1246184-55-3|7-Bromo-3-iodoimidazo[1,2-a]pyridine| Ambeed

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CAS No. :	1246184-55-3
Formula :	C₇H₄BrIN₂
M.W :	322.93
SMILES Code :	IC1=CN=C2C=C(Br)C=CN21
MDL No. :	MFCD22571345

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Yield	Reaction Conditions	Operation in experiment
86.9%	With N-iodo-succinimide; In N,N-dimethyl-formamide; at 100℃; for 1h;	To a solution of 7-bromoimidazo[l,2-a]pyridine (5.93 g, 30.1 mmol) in DMF (60 mL) was added NIS (9.19 g, 40.8 mmol). The reaction mixture was stirred at 100 C for 1 hour, then cooled down to rt and quenched with water (50 mL), then extracted with DCM (100 mL x 3). The combined organic phases were washed with brine (100 mL), dried over anhydrous Na2S04, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/PE (v/v) = 1/10) to give the title compound as a yellow solid (8.45 g, yield 86.9%).MS (ESI, pos. ion) m/z: 323.0 [M+H]+;1H NMR (400 MHz, CDCl3) d (ppm): 8.02 (d, J= 7.3 Hz, 1H), 7.83 (d, J= 1.2 Hz, 1H), 7.69 (s, 1H), 7.05 (dd, j= 7.3, 1.7 Hz, 1H).
86.9%	With N-iodo-succinimide; In N,N-dimethyl-formamide; at 100℃; for 1h;	To <strong>[808744-34-5]7-bromoimidazo[1,2-a]pyridine</strong> (5.93 g, 30.1 mmol)Add in DMF (60mL) solutionNIS (9.19 g, 40.8 mmol).The reaction mixture was stirred at 100 C for 1 hour.Then cool to room temperature,The reaction was quenched by the addition of water (50 mL).It was then extracted with DCM (100 mL x 3).Combined organic phase with saturated brine (100 mL)Washed, dried over anhydrous sodium sulfate,Filter and concentrate under reduced pressure.The residue obtained was purified by silica gel column chromatography (EtOAc /EtOAcThe title compound was obtained as a white solid (8.45 g, yield 86.9%).
	With iodine; sodium acetate; In methanol; at 0℃;	(2) 7-bromo-3-iodoimidazo[l,2-a]pyridine.; To a 250 mL round bottomed flask was added 7-bromoimidazo[l,2-a]pyridine (3.8 g, 19.29 mmol), sodium acetate (4.3 g, 52.1 mmol) and MeOH (60 mL). The resulting mixture was cooled to 0 0C followed by adding diiodine (8.3 g, 32.8 mmol). After the addition, ice bath was removed and the mixture was continued to stir for 5 h. The solvent was concentrated. The crude product was purified using SiO2 chromatography (Teledyne Isco RediSep, 330 g SiO2, hexanes:acetone= 80%:20%, Flow = 100 mL/min). The solvent was removed in vacuo to afford the desired product as light yellow solid (3.2 g). (ESI pos. ion) m/z: 322.8. Calcd exact mass for C7H4BrIN2: 321.9. 1H NMR (300 MHz, CHLOROFORM-^) delta ppm 7.04 (d, J=7.02 Hz, 1 H) 7.68 (s, 1 H) 7.82 (s, 1 H) 8.01 (d, J=7.31 Hz, I H).

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P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
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P337 + P313	IF eye irritation persists: Get medical advice/attention.
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P401
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CAS No.: 1246184-55-3

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CAS No.: 1246184-55-3

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[ 1246184-55-3 ] Synthesis Path-Downstream 1~1

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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
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
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