Conditions | Yield |
---|---|
With sodium bromide | 85% |
With lithium bromide In acetone for 12h; Finkelstein reaction; Inert atmosphere; | 21% |
With acetone; sodium bromide | |
With methanol; sodium bromide | |
With sodium bromide |
Conditions | Yield |
---|---|
With phosphorus tribromide In pyridine 1.) -20 deg C, 4 h; 2.) room temperature, 2 h; | 55% |
With phosphorus tribromide at 30℃; for 2h; | 55% |
With phosphorus tribromide at 30℃; Inert atmosphere; | 50% |
A
2-methyl-3-bromo-1-propene
Conditions | Yield |
---|---|
In diethyl ether 2 h at 25°C under Ar or N2; chromy on Al2O3 with pentane, distn.; | A n/a B 55% |
In diethyl ether 2 h at 25°C under Ar or N2; chromy on Al2O3 with pentane, distn.; | A n/a B 55% |
1,2-dibromo-2-methyl-propane
A
2-methyl-3-bromo-1-propene
B
t-butyl bromide
Conditions | Yield |
---|---|
With copper at 390 - 400℃; |
Conditions | Yield |
---|---|
With methanol; amalgamated zinc |
(E)-but-2-enol
A
2-methyl-3-bromo-1-propene
B
(Z)-crotyl bromide
C
(E)-1-Bromo-2-butene
Conditions | Yield |
---|---|
With phosphorus tribromide In dichloromethane at 0 - 5℃; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
isobutene
A
2-methyl-3-bromo-1-propene
B
N-(2-bromo-2-methyl-1-propyl)succinimide
Conditions | Yield |
---|---|
With N-Bromosuccinimide In dichloromethane at 15℃; Irradiation; competition reaction with 3,3-dimethyl-1-butene and methylene chloride; |
methanol
3-Chloro-2-methylpropene
A
2-methyl-3-bromo-1-propene
B
1,2-dimethoxy-2-methylpropane
C
methallyl methyl ether
D
isobutyraldehyde dimethyl acetal
2-methyl-3-bromo-1-propene
Conditions | Yield |
---|---|
With pyridine; phosphorus tribromide |
Conditions | Yield |
---|---|
With acetone |
1,2-dibromo-2-methyl-propane
A
2-methyl-3-bromo-1-propene
B
t-butyl bromide
Conditions | Yield |
---|---|
at 390 - 400℃; |
methanol
1,2,3-tribromo-2-methylpropane
A
2-methyl-3-bromo-1-propene
B
methallyl methyl ether
Conditions | Yield |
---|---|
anfangs unter Kuehlung; |
Conditions | Yield |
---|---|
With N-Bromosuccinimide; toluene-4-sulfonic acid at 100℃; for 4h; Inert atmosphere; | |
With N-Bromosuccinimide; toluene-4-sulfonic acid In tetrahydrofuran at 100℃; for 4h; Inert atmosphere; Schlenk technique; |
isobutene
A
2-methyl-3-bromo-1-propene
B
1,2-dibromo-2-methyl-propane
C
1-bromo-2-methylpropane-2-ol
Conditions | Yield |
---|---|
With hydrogen bromide; oxygen; sodium nitrite In water at 40℃; under 760.051 Torr; Ionic liquid; |
phenylacetic acid
2-methyl-3-bromo-1-propene
(±)-4-methyl-2-phenyl-4-pentenoic acid
Conditions | Yield |
---|---|
Stage #1: phenylacetic acid With lithium diisopropyl amide In tetrahydrofuran at 20℃; for 0.5h; Stage #2: 2-methyl-3-bromo-1-propene In tetrahydrofuran at 20℃; | 100% |
Stage #1: phenylacetic acid With lithium diisopropyl amide In tetrahydrofuran; n-heptane; ethylbenzene at -78 - 0℃; for 0.5h; Inert atmosphere; Stage #2: 2-methyl-3-bromo-1-propene In N,N-dimethyl-formamide; mineral oil at -78℃; for 2h; Inert atmosphere; | 93% |
With lithium diisopropyl amide 1.) THF, 0 deg C, then 25 deg C, 1 h and 60 deg C, 0.5 h, 2.) 0 deg C, then 25 deg C, 16 h; Multistep reaction; | |
Stage #1: phenylacetic acid With n-butyllithium In tetrahydrofuran; hexanes at 0℃; Inert atmosphere; Stage #2: 2-methyl-3-bromo-1-propene In tetrahydrofuran; hexanes at -78℃; for 0.333333h; Inert atmosphere; |
Conditions | Yield |
---|---|
With manganese; copper dichloride In water for 16h; Ambient temperature; | 100% |
With tetraethylammonium perchlorate; sodium iodide In N,N-dimethyl-formamide electrochemical reaction; | 100 % Chromat. |
2-methyl-3-bromo-1-propene
N-(diphenylmethylene)glycine tert-butyl ester
tert-butyl 2-[(diphenylmethylidene)amino]-4-methylpent-4-enoate
