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inquiry9-Borabicyclo[3.3.1]nonane Basic information Product Name: 9-Borabicyclo[3.3.1]nonane Synonyms: 9-BBN;9-BORABICYCLO[3.3.1]NONANE;9-borabicyclo[3.3.1]nonane,9-bbn,inhexanes;9-borabicyclo[
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inquiry9-Borabicyclo[3.3.1]nonaneAppearance:Colorless to light yellow liquid Storage:Room Temperature Package:according to customers' requirements Application:API, Drug intermedias, CRO/CMO Transportation:By air(EMS or EUB or FedEx or TNT ect...) or by sea(
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inquiryProduct Name: 9-Borabicyclo[3.3.1]nonane Synonyms: 9-Borabicyclo[3.3.1]nonane, 0.5 M solution in THF, J&KSeal;9-BBN, 0.4M SOLUTION IN HEXANES;9-BORABICYCLO(3.3.1)NONANE SOLUTION, ~0. 5 M IN THF;9-Borabicyclo[3.3.1]nonane, 0.5M solution in T
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inquiry1,5-cis,cis-cyclooctadiene
9-bora-bicyclo[3.3.1]nonane
Conditions | Yield |
---|---|
With borane N-ethyl-N-isopropylaniline complex In 1,4-dioxane hydroboration; Heating; | 87% |
With dimethylsulfide borane complex In tetrahydrofuran at -5 - 67℃; for 1.75h; |
borane-THF
9-(di-tert-butylphosphanyl)-9-bora{3.3.1}bicyclononane
A
μ-(di-tert-butylphosphanyl)-diborane
B
1,1,3,3-tetra-tert-butyl-1,3,2,4-diphosphadiboracyclobutane
C
μ-(di-tert-butylphosphanyl)-di-9-bora{3.3.1}bicyclononane
D
9-bora-bicyclo[3.3.1]nonane
Conditions | Yield |
---|---|
In tetrahydrofuran dropping soln. of BH3*THF in THF to soln. of borane in THF at -78°C, under N2 or Ar; refluxing for 1 h; mechansim discussed;; removal of solvent in vac.; recrystn. from ether; 1. and 2. fraction product mixts., 3. fraction pure 9-borabicyclo(3.3.1)nonane, 4. fraction small amt. of pure (BH2P(tert-butyl)2)2; detn. by NMR;; | A n/a B n/a C n/a D 75% |
1,5-dicyclooctadiene
9-bora-bicyclo[3.3.1]nonane
Conditions | Yield |
---|---|
In 1,4-dioxane N2-atmosphere; dropwise cyclooctadiene addn. (20°C, stirring), stirring (room temp, 3 h, refluxing , 2 h); crystn. (room temp.), decanting, washing (n-pentane), drying (reduced pressure), recrystn. (THF); | 70% |
1,5-cis,cis-cyclooctadiene
A
9-BBN
B
9-bora-bicyclo[3.3.1]nonane
Conditions | Yield |
---|---|
With borane N-ethyl-N-isopropylaniline complex In 1,4-dioxane at 20℃; for 1h; hydroboration; Title compound not separated from byproducts; |
9-chloro-9-borabicyclo{3.3.1}nonane
B
9-methyl-9-borabicyclo[3.3.1]nonane
C
9-bora-bicyclo[3.3.1]nonane
Conditions | Yield |
---|---|
In diethyl ether; toluene Title compound not separated from byproducts.; |
9-borabicyclo[3.3.1]nonane dimer
9-bora-bicyclo[3.3.1]nonane
Conditions | Yield |
---|---|
With acetophenone In tetrahydrofuran Kinetics; 25°C; detected by IR; | |
With pivalaldehyde In tetrahydrofuran Kinetics; 25°C; detected by IR; | |
With 2,4-dimethylpentan-3-one In tetrahydrofuran Kinetics; 25°C; detected by IR; |
