Diisopinocampheylborane supplier

Name
Diisopinocampheylborane
EINECS
CAS No. 21947-87-5
Article Data18
CAS DataBase
Density
Solubility
Melting Point
Formula C₂₀H₃₅B
Boiling Point 351.475oC at 760 mmHg
Molecular Weight 286.309
Flash Point 166.367oC
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
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;
PSA 0.00000
LogP 5.40410

Synthetic route

: 7785-26-4
(-)-α-pinene

: 21947-87-5
L-diisopinocampheylborane

Conditions

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

: 7785-26-4
(-)-α-pinene

: 13292-87-0
dimethylsulfide borane complex

: 21947-87-5
L-diisopinocampheylborane

Conditions

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℃;

: 13292-87-0
dimethylsulfide borane complex

: 127-91-3
(1R,5R)-(+)-β-pinene

: 21947-87-5
L-diisopinocampheylborane

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

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%

...Expand

: 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

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%

...Expand

: 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

Conditions	Yield
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

Conditions	Yield
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

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%

: 21947-87-5
L-diisopinocampheylborane

: 1,3-diisopropyl-1H-imidazol-3-ium chloride

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

Conditions

Conditions	Yield
With potassium hexamethylsilazane In tetrahydrofuran at 20℃; for 20h; Sealed tube; Inert atmosphere; Glovebox;	34%

: 21947-87-5
L-diisopinocampheylborane

1,3-diisopropylimidazolium halide: 1,3-diisopropylimidazolium halide

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

Conditions

Conditions	Yield
With potassium hexamethylsilazane In tetrahydrofuran at 25℃; Inert atmosphere; Schlenk technique;	34%

: 22929-50-6
3-methoxy-2,5-dihydro-furan

: 21947-87-5
L-diisopinocampheylborane

A: ((3R,4S)-4-Methoxy-tetrahydro-furan-3-yl)-bis-((1S,2R,3S,5S)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl)-borane

B: ((3S,4R)-4-Methoxy-tetrahydro-furan-3-yl)-bis-((1S,2R,3S,5S)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl)-borane

Conditions

Conditions	Yield
With Pinene In tetrahydrofuran at -25℃; for 30h; asymmetric hydroboration; Title compound not separated from byproducts;

...Expand

: 1072-59-9
1-methoxycyclopentene

: 21947-87-5
L-diisopinocampheylborane

A: ((1R,2R)-2-Methoxy-cyclopentyl)-bis-((1S,2R,3S,5S)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl)-borane

B: ((1S,2S)-2-Methoxy-cyclopentyl)-bis-((1S,2R,3S,5S)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl)-borane

Conditions

Conditions	Yield
With Pinene In tetrahydrofuran at -25℃; for 76h; asymmetric hydroboration; Title compound not separated from byproducts;

...Expand

: 17065-24-6
1-ethoxycyclopentene

: 21947-87-5
L-diisopinocampheylborane

A: ((1R,2R)-2-Ethoxy-cyclopentyl)-bis-((1S,2R,3S,5S)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl)-borane

B: ((1S,2S)-2-Ethoxy-cyclopentyl)-bis-((1S,2R,3S,5S)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl)-borane

Conditions

Conditions	Yield
With Pinene In tetrahydrofuran at -25℃; for 80h; asymmetric hydroboration; Title compound not separated from byproducts;

...Expand

: 113548-17-7
1-(benzyloxy)cyclopentene

: 21947-87-5
L-diisopinocampheylborane

A: ((1R,2R)-2-Benzyloxy-cyclopentyl)-bis-((1S,2R,3S,5S)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl)-borane

B: ((1S,2S)-2-Benzyloxy-cyclopentyl)-bis-((1S,2R,3S,5S)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl)-borane

Conditions

Conditions	Yield
With Pinene In tetrahydrofuran at -15℃; for 120h; asymmetric hydroboration; Title compound not separated from byproducts;

...Expand

: 21947-87-5
L-diisopinocampheylborane

: 9-(cyclopent-1-enyloxy)-9-bora-bicyclo[3.3.1]nonane

A: 9-{(1R,2R)-2-[Bis-((1S,2R,3S,5S)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl)-boranyl]-cyclopentyloxy}-9-bora-bicyclo[3.3.1]nonane

B: 9-{(1S,2S)-2-[Bis-((1S,2R,3S,5S)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl)-boranyl]-cyclopentyloxy}-9-bora-bicyclo[3.3.1]nonane

