1189352-83-7

Basic information

• Product Name: 3 - chloro - 5 - (trifluoroMethyl) benzene iodine
• Synonyms: 3 - chloro - 5 - (trifluoroMethyl) benzene iodine;3-Chloro-5-iodobenzotrifluoride;3-Chloro-5-iodo(trifluoroMethyl)benzene
• CAS NO: 1189352-83-7
• Molecular Formula: C₇H₃ClF₃I
• Molecular Weight: 306.4513996
• EINECS: -0
• Mol File: 1189352-83-7.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 217.9±35.0 °C(Predicted)
• Appearance: /
• Density: 1.952±0.06 g/cm3(Predicted)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• CAS DataBase Reference: 3 - chloro - 5 - (trifluoroMethyl) benzene iodine(CAS DataBase Reference)
• NIST Chemistry Reference: 3 - chloro - 5 - (trifluoroMethyl) benzene iodine(1189352-83-7)
• EPA Substance Registry System: 3 - chloro - 5 - (trifluoroMethyl) benzene iodine(1189352-83-7)

Safety Data

• Hazardous Substances Data: 1189352-83-7(Hazardous Substances Data)

Usage

Uses

1-Chloro-3-iodo-5-(trifluoromethyl)benzene has been used in the research of Bruton''s tyrosine kinase inhibitors through the synthesis of pyrimidinyl bipiperidine.1

Synthetic route

2-chloro-6-iodo-4-(trifluoromethyl)benzenamine (1065102-88-6) → 1-chloro-3-iodo-5-(trifluoromethyl)benzene (1189352-83-7)

Conditions	Yield
Stage #1: 2-chloro-6-iodo-4-(trifluoromethyl)benzenamine With hydrogenchloride In water at 55 - 60℃; for 0.333333h; Stage #2: With sodium nitrite In water at 0 - 5℃; for 1.66667h; Stage #3: With hypophosphorous acid In water at 5 - 35℃;	66%

trifluoroacetic acid-methyl ester (431-47-0) + 1-chloro-3-iodo-5-(trifluoromethyl)benzene (1189352-83-7) → 1-[3-chloro-5-(trifluoromethyl)phenyl]-2,2,2-trifluoroethanone (1125812-58-9)

Conditions	Yield
Stage #1: 1-chloro-3-iodo-5-(trifluoromethyl)benzene With isopropylmagnesium chloride In tetrahydrofuran at -5 - 5℃; Stage #2: trifluoroacetic acid-methyl ester In tetrahydrofuran at 0 - 5℃; Stage #3: With hydrogenchloride In tetrahydrofuran; water at 0 - 5℃;	69%

1-chloro-3-iodo-5-(trifluoromethyl)benzene (1189352-83-7) + C27H27BO3 → C28H18ClF3O

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 110℃; for 24h; Inert atmosphere;	69%

1-chloro-3-iodo-5-(trifluoromethyl)benzene (1189352-83-7) + ethyl (R)-2-pyrrolidone-5-carboxylate (68766-96-1) → ethyl 1-(3-chloro-5-(trifluoromethyl)phenyl)-5-oxopyrrolidine-2-carboxylate (1510829-97-6)

Conditions	Yield
With copper(l) iodide; caesium carbonate; N,N`-dimethylethylenediamine In 1,4-dioxane at 40℃; Inert atmosphere;

1-chloro-3-iodo-5-(trifluoromethyl)benzene (1189352-83-7) → C24H35ClF3N3O5 (1510832-47-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: copper(l) iodide; caesium carbonate; N,N`-dimethylethylenediamine / 1,4-dioxane / 40 °C / Inert atmosphere 2: diisobutylaluminium hydride / 2-methyltetrahydrofuran; n-heptane / -45 - -35 °C / Inert atmosphere 3: sodium tris(acetoxy)borohydride / dimethyl sulfoxide / 2 h / 45 - 55 °C / Inert atmosphere View Scheme

1-chloro-3-iodo-5-(trifluoromethyl)benzene (1189352-83-7) → C21H25ClF4N6O3

Conditions	Yield
Multi-step reaction with 4 steps 1: copper(l) iodide; caesium carbonate; N,N`-dimethylethylenediamine / 1,4-dioxane / 4 h / 40 °C / Inert atmosphere 2: diisobutylaluminium hydride / 2-methyltetrahydrofuran / -30 °C 3: sodium tris(acetoxy)borohydride / 2-methyltetrahydrofuran 4: hydrogenchloride / tetrahydrofuran; water View Scheme

Upstream product

• 1065102-88-6 2-chloro-6-iodo-4-(trifluoromethyl)benzenamine 

Downstream Products

• 1125812-58-9 1-(3-chloro-5-(trifluoromethyl)phenyl)-2,2,2-trifluoroethan-1-one 
• 1510829-97-6 ethyl 1-(3-chloro-5-(trifluoromethyl)phenyl)-5-oxopyrrolidine-2-carboxylate 
• 1510832-47-9 C₂₄H₃₅ClF₃N₃O₅ 
• 1510832-31-1 (3R,3‘S,4’S)-tert-butyl 3-((3-chloro-5-(trifluoromethyl)phenyl)amino)-4'-hydroxy-2-oxo-[1,3'-bipiperidine]-1'-carboxylate 
• 1510832-33-3 (3R,3‘S,4‘S)-3-((3-chloro-5-(trifluoromethyl)phenyl)amino)-4’-hydroxy-[1,3’-bipiperidin]-2-one hydrochloride 
• 1510832-36-6 C₂₁H₂₃ClF₄N₆O₂ 
• 1510832-43-5 C₂₅H₃₃ClF₄N₆O₃ 
• 1510832-70-8 C₂₃H₂₉ClF₄N₆O₃ 

Relevant articles and documents

METHOD FOR PREPARING 3-TRIFLUOROMETHYL CHALCONES

Disclosed is a method for preparing a compound of Formula 1 wherein Q and Z are as defined in the disclosure comprising distilling water from a mixture comprising a compound of Formula 2, a compound of Formula 3, a base comprising at least one compound selected from the group consisting of alkaline earth metal hydroxides of Formula 4 wherein M is Ca, Sr or Ba, alkali metal carbonates of Formula 4a wherein M1 is Li, Na or K, 1,5-diazabicyclo[4.3.0]non-5-ene and 1,8-diazabicyclo[5.4.0]undec-7-ene, and an aprotic solvent capable of forming a low-boiling azeotrope with water. Also disclosed is a method for preparing a compound of Formula 2 comprising (1) forming a reaction mixture comprising a Grignard reagent derived from contacting a compound of Formula 5 wherein X is Cl, Br or I with magnesium metal or an alkylmagnesium halide in the presence of an ethereal solvent, and then (2) contacting the reaction mixture with a compound of Formula 6 wherein Y is OR11 or NR12 R13, and R11, R12 and R13 are as defined in the disclosure. Further disclosed is a method for preparing a compound of Formula 7 wherein Q and Z are as defined in the disclosure, using a compound of Formula 1 characterized by preparing the compound of Formula 1 by the method disclosed above or using a compound of Formula 1 prepared by the method disclosed above.