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13061-96-6

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13061-96-6 Usage

Chemical Properties

White to light yellow crystal powde

Uses

Different sources of media describe the Uses of 13061-96-6 differently. You can refer to the following data:
1. suzuki reaction
2. Methylboronic Acid is a methylated derivative of boronic acid, a building block towards various intermediates in suzuki coupling.
3. Methylboronic acid can be used as a reagent:In the palladium-catalyzed Stille and Suzuki-Miyaura cross-couplings.In the microwave-heated heterogeneous palladium (Pd)-catalytized reactions.In ruthenium (Ru)-catalyzed silylation reactionsTo prepare bis(aminotropone) titanium (Ti) catalysts for ethylene polymerizations.In the enantioselective asymmetric bromoaminocyclization and bromoaminocyclization using amino-thiocarbamate catalysts.To prepare common building blocks for pharmaceuticals and agrochemicals.To prepare chrysin analogs by Suzuki-Miyaura coupling reactions.To prepare casein kinase I inhibitors.In the divergent C-H functionalizations directed by sulfonamide pharmacophores in drug discovery.In the synthesis of unsymmetrical monosulfides from disulfides via copper-catalyzed coupling with boronic acids.In a palladium-catalyzed coupling with enol tosylates.For derivatizing many carbohydrates and biologically active compounds for GLC analysis.

Check Digit Verification of cas no

The CAS Registry Mumber 13061-96-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,3,0,6 and 1 respectively; the second part has 2 digits, 9 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 13061-96:
(7*1)+(6*3)+(5*0)+(4*6)+(3*1)+(2*9)+(1*6)=76
76 % 10 = 6
So 13061-96-6 is a valid CAS Registry Number.
InChI:InChI=1/CH5BO2/c1-2(3)4/h3-4H,1H3

13061-96-6 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
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  • Price
  • Detail
  • TCI America

  • (M1553)  Methylboronic Acid (contains varying amounts of Anhydride)  

  • 13061-96-6

  • 1g

  • 480.00CNY

  • Detail
  • TCI America

  • (M1553)  Methylboronic Acid (contains varying amounts of Anhydride)  

  • 13061-96-6

  • 5g

  • 1,550.00CNY

  • Detail
  • Alfa Aesar

  • (L15589)  Methylboronic acid, 97%   

  • 13061-96-6

  • 1g

  • 289.0CNY

  • Detail
  • Alfa Aesar

  • (L15589)  Methylboronic acid, 97%   

  • 13061-96-6

  • 5g

  • 955.0CNY

  • Detail
  • Aldrich

  • (165336)  Methylboronicacid  97%

  • 13061-96-6

  • 165336-1G

  • 510.12CNY

  • Detail
  • Aldrich

  • (165336)  Methylboronicacid  97%

  • 13061-96-6

  • 165336-5G

  • 1,682.46CNY

  • Detail

13061-96-6SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name Methylboronic acid

1.2 Other means of identification

Product number -
Other names Methylboronic 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:13061-96-6 SDS

13061-96-6Synthetic route

dimethyl sulfide borane
13292-87-0

dimethyl sulfide borane

dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

Conditions
ConditionsYield
With carbon monoxide; water In tetrahydrofuran byproducts: S(CH3)2; a soln. of BH3*S(CH3)2 flushed with CO; a soln. of catalyst added, stirred rapidly and maintained at 25°C for 12-16 h; water added; evapd.;94%
Triisopropyl borate
5419-55-6

Triisopropyl borate

methyllithium
917-54-4

methyllithium

dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

Conditions
ConditionsYield
With hydrogenchloride In diethyl ether byproducts: LiCl, i-propanol; (N2); a soln. of B(O-i-Pr)3 cooled with a dry ice-acetone bath; CH3Li added slowly and stirred for 1 h; allowed to warm to room temp. with stirring for 3 h; cooled to 0°C; a soln. of HCl in ether added and stirred for 0.5 h; decanted; hydrolyzed with water; distd.; dried;79%
methyl magnesium iodide
917-64-6

methyl magnesium iodide

Trimethyl borate
121-43-7

Trimethyl borate

dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

Conditions
ConditionsYield
With diethyl ether Zers. des Reaktionsproduktes durch angesaeuertes Wasser, wobei Verseifung des intermediaer gebildeten Methylborsaeureesters stattfindet;
Trimethyl borate
121-43-7

