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233161

Sigma-Aldrich

3′-(Trifluoromethyl)acetophenone

99%

Synonym(s):

3-Acetylbenzotrifluoride

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About This Item

Linear Formula:
CF3C6H4COCH3
CAS Number:
349-76-8
Molecular Weight:
188.15
Beilstein:
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.)

functional group

fluoro
ketone

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

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 1

Flash Point(F)

174.2 °F - closed cup

Flash Point(C)

79 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 4: Flammable liquids
Type 3 petroleums
Hazardous rank III
Water insoluble liquid

JAN Code

233161-VAR:
233161-BULK:
233161-1G:
233161-5G:
233161-25G:

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Certificates of Analysis (COA)

Lot/Batch Number
BCCD2892
BCCC2028
BCBV5675
BCBR4196V
BCBJ4322V

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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.
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
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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