C8H14BBrS(CH3)2
9-bora-bicyclo[3.3.1]nonane
Conditions | Yield |
---|---|
With Li(t-BuO)3AlH In tetrahydrofuran byproducts: B-alkoxy-9-borabicyclo-[3.3.1]nonane; 0°C, 0.25 h; detected by 11B NMR; | |
With LiAlH4 In tetrahydrofuran byproducts: AlBr3, LiBr; 0.25 equivalent LiAlH4, 0°C, 0.25 h; detected by 11B NMR; |
C8H14BBrS(CH3)2
A
dimethylsulfide borane complex
B
9-bora-bicyclo[3.3.1]nonane
Conditions | Yield |
---|---|
In tetrahydrofuran byproducts: LiBr; 0°C, 0.25 h; detected 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; |
C8H14BBrS(CH3)2
9-bora-bicyclo[3.3.1]nonane
Conditions | Yield |
---|---|
In tetrahydrofuran 0°C, 0.25 h; detected by 11B NMR; |
C8H14BClS(CH3)2
9-bora-bicyclo[3.3.1]nonane
Conditions | Yield |
---|---|
With Li(CH3O)3AlH In tetrahydrofuran byproducts: B-alkoxy-9-borabicyclo[3.3.1]nonane; 0°C, 0.25 h; detected by 11B NMR; | |
With LiAlH4 In tetrahydrofuran byproducts: AlCl3, LiCl; 0.25 equivalent LiAlH4, 0°C, 0.25 h; detected by 11B NMR; |
C8H14BClS(CH3)2
lithium triethylborohydride
B
9-bora-bicyclo[3.3.1]nonane
Conditions | Yield |
---|---|
In tetrahydrofuran byproducts: B-alkoxy-9-borabicyclo[3.3.1]nonane, (C2H5)3B; 0°C, 0.25 h; detected by 11B NMR; |
Conditions | Yield |
---|---|
In tetrahydrofuran byproducts: LiCl, BH3S(CH3)2; 0°C, 0.25 h; detected by 11B NMR; |
Conditions | Yield |
---|---|
In diethylene glycol dimethyl ether byproducts: NaCl, BH3S(CH3)2; 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; |
C8H14BClS(CH3)2
9-bora-bicyclo[3.3.1]nonane
Conditions | Yield |
---|---|
In tetrahydrofuran 0°C, 0.25 h; detected by 11B NMR; |
tetrakis(dimethylamido)zirconium (IV)
[C8BH14]2C10H6(NH)2
B
9-bora-bicyclo[3.3.1]nonane
Conditions | Yield |
---|---|
In not given byproducts: (CH3)2N; |
[C8BH14]2C10H6(NH)2
B
9-bora-bicyclo[3.3.1]nonane
Conditions | Yield |
---|---|
In not given byproducts: (CH3)2N; |
dimethylsulfide borane complex
1,5-dicyclooctadiene
9-bora-bicyclo[3.3.1]nonane
Conditions | Yield |
---|---|
In 1,2-dimethoxyethane at 20 - 60℃; |
Conditions | Yield |
---|---|
In (2)H8-toluene at 22℃; Equilibrium constant; |
9-borabicyclo[3.3.1]nonane dimer
fluorocyclohexane
A
B-cyclohexyl-9-borabicyclo<3.3.1>nonane
B
9-fluoro-9-boracyclo{3.3.1}nonane
C
9-bora-bicyclo[3.3.1]nonane
Conditions | Yield |
---|---|
In dichloromethane-d2 for 24h; Inert atmosphere; Glovebox; Sealed tube; |
1,5-Hexadien
9-bora-bicyclo[3.3.1]nonane
9,9'-hexane-1,6-diyl-bis-9-bora-bicyclo[3.3.1]nonane
Conditions | Yield |
---|---|
In tetrahydrofuran at 40℃; for 24h; Schlenk technique; Inert atmosphere; | 100% |
In tetrahydrofuran at 20℃; for 3h; Addition; | |
In tetrahydrofuran at 20℃; for 4.5h; Addition; Hydroboration; | |
In tetrahydrofuran at 20℃; for 3h; |
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; | 100% |
In tetrahydrofuran; hexane Yield given; |
9-bora-bicyclo[3.3.1]nonane
Conditions | Yield |
---|---|
With KH activated aith LiAlH4 In tetrahydrofuran at 25℃; for 0.5h; | 100% |
