13061-96-6

Basic information

• Product Name: Methylboronic acid
• Synonyms: METHYLBORON DIHYDROXIDE;METHYLBORONIC ACID;METHANEBORONIC ACID;CH5BO2;dihydroxy-methyl-borane;METHYLBORONIC ACID FOR GC;METHANDROSTENOLONE;Methylboron dihydroxide, GLC Grade
• CAS NO: 13061-96-6
• Molecular Formula: CH₅BO₂
• Molecular Weight: 59.86
• EINECS: 629-203-8
• Product Categories: Substituted Boronic Acids;API intermediates;Boronic acid;Organoborons;CHIRAL CHEMICALS;Alkyl;Piperidines ,Piperazines ,Homopiperidines
• Mol File: 13061-96-6.mol
• Article Data: 5

Chemical Properties

• Melting Point: 91-94 °C(lit.)
• Boiling Point: 141.745 °C at 760 mmHg
• Flash Point: 39.526 °C
• Appearance: White to off-white/Crystalline Powder
• Density: 0.965 g/cm³
• Vapor Pressure: 2.35mmHg at 25°C
• Refractive Index: 1.345
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Solubility: DMSO, Water
• PKA: 9.97±0.43(Predicted)
• Water Solubility: Soluble in water.
• Sensitive: Hygroscopic
• BRN: 1731087
• CAS DataBase Reference: Methylboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Methylboronic acid(13061-96-6)
• EPA Substance Registry System: Methylboronic acid(13061-96-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 3-10
• HazardClass: IRRITANT
• Hazardous Substances Data: 13061-96-6(Hazardous Substances Data)

Usage

Description

Methylboronic acid, also known as methylboronic acid, is a methylated derivative of boronic acid. It is a white to light yellow crystal powder and serves as a building block for various intermediates in Suzuki coupling reactions. Methylboronic acid is known for its versatile applications in different industries, particularly in the field of organic chemistry.

Uses

Used in Chemical Synthesis:
Methylboronic acid is used as a reagent for various chemical reactions, including:
1. Palladium-catalyzed Stille and Suzuki-Miyaura cross-couplings.
2. Microwave-heated heterogeneous palladium (Pd)-catalyzed reactions.
3. Ruthenium (Ru)-catalyzed silylation reactions.
4. Preparation of bis(aminotropone) titanium (Ti) catalysts for ethylene polymerizations.
5. Enantioselective asymmetric bromoaminocyclization and bromoaminocyclization using amino-thiocarbamate catalysts.
6. Preparation of common building blocks for pharmaceuticals and agrochemicals.
7. Preparation of chrysin analogs by Suzuki-Miyaura coupling reactions.
8. Preparation of casein kinase I inhibitors.
9. Divergent C-H functionalizations directed by sulfonamide pharmacophores in drug discovery.
10. Synthesis of unsymmetrical monosulfides from disulfides via copper-catalyzed coupling with boronic acids.
11. Palladium-catalyzed coupling with enol tosylates.
12. Derivatizing many carbohydrates and biologically active compounds for GLC analysis.
These applications highlight the importance of methylboronic acid in the synthesis of various compounds and its role in advancing the field of organic chemistry.

InChI:InChI=1/CH5BO2/c1-2(3)4/h3-4H,1H3

Synthetic route

dimethyl sulfide borane (13292-87-0) → dihydroxy-methyl-borane (13061-96-6)

Conditions	Yield
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) + methyllithium (917-54-4) → dihydroxy-methyl-borane (13061-96-6)

Conditions	Yield
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) + Trimethyl borate (121-43-7) → dihydroxy-methyl-borane (13061-96-6)

Conditions	Yield
With diethyl ether Zers. des Reaktionsproduktes durch angesaeuertes Wasser, wobei Verseifung des intermediaer gebildeten Methylborsaeureesters stattfindet;

Trimethyl borate (121-43-7) + methylmagnesium bromide (75-16-1) → dihydroxy-methyl-borane (13061-96-6)

Conditions	Yield
With diethyl ether und anschliessend mit wss.H2SO4;

Trimethyl borate (121-43-7) + methylmagnesium iodide → trimethylborane (593-90-8) + dihydroxy-methyl-borane (13061-96-6)

Conditions	Yield
Zers. des entstandenen 'Methylborsaeuredimethylesters' CH3B(OCH3)2 durch angesaeuertes Wasser;

dibromomethylborane (17933-16-3) → dihydroxy-methyl-borane (13061-96-6)

