38
Safety: 36/37/39-26
Transport Information: UN 2822
PSA: 12.89000
LogP: 1.73500
Synthetic route
462-08-8

pyridin-3-ylamine

626-60-8

3-Chloropyridine

Conditions
ConditionsYield
With tert-Butyl thionitrate; copper dichloride In acetonitrile at 25℃; for 6h;95%
With hydrogenchloride; copper; sodium nitrite Diazotization;
1851-22-5

3-chloropyridine-N-oxide

626-60-8

3-Chloropyridine

Conditions
ConditionsYield
With hydrogen; triethyl phosphite In isopropyl alcohol at 100℃; under 4500.45 Torr; for 12h; Glovebox; chemoselective reaction;93%
With aluminium(III) iodide In acetonitrile for 6h; Heating;80%
With 1,1,2,2-tetrabutyl-1,2-dichloro distannane In tetrahydrofuran for 1h; Heating;75%
626-55-1

3-Bromopyridine

626-60-8

3-Chloropyridine

Conditions
ConditionsYield
With trans-bis(glycinato)copper(II) monohydrate; tetramethlyammonium chloride In ethanol at 100℃; for 20h; Finkelstein Reaction; Schlenk technique; Inert atmosphere;90%
With copper(I) oxide; tetramethlyammonium chloride; L-proline In ethanol at 110℃; for 36h; Inert atmosphere;89 %Chromat.
With iron(III) chloride; sodium chloride In acetonitrile for 4h; Kinetics; Irradiation; Green chemistry;
29955-47-3

3,5-Dinitro-N-phenyl-benzimidoyl chloride

A

626-60-8

3-Chloropyridine

B

7461-51-0

3,5-dinitro-(N-phenyl)benzamide

C

16527-88-1

Pyridine 1-oxide hydrochloride

Conditions
ConditionsYield
With pyridine N-oxide In 1,2-dichloro-ethane for 24h; Heating;A 3.7%
B 89.8%
C n/a
87282-02-8

2,4-Dinitro-N-phenyl-benzimidoyl chloride

A

626-60-8

3-Chloropyridine

B

22978-56-9

2,4-dinitro-benzoic acid anilide

C

16527-88-1

Pyridine 1-oxide hydrochloride

Conditions
ConditionsYield
With pyridine N-oxide In 1,2-dichloro-ethane for 24h; Heating;A 19.4%
B 85.3%
C n/a
30435-62-2

C19H14N2O2

A

626-60-8

3-Chloropyridine

B

119-61-9

benzophenone

C

67-72-1

hexachloroethane

D

983-79-9

benzophenone azine

Conditions
ConditionsYield
With tetrachloromethane Ambient temperature; Irradiation; Yields of byproduct given;A 82%
B n/a
C n/a
D n/a
694-59-7

pyridine N-oxide

57761-80-5

N-Phenyl-o-nitrobenzimidoyl chloride

A

626-60-8

3-Chloropyridine

B

2385-27-5

N-phenyl-2-nitrobenzamide

C

16527-88-1

Pyridine 1-oxide hydrochloride

D

87281-92-3

2-Nitro-N-phenyl-N-pyridin-2-yl-benzamide

Conditions
ConditionsYield
In 1,2-dichloro-ethane for 24h; Heating;A 29.8%
B 66%
C n/a
D 30.7%
57761-80-5

N-Phenyl-o-nitrobenzimidoyl chloride

A

626-60-8

3-Chloropyridine

B

2385-27-5

N-phenyl-2-nitrobenzamide

C

16527-88-1

Pyridine 1-oxide hydrochloride

D

87281-92-3

2-Nitro-N-phenyl-N-pyridin-2-yl-benzamide

Conditions
ConditionsYield
With pyridine N-oxide In 1,2-dichloro-ethane for 24h; Heating;A 29.8%
B 66%
C n/a
D 30.7%
694-59-7