Trimethyl borate

methylmagnesium bromide
75-16-1

methylmagnesium bromide

dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

Conditions
ConditionsYield
With diethyl ether und anschliessend mit wss.H2SO4;
Trimethyl borate
121-43-7

Trimethyl borate

methylmagnesium iodide

methylmagnesium iodide

A

trimethylborane
593-90-8

trimethylborane

B

dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

Conditions
ConditionsYield
Zers. des entstandenen 'Methylborsaeuredimethylesters' CH3B(OCH3)2 durch angesaeuertes Wasser;
dibromomethylborane
17933-16-3

dibromomethylborane

dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

Conditions
ConditionsYield
With water
With water
2,4,6-Trimethyl-[1,3,5,2,4,6]triazatriborinane
5314-85-2

2,4,6-Trimethyl-[1,3,5,2,4,6]triazatriborinane

dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

Conditions
ConditionsYield
With water at 150℃;
1,2-Dimethylboran
16321-94-1

1,2-Dimethylboran

dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

Conditions
ConditionsYield
With water at 150℃;
hydrogenchloride
7647-01-0

hydrogenchloride

hexamethylborazine
877-07-6

hexamethylborazine

A

dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

B

methylamine hydrochloride
593-51-1

methylamine hydrochloride

Conditions
ConditionsYield
at 100℃; Hydrolysis;
Trimethyl borate
121-43-7

Trimethyl borate

CH3MgCl

CH3MgCl

A

trimethylborane
593-90-8

trimethylborane

B

dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

trimethylborane
593-90-8

trimethylborane

water
7732-18-5

water

A

dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

B

Trimethylboroxine
823-96-1

Trimethylboroxine

C

Dimethylborinsaeure-anhydrid
19163-04-3

Dimethylborinsaeure-anhydrid

Conditions
ConditionsYield
at 320℃;
2,4,6-Trimethyl-[1,3,5,2,4,6]triazatriborinane
5314-85-2

2,4,6-Trimethyl-[1,3,5,2,4,6]triazatriborinane

water
7732-18-5

water

A

dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

B

ammonia
7664-41-7

ammonia

Conditions
ConditionsYield
at 150℃;
hydrogenchloride
7647-01-0

hydrogenchloride

2-methyl-borazine
21127-95-7

2-methyl-borazine

A

dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

B

ammonium chloride

ammonium chloride

C

H3BO3

H3BO3

D

hydrogen

hydrogen

Conditions
ConditionsYield
at 200 - 250℃;
hydrogenchloride
7647-01-0

hydrogenchloride

B-dimethylborazole
23208-27-7

B-dimethylborazole

A

dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

B

ammonium chloride

ammonium chloride

C

H3BO3

H3BO3

D

hydrogen

hydrogen

Conditions
ConditionsYield
at 200 - 250℃;
methyl-borane; compound with borane

methyl-borane; compound with borane

water

water

A

dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

B

H3BO3

H3BO3

dimethyl-borane; compound with methylborane

dimethyl-borane; compound with methylborane

water

water

A

dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

B

dimethylboronynoic acid

dimethylboronynoic acid

C

hydrogen

hydrogen

dimethylsulfoxonium methylide*borane
502622-26-6

dimethylsulfoxonium methylide*borane

water
7732-18-5

water

dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

Conditions
ConditionsYield
In neat (no solvent) holding at room temp. in screw-cap vials, crystn. near the cap; identification by single-crystal X-ray analysis;
methyl magnesium iodide
917-64-6

methyl magnesium iodide

Trimethyl borate
121-43-7

Trimethyl borate

A

trimethylborane
593-90-8

trimethylborane

B

dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

Conditions
ConditionsYield
In diethyl ether
In diethyl ether
methyl diborane
23777-55-1

