Triisopropyl borate
2-methyl-1-propenylbromide
water
2,2-dimethylethenylboronic acid
Conditions | Yield |
---|---|
Stage #1: Triisopropyl borate; 2-methyl-1-propenylbromide With lithium In tetrahydrofuran at -50 - -40℃; Inert atmosphere; Stage #2: water With hydrogenchloride In tetrahydrofuran at 0 - 10℃; pH=3 - 4; Temperature; Reagent/catalyst; Inert atmosphere; | 60.3% |
2-methylpropen-1-ylmagnesium bromide
2,2-dimethylethenylboronic acid
Conditions | Yield |
---|---|
With Trimethyl borate; lithium chloride In tetrahydrofuran; diethyl ether at -78 - 20℃; Inert atmosphere; | 55% |
With Trimethyl borate In diethyl ether at -78 - 20℃; | 41% |
Stage #1: 2-methylpropen-1-ylmagnesium bromide With Trimethyl borate In tetrahydrofuran at -78 - 20℃; Inert atmosphere; Stage #2: With hydrogenchloride; water In tetrahydrofuran at 0 - 20℃; for 1.5h; Inert atmosphere; | |
Stage #1: 2-methylpropen-1-ylmagnesium bromide With Trimethyl borate In tetrahydrofuran at -70 - 20℃; for 3.58333h; Inert atmosphere; Stage #2: With N-methyliminodiacetic acid In tetrahydrofuran; dimethyl sulfoxide at 120 - 150℃; for 1h; Inert atmosphere; Stage #3: With water; sodium hydroxide In tetrahydrofuran at 20℃; for 0.25h; |
2-methyl-1-propenylbromide
chloro-bis(dimethylamino)borane
water
2,2-dimethylethenylboronic acid
Conditions | Yield |
---|---|
Stage #1: 2-methyl-1-propenylbromide; chloro-bis(dimethylamino)borane With lithium In tetrahydrofuran at -78 - -70℃; Inert atmosphere; Stage #2: water With hydrogenchloride In tetrahydrofuran at 0 - 10℃; pH=3 - 4; Inert atmosphere; | 46.9% |
Trimethyl borate
2-methylprop-1-enyllithium
2,2-dimethylethenylboronic acid
Conditions | Yield |
---|---|
und anschliessend mit wss.HCl; |
Trimethyl borate
2-methylpropen-1-ylmagnesium bromide
2,2-dimethylethenylboronic acid
tris(ethylenedioxyboryl)methane
acetone
2,2-dimethylethenylboronic acid
Conditions | Yield |
---|---|
(i) MeLi, Et2O, THF, CH2Cl2, (ii) /BRN= 635680/; Multistep reaction; |
Trimethyl borate
2,2-dimethylethenylboronic acid
Conditions | Yield |
---|---|
und Erwaermen des Reaktionsprodukts mit wss.H2SO4; |
2,2-dimethylethenylboronic acid
Conditions | Yield |
---|---|
With water; ammonium chloride In pentane at 20℃; for 0.5h; |
C6H13BO2
2,2-dimethylethenylboronic acid
Conditions | Yield |
---|---|
With hydrogenchloride; water In tetrahydrofuran at 0 - 20℃; for 1.5h; |
2,2-dimethylethenylboronic acid
methyl 3-bromo-4-(tetrahydro-2H-pyran-2-yloxy)benzoate
methyl 3-(2-methyl-1-propenyl)-4-(tetrahydro-2H-pyran-2-yloxy)benzoate
Conditions | Yield |
---|---|
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In water; N,N-dimethyl-formamide at 70℃; for 23h; Inert atmosphere; | 100% |
With potassium phosphate; 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl; palladium diacetate In water; N,N-dimethyl-formamide at 70℃; for 23h; Suzuki Coupling; Inert atmosphere; | 100% |
2,2-dimethylethenylboronic acid
(E)-4-(pyrazin-2-yl)but-3-en-2-one
Conditions | Yield |
---|---|
With (R)-3,3’-bis(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)-1,1’-binaphthyl-2,2’-diol; magnesium 2-methylpropan-2-olate In toluene at 70℃; for 8h; Molecular sieve; Inert atmosphere; enantioselective reaction; | 99% |
2,2-dimethylethenylboronic acid
(E)-4-(2,4,6-trimethoxyphenyl)but-3-en-2-one
