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CAS No. :	766-11-0
Formula :	C₅H₃BrFN
M.W :	175.99
SMILES Code :	FC1=NC=C(Br)C=C1
MDL No. :	MFCD01863742
InChI Key :	MYUQKYGWKHTRPG-UHFFFAOYSA-N
Pubchem ID :	2783168

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Yield	Reaction Conditions	Operation in experiment
86%	In tetrahydrofuran; water; at 110℃;Sealed tube;	To sealed tube was added 5-bromo-2-fluoropyridine (825 mg, 5.1 mmol), dimethylamine/water (7.0 mL, 33%) and THF (3.0 mL), then sealed and heated to 110 C overnight. The reaction mixture was cooled to RT and extracted with EA, the organic layers were combined and washed with brine, then dried over a2S04 and concentrated to give compound 2-dimethylamino-5- bromopyridine as yellow oil (880 mg, yield 86%). Coupling under standard conditions gave 127 mg from 300 mg of 6-methyl-N-{4-[4-(tetramethyl-l,3,2-dioxaborolan-2-yl)phenyl]-l,3-thiazol- 2-yl}pyridin-2-amine, yellow solid, 43% yield.
75%	In tetrahydrofuran; at 100℃;Sealed tube;	To a sealed tube was added 5-bromo-2-fluoropyridine (2.0 g, 1 1 .36 mmol), dimethylamine (7.0 mL, 45.6 mmol) in water and tetrahydrofuran (3 mL) and the reaction was heated to 100 C overnight. The reaction mixture was cooled to room temperature and extracted with EtOAc (15 mL x 3), the organic layers were combined and washed with brine and dried over Na2S04, filtered and concentrated under reduced pressure to give 5-bromo-N,N-dimethylpyridin-2-amine (1 .7 g, 8.46 mmol, 75 % yield) as a white solid.

Yield	Reaction Conditions	Operation in experiment
72%	With palladium diacetate; tricyclohexylphosphine; In 1,2-dimethoxyethane; water; at 80℃;	A mixture of 5-bromo-2-fluoropyridine (435 mg, 2.5 mmol), cyclopropylboronic acid (260 mg, 3.0 mmol), potassium phosphate (1.27 g, 6.0 mmol), palladium (II) acetate (56 mg, 0.6 mmol) and tricyclohexyl phosphine (340 mg, 1.2 mmol) in 1,2- dimethoxyethane/water (10.0 mL/2.0 mL) was stirred at 80 C overnight. The mixture was cooled and concentrated to dryness. The residue was purified by flash chromatography (petroleum ether / ethyl acetate = 3/1) to afford 5-cyclopropyl-2- fluoropyridine (246 mg, 1.8 mmol, 72% yield) as yellow solid. LCMS: m/z = 138.1 [M+H]+, retention time = 2.25 min (Method A).
647 mg	With potassium phosphate; palladium diacetate; tricyclohexylphosphine; In water; toluene; at 80℃; for 16h;Inert atmosphere;	5-Bromo-2-fluoro - pyridine (1.41 g, 8 mmol) and cyclopropyl boronicacid (1.37 g, 16 mmol) mixed in toluene / water (26 mL / 1.3 mL), to which was added potassium phosphate (7.46 Under g, 28 mmol), argon was added theretopalladium acetate (90 mg, 0.4 mmol) and tricyclohexylphosphine (224 mg, 0.8mmol), the mixture was heated to 80 C the reaction 16h. After completion of the reaction by TLC, cooled to room temperature,water was added thereto, extracted with ethyl acetate, the organic phase wasdried over anhydrous sodium sulfate, filtered, and the solvent was evaporatedto dryness, purified by silica gel column chromatography to give 5-cyclopropyl-2-fluoro- pyridine (yellow oil, 647 mg).

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CAS No.: 766-11-0

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CAS No.: 766-11-0

Alternative Products

Product Details of 5-Bromo-2-fluoropyridine

Safety of 5-Bromo-2-fluoropyridine

Application In Synthesis of 5-Bromo-2-fluoropyridine

[ 766-11-0 ] Synthesis Path-Downstream 1~6

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Yield	Reaction Conditions	Operation in experiment
83%		Sodium hydride (0.591g, 14.77mmol) was added portionwise to a solution of 3-(pyrrolidin- l-yl)propan-l-ol (1.615g, 12.50mmol) in THF (20mL) at to 0°C then stirred at ambient temperature for 30 minutes. 5-Bromo-2-fluoropyridine (2g, 11.36mmol) was added and the resulting mixture stirred at ambient temperature for 2 h before being quenched by the addition of a sat. aqueous solution of ammonium chloride. The moisture was extracted with EtOAc (2 x lOOmL), the organic layer dried over Na2SC>4, filtered and evaporated to afford pale yellow solid. The crude product was purified by FCC, elution gradient 0 to 10percent MeOH in DCM, to afford the desired material (2.70g, 83percent) as a yellow solid.
83%		Sodium hydride (0.59 1 g, 14.77 mmol) was added portionwise to a solution of 3- (pyrrolidin-1-yl)propan-1-ol(1.615 g, 12.50 mmol) in THF (20 mL) at to 0°C then stirred at ambient temperature for 30 minutes. 5-Bromo-2-fluoropyridine (2 g, 11.36 mmol) wasadded and the resulting mixture stirred at ambient temperature for 2 h before being quenched by the addition of a saturated aqueous solution of ammonium chloride. The mixture was extracted with EtOAc (2 x 100 mL), the organic layer dried over Na2SO4, filtered and evaporated to afford pale yellow solid. The crude product was purified byFCC, elution gradient 0 to 10percent MeOH in DCM, to afford the desired material (2.70 g, 83percent) as a yellow solid. Mass Spectrum: m/z (ES+)[M+H]+ = 285.

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
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P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
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P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
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P411
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P413
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P402 + P404	Store in a dry place. Store in a closed container.
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P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
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H222	Extremely flammable aerosol
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H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed