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328-73-4 Usage

Chemical Properties

clear light pink to yellow liquid

Uses

3,5-bis(trifluoromethyl)pheny1- magnesium iodide was prepared from 1-iodo-3,5- bis(trifluoromethyl)benzene. Monodeprotected masked hexayne was not particularly stable and hence was used directly without purification in a Sonogashira coupling with 1-iodo-3,5-bis(trifluoromethyl)benzene to provide mono-aryl-end-capped masked hexayne.

General Description

1-Iodo-3,5-bis(trifluoromethyl)benzene is a halogenated hydrocarbon.

Check Digit Verification of cas no

The CAS Registry Mumber 328-73-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 3,2 and 8 respectively; the second part has 2 digits, 7 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 328-73:
(5*3)+(4*2)+(3*8)+(2*7)+(1*3)=64
64 % 10 = 4
So 328-73-4 is a valid CAS Registry Number.
InChI:InChI=1/C8H3F6I/c9-7(10,11)4-1-5(8(12,13)14)3-6(15)2-4/h1-3H

328-73-4 Well-known Company Product Price

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  • Alfa Aesar

  • (A10878)  1-Iodo-3,5-bis(trifluoromethyl)benzene, 97+%   

  • 328-73-4

  • 5g

  • 547.0CNY

  • Detail
  • Alfa Aesar

  • (A10878)  1-Iodo-3,5-bis(trifluoromethyl)benzene, 97+%   

  • 328-73-4

  • 25g

  • 2509.0CNY

  • Detail
  • Alfa Aesar

  • (A10878)  1-Iodo-3,5-bis(trifluoromethyl)benzene, 97+%   

  • 328-73-4

  • 100g

  • 8453.0CNY

  • Detail

328-73-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-iodo-3,5-bis(trifluoromethyl)benzene

1.2 Other means of identification

Product number -
Other names 3,5-Bis(trifluoromethyl)iodobenzene

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:328-73-4 SDS

328-73-4Synthetic route

1,3-bis(trifluoromethyl)benzene
402-31-3

1,3-bis(trifluoromethyl)benzene

3,5-bis(trifluoromethyl)iodobenzene
328-73-4

3,5-bis(trifluoromethyl)iodobenzene

Conditions
ConditionsYield
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
3,5-Bis-(trifluoromethyl)aniline
328-74-5

3,5-Bis-(trifluoromethyl)aniline

3,5-bis(trifluoromethyl)iodobenzene
328-73-4

3,5-bis(trifluoromethyl)iodobenzene

Conditions
ConditionsYield
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℃;
3,6-bis(trifluoromethyl)bromobenzene
328-70-1

3,6-bis(trifluoromethyl)bromobenzene

3,5-bis(trifluoromethyl)iodobenzene
328-73-4

3,5-bis(trifluoromethyl)iodobenzene

Conditions
ConditionsYield
With iodine; sodium iodide In acetonitrile at 20℃; for 36h; Inert atmosphere; UV-irradiation; Green chemistry;76%
1,3-bis(trifluoromethyl)benzene
402-31-3

1,3-bis(trifluoromethyl)benzene

A

3-(trifluoromethyl)benzoic acid
454-92-2

3-(trifluoromethyl)benzoic acid

B

3,5-bis(trifluoromethyl)iodobenzene
328-73-4

3,5-bis(trifluoromethyl)iodobenzene

Conditions
ConditionsYield
With sulfuric acid; iodine for 7h; Ambient temperature;A 8%
B 70%
1,3-bis(trifluoromethyl)benzene
402-31-3

1,3-bis(trifluoromethyl)benzene

A

3-iodo-5-(trifluoromethyl)benzoic acid
28186-62-1

3-iodo-5-(trifluoromethyl)benzoic acid

B

3,5-bis(trifluoromethyl)iodobenzene
328-73-4

3,5-bis(trifluoromethyl)iodobenzene

Conditions
ConditionsYield
With sulfuric acid; iodine at 55℃; for 7h;A 18%
B 52%
1-nitro-3,5-bis(trifluoromethyl)benzene
328-75-6

