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771880

Sigma-Aldrich

Bis(bicyclo[2.2.1]-2-heptyl)chloroborane

Synonym(s):

Bis-norbornylchloroborane

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About This Item

Empirical Formula (Hill Notation):
C14H22BCl
CAS Number:
137495-66-0
Molecular Weight:
236.59
UNSPSC Code:
12352101
PubChem Substance ID:
329767523
NACRES:
NA.22

form

liquid

refractive index

n20/D 1.517

bp

131-136 °C/760 mmHg (decomposition)

density

1.058 g/mL at 25 °C

storage temp.

2-8°C

SMILES string

ClB(C1C[C@@H]2CC[C@H]1C2)C3C[C@@H]4CC[C@H]3C4

InChI

1S/C14H22BCl/c16-15(13-7-9-1-3-11(13)5-9)14-8-10-2-4-12(14)6-10/h9-14H,1-8H2/t9-,10-,11+,12+,13?,14?/m1/s1

InChI key

FIZRDRGODZJEDW-NXAPOWPLSA-N

Application

Reagent promotes diastereoselective syn-aldol products from beta-gamma unsaturated propanoates.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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P Veeraraghavan Ramachandran et al.
Organic letters, 15(6), 1398-1401 (2013-03-08)
It is reported that appropriate dienolborinates can provide access to both diastereomers of 2-(hydroxymethyl)but-3-enoates through exclusive α-regiocontrol in a non-vinylogous pathway. Contrary to previous reports in which dialkylchloroboranes failed to enolize propanoates, acidity-enhanced but-3-enoates readily undergo enolization, offering unprecedented control

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