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368-77-4

Basic Information
CAS No.: 368-77-4
Name: 3-(Trifluoromethyl)benzonitrile
Article Data: 69
Molecular Structure:
Molecular Structure of 368-77-4 (3-(Trifluoromethyl)benzonitrile)
Formula: C8H4F3N
Molecular Weight: 171.122
Synonyms: m-Tolunitrile,a,a,a-trifluoro- (7CI,8CI);1-Cyano-3-(trifluoromethyl)benzene;NSC 88314;m-(Trifluoromethyl)benzonitrile;m-(Trifluoromethyl)cyanobenzene;a,a,a-Trifluoro-m-tolunitrile;3-Trifluoromethylbenzonitrile;
EINECS: 206-711-4
Density: 1.29 g/cm3
Melting Point: 16-20 °C(lit.)
Boiling Point: 189 °C at 760 mmHg
Flash Point: 72.2 °C
Appearance: Colorless or light yellow liquid
Hazard Symbols: HarmfulXn
Risk Codes: 20/21/22
Safety: 45-36
PSA: 23.79000
LogP: 2.57708
Synthetic route
401-81-0

m-trifluoromethylphenyl iodide

143-33-9

sodium cyanide

368-77-4

3-trifluoromethylbenzonitrile

Conditions
ConditionsYield
With sodium tetrahydroborate; zinc(II) chloride; Na2{PdCl2(Ph2P(m-C6H4SO3))2} In n-heptane; water for 3h; Heating;93%
454-89-7

3-Trifluoromethylbenzaldehyde

368-77-4

3-trifluoromethylbenzonitrile

Conditions
ConditionsYield
With ammonium hydroxide; sodium persulfate; sodium iodide; iron(II) chloride In 1,2-dichloro-ethane at 20 - 50℃; for 16h;92%
With hydroxylamine hydrochloride In methanol; water at 20℃; for 18h; Irradiation;87%
Multi-step reaction with 2 steps
1: hydroxylamine hydrochloride
2: 8 percent Chromat. / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / acetonitrile / 0.5 h / Photolysis
View Scheme
Multi-step reaction with 2 steps
1: hydroxylamine hydrochloride; potassium carbonate / 20 °C
2: potassium carbonate; fluorosulfonyl fluoride / 12 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: hydroxylamine / acetonitrile / 2 h / Reflux
2: triethylamine; fluorosulfonyl fluoride / acetonitrile / 0.5 h / 20 °C
View Scheme
401-78-5

3-bromo-1-trifluoromethylbenzene

potassiumhexacyanoferrate(II) trihydrate

368-77-4

3-trifluoromethylbenzonitrile

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); tris(2-morpholinophenyl)phosphine; potassium carbonate In water; tert-butyl alcohol at 85℃; for 5h; Schlenk technique; Inert atmosphere;89%
With tetrabutylammomium bromide; copper(II) acetate monohydrate; potassium iodide In water at 180℃; for 22h;83%
773837-37-9

sodium cyanide

401-78-5

3-bromo-1-trifluoromethylbenzene

368-77-4

3-trifluoromethylbenzonitrile

Conditions
ConditionsYield
With tri-tert-butyl phosphine; [Pd2(dba)5]; zinc In tetrahydrofuran; acetonitrile at 70℃; for 2h;88%
1423-26-3

(meta-(trifluoromethyl)phenyl)boronic acid

5-bromo-3-thiocyanatoindole

368-77-4

3-trifluoromethylbenzonitrile

Conditions
ConditionsYield
With N,N,N-trimethyl-2-(sulfooxy)ethanaminium palladium(II) chloride; sodium carbonate In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene; water for 2h;87%
2987-46-4

4-thiocyanatoaniline

1423-26-3

(meta-(trifluoromethyl)phenyl)boronic acid

368-77-4

3-trifluoromethylbenzonitrile

Conditions
ConditionsYield
With N,N,N-trimethyl-2-(sulfooxy)ethanaminium palladium(II) chloride; sodium carbonate In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene; water for 2h;87%
53515-17-6

