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Diisopinocampheylborane

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Name

Diisopinocampheylborane

EINECS N/A
CAS No. 21947-87-5 Density N/A
PSA 0.00000 LogP 5.40410
Solubility N/A Melting Point N/A
Formula C20H35B Boiling Point 351.475oC at 760 mmHg
Molecular Weight 286.309 Flash Point 166.367oC
Transport Information N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 21947-87-5 (Diisopinocampheylborane) Hazard Symbols N/A
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;

Article Data 18

Diisopinocampheylborane Synthetic route

7785-26-4

(-)-α-pinene

21947-87-5

L-diisopinocampheylborane

Conditions
ConditionsYield
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
7785-26-4

(-)-α-pinene

13292-87-0

dimethylsulfide borane complex

21947-87-5

L-diisopinocampheylborane

Conditions
ConditionsYield
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℃;
13292-87-0

dimethylsulfide borane complex

127-91-3

(1R,5R)-(+)-β-pinene

21947-87-5

L-diisopinocampheylborane

Conditions
ConditionsYield
In tetrahydrofuran pinene was slowly added to THF soln. of BMS at 0°C (N2); stirring for 2.5 h; evapn.;
14044-65-6

borane-THF

7785-26-4

(-)-α-pinene

21947-87-5

L-diisopinocampheylborane

Conditions
ConditionsYield
In tetrahydrofuran at 0 - 20℃; for 2h; Inert atmosphere; stereoselective reaction;
15095-61-1

1-benzyl-3-methyl-1H-imidazol-3-ium iodide

21947-87-5

L-diisopinocampheylborane

(1-benzyl-3-methylimidazol-2-yl)di((1S,2R,3S,5S)-isopinocampheyl)borane

Conditions
ConditionsYield
With potassium hexamethylsilazane In tetrahydrofuran at 25℃; Inert atmosphere; Schlenk technique;83%
100-52-7

benzaldehyde

21947-87-5

L-diisopinocampheylborane

155818-57-8

3-phenyl-1-(tributylstannyl)-1,2-propadiene

C6H5CH(OH)CH(C6H5)CHCHSn(C4H9)3

Conditions
ConditionsYield
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%
104-53-0

3-phenyl-propionaldehyde

21947-87-5

L-diisopinocampheylborane

155818-57-8

3-phenyl-1-(tributylstannyl)-1,2-propadiene

C6H5(CH2)2CH(OH)CH(C6H5)CHCHSn(C4H9)3

Conditions
ConditionsYield
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%
21947-87-5

L-diisopinocampheylborane

1-methyl-3-tert-butylimidazolium halide

1-methyl-3-tert-butylimidazolium halide

(1-tert-butyl-3-methylimidazol-2-yl)di((1S,2R,3S,5S)-isopinocampheyl)borane

Conditions
ConditionsYield
With potassium hexamethylsilazane In tetrahydrofuran at 25℃; Inert atmosphere; Schlenk technique;60%
65039-06-7

N-methyl-N'-phenyl imidazolium iodide

21947-87-5

L-diisopinocampheylborane

(1-methyl-3-phenylimidazol-2-yl)di((1S,2R,3S,5S)-isopinocampheyl)borane

Conditions
ConditionsYield
With potassium hexamethylsilazane In tetrahydrofuran at 25℃; Inert atmosphere; Schlenk technique;56%
4333-62-4

1,3-dimethylimidazolim iodide

21947-87-5

L-diisopinocampheylborane

1,3-dimethylimidazol-2-ylidene-di-(1S,2R,3S,5S)-isopinocampheylborane

Conditions
ConditionsYield
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%

Diisopinocampheylborane Chemical Properties

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 History

  Diisopinocampheylborane was reported in 1961 by Zweifel and Brown in a pioneering demonstration of asymmetric synthesis using boranes.

Diisopinocampheylborane Uses

  Diisopinocampheylborane (CAS No.21947-87-5) is mainly used for the synthesis of chiral secondary alcohols.

Diisopinocampheylborane Production

  Diisopinocampheylborane is now more commonly generated from borane-methyl sulfide (BMS).

Diisopinocampheylborane Specification

   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 .

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