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2-Bromopyridine

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2-Bromopyridine Basic information

Product Name:
2-Bromopyridine
Synonyms:
  • Pyridine,2-bromo-
  • 2-BROMOPYRIDINE FOR SYNTHESIS
  • 2-Bromopyridine≥ 99% (GC)
  • 2-BROMOPYRIDINE, 98%2-BROMOPYRIDINE, 98%2-BROMOPYRIDINE, 98%2-BROMOPYRIDINE, 98%
  • TIMTEC-BB SBB003999
  • AKOS BBS-00004324
  • ALPHA-BROMOPYRIDINE
  • BROMOPYRIDINE(2-)
CAS:
109-04-6
MF:
C5H4BrN
MW:
158
EINECS:
203-641-6
Product Categories:
  • alkyl bromide
  • C5Heterocyclic Building Blocks
  • Bromopyridines
  • Halopyridines
  • Halogenated Heterocycles
  • Heterocyclic Building Blocks
  • Pyridine
  • Pyridines, Pyrimidines, Purines and Pteredines
  • Halides
  • Pyridines
  • Pyridines derivates
  • bc0001
  • 109-04-6
Mol File:
109-04-6.mol
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2-Bromopyridine Chemical Properties

Melting point:
193°C
Boiling point:
192-194 °C (lit.)
Density 
1.657 g/mL at 25 °C (lit.)
refractive index 
n20/D 1.572(lit.)
Flash point:
130 °F
storage temp. 
Keep in dark place,Sealed in dry,Room Temperature
solubility 
20g/l
form 
Liquid
pka
pK1: 0.71(+1) (25°C)
color 
Clear colorless to pale brown
Water Solubility 
Slightly miscible with water.
BRN 
105789
Dielectric constant
24.02
Stability:
Stable. Flammable. Incompatible with strong oxidizing agents, strong acids, acid chlorides.
InChIKey
IMRWILPUOVGIMU-UHFFFAOYSA-N
LogP
1.42
CAS DataBase Reference
109-04-6(CAS DataBase Reference)
NIST Chemistry Reference
Pyridine, 2-bromo-(109-04-6)
EPA Substance Registry System
Pyridine, 2-bromo- (109-04-6)
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Safety Information

Hazard Codes 
T,Xn,F
Risk Statements 
10-24/25-36/37/38-23/24/25-20/21/22
Safety Statements 
16-36/37-45-38-36/37/39-28A-26
RIDADR 
UN 2929 6.1/PG 2
WGK Germany 
3
RTECS 
US3850000
8
Hazard Note 
Toxic
TSCA 
Yes
HazardClass 
6.1
PackingGroup 
II
HS Code 
29333999

MSDS

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2-Bromopyridine Usage And Synthesis

Chemical Properties

light yellow oily or dark red liquid. miscible with ethanol, ether, benzene and pyridine, still soluble in water.

Uses

2-Bromopyridine is a 2-halogenated pyridine used in the preparation of a variety of biologically active compounds such as antimalarial agents and beta-adrenoceptor agonist.

Application

2-Bromopyridine can be used as:
A building block in the formation of C?N bond by various cross coupling reactions.
A reactant in Negishi cross-coupling reaction with aryl halides catalyzed by palladium.
A reactant in the synthesis of 2′-pyridyldifluoroacetate with ethyl bromodifluoroacetate in presence of copper as a catalyst.

Preparation

2-Bromopyridine is synthesized from 2-aminopyridine by bromination. In industrial production, hydrobromic acid (over 48%) is first cooled to below 0°C, 2-aminopyridine is slowly added, and then liquid bromine is added dropwise in a salt bath under freezing, and the rate of addition is to control the reaction temperature below -5°C appropriate. After adding, add sodium nitrite aqueous solution dropwise, control the reaction temperature to be below 0°C, stir for 20-30min, dropwise add 50% sodium hydroxide solution, extract the reaction solution with ether, wash with water, dry with anhydrous sodium sulfate, filter, and recover Diethyl ether, the residue was distilled under reduced pressure, and the 88°C-94°C/3333Pa fraction was collected to obtain the finished product of 2-bromopyridine with a yield of 83.8%.

Definition

ChEBI: 2-bromopyridine is a monobromopyridine.

Reactions

2-Bromopyridine reacts with butyllithium to give 2-lithiopyridine, which is a versatile reagent.Pyrithione can be prepared in a two-step synthesis from 2-bromopyridine by oxidation to the N-oxide with a suitable peracid followed by substitution using either sodium dithionite or sodium sulfide with sodium hydroxide to introduce the thiol functional group.

Flammability and Explosibility

Flammable

Purification Methods

Dry 2-bromopyridine over KOH for several days, then distil it from CaO under reduced pressure, and taking the middle fraction. [Beilstein 20/5 V 422.]

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