5419-55-6

Basic information

• Product Name: Triisopropyl borate
• Synonyms: Isopropyl borate, ((C3H7O)3B);Triisopropoxyboron;triisopropylorthoborate;trisisopropoxyborane;Boric acid triisopropyl ester~Isopropyl borate;Isop;Triisopropyl borate, (Boric acid triisopropyl ester;Triisorpopyl borate
• CAS NO: 5419-55-6
• Molecular Formula: C₉H₂₁BO₃
• Molecular Weight: 188.07
• EINECS: 226-529-9
• Product Categories: B (Classes of Boron Compounds);Boric Acid Esters;Boric Acid Triesters;borate ester;Fine Chemicals;Fine Chemical;Halogenated Heterocycles ,Pyrans
• Mol File: 5419-55-6.mol
• Article Data: 19

Chemical Properties

• Melting Point: -59 °C
• Boiling Point: 140 °C
• Flash Point: 62.6 °F
• Appearance: Clear colorless/Liquid
• Density: 0.815 g/mL at 25 °C(lit.)
• Vapor Pressure: 76 mm Hg ( 75 °C)
• Refractive Index: n20/D 1.376(lit.)
• Storage Temp.: Flammables area
• Solubility: Miscible with ether, ethanol, isopropanol and benzene.
• Water Solubility: decomposes
• Sensitive: Moisture Sensitive
• BRN: 1701469
• CAS DataBase Reference: Triisopropyl borate(CAS DataBase Reference)
• NIST Chemistry Reference: Triisopropyl borate(5419-55-6)
• EPA Substance Registry System: Triisopropyl borate(5419-55-6)

Safety Data

• Hazard Codes: F,Xi
• Statements: 11
• Safety Statements: 7-16-23-24/25-33-9
• RIDADR: UN 2616 3/PG 2
• WGK Germany: 2
• RTECS: ED5950000
• F: 10-21
• TSCA: T
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 5419-55-6(Hazardous Substances Data)

Usage

Chemical Properties

clear colourless liquid

Uses

Triisopropyl borate is used as reagent in Pd-catalyzed coupling reaction with aryl halides such as Suzuki reaction. It is used as a reagent for the preparation of the boronic acids and esters; as a Lewis acid catalyst and involved in the ortho-borylation of 1-substituted naphthalenes. Furthermore, it plays an important role as a catalyst for the production of resins, waxes, paints and varnishes.

General Description

A colorless liquid. Flash point 93°F. Less dense than water and insoluble in water. Vapors heavier than air. Used to make other chemicals.

Air & Water Reactions

Highly flammable. Insoluble in water.

Reactivity Profile

Borates, such as Triisopropyl borate, behave similarly to esters in that they react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters/borates with alkali metals and hydrides.

Health Hazard

May cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.

Fire Hazard

HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.

InChI:InChI=1/C9H21BO3/c1-7(2)11-10(12-8(3)4)13-9(5)6/h7-9H,1-6H3

Synthetic route

zirconium(IV) borohydride + isopropyl alcohol (67-63-0) → Triisopropyl borate (5419-55-6) + zirconium isopropoxide

Conditions	Yield
In pentane byproducts: H2; (Ar (N2) or vac.); dropwise addn. of excess of i-PrOH to Zr-complex in pentane with stirring (60 min, room temp.); concn., sepn. by filtration, a) pptn. drying (vac.), b) distn. of filtrate gives B compd.; elem. anal.;	A 75% B 90%

triisopropoxyboroxin (10298-87-0) + isopropyl alcohol (67-63-0) → Triisopropyl borate (5419-55-6)

Conditions	Yield
With calcium hydride In cyclohexane byproducts: H2; react. under N2, slow addn. of the alcohol to the trialkoxyboroxine and CaH2 in cyclohexane, cooling in a water bath, rapid gas evolution, stirring for 1 h at room temp., heating to 80-90°C overnight; distn. of the product under reduced pressure;	88%

hafnium borohydride + isopropyl alcohol (67-63-0) → Triisopropyl borate (5419-55-6) + hafnium(IV) isopropoxide isopropanolate

Conditions	Yield
In pentane byproducts: H2; (Ar (N2) or vac.); dropwise addn. of excess of i-PrOH to Hf-complex in pentane with stirring (60 min, room temp.); concn., filtration, drying (vac.); elem. anal.;	A n/a B 88%

boric acid (11113-50-1) + isopropyl alcohol (67-63-0) → Triisopropyl borate (5419-55-6)

Conditions	Yield
With calcium hydride In neat (no solvent) byproducts: H2; react. under N2, slow addn. of the alcohol via syringe to B(OH)3 (ratio 3:1) and CaH2, cooling in a water bath, slow heating to 80 - 90°C for 12 h after abating the H2 gas evolution; distn. of the volatile products under reduced pressure (distn. pot temp. <= 120°C);	87%
With calcium hydride at 90℃; Inert atmosphere; Schlenk technique;	66%
In benzene for 18h; Heating;	48%