Conditions	Yield
With water
With water

2,4,6-Trimethyl-[1,3,5,2,4,6]triazatriborinane (5314-85-2) → dihydroxy-methyl-borane (13061-96-6)

Conditions	Yield
With water at 150℃;

1,2-Dimethylboran (16321-94-1) → dihydroxy-methyl-borane (13061-96-6)

Conditions	Yield
With water at 150℃;

hydrogenchloride (7647-01-0) + hexamethylborazine (877-07-6) → dihydroxy-methyl-borane (13061-96-6) + methylamine hydrochloride (593-51-1)

Conditions	Yield
at 100℃; Hydrolysis;

Trimethyl borate (121-43-7) + CH3MgCl → trimethylborane (593-90-8) + dihydroxy-methyl-borane (13061-96-6)

trimethylborane (593-90-8) + water (7732-18-5) → dihydroxy-methyl-borane (13061-96-6) + Trimethylboroxine (823-96-1) + Dimethylborinsaeure-anhydrid (19163-04-3)

Conditions	Yield
at 320℃;

2,4,6-Trimethyl-[1,3,5,2,4,6]triazatriborinane (5314-85-2) + water (7732-18-5) → dihydroxy-methyl-borane (13061-96-6) + ammonia (7664-41-7)

Conditions	Yield
at 150℃;

hydrogenchloride (7647-01-0) + 2-methyl-borazine (21127-95-7) → dihydroxy-methyl-borane (13061-96-6) + ammonium chloride + H3BO3 + hydrogen

Conditions	Yield
at 200 - 250℃;

hydrogenchloride (7647-01-0) + B-dimethylborazole (23208-27-7) → dihydroxy-methyl-borane (13061-96-6) + ammonium chloride + H3BO3 + hydrogen

Conditions	Yield
at 200 - 250℃;

methyl-borane; compound with borane + water → dihydroxy-methyl-borane (13061-96-6) + H3BO3

dimethyl-borane; compound with methylborane + water → dihydroxy-methyl-borane (13061-96-6) + dimethylboronynoic acid + hydrogen

dimethylsulfoxonium methylide*borane (502622-26-6) + water (7732-18-5) → dihydroxy-methyl-borane (13061-96-6)

Conditions	Yield
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) + Trimethyl borate (121-43-7) → trimethylborane (593-90-8) + dihydroxy-methyl-borane (13061-96-6)

Conditions	Yield
In diethyl ether
In diethyl ether

methyl diborane (23777-55-1) → hydroxy-dimethyl-borane (13061-97-7) + dihydroxy-methyl-borane (13061-96-6) + boric acid (11113-50-1)

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

methyl diborane (23777-55-1) → dihydroxy-methyl-borane (13061-96-6) + boric acid (11113-50-1)

Conditions	Yield
With water hydrolysis;;
With H2O hydrolysis;;

1.1-dimethyl borane(6) (16924-32-6) → hydroxy-dimethyl-borane (13061-97-7) + dihydroxy-methyl-borane (13061-96-6) + boric acid (11113-50-1)

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

dimethyldiborane (20436-23-1, 17156-88-6, 6808-37-3) → hydroxy-dimethyl-borane (13061-97-7) + dihydroxy-methyl-borane (13061-96-6) + boric acid (11113-50-1)

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

2-methyl-borazine (21127-95-7) → dihydroxy-methyl-borane (13061-96-6) + ammonia (7664-41-7) + boric acid (11113-50-1)

Conditions	Yield
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) → hydroxy-dimethyl-borane (13061-97-7) + dihydroxy-methyl-borane (13061-96-6) + boric acid (11113-50-1)

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

trimethyldiborane(6) (21107-27-7) → hydroxy-dimethyl-borane (13061-97-7) + dihydroxy-methyl-borane (13061-96-6)

Conditions	Yield
With water byproducts: H2;
With H2O byproducts: H2;

trimethyldiborane(6) (21107-27-7) → hydroxy-dimethyl-borane (13061-97-7) + dihydroxy-methyl-borane (13061-96-6) + boric acid (11113-50-1)

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

B-dimethylborazole (23208-27-7) → dihydroxy-methyl-borane (13061-96-6) + ammonia (7664-41-7) + boric acid (11113-50-1)

Conditions	Yield
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) → dihydroxy-methyl-borane (13061-96-6) + ammonia (7664-41-7) + boric acid (11113-50-1)

Conditions	Yield
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 → dihydroxy-methyl-borane (13061-96-6) + boric acid (11113-50-1)

