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196681

Sigma-Aldrich

4-(Trifluoromethyl)benzonitrile

99%

Synonym(s):

α,α,α-Trifluoro-p-tolunitrile

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About This Item

Linear Formula:
CF3C6H4CN
CAS Number:
Molecular Weight:
171.12
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

99%

form

solid

refractive index

n20/D 1.4583 (lit.)

bp

80-81 °C/20 mmHg (lit.)

mp

39-41 °C (lit.)

density

1.278 g/mL at 25 °C (lit.)

functional group

fluoro
nitrile

SMILES string

FC(F)(F)c1ccc(cc1)C#N

InChI

1S/C8H4F3N/c9-8(10,11)7-3-1-6(5-12)2-4-7/h1-4H

InChI key

DRNJIKRLQJRKMM-UHFFFAOYSA-N

General description

4-(Trifluoromethyl)benzonitrile is a key intermediate in the synthesis of fluvoxamine. It participates in nickel-catalyzed arylcyanation reaction of 4-octyne.

Pictograms

FlameExclamation mark

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Flam. Sol. 1

Storage Class Code

4.1B - Flammable solid hazardous materials

WGK

WGK 3

Flash Point(F)

161.6 °F - closed cup

Flash Point(C)

72 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Yasuhiro Hirata et al.
Journal of the American Chemical Society, 131(31), 10964-10973 (2009-09-03)
Allyl cyanides are found to add across alkynes in the presence of a nickel/P(4-CF(3)-C(6)H(4))(3) catalyst to give polysubstituted 2,5-hexadienenitriles with defined stereo- and regiochemistry. Use of AlMe(2)Cl or AlMe(3) as a Lewis acid cocatalyst accelerates the reaction and expands the
Improving palladium-catalyzed cyanation of aryl halides: development of a state-of-the-art methodology using potassium hexacyanoferrate (II) as cyanating agent.
Schareina T, et al.
Journal of Organometallic Chemistry, 689(24), 4576-4583 (2004)

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