U(BH4)3(OCH(CH3)2)(C4H8O)2 → Triisopropyl borate (5419-55-6) + U(BH4)2(OCH(CH3)2)2(C4H8O)2

Conditions	Yield
With acetone In tetrahydrofuran addn. of acetone via microsyringe to U complex soln.; standing at room temp., 1h; reducing volume; addn. of pentane; cooling to -78°C; pptn.; rapid filtration, drying (vac.); evapn. of mother liquor, extn. in pentane: B compd.;	A n/a B 81%

1-[Amino(diisopropylamino)boryl]-2-[bis(diisopropylamino)boryl]-2-isopropenyl-1-isopropylhydrazin (80493-41-0) + isopropyl alcohol (67-63-0) → Triisopropyl borate (5419-55-6)

Conditions	Yield
byproducts: i-Pr2NH, i-PrNHNC(CH3)2, NH3; acidimetric determined, chromd.;	70%

2,3,4-Tris(2,6-dimethylpiperidino)-1,3,4,6,7,8,9,9a-octahydro-6,9a-dimethyl-2H-pyrido[1,2-e][1,3,5,2,4]triazadiborin (80493-42-1) + isopropyl alcohol (67-63-0) → Triisopropyl borate (5419-55-6)

Conditions	Yield
byproducts: NH3; 8 h; further byproduct; chromd.;	70%
byproducts: 2,6-dimethylpiperidine, 1-amino-2,6-dimethylpiperidine, 2,3,4,5-tetrahydro-2,6-dimethylpiperidine; 8 h; further byproduct; chromd.;	70%

Trimethyl borate (121-43-7) + isopropyl alcohol (67-63-0) → Triisopropyl borate (5419-55-6)

isopropyl alcohol (67-63-0) → Triisopropyl borate (5419-55-6)

Conditions	Yield
With boric acid; benzene unter Entfernen des entstehenden Wassers;
With boron trioxide at 130℃;
With boron trioxide; toluene

acetone (67-64-1) + pentaborane(9) → Triisopropyl borate (5419-55-6)

di-isopropyl ether (108-20-3) + boron bromide → Triisopropyl borate (5419-55-6) + isopropyl bromide (75-26-3)

boron trioxide + isopropyl alcohol (67-63-0) → Triisopropyl borate (5419-55-6)

Conditions	Yield
at 100-120 °C;
With catalyst: Zeokar 2 In solid Kinetics; prepd. from predried reagents by mechanochemical activation in planetarycentrifuge mill at rotation frequency of 10-17 s**-1 for 1-30 min; equi librium reaction; analyzed by (1)H NMR spectroscopy and XRD;
With catalyst: zeolite NaA In solid Kinetics; prepd. from predried reagents by mechanochemical activation in planetarycentrifuge mill at rotation frequency of 10-17 s**-1 for 1-30 min; equi librium reaction; analyzed by (1)H NMR spectroscopy and XRD;
With catalyst: zeolite NaX In solid Kinetics; prepd. from predried reagents by mechanochemical activation in planetarycentrifuge mill at rotation frequency of 10-17 s**-1 for 1-30 min; equi librium reaction; analyzed by (1)H NMR spectroscopy and XRD;
at 100-120 °C;

Trimethyl borate (121-43-7) + Na{BH(iso-OC3H7)3} → Triisopropyl borate (5419-55-6) + sodium trimethoxyborohydride

Conditions	Yield
90°C, bomb tube;
90°C, bomb tube;

chloro-trimethyl-silane (75-77-4) + Hexamethyldisiloxane (107-46-0) + boric acid (11113-50-1) + isopropyl alcohol (67-63-0) → (C3H7O)2BOSi(CH3)3 + C3H7OB(OSi(CH3)3)2 + Triisopropyl borate (5419-55-6) + tris(trimethylsilyl)borate (4325-85-3)

Conditions	Yield
In neat (no solvent) Me3SiCl, Me3SiOSiMe3 and 2-propanol stirred for 30 min, boric acid added and stirred for 3 h; soln. filtered and concd., mixt. analysed by using combined gas chromatograph-mass spectroscopy;

+ isopropyl alcohol (67-63-0) → Triisopropyl borate (5419-55-6)

Conditions	Yield
In toluene to BH3*SMe2 in anhyd. toluene under N2 added i-PrOH; soln. stirred for 10 min; not isolated; monitored by GC/MS;
In neat (no solvent) byproducts: H2, S(CH3)2; react. in a round-bottom flask under N2, addn. of the alcohol to the borane complex at room temp. (stirred), refluxed (according to Brown, Krishnamurthy, J.Org.Chem. 1978, 43, 2731; with a slight modification); distn. from a small piece of K metal;

borane-THF (14044-65-6) + isopropyl alcohol (67-63-0) → Triisopropyl borate (5419-55-6)

