Benzonitrile, 4-(trifluoromethyl)-

HCID 67995CAS 455-18-5
Substructure searchFind similar structures

Basic information

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 properties

XLogP
2.9
Topological polar surface area
23.8 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
4
Rotatable bonds
0
Heavy atoms
12

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

Safety & regulation

GHS classification

GHS Classification · 5 items

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 · 2 items

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 · 2 items

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

Safety data

PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
3
tsca
TSCA listed
ridadr
UN 1325 4.1/PG 2
hs_code
29269095
risk_code
20/21/22-11

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 · 1 item

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

Suppliers50 total

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
青岛和兴精细化学有限公司0532-66915948
山东德信精细化工有限公司18553366272
INTATRADE GmbH+49 3493/605464 · [email protected]

Related reactions

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Linked notes

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