3-Trifluoromethylbenzylcyanide supplier

Name
3-Trifluoromethylbenzylcyanide
EINECS 219-053-8
CAS No. 2338-76-3
Article Data20
CAS DataBase
Density 1.241 g/cm³
Solubility
Melting Point
Formula C₉H₆F₃N
Boiling Point 238.9 °C at 760 mmHg
Molecular Weight 185.149
Flash Point 48.9 °C
Transport Information UN 1993 3/PG 3
Appearance clear yellow-brown liquid
Safety 16-26-27-36/37/39
Risk Codes 10-20/21/22-36/37/38
Molecular Structure
Hazard Symbols Xn,Xi
Synonyms Acetonitrile,(a,a,a-trifluoro-m-tolyl)- (7CI,8CI);(a,a,a-Trifluoro-m-tolyl)acetonitrile;1-[3-(Trifluoromethyl)phenyl]acetonitrile;3-(Trifluoromethyl)benzyl cyanide;m-Trifluoromethylbenzyl cyanide;m-Trifluoromethylphenylacetonitrile;
PSA 23.79000
LogP 2.77148

Synthetic route

: 151-50-8
potassium cyanide

: 402-23-3
1-bromomethyl-3-trifluoromethylbenzene

: 2338-76-3
3-trifluoromethylphenylacetonitrile

Conditions

Conditions	Yield
In ethanol; water for 1.5h; Heating / reflux;	100%
In dimethyl sulfoxide

: 773837-37-9
sodium cyanide

: 705-29-3
3-Trifluoromethylbenzyl chloride

: 2338-76-3
3-trifluoromethylphenylacetonitrile

Conditions

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride In water at 55 - 65℃; for 10h; Temperature;	91%

: 98-15-7
3-chlorotrifluoromethylbenzene

: 105-56-6
ethyl 2-cyanoacetate

: 2338-76-3
3-trifluoromethylphenylacetonitrile

Conditions

Conditions	Yield
Stage #1: 3-chlorotrifluoromethylbenzene; ethyl 2-cyanoacetate With N-(2-methylnaphthalen-1-yl)-N’-(pyridin-2-ylmethyl)oxalamide; copper(I) bromide; sodium t-butanolate In isopropyl alcohol at 105℃; for 24h; Schlenk technique; Inert atmosphere; Stage #2: With water In isopropyl alcohol at 105℃; for 12h; Schlenk technique; Inert atmosphere; Cooling;	71%

: 151-50-8
potassium cyanide

: 705-29-3
3-Trifluoromethylbenzyl chloride

: 2338-76-3
3-trifluoromethylphenylacetonitrile

Conditions

Conditions	Yield
With potassium iodide In methanol

: 91322-61-1
(+/-)-ethyl cyano[3-(trifluoromethyl)phenyl]acetate

: 2338-76-3
3-trifluoromethylphenylacetonitrile

Conditions

Conditions	Yield
With sulfuric acid In water; acetic acid at 80 - 90℃; for 3h; Yield given;

: 143-33-9
sodium cyanide

: 705-29-3
3-Trifluoromethylbenzyl chloride

: 2338-76-3
3-trifluoromethylphenylacetonitrile

: C9H5F3NNa

: 2338-76-3
3-trifluoromethylphenylacetonitrile

Conditions

Conditions	Yield
With methanol In dimethyl sulfoxide at 25℃; Equilibrium constant;

: 143-33-9
sodium cyanide

: 402-23-3
1-bromomethyl-3-trifluoromethylbenzene

: 2338-76-3
3-trifluoromethylphenylacetonitrile

: 401-79-6
1-methyl-3-trifluoromethyl-benzene

: 2338-76-3
3-trifluoromethylphenylacetonitrile

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: NBS View Scheme

: 401-78-5
3-bromo-1-trifluoromethylbenzene

: 2338-76-3
3-trifluoromethylphenylacetonitrile

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: NaH, CuI / hexamethylphosphoric acid triamide / 5 h / 150 - 160 °C 2: H2SO4 / H2O; acetic acid / 3 h / 80 - 90 °C View Scheme

: 349-75-7
3-(trifluoromethyl)benzyl alcohol

: 2338-76-3
3-trifluoromethylphenylacetonitrile

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: (bromination) 2: dimethylsulfoxide View Scheme

: 402-26-6
3-(trifluoromethyl)phenylmagnesium bromide

: 2338-76-3
3-trifluoromethylphenylacetonitrile

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 2: (bromination) 3: dimethylsulfoxide View Scheme

