3-Chloropyridine
Chemical compound
From Wikipedia, the free encyclopedia
3-Chloropyridine is an aryl chloride and isomer of chloropyridine with the formula C5H4ClN. It is a colorless liquid that is mainly used as a building block in organic synthesis.[1]
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| Names | |||
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| Preferred IUPAC name
3-Chloropyridine | |||
| Identifiers | |||
3D model (JSmol) |
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| ChemSpider | |||
| ECHA InfoCard | 100.009.960 | ||
| EC Number |
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PubChem CID |
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CompTox Dashboard (EPA) |
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| Properties | |||
| C5H4ClN | |||
| Molar mass | 113.54 g·mol−1 | ||
| Appearance | colorless liquid | ||
| Density | 1.194 g/cm3 | ||
| Boiling point | 148 °C (298 °F; 421 K) | ||
Refractive index (nD) |
1.533 | ||
| Hazards | |||
| GHS labelling: | |||
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| Warning | |||
| H226, H302, H312, H315, H332 | |||
| P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+P312, P302+P352, P303+P361+P353, P304+P312, P304+P340, P312, P321, P322, P330, P332+P313, P362, P363, P370+P378, P403+P235, P501 | |||
| Flash point | 65 °C (149 °F; 338 K) | ||
| Related compounds | |||
Related compounds |
2-Chloropyridine 3-Bromopyridine | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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The compound is a substrate for many coupling processes including the Heck reaction,[2] Suzuki reaction,[3] and Ullmann reaction.[4]
Preparation
3-Chloropyridine may be prepared by the direct chlorination of pyridine with aluminium chloride used as the catalyst. The yield is 33%.[5]
A less expensive way of preparing 3-chloropyridine consists of the gas phase pyrolysis of a mixture of pyrrole and chloroform in an empty glass tube. The molar ratio of the reagents is one to five. The yields range from 25 to 33%. A little 2-chloropyridine is formed as a side product.[6] The process is thought to be an example of the Ciamician–Dennstedt rearrangement.
Pyrolytic Ciamician-Dennstedt rearrangement leading to 3-chloropyridine