pyridine N-oxide

5509-90-0

3-nitro-N-phenyl-benzimidoyl chloride

A

626-60-8

3-Chloropyridine

B

2243-73-4

5-nitrobenzanilide

C

16527-88-1

Pyridine 1-oxide hydrochloride

D

87281-93-4

2-pyridine

Conditions
ConditionsYield
In 1,2-dichloro-ethane for 24h; Heating;A 41.3%
B 62.7%
C n/a
D 30.1%
694-59-7

pyridine N-oxide

A

626-60-8

3-Chloropyridine

B

2243-73-4

5-nitrobenzanilide

C

16527-88-1

Pyridine 1-oxide hydrochloride

D

87281-93-4

2-pyridine

Conditions
ConditionsYield
With N-Phenyl-m-nitrobenzimidoyl chloride In 1,2-dichloro-ethane for 24h; Heating;A 41.3%
B 62.7%
C n/a
D 30.1%
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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

This product is an organic compound with the formula C5H4ClN. The systematic name of this chemical is 3-Chloropyridine. It belongs to the product categories of Blocks; Pyridines; Pyridine; Chlorine Compounds; Miscellaneous Compounds; Chloropyridines; Halopyridines; C5 Heterocyclic Building Blocks; Halogenated Heterocycles; Heterocyclic Building Blocks; Pyridine series. Its EINECS number is 210-955-7. With the CAS registry number 626-60-8, it is also named as 3-Pyridinyl chloride. Its classification code is Mutation data. In addition, the molecular weight is 113.54. It is used as a pharmaceutical intermediate. It should be sealed and stored in a cool and dry place. Moreover, it should be protected from oxides.

Physical properties of 3-Chloropyridine are: (1)ACD/LogP: 1.57; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.57; (4)ACD/LogD (pH 7.4): 1.57; (5)ACD/BCF (pH 5.5): 9.15; (6)ACD/BCF (pH 7.4): 9.18; (7)ACD/KOC (pH 5.5): 169.65; (8)ACD/KOC (pH 7.4): 170.12; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 12.89 Å2; (13)Index of Refraction: 1.53; (14)Molar Refractivity: 29.23 cm3; (15)Molar Volume: 94.6 cm3; (16)Polarizability: 11.59×10-24cm3; (17)Surface Tension: 39.5 dyne/cm; (18)Density: 1.2 g/cm3; (19)Flash Point: 49.7 °C; (20)Enthalpy of Vaporization: 36.46 kJ/mol; (21)Boiling Point: 143.1 °C at 760 mmHg; (22)Vapour Pressure: 6.8 mmHg at 25°C.

Preparation: this chemical can be prepared by pyridin-3-ylamine at the temperature of 25 °C. This reaction will need reagents t-butyl thionitrate, CuCl2 and solvent acetonitrile with the reaction time of 6 hours. The yield is about 95%.

3-Chloropyridine can be prepared by pyridin-3-ylamine at the temperature of 25 °C

Uses of 3-Chloropyridine: it can be used to produce 3-chloro-pyridine-1-oxide at the ambient temperature. It will need reagents MeReO3, H2O2 and solvents H2O, CH2Cl2 with the reaction time of 17 hours. The yield is about 84%.

3-Chloropyridine can be used to produce 3-chloro-pyridine-1-oxide at the ambient temperature

When you are using this chemical, please be cautious about it as the following:
This chemical is harmful by inhalation, in contact with skin and if swallowed. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need wear suitable protective clothing, gloves and eye/face protection.

You can still convert the following datas into molecular structure:
(1)SMILES: Clc1cccnc1
(2)Std. InChI: InChI=1S/C5H4ClN/c6-5-2-1-3-7-4-5/h1-4H
(3)Std. InChIKey: PWRBCZZQRRPXAB-UHFFFAOYSA-N

The toxicity data is as follows:  

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
bird - wild LD50 oral 750mg/kg (750mg/kg)   Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983.
mouse LD50 intraperitoneal 235mg/kg (235mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ANTIPSYCHOTIC

LIVER: FATTY LIVER DEGERATION
Toxicology and Applied Pharmacology. Vol. 11, Pg. 361, 1967.