Conditions | Yield |
---|---|
With phosphorus tribromide at 0℃; for 30h; | 95% |
With ziconium(IV) oxychloride octahydrate; sodium bromide In ethanol; water at 90℃; for 0.166667h; | 90% |
With phosphorus tribromide | 87% |
Conditions | Yield |
---|---|
With hydrogen bromide at 0℃; for 0.5h; | 90% |
With phosphorus tribromide at -20℃; | 68% |
With pyridine; phosphorus tribromide In hexane at 0 - 20℃; | 45% |
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 1h; | 80% |
Conditions | Yield |
---|---|
With pyridine; phosphorus tribromide; sodium chloride In water | 80% |
Conditions | Yield |
---|---|
With silica gel; phosphorus tribromide In dichloromethane at -10℃; for 0.416667h; | 70% |
With hydrogen bromide In acetic acid at 0℃; | 64% |
With hydrogen bromide In acetic acid at 4℃; for 48h; | 64% |
Conditions | Yield |
---|---|
With sodium acetate In water; acetic acid for 3h; | A 5.6% B 5.1% C 4.8% |
hydrogen bromide
isoprene
A
1,3-dibromo-3-methylbutane
B
prenyl bromide
hydrogen bromide
acetic acid
isoprene
A
1,3-dibromo-3-methylbutane
B
prenyl bromide
Conditions | Yield |
---|---|
at -15℃; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 91 percent / LiAlH4 / tetrahydrofuran / 0 - 20 °C 2: 83 percent / HBr / CH2Cl2 / 1.5 h / 0 °C View Scheme | |
Multi-step reaction with 2 steps 1: diisobutylaluminium hydride / diethyl ether / Inert atmosphere 2: phosphorus tribromide / tetrahydrofuran / Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1: diisobutylaluminium hydride / tetrahydrofuran / 3 h / -78 °C 2: phosphorus tribromide / dichloromethane / 1 h / 0 °C View Scheme | |
Multi-step reaction with 2 steps 1: diisobutylaluminium hydride / tetrahydrofuran / 4 h / -78 °C 2: phosphorus tribromide / diethyl ether / 0 °C / Darkness; Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / diethyl ether / 3 h / 0 °C / Inert atmosphere 2: hydrogen bromide / dichloromethane / 2 h / 0 °C / Inert atmosphere; Darkness View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: LiAlH4 / diethyl ether 2: 48percent HBr, conc. H2SO4 View Scheme |
prenyl bromide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 70 percent / AlH3 / tetrahydrofuran / 2 h / 0 °C 2: 40 percent / hexabromoacetone, Ph3P / tetrahydrothiophene 1,1-dioxide View Scheme |
phenyl prenyl ether
prenyl bromide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 2: hydrogen bromide / dann Umsetzung des erhaltenen 2-Brom-2-methyl-butens-(3) View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: lithium alanate; diethyl ether 2: pyridine; petroleum ether; phosphorus (III)-bromide View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sodium hydride / tetrahydrofuran / 0 - 20 °C 2: diisobutylaluminium hydride / tetrahydrofuran; hexane / 3 h / -78 °C 3: phosphorus tribromide / dichloromethane / 1 h / 0 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: diisobutylaluminium hydride / tetrahydrofuran; hexane / 3 h / -78 °C 2: phosphorus tribromide / dichloromethane / 1 h / 0 °C View Scheme |
3,4-dimethylpent-2-en-1-ol
prenyl bromide
Conditions | Yield |
---|---|
With phosphorus tribromide In dichloromethane at 0℃; for 1h; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: methanol; sodium tetrahydroborate / 0.5 h / 0 °C 2: phosphorus tribromide / diethyl ether / 16 h / 0 - 20 °C View Scheme |
Conditions | Yield |
---|---|
at 170℃; | 100% |
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 1h; Williamson Ether Synthesis; Darkness; Inert atmosphere; | 97% |
With sodium hydroxide In N-methyl-acetamide; water | 75% |
ethyl 3-oxo-3-phenylpropionate
