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]

3-Chloropyridine
Names
Preferred IUPAC name
3-Chloropyridine
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.009.960 Edit this at Wikidata
EC Number
  • 210-955-7
UNII
  • InChI=1S/C5H4ClN/c6-5-2-1-3-7-4-5/h1-4H
    Key: PWRBCZZQRRPXAB-UHFFFAOYSA-N
  • C1=CC(=CN=C1)Cl
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)
1.533
Hazards
GHS labelling:
GHS02: FlammableGHS07: Exclamation mark
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).

The compound is a substrate for many coupling processes including the Heck reaction,[2] Suzuki reaction,[3] and Ullmann reaction.[4]

References

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  1. ^ Shimizu, Shinkichi; Watanabe, Nanao; Kataoka, Toshiaki; Shoji, Takayuki; Abe, Nobuyuki; Morishita, Sinji; Ichimura, Hisao (2007). "Pyridine and Pyridine Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a22_399. ISBN 978-3527306732.
  2. ^ Littke, Adam F.; Fu, Gregory C. (2001). "A Versatile Catalyst for Heck Reactions of Aryl Chlorides and Aryl Bromides under Mild Conditions". Journal of the American Chemical Society. 123 (29): 6989–7000. doi:10.1021/ja010988c. PMID 11459477.
  3. ^ Littke, Adam F.; Dai, Chaoyang; Fu, Gregory C. (2000). "Versatile Catalysts for the Suzuki Cross-Coupling of Arylboronic Acids with Aryl and Vinyl Halides and Triflates under Mild Conditions". Journal of the American Chemical Society. 122 (17): 4020–4028. doi:10.1021/ja0002058.
  4. ^ Alonso, Diego A.; Nájera, Carmen; Pacheco, M Carmen (2002). "Highly Active Oxime-Derived Palladacycle Complexes for Suzuki−Miyaura and Ullmann-Type Coupling Reactions". The Journal of Organic Chemistry. 67 (16): 5588–5594. doi:10.1021/jo025619t. PMID 12153256.