Conditions	Yield
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) + dihydroxy-methyl-borane (13061-96-6) → ethyl 2-(4-fluorophenyl)-5-methyl-6-nitro-1-benzofuran-3-carboxylate (1378428-85-3)

Conditions	Yield
With potassium fluoride; sodium bromide; tetrakis(triphenylphosphine) palladium(0) In water; toluene for 25h; Inert atmosphere; Reflux;	100%

dihydroxy-methyl-borane (13061-96-6) + (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

Conditions	Yield
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane for 12h; Inert atmosphere; Reflux;	100%

dihydroxy-methyl-borane (13061-96-6) + 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

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In water; toluene at 85℃; for 6h;	100%

dihydroxy-methyl-borane (13061-96-6) + 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

Conditions	Yield
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) + 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

Conditions	Yield
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) + (1-bromo-4-hydroxy-7-phenoxyisoquinoline-3-carbonyl)glycine methyl ester → [(4-hydroxy-1-methyl-7-phenoxy-isoquinoline-3-carbonyl)-amino]-acetic acid

Conditions	Yield
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) + C20H28INO2 → (S)-(3-ethyl-3-pentyl-2,3-dihydrobenzofuran-6-yl)(piperidin-1-yl)methanone

Conditions	Yield
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) + 9-chloroanthracene (716-53-0) → 9-methylanthracene (779-02-2)

Conditions	Yield
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) + dihydroxy-methyl-borane (13061-96-6) → 2-(3,8-Dimethyl-azulen-5-yl)-propionic acid methyl ester (111415-94-2)

Conditions	Yield
With palladium diacetate; potassium phosphate In toluene at 100℃; for 24h;	99%

dihydroxy-methyl-borane (13061-96-6) + 5-(2-aminophenyl)-1H-pyrazole (111562-32-4) → 5-methyl-5,6-dihydrobenzo[e]pyrazolo[1,5-c][1,3,2]diazaborinine (1350934-17-6)

Conditions	Yield
In toluene for 1h; Inert atmosphere; Dean-Stark; Reflux;	99%
In toluene for 1h; Inert atmosphere; Reflux;	89%

dihydroxy-methyl-borane (13061-96-6) + 2-formyl-4,6-dimethylphenyl trifluoromethanesulfonate (1628799-95-0) → 2,3,5-trimethylbenzaldehyde (5779-71-5)

Conditions	Yield
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) + 2-formyl-3,6-dimethylphenyl trifluoromethanesulfonate (1403381-95-2) → 2,3,6-trimethylbenzaldehyde (34341-29-2)

Conditions	Yield
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) + N-methyliminodiacetic acid (4408-64-4) → 2,6-dimethyl-1,3,6,2-dioxazaborocane-4,8-dione

Conditions	Yield
In acetonitrile at 130℃; under 12929 Torr; for 0.0833333h; Solvent; Microwave irradiation;	99%

dihydroxy-methyl-borane (13061-96-6) + 3-methyl-1-(pyrimidin-2-yl)-1H-indole (1310708-89-4) → 2,3-dimethyl-1-(pyrimidin-2-yl)-1H-indole

Conditions	Yield
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) + ethyl 7-bromo-1-methyl-1H-indole-5-carboxylate → ethyl 1,7-dimethyl-1H-indole-5-carboxylate

Conditions	Yield
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) + (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 → (3S,4S,5R,6S)-5-(benzyloxy)-3-[(4-methoxybenzyl)oxy]-4,6-dimethyloctanal + 159701-90-3

Conditions	Yield
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) + (Z)-N'-hydroxy-N-(4-sulfamoylphenyl)benzimidamide → 4-(5-methyl-3-phenyl-1,2,4,5-oxadiazaborol-4(5H)-yl)benzenesulfonamide

Conditions	Yield
In toluene at 110℃; for 1h; Molecular sieve; Inert atmosphere; Sealed tube;	99%

dihydroxy-methyl-borane (13061-96-6) + 1,1',1''‐nitrilotris(propan‐2‐one)trioxime (672-92-4) + benzyl bromide (100-39-0) → C17H25BN4O3

Conditions	Yield
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) + (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)

Conditions	Yield
With hydrogenchloride In water; acetone at 20℃;	99%

3-carboxyphenylboronic acid pinacol ester (269409-73-6) + dihydroxy-methyl-borane (13061-96-6) → 3-Carboxyphenylboronic acid (25487-66-5)