prenyl bromide
ethyl 2-benzoyl-5-methylhex-4-enoate
Conditions | Yield |
---|---|
Stage #1: ethyl 3-oxo-3-phenylpropionate With sodium hydride In tetrahydrofuran; mineral oil for 1h; Stage #2: prenyl bromide In tetrahydrofuran; mineral oil at 40℃; | 100% |
Stage #1: ethyl 3-oxo-3-phenylpropionate With sodium hydride In tetrahydrofuran; mineral oil for 1h; Stage #2: prenyl bromide In tetrahydrofuran; mineral oil Heating; | 99% |
Stage #1: ethyl 3-oxo-3-phenylpropionate With sodium hydride In tetrahydrofuran at 0℃; for 0.333333h; Stage #2: prenyl bromide In tetrahydrofuran at 0 - 20℃; | 95% |
acetoacetic acid methyl ester
prenyl bromide
methyl 7-methyl-3-oxooct-6-enoate
Conditions | Yield |
---|---|
Stage #1: acetoacetic acid methyl ester With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.166667h; Stage #2: With n-butyllithium In tetrahydrofuran; mineral oil for 0.166667h; Stage #3: prenyl bromide In tetrahydrofuran; mineral oil for 0.0833333h; | 100% |
With n-butyllithium; sodium hydride In tetrahydrofuran at 0 - 20℃; | 100% |
With n-butyllithium; sodium hydride In tetrahydrofuran at 0℃; | 79% |
triphenylphosphine
prenyl bromide
(3-methylbut-2-enyl)triphenylphosphonium bromide
Conditions | Yield |
---|---|
In toluene at 110℃; Inert atmosphere; | 100% |
In benzene at 20℃; for 20h; | 96% |
In toluene Ambient temperature; | 93% |
benzenesulfonic acid,3-hydroxyphenyl ester
prenyl bromide
resorcinol monoprenyl ether monobenzenesulfonate
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 4h; Heating; | 100% |
3-bromo-4-methoxy-phenol
prenyl bromide
2-Bromo-1-methoxy-4-(3-methyl-but-2-enyloxy)-benzene
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 23℃; for 12h; | 100% |
F-hexyl-1 fluoro-2 ethanol
prenyl bromide
3-Oxa-1-fluoro-2-tridecafluorohexyl-6-methylhept-5-ene
Conditions | Yield |
---|---|
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In diethyl ether at 40℃; for 24h; | 100% |
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In diethyl ether at 40℃; for 24h; | 87% |
potassium ethyl xanthogenate
prenyl bromide
S-(3-methyl-2-buten-1-yl) O-ethyl dithiocarbonate
Conditions | Yield |
---|---|
In acetone for 1h; | 100% |
F-octyl-1 fluoro-2 ethanol
prenyl bromide
Conditions | Yield |
---|---|
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In diethyl ether at 40℃; for 24h; | 100% |
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In diethyl ether at 40℃; for 24h; | 82% |
prenyl bromide
ethyl 2-acetyl-2,5-dimethylhex-4-enoate
Conditions | Yield |
---|---|
In ethanol for 12h; Ambient temperature; | 100% |
Demethoxyfumitremorgin C
prenyl bromide
C26H31N3O2
Conditions | Yield |
---|---|
With sodium hydride 1.) DMF, 45 min, r.t. 2.) r.t., 1 h; | 100% |
N,N'-bis-Boc-S-methyl-isothiourea
prenyl bromide
N,N'-bis(tert-butoxycarbonyl)-N-(γ,γ-dimethylallyl)-S-methylisothiourea
Conditions | Yield |
---|---|
With potassium hydroxide; tetrabutylammomium bromide In dichloromethane; water at 20℃; for 4h; | 100% |
Stage #1: N,N'-bis-Boc-S-methyl-isothiourea With potassium hydroxide; tetrabutylammomium bromide In dichloromethane; acetonitrile at 20℃; for 0.25h; Stage #2: prenyl bromide In dichloromethane; acetonitrile at 20℃; for 7h; | 100% |
Stage #1: N,N'-bis-Boc-S-methyl-isothiourea With potassium hydroxide; tetrabutylammomium bromide In dichloromethane; acetonitrile for 0.25h; Stage #2: prenyl bromide In dichloromethane; acetonitrile for 1h; Stage #3: at 20℃; for 6h; | 100% |
Conditions | Yield |
---|---|
Stage #1: salicylaldehyde With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #2: prenyl bromide In N,N-dimethyl-formamide at 20℃; for 20h; | 100% |