: 705-29-3
3-Trifluoromethylbenzyl chloride

: 2338-76-3
3-trifluoromethylphenylacetonitrile

Conditions

Conditions	Yield
In dimethyl sulfoxide
In dimethyl sulfoxide
In dimethyl sulfoxide

: 22902-93-8
(α,α,α-trifluoro-m-tolyl)acetamide

: 2338-76-3
3-trifluoromethylphenylacetonitrile

Conditions

Conditions	Yield
In acetonitrile
In acetonitrile

: 107-04-0
1-Bromo-2-chloroethane

: 2338-76-3
3-trifluoromethylphenylacetonitrile

: 1-(3-(trifluoromethyl)phenyl)cyclopropane-1-carbonitrile

Conditions

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In water at 50℃;	100%
With benzyltriethylammonium bromide; sodium hydroxide In water; toluene at 0 - 20℃; for 96h; Inert atmosphere;	72%
With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In water at 50℃;

: 106-93-4
ethylene dibromide

: 2338-76-3
3-trifluoromethylphenylacetonitrile

: 1-(3-(trifluoromethyl)phenyl)cyclopropane-1-carbonitrile

Conditions

Conditions	Yield
Stage #1: 3-trifluoromethylphenylacetonitrile With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.166667h; Stage #2: ethylene dibromide In N,N-dimethyl-formamide at 20℃; for 3h;	100%

: 7521-41-7
2-Aminonicotinaldehyde

: 2338-76-3
3-trifluoromethylphenylacetonitrile

: 1082325-94-7
3-[3-(trifluoromethyl)phenyl][1,8]naphthyridin-2-amine

Conditions

Conditions	Yield
With potassium hydroxide for 0.0416667h; Microwave irradiation;	98%

: 103-80-0
phenylacetyl chloride

: 2338-76-3
3-trifluoromethylphenylacetonitrile

: 68084-26-4
(3-trifluoromethylphenyl)benzylcarbonylacetonitrile

Conditions

Conditions	Yield
With sodium t-butanolate In tetrahydrofuran at 10℃; for 24h; Reagent/catalyst; Solvent; Temperature; Autoclave;	94.1%

: 69367-52-8, 70332-52-4, 114528-93-7, 26330-51-8
methyl 2-bromo-3-methylbutanoic ester

: 2338-76-3
3-trifluoromethylphenylacetonitrile

: 1015701-13-9
methyl 2-isopropyl-3-oxo-4-(3-trifluoromethylphenyl)butyrate

Conditions

Conditions	Yield
With zinc In tetrahydrofuran for 0.5h; Heating;	94%

: 2338-76-3
3-trifluoromethylphenylacetonitrile

: 1801-10-1
3-trifluoromethylbenzamide

Conditions

Conditions	Yield
With ammonium hydroxide; ruthenium-carbon composite In tetrahydrofuran at 30℃; for 25h; Time;	94%
With ammonium hydroxide; 5 wt% ruthenium/carbon; oxygen In tetrahydrofuran at 30℃; for 25h;	94%

: 7385-85-5
naphthalen-2-yl tosylate

: 2338-76-3
3-trifluoromethylphenylacetonitrile

: 2-(naphthalen-2-yl)-2-(3-(trifluoromethyl)phenyl)acetonitrile

Conditions

Conditions	Yield
With potassium phosphate; palladium diacetate; XPhos In dichloromethane; tert-butyl alcohol at 110℃; for 4h; Inert atmosphere; Schlenk technique; Sealed tube;	93%

: 2338-76-3
3-trifluoromethylphenylacetonitrile

: 952182-78-4
2-(3-(trifluoromethyl)phenyl)ethanethioamide

Conditions

Conditions	Yield
With hydrogenchloride; O,O-Diethyl hydrogen phosphorodithioate In ethyl acetate at 20℃; Product distribution / selectivity;	92%
With hydrogenchloride; O,O-Diethyl hydrogen phosphorodithioate In ethyl acetate at 0 - 20℃;	65%

: 108-91-8
cyclohexylamine

: 2338-76-3
3-trifluoromethylphenylacetonitrile

: 418795-69-4
N-cyclohexyl-3-(trifluoromethyl)benzamide

Conditions

Conditions	Yield
With 5 wt% ruthenium/carbon; oxygen In tetrahydrofuran at 30℃; for 23h;	92%