Conditions | Yield |
---|---|
With potassium hydroxide; 2(2CF3Ph)2tBu-2MeO-Me(R)Napht-yl-Et-diH-5Hdibenzo-azepinium; water In toluene at 0℃; for 1h; | 100% |
Stage #1: 2-methyl-3-bromo-1-propene; N-(diphenylmethylene)glycine tert-butyl ester With tetrabutylammomium bromide In dichloromethane at 0℃; for 0.166667h; Stage #2: With potassium hydroxide In dichloromethane; water at 20℃; for 18h; | 92% |
With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; | |
Stage #1: N-(diphenylmethylene)glycine tert-butyl ester With sodium hydride In tetrahydrofuran Stage #2: 2-methyl-3-bromo-1-propene | |
With sodium hydride In tetrahydrofuran |
2-methyl-3-bromo-1-propene
Conditions | Yield |
---|---|
Stage #1: Merrifield resin, 2 percent DVB cross-linking, DF 57 percent With 4,4'-di-tert-butylbiphenyl; lithium In tetrahydrofuran at 20℃; for 4h; Stage #2: 2-methyl-3-bromo-1-propene In tetrahydrofuran at -78 - 25℃; for 4h; Stage #3: With water In tetrahydrofuran | 100% |
Conditions | Yield |
---|---|
Stage #1: 2-Hydroxyphenylacetic acid With potassium hydroxide at 40℃; for 0.166667h; Stage #2: 2-methyl-3-bromo-1-propene In N,N-dimethyl-formamide at 20℃; | 100% |
2-methyl-3-bromo-1-propene
4-acetamido-3-bromoacetophenone
N-(4-acetyl-2-bromophenyl)-N-(2-methylallyl)acetamide
Conditions | Yield |
---|---|
With sodium hydride In DMF (N,N-dimethyl-formamide) at 25℃; for 17h; | 100% |
2-methyl-3-bromo-1-propene
(2R,4R)-3-<(Benzyloxy)carbonyl>-4-methyl-2-phenyl-1,3-oxazolidin-5-one
C22H23NO4
Conditions | Yield |
---|---|
Stage #1: (2R,4R)-3-<(Benzyloxy)carbonyl>-4-methyl-2-phenyl-1,3-oxazolidin-5-one With lithium hexamethyldisilazane In tetrahydrofuran at -60℃; for 0.5h; Large scale; Stage #2: 2-methyl-3-bromo-1-propene In tetrahydrofuran at -60℃; for 8h; Temperature; Large scale; | 100% |
With potassium hexamethylsilazane In tetrahydrofuran; toluene at -35 - -30℃; for 4.5h; | 90% |
2-methyl-3-bromo-1-propene
5,6,7,8-tetrahydro-5-oxoimidazo[1,5-c]pyrimidine
2-(2-methylprop-2-enyl)-5-oxo-5,6,7,8-tetrahydroimidazo[1,5-c]pyrimidin-2-ium bromide
Conditions | Yield |
---|---|
In acetonitrile at 85℃; for 72h; | 100% |
In acetonitrile at 95℃; for 15h; Inert atmosphere; | 100% |
4-hydroxy-1-(pyrrolidin-1-yl)butan-1-one
2-methyl-3-bromo-1-propene
4-((2-methylallyl)oxy)-1-(pyrrolidin-1-yl)butan-1-one
Conditions | Yield |
---|---|
Stage #1: 4-hydroxy-1-(pyrrolidin-1-yl)butan-1-one With sodium hydride In tetrahydrofuran; mineral oil at 0℃; Inert atmosphere; Stage #2: 2-methyl-3-bromo-1-propene In tetrahydrofuran; mineral oil at 0 - 20℃; Inert atmosphere; | 100% |
2-methyl-3-bromo-1-propene
N-[(3,3-dimethylcycloprop-1-enyl)phenylmethyl]-4-methylbenzenesulfonamide
N-[(3,3-dimethylcycloprop-1-enyl)phenylmethyl]-4-methyl-N-(2-methylallyl)benzenesulfonamide
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 2h; | 100% |
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 2h; | 99% |
3-benzyloxy-phenylacetic acid methyl ester
2-methyl-3-bromo-1-propene
methyl 2-(3-(benzyloxy)phenyl)-4-methylpent-4-enoate
Conditions | Yield |
---|---|
Stage #1: 3-benzyloxy-phenylacetic acid methyl ester With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Cooling with ethanol-dry ice; Stage #2: 2-methyl-3-bromo-1-propene In tetrahydrofuran at -78℃; | 100% |
Stage #1: 3-benzyloxy-phenylacetic acid methyl ester With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 1h; Stage #2: 2-methyl-3-bromo-1-propene In tetrahydrofuran at -78 - 20℃; | 100% |
2-methyl-3-bromo-1-propene
ethyl N-(t-butyloxycarbonyl)nipecotate
1-tert-butyl 3-ethyl 3-(2-methylprop-2-en-1-yl)piperidine-1,3-dicarboxylate
Conditions | Yield |
---|---|
Stage #1: ethyl N-(t-butyloxycarbonyl)nipecotate With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.5h; Stage #2: 2-methyl-3-bromo-1-propene In tetrahydrofuran at -78 - 20℃; | 100% |