Conditions

Conditions	Yield
With Pinene In tetrahydrofuran at -10℃; for 72h; asymmetric hydroboration; Title compound not separated from byproducts;

...Expand

: 21947-87-5
L-diisopinocampheylborane

: 479579-58-3
2-allenyl-4,4,5,5-tetraphenyl-1,3,2-dioxaborolane

: 2-{(E)-3-[Bis-((1S,2R,3S,5S)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl)-boranyl]-propenyl}-4,4,5,5-tetraphenyl-[1,3,2]dioxaborolane

Conditions

Conditions	Yield
In dichloromethane at 0℃; for 2.5h;
In dichloromethane at 0 - 23℃;

: 21947-87-5
L-diisopinocampheylborane

: 169517-16-2
2-allenyl-[1,3,2]-dioxaborinane

: 2-{(E)-3-[Bis-((1S,2R,3S,5S)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl)-boranyl]-propenyl}-[1,3,2]dioxaborinane

Conditions

Conditions	Yield
In dichloromethane at 0 - 20℃;

: 21947-87-5
L-diisopinocampheylborane

: 479579-58-3
2-allenyl-4,4,5,5-tetraphenyl-1,3,2-dioxaborolane

: 2-{(E)-3-[Bis-((1S,2R,3S,5S)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl)-boranyl]-allyl}-4,4,5,5-tetraphenyl-[1,3,2]dioxaborolane

Conditions

Conditions	Yield
In dichloromethane at 0℃; for 2h;

: 67-56-1
methanol

: 21947-87-5
L-diisopinocampheylborane

: 99438-28-5
(+)-B-methoxydiisocamphenylborane

Conditions

Conditions	Yield
In diethyl ether at 0℃; for 2h;
In tetrahydrofuran at 20℃; for 4h; Inert atmosphere;

: 603040-81-9
(R)-1-methoxy-4-((pent-4-yn-2-yloxy)methyl)benzene

: 21947-87-5
L-diisopinocampheylborane

: C33H51BO2

Conditions

Conditions	Yield
In tetrahydrofuran at -35 - 20℃; for 2.5h;

: 21947-87-5
L-diisopinocampheylborane

: 106356-53-0
B-allyldiisopinocampheylborane

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: diethyl ether / 2 h / 0 °C 2: diethyl ether / 1 h / 20 °C View Scheme

: 21947-87-5
L-diisopinocampheylborane

: C72H88B2O6Si

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: CH2Cl2 / 2 h / 0 °C 2: CH2Cl2 / 18 h / -78 °C View Scheme

: 21947-87-5
L-diisopinocampheylborane

: C85H100B2O8Si

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: CH2Cl2 / 2 h / 0 °C 2: CH2Cl2 / 2.5 h / -78 °C View Scheme

: 498-66-8
norborn-2-ene

: 21947-87-5
L-diisopinocampheylborane

: exo-norbornyldiisopinocampheylborane

Conditions

Conditions	Yield
Norbornene is hydroborated with Ipc2BH at -25°C (83% ee).;

: 21947-87-5
L-diisopinocampheylborane

: 175892-48-5
B-bromodiisopinocampheylborane

Conditions

Conditions	Yield
With hydrogen bromide In pentane 0°C;;

: 21947-87-5
L-diisopinocampheylborane

: 175892-49-6
B-iododiisopinocampheylborane

Conditions

Conditions	Yield
With iodine In pentane 0°C;;

: 21947-87-5
L-diisopinocampheylborane

: 112246-73-8
B-chlorodiisopinocampheylborane

Conditions

Conditions	Yield
With hydrogenchloride In pentane 0°C;;

: 590-18-1
(Z)-2-Butene

: 21947-87-5
L-diisopinocampheylborane

: 82248-43-9
B(OH)2CHCH3C2H5

Conditions

Conditions	Yield
With sodium hydroxide; acetaldehyde In tetrahydrofuran mixt. of B compd. and pinene was kept at 0°C (N2) for 3 d; cooling to -25°C, addn. of cis-butene; stirring for 6 h; treatment with AcH with stirring at 25°C for 36 h, evapn., addn. of pentane, treatment with aq. NaOH; treatment with aq. HCl, extn. with Et2O, drying in vac.;

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 .

Product Name

Diisopinocampheylborane

Synthetic route

Diisopinocampheylborane Chemical Properties

Diisopinocampheylborane History

Diisopinocampheylborane Uses

Diisopinocampheylborane Production

Diisopinocampheylborane Specification

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