methyl diborane

A

hydroxy-dimethyl-borane
13061-97-7

hydroxy-dimethyl-borane

B

dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

C

boric acid
11113-50-1

boric acid

Conditions
ConditionsYield
With water byproducts: H2; at room temp.;
With H2O byproducts: H2; at room temp.;
methyl diborane
23777-55-1

methyl diborane

A

dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

B

boric acid
11113-50-1

boric acid

Conditions
ConditionsYield
With water hydrolysis;;
With H2O hydrolysis;;
1.1-dimethyl borane(6)
16924-32-6

1.1-dimethyl borane(6)

A

hydroxy-dimethyl-borane
13061-97-7

hydroxy-dimethyl-borane

B

dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

C

boric acid
11113-50-1

boric acid

Conditions
ConditionsYield
With water byproducts: H2; at room temp.;
With H2O byproducts: H2; at room temp.;

A

hydroxy-dimethyl-borane
13061-97-7

hydroxy-dimethyl-borane

B

dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

C

boric acid
11113-50-1

boric acid

Conditions
ConditionsYield
With water byproducts: H2; at room temp.;
With H2O byproducts: H2; at room temp.;
2-methyl-borazine
21127-95-7

2-methyl-borazine

A

dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

B

ammonia
7664-41-7

ammonia

C

boric acid
11113-50-1

boric acid

Conditions
ConditionsYield
With hydrogenchloride; water byproducts: H2; at 200-250°C for 6 h with 20% aq. HCl;
With H2O; HCl byproducts: H2; at 200-250°C for 6 h with 20% aq. HCl;
tetramethyl diborane
21482-59-7

tetramethyl diborane

A

hydroxy-dimethyl-borane
13061-97-7

hydroxy-dimethyl-borane

B

dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

C

boric acid
11113-50-1

boric acid

Conditions
ConditionsYield
With water byproducts: H2; at room temp.;
With H2O byproducts: H2; at room temp.;
trimethyldiborane(6)
21107-27-7

trimethyldiborane(6)

A

hydroxy-dimethyl-borane
13061-97-7

hydroxy-dimethyl-borane

B

dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

Conditions
ConditionsYield
With water byproducts: H2;
With H2O byproducts: H2;
trimethyldiborane(6)
21107-27-7

trimethyldiborane(6)

A

hydroxy-dimethyl-borane
13061-97-7

hydroxy-dimethyl-borane

B

dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

C

boric acid
11113-50-1

boric acid

Conditions
ConditionsYield
With water byproducts: H2; at room temp.;
With H2O byproducts: H2; at room temp.;
B-dimethylborazole
23208-27-7

B-dimethylborazole

A

dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

B

ammonia
7664-41-7

ammonia

C

boric acid
11113-50-1

boric acid

Conditions
ConditionsYield
With hydrogenchloride; water byproducts: H2; at 200-250°C for 6 h with 20% aq. HCl;
With H2O; HCl byproducts: H2; at 200-250°C for 6 h with 20% aq. HCl;
2,4,6-Trimethyl-[1,3,5,2,4,6]triazatriborinane
5314-85-2

2,4,6-Trimethyl-[1,3,5,2,4,6]triazatriborinane

A

dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

B

ammonia
7664-41-7

ammonia

C

boric acid
11113-50-1

boric acid

Conditions
ConditionsYield
With hydrogenchloride; water byproducts: H2; at 200-250°C for 6 h with 20% aq. HCl;
With H2O; HCl byproducts: H2; at 200-250°C for 6 h with 20% aq. HCl;
N-B,B'-trimethylborazole

