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678503

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

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 - STOT SE 3

Target Organs

Central nervous system, Respiratory system

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

PRTR

Class I Designated Chemical Substances

FSL

Group 4: Flammable liquids
Special flammables
Hazardous rank I

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

678503-25ML:4548173962399
678503-BULK:
678503-VAR:
678503-5ML:4548173962405

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Certificates of Analysis (COA)

Lot/Batch Number
SHBJ8984
SHBJ7019
SHBG1661V
SHBC4707V
SHBB4581V

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Enantioselective Allylation of (2E, 4E)?2, 4?Dimethylhexadienal: Synthesis of (5R, 6S)?(+)?Pteroenone
Koukal, Petr, and Martin Kotora.
European Journal of Chemistry, 21.20, 7408-7412 (2015)
Total synthesis of (?)-centrolobine: ?-C-glycoside formation via a tandem Grignard addition and stereoselective hemi-ketal reduction
Jennings, Michael P., and Ryan T. Clemens.
Tetrahedron Letters, 46.12, 2021-2024 (2005)
Studies directed toward the synthesis of viridenomycin. Route 1: assembly of three advanced intermediates
Kruger, Albert W., and A. I. Meyers
Tetrahedron Letters, 42.26, 4301-4304 (2001)
A Concise Stereoselective Total Synthesis of Synargentolide A from 3, 4, 6-Tri-O-acetyl-D-glucal
Sabitha, Gowravaram, et al.
Synthesis, 2011.08, 1279-1282 (2011)
Total synthesis of epothilones B and D
Taylor, Richard E., and Yue Chen.
Organic Letters, 3.14, 2221-2221 (2001)
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Articles

Asymmetric Allylboration Using Ipc2B(allyl)

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

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

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