3-Bromopyridine

{{Chembox

| ImageFile1 = 3-bromopyridine.svg

| ImageSize1 = 122

| ImageAlt1 =

| ImageFileL2 = 3-bromopyridine-from-xtal-3D-bs-17.png

| ImageFileR2 = 3-bromopyridine-from-xtal-3D-sf.png

| PIN = 3-Bromopyridine

| OtherNames =

|Section1={{Chembox Identifiers

| CASNo = 626-55-1

| PubChem = 12286

| EC_number = 210-952-0

| UNII = XMN8H2XE9H

| ChemSpiderID = 11783

| ChEBI = 51575

| Beilstein = 105880

| StdInChI=1S/C5H4BrN/c6-5-2-1-3-7-4-5/h1-4H

| StdInChIKey = NYPYPOZNGOXYSU-UHFFFAOYSA-N

| SMILES = C1=CC(=CN=C1)Br

}}

|Section2={{Chembox Properties

| C=5|H=4|Br=1|N=1

| MolarMass =

| Appearance = colorless liquid

| Density = 1.640 g/cm³

| MeltingPtC = −27

| BoilingPtC = 173

| Solubility = }}

|Section3={{Chembox Hazards

| GHSPictograms = {{GHS02}}{{GHS06}}{{GHS07}}

| GHSSignalWord = Danger

| HPhrases = {{H-phrases|226|301|302|311|315|319|332|335}}

| PPhrases = {{P-phrases|210|233|240|241|242|243|261|264|270|271|280|301+310|301+312|302+352|303+361+353|304+312|304+340|305+351+338|312|321|322|330|332+313|337+313|361|362|363|370+378|403+233|403+235|405|501}}

| MainHazards =

| FlashPtC = 51

| AutoignitionPt = }}

| Section4 = {{Chembox Related

| OtherCompounds = 3-Chloropyridine
2-Bromopyridine

}}

}}

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.{{cite journal |doi=10.15227/orgsyn.081.0089|title=Synthesis of 3-Pyridylboronic Acid and ITS Pinacol Ester. Application of 3-Pyridylboronic Acid in Suzuki Coupling to Prepare 3-Pyridin-3-Ylquinoline|journal=Organic Syntheses|year=2005|volume=81|page=89|first1=Wenjie|last1=Li|first2=Dorian P.|last2=Nelson|first3=Mark S.|last3=Jensen|first4=R. Scott|last4=Hoerrner|first5=Dongwei|last5=Cai|first6=Robert D.|last6= Larsen|doi-access=free}}{{Ullmann|first1=Shinkichi|last1=Shimizu|first2=Nanao|last2=Watanabe|first3=Toshiaki|last3=Kataoka|first4=Takayuki|last4= Shoji|first5=Nobuyuki|last5=Abe|first6=Sinji|last6=Morishita|first7=Hisao|last7=Ichimura|title=Pyridine and Pyridine Derivatives|year=2007|doi=10.1002/14356007.a22_399}}

It participates as a substrate in many reactions associated with aryl halides, e.g., the Heck reaction{{cite journal |doi=10.1021/ar50136a006|title=Palladium-catalyzed reactions of organic halides with olefins|year=1979|last1=Heck|first1=Richard F.|journal=Accounts of Chemical Research|volume=12|issue=4|pages=146–151}} and Buchwald–Hartwig amination.{{cite journal |doi=10.1021/jo0504464|title=Amino Acid Promoted CuI-Catalyzed C−N Bond Formation between Aryl Halides and Amines or N-Containing Heterocycles|year=2005|last1=Zhang|first1=Hui|last2=Cai|first2=Qian|last3=Ma|first3=Dawei|journal=The Journal of Organic Chemistry|volume=70|issue=13|pages=5164–5173|pmid=15960520}}