N-B,B'-trimethylborazole

A

dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

B

boric acid
11113-50-1

boric acid

Conditions
ConditionsYield
With hydrogenchloride; water byproducts: NH3, CH3NH2, H2; by heating;
With HCl; H2O byproducts: NH3, CH3NH2, H2; by heating;
ethyl 2-(4-fluorophenyl)-6-nitro-5-(trifluoromethylsulfonyloxy)benzofuran-3-carboxylate
691857-51-9

ethyl 2-(4-fluorophenyl)-6-nitro-5-(trifluoromethylsulfonyloxy)benzofuran-3-carboxylate

dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

ethyl 2-(4-fluorophenyl)-5-methyl-6-nitro-1-benzofuran-3-carboxylate
1378428-85-3

ethyl 2-(4-fluorophenyl)-5-methyl-6-nitro-1-benzofuran-3-carboxylate

Conditions
ConditionsYield
With potassium fluoride; sodium bromide; tetrakis(triphenylphosphine) palladium(0) In water; toluene for 25h; Inert atmosphere; Reflux;100%
dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

(S)-3-bromo-2,6-difluoro-N-(thiazol-4-yl)-4-((1-((6-(trifluoromethyl)pyridin-2-yl)methyl)pyrrolidin-3-yl)amino)benzenesulfonamide

(S)-3-bromo-2,6-difluoro-N-(thiazol-4-yl)-4-((1-((6-(trifluoromethyl)pyridin-2-yl)methyl)pyrrolidin-3-yl)amino)benzenesulfonamide

(S)-2,6-difluoro-3-methyl-N-(thiazol-4-yl)-4-((1-((6-(trifluoromethyl)pyridin-2-yl)methyl)pyrrolidin-3-yl)amino)benzenesulfonamide

(S)-2,6-difluoro-3-methyl-N-(thiazol-4-yl)-4-((1-((6-(trifluoromethyl)pyridin-2-yl)methyl)pyrrolidin-3-yl)amino)benzenesulfonamide

Conditions
ConditionsYield
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane for 12h; Inert atmosphere; Reflux;100%
dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

ethyl 9'-(benzyloxy)-10'-bromo-2'-oxo-2',7'-dihydrospiro[cyclohexane-1,6'pyrido[2,1-a]isoquinoline]-3'-carboxylate

ethyl 9'-(benzyloxy)-10'-bromo-2'-oxo-2',7'-dihydrospiro[cyclohexane-1,6'pyrido[2,1-a]isoquinoline]-3'-carboxylate

ethyl 9'-(benzyloxy)-10'-methyl-2'-oxo-2',7'dihydrospiro[cyclohexane-1,6'-pyrido[2,1-a]isoquinoline]-3'-carboxylate

ethyl 9'-(benzyloxy)-10'-methyl-2'-oxo-2',7'dihydrospiro[cyclohexane-1,6'-pyrido[2,1-a]isoquinoline]-3'-carboxylate

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In water; toluene at 85℃; for 6h;100%
dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

tert-butyl ((5-chloro-2-fluoro-4-((6-fluoro-2-((isopropyl(methyl)amino)methyl)-3-methoxybenzyl)amino)phenyl)sulfonyl)(thiazol-4-yl)carbamate

tert-butyl ((5-chloro-2-fluoro-4-((6-fluoro-2-((isopropyl(methyl)amino)methyl)-3-methoxybenzyl)amino)phenyl)sulfonyl)(thiazol-4-yl)carbamate

tert-butyl ((2-fluoro-4-((6-fluoro-2-((isopropyl(methyl)amino)methyl)-3-methoxybenzyl)amino)-5-methylphenyl)sulfonyl)(thiazol-4-yl)carbamate

tert-butyl ((2-fluoro-4-((6-fluoro-2-((isopropyl(methyl)amino)methyl)-3-methoxybenzyl)amino)-5-methylphenyl)sulfonyl)(thiazol-4-yl)carbamate

