Conditions | Yield |
---|---|
at 130.0°C, 74.1 Torr equilibrium; | A 99.6% B 99.6% |
at 130.0°C, 74.1 Torr equilibrium; | A 99.6% B 99.6% |
at 54.8°C, 57.6 Torr equilibrium; | A 90.8% B 90.8% |
at 54.8°C, 57.6 Torr equilibrium; | A 90.8% B 90.8% |
Triisopropyl borate
methyllithium
B
trimethylborane
C
diisopropoxymethylborane
Conditions | Yield |
---|---|
With hydrogenchloride In diethyl ether under N2; to cold (-78 °C) soln. of boron compd. in Et2O slowly added MeLi, stirred for 0.5 h, warmed to room temp., stirred for 0.5 h,Li(BMe4) detected by (11)B NMR, cooled to 0 °C, added soln. of HCl in Et2O, stirred for 15 min, warmed; not isolated, monitored by (11)B NMR; | A 1% B <1 C 98% |
tri-sec-butylborate
methyllithium
B
CH3B(OCH(CH3)CH2CH3)2
C
trimethylborane
Conditions | Yield |
---|---|
With hydrogenchloride In diethyl ether under N2; to cold (-78 °C) soln. of boron compd. in Et2O slowly added MeLi, stirred for 0.5 h, warmed to room temp., stirred for 0.5 h,Li(BMe4) detected by (11)B NMR, cooled to 0 °C, added soln. of HCl in Et2O, stirred for 15 min, warmed; not isolated, monitored by (11)B NMR; | A 1% B 98% C <1 |
triisobutyl borate
methyllithium
B
CH3B(OCH2CH(CH3)2)2
C
trimethylborane
Conditions | Yield |
---|---|
With hydrogenchloride In diethyl ether under N2; to cold (-78 °C) soln. of boron compd. in Et2O slowly added MeLi, stirred for 0.5 h, warmed to room temp., stirred for 0.5 h,Li(BMe4) detected by (11)B NMR, cooled to 0 °C, added soln. of HCl in Et2O, stirred for 15 min, warmed; not isolated, monitored by (11)B NMR; | A 1% B 98% C <1 |
methyllithium
2,4,4,5,5-pentamethyl-[1,3,2]dioxaborolane
A
(CH3)2BOC(CH3)2C(CH3)2OH
B
trimethylborane
Conditions | Yield |
---|---|
With hydrogenchloride In diethyl ether byproducts: LiCl; 1 equiv of MeLi slowly adding to a soln. of the boronic ester at -78°C, stirring for 3 h at the same temp., 1 equiv of anhydrous HCl in Et2O adding, warming to room temp., stirring for 15 min; the content was detd. by (11)B NMR spectrum; | A 98% B <1 |
trimethyl-borane; compound with trimethylamine
A
trimethylborane
B
trimethylamine
Conditions | Yield |
---|---|
at 111.3°C, 64.5 Torr equilibrium; | A 96% B 96% |
at 111.3°C, 64.5 Torr equilibrium; | A 96% B 96% |
at 65.8°C, 47.5 Torr equilibrium; | A 63.8% B 63.8% |
Conditions | Yield |
---|---|
With hydrogenchloride In diethyl ether byproducts: LiCl, 2-propanol; 2 equiv of MeLi slowly adding to a soln. of the boronic ester at -78°C, stirring for 3 h at the same temp., 1 equiv of anhydrous HCl in Et2O adding, warming to room temp., stirring for 15 min; the content was detd. by (11)B NMR spectrum; | A 95% B <1 |
With hydrogenchloride In diethyl ether byproducts: LiCl, 2-propanol; 1 equiv of MeLi slowly adding to a soln. of the boronic ester at -78°C, stirring for 3 h at the same temp., 1 equiv of anhydrous HCl in Et2O adding, warming to room temp., stirring for 15 min; the content was detd. by (11)B NMR spectrum; | A 95% B <1 |
methyllithium
2-methyl-[1,3,2]dioxaborinane
A
(CH3)2BO(CH2)3OH
B
trimethylborane
Conditions | Yield |
---|---|
With hydrogenchloride In diethyl ether byproducts: LiCl; 2 equiv of MeLi slowly adding to a soln. of the boronic ester at -78°C, stirring for 3 h at the same temp., 1 equiv of anhydrous HCl in Et2O adding, warming to room temp., stirring for 15 min; the content was detd. by (11)B NMR spectrum; | A 92% B <7 |