Conditions | Yield |
---|---|
With (R)-3,3’-bis(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)-1,1’-binaphthyl-2,2’-diol; magnesium 2-methylpropan-2-olate In toluene at 115℃; for 1h; Molecular sieve; Inert atmosphere; enantioselective reaction; | 99% |
2,2-dimethylethenylboronic acid
(E)-4-(2-thienyl)but-3-en-2-one
Conditions | Yield |
---|---|
With (R)-3,3’-bis(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)-1,1’-binaphthyl-2,2’-diol; magnesium 2-methylpropan-2-olate In toluene at 115℃; for 2h; Molecular sieve; Inert atmosphere; enantioselective reaction; | 99% |
2,2-dimethylethenylboronic acid
(Z)-7-[(3R)-3-(tert-butyldimethylsilanyloxy)-5-oxo-cyclopent-1-enyl]hept-5-enoic acid isopropyl ester
Conditions | Yield |
---|---|
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; potassium hydroxide In methanol; water at 3℃; for 72h; Temperature; Inert atmosphere; diastereoselective reaction; | 99% |
2,2-dimethylethenylboronic acid
N-(5-chloro[1,2,4]triazolo[1,5-a]pyridin-2-yl)nicotinamide
Conditions | Yield |
---|---|
Stage #1: 2,2-dimethylethenylboronic acid; N-(5-chloro[1,2,4]triazolo[1,5-a]pyridin-2-yl)nicotinamide With cesium fluoride; bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran; water at 120℃; Suzuki-Miyaura reaction; Stage #2: With hydrogenchloride In diethyl ether; dichloromethane | 96% |
2,2-dimethylethenylboronic acid
(E)-4-(quinolin-2-yl)but-3-en-2-one
Conditions | Yield |
---|---|
With (R)-3,3’-bis(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)-1,1’-binaphthyl-2,2’-diol; magnesium 2-methylpropan-2-olate In toluene at 70℃; for 5h; Molecular sieve; Inert atmosphere; enantioselective reaction; | 96% |
2,2-dimethylethenylboronic acid
(E)-4-(1-methyl-1H-imidazol-2-yl)but-3-en-2-one
Conditions | Yield |
---|---|
With (R)-3,3’-bis(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)-1,1’-binaphthyl-2,2’-diol; magnesium 2-methylpropan-2-olate In toluene at 115℃; for 12h; Molecular sieve; Inert atmosphere; enantioselective reaction; | 94% |
2,2-dimethylethenylboronic acid
2-(3-bromo-2-methylbenzoylamino)indan-2-carboxylic acid ethyl ester
2-[2-methyl-3-(2-methyl-1-propenyl)benzoylamino]indan-2-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
With sodium hydrogencarbonate; tetrakis(triphenylphosphine) palladium(0) In water; N,N-dimethyl-formamide at 110℃; for 5h; | 92% |
2,2-dimethylethenylboronic acid
4-(pyridin-4-yl)-3-buten-2-one
Conditions | Yield |
---|---|
With (R)-3,3’-bis(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)-1,1’-binaphthyl-2,2’-diol; magnesium 2-methylpropan-2-olate In toluene at 115℃; for 22h; Molecular sieve; Inert atmosphere; enantioselective reaction; | 91% |
2,2-dimethylethenylboronic acid
Conditions | Yield |
---|---|
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate In water; toluene at 50℃; for 6h; Inert atmosphere; Darkness; | 90% |
2,2-dimethylethenylboronic acid
1,1-dimethylethyl 9-bromo-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate
tert-butyl 9-(2-methylpropa-1-ene-1-yl)-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate
Conditions | Yield |
---|---|
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water at 85℃; for 12h; Inert atmosphere; Saturated solution; | 89.1% |
2,2-dimethylethenylboronic acid