Conditions
ConditionsYield
Stage #1: dihydroxy-methyl-borane; tert-butyl ((5-chloro-2-fluoro-4-((6-fluoro-2-((isopropyl(methyl)amino)methyl)-3-methoxybenzyl)amino)phenyl)sulfonyl)(thiazol-4-yl)carbamate With potassium phosphate In 1,4-dioxane for 0.333333h; Suzuki-Miyaura Coupling; Inert atmosphere;
Stage #2: With palladium diacetate; tricyclohexylphosphine tetrafluoroborate In 1,4-dioxane at 105℃;
100%
dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

tert-butyl 2-bromo-6-[3-fluoro-2-methoxy-4-(trifluoromethoxy)phenoxy]-3-(trifluoromethyl)benzoate

tert-butyl 2-bromo-6-[3-fluoro-2-methoxy-4-(trifluoromethoxy)phenoxy]-3-(trifluoromethyl)benzoate

tert-butyl 6-[3-fluoro-2-methoxy-4-(trifluoromethoxy)phenoxy]-2-methyl-3-(trifluoromethyl)benzoate

tert-butyl 6-[3-fluoro-2-methoxy-4-(trifluoromethoxy)phenoxy]-2-methyl-3-(trifluoromethyl)benzoate

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In 2-methyltetrahydrofuran at 80℃; for 1h;100%
Stage #1: dihydroxy-methyl-borane; tert-butyl 2-bromo-6-[3-fluoro-2-methoxy-4-(trifluoromethoxy)phenoxy]-3-(trifluoromethyl)benzoate With caesium carbonate In 2-methyltetrahydrofuran for 0.5h; Inert atmosphere;
Stage #2: With (bis-(2-methoxyethyl)amino)sulfur trufluoride In 2-methyltetrahydrofuran at 80℃; for 1h;
100%
dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

(1-bromo-4-hydroxy-7-phenoxyisoquinoline-3-carbonyl)glycine methyl ester

(1-bromo-4-hydroxy-7-phenoxyisoquinoline-3-carbonyl)glycine methyl ester

[(4-hydroxy-1-methyl-7-phenoxy-isoquinoline-3-carbonyl)-amino]-acetic acid

[(4-hydroxy-1-methyl-7-phenoxy-isoquinoline-3-carbonyl)-amino]-acetic acid

Conditions
ConditionsYield
With potassium dihydrogenphosphate; tetrakis(triphenylphosphine) palladium(0) In ethanol; water at 100℃; for 16h; Inert atmosphere;100%
With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate; water In 2-methoxy-ethanol at 110℃; for 4h;91%
dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

C20H28INO2

C20H28INO2

(S)-(3-ethyl-3-pentyl-2,3-dihydrobenzofuran-6-yl)(piperidin-1-yl)methanone

(S)-(3-ethyl-3-pentyl-2,3-dihydrobenzofuran-6-yl)(piperidin-1-yl)methanone

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); (R)-N-((S)-(3,5-di-tert-butyl-4-methoxyphenyl)(2-(dicyclohexylphosphanyl)phenyl)methyl)-N,2-dimethylpropane-2-sulfinamide; potassium hydroxide In toluene at 20 - 85℃; Inert atmosphere; Sealed tube; enantioselective reaction;99.2%
dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

9-chloroanthracene
716-53-0

9-chloroanthracene

9-methylanthracene
779-02-2

9-methylanthracene

Conditions
ConditionsYield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In tetrahydrofuran; toluene at 100℃; for 24h; Suzuki-Miyaura reaction;99%
2-(3-chloro-8-methyl-azulen-5-yl)-propionic acid methyl ester
867380-21-0

2-(3-chloro-8-methyl-azulen-5-yl)-propionic acid methyl ester

dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

2-(3,8-Dimethyl-azulen-5-yl)-propionic acid methyl ester
111415-94-2

2-(3,8-Dimethyl-azulen-5-yl)-propionic acid methyl ester

Conditions
ConditionsYield
With palladium diacetate; potassium phosphate In toluene at 100℃; for 24h;99%
dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

5-(2-aminophenyl)-1H-pyrazole
111562-32-4

5-(2-aminophenyl)-1H-pyrazole

5-methyl-5,6-dihydrobenzo[e]pyrazolo[1,5-c][1,3,2]diazaborinine
1350934-17-6

5-methyl-5,6-dihydrobenzo[e]pyrazolo[1,5-c][1,3,2]diazaborinine

Conditions
ConditionsYield
In toluene for 1h; Inert atmosphere; Dean-Stark; Reflux;99%
In toluene for 1h; Inert atmosphere; Reflux;89%
dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