1-nitro-3,5-bis(trifluoromethyl)benzene

3,5-bis(trifluoromethyl)iodobenzene
328-73-4

3,5-bis(trifluoromethyl)iodobenzene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: tin (II)-chloride; aqueous hydrochloric acid / Hydrogenation
2: aqueous hydrochloric acid; sodium nitrite; potassium iodide
View Scheme
meta-sodium bisulfate

meta-sodium bisulfate

3,6-bis(trifluoromethyl)bromobenzene
328-70-1

3,6-bis(trifluoromethyl)bromobenzene

3,5-bis(trifluoromethyl)iodobenzene
328-73-4

3,5-bis(trifluoromethyl)iodobenzene

Conditions
ConditionsYield
With n-butyllithium; iodine In tetrahydrofuran; water
2-(3,5-bis-trifluoromethyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane
69807-91-6

2-(3,5-bis-trifluoromethyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

3,5-bis(trifluoromethyl)iodobenzene
328-73-4

3,5-bis(trifluoromethyl)iodobenzene

Conditions
ConditionsYield
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)phenyl)(cyano)-l3-iodanyl trifluoromethanesulfonate

(3,5-bis(trifluoromethyl)phenyl)(cyano)-l3-iodanyl trifluoromethanesulfonate

3,5-bis(trifluoromethyl)iodobenzene
328-73-4

3,5-bis(trifluoromethyl)iodobenzene

Conditions
ConditionsYield
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
126261-84-5

1-iodo-4-n-propylbenzene

3,5-bis(trifluoromethyl)phenyl carboxylic acid chloride
785-56-8

3,5-bis(trifluoromethyl)phenyl carboxylic acid chloride

A

4-propylbenzoyl chloride
52710-27-7

4-propylbenzoyl chloride

B

3,5-bis(trifluoromethyl)iodobenzene
328-73-4

3,5-bis(trifluoromethyl)iodobenzene

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In toluene at 100℃; for 12h; Time;
3,5-bis(trifluoromethyl)iodobenzene
328-73-4

3,5-bis(trifluoromethyl)iodobenzene

(2-iodo-5-methoxyphenyl)boronic acid
89694-50-8

(2-iodo-5-methoxyphenyl)boronic acid

2-(3,5-bis(trifluoromethyl)phenyl)-4-methoxyiodobenzene
1227633-25-1

2-(3,5-bis(trifluoromethyl)phenyl)-4-methoxyiodobenzene

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene at 80℃; Suzuki-Miyaura cross-coupling; Inert atmosphere; chemoselective reaction;100%
thiophene boronic acid
6165-68-0

thiophene boronic acid

3,5-bis(trifluoromethyl)iodobenzene
328-73-4

3,5-bis(trifluoromethyl)iodobenzene

1-(2-thienyl)-3,5-bis(trifluoromethyl)benzene

1-(2-thienyl)-3,5-bis(trifluoromethyl)benzene

Conditions
ConditionsYield
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
98437-23-1

benzo[b]thiophene-2-boronic acid

3,5-bis(trifluoromethyl)iodobenzene
328-73-4

3,5-bis(trifluoromethyl)iodobenzene

2-(3,5-bis-trifluoromethyl-phenyl)-benzo[b]thiophene

2-(3,5-bis-trifluoromethyl-phenyl)-benzo[b]thiophene

Conditions
ConditionsYield
With potassium carbonate; [PS-PEG-adppp-Pd(η3-C3H5)]Cl In water at 50℃; for 12h; Suzuki-Miyaura coupling;99%
(E)-1-hexenyldihydroxyborane
42599-18-8

