Conditions | Yield |
---|---|
With hydrogen bromide In 1,4-dioxane at 5 - 20℃; for 0.5h; | 83% |
With hydrogen bromide for 1h; Ambient temperature; | 74% |
With hydrogen bromide at 5 - 10℃; | 50% |
2-(2-iodethyl)-[1,3]dioxane
ethylene dibromide
2-(2-Bromoethyl)-1,3-dioxane
Conditions | Yield |
---|---|
With tert.-butyl lithium 1) diethylether, -78 deg C, 5 min, r.t., 1h ; 2) -78 deg C; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In dichloromethane Ambient temperature; Yield given; | |
With toluene-4-sulfonic acid In dichloromethane at 20℃; for 8h; Inert atmosphere; | 252 g |
2-(2-Bromoethyl)-1,3-dioxane
bis(phenylsulfonyl)methane
5-(3,3-Bis-benzenesulfonyl-propyl)-[1,3]dioxane
Conditions | Yield |
---|---|
tetrabutylammomium bromide In sodium hydroxide at 25 - 30℃; for 3h; | 100% |
2-(2-Bromoethyl)-1,3-dioxane
(R,E)-2-methyl-N-(2-methylpropylidene)propane-2-sulfinamide
Conditions | Yield |
---|---|
Stage #1: 2-(2-Bromoethyl)-1,3-dioxane With iodine; magnesium In tetrahydrofuran at 20℃; for 1h; Stage #2: (R,E)-2-methyl-N-(2-methylpropylidene)propane-2-sulfinamide In tetrahydrofuran at -48℃; for 12h; Grignard addition; | 100% |
2-(2-Bromoethyl)-1,3-dioxane
Conditions | Yield |
---|---|
Stage #1: 2-(2-Bromoethyl)-1,3-dioxane With magnesium In tetrahydrofuran at 20 - 50℃; for 1h; Inert atmosphere; Stage #2: (R)-N-[(1Z)-[5-fluoro-2-(methylsulfanyl)phenyl]methylidene]-2-methylpropane-2-sulfinamide In tetrahydrofuran at -50 - 20℃; for 1h; Inert atmosphere; | 100% |
Stage #1: 2-(2-Bromoethyl)-1,3-dioxane With magnesium In tetrahydrofuran at 20 - 50℃; for 1h; Inert atmosphere; Stage #2: (R)-N-[(1Z)-[5-fluoro-2-(methylsulfanyl)phenyl]methylidene]-2-methylpropane-2-sulfinamide In tetrahydrofuran at -50 - 20℃; | 100% |
Stage #1: 2-(2-Bromoethyl)-1,3-dioxane With magnesium In tetrahydrofuran at 20 - 50℃; for 1h; Inert atmosphere; Stage #2: (R)-N-[(1Z)-[5-fluoro-2-(methylsulfanyl)phenyl]methylidene]-2-methylpropane-2-sulfinamide In tetrahydrofuran at -50 - 20℃; for 1h; Inert atmosphere; | 100% |
2-(2-Bromoethyl)-1,3-dioxane
butyl magnesium bromide
2-hexyl-1,3-dioxolane
Conditions | Yield |
---|---|
With [((Me)NN2)NiCl] In tetrahydrofuran; ISOPROPYLAMIDE at -35 - 20℃; Inert atmosphere; | 99% |
With buta-1,3-diene; nickel dichloride In tetrahydrofuran at -78 - 0℃; for 1h; Inert atmosphere; | 86% |
With 1-Phenylprop-1-yne; copper In tetrahydrofuran at 25℃; for 3h; Schlenk technique; Glovebox; | 74% |
With buta-1,3-diene; copper dichloride In tetrahydrofuran at 25℃; for 24h; Schlenk technique; Inert atmosphere; | 73 %Chromat. |
2-(2-Bromoethyl)-1,3-dioxane
allylmagnesium bromide
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; Inert atmosphere; Reflux; | 99% |
2-(2-Bromoethyl)-1,3-dioxane
Conditions | Yield |
---|---|
Stage #1: 2-(2-Bromoethyl)-1,3-dioxane With iodine; magnesium In tetrahydrofuran at 20 - 50℃; for 1.5h; Inert atmosphere; Stage #2: (R)-N-[(1Z)-[3-fluoro-5-(methylsulfanyl)phenyl]methylidene]-2-methylpropane-2-sulfinamide In tetrahydrofuran at -70 - 20℃; for 2h; | 99% |
Conditions | Yield |
---|---|
With magnesium | 98% |
2-(2-Bromoethyl)-1,3-dioxane
meta-hydroxybenzaldehyde
Conditions | Yield |
---|---|
Stage #1: 2-(2-Bromoethyl)-1,3-dioxane; meta-hydroxybenzaldehyde With potassium carbonate In acetonitrile at 80℃; for 18h; Stage #2: With sodium tetrahydroborate In methanol; dichloromethane at 0 - 20℃; for 2.25h; | 98% |
