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Triisopropyl borate Manufacturer/High quality/Best price/In stock
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5419-55-6 Triisopropyl borate
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5419-55-6 Usage

Air & Water Reactions

Highly flammable. Insoluble in water.

Chemical Properties

clear colourless liquid

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.

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.

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

5419-55-6 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
Alfa Aesar (A17592)  Triisopropyl borate, 98+%    5419-55-6 100ml 530.0CNY Detail
Alfa Aesar (A17592)  Triisopropyl borate, 98+%    5419-55-6 500ml 1181.0CNY Detail
Alfa Aesar (A17592)  Triisopropyl borate, 98+%    5419-55-6 2500ml 4706.0CNY Detail
Aldrich (197335)  Triisopropylborate  ≥98% 5419-55-6 197335-80G 507.78CNY Detail
Aldrich (197335)  Triisopropylborate  ≥98% 5419-55-6 197335-750G 2,502.63CNY Detail
Aldrich (197335)  Triisopropylborate  ≥98% 5419-55-6 197335-2KG 4,967.82CNY Detail

5419-55-6SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Triisopropyl Borate

1.2 Other means of identification

Product number -
Other names Tri-i-Propylborate

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:5419-55-6 SDS

5419-55-6Synthetic route

zirconium(IV) borohydride

zirconium(IV) borohydride

isopropyl alcohol
67-63-0

isopropyl alcohol

A

Triisopropyl borate
5419-55-6

Triisopropyl borate

B

zirconium isopropoxide

zirconium isopropoxide

Conditions
ConditionsYield
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

triisopropoxyboroxin

isopropyl alcohol
67-63-0

isopropyl alcohol

Triisopropyl borate
5419-55-6

Triisopropyl borate

Conditions
ConditionsYield
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

hafnium borohydride

isopropyl alcohol
67-63-0

isopropyl alcohol

A

Triisopropyl borate
5419-55-6

Triisopropyl borate

B

hafnium(IV) isopropoxide isopropanolate

hafnium(IV) isopropoxide isopropanolate

Conditions
ConditionsYield
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

boric acid

isopropyl alcohol
67-63-0

isopropyl alcohol

Triisopropyl borate
5419-55-6

Triisopropyl borate

Conditions
ConditionsYield
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

U(BH4)3(OCH(CH3)2)(C4H8O)2

A

Triisopropyl borate
5419-55-6

Triisopropyl borate

B

U(BH4)2(OCH(CH3)2)2(C4H8O)2

U(BH4)2(OCH(CH3)2)2(C4H8O)2

Conditions
ConditionsYield
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

1-[Amino(diisopropylamino)boryl]-2-[bis(diisopropylamino)boryl]-2-isopropenyl-1-isopropylhydrazin

isopropyl alcohol
67-63-0

isopropyl alcohol

Triisopropyl borate
5419-55-6

Triisopropyl borate

Conditions
ConditionsYield
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

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

isopropyl alcohol
67-63-0

isopropyl alcohol

Triisopropyl borate
5419-55-6

Triisopropyl borate

Conditions
ConditionsYield
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

Trimethyl borate

isopropyl alcohol
67-63-0

isopropyl alcohol

Triisopropyl borate
5419-55-6

Triisopropyl borate

isopropyl alcohol
67-63-0

isopropyl alcohol

Triisopropyl borate
5419-55-6

Triisopropyl borate

Conditions
ConditionsYield
With boric acid; benzene unter Entfernen des entstehenden Wassers;
With boron trioxide at 130℃;
With boron trioxide; toluene
acetone
67-64-1

acetone

pentaborane(9)

pentaborane(9)

Triisopropyl borate
5419-55-6

Triisopropyl borate

di-isopropyl ether
108-20-3

di-isopropyl ether

boron bromide

boron bromide

A

Triisopropyl borate
5419-55-6

Triisopropyl borate

B

isopropyl bromide
75-26-3

isopropyl bromide

boron trioxide

boron trioxide

isopropyl alcohol
67-63-0

isopropyl alcohol

Triisopropyl borate
5419-55-6

Triisopropyl borate

Conditions
ConditionsYield
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

Trimethyl borate

Na{BH(iso-OC3H7)3}

Na{BH(iso-OC3H7)3}

A

Triisopropyl borate
5419-55-6

Triisopropyl borate

B

sodium trimethoxyborohydride

sodium trimethoxyborohydride

Conditions
ConditionsYield
90°C, bomb tube;
90°C, bomb tube;
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