Conditions	Yield
lithium triethylborohydride In tetrahydrofuran byproducts: H2; at 20°C with and without catalyst;

borane carbonyl + isopropyl alcohol (67-63-0) → Triisopropyl borate (5419-55-6)

Conditions	Yield
In neat (no solvent) at 0°C, molar ratio (OC)BH3:ROH=1:3;;
In neat (no solvent) at 0°C, molar ratio (OC)BH3:ROH=1:3;;

boric acid (11113-50-1) → Triisopropyl borate (5419-55-6)

Conditions	Yield
With isopropanol In benzene byproducts: water; distilled out at 138-140°C, elem. anal.;;

K-tetrakis(isopropoxy)borate → Triisopropyl borate (5419-55-6) + potassium isopropoxide (6831-82-9)

Conditions	Yield
In tetrahydrofuran potassium tetraisopropoxyborohydride refluxed in THF for 18 h; cooled to room temp., not isolated, detected by NMR;

allylboronic acid (6336-44-3, 7547-96-8, 7547-97-9, 88982-39-2) + isopropyl alcohol (67-63-0) → Triisopropyl borate (5419-55-6) + diisopropyl allylboronate (51851-79-7)

Conditions	Yield
In benzene byproducts: H2O; under Ar, soln. of allylboronic acid in C6H6 treated with 2-propanol (2 equiv), heated to reflux until evolution of H2O completed (Dean-Stark trap); fractionally distd. (bp 62-64°C, 40 mmHg);

ethylmagnesium bromide (925-90-6) + (E)-1-hexenyldiisopropoxyborane (91083-27-1) → diethyl(isopropoxy)borane (74953-03-0) + Triisopropyl borate (5419-55-6) + ethyl-1-hexenylisopropoxyborane (148058-18-8)

Conditions	Yield
With methanesulfonic acid In tetrahydrofuran dropwise addn. of EtMgBr (1-3 equiv.) to soln. of C6H11B(OCH(CH3)2)2 (2.5 mmol) in THF at -78°C via syringe; stirring at -78°C for 3 h; addn. of CH3SO3H at -78°C; warming slowly to room temp.; stirring (room temp.);; not isolated; product distribution is determined by 11B-NMR;;

ethylmagnesium bromide (925-90-6) + (E)-1-hexenyldiisopropoxyborane (91083-27-1) → Triisopropyl borate (5419-55-6) + ethyl-1-hexenylisopropoxyborane (148058-18-8)

Conditions	Yield
With acetyl chloride In diethyl ether dropwise addn. of EtMgBr (1-2.5 equiv.) to soln. of C6H11B(OCH(CH3)2)2 (2.5 mmol) in ether at -78°C via syringe; stirring at -78°C for 3 h; addn. of CH3COCl at -78°C; warming slowly to room temp.; stirring (room temp.);; not isolated; product distribution is determined by 11B-NMR;;

isopropylmagnesium chloride (1068-55-9) + (E)-1-hexenyldiisopropoxyborane (91083-27-1) → Triisopropyl borate (5419-55-6) + C6H11B(CH(CH3)2)2 + isopropyl-1-hexenylisopropoxyborane (148058-19-9) + {C6H11B(OCH(CH3)2)(CH(CH3)2)2}(1-)*Mg(2+)*Cl(1-)={C6H11B(OCH(CH3)2)(CH(CH3)2)2}MgCl

Conditions	Yield
With chloro-trimethyl-silane In tetrahydrofuran dropwise addn. of i-PrMgBr (2 equiv.) to soln. of C6H11B(OCH(CH3)2)2 (2.5 mmol) in THF at -78°C via syringe; stirring at -78°C for 3 h; addn. of (CH3)3SiCl at -78°C; warming slowly to room temp.; stirring (room temp.);; not isolated; product distribution is determined by 11B-NMR;;

isobutylmagnesium bromide (926-62-5) + (E)-1-hexenyldiisopropoxyborane (91083-27-1) → Triisopropyl borate (5419-55-6) + isobutyl-1-hexenylisopropoxyborane (148058-20-2)

Conditions	Yield
With methanesulfonic acid In tetrahydrofuran dropwise addn. of i-BuMgBr (2 equiv.) to soln. of C6H11B(OCH(CH3)2)2 (2.5 mmol) in THF at -78°C via syringe; stirring at -78°C for 3 h; addn. of CH3SO3H at -78°C; warming slowly to room temp.; stirring at room temp.;; not isolated; product distribution is determined by 11B-NMR;;

methyllithium (917-54-4) + (E)-1-hexenyldiisopropoxyborane (91083-27-1) → dimethylisopropoxyborane + Triisopropyl borate (5419-55-6) + C6H11B(CH3)2 + methyl-1-hexenylisopropoxyborane (148058-10-0) + diisopropoxymethylborane (86595-27-9)