Conditions | Yield |
---|---|
In tetrahydrofuran; hexane at 20℃; | 100% |
Conditions | Yield |
---|---|
In tetrahydrofuran; hexane at 20℃; | 100% |
Conditions | Yield |
---|---|
In tetrahydrofuran; hexane at 20℃; | 100% |
1-hexene
9-bora-bicyclo[3.3.1]nonane
9-hexyl-9-borabicyclo[3.3.1]nonane
Conditions | Yield |
---|---|
In tetrahydrofuran at 60℃; for 12h; Schlenk technique; Inert atmosphere; | 100% |
In tetrahydrofuran at 25℃; for 24h; Schlenk technique; Inert atmosphere; | 100% |
In tetrahydrofuran at 20℃; for 2h; | 87% |
2,5-diallylpyrrole
9-bora-bicyclo[3.3.1]nonane
2,5-bis-[3'-(9''-borabicyclo[3.3.1]nonyl)propyl]pyrrole
Conditions | Yield |
---|---|
In tetrahydrofuran N2-atmosphere; dropwise addn. of 2 equiv. of B-compd. to pyrrole derivative, stirring (room temp., 15 h); solvent removal (vac.), distn.; | 100% |
7a-aza-7,7-dimethyl-6,7-dihydro-7-stanna-7aH-indene
9-bora-bicyclo[3.3.1]nonane
N-borabicyclo[3.3.1]nonyl-2(prop-(Z)-1-enyl-3'-dimethylstannyl)pyrrole
Conditions | Yield |
---|---|
In tetrahydrofuran N2-atmosphere; stirring equimolar amts. (room temp., 15 h); solvent removal; | 100% |
ethynyl[dimethyl(vinyl)silylethynyl]dimethylsilane
9-bora-bicyclo[3.3.1]nonane
4-(9-borabicyclo[3.3.1]non-9-yl)-1,1,6,6-tetramethyl-1H,2H,3H,6H-1,6-disilapentalene
Conditions | Yield |
---|---|
at 90 - 110℃; Inert atmosphere; regioselective reaction; | 100% |
In toluene (Ar), soln. of silane in toluene treated with equimolar amounts of 9-borabicyclo(3.3.1)nonane in one portion, heated up to 90-110°C for 2-5 min; evapd.(vac.); | |
In benzene (Ar), soln. of silane in benzene treated with equimolar amounts of 9-borabicyclo(3.3.1)nonane in one portion, heated up to 90-110°C for 2-5 min; evapd.(vac.); |
1-(3-dimethylamino)propynyl[dimethyl(vinyl)silylethynyl]dimethylsilane
9-bora-bicyclo[3.3.1]nonane
4-(9-borabicyclo[3.3.1]non-9-yl)-5-[(dimethylamino)methyl]-1,1,6,6-tetramethyl-1H,2H,3H,6H-1,6-disilapentalene
Conditions | Yield |
---|---|
at 90 - 110℃; Inert atmosphere; regioselective reaction; | 100% |
In toluene (Ar), soln. of silane in toluene treated with equimolar amounts of 9-borabicyclo(3.3.1)nonane in one portion, heated up to 90-110°C for 2-5 min; evapd.(vac.); elem. anal.; | |
In benzene (Ar), soln. of silane in benzene treated with equimolar amounts of 9-borabicyclo(3.3.1)nonane in one portion, heated up to 90-110°C for 2-5 min; evapd.(vac.); elem. anal.; |
dimethyl(vinyl)silylethynyl(phenylethynyl)dimethylsilane
9-bora-bicyclo[3.3.1]nonane
4-(9-borabicyclo[3.3.1]non-9-yl)-1,1,6,6-tetramethyl-5-phenyl-1H,2H,3H,6H-1,6-disilapentalene
Conditions | Yield |
---|---|
at 90 - 110℃; Inert atmosphere; regioselective reaction; | 100% |
In toluene (Ar), soln. of silane in toluene treated with equimolar amounts of 9-borabicyclo(3.3.1)nonane in one portion, heated up to 90-110°C for 2-5 min; evapd.(vac.); | |