Hexamethyldisiloxane
107-46-0

Hexamethyldisiloxane

boric acid
11113-50-1

boric acid

isopropyl alcohol
67-63-0

isopropyl alcohol

A

(C3H7O)2BOSi(CH3)3

(C3H7O)2BOSi(CH3)3

B

C3H7OB(OSi(CH3)3)2

C3H7OB(OSi(CH3)3)2

C

Triisopropyl borate
5419-55-6

Triisopropyl borate

D

tris(trimethylsilyl)borate
4325-85-3

tris(trimethylsilyl)borate

Conditions
ConditionsYield
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

isopropyl alcohol

Triisopropyl borate
5419-55-6

Triisopropyl borate

Conditions
ConditionsYield
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

borane-THF

isopropyl alcohol
67-63-0

isopropyl alcohol

Triisopropyl borate
5419-55-6

Triisopropyl borate

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

borane carbonyl

isopropyl alcohol
67-63-0

isopropyl alcohol

Triisopropyl borate
5419-55-6

Triisopropyl borate

Conditions
ConditionsYield
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

boric acid

Triisopropyl borate
5419-55-6

Triisopropyl borate

Conditions
ConditionsYield
With isopropanol In benzene byproducts: water; distilled out at 138-140°C, elem. anal.;;
K-tetrakis(isopropoxy)borate

K-tetrakis(isopropoxy)borate

A

Triisopropyl borate
5419-55-6

Triisopropyl borate

B

potassium isopropoxide
6831-82-9

potassium isopropoxide

Conditions
ConditionsYield
In tetrahydrofuran potassium tetraisopropoxyborohydride refluxed in THF for 18 h; cooled to room temp., not isolated, detected by NMR;
isopropyl alcohol
67-63-0

