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905119

Sigma-Aldrich

all-cis-Hexafluorocylclohexane

Sinónimos:

all-cis-1,2,3,4,5,6-Hexafluorocyclohexane

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About This Item

Fórmula empírica (notación de Hill):
C6H6F6
Número de CAS:
1699714-60-7
Peso molecular:
192.10
MDL number:
MFCD32661850
UNSPSC Code:
12352101
NACRES:
NA.22

form

solid

mp

289-290 °C

functional group

fluoro

storage temp.

2-8°C

SMILES string

F[C@@H]1[C@@H]([C@@H]([C@@H]([C@@H]([C@@H]1F)F)F)F)F

InChI key

PQJGSPVYVGXTJW-JMVOWJSSSA-N

Categorías relacionadas

Application

The incorporation of fluorine in agrochemical and pharmaceutical compounds is of high interest due to the ability to fine-tune the polarity, pKA-value, conformation and metabolic stability. Derived from a cis-selective hydrogenation developed by Glorius and co-workers, this fluorinated compound displays a diverse utility as a building block for chemical synthesis. All-cis-multifluorinated cyclohexanes are of great interest in material chemistry. All-cis-1,2,3,4,5,6-hexafluorocyclohexane, which has been referred to as “Janus-headed” molecule, is one of the most polar compounds known. Liquid crystalline materials are known applications for all-cis-multifluorinated cyclohexanes.

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Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Neil S Keddie et al.
Nature chemistry, 7(6), 483-488 (2015-05-21)
The highest-energy stereoisomer of 1,2,3,4,5,6-hexafluorocyclohexane, in which all of the fluorines are 'up', is prepared in a 12-step protocol. The molecule adopts a classic chair conformation with alternate C-F bonds aligned triaxially, clustering three highly electronegative fluorine atoms in close
Mario P Wiesenfeldt et al.
Science (New York, N.Y.), 357(6354), 908-912 (2017-08-12)
All-cis-multifluorinated cycloalkanes exhibit intriguing electronic properties. In particular, they display extremely high dipole moments perpendicular to the aliphatic ring, making them highly desired motifs in material science. Very few such motifs have been prepared, as their syntheses require multistep sequences

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