bis[tert-butyl(dimethylboryl)amino]methylphosphanoxide
A
trimethylborane
B
1,3-di-tert-butyl-2,4-dimethyl-1,3,2,4-diazaphosphaboretidine-2-oxide
Conditions | Yield |
---|---|
In neat (no solvent) heating at 160-170°C for 5 h in a stream of N2 with condensationof the volatiles in a trap cooled at -78°C;; distn.; elem. anal.;; | A 88% B 75% |
Conditions | Yield |
---|---|
In diethyl ether at room temp. for 2 h, molar ratio BCl3:ether:MeMgBr01:2:3; by fractional condensation; | 87% |
In diethyl ether at room temp. for 2 h, molar ratio BCl3:ether:MeMgBr01:2:3; by fractional condensation; | 87% |
dimethylboron bromide
bis(tert-butylamino)dimethylsilane
A
trimethylborane
B
1,3-di-tert-butyl-2,2,4-trimethyl-1,3,2,4-diazasilaboretidine
Conditions | Yield |
---|---|
With n-butyllithium In hexane; cyclohexane under N2 atmosphere; lithiation of the amine with n-BuLi in hexane; refluxing for 20 h; dropwise addn. of a soln. of B compd. in cyclohexane tothe suspn. of the Li compd. at -78°; slow warming to room temp.;; filtration; removal of volatiles from filtrate; fractional distn.; elem. anal.;; | A 83.5% B 67% |
boric acid tributyl ester
methyllithium
B
trimethylborane
C
methyldi-n-butoxyborane
Conditions | Yield |
---|---|
With hydrogenchloride In diethyl ether under N2; to cold (-78 °C) soln. of boron compd. in Et2O slowly added MeLi, stirred for 0.5 h, warmed to room temp., stirred for 0.5 h,Li(BMe4) detected by (11)B NMR, cooled to 0 °C, added soln. of HCl in Et2O, stirred for 15 min, warmed; not isolated, monitored by (11)B NMR; | A 9% B <1 C 82% |
trimethyl-borane; compound with methylamine
A
trimethylborane
B
methylamine
Conditions | Yield |
---|---|
at 130.0°C, 77.4 Torr equilibrium; | A 81.95% B 81.95% |
at 130.0°C, 77.4 Torr equilibrium; | A 81.95% B 81.95% |
at 85.4°C, 52.5 Torr equilibrium; | A 38.86% B 38.86% |
at 85.4°C, 52.5 Torr equilibrium; | A 38.86% B 38.86% |
Conditions | Yield |
---|---|
In diethyl ether | 80% |
In diethyl ether | 80% |
In benzene | |
In benzene |
2,8-dibromo-3,4,6,7-tetrathia-1-aza-2,5,8-triborabicyclo{3.3.0(1,5)}octane
bis(dimethylboryl)disulphane
A
9-methyl-2,3,5,6,8,10-hexathia-11-aza-1,4,7,9-tetraboratricyclo{6.2.1.0(1,11)}undecane
B
trimethylborane
C
dimethylboron bromide
D
3,5-dimethyl-1,2,4-trithia-3,5-diborolane
Conditions | Yield |
---|---|
In toluene N2 atmosphere; addn. of soln. of (Me2BS)2 to soln. of BN(BBr2)2 (room temp., stirring), heating (70°C, 36 h); sepn. of solid, removal of volatiles, sepn. of educt (sublimation, 110°C, 1.3 Pa); elem. anal.; | A 76% B n/a C n/a D n/a |
trimethyl-borane; compound with dimethylamine
A
trimethylborane
B
dimethyl amine
Conditions | Yield |
---|---|
at 125.6°C, 66.3 Torr equilibrium; | A 74.2% B 74.2% |
at 125.6°C, 66.3 Torr equilibrium; | A 74.2% B 74.2% |
at 85.1°C, 45 Torr equilibrium; | A 31.6% B 31.6% |
at 85.1°C, 45 Torr equilibrium; | A 31.6% B 31.6% |
Triisopropyl borate
Trimethylboroxine
A
trimethylborane
B
diisopropoxymethylborane
Conditions | Yield |
---|---|
In tetrahydrofuran | A n/a B 70% |
triethyl borate
methyllithium
A
