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Chemical Structure| 4360-63-8

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Product Details of 2-Bromomethyl-1,3-dioxolane

CAS No. :4360-63-8
Formula : C4H7BrO2
M.W : 167.00
SMILES Code : BrCC1OCCO1
MDL No. :MFCD00003214
InChI Key :CKIIJIDEWWXQEA-UHFFFAOYSA-N
Pubchem ID :78068

Safety of 2-Bromomethyl-1,3-dioxolane

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H227
Precautionary Statements:P501-P210-P264-P280-P302+P352-P370+P378-P337+P313-P305+P351+P338-P362+P364-P332+P313-P403+P235

Application In Synthesis of 2-Bromomethyl-1,3-dioxolane

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 4360-63-8 ]

[ 4360-63-8 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 4360-63-8 ]
  • [ 20146-59-2 ]
  • [ 917835-14-4 ]
YieldReaction ConditionsOperation in experiment
To 20 mL of an N,N-dimethylformamide solution containing 540 mg of <strong>[20146-59-2]4-chloroquinolin-2(1H)-one</strong>, 376 mg of 60% sodium hydride was added, and the mixture was stirred at room temperature for 1 hour. Thereto was added 3.2 mL of 2-bromomethyl-1,3-dioxolane, and the mixture was stirred at 90C for 16 hours. The reaction mixture was cooled to room temperature, and then ethyl acetate and 1 mol/L hydrochloric acid were added thereto. The organic layer was separated, the resultant solution was washed sequentially with water and an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [silica gel; Silica gel 60 manufactured by Kanto Chemical Co., Inc., eluent; ethyl acetate : hexane = 1 : 1] to obtain 165 mg of a white solid, 1-(1,3-dioxolan-2-ylmethyl)-<strong>[20146-59-2]4-chloroquinolin-2(1H)-one</strong>. 1H-NMR (CDCl3) delta: 3.84-3.92 (2H, m), 3.99-4.05 (2H, m), 4.54 (2H, d, J=4.4 Hz), 5.25 (1H, t, J=4.4 Hz), 6.91 (1H, s), 7.24-7.37 (1H, m), 7.60-7.68 (2H, m), 8.02 (1H, d, J=7.9 Hz)
  • 2
  • [ 4360-63-8 ]
  • [ 101382-55-2 ]
  • [ 917833-22-8 ]
YieldReaction ConditionsOperation in experiment
To 30 mL of an N,N-dimethylformamide solution containing 1.5 g of <strong>[101382-55-2]7-methoxy-2-oxo-1,2-dihydroquinoline-3-carbaldehyde</strong>, 0.32 g of 60% sodium hydride was added, and the mixture was stirred at 50C for 30 minutes. Thereto was added 1.53 mL of 2-bromomethyl-1,3-dioxolane, and the reaction mixture was stirred at 80 to 90C for 2 hours. Thereto was added 1.53 mL of 2-bromomethyl-1,3-dioxolane, and the reaction mixture was stirred for 3 hours and 30 minutes. Water and ethyl acetate were then added thereto, and the reaction mixture was adjusted to pH 1.5 with 6 mol/L hydrochloric acid. The organic layer was separated, and the aqueous layer was extracted twice with ethyl acetate. The organic layer and the extract were combined, the resultant solution was washed with an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was added with a mixed solution of diethyl ether and ethyl acetate, and a solid substance collected by filtration, and then purified by silica gel column chromatography [eluent; chloroform] to obtain 0.35 g of a yellow solid, 1-(1,3-dioxolan-2-ylmethyl)-<strong>[101382-55-2]7-methoxy-2-oxo-1,2-dihydroquinoline-3-carbaldehyde</strong>. 1H-NMR (CDCl3) delta: 3.88-3.93 (2H, m), 3.95 (3H, s), 4.00-4.10 (2H, m), 4.56 (2H, d, J=4.3 Hz), 5.26 (1H, t, J=4.3 Hz), 6.88 (1H, dd, J=8.8, 2.2 Hz), 7.09 (1H, d, J=2.2 Hz), 7.63 (1H, d, J=8.8 Hz), 8.32 (1H, s), 10.42 (1H, s)
  • 3
  • [ 4360-63-8 ]
  • [ 15944-34-0 ]
  • [ 959615-88-4 ]
YieldReaction ConditionsOperation in experiment
To a solution of 3.2 g of <strong>[15944-34-0]7-chloro-1,8-naphthyridin-2(1H)-one</strong> in 32 mL of N,N-dimethylformamide, 3.7 g of potassium carbonate was added, and the mixture was stirred at 50 to 60C for 23 minutes, and then, thereto was added 2.2 mL of 2-bromomethyl-1,3-dioxolan, and the mixture was stirred at 60 to 78C for 25 minutes. Thereto were added 16 mL of N,N-dimethylformamide and 1.1 mL of 2-bromomethyl-1,3-dioxolan, the mixture was stirred at 90 to 95C for 2 hours 15 minutes, 3.7 g of potassium carbonate was added thereto, and the mixture was stirred for 20 minutes. The reaction mixture was cooled to room temperature, water and ethyl acetate were then added thereto, the organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined, the resultant solution was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The resultant residue was purified by silica gel column chromatography using an eluent of hexane:ethyl acetate = 1:1 to obtain 3.6 g of 7-chloro-1-(1,3-dioxolan-2-ylmethyl)-1,8-naphthyridin-2(1H)-one as a yellow solid. 1H-NMR (CDCl3) delta: 3.86-3.96 (2H, m), 4.10-4.20 (2H, m), 4.63 (2H, t, J = 5.4 Hz), 5.60 (1H, t, J = 5.4 Hz), 6.75 (1H, d, J = 9.6 Hz), 7.17 (1H, d, J = 8.0 Hz), 7.62 (1H, d, J = 9.6 Hz), 7.79 (1H, d, J = 8.0 Hz)
  • 4
  • [ 4360-63-8 ]
  • [ 610791-05-4 ]
  • C14H23NO6 [ No CAS ]
  • 5
  • [ 4360-63-8 ]
  • [ 603-76-9 ]
  • [ 2932-65-2 ]
  • 9-methyl-1-(4-propylphenyl)-9H-carbazole [ No CAS ]
  • 6
  • [ 4360-63-8 ]
  • [ 61019-05-4 ]
  • [ 98-86-2 ]
  • 3-methoxy-1-methyl-8-phenyl-9H-carbazole [ No CAS ]
  • 8
  • [ 4360-63-8 ]
  • [ 50551-10-5 ]
  • [ 108290-86-4 ]
YieldReaction ConditionsOperation in experiment
93.6% 167 g, i.e., 1 mol of 2-bromomethyl-1,3-dioxolane (i.e., a compound of formula III) was added to 500 ml of 2-methyltetrahydrofuran to give 2-bromomethyl-1,3-dioxolane. The organic mixed solution is controlled to a temperature below 10 C; and then 100 ml of sulfuric acid (0.18 moL) with a mass fraction of 10% is added dropwise to the organic mixed solution of 2-bromomethyl-1,3-dioxolane. After stirring for 20 minutes, the liquid was separated, and 174 g of 1.33 mol of ethyl 3-amino-3-iminopropanoate (the compound of formula II) was added portionwise in the organic phase, and the mixture was heated to reflux at 100 C until the reaction was completed, and the filtrate was filtered. Concentration gave 144 g of 2-amino-3-carboxypyrroleethyl ester in a yield of 93.6%.The next step reaction is carried out without purification.
 

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