Conditions	Yield
With methanesulfonic acid In hexane byproducts: (CH3)3B; dropwise addn. of CH3Li (1 equiv.) to soln. of C6H11B(OCH(CH3)2)2 (2.5 mmol) in hexane at -78°C via syringe; stirring at -78°C for 3 h; addn. of CH3SO3H at 0/25°C; warming slowly to room temp.; stirring at room temp.;; not isolated; product distribution (depending on temp. at which acid is added) is determined by 11B-NMR;;

methyllithium (917-54-4) + (E)-1-hexenyldiisopropoxyborane (91083-27-1) → dimethylisopropoxyborane + Triisopropyl borate (5419-55-6) + methyl-1-hexenylisopropoxyborane (148058-10-0) + diisopropoxymethylborane (86595-27-9)

Conditions	Yield
With CH3SO3H or HCl or CH3COCl or ClCH2COCl or Cl3CCOCl In diethyl ether addn. of CH3Li to soln. of C6H11B(OCH(CH3)2)2 (2.5 mmol) in ether at -78°C via syringe; stirring at -78°C for 3 h; addn. of acid (further acids investigated: ClCH2COCl, (CH3)3SiCl); warming slowly to room temp.; stirring at room temp.;; not isolated; product distribution is determined by 11B-NMR for various conditions (temp. at which acid is added, amt. of CH3Li, amt. of acid);;
With CH3SO3H or HCl or CH3COCl or ClCH2COCl or Cl3CCOCl In tetrahydrofuran addn. of CH3Li to soln. of C6H11B(OCH(CH3)2)2 (2.5 mmol) in THF at -78°C via syringe; stirring at -78°C for 3 h; addn. of acid (further acids investigated: ClCH2COCl, (CH3)3SiCl); warming slowly to room temp.; stirring at room temp.;; not isolated; product distribution is determined by 11B-NMR for various conditions (temp. at which acid is added, amt. of CH3Li, amt. of acid);;
With methanesulfonic acid In hexane dropwise addn. of CH3Li (1 equiv.) to soln. of C6H11B(OCH(CH3)2)2 (2.5 mmol) in hexane at -78°C via syringe; stirring at -78°C for 3 h; addn. of CH3SO3H at -78°C; warming slowly to room temp.; stirring at room temp.;; not isolated; product distribution is determined by 11B-NMR;;

potassium tri(isopropoxy)borohydride + C8H14BBrS(CH3)2 (70160-59-7) → Triisopropyl borate (5419-55-6) + 9-bora-bicyclo[3.3.1]nonane (280-64-8)

Conditions	Yield
In tetrahydrofuran byproducts: B-alkoxy-9-borabicyclo[3.3.1]nonane, KBr; 1 equivalent K(i-PrO)3BH, 25°C, 8.0 h; detected by 11B NMR;
In tetrahydrofuran byproducts: B-alkoxy-9-borabicyclo[3.3.1]nonane, KBr; 1 equivalent K(i-PrO)3BH, 0°C, 0.25 h; detected by 11B NMR;

potassium tri(isopropoxy)borohydride + C8H14BClS(CH3)2 (70160-58-6) → Triisopropyl borate (5419-55-6) + potassium (cyclooctane-1,5-diyl)dihydroborate (76448-06-1)

Conditions	Yield
In tetrahydrofuran 2 equivalent K(i-PrO)3BH, 25°C, 0.25 h; detected by 11B NMR;

potassium tri(isopropoxy)borohydride + C8H14BClS(CH3)2 (70160-58-6) → Triisopropyl borate (5419-55-6) + 9-bora-bicyclo[3.3.1]nonane (280-64-8)

Conditions	Yield
In tetrahydrofuran byproducts: B-alkoxy-9-borabicyclo-[3.3.1]nonane, KCl; 1 equivalent K(i-PrO)3BH, 0°C, 0.25 h; detected by 11B NMR;

Triisopropyl borate (5419-55-6) + phenylacetylene (536-74-3) → lithium triisopropyl-B-(phenylethynyl)boronate

Conditions	Yield
With n-butyllithium In diethyl ether at 20℃; Substitution;	100%
Stage #1: phenylacetylene With n-butyllithium In diethyl ether at -78℃; for 0.5h; Metallation; Stage #2: Triisopropyl borate In diethyl ether at -78℃; for 0.166667h; Addition;
Stage #1: phenylacetylene With n-butyllithium In diethyl ether; hexane at -78℃; Metallation; Stage #2: Triisopropyl borate In diethyl ether; hexane at -78 - 20℃; Addition; Further stages.;

Triisopropyl borate (5419-55-6) + tert-Butyldimethyl(prop-2-ynyloxy)silane (76782-82-6) → C18H38BO4Si(1-)*Li(1+)

