3-Bromopyridine

3-Bromopyridine
Names
	Preferred IUPAC name 3-Bromopyridine
Identifiers
CAS Number	626-55-1;
3D model (JSmol)	Interactive image;
Beilstein Reference	105880
ChEBI	CHEBI:51575;
ChemSpider	11783;
ECHA InfoCard	100.009.957
EC Number	210-952-0;
PubChem CID	12286;
UNII	XMN8H2XE9H;
CompTox Dashboard (EPA)	DTXSID9060819 ;
	InChI InChI=1S/C5H4BrN/c6-5-2-1-3-7-4-5/h1-4H Key: NYPYPOZNGOXYSU-UHFFFAOYSA-N;
	SMILES C1=CC(=CN=C1)Br;
Properties
Chemical formula	C5H4BrN
Molar mass	157.998 g·mol−1
Appearance	colorless liquid
Density	1.640 g/cm3
Melting point	−27
Boiling point	173 °C (343 °F; 446 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H226, H301, H302, H311, H315, H319, H332, H335
Precautionary statements	P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+P310, P301+P312, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P361, P362, P363, P370+P378, P403+P233, P403+P235, P405, P501
Flash point	51 °C (124 °F; 324 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

3-Bromopyridine is an organohalide with the formula C₅H₄BrN. It is a colorless liquid that is mainly used as a building block in organic synthesis.[1][2]

It participates as a substrate in many reactions associated with aryl halides, e.g., the Heck reaction[3] and Buchwald-Hartwig coupling.[4]

Related compounds

References

Li, Wenjie; Nelson, Dorian P.; Jensen, Mark S.; Hoerrner, R. Scott; Cai, Dongwei; Larsen, Robert D. (2005). "Synthesis of 3-Pyridylboronic Acid and ITS Pinacol Ester. Application of 3-Pyridylboronic Acid in Suzuki Coupling to Prepare 3-Pyridin-3-Ylquinoline". Organic Syntheses. 81: 89. doi:10.15227/orgsyn.081.0089.
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.
Heck, Richard F. (1979). "Palladium-catalyzed reactions of organic halides with olefins". Accounts of Chemical Research. 12 (4): 146–151. doi:10.1021/ar50136a006.
Zhang, Hui; Cai, Qian; Ma, Dawei (2005). "Amino Acid Promoted CuI-Catalyzed C−N Bond Formation between Aryl Halides and Amines or N-Containing Heterocycles". The Journal of Organic Chemistry. 70 (13): 5164–5173. doi:10.1021/jo0504464. PMID 15960520.

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[1] Li, Wenjie; Nelson, Dorian P.; Jensen, Mark S.; Hoerrner, R. Scott; Cai, Dongwei; Larsen, Robert D. (2005). "Synthesis of 3-Pyridylboronic Acid and ITS Pinacol Ester. Application of 3-Pyridylboronic Acid in Suzuki Coupling to Prepare 3-Pyridin-3-Ylquinoline". Organic Syntheses. 81: 89. doi:10.15227/orgsyn.081.0089.

[shimizu-2] 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.

[3] Heck, Richard F. (1979). "Palladium-catalyzed reactions of organic halides with olefins". Accounts of Chemical Research. 12 (4): 146–151. doi:10.1021/ar50136a006.

[4] Zhang, Hui; Cai, Qian; Ma, Dawei (2005). "Amino Acid Promoted CuI-Catalyzed C−N Bond Formation between Aryl Halides and Amines or N-Containing Heterocycles". The Journal of Organic Chemistry. 70 (13): 5164–5173. doi:10.1021/jo0504464. PMID 15960520.