Stage #1: salicylaldehyde With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.333333h; Stage #2: prenyl bromide In N,N-dimethyl-formamide at 0 - 20℃; for 12h; | 99% |
With potassium carbonate In N,N-dimethyl-formamide at 20℃; | 95% |
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 18h; Inert atmosphere; Schlenk technique; | 100% |
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 18h; Inert atmosphere; | 100% |
With sodium hydrogencarbonate In N,N-dimethyl-formamide for 20h; Ambient temperature; | |
With potassium carbonate In acetone |
prenyl bromide
Conditions | Yield |
---|---|
With sodium carbonate; potassium iodide In N,N-dimethyl-formamide for 22h; | 100% |
prenyl bromide
Conditions | Yield |
---|---|
With sodium carbonate; potassium iodide In N,N-dimethyl-formamide for 22h; | 100% |
4-bromo-phenol
prenyl bromide
1-bromo-4-((3-methylbut-2-en-1-yl)oxy)benzene
Conditions | Yield |
---|---|
With potassium carbonate; potassium iodide In acetone at 80℃; for 12h; | 100% |
With potassium carbonate In acetone at 67℃; for 18h; Inert atmosphere; | 98% |
With potassium carbonate; potassium iodide In acetone for 15h; Heating; | 91% |
2,4-dibromo-6-tert-butylphenol
prenyl bromide
1,5-Dibromo-3-tert-butyl-2-(3-methyl-but-2-enyloxy)-benzene
Conditions | Yield |
---|---|
With tetra-(n-butyl)ammonium iodide; potassium carbonate In ethanol for 48h; Ambient temperature; | 100% |
4-Bromo-3-nitrotoluene
prenyl bromide
2-(3-methylbut-2-enyl)-5-methylnitrobenzene
Conditions | Yield |
---|---|
Stage #1: 4-Bromo-3-nitrotoluene With phenyllithium In tetrahydrofuran at -78℃; for 0.0833333h; Stage #2: prenyl bromide With N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at -78℃; for 3h; | 100% |
Stage #1: 4-Bromo-3-nitrotoluene With phenyllithium In tetrahydrofuran at -78℃; Stage #2: prenyl bromide With N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at -78℃; for 3h; | 100% |
2-nitrophenyl bromide
prenyl bromide
1-(3-methylbut-2-en-1-yl)-2-nitrobenzene
Conditions | Yield |
---|---|
Stage #1: 2-nitrophenyl bromide With phenyllithium In tetrahydrofuran at -78℃; for 0.0833333h; Stage #2: prenyl bromide With N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at -78℃; for 3h; | 100% |
Stage #1: 2-nitrophenyl bromide With phenyllithium In tetrahydrofuran at -78℃; Stage #2: prenyl bromide With N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at -78℃; for 3h; | 100% |
3-bromo-4-nitrotoluene
prenyl bromide
2-(3-methylbut-2-enyl)-4-methylnitrobenzene
Conditions | Yield |
---|---|
Stage #1: 3-bromo-4-nitrotoluene With phenyllithium In tetrahydrofuran at -78℃; for 0.0833333h; Stage #2: prenyl bromide With N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at -78℃; for 3h; | 100% |
Stage #1: 3-bromo-4-nitrotoluene With phenyllithium In tetrahydrofuran at -78℃; Stage #2: prenyl bromide With N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at -78℃; for 3h; | 100% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 16h; | 100% |
In ice-water; N,N-dimethyl-formamide | |
With potassium carbonate In N,N-dimethyl-formamide | |
In N-methyl-acetamide; water |
Conditions | Yield |
---|---|
n-Bu4 In ethanol | 100% |
Conditions | Yield |
---|---|
With sodium iodide In tetrahydrofuran; water; mineral oil | 100% |
O-tert-butyldimethylsilyl-N-(p-toluenesulfonyl)homoserine methyl ester
prenyl bromide
O-tert-butyldimethylsilyl-N-(3-methylbut-2-enyl)-N-(p-toluenesulfonyl)homoserine methyl ester
Conditions | Yield |
---|---|
