98-15-7

Basic information

• Product Name: 3-Chlorobenzotrifluoride
• Synonyms: 1-(trifluoromethyl)-3-chlorobenzene;1-Chlor-3-trifluormethyl-benzol;1-chloro-3-(trifluoromethyl)-benzen;3-Chlorbenzotrifluorid;3-Chlor-α,α,α-trifluortoluol;benzene,1-chloro-3-(trifluoromethyl)-;Benzotrifluoride,3-chloro;chlorobenzotrifluorides
• CAS NO: 98-15-7
• Molecular Formula: C₇H₄ClF₃
• Molecular Weight: 180.55
• EINECS: 202-642-9
• Product Categories: Trifluoromethylbenzene serise;Aromatic Hydrocarbons (substituted) & Derivatives;Miscellaneous;Chlorine Compounds;Fluorine Compounds;Aryl;Building Blocks;C7;Chemical Synthesis;Halogenated Hydrocarbons;Organic Building Blocks
• Mol File: 98-15-7.mol
• Article Data: 20

Chemical Properties

• Melting Point: -55.4 °C
• Boiling Point: 137-138 °C(lit.)
• Flash Point: 97 °F
• Appearance: clear colourless liquid
• Density: 1.336 g/mL at 25 °C
• Vapor Pressure: 9.37mmHg at 25°C
• Refractive Index: n20/D 1.446(lit.)
• Water Solubility: <0.1 g/100 mL at 22℃
• BRN: 510215
• CAS DataBase Reference: 3-Chlorobenzotrifluoride(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Chlorobenzotrifluoride(98-15-7)
• EPA Substance Registry System: 3-Chlorobenzotrifluoride(98-15-7)

Safety Data

• Hazard Codes: Xi,F
• Statements: 10-36/37/38
• Safety Statements: 16-26-36-24/25
• RIDADR: UN 2234 3/PG 3
• WGK Germany: 1
• RTECS: XS9142000
• TSCA: T
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 98-15-7(Hazardous Substances Data)

Usage

Chemical Properties

CLEAR COLOURLESS LIQUID

Uses

Different sources of media describe the Uses of 98-15-7 differently. You can refer to the following data:
1. Intermediate in manufacturing of dyes and pharmaceuticals, dielectrics, insecticides.
2. 3-Chlorobenzotrifluoride is used as an intermediate in organic synthesis, pharmaceuticals, agrochemicals and dyestuff.

General Description

A water-white liquid with an odor like moth balls. Flash point between 65-108°F. Insoluble in water and denser than water. Toxic by inhalation. Liquid contact may irritate skin and eyes.

Air & Water Reactions

Highly flammable. On contact with water 3-Chlorobenzotrifluoride can evolve hydrogen fluoride, a highly toxic and corrosive gas. [AAR, 1999]. Insoluble in water and denser than water.

Fire Hazard

HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.

Purification Methods

Purify it as for o-chlorobenzotrifluoride above. 20 1.4432. [Beilstein 5 III 692, 5 IV 814.]

InChI:InChI=1/C7H4ClF3/c8-6-3-1-2-5(4-6)7(9,10)11/h1-4H

Synthetic route

3-(trifluoromethyl)benzoic acid (454-92-2) → 3-chlorotrifluoromethylbenzene (98-15-7)

Conditions	Yield
With trichloroisocyanuric acid; bromine In tetrachloromethane at -10 - 100℃; for 18h; Photolysis;	100%

3-iodochlorobenzene (625-99-0) + 1,10-phenanthroline trifluoroacetic acid cuprous (I) → 3-chlorotrifluoromethylbenzene (98-15-7)

Conditions	Yield
With sodium fluoride In N,N-dimethyl-formamide at 140℃; for 8h; Inert atmosphere; Sealed tube;	77%

3-Trifluoromethylphenol (98-17-9) → 3-chlorotrifluoromethylbenzene (98-15-7)

Conditions	Yield
With phenylphosphorus tetrachloride at 160℃;	70%

C21H4ClF29O4Pb (102644-91-7) → 3-chlorotrifluoromethylbenzene (98-15-7)

Conditions	Yield
With trifluoroacetic acid	50%

α,α,α-trifluorotoluene (98-08-8) → 1,2-dichloro-4-(trifluoromethyl)benzene (328-84-7) + 1,4-dichloro-2-trifluoromethylbenzene (320-50-3) + 1,3-dichloro-5-(trifluoromethyl)benzene (54773-20-5) + 1,2-dichloro-3-(trifluoromethyl)benzene (54773-19-2) + 3-chlorotrifluoromethylbenzene (98-15-7)

Conditions	Yield
With chlorine; iron(III) chloride at 80℃; Product distribution;	A 15.6% B 35.6% C 2.2% D 8.9% E 37.1%

α,α,α-trifluorotoluene (98-08-8) → 3-chlorotrifluoromethylbenzene (98-15-7)

Conditions	Yield
With chlorine; iron(III) chloride
With lead(IV) acetate; C6F13COOH; trifluoroacetic acid; lithium chloride Yield given. Multistep reaction;
With lead(IV) acetate; perfluoroheptanoic acid; trifluoroacetic acid; lithium chloride 1.)80 deg C, 7 h 2.)r.t., 1 h; Yield given. Multistep reaction;
With O2N-C6H4-S(=NSO2CF3)2Cl at 22℃; for 96h;

