Benzonitrile, 4-(trifluoromethyl)-
Completing data — refresh the page later to see the latest
Basic information
- CAS
455-18-5- Standard SMILES
N#Cc1ccc(C(F)(F)F)cc1- InChIKey
DRNJIKRLQJRKMM-UHFFFAOYSA-N- Molecular formula
- C8H4F3N
- Average molar mass
- 171.12 g/mol
- Monoisotopic mass
- 171.02958362
Names & identifiers
- Preferred name
- Benzonitrile, 4-(trifluoromethyl)-
- IUPAC
- 4-(trifluoromethyl)benzonitrile
- English name
- Trifluoro-p-tolunitrile
- Molecular formula
- C8H4F3N
- Molecular weight
- 171.12
Names & synonyms
4-(Trifluoromethyl)benzonitrile455-18-5Benzonitrile, 4-(trifluoromethyl)-4-Trifluoromethylbenzonitrilep-CyanobenzotrifluorideEINECS 207-239-1NSC 88340DTXSID50600154-Trifluoromethylbenzoic acid nitrile.alpha.,.alpha.,.alpha.-Trifluoro-p-toluonitrileRefChem:118520DTXCID9040423
Show more names
PTF-CNTrifluoro-p-tolunitr4-Cyanobenzotrifloride4-CYANOBENZOTRIFLUORIDEtrifluoro-p-tolunitrileTrifluoro-p-toluonitrile
alpha,alpha,alpha-Trifluoro-p-toluonitrileDRNJIKRLQJRKMM-UHFFFAOYSA-Nalpha,alpha,alpha-Trifluoro-p-tolunitrilep-(Trifluoromethyl)benzonitrilep-TRIFLUOROMETHYLBENZONITRILEBenzonitrile, p-(trifluoromethyl)-MFCD00001826XZK6HN6CLT
Database identifiers
- CAS
455-18-5- PubChem CID
- 67995
- DTXSID
DTXSID5060015- UNII
- XZK6HN6CLT
- EC Number
- 207-239-1
- Nikkaji
- J196.160H
Properties
Computed structural propertiesFilling in
- XLogP
- 2.9
- Topological polar surface area
- 23.8 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 0
- Heavy atoms
- 12
- Formal charge
- 0
- Complexity
- 192
Physicochemical properties
- Melting point
- 39 · 39-41 °C(lit.)
- Boiling point
- 80 · 80-81 °C20 mm Hg(lit.)
- Density
- 1.278 g/mL · 1.278 g/mL at 25 °C(lit.)
- refractive index
- 20 · n20/D 1.4583(lit.)
- Flash point
- 161 °F · 161 °F
- storage temp.
- Sealed in dry,Room Temperature
- Water Solubility
- Insoluble in water
- solubility
- soluble in Chloroform, Methanol
- form
- powder to lump to clear liquid
- Specific Gravity
- 1.278 · 1.278
- color
- White or Colorless to Light yellow
- Sensitive
- Lachrymatory
- BRN
- 2046478 · 2046478
- InChI
- 1S/C8H4F3N/c9-8(10,11)7-3-1-6(5-12)2-4-7/h1-4H
- InChIKey
- DRNJIKRLQJRKMM-UHFFFAOYSA-N
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H228 (44.3%): Flammable solid [Danger Flammable solids]；H302 (96.6%): Harmful if swallowed [Warning Acute toxicity, oral]；H312 (54.5%): Harmful in contact with skin [Warning Acute toxicity, dermal]；H315 (10.2%): Causes skin irritation [Warning Skin corrosion/irritation]；H319 (10.2%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H332 (52.3%): Harmful if inhaled [Warning Acute toxicity, inhalation]
P210, P240, P241, P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P321, P330, P332+P317, P337+P317, P362+P364, P370+P378, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 88 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
Hazard information
Regulatory Information
Status: No longer Valid Update: 26-01-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/22181
Benzonitrile, 4-(trifluoromethyl)-: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesFlam. Sol. 1 (44.3%)；Acute Tox. 4 (96.6%)；Acute Tox. 4 (54.5%)；Skin Irrit. 2 (10.2%)；Eye Irrit. 2A (10.2%)；Acute Tox. 4 (52.3%)
Regulatory information
Regulatory Information
Chemistry & industry
Uses & manufacturing
General Manufacturing InformationBenzonitrile, 4-(trifluoromethyl)-: INACTIVE
Applications
Uses4-(Trifluoromethyl)benzonitrile is used in the synthesis of quinazolines for amidines. Also used in the synthesis of s-transferase p1-1 and cancer cell proliferation.
General Description4-(Trifluoromethyl)benzonitrile is a key intermediate in the synthesis of fluvoxamine. It participates in nickel-catalyzed arylcyanation reaction of 4-octyne.
Preparation methods
Preparationnitrogen-protected flask, thermometer, and stirrer were installed. 200 mL of acetonitrile, 6.6 g (25 mmol) of triphenylphosphine, and 10 mmol of anhydrous nickel chloride (dried under vacuum at 100 °C with 2.4 g NiCl₂·6H₂O until yellow, requiring approximately 6–9 h) were added. Under nitrogen protection, the mixture was heated to reflux in an oil bath (80–82 °C) and stirred for 10 min until the solution turned dark green. The mixture was cooled to room temperature, and 4.3 g (60 mmol) of zinc powder was added. The reaction proceeded until an orange-yellow precipitate formed. The temperature was then raised to 45 °C, and the reaction proceeded for 0.5 h. 122.4 g (0.68 mol) of p-chlorotrifluorotoluene was added, and the mixture was stirred for 5 min. 44.2 g (0.68 mol) of potassium cyanide was then added, and the solution immediately turned yellow-green. The reaction was continued at this temperature with stirring. Gas chromatography monitoring showed that after 15 h, the conversion rate of p-chlorotrifluorotoluene was 82.7%, the hydrogenated dehalogenated trifluorotoluene was 0.4%, and the biphenyl product 4,4'-ditrifluoromethylbiphenyl was 0.8%. Anhydrous potassium carbonate was added and stirred for 5 min. The mixture was filtered, and the filtrate was an orange-red solution. Vacuum distillation yielded white Trifluoro-p-tolunitrile crystals.
Upstream & downstream products
Downstream products
Related reactions
37 records
Compound notes
Loading…