Conditions	Yield
With n-butyllithium In diethyl ether at 20℃; Substitution;	100%

Triisopropyl borate (5419-55-6) + hex-1-yne (693-02-7) → C15H30BO3(1-)*Li(1+)

Conditions	Yield
With n-butyllithium In diethyl ether at 20℃; Substitution;	100%

Triisopropyl borate (5419-55-6) + pinanediol (18680-27-8) → (3aS,4s,6S,7aR)-hexahydro-3a,5,5-trimethyl-2-(1-methylethoxy)-4,6-methano-1,3,2-benzodioxaborole (819816-59-6)

Conditions	Yield
In dichloromethane at 0 - 20℃;	100%
In toluene for 0.5h; Heating;	93%
In tetrahydrofuran at 0℃; for 2h;	90%
In tetrahydrofuran at 0℃; for 2h;	90%
In dichloromethane at 0 - 23℃;

Triisopropyl borate (5419-55-6) → C16H24BNO3

Conditions	Yield
Stage #1: 5-bromo-2-[(1-methylethyl)oxy]benzonitrile With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.75h; Stage #2: Triisopropyl borate In tetrahydrofuran; hexane at -78 - -20℃;	100%

5-bromo-2,2-difluoro-2H-1,3-benzodioxole (33070-32-5) + Triisopropyl borate (5419-55-6) → (2,2-difluoro-1,3-benzodioxol-5-yl)boronic acid (190903-71-0)

Conditions	Yield
With n-butyllithium In tetrahydrofuran at -65 - -60℃; Inert atmosphere;	100%
Stage #1: 5-bromo-2,2-difluoro-2H-1,3-benzodioxole With n-butyllithium In tetrahydrofuran; hexane for 0.5h; Inert atmosphere; Cooling with acetone-dry ice; Stage #2: Triisopropyl borate In tetrahydrofuran; hexane at 20℃; for 0.5h; Stage #3: With acetic acid In tetrahydrofuran; hexane at 20℃; for 0.166667h;	73%
Stage #1: 5-bromo-2,2-difluoro-2H-1,3-benzodioxole With n-butyllithium In tetrahydrofuran; hexanes Stage #2: Triisopropyl borate In tetrahydrofuran; hexanes at 20℃; Stage #3: With acetic acid In tetrahydrofuran; hexanes at 20℃; for 0.166667h;	73%

Triisopropyl borate (5419-55-6) + sodium hydroxide (1310-73-2) + N-(n-butyl)-2-(2-bromophenyl)-benzimidazole (815581-69-2) → 2-(2-boronophenyl)-N-n-butylbenzimidazole sodium hydroxide salt

Conditions	Yield
With tert.-butyl lithium In diethyl ether; pentane a soln. of benzimidazole-compound in ether at -78°C under Ar was treated with t-BuLi in pentane over 15 min, stirred at -78.degre.C for 1h, treated with B(Oi-Pr)3, stirred for 48 h, allowed to warm to room te mp., NaOH was added, stirred for 1 h; ppt. was filtered, washed with ether, dried;	100%

Triisopropyl borate (5419-55-6) + (S)-diphenylprolinol (22348-32-9, 63401-04-7, 112022-88-5, 112068-01-6) + ethylene glycol (107-21-1) → 2-[(1,3,2-dioxaborolan-2-yloxy)diphenylmethyl]pyrrolidine

Conditions	Yield
Stage #1: Triisopropyl borate; ethylene glycol In toluene Heating / reflux; Stage #2: (S)-diphenylprolinol In toluene at 80℃; under 20 Torr; for 1h;	100%
In toluene at 80℃; for 1h; Inert atmosphere;	100%
Stage #1: Triisopropyl borate; ethylene glycol In toluene Inert atmosphere; Reflux; Stage #2: (S)-diphenylprolinol In toluene at 80℃; for 1h; Inert atmosphere; Reflux;	100%
Stage #1: Triisopropyl borate; ethylene glycol In toluene Inert atmosphere; Reflux; Stage #2: (S)-diphenylprolinol In toluene at 80℃; for 1h; Inert atmosphere;

Triisopropyl borate (5419-55-6) + 1,1-diphenyl-L-valinol (78603-95-9) + ethylene glycol (107-21-1) → 1-[([1,3,2]dioxaborolan-2-yloxy)-diphenyl-methyl]-2-methylpropylamine

Conditions	Yield
Stage #1: Triisopropyl borate; ethylene glycol In toluene Heating / reflux; Stage #2: 1,1-diphenyl-L-valinol In toluene at 80℃; under 20 Torr; for 1h;	100%

Triisopropyl borate (5419-55-6) + (1R,2S)-norephedrine (492-41-1) + ethylene glycol (107-21-1) → (1R,2S)-1-(1',3',2'-dioxaborolan-2'-yloxy)-1-phenylpropan-2-amine