6-bromo-3,4-dihydroisoquinolin-1(2H)-one
2-(2-Bromoethyl)-1,3-dioxane
2-(2-(1,3-dioxan-2-yl)ethyl)-6-bromo-3,4-dihydroisoquinolin-1(2H)-one
Conditions | Yield |
---|---|
Stage #1: 6-bromo-3,4-dihydroisoquinolin-1(2H)-one With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.583333h; Stage #2: 2-(2-Bromoethyl)-1,3-dioxane In N,N-dimethyl-formamide for 16h; | 97% |
Stage #1: 6-bromo-3,4-dihydroisoquinolin-1(2H)-one With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.583333h; Inert atmosphere; Stage #2: 2-(2-Bromoethyl)-1,3-dioxane In N,N-dimethyl-formamide; mineral oil for 16h; Inert atmosphere; | 97% |
2-(2-Bromoethyl)-1,3-dioxane
Conditions | Yield |
---|---|
With magnesium In tetrahydrofuran; dichloromethane at -40 - 65℃; for 1h; Concentration; Reagent/catalyst; Temperature; Inert atmosphere; | 96.32% |
2-(2-Bromoethyl)-1,3-dioxane
1-indene
2-[2-(1H-inden-1-yl)ethyl]-1,3-dioxane
Conditions | Yield |
---|---|
With n-butyllithium In diethyl ether; hexane at -78 - 20℃; for 8.25h; Inert atmosphere; Schlenk technique; | 96% |
Stage #1: 1-indene With n-butyllithium In diethyl ether; hexane at 20℃; for 4h; Stage #2: 2-(2-Bromoethyl)-1,3-dioxane In diethyl ether; hexane at 20℃; for 16h; Further stages.; | 82% |
2-(2-Bromoethyl)-1,3-dioxane
phenylmagnesium chloride
2-(2-phenylethyl)-1,3-dioxane
Conditions | Yield |
---|---|
With N,N,N,N,-tetramethylethylenediamine; [((Me)NN2)NiCl] In tetrahydrofuran at 20℃; for 2h; Kumada-Corriu-Tamao coupling reaction; Inert atmosphere; | 96% |
With 1-Phenylprop-1-yne; copper In tetrahydrofuran at 80℃; for 12h; Schlenk technique; Glovebox; | 75% |
5-Norbornene-2-carboxaldehyde
2-(2-Bromoethyl)-1,3-dioxane
3-(1,3-dioxan-2-yl)-1-(5-norbornen-2-yl)-1-propanol
Conditions | Yield |
---|---|
With ammonium chloride In tetrahydrofuran | 95% |
2-(2-Bromoethyl)-1,3-dioxane
(2S,4aR,4bS,6aS,7aS,8aS,8bS,8cR,8dR,9aR,9bR)-2,9b-dihydroxy-4a,6a-dimethyloctadecahydro-7H-cyclopropa[4,5]cyclopenta[1,2-a]cyclopropa[l]phenanthren-7-one
17α-(2-[1,3]dioxan-2-ylethyl)-6β,7β,15β,16β-dimethylen-5β-androstane-3β,5,17β-triol
Conditions | Yield |
---|---|
Stage #1: 2-(2-Bromoethyl)-1,3-dioxane With magnesium; iodine In tetrahydrofuran at 55 - 60℃; for 1h; Stage #2: (2S,4aR,4bS,6aS,7aS,8aS,8bS,8cR,8dR,9aR,9bR)-2,9b-dihydroxy-4a,6a-dimethyloctadecahydro-7H-cyclopropa[4,5]cyclopenta[1,2-a]cyclopropa[l]phenanthren-7-one In tetrahydrofuran for 3.5h; Product distribution / selectivity; | 95% |
Stage #1: (2S,4aR,4bS,6aS,7aS,8aS,8bS,8cR,8dR,9aR,9bR)-2,9b-dihydroxy-4a,6a-dimethyloctadecahydro-7H-cyclopropa[4,5]cyclopenta[1,2-a]cyclopropa[l]phenanthren-7-one With lithium In tetrahydrofuran at -20℃; for 0.333333 - 0.5h; Stage #2: 2-(2-Bromoethyl)-1,3-dioxane In tetrahydrofuran at -20 - 0℃; for 2h; Product distribution / selectivity; | 74% |
2-(2-Bromoethyl)-1,3-dioxane
1,5-bis[(4R)-4-phenyl-3-(2,4,6-trimethoxybenzyl)-1,3-oxazolidin-2-yl]pentane
(2R,2'R)-2,2'-[1,9-bis(1,3-dioxan-2-yl)nonane-3(S),7(S)-diamino]bis(2-phenylethanol)
Conditions | Yield |
---|---|
Stage #1: 2-(2-Bromoethyl)-1,3-dioxane With magnesium In tetrahydrofuran Stage #2: 1,5-bis[(4R)-4-phenyl-3-(2,4,6-trimethoxybenzyl)-1,3-oxazolidin-2-yl]pentane In tetrahydrofuran at 60℃; for 48h; Stage #3: With water; ammonium chloride In tetrahydrofuran at 20℃; diastereoselective reaction; | 95% |