3-trifluoromethylaniline (98-16-8) → 3-chlorotrifluoromethylbenzene (98-15-7)

Conditions	Yield
With hydrogenchloride Diazotization.Behandlung der Diazoniumsalz-Loesung mit CuCl oder CuSO4 in der Waerme;

3-trifluoromethylaniline (98-16-8) → 3-Trifluoromethylphenol (98-17-9) + 3-chlorotrifluoromethylbenzene (98-15-7)

Conditions	Yield
With hydrogenchloride Diazotization.Eintragen der Diazoniumsalz-Loesung in siedende wss. CuSO4-Loesung;

benzoyl chloride (98-88-4) → 3-chlorotrifluoromethylbenzene (98-15-7)

Conditions	Yield
With sulfur tetrafluoride; hydrogen fluoride at 120℃;
With sulfur tetrafluoride; hydrogen fluoride at 120℃; for 6h;
With sulfur tetrafluoride; hydrogen fluoride at 120℃;

Benzotrichlorid (98-07-7) → 3-chlorotrifluoromethylbenzene (98-15-7)

Conditions	Yield
With antimony (V)-fluoride chloride; phosphorus pentachloride; chlorine Einleiten von HF;

2,3,5-trichlorotrifluoromethylbenzene (61841-46-1) → 3-chlorotrifluoromethylbenzene (98-15-7)

Conditions	Yield
With Dichloromethylsilane at 240℃; (electron irradiation);

Upstream product

• 106-46-7 para-dichlorobenzene 
• 421-83-0 trifluoromethane sulfonyl chloride 
• 108-90-7 chlorobenzene 
• 1885-46-7 trifluoromethanesulfonic acid difluoromethyl ether 
• 1416277-01-4 (3-chlorophenyl)(mesityl)iodonium trifluoromethanesulfonate 
• 625-99-0 3-iodochlorobenzene 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 93683-27-3 perfluoro-2,4-dimethyl-3-ethylpent-3-yl radical 
• 77152-08-0 trifluoromethylcopper(I) 
• 108-41-8 1-chloro-3-methylbenzene 
• 55642-42-7 bis(trifluoromethyl)tellurium 
• 10026-13-8 phosphorus pentachloride 
• 7664-39-3 hydrogen fluoride 
• 7782-50-5 chlorine 

Downstream Products

• 23228-45-7 2-chloro-4-(trifluoromethyl)benzoic acid 
• 2376-00-3 2-chloro-6-(trifluoromethyl)benzoic acid 
• 203915-48-4 (3-trifluoromethylphenyl)-4-trifluormethylphenylmethanol 
• 118-83-2 5-chloro-2-nitrotrifluoromethylbenzene 
• 386-70-9 6-chloro-2-trifluoromethylnitrobenzene 
• 194873-98-8 4-(3-trifluoromethylphenyl)anisole 
• 938187-84-9 N-ferrocenyl-3-(trifluoromethyl)aniline 
• 651014-92-5 C₂₄H₂₆BF₆NO₃ 
• 380611-49-4 [2-chloro-6-(trifluoromethyl)benzene]lithium 
• 401-80-9 3-fluoro-trifluoromethylbenzene 
• 1188445-87-5 2-chloro-4-(trifluoromethyl)benzaldehyde oxime 
• 1188445-88-6 2-chloro-N-hydroxy-4-(trifluoromethyl)benzimidoyl chloride 
• 1188445-89-7 methyl 3-(2-chloro-4-(trifluoromethyl)phenyl)-5-methylisoxazole-4-carboxylate 
• 2923-40-2 [m-(trifluoromethyl)phenyl]magnesium chloride 

Relevant articles and documents

Cathodic C-H Trifluoromethylation of Arenes and Heteroarenes Enabled by an in Situ-Generated Triflyltriethylammonium Complex

While several trifluoromethylation reactions involving the electrochemical generation of CF3 radicals via anodic oxidation have been reported, the alternative cathodic, reductive radical generation has remained elusive. Herein, the first cathodic trifluoromethylation of arenes and heteroarenes is reported. The method is based on the electrochemical reduction of an unstable triflyltriethylammonium complex generated in situ from inexpensive triflyl chloride and triethylamine, which produces CF3 radicals that are trapped by the arenes on the cathode surface.

Copper-mediated trifluoromethylation of diaryliodonium salts with difluoromethyltriflate

The reaction of diaryliodonium salts with difluoromethyltriflate in the presence of TBAT and CuTC gave the corresponding trifluoromethylated arenes in moderate yields. Compared to other difluorocarbene-derived trifluoromethylation reactions, the current one proceeded at mild reaction conditions (room temperature) within short reaction time (5 min).

Copper-mediated trifluoromethylation of diaryliodonium salts with TMSCF3 at room temperature

A convenient method for the preparation of trifluoromethylated arenes from the reaction of diaryliodonium salts with TMSCF3 in the presence of CuBF4·(MeCN)4 and KF at room temperature within 25 min was developed. This reaction provides a valuable complement to the previously established trifluoromethylation methods.