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678503

(+)-Ipc2B(allyl)borane solution

1 M in pentane

Synonym(s):

(+)-Ipc2B(allyl) solution, (+)-B-Allyldiisopinocampheylborane solution

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About This Item

Linear Formula:
(C10H17)2BCH2CH=CH2
CAS Number:
106356-53-0
Molecular Weight:
326.37
MDL number:
MFCD09038447
UNSPSC Code:
12352002
PubChem Substance ID:
24885431
NACRES:
NA.22

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SMILES string

C[C@@H]1[C@H](C[C@H]2C[C@@H]1C2(C)C)B(CC=C)[C@H]3C[C@H]4C[C@@H]([C@@H]3C)C4(C)C

InChI

1S/C23H39B/c1-8-9-24(20-12-16-10-18(14(20)2)22(16,4)5)21-13-17-11-19(15(21)3)23(17,6)7/h8,14-21H,1,9-13H2,2-7H3/t14-,15-,16+,17+,18-,19-,20-,21-/m0/s1

InChI key

ZIXZBDJFGUIKJS-AXSQLCHVSA-N

optical activity

[α]20/D +14°, c = 1 in pentane

concentration

1 M in pentane

bp

35-36 °C

density

0.735 g/mL at 25 °C

storage temp.

−20°C

Quality Level

100

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1 of 4

This Item
67853823273485126
(+)-Ipc2B(allyl)borane solution 1 M in pentane

Sigma-Aldrich

678503

(+)-Ipc2B(allyl)borane solution

(−)-Ipc2B(allyl)borane solution 1 M in pentane

Sigma-Aldrich

678538

(−)-Ipc2B(allyl)borane solution

R-Alpine-Borane® solution 0.5 M in THF

Sigma-Aldrich

232734

R-Alpine-Borane® solution

Silanization solution I ~5% (dimethyldichlorosilane in heptane), Selectophore™

Supelco

85126

Silanization solution I

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

200

storage temp.

−20°C

storage temp.

−20°C

storage temp.

-

storage temp.

-

density

0.735 g/mL at 25 °C

density

0.638 g/mL at 25 °C

density

0.896 g/mL at 25 °C

density

-

bp

35-36 °C

bp

35-36 °C

bp

-

bp

-

optical activity

[α]20/D +14°, c = 1 in pentane

optical activity

[α]20/D −35 to ±5°, c = 1

optical activity

[α]20/D −3.0°, neat

optical activity

-

concentration

1 M in pentane

concentration

1 M in pentane

concentration

0.5 M in THF

concentration

~5% (dimethyldichlorosilane in heptane)

General description

http://www.sigmaaldrich.com/ifb/acta/v35/acta-vol35-2002.html#32

Application

This allylboration reagent is a convenient, salt-free, stable solution of a chiral allyl borane for asymmetric allylation of aldehydes leading to chiral homoallylic alcohols.[1][2][3]

Other Notes

Material may become hazy upon cooler storage, this will not affect use
Under refrigerator storage, these salt-free, Ipc2B(allyl) reagents do not show any appreciable decrease in selectivity is observed after several months. They exhibit excellent reactivity and reactions can be performed at 5°C, even in water.[4]

Disclaimer

Supply conditions do not apply to the regions and states of Brazil: North, Northeast, Mato Grosso do Sul, Mato Grosso, and Rio Grande do Sul.

accessory

Product No.
Description
Pricing

signalword

Danger

Hazard Classifications

Aquatic Chronic 2 - Asp. Tox. 1 - Eye Irrit. 2 - Flam. Liq. 1 - Skin Irrit. 2 - STOT SE 3

target_organs

Central nervous system, Respiratory system

Storage Class

3 - Flammable liquids

wgk

WGK 3

flash_point_f

-56.2 °F

flash_point_c

-49 °C

ppe

Eyeshields, Faceshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SHBS7671
SHBN8942
SHBJ8984
SHBJ7019
SHBG1661V

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Total syntheses of epothilones A and B via a macrolactonization-based strategy
Nicolaou KC, et al.
Journal of the American Chemical Society, 119.34, 7974-7991 (1997)
Stereoselective Synthesis of 2, 6?Disubstituted Piperidines Using the Iridium?Catalyzed Allylic Cyclization as Configurational Switch: Asymmetric Total Synthesis of (+)?241 D and Related Piperidine Alkaloids
Gnamm, Christian, et al.
Chemistry?A European Journal , 15.9, 2050-2054 (2009)
Intramolecular Hydride Addition to Pyridinium Salts: New Routes to Enantiopure Dihydropyridones
Donohoe, Timothy J., et al.
Organic Letters, 13.8, 2074-2077 (2011)
Total synthesis of hyptolide
Chakraborty, Tushar Kanti, and Subhas Purkait.
Tetrahedron Letters, 49.38, 5502-5504 (2008)
Concise total syntheses of epothilone A and C based on alkyne metathesis
Furstner, Alois, Christian Mathes, and Karol Grela.
Chemical Communications (Cambridge, England), 12, 1057-1059 (2001)
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