Stage #1: O-tert-butyldimethylsilyl-N-(p-toluenesulfonyl)homoserine methyl ester With caesium carbonate In acetonitrile at 20℃; for 0.5h; Stage #2: prenyl bromide In acetonitrile at 20℃; | 100% |
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 3h; Reflux; | 100% |
With potassium carbonate In acetone Reflux; | 92% |
With potassium carbonate In acetone Inert atmosphere; |
2-hydroxy-5-(p-chlorophenylazo)benzaldehyde
prenyl bromide
C18H17ClN2O2
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; | 100% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; | 100% |
6-bromoisatin
prenyl bromide
6-bromo-1-(3-methylbut-2-en-1-yl)indoline-2,3-dione
Conditions | Yield |
---|---|
Stage #1: 6-bromoisatin With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.166667h; Inert atmosphere; Stage #2: prenyl bromide In N,N-dimethyl-formamide; mineral oil at 0 - 25℃; for 2h; Inert atmosphere; | 100% |
Stage #1: 6-bromoisatin With caesium carbonate In N,N-dimethyl-formamide at 20 - 25℃; for 0.5h; Inert atmosphere; Stage #2: prenyl bromide In N,N-dimethyl-formamide for 16h; Inert atmosphere; | 88% |
Stage #1: 6-bromoisatin With sodium hydride In N,N-dimethyl-formamide; paraffin oil at 0℃; for 1h; Inert atmosphere; Stage #2: prenyl bromide In N,N-dimethyl-formamide; paraffin oil for 70h; Inert atmosphere; | 83% |
prenyl bromide
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In acetonitrile at 0 - 20℃; Inert atmosphere; | 100% |
The 3,3-Dimethylallylbromide with CAS registry number of 870-63-3 is also known as 2-Butene, 1-bromo-3-methyl. The IUPAC name is 1-Bromo-3-methylbut-2-ene. Its EINECS registry number is 212-799-5. In addition, the formula is C5H9Br and the molecular weight is 149.03. This chemical is a light brown liquid with strong pungent odor and should be sealed in cool, dark place with argon.
Physical properties about 3,3-Dimethylallylbromide are: (1)ACD/LogP: 2.86; (2)ACD/LogD (pH 5.5): 2.86; (3)ACD/LogD (pH 7.4): 2.86; (4)ACD/BCF (pH 5.5): 88.49; (5)ACD/BCF (pH 7.4): 88.49; (6)ACD/KOC (pH 5.5): 861.39; (7)ACD/KOC (pH 7.4): 861.39; (8)#Freely Rotating Bonds: 1; (9)Index of Refraction: 1.47; (10)Molar Refractivity: 32.84 cm3; (11)Molar Volume: 117.6 cm3; (12)Surface Tension: 26.3 dyne/cm; (13)Density: 1.266 g/cm3; (14)Flash Point: 32.8 °C; (15)Enthalpy of Vaporization: 35.49 kJ/mol; (16)Boiling Point: 132.6 °C at 760 mmHg; (17)Vapour Pressure: 10.8 mmHg at 25 °C.
Preparation of 3,3-Dimethylallylbromide: it is prepared by reaction of 2-methyl-buta-1,3-diene. The reaction needs reagent HBr and solvent acetic acid at the temperature of 4 °C for 2 days. The yield is about 64%.
Uses of 3,3-Dimethylallylbromide: it is used to produce 1,3-diprenyloxy-4,6-diacetylbenzol by reaction with 4,6-diacetyl-resorcinol. The reaction occurs with reagent K2CO3 and solvent acetone with other condition of heating for 3 hours. The yield is about 99%.
When you are using this chemical, please be cautious about it. As a chemical, it is highly flammable and can cause burns. Besides, it is harmful by inhalation, in contact with skin and if swallowed. During using it, wear suitable protective clothing, gloves and eye/face protection. keep away from sources of ignition. If contact with eyes accidently, rinse immediately with plenty of water and seek medical advice. In case of accident or if you feel unwell seek medical advice immediately.
You can still convert the following datas into molecular structure:
1. Canonical SMILES: CC(=CCBr)C
2. InChI: InChI=1S/C5H9Br/c1-5(2)3-4-6/h3H,4H2,1-2H3
3. InChIKey: LOYZVRIHVZEDMW-UHFFFAOYSA-N
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