Conditions | Yield |
---|---|
With sulfuric acid; iodine; fluorine In 1,1,2-Trichloro-1,2,2-trifluoroethane Ambient temperature; | 83% |
Multi-step reaction with 3 steps 1: disulfuric acid; sulfuric acid; nitric acid 2: tin (II)-chloride; aqueous hydrochloric acid / Hydrogenation 3: aqueous hydrochloric acid; sodium nitrite; potassium iodide View Scheme | |
Multi-step reaction with 2 steps 1: (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4′-di-(tert-butyl)-2,2′-bipyridyl / tetrahydrofuran / 24 h / 80 °C / High pressure; Inert atmosphere 2: 1,10-Phenanthroline; copper(l) iodide; potassium iodide / methanol; water / 3 h / 80 °C / High pressure View Scheme |
Conditions | Yield |
---|---|
Stage #1: 3,5-Bis-(trifluoromethyl)aniline With diiodomethane; sodium nitrite In dichloromethane; water at 23℃; for 0.0833333h; Stage #2: With acetic acid In dichloromethane; water at 23℃; for 1h; | 82% |
With hydrogenchloride; potassium iodide; sodium nitrite | |
(i) NaNO2, aq. HCl, (ii) CuI; Multistep reaction; | |
Stage #1: 3,5-Bis-(trifluoromethyl)aniline With toluene-4-sulfonic acid In acetonitrile at 20℃; for 0.166667h; Stage #2: With potassium iodide; sodium nitrite In water; acetonitrile at 0 - 20℃; |
Conditions | Yield |
---|---|
With iodine; sodium iodide In acetonitrile at 20℃; for 36h; Inert atmosphere; UV-irradiation; Green chemistry; | 76% |
1,3-bis(trifluoromethyl)benzene
A
3-(trifluoromethyl)benzoic acid
B
3,5-bis(trifluoromethyl)iodobenzene
Conditions | Yield |
---|---|
With sulfuric acid; iodine for 7h; Ambient temperature; | A 8% B 70% |
1,3-bis(trifluoromethyl)benzene
A
3-iodo-5-(trifluoromethyl)benzoic acid
B
3,5-bis(trifluoromethyl)iodobenzene
Conditions | Yield |
---|---|
With sulfuric acid; iodine at 55℃; for 7h; | A 18% B 52% |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: tin (II)-chloride; aqueous hydrochloric acid / Hydrogenation 2: aqueous hydrochloric acid; sodium nitrite; potassium iodide View Scheme |
Conditions | Yield |
---|---|
With n-butyllithium; iodine In tetrahydrofuran; water |
2-(3,5-bis-trifluoromethyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane
3,5-bis(trifluoromethyl)iodobenzene
Conditions | Yield |
---|---|
With copper(l) iodide; 1,10-Phenanthroline; potassium iodide In methanol; water at 80℃; for 3h; High pressure; | 0.266 g |
3,5-bis(trifluoromethyl)iodobenzene
Conditions | Yield |
---|---|
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; iron(II) acetate In 1,2-dichloro-ethane at 20℃; for 4h; Inert atmosphere; Sealed tube; |
1-iodo-4-n-propylbenzene
3,5-bis(trifluoromethyl)phenyl carboxylic acid chloride
A
4-propylbenzoyl chloride
B
3,5-bis(trifluoromethyl)iodobenzene
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In toluene at 100℃; for 12h; Time; |
3,5-bis(trifluoromethyl)iodobenzene
(2-iodo-5-methoxyphenyl)boronic acid
2-(3,5-bis(trifluoromethyl)phenyl)-4-methoxyiodobenzene
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene at 80℃; Suzuki-Miyaura cross-coupling; Inert atmosphere; chemoselective reaction; | 100% |
Conditions | Yield |
---|---|
With potassium carbonate; [PS-PEG-adppp-Pd(η3-C3H5)]Cl In water at 50℃; for 12h; Suzuki-Miyaura coupling; | 99% |
benzo[b]thiophene-2-boronic acid
3,5-bis(trifluoromethyl)iodobenzene
Conditions | Yield |
---|---|
