118-83-2

Basic information

• Product Name: 5-Chloro-2-nitrobenzotrifluoride
• Synonyms: Benzene, 4-chloro-1-nitro-2-(trifluoromethyl)-;TIMTEC-BB SBB009905;4-CHLORO-1-NITRO-2-(TRIFLUOROMETHYL)BENZENE;4-NITRO-3-TRIFLUOROMETHYLCHLOROBENZENE;3-CHLORO-6-NITROBENZOTRIFLUORIDE;5-CHLORO-2-NITRO-A,A,A-TRIFLUOROTOLUENE;5-CHLORO-2-NITRO-ALPHA,ALPHA,ALPHA-TRIFLUOROTOLUENE;5-CHLORO-2-NITROBENZOTRIFLUORIDE
• CAS NO: 118-83-2
• Molecular Formula: C₇H₃ClF₃NO₂
• Molecular Weight: 225.55
• EINECS: 204-280-7
• Mol File: 118-83-2.mol
• Article Data: 1

Chemical Properties

• Melting Point: 21 °C
• Boiling Point: 222-224 °C
• Flash Point: 217 °F
• Appearance: colorless to light yellow liquid
• Density: 1.526 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0933mmHg at 25°C
• Refractive Index: n20/D 1.499(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility: 168 mg/L (20 ºC)
• BRN: 1973477
• CAS DataBase Reference: 5-Chloro-2-nitrobenzotrifluoride(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Chloro-2-nitrobenzotrifluoride(118-83-2)
• EPA Substance Registry System: 5-Chloro-2-nitrobenzotrifluoride(118-83-2)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-28-36/39-36/37/39-36
• RIDADR: 2810
• WGK Germany: 2
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 118-83-2(Hazardous Substances Data)

Usage

Chemical Properties

colorless to light yellow liquid

InChI:InChI=1/C7H3ClF3NO2/c8-4-1-2-6(12(13)14)5(3-4)7(9,10)11/h1-3H

Synthetic route

1-nitroso-2-(trifluoromethyl)benzene → 5-chloro-2-nitrotrifluoromethylbenzene (118-83-2)

Conditions	Yield
Stage #1: 1-nitroso-2-(trifluoromethyl)benzene With 2,6-di-tert-butyl-4-methyl-phenol; copper dichloride In acetonitrile at 20℃; under 760.051 Torr; for 2h; Stage #2: With Oxone In water; acetonitrile at 20℃; under 760.051 Torr; for 24h; regioselective reaction;	49%

4-nitro-3-(trifluoromethyl)benzeneamine (393-11-3) → 5-chloro-2-nitrotrifluoromethylbenzene (118-83-2)

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

3-chlorotrifluoromethylbenzene (98-15-7) → 5-chloro-2-nitrotrifluoromethylbenzene (118-83-2)

Conditions	Yield
With nitric acid
With sulfuric acid; nitric acid
With sulfuric acid; nitric acid
With nitric acid

nitric acid (7697-37-2) + 3-chlorotrifluoromethylbenzene (98-15-7) → 5-chloro-2-nitrotrifluoromethylbenzene (118-83-2) + 6-chloro-2-trifluoromethylnitrobenzene (386-70-9)

sulfuric acid (7664-93-9) + nitric acid (7697-37-2) + 3-chlorotrifluoromethylbenzene (98-15-7) → 5-chloro-2-nitrotrifluoromethylbenzene (118-83-2) + 6-chloro-2-trifluoromethylnitrobenzene (386-70-9)

5-chloro-2-nitrotrifluoromethylbenzene (118-83-2) + phenylacetylene (536-74-3) → 1-Nitro-4-phenylethynyl-2-trifluoromethyl-benzene

Conditions	Yield
With copper(l) iodide; cis,cis,cis-tetrakis[(diphenylphosphanyl)methyl]cyclopentane; potassium carbonate; bis(η3-allyl-μ-chloropalladium(II)) In N,N-dimethyl-formamide at 100℃; for 20h;	91%