Conditions	Yield
Stage #1: Triisopropyl borate; ethylene glycol In toluene for 0.05h; Heating / reflux; Stage #2: (1R,2S)-norephedrine In toluene at 20 - 80℃; for 1h;	100%

Triisopropyl borate (5419-55-6) + (R)-(+)-2-amino-1,1,2-triphenylethanol (60539-17-5, 79868-79-4, 129704-13-8) + ethylene glycol (107-21-1) → (R)-(+)-2-(1,3,2-dioxaborolan-2-yloxy)-1,2,2-triphenylethanamine

Conditions	Yield
Stage #1: Triisopropyl borate; ethylene glycol In toluene for 0.05h; Heating / reflux; Stage #2: (R)-(+)-2-amino-1,1,2-triphenylethanol In toluene at 20 - 80℃; for 1h;	100%

Triisopropyl borate (5419-55-6) + 7-bromo-2H-pyrano[3,2-b]pyridine (1073633-66-5) → 2H-pyrano[3,2-b]pyridin-7-ylboronic acid (1073633-67-6)

Conditions	Yield
Stage #1: 7-bromo-2H-pyrano[3,2-b]pyridine With n-butyllithium In hexanes; diethyl ether for 0.0833333h; Stage #2: Triisopropyl borate In hexanes; diethyl ether at -78 - 20℃;	100%

2-bromo-pyridine (109-04-6) + n-butyllithium (109-72-8, 29786-93-4) + Triisopropyl borate (5419-55-6) → lithium (pyridine-2-yl)triisopropoxyborate

Conditions	Yield
In tetrahydrofuran; toluene at -78 - 20℃; Inert atmosphere; Cooling with acetone-dry ice;	100%
In tetrahydrofuran; toluene 1. triisopropylborate, toluene/THF 4/1; 2. n-C4H9Li over 90 min, -78°C to room temp.;	99%

Triisopropyl borate (5419-55-6) + 3-bromo-7,12-diphenylbenzo[k]fluoranthene (187086-32-4) → 7,12-diphenylbenzo[k]fluoranthen-3-ylboronic acid (276249-59-3)

Conditions	Yield
Stage #1: 3-bromo-7,12-diphenylbenzo[k]fluoranthene With n-butyllithium In tetrahydrofuran at -80℃; for 0.25h; Stage #2: Triisopropyl borate In tetrahydrofuran	100%
Stage #1: 3-bromo-7,12-diphenylbenzo[k]fluoranthene With n-butyllithium In tetrahydrofuran; toluene at -70℃; Inert atmosphere; Stage #2: Triisopropyl borate In tetrahydrofuran; toluene at -70 - 20℃; for 2h;	88%
Stage #1: 3-bromo-7,12-diphenylbenzo[k]fluoranthene With n-butyllithium In tetrahydrofuran; toluene at -70℃; for 1h; Stage #2: Triisopropyl borate In tetrahydrofuran; toluene at 20℃; for 2h;	88%
Stage #1: 3-bromo-7,12-diphenylbenzo[k]fluoranthene With n-butyllithium In tetrahydrofuran; toluene at -70℃; for 1h; Stage #2: Triisopropyl borate In tetrahydrofuran; toluene at -70 - 20℃; for 2h; Stage #3: With hydrogenchloride In tetrahydrofuran; water; toluene at 20℃; for 2h;	88%
Stage #1: 3-bromo-7,12-diphenylbenzo[k]fluoranthene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: Triisopropyl borate In tetrahydrofuran; hexane at 20℃;

Triisopropyl borate (5419-55-6) + 3-Bromo-N-tert-butoxycarbonyl-N-methylaniline (57598-34-2) → (3-((tert-butoxycarbonyl)(methyl)amino)phenyl)boronic acid (887831-90-5)

Conditions	Yield
Stage #1: 3-Bromo-N-tert-butoxycarbonyl-N-methylaniline With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: Triisopropyl borate In tetrahydrofuran; hexane at -78℃; for 2h; Stage #3: With hydrogenchloride; water In tetrahydrofuran; hexane at -10℃;	100%

Triisopropyl borate (5419-55-6) + 3-bromofluoranthene (13438-50-1) → 7,12-diphenylbenzo[k]fluoranthene-3-boronic acid (359012-63-8)

Conditions	Yield
With n-butyllithium; water In tetrahydrofuran at -80℃; for 0.25h;	100%
Stage #1: 3-bromofluoranthene With n-butyllithium In tetrahydrofuran at -100℃; for 2h; Inert atmosphere; Stage #2: Triisopropyl borate In tetrahydrofuran for 4h; Inert atmosphere;	70%
Stage #1: 3-bromofluoranthene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: Triisopropyl borate In tetrahydrofuran; hexane at -78℃; for 2h;	60%
In tetrahydrofuran at -78℃;

n-butyllithium (109-72-8, 29786-93-4) + 2-bromo-4-methoxypyridine (89488-29-9) + Triisopropyl borate (5419-55-6) → lithium triisopropyl 2-(4-methoxypyridyl)borate

