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HomeProduct name list2-Bromopyridine

2-Bromopyridine

  • CAS NO.:109-04-6
  • Empirical Formula: C5H4BrN
  • Molecular Weight: 158
  • MDL number: MFCD00006219
  • EINECS: 203-641-6
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-12-18 14:08:52
2-Bromopyridine Structural

What is 2-Bromopyridine?

Chemical properties

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

The Uses of 2-Bromopyridine

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.

What are the applications of 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.

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.

Preparation

2-Bromopyridine can be prepared from 2-aminopyridine via diazotization followed by bromination.

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.]

Properties of 2-Bromopyridine

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.
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)

Safety information for 2-Bromopyridine

Signal word Danger
Pictogram(s)
ghs
Skull and Crossbones
Acute Toxicity
GHS06
GHS Hazard Statements H301:Acute toxicity,oral
H310:Acute toxicity,dermal
H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P262:Do not get in eyes, on skin, or on clothing.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for 2-Bromopyridine

InChIKey IMRWILPUOVGIMU-UHFFFAOYSA-N

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