1,5-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% |
The CAS register number of 9-Borabicyclo[3.3.1]nonane is 280-64-8. It also can be called as 9-Borabicyclo[3.3.1]nonan and the systematic name about this chemical is 9-borabicyclo[3.3.1]nonane. The molecular formula about this chemical is C8H15B and the molecular weight is 122.02.
Physical properties about 9-Borabicyclo[3.3.1]nonane are: (1)Flash Point: 62.3 °C; (2)Enthalpy of Vaporization: 39.86 kJ/mol; (3)Boiling Point: 179.3 °C at 760 mmHg; (4)Vapour Pressure: 1.28 mmHg at 25°C .
Preparation: this chemical can be prepared by cycloocta-1c,5c-diene. This reaction will need reagent BH3*Me2S and solvent tetrahydrofuran. The reaction time is 105 min with reaction temperature of -5 - 67 ℃.
Uses of 9-Borabicyclo[3.3.1]nonane: it can be used to produce lithium dihydrido borata-bicyclo[3.3.0]nonane. This reaction will need reagent LiH and solvent tetrahydrofuran with reaction time of 1 hours. The yield is about 94%.
When you are using this chemical, please be cautious about it as the following:
This chemical is harmful by inhalation, in contact with skin and if swallowed and it is irritating to eyes, respiratory system and skin, it can react violently with water and contact with water liberates extremely flammable gases, it is highly flammable and it may form explosive peroxides, it is also Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. it has risk of impaired fertility and it has danger of serious damage to health by prolonged exposure, its vapours may cause drowsiness and dizziness, it is harmful beacuse it may cause lung damage if swallowed. When you are using it, wear suitable protective clothing, gloves and eye/face protection, you need keep away from sources of ignition and do not empty into drains, you also need kep container tightly closedand kep container dry, you should tke precautionary measures against static discharges and avoid release to the environment. Refer to special instructions / safety data sheets. If swallowed, do not induce vomitting; seek medical advice immediately and show this container or label. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice, in case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) and in case of fire use ... (there follows the type of fire-fighting equipment to be used.)
You can still convert the following datas into molecular structure:
(1)SMILES: B1C2CCCC1CCC2
(2)InChI: InChI=1/C8H15B/c1-3-7-5-2-6-8(4-1)9-7/h7-9H,1-6H2
(3)InChIKey: FEJUGLKDZJDVFY-UHFFFAOYAE
(4)Std. InChI: InChI=1S/C8H15B/c1-3-7-5-2-6-8(4-1)9-7/h7-9H,1-6H2
(5)Std. InChIKey: FEJUGLKDZJDVFY-UHFFFAOYSA-N
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