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5-Bromo-2-chloropyridine

5-Bromo-2-chloropyridine structure

CAS No:
53939-30-3
Formula:
C5H3BrClN
Chemical Name:
5-Bromo-2-chloropyridine
Categories:
Pharmaceutical Intermediates > Bulk Drug Intermediates

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Description

Light yellow Cryst

5-Bromo-2-chloropyridine Basic Attributes

Molecular Weight：

192.44

Exact Mass：

190.913727

DSSTox ID：

DTXSID80370293

HScode：

2933399090

Characteristics

PSA：

12.9

XLogP3：

2.5

Appearance：

White crystal powder

Density：

1.7±0.1 g/cm3

Melting Point：

65-69 °C(lit.)

Boiling Point：

208.1°C at 760 mmHg

Flash Point：

79.7±21.8 °C

Refractive Index：

1.581

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

R36/37/38

safety instructions：

S26-S36-S37/39

Marks：

Xi:Irritant

Precautionary statement(s)：

P261-P305 + P351 + P338

Hazard Statements：

H315-H319-H335

GHS Classification：

|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 46 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

5-Bromo-2-chloropyridine Use and Manufacturing

b) Preparation of 5 -bromo-2-chloro-pyridine. 6-Chloro-pyridin-3-ylamine (15 g, 117 mmol) was dissolved slowly with constant stirring in 48percent HBr solution (50 mL) at r.t. and then the solution was chilled to -10 °C. A solution of sodium nitrite (8.9 g, 129 mmol) in cold water (25 mL) was added dropwise at -10 °C with constant stirring over 2 h, followed by a solution of copper (I) bromide (25 g, 176 mmol) in 48percent HBr (40 mL) dropwise. The mixture was- then stirred at r.t. until complete. The mixture was neutralised with sodium carbonate and extracted with ethyl acetate. The organic phase was washed with brine, dried over soldium sulfate and concentrated. The residue was purified by column chromatography on silica gel (60-120 mesh) eluting with 1percent ethyl acetate/petroleum ether to afford 5- bromo-2-chloro-pyridine (ll.l g, 49percent).[5-BROMO-2-CHLOROPYRIDINE] To a solution of the available 5-amino-2-chloropyridine (3.0 g, 23.3 [MMOL)] in HBr solution 48percent [AT-10XB0;C] was added a sodium nitrite solution (4.18 g, 60.7 [MMOL)] in [WATER (6 ML). BROMINE (11.2 G, 3 EQ. ) WAS SLOWLY ADDED AND THE REACTION WAS STIRRED] at rt for 48 hours. After addition of a [NAOH] solution (16.8 [G)] in water (42 mL), and extraction with [ET20, ] the organic layer was dried over [NA2SO4] and evaporated. After purification by flash chromatography using DCM/Cyclohexane 50/50 as eluent, the title compound was obtained as a white solid (0.135 g, 0.7 [MMOL)] in 3percent yield ; GC/MS: [M+C5H3BRCIN] 192a A.

Computed Properties

Molecular Weight:192.44
XLogP3:2.5
Hydrogen Bond Acceptor Count:1
Exact Mass:190.91374
Monoisotopic Mass:190.91374
Topological Polar Surface Area:12.9
Heavy Atom Count:8
Complexity:78.8
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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