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14559-88-7

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14559-88-7 Usage

Uses

2,2-Dimethylethenylboronic acid is a useful reagent in the preparation of prostaglandins via 1,4-conjugate addition.

Check Digit Verification of cas no

The CAS Registry Mumber 14559-88-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,4,5,5 and 9 respectively; the second part has 2 digits, 8 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 14559-88:
(7*1)+(6*4)+(5*5)+(4*5)+(3*9)+(2*8)+(1*8)=127
127 % 10 = 7
So 14559-88-7 is a valid CAS Registry Number.
InChI:InChI=1/C4H9BO2/c1-4(2)3-5(6)7/h3,6-7H,1-2H3

14559-88-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name 2,2-Dimethylethenylboronic acid

1.2 Other means of identification

Product number -
Other names 2-methylprop-1-enylboronic acid

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:14559-88-7 SDS

14559-88-7Synthetic route

Triisopropyl borate
5419-55-6

Triisopropyl borate

2-methyl-1-propenylbromide
3017-69-4

2-methyl-1-propenylbromide

water
7732-18-5

water

2,2-dimethylethenylboronic acid
14559-88-7

2,2-dimethylethenylboronic acid

Conditions
ConditionsYield
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
38614-36-7

2-methylpropen-1-ylmagnesium bromide

2,2-dimethylethenylboronic acid
14559-88-7

2,2-dimethylethenylboronic acid

Conditions
ConditionsYield
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
3017-69-4

2-methyl-1-propenylbromide

chloro-bis(dimethylamino)borane
6562-41-0

chloro-bis(dimethylamino)borane

water
7732-18-5

water

2,2-dimethylethenylboronic acid
14559-88-7

2,2-dimethylethenylboronic acid

Conditions
ConditionsYield
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
121-43-7

Trimethyl borate

2-methylprop-1-enyllithium
29917-94-0

2-methylprop-1-enyllithium

2,2-dimethylethenylboronic acid
14559-88-7

2,2-dimethylethenylboronic acid

Conditions
ConditionsYield
und anschliessend mit wss.HCl;
Trimethyl borate
121-43-7

Trimethyl borate

2-methylpropen-1-ylmagnesium bromide
38614-36-7

2-methylpropen-1-ylmagnesium bromide

2,2-dimethylethenylboronic acid
14559-88-7

2,2-dimethylethenylboronic acid

tris(ethylenedioxyboryl)methane
59278-44-3

tris(ethylenedioxyboryl)methane

acetone
67-64-1

acetone

2,2-dimethylethenylboronic acid
14559-88-7

2,2-dimethylethenylboronic acid

Conditions
ConditionsYield
(i) MeLi, Et2O, THF, CH2Cl2, (ii) /BRN= 635680/; Multistep reaction;
Trimethyl borate
121-43-7

Trimethyl borate

2-methyl-propenyl magnesium halide

2-methyl-propenyl magnesium halide

2,2-dimethylethenylboronic acid
14559-88-7

2,2-dimethylethenylboronic acid

Conditions
ConditionsYield
und Erwaermen des Reaktionsprodukts mit wss.H2SO4;
C10H21BO2

C10H21BO2

2,2-dimethylethenylboronic acid
14559-88-7

2,2-dimethylethenylboronic acid

Conditions
ConditionsYield
With water; ammonium chloride In pentane at 20℃; for 0.5h;
C6H13BO2
90011-02-2

C6H13BO2

2,2-dimethylethenylboronic acid
14559-88-7

2,2-dimethylethenylboronic acid

Conditions
ConditionsYield
With hydrogenchloride; water In tetrahydrofuran at 0 - 20℃; for 1.5h;
2,2-dimethylethenylboronic acid
14559-88-7

2,2-dimethylethenylboronic acid

methyl 3-bromo-4-(tetrahydro-2H-pyran-2-yloxy)benzoate
1142224-41-6

methyl 3-bromo-4-(tetrahydro-2H-pyran-2-yloxy)benzoate

methyl 3-(2-methyl-1-propenyl)-4-(tetrahydro-2H-pyran-2-yloxy)benzoate
1142225-87-3

methyl 3-(2-methyl-1-propenyl)-4-(tetrahydro-2H-pyran-2-yloxy)benzoate

Conditions
ConditionsYield
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
14559-88-7

