3-Chloropyridine

3-Chloropyridine
Names
	Preferred IUPAC name 3-Chloropyridine
Identifiers
CAS Number	626-60-8;
3D model (JSmol)	Interactive image;
ChemSpider	11784;
ECHA InfoCard	100.009.960
EC Number	210-955-7;
PubChem CID	12287;
UNII	1M13HUC1P4;
CompTox Dashboard (EPA)	DTXSID3052309 ;
	InChI InChI=1S/C5H4ClN/c6-5-2-1-3-7-4-5/h1-4H Key: PWRBCZZQRRPXAB-UHFFFAOYSA-N;
	SMILES C1=CC(=CN=C1)Cl;
Properties
Chemical formula	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:
Pictograms
Signal word	Warning
Hazard statements	H226, H302, H312, H315, H332
Precautionary statements	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). Infobox references

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]

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

References

^ 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.
^ 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.
^ 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.
^ 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.

[shimizu-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.

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