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Sigma-Aldrich

(+)-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
UNSPSC Code:
12352002
PubChem Substance ID:
24885431
NACRES:
NA.22

optical activity

[α]20/D +14°, c = 1 in pentane

Quality Level

100

concentration

1 M in pentane

bp

35-36 °C

density

0.735 g/mL at 25 °C

storage temp.

−20°C

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

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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.

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.

accessory

Product No.
Description
Pricing

Signal Word

Danger

Hazard Classifications

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

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

-56.2 °F

Flash Point(C)

-49 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Articles

Asymmetric Allylboration Using Ipc2B(allyl)

Asymmetric allylboration of aldehydes is an important method for preparing homoallylic alcohols, as evidenced in numerous complex natural product syntheses.

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