2,2-dimethylethenylboronic acid

(E)-4-(pyrazin-2-yl)but-3-en-2-one
1414846-58-4

(E)-4-(pyrazin-2-yl)but-3-en-2-one

6-methyl-4-(pyrazin-2-yl)hept-5-en-2-one

6-methyl-4-(pyrazin-2-yl)hept-5-en-2-one

Conditions
ConditionsYield
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
14559-88-7

2,2-dimethylethenylboronic acid

(E)-4-(2,4,6-trimethoxyphenyl)but-3-en-2-one
42811-79-0

(E)-4-(2,4,6-trimethoxyphenyl)but-3-en-2-one

6-methyl-4-(2,4,6-trimethoxyphenyl)hept-5-en-2-one

6-methyl-4-(2,4,6-trimethoxyphenyl)hept-5-en-2-one

Conditions
ConditionsYield
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
14559-88-7

2,2-dimethylethenylboronic acid

(E)-4-(2-thienyl)but-3-en-2-one
874-83-9, 33603-63-3

(E)-4-(2-thienyl)but-3-en-2-one

6-methyl-4-(thiophen-2-yl)hept-5-en-2-one

6-methyl-4-(thiophen-2-yl)hept-5-en-2-one

Conditions
ConditionsYield
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
14559-88-7

2,2-dimethylethenylboronic acid

(Z)-7-[(3R)-3-(tert-butyldimethylsilanyloxy)-5-oxo-cyclopent-1-enyl]hept-5-enoic acid isopropyl ester
474944-36-0

(Z)-7-[(3R)-3-(tert-butyldimethylsilanyloxy)-5-oxo-cyclopent-1-enyl]hept-5-enoic acid isopropyl ester

(Z)-7-[(2R,3R)-3-(tert-butyl-dimethylsilanyloxy)-2-(2-methyl-prop-1-enyl)-5-oxo-cyclopentyl]hept-5-enoic acid isopropyl ester

(Z)-7-[(2R,3R)-3-(tert-butyl-dimethylsilanyloxy)-2-(2-methyl-prop-1-enyl)-5-oxo-cyclopentyl]hept-5-enoic acid isopropyl ester

Conditions
ConditionsYield
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
14559-88-7

2,2-dimethylethenylboronic acid

N-(5-chloro[1,2,4]triazolo[1,5-a]pyridin-2-yl)nicotinamide
1124382-78-0

N-(5-chloro[1,2,4]triazolo[1,5-a]pyridin-2-yl)nicotinamide

N-[5-(2-methylprop-1-en-1-yl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]nicotinamide dihydrochloride

N-[5-(2-methylprop-1-en-1-yl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]nicotinamide dihydrochloride

Conditions
ConditionsYield
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
14559-88-7

2,2-dimethylethenylboronic acid

(E)-4-(quinolin-2-yl)but-3-en-2-one
137479-63-1

(E)-4-(quinolin-2-yl)but-3-en-2-one

6-methyl-4-(quinolin-2-yl)hept-5-en-2-one

6-methyl-4-(quinolin-2-yl)hept-5-en-2-one

Conditions
ConditionsYield
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
14559-88-7

2,2-dimethylethenylboronic acid

(E)-4-(1-methyl-1H-imidazol-2-yl)but-3-en-2-one
1414846-63-1

(E)-4-(1-methyl-1H-imidazol-2-yl)but-3-en-2-one

6-methyl-4-(1-methyl-1H-imidazol-2-yl)hept-5-en-2-one

6-methyl-4-(1-methyl-1H-imidazol-2-yl)hept-5-en-2-one

Conditions
ConditionsYield
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
14559-88-7

2,2-dimethylethenylboronic acid

2-(3-bromo-2-methylbenzoylamino)indan-2-carboxylic acid ethyl ester
1092449-74-5

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
1092449-75-6

2-[2-methyl-3-(2-methyl-1-propenyl)benzoylamino]indan-2-carboxylic acid ethyl ester

Conditions
ConditionsYield
With sodium hydrogencarbonate; tetrakis(triphenylphosphine) palladium(0) In water; N,N-dimethyl-formamide at 110℃; for 5h;92%
2,2-dimethylethenylboronic acid
14559-88-7

2,2-dimethylethenylboronic acid

4-(pyridin-4-yl)-3-buten-2-one
94445-75-7

4-(pyridin-4-yl)-3-buten-2-one

6-methyl-4-(pyridin-4-yl)hept-5-en-2-one

6-methyl-4-(pyridin-4-yl)hept-5-en-2-one

Conditions
ConditionsYield
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
14559-88-7