2-formyl-4,6-dimethylphenyl trifluoromethanesulfonate
1628799-95-0

2-formyl-4,6-dimethylphenyl trifluoromethanesulfonate

2,3,5-trimethylbenzaldehyde
5779-71-5

2,3,5-trimethylbenzaldehyde

Conditions
ConditionsYield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In tetrahydrofuran; water Suzuki Coupling; Reflux;99%
dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

2-formyl-3,6-dimethylphenyl trifluoromethanesulfonate
1403381-95-2

2-formyl-3,6-dimethylphenyl trifluoromethanesulfonate

2,3,6-trimethylbenzaldehyde
34341-29-2

2,3,6-trimethylbenzaldehyde

Conditions
ConditionsYield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In tetrahydrofuran; water Suzuki Coupling; Reflux;99%
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In tetrahydrofuran; water Suzuki Coupling; Enzymatic reaction;93%
dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

N-methyliminodiacetic acid
4408-64-4

N-methyliminodiacetic acid

2,6-dimethyl-1,3,6,2-dioxazaborocane-4,8-dione

2,6-dimethyl-1,3,6,2-dioxazaborocane-4,8-dione

Conditions
ConditionsYield
In acetonitrile at 130℃; under 12929 Torr; for 0.0833333h; Solvent; Microwave irradiation;99%
dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

3-methyl-1-(pyrimidin-2-yl)-1H-indole
1310708-89-4

3-methyl-1-(pyrimidin-2-yl)-1H-indole

2,3-dimethyl-1-(pyrimidin-2-yl)-1H-indole

2,3-dimethyl-1-(pyrimidin-2-yl)-1H-indole

Conditions
ConditionsYield
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver carbonate In neat (no solvent) at 46℃; for 1h; Milling; regioselective reaction;99%
With potassium fluoride; palladium diacetate; silver carbonate; p-benzoquinone In tert-Amyl alcohol at 110℃; for 6h; Sealed tube; regioselective reaction;95%
dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

ethyl 7-bromo-1-methyl-1H-indole-5-carboxylate

ethyl 7-bromo-1-methyl-1H-indole-5-carboxylate

ethyl 1,7-dimethyl-1H-indole-5-carboxylate

ethyl 1,7-dimethyl-1H-indole-5-carboxylate

Conditions
ConditionsYield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In toluene at 100℃; for 3h; Inert atmosphere;99%
dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

(4S,5S)-2-{(1S,3S,4S,5R,6S)-1-chlor-5-(benzyloxy)-3-[(4-methoxybenzyl)oxy]-4,6-dimethyloctyl}-4,5-dicyclohexyl-1,3,2-dioxaborolane

(4S,5S)-2-{(1S,3S,4S,5R,6S)-1-chlor-5-(benzyloxy)-3-[(4-methoxybenzyl)oxy]-4,6-dimethyloctyl}-4,5-dicyclohexyl-1,3,2-dioxaborolane

A

(3S,4S,5R,6S)-5-(benzyloxy)-3-[(4-methoxybenzyl)oxy]-4,6-dimethyloctanal

(3S,4S,5R,6S)-5-(benzyloxy)-3-[(4-methoxybenzyl)oxy]-4,6-dimethyloctanal

Conditions
ConditionsYield
Stage #1: (4S,5S)-2-{(1S,3S,4S,5R,6S)-1-chlor-5-(benzyloxy)-3-[(4-methoxybenzyl)oxy]-4,6-dimethyloctyl}-4,5-dicyclohexyl-1,3,2-dioxaborolane With dihydrogen peroxide; sodium carbonate In tetrahydrofuran; water at 20℃; for 24h;
Stage #2: With Sodium thiosulfate pentahydrate; sodium iodide In tetrahydrofuran; water for 0.5h;
Stage #3: dihydroxy-methyl-borane With magnesium sulfate at 20℃; for 19h;
A 64%
B 99%
dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