isopropyl alcohol

A

Triisopropyl borate
5419-55-6

Triisopropyl borate

B

diisopropyl allylboronate
51851-79-7

diisopropyl allylboronate

Conditions
ConditionsYield
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

ethylmagnesium bromide

(E)-1-hexenyldiisopropoxyborane
91083-27-1

(E)-1-hexenyldiisopropoxyborane

A

diethyl(isopropoxy)borane
74953-03-0

diethyl(isopropoxy)borane

B

Triisopropyl borate
5419-55-6

Triisopropyl borate

C

ethyl-1-hexenylisopropoxyborane
148058-18-8

ethyl-1-hexenylisopropoxyborane

Conditions
ConditionsYield
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

ethylmagnesium bromide

(E)-1-hexenyldiisopropoxyborane
91083-27-1

(E)-1-hexenyldiisopropoxyborane

A

Triisopropyl borate
5419-55-6

Triisopropyl borate

B

ethyl-1-hexenylisopropoxyborane
148058-18-8

ethyl-1-hexenylisopropoxyborane

Conditions
ConditionsYield
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

isopropylmagnesium chloride

(E)-1-hexenyldiisopropoxyborane
91083-27-1

(E)-1-hexenyldiisopropoxyborane

A

Triisopropyl borate
5419-55-6

Triisopropyl borate

B

C6H11B(CH(CH3)2)2

C6H11B(CH(CH3)2)2

C

isopropyl-1-hexenylisopropoxyborane
148058-19-9

isopropyl-1-hexenylisopropoxyborane

D

{C6H11B(OCH(CH3)2)(CH(CH3)2)2}(1-)*Mg(2+)*Cl(1-)={C6H11B(OCH(CH3)2)(CH(CH3)2)2}MgCl

{C6H11B(OCH(CH3)2)(CH(CH3)2)2}(1-)*Mg(2+)*Cl(1-)={C6H11B(OCH(CH3)2)(CH(CH3)2)2}MgCl

Conditions
ConditionsYield
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

isobutylmagnesium bromide

(E)-1-hexenyldiisopropoxyborane
91083-27-1

(E)-1-hexenyldiisopropoxyborane

A

Triisopropyl borate
5419-55-6

Triisopropyl borate

B

isobutyl-1-hexenylisopropoxyborane
148058-20-2

isobutyl-1-hexenylisopropoxyborane

Conditions
ConditionsYield
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

methyllithium

(E)-1-hexenyldiisopropoxyborane
91083-27-1

(E)-1-hexenyldiisopropoxyborane

A

dimethylisopropoxyborane

dimethylisopropoxyborane

B

Triisopropyl borate
5419-55-6

Triisopropyl borate

C

C6H11B(CH3)2

C6H11B(CH3)2

D

methyl-1-hexenylisopropoxyborane
148058-10-0

methyl-1-hexenylisopropoxyborane

E

diisopropoxymethylborane
86595-27-9

diisopropoxymethylborane

Conditions
ConditionsYield
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

methyllithium

(E)-1-hexenyldiisopropoxyborane
91083-27-1

(E)-1-hexenyldiisopropoxyborane

A

dimethylisopropoxyborane

dimethylisopropoxyborane

B

Triisopropyl borate
5419-55-6

Triisopropyl borate

C

methyl-1-hexenylisopropoxyborane
148058-10-0

methyl-1-hexenylisopropoxyborane

D

diisopropoxymethylborane
86595-27-9

diisopropoxymethylborane

Conditions
ConditionsYield
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

potassium tri(isopropoxy)borohydride

C8H14BBrS(CH3)2
70160-59-7

C8H14BBrS(CH3)2

A

Triisopropyl borate
5419-55-6

Triisopropyl borate

B

9-bora-bicyclo[3.3.1]nonane
280-64-8

9-bora-bicyclo[3.3.1]nonane

Conditions
ConditionsYield
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

potassium tri(isopropoxy)borohydride

C8H14BClS(CH3)2
70160-58-6

C8H14BClS(CH3)2

A

Triisopropyl borate
5419-55-6

Triisopropyl borate

B

potassium (cyclooctane-1,5-diyl)dihydroborate
76448-06-1

potassium (cyclooctane-1,5-diyl)dihydroborate

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

potassium tri(isopropoxy)borohydride

C8H14BClS(CH3)2
70160-58-6

C8H14BClS(CH3)2

A

Triisopropyl borate
5419-55-6

Triisopropyl borate

B

9-bora-bicyclo[3.3.1]nonane
280-64-8

9-bora-bicyclo[3.3.1]nonane

Conditions
ConditionsYield
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

Triisopropyl borate

phenylacetylene
536-74-3

phenylacetylene

lithium triisopropyl-B-(phenylethynyl)boronate

lithium triisopropyl-B-(phenylethynyl)boronate

Conditions
ConditionsYield
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

Triisopropyl borate

tert-Butyldimethyl(prop-2-ynyloxy)silane
76782-82-6

tert-Butyldimethyl(prop-2-ynyloxy)silane

C18H38BO4Si(1-)*Li(1+)

C18H38BO4Si(1-)*Li(1+)

Conditions
ConditionsYield
With n-butyllithium In diethyl ether at 20℃; Substitution;100%
Triisopropyl borate
5419-55-6

Triisopropyl borate

hex-1-yne
693-02-7

hex-1-yne

C15H30BO3(1-)*Li(1+)

C15H30BO3(1-)*Li(1+)

Conditions
ConditionsYield
With n-butyllithium In diethyl ether at 20℃; Substitution;100%
Triisopropyl borate
5419-55-6

Triisopropyl borate

pinanediol
18680-27-8

pinanediol

(3aS,4s,6S,7aR)-hexahydro-3a,5,5-trimethyl-2-(1-methylethoxy)-4,6-methano-1,3,2-benzodioxaborole
819816-59-6

(3aS,4s,6S,7aR)-hexahydro-3a,5,5-trimethyl-2-(1-methylethoxy)-4,6-methano-1,3,2-benzodioxaborole