With potassium carbonate; [PS-PEG-adppp-Pd(η3-C3H5)]Cl In water at 50℃; for 12h; Suzuki-Miyaura coupling; | 99% |
(E)-1-hexenyldihydroxyborane
3,5-bis(trifluoromethyl)iodobenzene
Conditions | Yield |
---|---|
With potassium carbonate; [PS-PEG-adppp-Pd(η3-C3H5)]Cl In water at 50℃; for 12h; Suzuki-Miyaura coupling; | 99% |
thianthren-1-yl boronic acid
3,5-bis(trifluoromethyl)iodobenzene
Conditions | Yield |
---|---|
With potassium carbonate; [PS-PEG-adppp-Pd(η3-C3H5)]Cl In water at 50℃; for 12h; Suzuki-Miyaura coupling; | 99% |
3,5-bis(trifluoromethyl)iodobenzene
2-Methylphenylboronic acid
Conditions | Yield |
---|---|
With potassium carbonate; [PS-PEG-adppp-Pd(η3-C3H5)]Cl In water at 50℃; for 12h; Suzuki-Miyaura coupling; | 99% |
3,5-bis(trifluoromethyl)iodobenzene
m-tolylboronic acid
Conditions | Yield |
---|---|
With potassium carbonate; [PS-PEG-adppp-Pd(η3-C3H5)]Cl In water at 50℃; for 12h; Suzuki-Miyaura coupling; | 99% |
Conditions | Yield |
---|---|
With potassium carbonate; [PS-PEG-adppp-Pd(η3-C3H5)]Cl In water at 50℃; for 12h; Suzuki-Miyaura coupling; | 99% |
Conditions | Yield |
---|---|
With potassium carbonate; [PS-PEG-adppp-Pd(η3-C3H5)]Cl In water at 50℃; for 12h; Suzuki-Miyaura coupling; | 99% |
Conditions | Yield |
---|---|
With potassium carbonate; [PS-PEG-adppp-Pd(η3-C3H5)]Cl In water at 50℃; for 12h; Suzuki-Miyaura coupling; | 99% |
With potassium phosphate monohydrate; 4,4'-di-tBu-2,2'-dipyridylpalladium(II) dichloride In methanol; water at 80℃; for 2h; Suzuki-Miyaura Coupling; | 94% |
3,5-bis(trifluoromethyl)iodobenzene
1-Naphthylboronic acid
Conditions | Yield |
---|---|
With potassium carbonate; [PS-PEG-adppp-Pd(η3-C3H5)]Cl In water at 50℃; for 12h; Suzuki-Miyaura coupling; | 99% |
3,5-bis(trifluoromethyl)iodobenzene
4-trifluoromethylphenylboronic acid
4-trifluoromethyl-3',5'-bis(trifluoromethyl)biphenyl
Conditions | Yield |
---|---|
With potassium carbonate; [PS-PEG-adppp-Pd(η3-C3H5)]Cl In water at 50℃; for 12h; Suzuki-Miyaura coupling; | 99% |
3,5-bis(trifluoromethyl)iodobenzene
phenylboronic acid
3,5-bis(trifluoromethyl)biphenyl
Conditions | Yield |
---|---|
With potassium carbonate; [PS-PEG-adppp-Pd(η3-C3H5)]Cl In water at 50℃; for 12h; Suzuki-Miyaura coupling; | 99% |
With potassium phosphate monohydrate; 4,4'-di-tBu-2,2'-dipyridylpalladium(II) dichloride In methanol; water at 80℃; for 2h; Suzuki-Miyaura Coupling; | 97% |
Stage #1: 3,5-bis(trifluoromethyl)iodobenzene; phenylboronic acid With potassium phosphate In 1,2-dimethoxyethane at 80℃; for 6h; Suzuki-Miyaura Coupling; Inert atmosphere; Stage #2: In 1,2-dimethoxyethane; water at 100℃; for 10h; | 91% |
3',5'-di-O-acetyl-3-buta-2,3-dien-1-ylthymidine
3,5-bis(trifluoromethyl)iodobenzene
3,3'-{iminobis[(2Z)-3-(3,5-bis(trifluoromethyl)phenyl)but-2-ene-4,1-diyl]}bis(3',5'-di-O-acetylthymidine)
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); trifuran-2-yl-phosphane; ammonium tartrate; potassium carbonate In 1,4-dioxane; N,N-dimethyl-formamide at 100℃; for 8h; stereoselective reaction; | 99% |
4-tolyl iodide
3,5-bis(trifluoromethyl)iodobenzene
(3,5-bis(trifluoromethyl)phenyl)(p-tolyl)sulfane
Conditions | Yield |
---|---|
Stage #1: 4-tolyl iodide With copper(ll) sulfate pentahydrate; ethane-1,2-dithiol; potassium hydroxide In water; dimethyl sulfoxide at 100℃; for 8h; Inert atmosphere; Stage #2: 3,5-bis(trifluoromethyl)iodobenzene In water; dimethyl sulfoxide; N,N-dimethyl-formamide at 120℃; for 18h; Inert atmosphere; | 98% |