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 20℃;	99%

dihydroxy-methyl-borane (13061-96-6) + 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)piperidine hydrochloride (1218790-99-8) → piperidin-4-ylboronic acid hydrochloride

Conditions	Yield
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) + 4-chlorobenzophenone (134-85-0) → 4-Methylbenzophenone (134-84-9)

Conditions	Yield
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) + C40H27AgBr2N4 → 3,17-dimethyl-meso-tris(p-tolylcorrolato)silver(III)

Conditions	Yield
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) + dihydroxy-methyl-borane (13061-96-6) → 1,4-dimethylazulene (1127-69-1)

Conditions	Yield
With palladium diacetate; potassium phosphate In toluene at 100℃; for 24h;	98%

methyl 3-chloro-4-fluoro-5-methoxybenzoate + dihydroxy-methyl-borane (13061-96-6) → 4-fluoro-3-methoxy-5-methylbenzoate

Conditions	Yield
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) + C20H30Br2N2O2S (1446202-04-5) → C22H36N2O2S (1446202-05-6)

Conditions	Yield
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) + (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

Conditions	Yield
With potassium phosphate; palladium diacetate; tricyclohexylphosphine tetrafluoroborate In 1,4-dioxane for 4h; Inert atmosphere; Reflux;	98%

dihydroxy-methyl-borane (13061-96-6) + 3-aminophenylboronic acid pinacolate (210907-84-9) → 3-aminophenylboronic acid hydrochloric salt

Conditions	Yield
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) + 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

Conditions	Yield
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) + methyl 6-(2,6-difluoro-3-(trifluoromethyl-sulfonyloxy)phenyl)-5-fluoropicolinate (1210419-44-5) → 6-(2,6-difluoro-3-methylphenyl)-5-fluoropicolinic acid (1210419-49-0)

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

Upstream product

• 762-73-2 trimethyl(allyl)stannane 
• 10294-33-4 boron tribromide 
• 41453-13-8 2,3,4,5-tetramethyl-1,3,4,2,5-selenadiazadiborolidine 
• 22871-83-6 N-trimethyl-B-trigermylborazine 
• 22871-82-5 B-Bis--B.N-tetramethyl-borazol 
• 22871-81-4 B-Germyl-B_.N-pentamethyl-borazol 
• 7647-01-0 hydrogenchloride 
• 877-07-6 hexamethylborazine 
• 16321-94-1 1,2-Dimethylboran 
• 5314-85-2 2,4,6-Trimethyl-[1,3,5,2,4,6]triazatriborinane 
• 17933-16-3 dibromomethylborane 
• 121-43-7 Trimethyl borate 
• 75-16-1 methylmagnesium bromide 
• 917-64-6 methyl magnesium iodide 

Downstream Products

• 857054-02-5 3-methyl-2H-furo[2,3-c]pyran-2-one 
• 941696-36-2 2-(2-chloro-4-methoxyphenyl)-5-(1-ethylpropyl)-3, 7-dimethylpyrazolo[1,5-a]pyridine 
• 1035688-95-9 2-(3-fluoro-3'-(trifluoromethoxy)biphenyl-4-ylamino)-5-methylnicotinic acid 
• 65169-43-9 2-chloro-5-methylnicotinic acid methyl ester 
• 67-56-1 methanol 
• 7318-81-2 bis(methoxy)methylborane 
• 107-31-3 Methyl formate 
• 1021531-55-4 C₃₂H₃₂F₃N₅O₃ 
• 1021531-54-3 N-[3-(1,7-dimethyl-2-oxo-1,2-dihydro-[1,6]naphthyridin-3-yl)-4-methyl-phenyl]-3-piperazin-1-yl-5-trifluoromethyl-benzamide 
• 1020332-66-4 tert-butyl 4-(1-(3-(5-(trifluoromethyl)pyridin-2-yloxy)phenyl)ethylidene)piperidine-1-carboxylate 
• 1067187-89-6 5-methyl-7-(trifluoromethyl)indoline-2,3-dione 
• 391-12-8 7-trifluoromethylisatin 
• 181957-07-3 ((C₆H₅)2PC₅H₄)Fe(C₅H₃(P(C₆H₅)2)CH(CH₃)NC₆H₄OBCH₃) 
• 278172-59-1 methyltriphenylbismuthonium tetrafluoroborate 

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Relevant articles and documents

FUNCTIONALIZED PRIMARY ALKYLTRIFLUOROBORATE SALTS AND METHOD FOR MAKING THE SAME

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

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