2-methyl-3-bromo-1-propene
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
4,4,5,5-tetramethyl-2-(2-methylallyl)-1,3,2-dioxaborolane
Conditions | Yield |
---|---|
With magnesium In tetrahydrofuran at 25℃; for 2.08333h; Inert atmosphere; | 100% |
With magnesium In tetrahydrofuran at 25℃; for 2.5h; | 69% |
With magnesium In tetrahydrofuran at 20℃; for 2h; Inert atmosphere; Schlenk technique; | 65% |
Conditions | Yield |
---|---|
Stage #1: C10H10F3IN2 With TurboGrignard In tetrahydrofuran at -20℃; for 0.5h; Inert atmosphere; Stage #2: 2-methyl-3-bromo-1-propene With copper(I) cyanide di(lithium chloride) In tetrahydrofuran at -20℃; for 1.5h; | 100% |
2-methyl-3-bromo-1-propene
dimethyl 4-pentenylmalonate
Conditions | Yield |
---|---|
Stage #1: dimethyl 4-pentenylmalonate With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h; Stage #2: 2-methyl-3-bromo-1-propene In tetrahydrofuran; mineral oil at 0 - 20℃; | 100% |
Conditions | Yield |
---|---|
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 5h; | 100% |
Conditions | Yield |
---|---|
Stage #1: thymin In acetonitrile for 0.0833333h; Inert atmosphere; Reflux; Stage #2: 2-methyl-3-bromo-1-propene With chloro-trimethyl-silane; sodium iodide In acetonitrile for 16h; Inert atmosphere; Reflux; | 100% |
Conditions | Yield |
---|---|
With ammonium acetate; zinc In tetrahydrofuran at 0℃; for 0.166667h; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
Stage #1: 2-decyn-1-ol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 0.5h; Williamson Ether Synthesis; Stage #2: 2-methyl-3-bromo-1-propene In N,N-dimethyl-formamide; mineral oil at 20℃; Williamson Ether Synthesis; | 100% |
2-methyl-3-bromo-1-propene
(+)-dimethyl-2,3-O-isopropylidene-D-tartrate
Conditions | Yield |
---|---|
With lithium hexamethyldisilazane In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide at -78℃; for 4h; diastereoselective reaction; | 100% |
2-methyl-3-bromo-1-propene
methyl N-(diphenylmethylene)glycinate
Methyl 2-amino-4-methylpent-4-enoate
Conditions | Yield |
---|---|
Stage #1: 2-methyl-3-bromo-1-propene; methyl N-(diphenylmethylene)glycinate With tetra-(n-butyl)ammonium iodide; caesium carbonate In acetonitrile for 4h; Inert atmosphere; Reflux; Stage #2: With hydrogenchloride In water; acetonitrile at 20℃; for 0.5h; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
With zinc In N,N-dimethyl-formamide for 0.5h; Ambient temperature; | 99% |
With indium; water In tetrahydrofuran at 20℃; |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; | 99% |
With potassium carbonate In acetone Heating; Yield given; | |
With potassium carbonate In acetonitrile at 60℃; |
2-methyl-3-bromo-1-propene
1,2:5,6-di-O-isopropylidene-α-D-glucofuranose
5-[2,2-dimethyl-(4R)-1,3-dioxolan-4-yl]-2,2-dimethyl-(3aR,5R,6S,6aR)-perhydrofuro[2,3-d][1,3]dioxol-6-yl 2-methylallyl ether
Conditions | Yield |
---|---|
Stage #1: 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose With sodium hydride In tetrahydrofuran at 0 - 20℃; Stage #2: 2-methyl-3-bromo-1-propene With tetra-(n-butyl)ammonium iodide In tetrahydrofuran at 20℃; for 16h; | 99% |
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 1h; | 66% |
With sodium hydride In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide Alkylation; |
2-methyl-3-bromo-1-propene
2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid tert-butyl ester
Conditions | Yield |
---|---|
With potassium hydroxide; tetrabutylammomium bromide In toluene at 25℃; for 0.4h; | 99% |
2-methyl-3-bromo-1-propene
(4S)-6-methyl-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]hepta-1,2-diene
