3-Bromopyridine
Names
Preferred IUPAC name
3-Bromopyridine
Identifiers
3D model (JSmol)
105880
ChEBI
ChemSpider
ECHA InfoCard 100.009.957 Edit this at Wikidata
EC Number
  • 210-952-0
UNII
  • InChI=1S/C5H4BrN/c6-5-2-1-3-7-4-5/h1-4H
    Key: NYPYPOZNGOXYSU-UHFFFAOYSA-N
  • C1=CC(=CN=C1)Br
Properties
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:
GHS02: FlammableGHS06: ToxicGHS07: Exclamation mark
Danger
H226, H301, H302, H311, H315, H319, H332, H335
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)
Related compounds
Related compounds
 3-Chloropyridine
2-Bromopyridine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

3-Bromopyridine is an aryl bromide and isomer of bromopyridine 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]

References

  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.
  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. ISBN 978-3527306732.
  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.
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