: 2338-76-3
3-trifluoromethylphenylacetonitrile

: 533-68-6
2-bromobutyric acid ethyl ester

: 1015701-12-8
ethyl 2-ethyl-3-oxo-4-(3-trifluoromethylphenyl)butyrate

Conditions

Conditions	Yield
With zinc In tetrahydrofuran for 0.5h; Heating;	91%

: 917-54-4
methyllithium

: 3132-64-7
1,2-Epoxy-3-bromopropane

: 2338-76-3
3-trifluoromethylphenylacetonitrile

: 1432050-72-0
3-hydroxy-1-[3-(trifluoromethyl)phenyl]cyclobutanecarbonitrile

Conditions

Conditions	Yield
Stage #1: methyllithium; 3-trifluoromethylphenylacetonitrile In tetrahydrofuran; diethyl ether at -75℃; for 1h; Stage #2: 1,2-Epoxy-3-bromopropane In tetrahydrofuran; diethyl ether at -75℃; for 1h; Stage #3: With hydrogenchloride; methylmagnesium bromide In tetrahydrofuran; diethyl ether; water at -75 - 20℃;	91%

...Expand

: 3132-64-7
1,2-Epoxy-3-bromopropane

: 2338-76-3
3-trifluoromethylphenylacetonitrile

: 1432050-56-0
3-hydroxy-1-[3-(trifluoromethoxy)phenyl]cyclobutanecarbonitrile

Conditions

Conditions	Yield
Stage #1: 3-trifluoromethylphenylacetonitrile In tetrahydrofuran; diethyl ether at -75℃; for 1h; Stage #2: 1,2-Epoxy-3-bromopropane In tetrahydrofuran; diethyl ether at -75℃; for 1h; Stage #3: With hydrogenchloride; methylmagnesium bromide In tetrahydrofuran; diethyl ether; water at -75 - 20℃;	91%

: 3132-64-7
1,2-Epoxy-3-bromopropane

: 2338-76-3
3-trifluoromethylphenylacetonitrile

: 1432050-72-0
3-hydroxy-1-[3-(trifluoromethyl)phenyl]cyclobutanecarbonitrile

Conditions

Conditions	Yield
Stage #1: 3-trifluoromethylphenylacetonitrile With methyllithium In tetrahydrofuran; diethyl ether at -75℃; for 1h; Stage #2: 1,2-Epoxy-3-bromopropane In tetrahydrofuran; diethyl ether at -75℃; for 1h; Stage #3: With methylmagnesium bromide In tetrahydrofuran; diethyl ether at 20℃;	91%
Stage #1: 3-trifluoromethylphenylacetonitrile With methyllithium In tetrahydrofuran; diethyl ether at -75℃; for 1h; Stage #2: 1,2-Epoxy-3-bromopropane With methylmagnesium bromide In tetrahydrofuran; diethyl ether at -75℃; for 1h; Stage #3: With methylmagnesium bromide In tetrahydrofuran; diethyl ether at -75 - 20℃; for 16h;	91%

: 2338-76-3
3-trifluoromethylphenylacetonitrile

: 1,2,3,4-tetrahydroquinoline-8-carboxylic acid methyl ester

: 3-amino-2-(3-trifluoromethylphenyl)-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinolin-1-one

Conditions

Conditions	Yield
With pyridine; sodium t-butanolate for 6h; Reflux;	90%

: 110-89-4
piperidine

: 2338-76-3
3-trifluoromethylphenylacetonitrile

: 69001-08-7
(piperidin-1-yl)(3-(trifluoromethyl)phenyl)methanone

Conditions

Conditions	Yield
With 5 wt% ruthenium/carbon; oxygen In tetrahydrofuran at 30℃; for 21h;	88%

: 4506-71-2
ethyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate

: 2338-76-3
3-trifluoromethylphenylacetonitrile

: 2-(3-(trifluoromethyl)phenyl)-5,6,7,8-tetrahydrothieno[2,3-d]pyrimidin-4(3H)-one

Conditions

Conditions	Yield
With hydrogenchloride In 1,4-dioxane at 20℃; for 18h;	88%

: 2338-76-3
3-trifluoromethylphenylacetonitrile

: 351-35-9
3-(trifluoromethyl)phenylacetic acid

Conditions

Conditions	Yield
Stage #1: 3-trifluoromethylphenylacetonitrile With sodium hydroxide; water Heating / reflux; Stage #2: With hydrogenchloride In water pH=2;	87%
With sodium hydroxide In ethanol
With sulfuric acid; acetic acid

: 90-02-8
salicylaldehyde

: 98-59-9
p-toluenesulfonyl chloride

: 2338-76-3
3-trifluoromethylphenylacetonitrile

: 4-methyl-N-(3-(3-(trifluoromethyl)phenyl)-2H-chromen-2-ylidene)benzenesulfonamide