(Z)-N'-hydroxy-N-(4-sulfamoylphenyl)benzimidamide

(Z)-N'-hydroxy-N-(4-sulfamoylphenyl)benzimidamide

4-(5-methyl-3-phenyl-1,2,4,5-oxadiazaborol-4(5H)-yl)benzenesulfonamide

4-(5-methyl-3-phenyl-1,2,4,5-oxadiazaborol-4(5H)-yl)benzenesulfonamide

Conditions
ConditionsYield
In toluene at 110℃; for 1h; Molecular sieve; Inert atmosphere; Sealed tube;99%
dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

1,1',1''‐nitrilotris(propan‐2‐one)trioxime
672-92-4

1,1',1''‐nitrilotris(propan‐2‐one)trioxime

benzyl bromide
100-39-0

benzyl bromide

C17H25BN4O3

C17H25BN4O3

Conditions
ConditionsYield
Stage #1: dihydroxy-methyl-borane; 1,1',1''‐nitrilotris(propan‐2‐one)trioxime; benzyl bromide In methanol at 20℃; for 20h;
Stage #2: With lithium carbonate In methanol at 20℃; for 4h;
99%
dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

(R)-3-methyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)butan-1-amine hydrochloride

(R)-3-methyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)butan-1-amine hydrochloride

(R)-(1-amino-3-methylbutyl)boronic acid hydrochloride
1158974-93-6

(R)-(1-amino-3-methylbutyl)boronic acid hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In water; acetone at 20℃;99%
3-carboxyphenylboronic acid pinacol ester
269409-73-6

3-carboxyphenylboronic acid pinacol ester

dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

3-Carboxyphenylboronic acid
25487-66-5

3-Carboxyphenylboronic acid

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane at 20℃;99%
dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)piperidine hydrochloride
1218790-99-8

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)piperidine hydrochloride

piperidin-4-ylboronic acid hydrochloride

piperidin-4-ylboronic acid hydrochloride

Conditions
ConditionsYield
Stage #1: dihydroxy-methyl-borane; 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)piperidine hydrochloride With trifluoroacetic acid In dichloromethane at 20℃;
Stage #2: With hydrogenchloride In water at 20℃;
99%
dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

4-chlorobenzophenone
134-85-0

4-chlorobenzophenone

4-Methylbenzophenone
134-84-9

4-Methylbenzophenone

Conditions
ConditionsYield
With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); 3-(dicyclohexylphosphino)-2-(2,6-dimethoxyphenyl)-1-methyl-1H-indole In 1,4-dioxane at 100℃; for 6h; Suzuki-Miyaura Coupling; Schlenk technique; Sealed tube; Inert atmosphere;99%
dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

C40H27AgBr2N4

C40H27AgBr2N4

3,17-dimethyl-meso-tris(p-tolylcorrolato)silver(III)

3,17-dimethyl-meso-tris(p-tolylcorrolato)silver(III)

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In toluene at 90℃; for 18h; Suzuki Coupling; Inert atmosphere;99%
1-chloro-4-methyl-azulene
867380-15-2

1-chloro-4-methyl-azulene

dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

1,4-dimethylazulene
1127-69-1

1,4-dimethylazulene

Conditions
ConditionsYield
With palladium diacetate; potassium phosphate In toluene at 100℃; for 24h;98%
methyl 3-chloro-4-fluoro-5-methoxybenzoate

methyl 3-chloro-4-fluoro-5-methoxybenzoate

dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

4-fluoro-3-methoxy-5-methylbenzoate

4-fluoro-3-methoxy-5-methylbenzoate

Conditions
ConditionsYield
With potassium phosphate; palladium diacetate; phosphine ligand In tetrahydrofuran; water; toluene at 100℃; for 0.166667h; microwave irradiation;98%
dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

C20H30Br2N2O2S
1446202-04-5

C20H30Br2N2O2S

C22H36N2O2S
1446202-05-6

C22H36N2O2S

Conditions
ConditionsYield
With potassium fluoride; tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at 20℃; for 11h; Reflux; Inert atmosphere;98%
dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