N-[(1S)-1-isobutylbuta-2,3-dienyl]-N-(2-methylprop-2-enyl)-2,4,6-trimethylphenylsulfonamide
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 0℃; | 99% |
2-methyl-3-bromo-1-propene
(4S,5S)-5-methyl-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]hepta-1,2-diene
N-(2-methylprop-2-enyl)-N-{(1S)-1-[(1S)-1-methylpropyl]-2,3-butadienyl}-2,4,6-trimethylphenylsulfonamide
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 0℃; | 99% |
2-(benzhydrylidene-amino)-N-benzyl-N-methoxy-acetamide
2-methyl-3-bromo-1-propene
Conditions | Yield |
---|---|
With potassium hydroxide; N-spiro chiral quaternary ammonium bromide In toluene at 0℃; for 6h; | 99% |
benzyl 3,3-difluoro-2-[(4-methoxyphenyl)imino]-5-hexenoate
2-methyl-3-bromo-1-propene
benzyl 3,3-difluoro-2-(4-methoxyphenyl)amino-2-(2-methylallyl)-5-hexenoate
Conditions | Yield |
---|---|
Stage #1: 2-methyl-3-bromo-1-propene With zinc In tetrahydrofuran at 50℃; for 0.666667h; Stage #2: benzyl 3,3-difluoro-2-[(4-methoxyphenyl)imino]-5-hexenoate In tetrahydrofuran at -40℃; for 0.166667h; | 99% |
Stage #1: 2-methyl-3-bromo-1-propene With zinc In tetrahydrofuran at 50℃; for 0.75h; Inert atmosphere; Stage #2: benzyl 3,3-difluoro-2-[(4-methoxyphenyl)imino]-5-hexenoate In tetrahydrofuran at -40℃; Inert atmosphere; chemoselective reaction; | 99% |
Conditions | Yield |
---|---|
With potassium carbonate In water; N,N-dimethyl-formamide | 99% |
The 3-Bromo-2-methylpropene, with the CAS registry number 1458-98-6, is also known as Methylallyl bromide. It belongs to the product categories of Aliphatics; Halides. Its EINECS number is 207-444-6. This chemical's molecular formula is C4H7Br and molecular weight is 135.00. What's more, its systematic name is 3-bromo-2-methylprop-1-ene. It is stable at common pressure and temperature, and it should be sealed and stored in a cool, ventilated and dry place. Moreover, it should be protected from light.
Physical properties of 3-Bromo-2-methylpropene are: (1)ACD/LogP: 2.34; (2)# of Rule of 5 Violations: 0; (3)#H bond acceptors: 0; (4)#H bond donors: 0; (5)#Freely Rotating Bonds: 1; (6)Index of Refraction: 1.455; (7)Molar Refractivity: 27.88 cm3; (8)Molar Volume: 102.6 cm3; (9)Polarizability: 11.05×10-24cm3; (10)Surface Tension: 24.6 dyne/cm; (11)Density: 1.315 g/cm3; (12)Flash Point: 8.4 °C; (13)Enthalpy of Vaporization: 32.19 kJ/mol; (14)Boiling Point: 96.3 °C at 760 mmHg; (15)Vapour Pressure: 50.1 mmHg at 25°C.
Preparation of 3-Bromo-2-methylpropene: this chemical can be prepared by 2-methyl-prop-2-en-1-ol at the temperature of 30 °C. This reaction will need reagent PBr3 with the reaction time of 2 hours. The yield is about 55%.
Uses of 3-Bromo-2-methylpropene: it can be used to produce 4-butyl-2-methyl-oct-1-en-4-ol at the temperature of 50 °C. It will need reagent Mn and solvent ethyl acetate. The yield is about 87%.
When you are using this chemical, please be cautious about it as the following:
This chemical is highly flammable, so you should keep it away from sources of ignition - No smoking. It is harmful by inhalation and if swallowed, and it can cause burns. The substance is toxic to aquatic organisms as it may cause long-term adverse effects in the aquatic environment. You should keep the container in a well-ventilated place and not empty it into drains. In case of accident or if you feel unwell, you must seek medical advice immediately (show the label where possible). You must avoid releasing to the environment just refering to special instructions/safety data sheet.
You can still convert the following datas into molecular structure:
(1)SMILES: BrCC(=C)\C
(2)Std. InChI: InChI=1S/C4H7Br/c1-4(2)3-5/h1,3H2,2H3
(3)Std. InChIKey: USEGQJLHQSTGHW-UHFFFAOYSA-N
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