416916
Dicyclohexyliodoborane
97%
Synonym(s):
Dicyclohexylboryl iodide
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About This Item
Linear Formula:
(C6H11)2BI
CAS Number:
Molecular Weight:
304.02
MDL number:
UNSPSC Code:
12352101
PubChem Substance ID:
NACRES:
NA.22
Assay
97%
form
liquid
reaction suitability
reagent type: reductant
bp
198-200 °C/1.25 mmHg (lit.)
density
1.325 g/mL at 25 °C (lit.)
SMILES string
IB(C1CCCCC1)C2CCCCC2
InChI
1S/C12H22BI/c14-13(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h11-12H,1-10H2
InChI key
RWFGGTOYIFQXAO-UHFFFAOYSA-N
Application
Dicyclohexyliodoborane (Chx2BI) can be used as a reagent:
- For the enolboration of esters and tertiary amides to synthesize corresponding Z or E enolates.
- In the stereoselective preparation of β-hydroxy-α-trifluoromethyl carboxylic acids via haloborane-mediated diastereoselective aldol addition of aldehydes with trifluoropropanoic acid.
- In the total synthesis of pordamacrine A, and trocheliophorolide D.
Reactant for:
- Preparation of vinyloxyboranes
Certificates of Analysis (COA)
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Total Synthesis of the Proposed Structure of Trocheliophorolide D
Hwang S, et al.
European Journal of Organic Chemistry, 2011(36), 7414-7418 (2011)
Enolboration. 6. Dicyclohexyliodoborane, a Versatile Reagent for the Stereoselective Synthesis of Either Z or E Enolates from Representative Esters
Ganesan K and Brown HC
The Journal of Organic Chemistry, 59(9), 2336-2340 (1994)
Dicyclohexyliodoborane/Triethylamine-a new reagent which achieves the facile enolboration of esters and tertiary amides
Brown HC and Ganesan K
Tetrahedron Letters, 33(24), 3421-3424 (1992)
A boron-based Ireland-Claisen approach to the synthesis of pordamacrine A
Seizert, Curtis A and Ferreira, Eric M
Tetrahedron, 73(29), 4186-4194 (2017)
Diastereoselective synthesis of anti-3-hydroxy-2-trifluoromethyl carboxylic acids
Ramachandran PV, et al.
Tetrahedron Letters, 56(23), 3019-3022 (2015)
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