Conditions

Conditions	Yield
Stage #1: salicylaldehyde; 3-trifluoromethylphenylacetonitrile With 1,4-diaza-bicyclo[2.2.2]octane In 2-methyltetrahydrofuran at 80℃; for 8h; Reflux; Stage #2: p-toluenesulfonyl chloride With 1,4-diaza-bicyclo[2.2.2]octane In 2-methyltetrahydrofuran at 0℃;	87%

...Expand

: 2338-76-3
3-trifluoromethylphenylacetonitrile

: C18H8F6N2

Conditions

Conditions	Yield
With 5% active carbon-supported ruthenium; potassium carbonate In 1,2-dichloro-benzene at 160℃; for 35h;	87%
With methanol; iodine; sodium In diethyl ether at -78 - 0℃; for 2.25h; Inert atmosphere;	65%

: 708-76-9
2-hydroxy-4,6-dimethoxybenzaldehyde

: 2338-76-3
3-trifluoromethylphenylacetonitrile

: 5,7-dimethoxy-3-(3'-trifluoromethylphenyl)iminocoumarin

Conditions

Conditions	Yield
With Amberlite IRA 900 (OH-) In cyclohexane for 15h; Condensation; Heating;	85%

: 111-44-4
3-oxa-1,5-dichloropentane

: 2338-76-3
3-trifluoromethylphenylacetonitrile

: 1035261-83-6
4-(3-(trifluoromethyl)phenyl)-tetrahydro-2H-pyran-4-carbonitrile

Conditions

Conditions	Yield
In N,N-dimethyl-formamide; mineral oil at 20 - 55℃; for 21.5h; Inert atmosphere;	85%
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20 - 55℃; for 21.5h;	85%
Stage #1: 3-trifluoromethylphenylacetonitrile With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.5h; Cooling with ice; Stage #2: 3-oxa-1,5-dichloropentane In N,N-dimethyl-formamide at 0℃; for 0.5h;	84%
Stage #1: 3-trifluoromethylphenylacetonitrile With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 0.5h; Cooling with ice; Stage #2: 3-oxa-1,5-dichloropentane In N,N-dimethyl-formamide at 20℃; for 2h; Stage #3: With lithium chloride In N,N-dimethyl-formamide	84%
Stage #1: 3-trifluoromethylphenylacetonitrile With potassium tert-butylate In N,N-dimethyl-formamide at 0℃; for 0.166667h; Stage #2: 3-oxa-1,5-dichloropentane In N,N-dimethyl-formamide at 0 - 20℃; for 6h;

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

: 2338-76-3
3-trifluoromethylphenylacetonitrile

: 90238-10-1
N,N-dimethyl 3-(trifluoromethyl)benzamide

Conditions

Conditions	Yield
With copper(I) oxide; 1,10-Phenanthroline; oxygen; toluene-4-sulfonic acid at 140℃; under 760.051 Torr; for 24h; Sealed tube;	84%

: 100-51-6
benzyl alcohol

: 2338-76-3
3-trifluoromethylphenylacetonitrile

: 3-phenyl-2-(3-(trifluoromethyl)phenyl)propanamide

Conditions

Conditions	Yield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; triphenylphosphine; potassium hydroxide In tert-Amyl alcohol at 130℃; for 2h; Microwave irradiation;	84%
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; triphenylphosphine; potassium hydroxide at 130℃; for 2h; Microwave irradiation; Green chemistry;	84%

: 616-38-6
carbonic acid dimethyl ester

: 2338-76-3
3-trifluoromethylphenylacetonitrile

: methyl (3-trifluoromethylphenyl)cyanoacetate

Conditions

Conditions	Yield
With sodium methylate In methanol; toluene at 75 - 80℃; for 12h;	83%

: 90-02-8
salicylaldehyde

: 2338-76-3
3-trifluoromethylphenylacetonitrile

: 3-(3-(trifluoromethyl)phenyl)-2H-chromen-2-imine

Conditions

Conditions	Yield
Stage #1: salicylaldehyde With amberlite IRA-900 form OH In toluene at 85℃; for 3h; Inert atmosphere; Stage #2: 3-trifluoromethylphenylacetonitrile In toluene for 12h; Reflux; Inert atmosphere;	83%

: 370563-61-4
4-[(E)-2-{4-[(E)-2-(4-formylphenyl)ethenyl]-2,5-bis(octyloxy)phenyl}ethenyl]benzaldehyde

: 2338-76-3
3-trifluoromethylphenylacetonitrile

: (2Z)-3-[4-{(E)-2-[4-{(E)-2-[4-{(Z)-2-cyano-2-[3-(trifluoromethyl)phenyl]ethenyl}phenyl]ethenyl}-2,5-bis(octyloxy)phenyl]ethenyl}phenyl]-2-[3-(trifluoromethyl)phenyl]-2-propenenitrile

