771880
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:
Molecular Weight:
236.59
UNSPSC Code:
12352101
PubChem Substance ID:
NACRES:
NA.22
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
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
Application
Reagent promotes diastereoselective syn-aldol products from beta-gamma unsaturated propanoates.
Storage Class
10 - Combustible liquids
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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