Conditions	Yield
In tetrahydrofuran; toluene at -78 - 20℃; Inert atmosphere; Cooling with acetone-dry ice;	100%

n-butyllithium (109-72-8, 29786-93-4) + Triisopropyl borate (5419-55-6) + 2-bromo-4-chloropyridine (22918-01-0) → lithium triisopropyl 2-(4-chloropyridyl)borate

Conditions	Yield
In tetrahydrofuran; toluene at -78 - 20℃; Inert atmosphere; Cooling with acetone-dry ice;	100%

Triisopropyl borate (5419-55-6) + (S)-2-bromo-4-fluoro-1-(pent-4-en-2-yloxy)benzene → (S)-(5-fluoro-2-(pent-4-en-2-yloxy)phenyl)boronic acid

Conditions	Yield
Stage #1: (S)-2-bromo-4-fluoro-1-(pent-4-en-2-yloxy)benzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: Triisopropyl borate In tetrahydrofuran; hexane for 0.166667h;	100%
Stage #1: (S)-2-bromo-4-fluoro-1-(pent-4-en-2-yloxy)benzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: Triisopropyl borate In tetrahydrofuran; hexane at -78 - 20℃; for 0.5h; Stage #3: With hydrogenchloride In tetrahydrofuran; hexane; water

Triisopropyl borate (5419-55-6) + (S)-5-bromo-2-(2-(trifluoromethyl)pyrrolidin-1-yl)pyrimidine (1620136-60-8) → (S)-(2-(2-(trifluoromethyl)pyrrolidin-1-yl)pyrimidin-5-yl)boronic acid

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere;	100%
With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere;	100%

Triisopropyl borate (5419-55-6) + (S)-(-)-2-amino-1,1,3-triphenyl-1-propanol (79868-78-3) + ethylene glycol (107-21-1) → C23H24BNO3

Conditions	Yield
In toluene at 80℃; for 1h; Inert atmosphere;	100%
Stage #1: Triisopropyl borate; ethylene glycol In toluene Inert atmosphere; Reflux; Stage #2: (S)-(-)-2-amino-1,1,3-triphenyl-1-propanol In toluene at 80℃; for 1h; Inert atmosphere; Reflux;	100%

Triisopropyl borate (5419-55-6) + (S)-(-)-α,α-di(2-naphthyl)-2-pyrrolidinemethanol (130798-48-0, 127986-84-9) + ethylene glycol (107-21-1) → C27H26BNO3

Conditions	Yield
In toluene at 80℃; for 1h; Inert atmosphere;	100%
Stage #1: Triisopropyl borate; ethylene glycol In toluene Inert atmosphere; Reflux; Stage #2: (S)-(-)-α,α-di(2-naphthyl)-2-pyrrolidinemethanol In toluene at 80℃; for 1h; Inert atmosphere; Reflux;	100%

Triisopropyl borate (5419-55-6) + (R)-α,α-diphenylprolinol (22348-32-9) + ethylene glycol (107-21-1) → (R)-2-[(1,3,2-dioxaborolan-2-yloxy)diphenylmethyl]pyrrolidine

Conditions	Yield
In toluene at 80℃; for 1h; Inert atmosphere;	100%
Stage #1: Triisopropyl borate; ethylene glycol In toluene Inert atmosphere; Reflux; Stage #2: (R)-α,α-diphenylprolinol In toluene at 80℃; for 1h; Inert atmosphere; Reflux;	100%
Stage #1: Triisopropyl borate; ethylene glycol In toluene Inert atmosphere; Reflux; Stage #2: (R)-α,α-diphenylprolinol In toluene at 80℃; for 1h; Inert atmosphere;	90%

2,3-dimethyl-2,3-butane diol (76-09-5) + Triisopropyl borate (5419-55-6) + (S)-diphenylprolinol (22348-32-9, 63401-04-7, 112022-88-5, 112068-01-6) → (3'aS)-4,4,5,5-tetramethyl-3',3'-diphenylhexahydrospiro[[1,3,2]dioxaborolane-2,1'-pyrrolo[1,2-c][1,3,2]oxazaborol]-7'-ium-1'-uide

Conditions	Yield
In toluene at 80℃; for 1h; Inert atmosphere;	100%
Stage #1: 2,3-dimethyl-2,3-butane diol; Triisopropyl borate In toluene Inert atmosphere; Reflux; Stage #2: (S)-diphenylprolinol In toluene at 80℃; for 1h; Inert atmosphere; Reflux;	100%

Triisopropyl borate (5419-55-6) + (S)-diphenylprolinol (22348-32-9, 63401-04-7, 112022-88-5, 112068-01-6) + benzene-1,2-diol (120-80-9) → C23H22BNO3