Conditions

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran; tert-butyl alcohol	79%
Knoevenagel condensation;

triethylbenzylammonium chloride (TEBA): triethylbenzylammonium chloride (TEBA)

: 106-93-4
ethylene dibromide

: 2338-76-3
3-trifluoromethylphenylacetonitrile

: 1-(3-(trifluoromethyl)phenyl)cyclopropane-1-carbonitrile

Conditions

Conditions	Yield
With sodium hydroxide	79%

...Expand

: 10290-91-2
naphthalen-2-yl methanesulfonate

: 2338-76-3
3-trifluoromethylphenylacetonitrile

: 2-(naphthalen-2-yl)-2-(3-(trifluoromethyl)phenyl)acetonitrile

Conditions

Conditions	Yield
With potassium phosphate; palladium diacetate; XPhos In dichloromethane; tert-butyl alcohol at 110℃; for 4h; Inert atmosphere; Schlenk technique; Sealed tube;	79%

3-Trifluoromethylbenzylcyanide Chemical Properties

The Molecular formula of m-TRIFLUOROMETHYLPHENYLACETONITRILE(2338-76-3):C₉H₆F₃N
The Molecular Weight of m-TRIFLUOROMETHYLPHENYLACETONITRILE(2338-76-3): 185.15
The Molecular Structure of m-TRIFLUOROMETHYLPHENYLACETONITRILE(2338-76-3) is
Density:1.241 g/cm³
Boiling point: 238.9 ^°C at 760 mmHg
Flash point: 48.9 ^°C
Solubility in water:insoluble
Refractive index (nD): 1.457
Molar Refractivity: 40.69 cm³
Polarizability: 16.13 10-24cm³
Surface Tension: 30.1 dyne/cm
Enthalpy of Vaporization: 47.58 kJ/mol
Vapour Pressure: 0.0413 mmHg at 25^°C
Appearance:Colorless oily liquid, fishy odor
IUPAC Name:2-[3-(trifluoromethyl)phenyl]acetonitrile
Synonyms:(alpha,alpha,alpha-trifluoro-m-tolyl)-acetonitril;3-Trifluormethylbenzylcyanide;(alpha,alpha,alpha-Trifluoro-m-tolyl)acetonitrile;3-(trifluoromethyl)-benzeneacetonitril;3-(Trifluoromethyl)benzeneacetonitrile;Acetonitrile, (alpha,alpha,alpha-trifluoro-m-tolyl)-;2-[3-(TRIFLUOROMETHYL)PHENYL]ACETONITRILE;1-(3-(TRIFLUOROMETHYL)PHENYL)ACETONITRILE

3-Trifluoromethylbenzylcyanide Uses

Used as a pesticide, medicine, dye intermediate used for synthesis of herbicides, herbicides, synthetic anti-bacteria, or other coronary vasodilator.Besides,it's used to synthetic pesticides, pharmaceuticals, dyes intermediates.

3-Trifluoromethylbenzylcyanide Toxicity Data With Reference

Organism: mouse
Test Type:LD50
Route:intraperitoneal
Reported Dose (Normalized Dose) :100mg/kg (100mg/kg)
Source: National Technical Information Service. Vol. AD691-490,

3-Trifluoromethylbenzylcyanide Consensus Reports

Cyanide and its compounds are on the Community Right-To-Know List. Reported in EPA TSCA Inventory.

3-Trifluoromethylbenzylcyanide Safety Profile

Poison by intraperitoneal route. When heated to decomposition it emits very toxic fumes of F⁻, NO_x, and CN⁻. See also NITRILES.
Hazard Codes Xn,Xi
Xn：Harmful
Xi：Irritant
Risk Statements 10-20/21/22-36/37/38
R10:Flammable.
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin .
Safety Statements 16-26-27-36/37/39
S16:Keep away from sources of ignition - No smoking .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S27:Take off immediately all contaminated clothing .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
RIDADR：UN 1993 3/PG 3
WGK Germany：3
RTECS：CY1820000
Hazard Note: Irritant
TSCA：T
HazardClass：3
PackingGroup ：III

Product Name

3-Trifluoromethylbenzylcyanide

Synthetic route

3-Trifluoromethylbenzylcyanide Chemical Properties

3-Trifluoromethylbenzylcyanide Uses

3-Trifluoromethylbenzylcyanide Toxicity Data With Reference

3-Trifluoromethylbenzylcyanide Consensus Reports

3-Trifluoromethylbenzylcyanide Safety Profile

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