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2-Bromo-5-fluoropyridine

2-Bromo-5-fluoropyridine structure

CAS No:
41404-58-4
Formula:
C5H3BrFN
Chemical Name:
2-Bromo-5-fluoropyridine
Synonyms:
2-BROMO-5-FLUOROPYRIDINE;2--5- fluoropyridinebroMide;2-BroMo-5-fluoropyridine, 97+%;2 - broMine - 5 - fluoride pyridine;5-FLUOROPYRIDIN-2-YL-BORONIC ACID;5-FLUOROPYRIDINE-2-BORONIC ACID;2-bromo-5-fluoropyridin;2-Bromo-5-fluoropyridine98%
Categories:
Pharmaceutical Intermediates > Heterocyclic Compound

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Description

Light yellow Cryst

2-Bromo-5-fluoropyridine Basic Attributes

Molecular Weight：

175.99

Exact Mass：

174.943283

BRN：

1561456

EC Number：

1533716-785-6

DSSTox ID：

DTXSID70382481

HScode：

2933399090

Characteristics

PSA：

12.9

XLogP3：

Appearance：

Colorless to slightly yellow Liquid

Density：

1.7±0.1 g/cm3

Melting Point：

30-31 °C(lit.)

Boiling Point：

80-83 °C44 mm Hg(lit.)

Flash Point：

167 °F

Refractive Index：

1.5396

Storage Conditions：

StoreCold

Safety Information

Packing level：

III

Hazard category：

6.1

Transport codes：

2811

wgk germany：

hazard class code：

36/37/38-20/21/22-10

safety instructions：

26-36-16

Marks：

Xi,Xn,F

Hazard note：

Irritant

Precautionary statement(s)：

P261-P305 + P351 + P338

Hazard Statements：

H302-H315-H319-H335

GHS Classification：

|Warning|H302 (87.23%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 47 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

2-Bromo-5-fluoropyridine Use and Manufacturing

Methods of Manufacturing

2-Bromo-5-fluoro-pyridine; 2-Amino-5-fluoropyridine (6.5 g, 58 mmol) was added in portions to cool (0-5° C.) hydrobromic acid 48percent (28.8 ml, 296 mmol). Bromine (8.9 ml, 174 mmol) and a solution of sodium NaNOTo a 3-neck flask equipped with a dropping ihtmel and thermometer, 48percent BBr (26'.?' mL) was added, S-Fiooropyridia-Z-aittine (6, 0 g, 0.05 mol) was added, dropwise at 0 °C. Br2 (8*0 mL, 0.16 mol) was then added at 0 'C dropwise over 20 mm. The reaction mixture was cooled to -1.0 °C and a solution ofNa O^ (9.3 g, 0.14 mol) in water (30 ml) was added over 1.5 hours, 'the resulting mixture was stirred for an. additional 30 minutes. A solutio of NaO (20 g, 0.50 mol) in water (30 mL) was added over 30 mirtutes. The reaction mixture was warmed to 5 °C and then extmcted with ether (3* 100 .mL). The combined organic phases were washed with brine, dried over sodium sulfate, filtered, and concentrated. The concentrate was purified by column chromatography over silica gel (hexane/EiOAc::::lG0. i) to afford the title compound as a colorless liquid (3.37 g, 36percent).. 1H ‘NMR (400 MHz, CDC[4) d 8.27 Cd, J 3.0 Hz, ff1). 7.48 (dd, J =8.7, 4.0 Hz, IFi), 735 - 7, 2S (m. I H).

Uses

3-Fluoro-6-bromopyridine is used in the synthesis of mGluR5 antagonist for the treatment of neuropathic pain.

Computed Properties

Molecular Weight:175.99
XLogP3:2
Hydrogen Bond Acceptor Count:2
Exact Mass:174.94329
Monoisotopic Mass:174.94329
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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