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CAS No.: | 21947-87-5 |
---|---|
Name: | Diisopinocampheylborane |
Article Data: | 18 |
Molecular Structure: | |
Formula: | C20H35B |
Molecular Weight: | 286.309 |
Synonyms: | Borane,bis(2,6,6-trimethylbicyclo[3.1.1]hept-3-yl)-, [1S-[1a,2b,3a(1R*,2S*,3R*,5R*),5a]]-;Borane, di-3-pinanyl-, (+)-(8CI);(+)-Diisopinocampheylborane;d-Diisopinocampheylborane; |
Boiling Point: | 351.475oC at 760 mmHg |
Flash Point: | 166.367oC |
PSA: | 0.00000 |
LogP: | 5.40410 |
(-)-α-pinene
L-diisopinocampheylborane
Conditions | Yield |
---|---|
With borane N-ethyl-N-isopropylaniline complex In 1,4-dioxane hydroboration; | 99% |
With dimethylsulfide borane complex In tetrahydrofuran at 20℃; Inert atmosphere; | 73% |
With sodium tetrahydroborate; boron trifluoride diethyl etherate |
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; for 16h; Inert atmosphere; | 82% |
In tetrahydrofuran at 0℃; for 0.5h; | 60% |
In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; | 52% |
In tetrahydrofuran | |
In tetrahydrofuran at 0℃; |
dimethylsulfide borane complex
(1R,5R)-(+)-β-pinene
L-diisopinocampheylborane
Conditions | Yield |
---|---|
In tetrahydrofuran pinene was slowly added to THF soln. of BMS at 0°C (N2); stirring for 2.5 h; evapn.; |
Conditions | Yield |
---|---|
In tetrahydrofuran at 0 - 20℃; for 2h; Inert atmosphere; stereoselective reaction; |
1-benzyl-3-methyl-1H-imidazol-3-ium iodide
L-diisopinocampheylborane
Conditions | Yield |
---|---|
With potassium hexamethylsilazane In tetrahydrofuran at 25℃; Inert atmosphere; Schlenk technique; | 83% |
benzaldehyde
L-diisopinocampheylborane
3-phenyl-1-(tributylstannyl)-1,2-propadiene
Conditions | Yield |
---|---|
In diethyl ether Sn compd. in Et2O treated with B compd. at 0°C for 5 h, C6H5CHO added at -78°C, stirred at -78°C for 8 h; NaHCO3 and H2O2 added at 0°C; 94 % ee; | 76% |
3-phenyl-propionaldehyde
L-diisopinocampheylborane
3-phenyl-1-(tributylstannyl)-1,2-propadiene
Conditions | Yield |
---|---|
In diethyl ether Sn compd. in Et2O treated with B compd. at 0°C for 5 h, C6H5(CH2)2CHO added at -78°C, stirred at -78°C for 8 h; NaHCO3 and H2O2 added at 0°C; 94 % ee; | 71% |
L-diisopinocampheylborane
Conditions | Yield |
---|---|
With potassium hexamethylsilazane In tetrahydrofuran at 25℃; Inert atmosphere; Schlenk technique; | 60% |
N-methyl-N'-phenyl imidazolium iodide
L-diisopinocampheylborane
Conditions | Yield |
---|---|
With potassium hexamethylsilazane In tetrahydrofuran at 25℃; Inert atmosphere; Schlenk technique; | 56% |
1,3-dimethylimidazolim iodide
L-diisopinocampheylborane
Conditions | Yield |
---|---|
With potassium hexamethylsilazane In tetrahydrofuran at 20℃; for 20h; Sealed tube; Inert atmosphere; Glovebox; | 37% |
With potassium hexamethylsilazane In tetrahydrofuran at 25℃; for 20h; Inert atmosphere; Schlenk technique; | 37% |
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Molecular Structure of Diisopinocampheylborane (CAS No.21947-87-5):
Molecular Formula: C20H35B
Molecular Weight: 286.30
CAS No: 21947-87-5
IUPAC Name: bis {(1S,2S,3S,5R)-2,6,6-Trimethylbicyclo [3.1.1] heptan-3-yl} borane
Diisopinocampheylborane was reported in 1961 by Zweifel and Brown in a pioneering demonstration of asymmetric synthesis using boranes.
Diisopinocampheylborane (CAS No.21947-87-5) is mainly used for the synthesis of chiral secondary alcohols.
Diisopinocampheylborane is now more commonly generated from borane-methyl sulfide (BMS).
Diisopinocampheylborane (CAS No.21947-87-5), its synonyms are (+)-Diisopinocampheylborane ; Bis[(1S,2R,3S,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-3-yl]borane .