In benzene (Ar), soln. of silane in benzene treated with equimolar amounts of 9-borabicyclo(3.3.1)nonane in one portion, heated up to 90-110°C for 2-5 min; evapd.(vac.); |
(dimethyl(vinyl)silylethynyl)(dimethysilylethynyl)dimethylsilane
9-bora-bicyclo[3.3.1]nonane
4-(9-borabicyclo[3.3.1]non-9-yl)-5-(dimethylsilyl)-1,1,6,6-tetramethyl-1H,2H,3H,6H-1,6-disilapentalene
Conditions | Yield |
---|---|
at 90 - 110℃; Inert atmosphere; regioselective reaction; | 100% |
In toluene (Ar), soln. of silane in toluene treated with equimolar amounts of 9-borabicyclo(3.3.1)nonane in one portion, heated up to 90-110°C for 2-5 min; evapd.(vac.); | |
In benzene (Ar), soln. of silane in benzene treated with equimolar amounts of 9-borabicyclo(3.3.1)nonane in one portion, heated up to 90-110°C for 2-5 min; evapd.(vac.); |
bromodimethylsilylethynyl[dimethyl(vinyl)silylethynyl]dimethylsilane
9-bora-bicyclo[3.3.1]nonane
4-(9-borabicyclo[3.3.1]non-9-yl)-5-(bromodimethylsilyl)-1,1,6,6-tetramethyl-1H,2H,3H,6H-1,6-disilapentalene
Conditions | Yield |
---|---|
at 90 - 110℃; Inert atmosphere; regioselective reaction; | 100% |
In toluene (Ar), soln. of silane in toluene treated with equimolar amounts of 9-borabicyclo(3.3.1)nonane in one portion, heated up to 90-110°C for 2-5 min; evapd.(vac.); | |
In benzene (Ar), soln. of silane in benzene treated with equimolar amounts of 9-borabicyclo(3.3.1)nonane in one portion, heated up to 90-110°C for 2-5 min; evapd.(vac.); |
trimethylsilylethynyl[methyl(phenyl)(vinyl)silylethynyl]dimethylsilane
9-bora-bicyclo[3.3.1]nonane
4-(9-borabicyclo[3.3.1]non-9-yl)-1,6,6-trimethyl-1-phenyl-5-(trimethylsilyl)-1H,2H,3H,6H-1,6-disilapentalene
Conditions | Yield |
---|---|
at 90 - 110℃; Inert atmosphere; regioselective reaction; | 100% |
In toluene (Ar), soln. of silane in toluene treated with equimolar amounts of 9-borabicyclo(3.3.1)nonane in one portion, heated up to 90-110°C for 2-5 min; evapd.(vac.); | |
In benzene (Ar), soln. of silane in benzene treated with equimolar amounts of 9-borabicyclo(3.3.1)nonane in one portion, heated up to 90-110°C for 2-5 min; evapd.(vac.); |
bromodimethylsilylethynyl[diphenyl(vinyl)silylethynyl]dimethylsilane
9-bora-bicyclo[3.3.1]nonane
4-(9-borabicyclo[3.3.1]non-9-yl)-5-(bromodimethylsilyl)-6,6-dimethyl-1,1-diphenyl-1H,2H,3H,6H-1,6-disilapentalene
Conditions | Yield |
---|---|
at 90 - 110℃; Inert atmosphere; regioselective reaction; | 100% |
In toluene (Ar), soln. of silane in toluene treated with equimolar amounts of 9-borabicyclo(3.3.1)nonane in one portion, heated up to 90-110°C for 2-5 min; evapd.(vac.); | |
In benzene (Ar), soln. of silane in benzene treated with equimolar amounts of 9-borabicyclo(3.3.1)nonane in one portion, heated up to 90-110°C for 2-5 min; evapd.(vac.); |
triphenylsilylethynyl[methyl(phenyl)(vinyl)silylethynyl]dimethylsilane
9-bora-bicyclo[3.3.1]nonane
4-(9-borabicyclo[3.3.1]non-9-yl)-1,6,6-trimethyl-1-phenyl-5-(triphenylsilyl)-1H,2H,3H,6H-1,6-disilapentalene
