3-Bromopyridine

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 pictograms
GHS Signal word	Danger
GHS hazard statements	H226, H301, H302, H311, H315, H319, H332, H335
GHS precautionary statements	P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+310, P301+312, P302+352, P303+361+353, P304+312, P304+340, P305+351+338, P312, P321, P322, P330, P332+313, P337+313, P361
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.