Stage #1: 4-tolyl iodide With copper(ll) sulfate pentahydrate; ethane-1,2-dithiol; potassium hydroxide In water; dimethyl sulfoxide at 100 - 110℃; for 8h; Inert atmosphere; Stage #2: 3,5-bis(trifluoromethyl)iodobenzene In water; dimethyl sulfoxide; N,N-dimethyl-formamide at 120℃; for 18h; Inert atmosphere; | 98% |
4-hydroxy[1]benzopyran-2-one
1,2-propanediene
3,5-bis(trifluoromethyl)iodobenzene
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In acetonitrile at 65℃; under 760.051 Torr; for 20h; | 97% |
Conditions | Yield |
---|---|
Stage #1: trifluoroacetic anhydride With dihydrogen peroxide In dichloromethane; water at -50℃; for 0.166667h; Stage #2: 3,5-bis(trifluoromethyl)iodobenzene In dichloromethane; water at 15℃; for 14h; | 97% |
With dihydrogen peroxide In dichloromethane at -50 - 15℃; for 16h; Schlenk technique; Inert atmosphere; |
3,5-bis(trifluoromethyl)iodobenzene
Conditions | Yield |
---|---|
With BuLi; CuCl; pyridine In pyridine; 1,2-dimethoxyethane; hexane (N2); addn. of BuLi in hexanes to the p-carborane derivative in DME withstirring, addn. of pyridine and CuCl with vigorous stirring, reflux (ca . 30 min), addn. of the aryl iodide, gentle reflux (95-100°C, 24 h); addn. of Et2O/H2O, set aside (overnight), sepn. of a solid, recrystn. (EtOH); elem. anal.; | 96% |
3,5-bis(trifluoromethyl)iodobenzene
Conditions | Yield |
---|---|
With copper(ll) sulfate pentahydrate; ethane-1,2-dithiol; potassium hydroxide In water; N,N-dimethyl-formamide at 120℃; for 18h; Inert atmosphere; | 96% |
Conditions | Yield |
---|---|
With water; ethylene glycol; potassium hydroxide; copper dichloride In dimethyl sulfoxide at 120℃; for 24h; Inert atmosphere; | 96% |
3,5-bis(trifluoromethyl)iodobenzene
Conditions | Yield |
---|---|
With methyl bicyclo[2.2.1]hept-2-ene-2-carboxylate; silver(I) acetate; palladium diacetate; 3-(trifluoromethyl)pyridine-2-(1H)-one In chloroform at 100℃; for 24h; | 96% |
1,3-dimethylbarbituric acid
1,2-propanediene
3,5-bis(trifluoromethyl)iodobenzene
Conditions | Yield |
---|---|
With caesium carbonate; tetrakis(triphenylphosphine) palladium(0) In acetonitrile at 80℃; under 750.075 Torr; for 20h; | 95% |
Conditions | Yield |
---|---|
With dipotassium hydrogenphosphate; methyl bicyclo[2.2.1]hept-2-ene-2-carboxylate; (3r,5r,7r)-N-(2-hydroxy-5-(trifluoromethyl)pyridin-3-yl)adamantane-1-carboxamide; palladium diacetate; silver carbonate at 100℃; for 24h; | 95% |
Conditions | Yield |
---|---|
With Oxone In chloroform at 20℃; for 1.5h; | 94% |
With dipotassium peroxodisulfate In dichloromethane at 36 - 38℃; for 20h; | 36% |
3,5-bis(trifluoromethyl)iodobenzene
Conditions | Yield |
---|---|
With N-(2-hydroxypyridin-3-yl)acetamide; methyl bicyclo[2.2.1]hept-2-ene-2-carboxylate; silver(I) acetate; palladium diacetate In 1,2-dichloro-ethane at 100℃; for 24h; | 94% |
Conditions | Yield |
---|---|
With silver hexafluoroantimonate; chloro[di(1-adamantyl)-2-dimethylaminophenylphosphine]gold(I) In methanol at 0 - 80℃; Inert atmosphere; | 94% |
Conditions | Yield |
---|---|
With sodium hydroxide In methanol at 80℃; for 12h; Sonogashira Cross-Coupling; Schlenk technique; | 92% |
With potassium phosphate tribasic trihydrate In methanol at 80℃; for 4h; Sonogashira coupling; Inert atmosphere; | 90% |
