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107840

Sigma-Aldrich

2,2,2-Trifluoroacetophenone

99%

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Synonym(s):
α,α,α-Trifluoroacetophenone, Phenyl trifluoromethyl ketone
Linear Formula:
CF3COC6H5
CAS Number:
Molecular Weight:
174.12
Beilstein:
1866286
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Assay

99%

refractive index

n20/D 1.458 (lit.)

bp

165-166 °C (lit.)
46-48 °C/14 mmHg (lit.)

density

1.24 g/mL at 25 °C (lit.)

SMILES string

FC(F)(F)C(=O)c1ccccc1

InChI

1S/C8H5F3O/c9-8(10,11)7(12)6-4-2-1-3-5-6/h1-5H

InChI key

KZJRKRQSDZGHEC-UHFFFAOYSA-N

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This Item
403229373761216690
refractive index

n20/D 1.458 (lit.)

refractive index

-

refractive index

n20/D 1.361 (lit.)

refractive index

-

bp

165-166 °C (lit.), 46-48 °C/14 mmHg (lit.)

bp

95 °C/4 mmHg (lit.)

bp

59 °C/100 mmHg (lit.)

bp

-

density

1.24 g/mL at 25 °C (lit.)

density

1.662 g/mL at 25 °C (lit.)

density

1.181 g/mL at 25 °C (lit.)

density

-

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

100

General description

2,2,2-Trifluoroacetophenone is the starting material for the synthesis of f 3-trifluoromethyl-3-phenyldiazirine. It undergoes asymmetric reduction with optically active Grignard reagent to form 2,2,2-trifluoro-1-phenylethanol. It undergoes condensation with biphenyl, terphenyl, a mixture of biphenyl with terphenyl, phenyl ether and diphenoxybenzophenone to form new aromatic 3F polymers.

2,2,2-trifluoroacetophenone is used as an organocatalyst for the oxidation of tertiary amines and azines to N-oxidesalkenes.

Application

2,2,2-Trifluoroacetophenone was used in the synthesis of new fluorinated polymers, having high average molecular weight, high thermal stability and good film-forming properties.

Pictograms

FlameExclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

105.8 °F - closed cup

Flash Point(C)

41 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Customers Also Viewed

2, 2, 2-Trifluoroacetophenone as an Organocatalyst for the Oxidation of Tertiary Amines and Azines to N-Oxides
Dimitris L et al.
Chemistry?A European Journal , 20, 559-563 (2014)
Asymmetric Reductions. IV. The Action of the Grignard Reagent from (+)-2-Methylbutyl Chloride on 2, 2, 2-Trifluoroacetophenone.
Mosher HS, et al.
Journal of the American Chemical Society, 78(17), 4374-4376 (1956)
Caio Cesar de Lima Silva et al.
Scientific reports, 9(1), 3901-3901 (2019-03-09)
Salicylic acid (SA) and its methyl ester, methyl salicylate (MeSA) are well known inducers of local and systemic plant defense responses, respectively. MeSA is a major mediator of systemic acquired resistance (SAR) and its conversion back into SA is thought
Synthesis and gas transport properties of new aromatic 3F polymers.
Guzman-Gutierrez MT, et al.
Journal of Membrane Science, 323(2), 379-385 (2008)
J Brunner et al.
The Journal of biological chemistry, 255(8), 3313-3318 (1980-04-25)
The synthesis of 3-trifluoromethyl-3-phenyldiazirine (TPD) is reported in an overall yield of 60% based on 2,2,2-trifluoroacetophenone as starting material. TPD is rapidly photolyzed on irradiation near 350 nm to yield 35% of the diazoisomer and 65% of the corresponding carbene.

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