24265-23-4|4-Bromo-3,6-dihydro-2H-pyran| Ambeed

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CAS No. :	24265-23-4
Formula :	C₅H₇BrO
M.W :	163.01
SMILES Code :	BrC1=CCOCC1
MDL No. :	MFCD10699698
InChI Key :	WSVCDRYCXKRMRC-UHFFFAOYSA-N
Pubchem ID :	46738829

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H227-H315-H319-H335
Precautionary Statements:	P305+P351+P338

Yield	Reaction Conditions	Operation in experiment
75%	With N-Bromosuccinimide; 1,8-diazabicyclo[5.4.0]undec-7-ene; toluene-4-sulfonic acid hydrazide In ethanol; dichloromethaneReflux	Step one: the tetrahydropyran-4-one (10.0 g, 0 . 1mol), paratoluene [...] (18.6 g, 0 . 1mol) and ethanol 120 ml after mixing, heating reflux reaction, after the reaction to evaporate the solvent, directly adding DBU (22.8 g, 0 . 15mol) and dichloromethane 150 ml in, then dropwise NBS (26.7 g, 0 . 15mol) dissolved in 40 ml of methylene chloride solution, after the reaction is complete, by adding 10percent hydrochloric acid to adjust PH= 4-5, separating the organic layer, evaporating the solvent at normal pressure, by adding 20 ml of sulfolane, vacuum distillation to obtain 12.2 g pale yellow liquid: 3,6-dihydro -2H-pyran-4-bromo, GC: 98.4percent, yield 75percent;
62%	With triphenyl phosphite; bromine; triethylamine In dichloromethane	Step 2: 4-Bromo-3,6-dihydro-2H-pyran 4.79 g (30.0 mmol) of bromine were added dropwise to a solution of 8.52 g (27.5 mmol) of triphenyl phosphite in 78 ml of anhydrous methylene chloride at -60° C. After addition of 4.5 ml (32.5 mmol) of triethylamine, a solution of 2.5 g (25.0 mmol) of tetrahydro-4H-pyran-4-one in 2 ml of methylene chloride was added dropwise. The reaction mixture was allowed to warm slowly (over approx. 5 h) to RT and stirring was continued at RT for a further approx. 10 h. All the volatile constituents were then removed on a rotary evaporator and the residue obtained was chromatographed coarsely by filtration with suction over approx. 100 g of silica gel with methylene chloride as the mobile phase. After renewed evaporation of the solvent, the product was isolated by means of bulb tube distillation (pressure: 8 mbar; temperature: to 120° C.). 2.51 g (62percent of th.) of the title compound were obtained. ¹H-NMR (400 MHz, CDCl₃, δ/ppm): 6.07 (m, 1H), 4.13 (m, 2H), 3.83 (m, 2H), 2.55-2.50 (m, 2H). GC/MS (method L, ESIpos): R_t=2.32 min, m/z=162/164 [M]⁺.

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CAS No.: 24265-23-4

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CAS No.: 24265-23-4

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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