2,2-dimethylethenylboronic acid

(S)-(5-(hydroxymethyl)-1-tosyl-7-(((trifluoromethyl)sulfonyl)oxy)-1,2,3,5-tetrahydrocyclopenta[f]indol-5-yl)methyl benzoate

(S)-(5-(hydroxymethyl)-1-tosyl-7-(((trifluoromethyl)sulfonyl)oxy)-1,2,3,5-tetrahydrocyclopenta[f]indol-5-yl)methyl benzoate

(S)-(5-(hydroxymethyl)-7-(2-methylprop-1-en-1-yl)-1-tosyl-1,2,3,5-tetrahydrocyclopenta[f]indol-5-yl)methyl benzoate

(S)-(5-(hydroxymethyl)-7-(2-methylprop-1-en-1-yl)-1-tosyl-1,2,3,5-tetrahydrocyclopenta[f]indol-5-yl)methyl benzoate

Conditions
ConditionsYield
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
14559-88-7

2,2-dimethylethenylboronic acid

1,1-dimethylethyl 9-bromo-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate
1055880-27-7

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
1055880-88-0

tert-butyl 9-(2-methylpropa-1-ene-1-yl)-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate

Conditions
ConditionsYield
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
14559-88-7

2,2-dimethylethenylboronic acid

(E)-4-pyridin-3-ylbut-3-en-2-one
28447-16-7, 94445-77-9

(E)-4-pyridin-3-ylbut-3-en-2-one

6-methyl-4-(pyridin-3-yl)hept-5-en-2-one

6-methyl-4-(pyridin-3-yl)hept-5-en-2-one

Conditions
ConditionsYield
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
14559-88-7

2,2-dimethylethenylboronic acid

benzo[e][1,2,3]oxathiazine 2,2-dioxide
71730-46-6

benzo[e][1,2,3]oxathiazine 2,2-dioxide

(R)-4-(2-methylprop-1-en-1-yl)-3,4-dihydrobenzo[e][1,2,3]oxathiazine 2,2-dioxide

(R)-4-(2-methylprop-1-en-1-yl)-3,4-dihydrobenzo[e][1,2,3]oxathiazine 2,2-dioxide

Conditions
ConditionsYield
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
1046793-45-6

1-Benzenesulfonyl-5-bromo-3-[2-(1-methyl-piperidin-4-yl)-thiazol-4-yl]-1H pyrrolo[2,3-b]pyridine

2,2-dimethylethenylboronic acid
14559-88-7

2,2-dimethylethenylboronic acid

1-Benzenesulfonyl-3-[2-(1-methyl-piperidin-4-yl)-thiazol-4-yl]-5-(2-methyl-propenyl)-1H-pyrrolo[2,3-b]pyridine

1-Benzenesulfonyl-3-[2-(1-methyl-piperidin-4-yl)-thiazol-4-yl]-5-(2-methyl-propenyl)-1H-pyrrolo[2,3-b]pyridine

Conditions
ConditionsYield
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
1046793-41-2

4-(1-Benzenesulfonyl-5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-thiazole-2-carboxylic acid ethyl ester

2,2-dimethylethenylboronic acid
14559-88-7

2,2-dimethylethenylboronic acid

4-[1-Benzenesulfonyl-5-(2-methyl-propenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-thiazole-2-carboxylic acid ethyl ester

4-[1-Benzenesulfonyl-5-(2-methyl-propenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-thiazole-2-carboxylic acid ethyl ester

Conditions
ConditionsYield
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
14559-88-7

2,2-dimethylethenylboronic acid

indole-2,3-dione
91-56-5

indole-2,3-dione

(S)-3-hydroxy-3-(2-methylprop-1-en-1-yl)indolin-2-one

(S)-3-hydroxy-3-(2-methylprop-1-en-1-yl)indolin-2-one

Conditions
ConditionsYield
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
14559-88-7

2,2-dimethylethenylboronic acid

N-methyl-2-iodoaniline
57056-93-6

N-methyl-2-iodoaniline

N-methyl-N-[2-(2-methylpropenyl)phenyl]amine
41652-76-0

N-methyl-N-[2-(2-methylpropenyl)phenyl]amine

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 80℃; for 12h;80%
2,2-dimethylethenylboronic acid
14559-88-7