2-(2-Bromoethyl)-1,3-dioxane
2-(2-iodethyl)-[1,3]dioxane
Conditions | Yield |
---|---|
With sodium iodide In acetone Reflux; | 95% |
With sodium iodide In acetone | |
With sodium iodide In acetone |
2-(2-Bromoethyl)-1,3-dioxane
benzyl {4-[methoxy(methyl)amino]-4-oxobutyl}methylcarbamate
benzyl [6-(1,3-dioxan-2-yl)-4-oxohexyl]methylcarbamate
Conditions | Yield |
---|---|
Stage #1: 2-(2-Bromoethyl)-1,3-dioxane With iodine; magnesium In tetrahydrofuran at 65℃; Stage #2: benzyl {4-[methoxy(methyl)amino]-4-oxobutyl}methylcarbamate In tetrahydrofuran at 4 - 65℃; for 2h; | 95% |
Conditions | Yield |
---|---|
Stage #1: 2-(2-Bromoethyl)-1,3-dioxane With magnesium; iodine In tetrahydrofuran at 20℃; for 2h; Inert atmosphere; Stage #2: C27H26F3NO4S In tetrahydrofuran at -78℃; for 1.66667h; Stage #3: With ammonium chloride In tetrahydrofuran; water at -48℃; | 95% |
2-(2-Bromoethyl)-1,3-dioxane
Conditions | Yield |
---|---|
Stage #1: 2-(2-Bromoethyl)-1,3-dioxane With iodine; magnesium In tetrahydrofuran Inert atmosphere; Stage #2: phenyl 6-(benzyloxy)-2-methyl-4-[(1E)-{[(S)-2-methylpropane-2-sulfinyl]imino}methyl]-3-(trifluoromethyl)benzoate In tetrahydrofuran at -78℃; for 1.66667h; diastereoselective reaction; | 95% |
2-(2-Bromoethyl)-1,3-dioxane
zinc
Conditions | Yield |
---|---|
In tetrahydrofuran at 50℃; Inert atmosphere; Schlenk technique; | 95% |
2-(2-Bromoethyl)-1,3-dioxane
3,5,5-trimethylcyclopenten-2-one
4-<2-(1,3-Dioxan-2-yl)ethyl>-2,2,4-trimethylcyclopentanone
Conditions | Yield |
---|---|
Stage #1: 2-(2-Bromoethyl)-1,3-dioxane With iodine; magnesium; ethylene dibromide In tetrahydrofuran for 0.666667h; Heating; Stage #2: With copper(I) bromide dimethylsulfide complex In tetrahydrofuran at 5℃; for 0.166667h; Stage #3: 3,5,5-trimethylcyclopenten-2-one In tetrahydrofuran at 0 - 20℃; for 5.66667h; | 93% |
2-(2-Bromoethyl)-1,3-dioxane
Conditions | Yield |
---|---|
Stage #1: 2-(2-Bromoethyl)-1,3-dioxane With magnesium In tetrahydrofuran at -15 - 50℃; for 5h; Inert atmosphere; Stage #2: N-(3-pyridinemethylidene)-2-methylpropane-2-sulfinamide In tetrahydrofuran at -15 - 25℃; for 6h; | 92.7% |
2-(2-Bromoethyl)-1,3-dioxane
Conditions | Yield |
---|---|
With magnesium In tetrahydrofuran at 60℃; for 8h; | 92% |
2-(2-Bromoethyl)-1,3-dioxane
meta-hydroxybenzaldehyde
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile at 80℃; for 13h; | 92% |
2-(2-Bromoethyl)-1,3-dioxane
Conditions | Yield |
---|---|
With dichloro bis(acetonitrile) palladium(II); dipotassium hydrogenphosphate; norbornene In N,N-dimethyl acetamide at 90℃; for 22h; regioselective reaction; | 91% |
With dichloro bis(acetonitrile) palladium(II); dipotassium hydrogenphosphate; norbornene In N,N-dimethyl acetamide at 90℃; for 22h; regioselective reaction; | 91% |
Conditions | Yield |
---|---|
Stage #1: 2-(2-Bromoethyl)-1,3-dioxane With magnesium; ethylene dibromide In tetrahydrofuran at 23℃; for 1.5h; Inert atmosphere; Schlenk technique; Stage #2: With copper(l) cyanide; lithium chloride In tetrahydrofuran at -45 - 23℃; for 0.666667h; Inert atmosphere; Schlenk technique; Stage #3: (+)-(R)-6-methylcyclohex-2-en-1-one Further stages; | 91% |