diethoxymethylborane
B
trimethylborane
C
Dimethan-borinsaeure-ethylester
Conditions | Yield |
---|---|
With hydrogenchloride In diethyl ether under N2; to cold (-78 °C) soln. of boron compd. in Et2O slowly added MeLi, stirred for 0.5 h, warmed to room temp., stirred for 0.5 h,Li(BMe4) detected by (11)B NMR, cooled to 0 °C, added soln. of HCl in Et2O, stirred for 15 min, warmed; not isolated, monitored by (11)B NMR; | A 65% B 7% C 10% |
CH3B(O-t-C4H9)2
methyllithium
A
trimethylborane
B
Dimethylborinsaeure-tert.-butylester
Conditions | Yield |
---|---|
With hydrogenchloride In diethyl ether byproducts: LiCl, 2-propanol; 1 equiv of MeLi slowly adding to a soln. of the boronic ester at -78°C, stirring for 3 h at the same temp., 1 equiv of anhydrous HCl in Et2O adding, allowing to warm to room temp., stirring for 15 min; the content was detd. by (11)B NMR spectrum; | A 32% B 58% |
tetramethyl diborane
ethene
A
trimethylborane
B
(dimethyl)trifluoropropylborane
C
Methyl-bis-<3,3,3-trifluor-propyl>-boran
Conditions | Yield |
---|---|
A 30% B 45% C 8% | |
A 30% B 45% C 8% |
chlorodimethoxyborane
methyllithium
A
trimethylborane
B
methoxy-dimethyl-borane
C
bis(methoxy)methylborane
Conditions | Yield |
---|---|
With hydrogenchloride In diethyl ether under N2; to cold (-78 °C) soln. of boron compd. in Et2O slowly added MeLi, stirred for 0.5 h, warmed to room temp., stirred for 0.5 h,Li(BMe4) detected by (11)B NMR, cooled to 0 °C, added soln. of HCl in Et2O, stirred for 15 min, warmed; not isolated, monitored by (11)B NMR; | A 16% B 6% C 43% |
Conditions | Yield |
---|---|
With hydrogenchloride In diethyl ether under N2; to cold (-78 °C) soln. of boron compd. in Et2O slowly added MeLi, stirred for 0.5 h, warmed to room temp., stirred for 0.5 h,Li(BMe4) detected by (11)B NMR, cooled to 0 °C, added soln. of HCl in Et2O, stirred for 15 min, warmed; not isolated, monitored by (11)B NMR; | A 25% B 42% C 4% |
Conditions | Yield |
---|---|
In neat (no solvent) (exclusion of moisture); room temp., 16 h; purifn. by trap-to-trap distn.; | A n/a B n/a C 40% |
Conditions | Yield |
---|---|
In mineral oil B(OCH3)3 condensed onto Al(CH3)3 soln. with -196°C trap, opened to closed vol., warmed slowly to room temp. with stirring, repeated twice; pumped into -196°C trap, passed through -132°C into -196°C trap; | 38% |
tetramethyl diborane
ethene
A
trimethylborane
B
dimethylethylborane
C
triethyl borane
D
methyldiethylborane
Conditions | Yield |
---|---|
A 25% B 34% C 0.5% D 19% | |
A 25% B 34% C 0.5% D 19% |
dimethylboron bromide
1,1,1,3,3,3-hexamethyl-disilazane
A
trimethylborane
B
2,4,6-Trimethyl-[1,3,5,2,4,6]triazatriborinane
C
bis(dimethylboryl)methylamine
Conditions | Yield |
---|---|
byproducts: (CH3)3SiBr; 50°C, 20 h, in closed tube; | A n/a B n/a C 34% |
methyllithium
boron trichloride
A
trimethylborane
B
methoxy-dimethyl-borane
C
bis(methoxy)methylborane
Conditions | Yield |
---|---|
With hydrogenchloride In diethyl ether under N2; to cold (-78 °C) soln. of boron compd. in Et2O slowly added MeLi, stirred for 0.5 h, warmed to room temp., stirred for 0.5 h,Li(BMe4) detected by (11)B NMR, cooled to 0 °C, added soln. of HCl in Et2O, stirred for 15 min, warmed; not isolated, monitored by (11)B NMR; | A 32% B 3% C <1 |