2,2-dimethylethenylboronic acid

tert-butyl 2-[3-acetyl-5-bromo-7-(prop-2-en-1-yl)indazol-1-yl]acetate

tert-butyl 2-[3-acetyl-5-bromo-7-(prop-2-en-1-yl)indazol-1-yl]acetate

tert-butyl 2-(3-acetyl-7-allyl-5-(2-methylprop-1-en-1-yl)-1H-indazol-1-yl)acetate

tert-butyl 2-(3-acetyl-7-allyl-5-(2-methylprop-1-en-1-yl)-1H-indazol-1-yl)acetate

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 90℃; for 16h; Inert atmosphere;79.9%
2,2-dimethylethenylboronic acid
14559-88-7

2,2-dimethylethenylboronic acid

(3S,8aR)-5-oxo-1,2,3,5,8,8a-hexahydroindolizine-3-carboxylic acid methyl ester

(3S,8aR)-5-oxo-1,2,3,5,8,8a-hexahydroindolizine-3-carboxylic acid methyl ester

(3S,8aR)-6-(2-methylprop-1-en-1-yl)-5-oxo-1,2,3,5,8,8a-hexahydroindolizine-3-carboxy methyl ester

(3S,8aR)-6-(2-methylprop-1-en-1-yl)-5-oxo-1,2,3,5,8,8a-hexahydroindolizine-3-carboxy methyl ester

Conditions
ConditionsYield
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
14559-88-7

2,2-dimethylethenylboronic acid

2-(2-iodo-3-methyl-benzoylamino)-indane-2-carboxylic acid ethyl ester
1092447-82-9

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
1092447-84-1

2-[3-methyl-2-(2-methyl-propenyl)-benzoylamino]-indan-2-carboxylic acid ethyl ester

Conditions
ConditionsYield
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
14559-88-7

2,2-dimethylethenylboronic acid

anthranilic acid amide
28144-70-9

anthranilic acid amide

2-(2-methylprop-1-en-1-yl)-2,3-dihydrobenzo[d][1,3,2]diazaborinin-4(1H)-one

2-(2-methylprop-1-en-1-yl)-2,3-dihydrobenzo[d][1,3,2]diazaborinin-4(1H)-one

Conditions
ConditionsYield
With dibromobis(triphenylphosphine)nickel(II); triethylamine; palladium dichloride In ethanol at 20℃; for 2h; Green chemistry; chemoselective reaction;75%
2,2-dimethylethenylboronic acid
14559-88-7

2,2-dimethylethenylboronic acid

methyl (3S,9aS)-6-bromo-5-oxo-2,3,5,8,9,9a-hexahydro-1H-pyrrolo[1,2-a]azepine-3-carboxylate

methyl (3S,9aS)-6-bromo-5-oxo-2,3,5,8,9,9a-hexahydro-1H-pyrrolo[1,2-a]azepine-3-carboxylate

(3S,9aS)-6-(2-methylprop-1-en-1-yl)-5-oxo-2,3,5,8,9,9a-hexahydro-1H-pyrrolo[1,2-a]azepine-3-carboxylic acid methyl ster

(3S,9aS)-6-(2-methylprop-1-en-1-yl)-5-oxo-2,3,5,8,9,9a-hexahydro-1H-pyrrolo[1,2-a]azepine-3-carboxylic acid methyl ster

Conditions
ConditionsYield
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
14559-88-7

2,2-dimethylethenylboronic acid

tris(2-methylpropene-1-yl) boroxine
1010113-27-5

tris(2-methylpropene-1-yl) boroxine

Conditions
ConditionsYield
With magnesium sulfite In pyridine; diethyl ether at 20℃;73%
byproducts: H2O; dehydration;;
byproducts: H2O; dehydration;;
2,2-dimethylethenylboronic acid
14559-88-7

2,2-dimethylethenylboronic acid

5-fluoro-2-(2-iodo-3-methyl-benzoylamino)indan-2-carboxylic acid ethyl ester
1092446-64-4

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
1092447-88-5

5-fluoro-2-[3-methyl-2-(2-methyl-propenyl)-benzoylamino]-indan-2-carboxylic acid ethyl ester

Conditions
ConditionsYield
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
14559-88-7