(2-methylpropyl)-propanedioic acid, diethyl ester (10203-58-4) + 5-chloro-2-nitrotrifluoromethylbenzene (118-83-2) → diethyl 2-isobutyl-2-(4-nitro-3-(trifluoromethyl)phenyl)malonate (1168133-76-3)

Conditions	Yield
Stage #1: (2-methylpropyl)-propanedioic acid, diethyl ester With sodium hydride In N,N-dimethyl-formamide at 0 - 25℃; Cooling with ice bath; Stage #2: 5-chloro-2-nitrotrifluoromethylbenzene In N,N-dimethyl-formamide at 20 - 25℃; for 48h;	87%
Stage #1: (2-methylpropyl)-propanedioic acid, diethyl ester With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 0.666667h; Stage #2: 5-chloro-2-nitrotrifluoromethylbenzene In N,N-dimethyl-formamide; mineral oil at 20℃; for 48h;	87%

5-chloro-2-nitrotrifluoromethylbenzene (118-83-2) + methylamine (74-89-5) → N-methyl-4'-nitro-3'-(trifluoromethyl)aniline (52807-22-4)

Conditions	Yield
With sodium carbonate In ethanol at 70℃; for 36h;	87%

ethyl acetohydroximate (10576-12-2) + 5-chloro-2-nitrotrifluoromethylbenzene (118-83-2) → C11H11F3N2O4

Conditions	Yield
With sodium hydroxide In N,N-dimethyl-formamide at 30℃; for 1.5h; Sonication;	86%

methanol (67-56-1) + 5-chloro-2-nitrotrifluoromethylbenzene (118-83-2) → 4-methoxy-1-nitro-2-(trifluoromethyl)benzene (344-39-8)

Conditions	Yield
With sodium at 20℃; for 6h;	81.4%

5-chloro-2-nitrotrifluoromethylbenzene (118-83-2) + 2-(3,4-dimethoxyphenyl)-ethylamine (120-20-7) → N-[2-(3,4-dimethoxyphenyl)ethyl]-4-nitro-3-(trifluoromethyl)aniline (1215018-67-9)

Conditions	Yield
With sodium carbonate In acetonitrile for 16h; Reflux;	76%

5-chloro-2-nitrotrifluoromethylbenzene (118-83-2) → 4-methoxy-1-nitro-2-(trifluoromethyl)benzene (344-39-8)

Conditions	Yield
With sodium methylate In methanol; dichloromethane; water	75%
With sodium methylate In methanol for 15h; Heating / reflux;

5-chloro-2-nitrotrifluoromethylbenzene (118-83-2) + sodium p-chlorobenzenesulphinate (14752-66-0) → 2,5-bis(4-chlorobenzenesulphonyl)benzotrifluoride (150690-64-5)

Conditions	Yield
In N,N-dimethyl acetamide at 140℃; for 0.25h;	74%
In N,N-dimethyl acetamide for 0.25h; Heating;

5-chloro-2-nitrotrifluoromethylbenzene (118-83-2) + N,N,N',N'-tetramethylguanidine (80-70-6) → N,N-dimethyl-4-nitro-3-(trifluoromethyl)aniline

Conditions	Yield
at 20 - 100℃;	71%

methyl-n-propylamine (627-35-0) + 5-chloro-2-nitrotrifluoromethylbenzene (118-83-2) → N-methyl-4-nitro-N-propyl-3-(trifluoromethyl)aniline

Conditions	Yield
With sodium carbonate In ethanol at 70℃; for 36h;	70%

[1,2-bis(diphenylphosphino)ethane]tricarbonylruthenium (58201-22-2) + 5-chloro-2-nitrotrifluoromethylbenzene (118-83-2) → Ru(1,2-bis(diphenylphosphino)ethane)(CO)2[η(2)-ON-4-chloro-2-(trifluoromethyl)phenyl] + carbon dioxide (124-38-9)