Stage #1: 2-(2-Bromoethyl)-1,3-dioxane With magnesium; ethylene dibromide In tetrahydrofuran for 1.5h; Inert atmosphere; Stage #2: With copper(l) cyanide; lithium chloride In tetrahydrofuran at -45℃; for 0.666667h; Inert atmosphere; Stage #3: (+)-(R)-6-methylcyclohex-2-en-1-one Further stages; | 91% |
1-butylbenzimidazole
2-(2-Bromoethyl)-1,3-dioxane
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 20 - 80℃; for 5h; | 91% |
2-(2-Bromoethyl)-1,3-dioxane
Br(1-)*C23H29N2O5(1+)
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 25 - 80℃; for 10h; Inert atmosphere; | 90% |
2-(2-Bromoethyl)-1,3-dioxane
bis(pinacol)diborane
2-(2-(1,3-dioxan-2-yl)ethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Conditions | Yield |
---|---|
With lithium tert-butoxide In N,N-dimethyl-formamide at 25℃; for 16h; Inert atmosphere; Schlenk technique; | 90% |
With potassium tert-butylate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; copper(l) chloride In tetrahydrofuran at 20℃; for 5h; Inert atmosphere; | 86% |
Stage #1: bis(pinacol)diborane With potassium tert-butylate; [1,3-bis(2,4,6-trimethylphenyl)imidazol]-2-ylidene; zinc(II) chloride In tert-butyl methyl ether for 0.5h; Inert atmosphere; Schlenk technique; Glovebox; Stage #2: 2-(2-Bromoethyl)-1,3-dioxane In tert-butyl methyl ether at 20℃; for 2h; Inert atmosphere; Schlenk technique; Glovebox; | 84% |
2-(2-Bromoethyl)-1,3-dioxane
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 20℃; for 5h; Inert atmosphere; Schlenk technique; | 90% |
In N,N-dimethyl-formamide at 20 - 80℃; for 5h; |
The 2-(2-Bromoethyl)-1,3-dioxane, with the CAS registry number 33884-43-4 and EINECS registry number 251-716-7, belongs to the following product categories: Aliphatics; Halides; Dioxanes; Dioxanes & Dioxolanes. It should be stored at 2-8°C. And the molecular formula of the chemical is C6H11BrO2.
The characteristics of 2-(2-Bromoethyl)-1,3-dioxane are as followings: (1)ACD/LogP: 0.85; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.85; (4)ACD/LogD (pH 7.4): 0.85; (5)ACD/BCF (pH 5.5): 2.62; (6)ACD/BCF (pH 7.4): 2.62; (7)ACD/KOC (pH 5.5): 69.36; (8)ACD/KOC (pH 7.4): 69.36; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 18.46 Å2; (13)Index of Refraction: 1.467; (14)Molar Refractivity: 38.71 cm3; (15)Molar Volume: 139.2 cm3; (16)Polarizability: 15.34×10-24cm3; (17)Surface Tension: 37.9 dyne/cm; (18)Density: 1.4 g/cm3; (19)Flash Point: 96.7 °C; (20)Enthalpy of Vaporization: 43.89 kJ/mol; (21)Boiling Point: 221.1 °C at 760 mmHg; (22)Vapour Pressure: 0.162 mmHg at 25°C.
Preparation of 2-(2-Bromoethyl)-1,3-dioxane: This chemical can be prepared by propenal and propane-1,3-diol. The reaction will need reagent HBr. The reaction time is 1 hour with ambient temperature, and the yield is about 74%.
Uses of 2-(2-Bromoethyl)-1,3-dioxane: It can react with [1,3]dithiane to produce 2-(1,3-Dioxan-2-yl)-1-(1,3-dithianyl)ethane. This reaction will need reagent HMPT, and the menstruum tetrahydrofuran. The yield is about 86%.
You should be cautious while dealing with this chemical. It irritates to eyes, respiratory system and skin. Therefore, if in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.
Addtionally, the following datas could be converted into the molecular structure:
(1)SMILES: BrCCC1OCCCO1
(2)InChI: InChI=1/C6H11BrO2/c7-3-2-6-8-4-1-5-9-6/h6H,1-5H2
(3)InChIKey: WMDHQEHPOVOEOG-UHFFFAOYAA
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