(E)-4-pyridin-3-ylbut-3-en-2-one
Conditions | Yield |
---|---|
With (1R,3'r)-3,3'-bis(perfluorophenyl)[1,1'-binaphthalene]-2,2'-diol; magnesium 2-methylpropan-2-olate In toluene at 115℃; for 15h; Molecular sieve; Inert atmosphere; enantioselective reaction; | 88% |
2,2-dimethylethenylboronic acid
benzo[e][1,2,3]oxathiazine 2,2-dioxide
Conditions | Yield |
---|---|
With nickel(II) perchlorate hexahydrate; C30H28NOP In 2,2,2-trifluoroethanol at 70℃; for 48h; | 87% |
With (1R,1’R,2S,2’S)-2,2’-di-tert-butyl-2,3,2’,3’-tetrahydro-1H,1‘H-(1,1‘)biisophosphindolyl; potassium carbonate; cobalt(II) bromide In tetrahydrofuran at 70℃; for 24h; Inert atmosphere; enantioselective reaction; | 70% |
1-Benzenesulfonyl-5-bromo-3-[2-(1-methyl-piperidin-4-yl)-thiazol-4-yl]-1H pyrrolo[2,3-b]pyridine
2,2-dimethylethenylboronic acid
Conditions | Yield |
---|---|
With sodium carbonate; lithium chloride; bis-triphenylphosphine-palladium(II) chloride In ethanol; water; toluene Suzuki-Miaura reaction; Heating / reflux; | 86% |
With sodium carbonate; lithium chloride; bis-triphenylphosphine-palladium(II) chloride In ethanol; water; toluene at 110℃; for 1.5h; Suzuki Coupling; | 86% |
4-(1-Benzenesulfonyl-5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-thiazole-2-carboxylic acid ethyl ester
2,2-dimethylethenylboronic acid
Conditions | Yield |
---|---|
With sodium carbonate; lithium chloride; bis-triphenylphosphine-palladium(II) chloride In ethanol; water; toluene at 110℃; for 1.5h; Suzuki-Miaura reaction; Heating / reflux; | 85% |
With sodium carbonate; lithium chloride; bis-triphenylphosphine-palladium(II) chloride In ethanol; water; toluene at 110℃; for 1.5h; Suzuki Coupling; | 85% |
2,2-dimethylethenylboronic acid
indole-2,3-dione
Conditions | Yield |
---|---|
With (1R,1’R,2S,2’S)-2,2’-di-tert-butyl-2,3,2’,3’-tetrahydro-1H,1‘H-(1,1‘)biisophosphindolyl; potassium carbonate; cobalt(II) bromide In tetrahydrofuran at 70℃; for 40h; Inert atmosphere; enantioselective reaction; | 80% |
2,2-dimethylethenylboronic acid
N-methyl-2-iodoaniline
N-methyl-N-[2-(2-methylpropenyl)phenyl]amine
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 80℃; for 12h; | 80% |
2,2-dimethylethenylboronic acid
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 90℃; for 16h; Inert atmosphere; | 79.9% |
2,2-dimethylethenylboronic acid
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In 1,4-dioxane; water at 100℃; for 12h; Sealed tube; Inert atmosphere; | 78.1% |
2,2-dimethylethenylboronic acid
2-(2-iodo-3-methyl-benzoylamino)-indane-2-carboxylic acid ethyl ester
2-[3-methyl-2-(2-methyl-propenyl)-benzoylamino]-indan-2-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
With caesium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane; water at 110℃; for 2h; Microwave irradiation; | 78% |
2,2-dimethylethenylboronic acid
anthranilic acid amide
Conditions | Yield |
---|---|
With dibromobis(triphenylphosphine)nickel(II); triethylamine; palladium dichloride In ethanol at 20℃; for 2h; Green chemistry; chemoselective reaction; | 75% |
2,2-dimethylethenylboronic acid
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In 1,4-dioxane; water at 100℃; for 12h; Sealed tube; Inert atmosphere; | 74.6% |
2,2-dimethylethenylboronic acid
tris(2-methylpropene-1-yl) boroxine
Conditions | Yield |