Conditions	Yield
In tetrahydrofuran inert atmosphere; standing (10-15 min); concn. (vac.), cooling (-78°C), addn. hexane, filtn., washing(hexane), drying (N2 or vac.); elem. anal.;	A 68% B n/a

Ru(CO)3(bis(2,6-iPr2C6H3-imino)acenaphthene) (221324-87-4) + 5-chloro-2-nitrotrifluoromethylbenzene (118-83-2) → Ru(CO)2(bis(2,6-iPr2C6H3-imino)acenaphthene)(η(2)-ONC6H3-4-Cl,2-CF3)

Conditions	Yield
In toluene N2 atmosphere; 0°C, stirring (3 h); evapn. to dryness (room temp.), suspn. (hexane), filtration, drying (vac.), elem. anal.;	67%

5-chloro-2-nitrotrifluoromethylbenzene (118-83-2) + 1-amino-pent-4-yne (15252-44-5) → (4-nitro-3-(trifluoromethyl)phenyl)pent-4-yn-1-ylamine

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 85℃; for 24h; Sealed tube;	65%

5-chloro-2-nitrotrifluoromethylbenzene (118-83-2) + Trimethylenediamine (109-76-2) → N-(3-aminopropyl)-3-(trifluoromethyl)-4-nitrobenzenamine (1032995-12-2)

Conditions	Yield
With potassium carbonate In acetonitrile for 72h; Reflux;	60%
Stage #1: Trimethylenediamine With sodium carbonate In ethanol for 0.25h; Reflux; Stage #2: 5-chloro-2-nitrotrifluoromethylbenzene In ethanol for 72h; Reflux;	45%
With sodium carbonate In ethanol for 72h; Heating;

5-chloro-2-nitrotrifluoromethylbenzene (118-83-2) + 2-hydroxy-2-methylpropanenitrile (75-86-5) → 4-nitro-3-trifluoromethylbenzonitrile (320-36-5)

Conditions	Yield
With [Pd(cinnamyl)Cl]2; N-ethyl-N,N-diisopropylamine; XPhos In isopropyl alcohol at 80℃; for 2h; Inert atmosphere;	55%

5-chloro-2-nitrotrifluoromethylbenzene (118-83-2) + tert-butyl N-(6-aminohexyl)carbamate (51857-17-1) → C18H26F3N3O4

Conditions	Yield
With sodium carbonate In acetonitrile for 19h; Reflux;	52%

5-chloro-2-nitrotrifluoromethylbenzene (118-83-2) + 3-hydroxy-5-tert-butylisoxazole (107403-12-3) → 5-t-butyl-2-(4-nitro-3-trifluoromethylphenyl)-4-isoxazolin-3-one (119116-37-9)

Conditions	Yield
With potassium carbonate; dimethyl sulfoxide	18.7%

5-chloro-2-nitrotrifluoromethylbenzene (118-83-2) → 4-chloro-2-(trifluoromethyl)aniline (445-03-4)

Conditions	Yield
With hydrogenchloride; tin

5-chloro-2-nitrotrifluoromethylbenzene (118-83-2) + 4-methyl-3-n-propylsulfinylphenol (49828-98-0) → C17H16F3NO4S (49828-52-6)

Conditions	Yield
With potassium hydroxide In N,N-dimethyl acetamide

5-chloro-2-nitrotrifluoromethylbenzene (118-83-2) + 4-Chloro-3-propylsulfanyl-phenol (49828-89-9) → C16H13ClF3NO3S (49828-41-3)

Conditions	Yield
With potassium hydroxide In N,N-dimethyl acetamide

5-chloro-2-nitrotrifluoromethylbenzene (118-83-2) + 3-propylsulfinyl-4-chlorophenol (49828-97-9) → C16H13ClF3NO4S (49828-66-2)