Conditions
ConditionsYield
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

Triisopropyl borate

C16H24BNO3

C16H24BNO3

Conditions
ConditionsYield
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

5-bromo-2,2-difluoro-2H-1,3-benzodioxole

Triisopropyl borate
5419-55-6

Triisopropyl borate

(2,2-difluoro-1,3-benzodioxol-5-yl)boronic acid
190903-71-0

(2,2-difluoro-1,3-benzodioxol-5-yl)boronic acid

Conditions
ConditionsYield
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

Triisopropyl borate

sodium hydroxide
1310-73-2

sodium hydroxide

N-(n-butyl)-2-(2-bromophenyl)-benzimidazole
815581-69-2

N-(n-butyl)-2-(2-bromophenyl)-benzimidazole

2-(2-boronophenyl)-N-n-butylbenzimidazole sodium hydroxide salt

2-(2-boronophenyl)-N-n-butylbenzimidazole sodium hydroxide salt

Conditions
ConditionsYield
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

Triisopropyl borate

ethylene glycol
107-21-1

ethylene glycol

2-[(1,3,2-dioxaborolan-2-yloxy)diphenylmethyl]pyrrolidine

2-[(1,3,2-dioxaborolan-2-yloxy)diphenylmethyl]pyrrolidine

Conditions
ConditionsYield
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

Triisopropyl borate

1,1-diphenyl-L-valinol
78603-95-9

1,1-diphenyl-L-valinol

ethylene glycol
107-21-1

ethylene glycol

1-[([1,3,2]dioxaborolan-2-yloxy)-diphenyl-methyl]-2-methylpropylamine

1-[([1,3,2]dioxaborolan-2-yloxy)-diphenyl-methyl]-2-methylpropylamine

Conditions
ConditionsYield
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

Triisopropyl borate

(1R,2S)-norephedrine
492-41-1

(1R,2S)-norephedrine

ethylene glycol
107-21-1

ethylene glycol

(1R,2S)-1-(1',3',2'-dioxaborolan-2'-yloxy)-1-phenylpropan-2-amine

(1R,2S)-1-(1',3',2'-dioxaborolan-2'-yloxy)-1-phenylpropan-2-amine

Conditions
ConditionsYield
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

Triisopropyl borate

(R)-(+)-2-amino-1,1,2-triphenylethanol
60539-17-5, 79868-79-4, 129704-13-8

(R)-(+)-2-amino-1,1,2-triphenylethanol

ethylene glycol
107-21-1

ethylene glycol

(R)-(+)-2-(1,3,2-dioxaborolan-2-yloxy)-1,2,2-triphenylethanamine

(R)-(+)-2-(1,3,2-dioxaborolan-2-yloxy)-1,2,2-triphenylethanamine

Conditions
ConditionsYield
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

Triisopropyl borate

7-bromo-2H-pyrano[3,2-b]pyridine
1073633-66-5

7-bromo-2H-pyrano[3,2-b]pyridine

2H-pyrano[3,2-b]pyridin-7-ylboronic acid
1073633-67-6

2H-pyrano[3,2-b]pyridin-7-ylboronic acid

Conditions
ConditionsYield
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

2-bromo-pyridine

n-butyllithium
109-72-8, 29786-93-4

n-butyllithium

Triisopropyl borate
5419-55-6

Triisopropyl borate

lithium (pyridine-2-yl)triisopropoxyborate

lithium (pyridine-2-yl)triisopropoxyborate

Conditions
ConditionsYield
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

Triisopropyl borate

3-bromo-7,12-diphenylbenzo[k]fluoranthene
187086-32-4

3-bromo-7,12-diphenylbenzo[k]fluoranthene

7,12-diphenylbenzo[k]fluoranthen-3-ylboronic acid
276249-59-3

7,12-diphenylbenzo[k]fluoranthen-3-ylboronic acid

Conditions
ConditionsYield
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

Triisopropyl borate

3-Bromo-N-tert-butoxycarbonyl-N-methylaniline
57598-34-2

3-Bromo-N-tert-butoxycarbonyl-N-methylaniline

(3-((tert-butoxycarbonyl)(methyl)amino)phenyl)boronic acid
887831-90-5

(3-((tert-butoxycarbonyl)(methyl)amino)phenyl)boronic acid

Conditions
ConditionsYield
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

Triisopropyl borate

3-bromofluoranthene
13438-50-1

3-bromofluoranthene

7,12-diphenylbenzo[k]fluoranthene-3-boronic acid
359012-63-8

7,12-diphenylbenzo[k]fluoranthene-3-boronic acid

Conditions
ConditionsYield
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

n-butyllithium

2-bromo-4-methoxypyridine
89488-29-9

2-bromo-4-methoxypyridine

Triisopropyl borate
5419-55-6

Triisopropyl borate

lithium triisopropyl 2-(4-methoxypyridyl)borate

lithium triisopropyl 2-(4-methoxypyridyl)borate

Conditions
ConditionsYield
In tetrahydrofuran; toluene at -78 - 20℃; Inert atmosphere; Cooling with acetone-dry ice;100%
n-butyllithium
109-72-8, 29786-93-4

n-butyllithium

Triisopropyl borate
5419-55-6

Triisopropyl borate

2-bromo-4-chloropyridine
22918-01-0

2-bromo-4-chloropyridine

lithium triisopropyl 2-(4-chloropyridyl)borate

lithium triisopropyl 2-(4-chloropyridyl)borate

Conditions
ConditionsYield
In tetrahydrofuran; toluene at -78 - 20℃; Inert atmosphere; Cooling with acetone-dry ice;100%
Triisopropyl borate
5419-55-6

