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667005

Sigma-Aldrich

(R)-(+)-3,3,3-Trifluoro-1,2-epoxypropane

97%

Synonym(s):

(R)-(+)-2-(Trifluoromethyl)oxirane

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About This Item

Empirical Formula (Hill Notation):
C3H3F3O
CAS Number:
Molecular Weight:
112.05
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22

assay

97%

refractive index

n20/D <1.300

bp

25-32 °C

density

1.294 g/mL at 25 °C

functional group

ether
fluoro

storage temp.

2-8°C

SMILES string

FC(F)(F)[C@H]1CO1

InChI

1S/C3H3F3O/c4-3(5,6)2-1-7-2/h2H,1H2/t2-/m1/s1

InChI key

AQZRARFZZMGLHL-UWTATZPHSA-N

Application

(R)-(+)-3,3,3-Trifluoro-1,2-epoxypropane can be used as a substrate to synthesize:
  • Substituted trifluoro amino propanols, which are found to be potent inhibitors of cholesteryl ester transfer protein.
  • (2R) Trifluoro-(methoxybenzyloxy)-propanol (chiral glycol) by reacting with 4-methoxybenzyl alcohol in the presence of NaH. Chiral glycol intermediate is further utilized for the preparation of trifluoromethyl glycol carbamates as potential monoacylglycerol lipase (MAGL) inhibitors.

pictograms

Flame

signalword

Danger

hcodes

Hazard Classifications

Flam. Liq. 1

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

-14.8 °F

flash_point_c

-26 °C

ppe

Eyeshields, Faceshields, Gloves


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Discovery of trifluoromethyl glycol carbamates as potent and selective covalent monoacylglycerol lipase (MAGL) inhibitors for treatment of neuroinflammation
McAllister LA, et al.
Journal of Medicinal Chemistry, 61(7), 3008-3026 (2018)
Discovery of a simple picomolar inhibitor of cholesteryl ester transfer protein
Reinhard EJ, et al.
Journal of Medicinal Chemistry, 46(11), 2152-2168 (2003)
Emily J Reinhard et al.
Journal of medicinal chemistry, 46(11), 2152-2168 (2003-05-16)
A novel series of substituted N-[3-(1,1,2,2-tetrafluoroethoxy)benzyl]-N-(3-phenoxyphenyl)-trifluoro-3-amino-2-propanols is described which potently and reversibly inhibit cholesteryl ester transfer protein (CETP). Starting from the initial lead 1, various substituents were introduced into the 3-phenoxyaniline group to optimize the relative activity for inhibition of

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