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678503 Sigma-Aldrich

(+)-Ipc2B(allyl)borane solution

1 M in pentane

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

  • CAS Number 106356-53-0

  • Linear Formula (C10H17)2BCH2CH=CH2

  • Molecular Weight 326.37

  •  PubChem Substance ID 24885431

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Properties

Related Categories Allylation, Asymmetric Synthesis, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents
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

Description

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.

General description

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

Packaging

5, 25 mL in ampule

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.

Safety & Documentation

Safety Information

Signal word 
Danger
RIDADR 
UN1265 - class 3 - PG 2 - Pentanes solution
WGK Germany 
3
Flash Point(F) 
-56.2 °F
Flash Point(C) 
-49 °C
Protocols & Articles

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.1 Although a variety reagent...
William Sommer
ChemFiles 2008, 8.6, 7.
Keywords: Allylborations, Asymmetric synthesis

Peer-Reviewed Papers
15

References

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