3-(trifluoromethyl)benzothioamide

368-77-4

3-trifluoromethylbenzonitrile

Conditions
ConditionsYield
With methylene blue; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 25℃; Sealed tube; Irradiation;85%
21906-39-8

3-(trifluoromethyl)phenylacetone

368-77-4

3-trifluoromethylbenzonitrile

Conditions
ConditionsYield
With aluminum (III) chloride; sodium nitrite In N,N-dimethyl-formamide at 120℃; for 4h; Schlenk technique;84%
349-75-7

3-(trifluoromethyl)benzyl alcohol

368-77-4

3-trifluoromethylbenzonitrile

Conditions
ConditionsYield
With ammonium hydroxide; oxygen In tert-Amyl alcohol under 7500.75 Torr; for 24h; Green chemistry;83%
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; ammonium acetate; oxygen; nitric acid; acetic acid at 50℃; under 760.051 Torr; for 12h; Sealed tube;67%
With ammonium hydroxide; oxygen In tert-Amyl alcohol at 130℃; under 3750.38 Torr; for 24h;82 %Chromat.
Multi-step reaction with 3 steps
1: potassium carbonate; fluorosulfonyl fluoride; dimethyl sulfoxide / 12 h / 20 °C
2: hydroxylamine hydrochloride; potassium carbonate / 20 °C
3: potassium carbonate; fluorosulfonyl fluoride / 12 h / 20 °C
View Scheme
401-78-5

3-bromo-1-trifluoromethylbenzene

potassium ferrocyanide

368-77-4

3-trifluoromethylbenzonitrile

Conditions
ConditionsYield
With dichloro[bis{1-(dicyclohexylphosphanyl)piperidine}]palladium; sodium carbonate In 1-methyl-pyrrolidin-2-one at 140℃; for 14h; Inert atmosphere;82%
With hydrogen tetrachloropalladate; sodium phosphate In N,N-dimethyl-formamide at 120℃; for 8h; Inert atmosphere;80 %Spectr.
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Specification

The Benzonitrile,3-(trifluoromethyl)- with the CAS number 368-77-4 is also called 1-Cyano-3-(trifluoromethyl)benzene. Both the systematic name and IUPAC name are 3-(trifluoromethyl)benzonitrile. Its molecular formula is C8H4F3N. The EINECS registry number is 206-711-4. This chemical belongs to the following product categories: (1)Aromatic Nitriles; (2)Nitrile; (3)Benzotrifluoride Series.

The properties of the Benzonitrile,3-(trifluoromethyl)- are: (1)ACD/LogP: 2.56; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.56; (4)ACD/LogD (pH 7.4): 2.56; (5)ACD/BCF (pH 5.5): 51.65; (6)ACD/BCF (pH 7.4): 51.65; (7)ACD/KOC (pH 5.5): 585.91; (8)ACD/KOC (pH 7.4): 585.91; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 23.79 Å2; (13)Index of Refraction: 1.46; (14)Molar Refractivity: 36.31 cm3; (15)Molar Volume: 132.4 cm3; (16)Polarizability: 14.39×10-24cm3; (17)Surface Tension: 32 dyne/cm; (18)Enthalpy of Vaporization: 42.52 kJ/mol; (19)Vapour Pressure: 0.582 mmHg at 25°C.

Uses: This chemical can prepare 3-trifluoromethylbenzylamine. This reaction needs reagent LAH.

While using this chemical, you should be very cautious. This chemical is harmful by inhalation, in contact with skin and if swallowed. Therefore, you should take the following instructions. Firstly, you should wear suitable protective clothing, gloves and eye/face protection. Then in case of accident or if you feel unwell, you should seek medical advice immediately (show the label whenever possible).

You can still convert the following datas into molecular structure:
(1)SMILES: FC(F)(F)c1cccc(C#N)c1
(2)InChI: InChI=1/C8H4F3N/c9-8(10,11)7-3-1-2-6(4-7)5-12/h1-4H
(3)InChIKey: OGOBINRVCUWLGN-UHFFFAOYAZ