2,2-dimethylethenylboronic acid

5,5-bis(hydroxymethyl)-1-tosyl-1,2,3,5-tetrahydrocyclopenta[f]indol-7-yl trifluormethansulfonate

5,5-bis(hydroxymethyl)-1-tosyl-1,2,3,5-tetrahydrocyclopenta[f]indol-7-yl trifluormethansulfonate

(7-(2-methylprop-1-en-1-yl)-1-tosyl-1,2,3,5-tetrahydrocyclopenta[f]indole-5,5-diyl)dimethanol

(7-(2-methylprop-1-en-1-yl)-1-tosyl-1,2,3,5-tetrahydrocyclopenta[f]indole-5,5-diyl)dimethanol

Conditions
ConditionsYield
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
14559-88-7

2,2-dimethylethenylboronic acid

3-methyl-3-phenylcyclopropene
65051-83-4

3-methyl-3-phenylcyclopropene

((1S,2R)-1-methyl-2-(2-methylprop-1-en-1-yl)cyclopropyl)benzene

((1S,2R)-1-methyl-2-(2-methylprop-1-en-1-yl)cyclopropyl)benzene

Conditions
ConditionsYield
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%
2,2-dimethylethenylboronic acid
14559-88-7

2,2-dimethylethenylboronic acid

C10H11BrN2O2

C10H11BrN2O2

C14H18N2O2

C14H18N2O2

Conditions
ConditionsYield
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
14559-88-7

2,2-dimethylethenylboronic acid

1-(4-bromo-2-chloro-phenyl)-1-cyclopropyl-2-(1,2,4-triazol-1-yl)ethanol
1615663-83-6

1-(4-bromo-2-chloro-phenyl)-1-cyclopropyl-2-(1,2,4-triazol-1-yl)ethanol

1-(2-chloro-4-(2-methylprop-1-en-1-yl)phenyl)-1-cyclopropyl-2-(1H-1,2,4-triazol-1-yl)ethan-1-ol

1-(2-chloro-4-(2-methylprop-1-en-1-yl)phenyl)-1-cyclopropyl-2-(1H-1,2,4-triazol-1-yl)ethan-1-ol

Conditions
ConditionsYield
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
923584-14-9

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
14559-88-7

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
923584-06-9

1-Benzenesulfonyl-5-(2-methyl-propenyl)-3-[1-(2-morpholin-4-yl-ethyl)-1H-pyrazol-4-yl]-1H-pyrrolo[2,3-b]pyridine

Conditions
ConditionsYield
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%

14559-88-7Relevant articles and documents

-

Letsinger,Skoog

, p. 895 (1953)

-

Preparation of 2,2-dimethyl-vinyl boric acid method

-

Paragraph 0025, (2017/01/12)

The invention belongs to the technical field of chemical industry, and in particular discloses a method for preparing 2,2-dimethyl vinyl boric acid. The method is characterized by comprising the steps of enabling an organic solvent 1 and 3,3-dimethyl acrylic acid to react with bromine for 3-4 hours at 10-60 DEG C, adjusting the pH value to 9-10 by using alkali after reaction, reacting for 2-3 hours at 30-60 DEG C, standing for layering after reaction, and distilling an organic layer to obtain 2,2-dimethyl vinyl bromine; enabling an organic solvent 2 to react with 2,2-dimethyl vinyl bromine for 2-3 hours at minus 78 to minus 40 DEG C under the action of lithium and a boronizing agent, adjusting the pH value to 3-4 by using hydrochloric acid, performing extraction by using acetic ether, concentrating an organic layer, pulping and filtering through a non-polar hydrocarbon solvent, and drying to obtain 2,2-dimethyl vinyl boric acid. The method disclosed by the invention has the characteristics of safety, environment friendliness and easiness in operation, and is suitable for industrial production.

Enantioselective conjugate addition of alkenylboronic acids to indole-appended enones

Lundy, Brian J.,Jansone-Popova, Santa,May, Jeremy A.

supporting information; experimental part, p. 4958 - 4961 (2011/11/29)

An enantioselective addition of alkenylboronic acids and alkynylboronic esters to unprotected indole-appended enones is reported. This transformation proceeds with high enantioselectivity and high product yields via the use of catalytic amounts of 3,3′-bis(pentafluorophenyl)-BINOL and Mg(Ot-Bu) 2. A range of α-branched indole derivatives are available from the transformation.

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