Triisopropyl borate

(S)-2-bromo-4-fluoro-1-(pent-4-en-2-yloxy)benzene

(S)-2-bromo-4-fluoro-1-(pent-4-en-2-yloxy)benzene

(S)-(5-fluoro-2-(pent-4-en-2-yloxy)phenyl)boronic acid

(S)-(5-fluoro-2-(pent-4-en-2-yloxy)phenyl)boronic acid

Conditions
ConditionsYield
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

Triisopropyl borate

(S)-5-bromo-2-(2-(trifluoromethyl)pyrrolidin-1-yl)pyrimidine
1620136-60-8

(S)-5-bromo-2-(2-(trifluoromethyl)pyrrolidin-1-yl)pyrimidine

(S)-(2-(2-(trifluoromethyl)pyrrolidin-1-yl)pyrimidin-5-yl)boronic acid

(S)-(2-(2-(trifluoromethyl)pyrrolidin-1-yl)pyrimidin-5-yl)boronic acid

Conditions
ConditionsYield
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

Triisopropyl borate

(S)-(-)-2-amino-1,1,3-triphenyl-1-propanol
79868-78-3

(S)-(-)-2-amino-1,1,3-triphenyl-1-propanol

ethylene glycol
107-21-1

ethylene glycol

C23H24BNO3

C23H24BNO3

Conditions
ConditionsYield
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

Triisopropyl borate

(S)-(-)-α,α-di(2-naphthyl)-2-pyrrolidinemethanol
130798-48-0, 127986-84-9

(S)-(-)-α,α-di(2-naphthyl)-2-pyrrolidinemethanol

ethylene glycol
107-21-1

ethylene glycol

C27H26BNO3

C27H26BNO3

Conditions
ConditionsYield
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

Triisopropyl borate

(R)-α,α-diphenylprolinol
22348-32-9

(R)-α,α-diphenylprolinol

ethylene glycol
107-21-1

ethylene glycol

(R)-2-[(1,3,2-dioxaborolan-2-yloxy)diphenylmethyl]pyrrolidine

(R)-2-[(1,3,2-dioxaborolan-2-yloxy)diphenylmethyl]pyrrolidine

Conditions
ConditionsYield
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

2,3-dimethyl-2,3-butane diol

Triisopropyl borate
5419-55-6

Triisopropyl borate

(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

(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
ConditionsYield
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

Triisopropyl borate

benzene-1,2-diol
120-80-9

benzene-1,2-diol

C23H22BNO3

C23H22BNO3

Conditions
ConditionsYield
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

Triisopropyl borate

ethylene glycol
107-21-1

ethylene glycol

N-[(1S,2S)-2-amino-1,2-diphenylethyl]-4-methylbenzenesulfonamide
167316-27-0

N-[(1S,2S)-2-amino-1,2-diphenylethyl]-4-methylbenzenesulfonamide

C23H25BN2O4S

C23H25BN2O4S

Conditions
ConditionsYield
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

Triisopropyl borate

(R)-(+)-α,α-di-(2-naphthyl)-2-pyrrolidinemethanol
130798-48-0

(R)-(+)-α,α-di-(2-naphthyl)-2-pyrrolidinemethanol

ethylene glycol
107-21-1

ethylene glycol

C27H26BNO3

C27H26BNO3

Conditions
ConditionsYield
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

Triisopropyl borate

2-bromobenzo[9,10]phenanthrene
19111-87-6

2-bromobenzo[9,10]phenanthrene

benzo[l]phenanthrene-2-boronic acid
654664-63-8

benzo[l]phenanthrene-2-boronic acid

Conditions
ConditionsYield
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

Triisopropyl borate

4-bromo-2-(dimethoxymethyl)pyridine

4-bromo-2-(dimethoxymethyl)pyridine

(2-(dimethoxymethyl)pyridin-4-yl)boric acid lithium salt

(2-(dimethoxymethyl)pyridin-4-yl)boric acid lithium salt

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; toluene at -78 - 20℃; Inert atmosphere;100%
Triisopropyl borate
5419-55-6

Triisopropyl borate

2-tert-butyl-4-iodo-1-(2-methoxy-ethoxymethoxy)-benzene

2-tert-butyl-4-iodo-1-(2-methoxy-ethoxymethoxy)-benzene

3-tert-butyl-4-(2-methoxy-ethoxymethoxy)-benzene boronic acid

3-tert-butyl-4-(2-methoxy-ethoxymethoxy)-benzene boronic acid

Conditions
ConditionsYield
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%

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