(S)-5-chloro-2-fluoro-4-((1-(pyridin-2-ylmethyl)pyrrolidin-3-yl)amino)-N-(thiazol-4-yl)benzenesulfonamide 2,2,2-trifluoroacetate

(S)-5-chloro-2-fluoro-4-((1-(pyridin-2-ylmethyl)pyrrolidin-3-yl)amino)-N-(thiazol-4-yl)benzenesulfonamide 2,2,2-trifluoroacetate

(S)-2-fluoro-5-methyl-4-((1-(pyridin-2-ylmethyl)pyrrolidin-3-yl)amino)-N-(thiazol-4-yl)benzenesulfonamide

(S)-2-fluoro-5-methyl-4-((1-(pyridin-2-ylmethyl)pyrrolidin-3-yl)amino)-N-(thiazol-4-yl)benzenesulfonamide

Conditions
ConditionsYield
With potassium phosphate; palladium diacetate; tricyclohexylphosphine tetrafluoroborate In 1,4-dioxane for 4h; Inert atmosphere; Reflux;98%
dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

3-aminophenylboronic acid pinacolate
210907-84-9

3-aminophenylboronic acid pinacolate

3-aminophenylboronic acid hydrochloric salt

3-aminophenylboronic acid hydrochloric salt

Conditions
ConditionsYield
Stage #1: dihydroxy-methyl-borane; 3-aminophenylboronic acid pinacolate With trifluoroacetic acid In dichloromethane at 20℃;
Stage #2: With hydrogenchloride In water at 20℃; Reagent/catalyst; Temperature; Solvent;
98%
dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

tert-butyl 2-bromo-6-[2-(trideuteriomethoxy)-4-(trifluoromethoxy)phenoxy]-3-(trifluoromethyl)benzoate

tert-butyl 2-bromo-6-[2-(trideuteriomethoxy)-4-(trifluoromethoxy)phenoxy]-3-(trifluoromethyl)benzoate

tert-butyl 2-methyl-6-[2-(trideuteriomethoxy)-4-(trifluoromethoxy)phenoxy]-3-(trifluoromethyl)benzoate

tert-butyl 2-methyl-6-[2-(trideuteriomethoxy)-4-(trifluoromethoxy)phenoxy]-3-(trifluoromethyl)benzoate

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 120℃; for 0.5h; Inert atmosphere; Sealed tube; Microwave irradiation;98%
dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

methyl 6-(2,6-difluoro-3-(trifluoromethyl-sulfonyloxy)phenyl)-5-fluoropicolinate
1210419-44-5

methyl 6-(2,6-difluoro-3-(trifluoromethyl-sulfonyloxy)phenyl)-5-fluoropicolinate

6-(2,6-difluoro-3-methylphenyl)-5-fluoropicolinic acid
1210419-49-0

6-(2,6-difluoro-3-methylphenyl)-5-fluoropicolinic acid

Conditions
ConditionsYield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 100℃; for 3h; Inert atmosphere;97%

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13061-96-6Relevant articles and documents

Koehler,Hess

, p. 5345,5346 (1974)

FUNCTIONALIZED PRIMARY ALKYLTRIFLUOROBORATE SALTS AND METHOD FOR MAKING THE SAME

-

Paragraph 0100-0102, (2017/03/21)

The invention provides methods for preparing boronic acids, for example, primary alkyl or alkenyl boronic acids, and alkali metal alkyl trifluoro borate salts, as described herein, wherein the primary alkyl boronic acids and the potassium alkyl trifluoroborate salts can contain one or more unprotected functional groups.

Organoboranes. 39. Convenient procedures for the preparation of methylboronic acid and trimethylboroxin

Brown, Herbert C.,Cole, Thomas E.

, p. 816 - 821 (2008/10/08)

Methylboronic acid and its anhydride, trimethylboroxin, were prepared by three routes. The carbonylation of borane-dimethyl sulfide gives in high yields trimethylboroxin, readily hydrated to methylboronic acid. The reaction of methyllithium with selected

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