With palladium diacetate; potassium carbonate In ethanol at 80℃; for 24h; | 87% |
With [{Pd(μ-Cl){κ2-P,C-P(iPr)2(OC6H3-2-Ph)}}2]; triethylamine In water at 40℃; for 4h; Sonogashira coupling; Inert atmosphere; | 83% |
With [Cu(DMEDA)2]Cl2*H2O; caesium carbonate; N,N`-dimethylethylenediamine In 1,4-dioxane; methanol at 135℃; for 22h; Castro-Stephens reaction; Inert atmosphere; |
3,5-bis(trifluoromethyl)iodobenzene
N-(cyclopropylmethyl)-1,1,1-trifluoromethanesulfonamide
Conditions | Yield |
---|---|
With t-Boc-L-valine; sodium 2,2,2-trifluoroacetate; palladium diacetate; silver carbonate In tert-butyl alcohol at 80℃; for 18h; Sealed tube; enantioselective reaction; | 92% |
Conditions | Yield |
---|---|
With cuprous oxide; caesium carbonate In water at 80℃; Sonication; Green chemistry; | 92% |
3,5-bis(trifluoromethyl)iodobenzene
Conditions | Yield |
---|---|
Stage #1: 3,5-bis(trifluoromethyl)iodobenzene With peracetic acid In acetic acid at 40℃; for 1h; Stage #2: ruthenium trichloride In water; acetic acid at 40℃; for 16h; | 91% |
Stage #1: 3,5-bis(trifluoromethyl)iodobenzene With dihydrogen peroxide; acetic anhydride at 40℃; for 1h; Inert atmosphere; Stage #2: With ruthenium trichloride In water at 40℃; for 16h; Inert atmosphere; | 91% |
The 3,5-Bis(trifluoromethyl)iodobenzene with cas registry number of 328-73-4 belongs to the categories in Fluoro-contained Iodo series; Aromatic Hydrocarbons (substituted) & Derivatives; Miscellaneous; Aryl; C8; Halogenated Hydrocarbons. Both its systematic name and IUPAC name are the same which is called 1-iodo-3,5-bis(trifluoromethyl)benzene. This chemical is sensitive to light with appearance of clear light pink to yellow liquid. It is incompatible with strong oxidizing agents.
The physical properties about this chemical are: (1)ACD/LogP: 5.07; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 5.07; (4)ACD/LogD (pH 7.4): 5.07; (5)ACD/BCF (pH 5.5): 4224.81; (6)ACD/BCF (pH 7.4): 4224.81; (7)ACD/KOC (pH 5.5): 13707.13; (8)ACD/KOC (pH 7.4): 13707.13; (9)#H bond acceptors: 0; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Index of Refraction: 1.462; (13)Molar Refractivity: 49.11 cm3; (14)Molar Volume: 178.5 cm3; (15)Surface Tension: 24.5 dyne/cm; (16)Density: 1.904 g/cm3; (17)Flash Point: 74.4 °C; (18)Enthalpy of Vaporization: 40.3 kJ/mol; (19)Boiling Point: 184 °C at 760 mmHg; (20)Vapour Pressure: 1.03 mmHg at 25°C ; (21)Refractive index: 1.463.
Preparation of 3,5-Bis(trifluoromethyl)iodobenzen: it can be made by 1,3-bis-trifluoromethyl-benzene with reagents F2, I2, 98percent aq. H2SO4 and solvent 1,1,2-trichloro-1,2,2-trifluoro-ethane at ambient temperature. The yield is about 83%.
Uses of 3,5-Bis(trifluoromethyl)iodobenzene: this chemical can react with trifluoro-peroxyacetic acid to prepare other chemcial with solvent CH2Cl2 at temperature of -78 deg C up to RT. The yield is about 68%.
When you are using this chemical, please be cautious about it as the following:
Wear suitable protective clothing, gloves and eye/face protection during you are using it for this chemical is irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
(1)SMILES: FC(F)(F)c1cc(cc(I)c1)C(F)(F)F;
(2)InChI: InChI=1/C8H3F6I/c9-7(10,11)4-1-5(8(12,13)14)3-6(15)2-4/h1-3H;
(3)InChIKey: VDPIZIZDKPFXLI-UHFFFAOYAN
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