Skip to Content
Merck
All Photos(1)

Key Documents

More Documents

678503

Sigma-Aldrich

(+)-Ipc2B(allyl)borane solution

1 M in pentane

Synonym(s):

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

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

Looking for similar products? Visit Product Comparison Guide

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
View All Related Papers

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.

Contact Technical Service