Conditions	Yield
In toluene at 80℃; for 1h; Inert atmosphere;	100%
Stage #1: Triisopropyl borate; benzene-1,2-diol In toluene Inert atmosphere; Reflux; Stage #2: (S)-diphenylprolinol In toluene at 80℃; for 1h; Inert atmosphere; Reflux;	100%

Triisopropyl borate (5419-55-6) + ethylene glycol (107-21-1) + N-[(1S,2S)-2-amino-1,2-diphenylethyl]-4-methylbenzenesulfonamide (167316-27-0) → C23H25BN2O4S

Conditions	Yield
Stage #1: Triisopropyl borate; ethylene glycol In toluene Inert atmosphere; Reflux; Stage #2: N-[(1S,2S)-2-amino-1,2-diphenylethyl]-4-methylbenzenesulfonamide In toluene at 80℃; for 1h; Inert atmosphere; Reflux;	100%

Triisopropyl borate (5419-55-6) + (R)-(+)-α,α-di-(2-naphthyl)-2-pyrrolidinemethanol (130798-48-0) + ethylene glycol (107-21-1) → C27H26BNO3

Conditions	Yield
Stage #1: Triisopropyl borate; ethylene glycol In toluene Inert atmosphere; Reflux; Stage #2: (R)-(+)-α,α-di-(2-naphthyl)-2-pyrrolidinemethanol In toluene at 80℃; for 1h; Inert atmosphere; Reflux;	100%

Triisopropyl borate (5419-55-6) + 2-bromobenzo[9,10]phenanthrene (19111-87-6) → benzo[l]phenanthrene-2-boronic acid (654664-63-8)

Conditions	Yield
Stage #1: 2-bromobenzo[9,10]phenanthrene With n-butyllithium In tetrahydrofuran for 0.25h; Heating; Stage #2: Triisopropyl borate In tetrahydrofuran	100%

Triisopropyl borate (5419-55-6) + 4-bromo-2-(dimethoxymethyl)pyridine → (2-(dimethoxymethyl)pyridin-4-yl)boric acid lithium salt

Conditions	Yield
With n-butyllithium In tetrahydrofuran; toluene at -78 - 20℃; Inert atmosphere;	100%

Triisopropyl borate (5419-55-6) + 2-tert-butyl-4-iodo-1-(2-methoxy-ethoxymethoxy)-benzene → 3-tert-butyl-4-(2-methoxy-ethoxymethoxy)-benzene boronic acid

Conditions	Yield
Stage #1: 2-tert-butyl-4-iodo-1-(2-methoxy-ethoxymethoxy)-benzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: Triisopropyl borate In tetrahydrofuran; hexane at -78 - 20℃; for 2h;	100%

Upstream product

• 121-43-7 Trimethyl borate 
• 67-63-0 isopropyl alcohol 
• 108-20-3 di-isopropyl ether 
• 11113-50-1 boric acid 
• 80493-42-1 2,3,4-Tris(2,6-dimethylpiperidino)-1,3,4,6,7,8,9,9a-octahydro-6,9a-dimethyl-2H-pyrido[1,2-e][1,3,5,2,4]triazadiborin 
• 75-77-4 chloro-trimethyl-silane 
• 107-46-0 Hexamethyldisiloxane 
• 13292-87-0 dimethylsulfide borane complex 
• 6336-44-3 allylboronic acid 
• 70160-59-7 C₈H₁₄BBrS(CH₃)2 
• 70160-58-6 C₈H₁₄BClS(CH₃)2 
• 14610-26-5 1-phenyl-2-bis(dimethylamino)borylethyne 
• 14610-27-6 bis(dimethylamino)propynylborane 
• 917-54-4 methyllithium 

Downstream Products

• 121-43-7 Trimethyl borate 
• 19097-72-4 (i-C₃H₇O)2B(O-C₆H₃-2.6-(t-C₄H₉)2) 
• 2929-87-5 2,6-Di-t-butyl-p-kresyl-diisopropylborat 
• 19097-73-5 (i-C₃H₇O)2B(OC₆H₂(C₄H₉)2C(CH₃)3) 
• 10298-87-0 triisopropoxyboroxin 
• 951-19-9 isopropyl α-naphthoate 
• 64450-63-1 m-Tolyl-acetic acid isopropyl ester 
• 57404-76-9 trans-1-heptenylboronic acid 
• 5735-41-1 3H-benzo[c][1,2]oxaborol-1-ol 
• 64450-64-2 isopropyl 2-p-tolylacetate 
• 106970-46-1 C₁₃H₂₁BO₃ 
• 620987-93-1 C₂₀H₃₅BO₂ 
• 143418-49-9 3,4,5-trifluorophenylboronic acid 

Relevant articles and documents

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