| Identification | More | [Name]
2-Bromopyridine | [CAS]
109-04-6 | [Synonyms]
AKOS BBS-00004324
ALPHA-BROMOPYRIDINE
BROMOPYRIDINE(2-)
TIMTEC-BB SBB003999
2-bromo-pyridin
2-pyridylbromide
beta-bromopyridine
-Bromoazine
-Bromopyridine
o-Bromopyridine
Pyridine,2-bromo-
2-BROMO PYRIDINE 2-BROMO PYRIDINE
2-Bromopyridine ,99% | [EINECS(EC#)]
203-641-6 | [Molecular Formula]
C5H4BrN | [MDL Number]
MFCD00006219 | [Molecular Weight]
158 | [MOL File]
109-04-6.mol |
| Chemical Properties | Back Directory | [Appearance]
dark red liquid | [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.)
| [Fp ]
130 °F
| [storage temp. ]
Refrigerator | [solubility ]
20g/l | [form ]
Liquid | [pka]
pK1: 0.71(+1) (25°C) | [color ]
Clear colorless to pale brown | [Stability:]
Stable. Flammable. Incompatible with strong oxidizing agents, strong acids, acid chlorides. | [Water Solubility ]
Slightly miscible with water. | [Detection Methods]
GC,HPLC,NMR | [BRN ]
105789 | [Dielectric constant]
24.02 | [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]
109-04-6(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
T,Xn,F | [Risk Statements ]
R10:Flammable.
R24/25:Toxic in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin .
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S16:Keep away from sources of ignition-No smoking .
S36/37:Wear suitable protective clothing and gloves .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S38:In case of insufficient ventilation, wear suitable respiratory equipment .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [RIDADR ]
UN 2929 6.1/PG 2
| [WGK Germany ]
3
| [RTECS ]
US3850000
| [F ]
8 | [Hazard Note ]
Toxic | [TSCA ]
Yes | [HazardClass ]
6.1 | [PackingGroup ]
II | [HS Code ]
29333999 |
| Hazard Information | Back Directory | [Chemical Properties]
dark red liquid | [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. | [Definition]
ChEBI: 2-bromopyridine is a monobromopyridine. | [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%. | [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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