---|---|
With magnesium sulfite In pyridine; diethyl ether at 20℃; | 73% |
byproducts: H2O; dehydration;; | |
byproducts: H2O; dehydration;; |
2,2-dimethylethenylboronic acid
5-fluoro-2-(2-iodo-3-methyl-benzoylamino)indan-2-carboxylic acid ethyl ester
5-fluoro-2-[3-methyl-2-(2-methyl-propenyl)-benzoylamino]-indan-2-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
With potassium carbonate; palladium anchored homogeneous catalyst, FibreCatPd(0) (4.84percentPd) In 1,4-dioxane; ethanol; water at 120℃; for 7h; Microwave irradiation; | 73% |
2,2-dimethylethenylboronic acid
Conditions | Yield |
---|---|
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate In water; toluene at 50℃; for 6h; Suzuki-Miyaura Coupling; Sonication; Darkness; | 71% |
2,2-dimethylethenylboronic acid
3-methyl-3-phenylcyclopropene
Conditions | Yield |
---|---|
With potassium carbonate; cobalt(II) chloride; [2R-[1(2'R*,5'R*),2a,5b]]-1,1'-(1,2-phenylene)bis[2,5-dimethylphospholane] In tetrahydrofuran at 70℃; for 12h; Inert atmosphere; Sealed tube; stereoselective reaction; | 70% |
Conditions | Yield |
---|---|
With palladium diacetate; cesium fluoride; tris-(o-tolyl)phosphine In 1,4-dioxane at 75℃; for 20h; Temperature; Solvent; Inert atmosphere; | 68.2% |
2,2-dimethylethenylboronic acid
1-(4-bromo-2-chloro-phenyl)-1-cyclopropyl-2-(1,2,4-triazol-1-yl)ethanol
Conditions | Yield |
---|---|
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water at 90℃; for 14h; | 67% |
4-(2-(4-(5-bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-pyrazol-1-yl)ethyl)morpholine
2,2-dimethylethenylboronic acid
1-Benzenesulfonyl-5-(2-methyl-propenyl)-3-[1-(2-morpholin-4-yl-ethyl)-1H-pyrazol-4-yl]-1H-pyrrolo[2,3-b]pyridine
Conditions | Yield |
---|---|
With sodium carbonate; lithium chloride; bis-triphenylphosphine-palladium(II) chloride In ethanol; water; toluene for 3h; Suzuki-Miaura reaction; Heating / reflux; | 66% |
With sodium carbonate; lithium chloride; bis-triphenylphosphine-palladium(II) chloride In ethanol; water; toluene at 115℃; for 3h; Suzuki Coupling; | 66% |
The Boronic acid,B-(2-methyl-1-propen-1-yl)-, with the CAS registry number 14559-88-7, is also known as 2,2-Dimethylethenylboronic acid. It belongs to the product category of Boronic Acids. This chemical's molecular formula is C4H9BO2 and molecular weight is 99.92. Its IUPAC name is called 2-methylprop-1-enylboronic acid.
Physical properties of Boronic acid,B-(2-methyl-1-propen-1-yl)-: (1)ACD/LogP: 1.51; (2)ACD/LogD (pH 5.5): 1.51; (3)ACD/LogD (pH 7.4): 1.51; (4)ACD/BCF (pH 5.5): 8.29; (5)ACD/BCF (pH 7.4): 8.26; (6)ACD/KOC (pH 5.5): 158.18; (7)ACD/KOC (pH 7.4): 157.59; (8)#H bond acceptors: 2; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 3; (11)Index of Refraction: 1.427; (12)Molar Refractivity: 26.97 cm3; (13)Molar Volume: 104.9 cm3; (14)Surface Tension: 29.7 dyne/cm; (15)Density: 0.952 g/cm3; (16)Flash Point: 69.1 °C; (17)Enthalpy of Vaporization: 49.67 kJ/mol; (18)Boiling Point: 190.6 °C at 760 mmHg; (19)Vapour Pressure: 0.145 mmHg at 25°C.
You can still convert the following datas into molecular structure:
(1)Canonical SMILES: B(C=C(C)C)(O)O
(2)InChI: InChI=1S/C4H9BO2/c1-4(2)3-5(6)7/h3,6-7H,1-2H3
(3)InChIKey: FWJRSOGVYOIVOC-UHFFFAOYSA-N
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