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233161

Sigma-Aldrich

3′-(Trifluoromethyl)acetophenone

99%

Sinónimos:

3-Acetylbenzotrifluoride

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About This Item

Fórmula lineal:
CF3C6H4COCH3
Número de CAS:
349-76-8
Peso molecular:
188.15
Beilstein/REAXYS Number:
640151
EC Number:
206-490-4
MDL number:
MFCD00000391
UNSPSC Code:
12352100
PubChem Substance ID:
24853957
NACRES:
NA.22

assay

99%

form

liquid

refractive index

n20/D 1.4611 (lit.)

bp

198-200 °C (lit.)

density

1.235 g/mL at 25 °C (lit.)

SMILES string

CC(=O)c1cccc(c1)C(F)(F)F

InChI

1S/C9H7F3O/c1-6(13)7-3-2-4-8(5-7)9(10,11)12/h2-5H,1H3

InChI key

ABXGMGUHGLQMAW-UHFFFAOYSA-N

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General description

Asymmetric catalytic addition of ethyl groups to 3′-(trifluoromethyl)acetophenone catalyzed by ligands derived from trans-1,2-diaminocyclohexane and camphor sulfonyl chloride has been reported. Phenylation of 3′-(trifluoromethyl)acetophenone in the presence of dihydroxy bis(sulfonamide) ligand (enantioselective catalyst), titanium tetraisopropoxide and diphenylzinc has been investigated.

Application

3′-(Trifluoromethyl)acetophenone has been used in a key step during the preparation of a commercial fungicide.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk_germany

WGK 1

flash_point_f

174.2 °F - closed cup

flash_point_c

79 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

Certificados de análisis (COA)

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Celina García et al.
Journal of the American Chemical Society, 124(37), 10970-10971 (2002-09-13)
Many catalysts will promote the asymmetric addition of alkylzinc reagents to aldehydes. In contrast, there are no reports of additions to ketones that are both general and highly enantioselective. We describe herein a practical catalytic asymmetric addition of ethyl groups
Serafino Gladiali et al.
Chemical Society reviews, 35(3), 226-236 (2006-03-01)
Hydrogen transfer reduction processes are attracting increasing interest from synthetic chemists in view of their operational simplicity and high selectivity. In this tutorial review the most significant advances recently achieved in the stereoselective reduction of unsaturated organic compounds catalyzed by
Celina García et al.
Organic letters, 5(20), 3641-3644 (2003-09-26)
[reaction: see text] The catalytic asymmetric addition of phenyl groups from diphenylzinc to ketones is reported. The catalyst, generated from a dihydroxy bis(sulfonamide) ligand and titanium tetraisopropoxide, gives good to excellent enantioselectivities with a range of substrates.

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