2-Bromo-5-fluoropyridine

Iupac Name：2-bromo-5-fluoropyridine

Molecular Weight：175.988

Modify Date.: 2022-11-22 16:51

Introduction: 2-Bromo-5-fluoropyridine is used in the synthesis of mGluR5 antagonist for the treatment of neuropathic pain. 2-Bromo-5-fluoropyridineSupplier View more+

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1. Names and Identifiers

1.1 Name: 2-Bromo-5-fluoropyridine
1.2 Synonyms: 2 - broMine - 5 - fluoride pyridine 2--5- fluoropyridinebroMide 2-bromo-5-fluoro pyridine 2-bromo-5-fluoropyridin 2-Bromo-5-fluoro-pyridine 3-fluoro-6-bromopyridine 5-fluoro-2-bromopyridine 5-FLUOROPYRIDIN-2-YL-BORONIC ACID 5-FLUOROPYRIDINE-2-BORONIC ACID MFCD00234011 Pyridine, 2-bromo-5-fluoro-

1.3 CAS No.: 41404-58-4

1.4 CID: 2783171

1.5 EINECS(EC#): 629-269-8

1.6 Molecular Formula: C5H3BrFN (isomer)

1.7 Inchi: InChI=1S/C5H3BrFN/c6-5-2-1-4(7)3-8-5/h1-3H

1.8 InChkey: UODINHBLNPPDPD-UHFFFAOYSA-N

1.9 Canonical Smiles: C1=CC(=NC=C1F)Br

1.10 Isomers Smiles: C1=CC(=NC=C1F)Br

2. Properties

2.1 Density: 1.707

2.1 Melting point: 30-31℃

2.1 Boiling point: 80-83℃ (44 mmHg)

2.1 Refractive index: 1.5396

2.1 Flash Point: 167?

2.1 Precise Quality: 174.94300

2.1 PSA: 12.89000

2.1 logP: 1.98320

2.1 Appearance: Colorless to slightly yellow Liquid

2.2 Storage: Ambient temperatures.

2.3 Chemical Properties: Light yellow Cryst

2.4 Color/Form: Colorless to slightly yellow

2.5 pKa: -1.63±0.10(Predicted)

2.6 StorageTemp: Store Cold

3. Use and Manufacturing

3.1 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).

3.2 Usage: 2-Bromo-5-fluoropyridine is used in the synthesis of mGluR5 antagonist for the treatment of neuropathic pain. 2-Bromo-5-fluoropyridineSupplier

4. Safety and Handling

4.1 Symbol: GHS07

4.1 Hazard Codes: Xi

4.1 Signal Word: Warning

4.1 Risk Statements: R36/37/38

4.1 Safety Statements: S26;S36

4.1 Packing Group: III

4.1 Hazard Class: IRRITANT

4.1 Hazard Declaration: H302-H315-H319-H335

4.1 RIDADR: 2811

4.1 Caution Statement: P261-P305 + P351 + P338

4.1 WGK Germany: 3

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Skin irritation, Category 2

Eye irritation, Category 2

Specific target organ toxicity \u2013 single exposure, Category 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H302 Harmful if swallowed H315 Causes skin irritation H319 Causes serious eye irritation H335 May cause respiratory irritation
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P280 Wear protective gloves/protective clothing/eye protection/face protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area.
Response	P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth. P302+P352 IF ON SKIN: Wash with plenty of water/... P321 Specific treatment (see ... on this label). P332+P313 If skin irritation occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P312 Call a POISON CENTER/doctor/\u2026if you feel unwell.
Storage	P403+P233 Store in a well-ventilated place. Keep container tightly closed. P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. Synthesis Route

41404-58-4Total: 1 Synthesis Route

21717-96-4 293 Suppliers

41404-58-4 261 Suppliers

Literatures:
Jaeschke, Georg; Kolczewski, Sabine; Porter, Richard Hugh Philip; Schnider, Patrick; Vieira, Eric Patent: US2007/78155 A1, 2007 ; Location in patent: Page/Page column 29 ; US 20070078155 A1
Yield: ~67%

7. Precursor and Product

precursor:

21717-96-4

product :

827579-38-4

802325-29-7

327056-62-2

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512171-81-2

1005291-43-9

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907208-90-6

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View all

8. Other Information

8.0 Storage Conditions: 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).

9. Computational chemical data

Molecular Weight: 175.988g/mol
Molecular Formula: C₅H₃BrFN
Compound Is Canonicalized: True
XLogP3-AA: 2
Exact Mass: 174.94329
Monoisotopic Mass: 174.94329
Complexity: 78.8
Rotatable Bond Count: 0
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 2
Topological Polar Surface Area: 12.9
Heavy Atom Count: 8
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADcQBiAQAAEAAAAAAAAAAAAAAAAAAAAAAsAAAAAAAAAAABgAAAHQBAAAABOADBEgw8gJIIEACgADBnRACCgCAxAiQI2CA4ZLgIIOLAkZGEIAhggADIyhYQAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==