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% |
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% |
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% |
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% |
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
isopropyl alcohol
Triisopropyl borate
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
isopropyl alcohol
Triisopropyl borate
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% |
Conditions | Yield |
---|---|
With boric acid; benzene unter Entfernen des entstehenden Wassers; | |
With boron trioxide at 130℃; | |
With boron trioxide; toluene |
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; |
Conditions | Yield |
---|---|
90°C, bomb tube; | |
90°C, bomb tube; |
chloro-trimethyl-silane
Hexamethyldisiloxane
boric acid
isopropyl alcohol
C
Triisopropyl borate
D
tris(trimethylsilyl)borate
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; |
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; |
Conditions | Yield |
---|---|
lithium triethylborohydride In tetrahydrofuran byproducts: H2; at 20°C with and without catalyst; |
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
Triisopropyl borate
Conditions | Yield |
---|---|
With isopropanol In benzene byproducts: water; distilled out at 138-140°C, elem. anal.;; |
Conditions | Yield |
---|---|
In tetrahydrofuran potassium tetraisopropoxyborohydride refluxed in THF for 18 h; cooled to room temp., not isolated, detected by NMR; |
allylboronic acid
isopropyl alcohol
A
Triisopropyl borate
B
diisopropyl allylboronate
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
(E)-1-hexenyldiisopropoxyborane
A
diethyl(isopropoxy)borane
B
Triisopropyl borate
C
ethyl-1-hexenylisopropoxyborane
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
(E)-1-hexenyldiisopropoxyborane
A
Triisopropyl borate
B
ethyl-1-hexenylisopropoxyborane
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
(E)-1-hexenyldiisopropoxyborane
A
Triisopropyl borate
C
isopropyl-1-hexenylisopropoxyborane
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
(E)-1-hexenyldiisopropoxyborane
A
Triisopropyl borate
B
isobutyl-1-hexenylisopropoxyborane
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
(E)-1-hexenyldiisopropoxyborane
B
Triisopropyl borate
D
methyl-1-hexenylisopropoxyborane
E
diisopropoxymethylborane
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
(E)-1-hexenyldiisopropoxyborane
B
Triisopropyl borate
C
methyl-1-hexenylisopropoxyborane
D
diisopropoxymethylborane
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;; |
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; |
C8H14BClS(CH3)2
A
Triisopropyl borate
B
potassium (cyclooctane-1,5-diyl)dihydroborate
Conditions | Yield |
---|---|
In tetrahydrofuran 2 equivalent K(i-PrO)3BH, 25°C, 0.25 h; detected by 11B NMR; |
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; |
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
tert-Butyldimethyl(prop-2-ynyloxy)silane
Conditions | Yield |
---|---|
With n-butyllithium In diethyl ether at 20℃; Substitution; | 100% |
Conditions | Yield |
---|---|
With n-butyllithium In diethyl ether at 20℃; Substitution; | 100% |
Triisopropyl borate
pinanediol
(3aS,4s,6S,7aR)-hexahydro-3a,5,5-trimethyl-2-(1-methylethoxy)-4,6-methano-1,3,2-benzodioxaborole
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
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
Triisopropyl borate
(2,2-difluoro-1,3-benzodioxol-5-yl)boronic acid
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
sodium hydroxide
N-(n-butyl)-2-(2-bromophenyl)-benzimidazole
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
(S)-diphenylprolinol
ethylene glycol
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; |
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% |
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
(R)-(+)-2-amino-1,1,2-triphenylethanol
ethylene glycol
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
7-bromo-2H-pyrano[3,2-b]pyridine
2H-pyrano[3,2-b]pyridin-7-ylboronic acid
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% |
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
3-bromo-7,12-diphenylbenzo[k]fluoranthene
7,12-diphenylbenzo[k]fluoranthen-3-ylboronic acid
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
3-Bromo-N-tert-butoxycarbonyl-N-methylaniline