Conditions | Yield |
---|---|
at 90 - 110℃; Inert atmosphere; regioselective reaction; | 100% |
In toluene (Ar), soln. of silane in toluene treated with equimolar amounts of 9-borabicyclo(3.3.1)nonane in one portion, heated up to 90-110°C for 2-5 min; evapd.(vac.); | |
In benzene (Ar), soln. of silane in benzene treated with equimolar amounts of 9-borabicyclo(3.3.1)nonane in one portion, heated up to 90-110°C for 2-5 min; evapd.(vac.); |
Conditions | Yield |
---|---|
In dichloromethane at 20℃; Inert atmosphere; | 100% |
(4R)-5-(tert-butyldiphenylsilyloxy)-4-methyl-1-pentene
9-bora-bicyclo[3.3.1]nonane
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
In benzene-d6 at 80 - 100℃; for 0.666667h; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
With 1,3-di-tert-butylimidazol-2-ylidene In tetrahydrofuran at 70℃; under 750.075 - 2250.23 Torr; for 0.2h; Solvent; Temperature; Reagent/catalyst; Inert atmosphere; Glovebox; Sealed tube; | 100% |
With 1-dimesitylboryl-1’-diphenylphosphino-ferrocene In tetrahydrofuran-d8 at 70℃; under 750.075 Torr; for 20h; Catalytic behavior; Reagent/catalyst; Temperature; Time; Inert atmosphere; Schlenk technique; Sealed tube; | |
With C9H18ClN3Si In tetrahydrofuran at 20℃; under 760.051 Torr; for 23h; Catalytic behavior; Mechanism; Reagent/catalyst; Time; Solvent; | 100 %Spectr. |
trimethylamine-N-oxide
4-methyl-N-(2-propenyl)benzenesulfonamide
9-bora-bicyclo[3.3.1]nonane
Conditions | Yield |
---|---|
Stage #1: 4-methyl-N-(2-propenyl)benzenesulfonamide; 9-bora-bicyclo[3.3.1]nonane In tetrahydrofuran at 0 - 20℃; Stage #2: trimethylamine-N-oxide In tetrahydrofuran; dichloromethane | 100% |
Conditions | Yield |
---|---|
Stage #1: 9-bora-bicyclo[3.3.1]nonane; cyclohexene In tetrahydrofuran at 0 - 20℃; Stage #2: trimethylamine-N-oxide In tetrahydrofuran; dichloromethane | 100% |
Conditions | Yield |
---|---|
Stage #1: 4-(allyloxy)-1-benzylpiperidine; 9-bora-bicyclo[3.3.1]nonane In tetrahydrofuran at 0 - 20℃; Stage #2: trimethylamine-N-oxide In tetrahydrofuran; dichloromethane | 100% |
Conditions | Yield |
---|---|
Stage #1: 9-bora-bicyclo[3.3.1]nonane; 1-allyl-1H-pyrrolo[2,3-b]pyridine In tetrahydrofuran at 0 - 20℃; Stage #2: trimethylamine-N-oxide In tetrahydrofuran; dichloromethane | 100% |
Conditions | Yield |
---|---|
In dichloromethane at 45℃; for 24h; Schlenk technique; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
In tetrahydrofuran for 16h; | 100% |
9-bora-bicyclo[3.3.1]nonane
Conditions | Yield |
---|---|
In tetrahydrofuran at 60℃; for 12h; Schlenk technique; Inert atmosphere; | 100% |
In tetrahydrofuran at 20℃; for 6h; Glovebox; | 95% |
Conditions | Yield |
---|---|
In tetrahydrofuran at 60℃; for 12h; Schlenk technique; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
In tetrahydrofuran at 60℃; for 12h; Schlenk technique; Inert atmosphere; | 100% |
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