Conditions	Yield
With potassium hydroxide In N,N-dimethyl acetamide

5-chloro-2-nitrotrifluoromethylbenzene (118-83-2) + 3-propylsulfonyl-4-methylphenol (49828-99-1) → C17H16F3NO5S (49828-81-1)

Conditions	Yield
With potassium hydroxide In N,N-dimethyl acetamide

5-chloro-2-nitrotrifluoromethylbenzene (118-83-2) + 4-Chloro-3-(propane-1-sulfonyl)-phenol (49829-01-8) → C16H13ClF3NO5S (49828-67-3)

Conditions	Yield
With potassium hydroxide In N,N-dimethyl acetamide

5-chloro-2-nitrotrifluoromethylbenzene (118-83-2) + 3-Ethanesulfinyl-4-methyl-phenol → C16H14F3NO4S (49828-83-3)

Conditions	Yield
With potassium hydroxide In N,N-dimethyl acetamide

5-chloro-2-nitrotrifluoromethylbenzene (118-83-2) + 3-Ethylsulfanyl-4-methyl-phenol → C16H14F3NO3S (49828-82-2)

Conditions	Yield
With potassium hydroxide In N,N-dimethyl acetamide

5-chloro-2-nitrotrifluoromethylbenzene (118-83-2) + 4-Methyl-3-(n-propylthio)phenol → C17H16F3NO3S (49828-48-0)

Conditions	Yield
With potassium hydroxide In N,N-dimethyl acetamide

5-chloro-2-nitrotrifluoromethylbenzene (118-83-2) + Diethyl methylmalonate (609-08-5) → diethyl α-methyl-α-(3-trifluoromethyl-4-nitrophenyl)-malonate (58809-98-6)

Conditions	Yield
With sodium hydride 1.) DMF, 30 min, room temperature, 2.) DMF; Yield given. Multistep reaction;
In dimethylformamide-toluene; water; toluene; mineral oil

Upstream product

• 7664-93-9 sulfuric acid 
• 7697-37-2 nitric acid 
• 98-15-7 3-chlorotrifluoromethylbenzene 
• 393-11-3 4-nitro-3-(trifluoromethyl)benzeneamine 

Downstream Products

• 150690-64-5 2,5-bis(4-chlorobenzenesulphonyl)benzotrifluoride 
• 61587-18-6 Cyclohexyl-(4-nitro-3-trifluoromethyl-phenyl)-amine 
• 61587-16-4 (4-Ethoxy-phenyl)-(4-nitro-3-trifluoromethyl-phenyl)-amine 
• 363-95-1 4,4'-dinitro-3,3'-bis-trifluoromethyl-biphenyl 
• 41512-62-3 N,N-dimethyl-4-nitro-3-(trifluoromethyl)aniline 
• 344-39-8 4-methoxy-1-nitro-2-(trifluoromethyl)benzene 
• 119116-37-9 5-t-butyl-2-(4-nitro-3-trifluoromethylphenyl)-4-isoxazolin-3-one 
• 16588-69-5 4-chloro-2-trifluoromethylphenylisocyanate 
• 5188-07-8 sodium thiomethoxide 
• 320-36-5 4-nitro-3-trifluoromethylbenzonitrile 
• 49828-48-0 C₁₇H₁₆F₃NO₃S 
• 49828-82-2 C₁₆H₁₄F₃NO₃S 
• 49828-83-3 C₁₆H₁₄F₃NO₄S 
• 49828-67-3 C₁₆H₁₃ClF₃NO₅S 

Relevant articles and documents

Para-Selective Halogenation of Nitrosoarenes with Copper(II) Halides

The para-selective direct bromination and chlorination of nitrosoarenes with copper(II) bromide and chloride is reported. Under mild reaction conditions, a range of halogenated arylnitroso compounds are obtained in moderate to good yields with high regioselectivity. Additionally, the versatility of the method is demonstrated by the development of a one-pot procedure to obtain the corresponding para-halogenated aniline- and nitrobenzene derivatives.