(3-((tert-butoxycarbonyl)(methyl)amino)phenyl)boronic acid
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
3-bromofluoranthene
7,12-diphenylbenzo[k]fluoranthene-3-boronic acid
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
2-bromo-4-methoxypyridine
Triisopropyl borate
Conditions | Yield |
---|---|
In tetrahydrofuran; toluene at -78 - 20℃; Inert atmosphere; Cooling with acetone-dry ice; | 100% |
n-butyllithium
Triisopropyl borate
2-bromo-4-chloropyridine
Conditions | Yield |
---|---|
In tetrahydrofuran; toluene at -78 - 20℃; Inert atmosphere; Cooling with acetone-dry ice; | 100% |
Triisopropyl borate
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
(S)-5-bromo-2-(2-(trifluoromethyl)pyrrolidin-1-yl)pyrimidine
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
(S)-(-)-2-amino-1,1,3-triphenyl-1-propanol
ethylene glycol
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
(S)-(-)-α,α-di(2-naphthyl)-2-pyrrolidinemethanol
ethylene glycol
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% |
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
Triisopropyl borate
(S)-diphenylprolinol
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
(S)-diphenylprolinol
benzene-1,2-diol
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
ethylene glycol
N-[(1S,2S)-2-amino-1,2-diphenylethyl]-4-methylbenzenesulfonamide
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
(R)-(+)-α,α-di-(2-naphthyl)-2-pyrrolidinemethanol
ethylene glycol
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
2-bromobenzo[9,10]phenanthrene
benzo[l]phenanthrene-2-boronic acid
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
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran; toluene at -78 - 20℃; Inert atmosphere; | 100% |
Triisopropyl borate
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% |
The IUPAC name of Isopropyl borate is tripropan-2-yl borate. With the CAS registry number 5419-55-6, it is also named as 4-01-00-01488 (Beilstein Handbook Reference); AI3-61082; BRN 1701469; Boric acid, triisopropyl ester; Triisopropoxy borane; Boric acid, tris(1-methylethyl) ester. The product's categories are B (classes of boron compounds), boric acid esters and boric acid triesters.
The Isopropyl borate is clear colourless liquid which is sensitive to moisture. It can be used to make other chemicals. And it is also used as a solvent and the diffusion source of semiconductor boron. Borates, such as Isopropyl 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.
This chemical is highly flammable. So it must be kept away from sources of ignition. In addition, people should not breathe vapour and avoid contact with skin and eyes. Take precautionary measures against static discharges. Keep container tightly closed and keep container in a well-ventilated place.
The other characteristics of this product can be summarized as: (1)ACD/LogP: 4.09; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 4.09; (4)ACD/LogD (pH 7.4): 4.09; (5)ACD/BCF (pH 5.5): 751.54; (6)ACD/BCF (pH 7.4): 751.54; (7)ACD/KOC (pH 5.5): 3982.98; (8)ACD/KOC (pH 7.4): 3982.98; (9)#H bond acceptors: 3; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 6; (12)Index of Refraction: 1.392; (13)Molar Refractivity: 52.28 cm3; (14)Molar Volume: 219.2 cm3; (15)Polarizability: 20.72×10-24 cm3; (16)Surface Tension: 22.6 dyne/cm; (17)Enthalpy of Vaporization: 36.17 kJ/mol; (18)Vapour Pressure: 7.8 mmHg at 25°C; (19)Rotatable Bond Count: 6; (20)Exact Mass: 188.158375; (21)MonoIsotopic Mass: 188.158375; (22)Topological Polar Surface Area: 27.7; (23)Heavy Atom Count: 13.
People can use the following data to convert to the molecule structure. SMILES: O(B(OC(C)C)OC(C)C)C(C)C; InChI: InChI=1/C9H21BO3/c1-7(2)11-10(12-8(3)4)13-9(5)6/h7-9H,1-6H3; InChIKey: NHDIQVFFNDKAQU-UHFFFAOYAX. Isopropyl borate has many suppliers, such as Chemik Co., Ltd., Jiangsu Wisdom Pharmaceutical Co., Ltd. and Nanjing Wisdompharm Chemical Co., Ltd..
The following is the toxicity data which has been tested.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intravenous | 100mg/kg (100mg/kg) | U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#00382, | |
mouse | LD50 | oral | 2500mg/kg (2500mg/kg) | "Boron, Metallo-Boron Compounds and Boranes," Adams, R.M., ed., New York, John Wiley & Sons, Inc., 1964Vol. -, Pg. 693, 1964. |
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