2-bromo-1,3,2-benzodioxaborole
methyllithium
A
(CH3)2BOC6H4OH
B
trimethylborane
Conditions | Yield |
---|---|
With hydrogenchloride In diethyl ether byproducts: LiCl; 1 equiv of MeLi slowly adding to a soln. of the boronic ester at -78°C, stirring for 3 h at the same temp., 1 equiv of anhydrous HCl in Et2O adding, warming to room temp., stirring for 15 min; the content was detd. by (11)B NMR spectrum; | A 20% B 30% |
fluorodimethoxyborane
methyllithium
A
trimethylborane
B
methoxy-dimethyl-borane
C
bis(methoxy)methylborane
Conditions | Yield |
---|---|
With hydrogenchloride In diethyl ether under N2; to cold (-78 °C) soln. of boron compd. in Et2O slowly added MeLi, stirred for 0.5 h, warmed to room temp., stirred for 0.5 h,Li(BMe4) detected by (11)B NMR, cooled to 0 °C, added soln. of HCl in Et2O, stirred for 15 min, warmed; not isolated, monitored by (11)B NMR; | A 28% B <1 C 10% |
methyllithium
2-methyl-1,3,2-dioxaborolane
A
(CH3)2BO(CH2)2OH
B
trimethylborane
Conditions | Yield |
---|---|
With hydrogenchloride In diethyl ether byproducts: LiCl; 1 equiv of MeLi slowly adding to a soln. of the boronic ester at -78°C, stirring for 3 h at the same temp., 1 equiv of anhydrous HCl in Et2O adding, warming to room temp., stirring for 15 min; the content was detd. by (11)B NMR spectrum; | A 21% B 26% |
Conditions | Yield |
---|---|
In tetrahydrofuran (Ar); warming from -78°C to room temp. (10 h); evapn.; elem. anal.; | 99% |
trimethylborane
(tert-butylimino)(2,2,6,6-tetramethylpiperidino)borane
Conditions | Yield |
---|---|
In hexane | 97% |
In hexane Schlenk technique, a soln. of iminoborane frozen at -196°C, borancondenced onto it, allowed to slowly thaw, stirred for 4 h; solvent removed (50 Torr); elem. anal.; | 97% |
Conditions | Yield |
---|---|
In neat (no solvent) synthesis of small amounts: condensation of 0.061 mol B(CH3)3 onto 0.061mol B2O3 (-192 °C), heating in a sealed tube at 300°C for 6h;; condensation in vac. into a trap at -78°C;; | 96% |
In neat (no solvent) synthesis of small amounts: condensation of 0.061 mol B(CH3)3 onto 0.061mol B2O3 (-192 °C), heating in a sealed tube at 300°C for 6h;; condensation in vac. into a trap at -78°C;; | 96% |
trimethylborane
dichloroborane
boron trichloride
dichloro-methyl-borane
Conditions | Yield |
---|---|
at ambient temp. 24 h in presence of 1 vol.% HBCl2; | 95% |
at ambient temp. 24 h in presence of 1 vol.% HBCl2; | 95% |
trimethylborane
(S,S)-(-)-1,2-dicyclohexyl-ethane-1,2-diol
Conditions | Yield |
---|---|
In neat (no solvent) byproducts: methanol; Ar-atmosphere; stirring; distg.; | 95% |
Conditions | Yield |
---|---|
With alkene; tetraethyldiborane(6) react. of two equiv B(CH3)3 with one equiv BBr3 at room temp., decompn. of catalyst with alkene; distn.; | 91% |
tetraethyldiborane(6) |
trimethylborane
3,3-diphenylboratrane
Conditions | Yield |
---|---|
In chloroform (Ar), Me3B added to soln. of ligand in CHCl3, stirred for 24 h at room temp.; fconcd.(vac.), pptd.(pentane), filtered, washed (pentane), dried (vac.); | 90% |
2,3-dimethyl-2,3-butane diol
trimethylborane
1,5-anhydro-2-deoxy-4,6-O-bis(tert-butylsilylidene)-3-O-triisopropylsilyl-D-arabino-hex-1-enitol
(1,5-anhydro-2-deoxy-4,6-O-bis(tert-butylsilylidene)-3-O-triisopropylsilyl-D-arabino-hex-1-enitol)boronic acid pinacol ester
Conditions | Yield |
---|---|
Stage #1: 1,5-anhydro-2-deoxy-4,6-O-bis(tert-butylsilylidene)-3-O-triisopropylsilyl-D-arabino-hex-1-enitol With n-butyllithium In tetrahydrofuran; hexane at -78 - 0℃; Inert atmosphere; Large scale; Stage #2: trimethylborane In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Large scale; Stage #3: 2,3-dimethyl-2,3-butane diol In toluene at 20℃; for 12h; Large scale; | 90% |
trimethylborane
methyl 4-hydroxy-1-chloro-7-phenoxyisoquinoline-3-carboxylate
1-methyl-4-hydroxy-7-phenoxyisoquinoline-3-carboxylic acid
Conditions | Yield |
---|---|
Stage #1: trimethylborane; methyl 4-hydroxy-1-chloro-7-phenoxyisoquinoline-3-carboxylate With bis-triphenylphosphine-palladium(II) chloride; sodium phosphate In 2-methoxy-ethanol; water at 90 - 100℃; for 4h; Stage #2: With hydrogenchloride In water at 20 - 30℃; pH=2 - 3; | 88% |
trimethylborane
trimethylsilyllithium
Li(1+)*B(Si(CH3)3)(CH3)3(1-)=Li{B(Si(CH3)3)(CH3)3}
Conditions | Yield |
---|---|
In hexane at -196°C in high vac., pptn. during warming up; the solvent was decanted, the product was washed with pentane, then dissolved in benzene and crystd. with pentane; elem. anal.; | 86% |
trimethylborane
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); water; potassium carbonate In ethanol at 110℃; for 4h; | 86% |
dodecacarbonyl-triangulo-triruthenium
trimethylborane
K(1+)*HRu3(CO)11(1-)=KHRu3(CO)11
Conditions | Yield |
---|---|
In tetrahydrofuran byproducts: CO; distg. of THF onto mixt. of Ru3(CO)12 and KH at -78°C in inert atmosphere, distg. of B(CH3)3 at -196°C, warming to 25°C, CO evolves, the soln. turns bright red; evapn. in vac. after 2 h, dissolving in min. amt. of CH2Cl2, addn. of hexane, filtn., washing (hexane); | 83% |
trimethylborane
Conditions | Yield |
---|---|
In chloroform (Ar), Me3B added to soln. of ligand in CHCl3, stirred for 24 h at room temp.; filtered, washed (CHCl3), dried (vac.); | 82% |
trimethylborane
1-phenyl-2-methylpropane
Ethyl oxalyl chloride
ibuprofen
Conditions | Yield |
---|---|
Stage #1: 1-phenyl-2-methylpropane; Ethyl oxalyl chloride With aluminum (III) chloride Stage #2: trimethylborane With phosphorous acid trimethyl ester Stage #3: With lithium hydroxide | 82% |
Conditions | Yield |
---|---|
byproducts: (CH3)3B*P(CH3)3; in 77 day; | 78% |
byproducts: (CH3)3B*P(CH3)3; in 77 day; | 78% |
2,3-dimethyl-2,3-butane diol
trimethylborane
diisopropylamine
1,2-dibromomethane
2-(dibromomethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Conditions | Yield |
---|---|
With n-butyllithium; hydrogen bromide In tetrahydrofuran; diethyl ether; hexane (i-Pr)2NH in ether mixed with n-BuLi in n-hexane at 0°C, THF added, cooled to -100°C, CH2Br2 in THF added under stirring over 1 h, kept for 30 min at this temp., BMe3 added, after 40 min aq. HBr added at -100°C, warmed to room temp.; filtered, washed (ether), concd., residue taked up (ether), Me2C(OH)C(OH)Me2 added, petroleum ether added, stirred for 1 h, org. phase separated and washed (H2O, 4 times), dried (Na2SO4), concd., distilled at 0.5 Torr (100-110°C); elem. anal.; | 77% |
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