(E)-1-hexenyldihydroxyborane

3,5-bis(trifluoromethyl)iodobenzene
328-73-4

3,5-bis(trifluoromethyl)iodobenzene

1-((E)-Hex-1-enyl)-3,5-bis-trifluoromethyl-benzene

1-((E)-Hex-1-enyl)-3,5-bis-trifluoromethyl-benzene

Conditions
ConditionsYield
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
108847-76-3

thianthren-1-yl boronic acid

3,5-bis(trifluoromethyl)iodobenzene
328-73-4

3,5-bis(trifluoromethyl)iodobenzene

1-(3,5-bis-trifluoromethyl-phenyl)-thianthrene

1-(3,5-bis-trifluoromethyl-phenyl)-thianthrene

Conditions
ConditionsYield
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
328-73-4

3,5-bis(trifluoromethyl)iodobenzene

2-Methylphenylboronic acid
16419-60-6

2-Methylphenylboronic acid

2-methyl-3',5'-bis(trifluoromethyl)biphenyl

2-methyl-3',5'-bis(trifluoromethyl)biphenyl

Conditions
ConditionsYield
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
328-73-4

3,5-bis(trifluoromethyl)iodobenzene

m-tolylboronic acid
17933-03-8

m-tolylboronic acid

3'-methyl-3,5-bis(trifluoromethyl)-1,1'-biphenyl

3'-methyl-3,5-bis(trifluoromethyl)-1,1'-biphenyl

Conditions
ConditionsYield
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
328-73-4

3,5-bis(trifluoromethyl)iodobenzene

4-methylphenylboronic acid
5720-05-8

4-methylphenylboronic acid

4’-methyl-3,5-bis(trifluoromethyl)-1,1’-biphenyl

4’-methyl-3,5-bis(trifluoromethyl)-1,1’-biphenyl

Conditions
ConditionsYield
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
328-73-4

3,5-bis(trifluoromethyl)iodobenzene

4-Chlorophenylboronic acid
1679-18-1

4-Chlorophenylboronic acid

4'-chloro-3,5-bis(trifluoromethyl)-1,1'-biphenyl

4'-chloro-3,5-bis(trifluoromethyl)-1,1'-biphenyl

Conditions
ConditionsYield
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
328-73-4

3,5-bis(trifluoromethyl)iodobenzene

4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

3,5-bis(trifluoromethyl)-4’-methoxybiphenyl

3,5-bis(trifluoromethyl)-4’-methoxybiphenyl

Conditions
ConditionsYield
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
328-73-4

3,5-bis(trifluoromethyl)iodobenzene

1-Naphthylboronic acid
13922-41-3

1-Naphthylboronic acid

1-(3,5-bis(trifluoromethyl)phenyl)naphthalene

1-(3,5-bis(trifluoromethyl)phenyl)naphthalene

Conditions
ConditionsYield
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
328-73-4

3,5-bis(trifluoromethyl)iodobenzene

4-trifluoromethylphenylboronic acid
128796-39-4

4-trifluoromethylphenylboronic acid

4-trifluoromethyl-3',5'-bis(trifluoromethyl)biphenyl
460743-64-0

4-trifluoromethyl-3',5'-bis(trifluoromethyl)biphenyl

Conditions
ConditionsYield
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
328-73-4

3,5-bis(trifluoromethyl)iodobenzene

phenylboronic acid
98-80-6

phenylboronic acid

3,5-bis(trifluoromethyl)biphenyl
336621-50-2

3,5-bis(trifluoromethyl)biphenyl

Conditions
ConditionsYield
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
1415409-75-4

3',5'-di-O-acetyl-3-buta-2,3-dien-1-ylthymidine

3,5-bis(trifluoromethyl)iodobenzene
328-73-4

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)
1426070-48-5

3,3'-{iminobis[(2Z)-3-(3,5-bis(trifluoromethyl)phenyl)but-2-ene-4,1-diyl]}bis(3',5'-di-O-acetylthymidine)

Conditions
ConditionsYield
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
624-31-7

4-tolyl iodide

3,5-bis(trifluoromethyl)iodobenzene
328-73-4

3,5-bis(trifluoromethyl)iodobenzene

(3,5-bis(trifluoromethyl)phenyl)(p-tolyl)sulfane
1262439-96-2

(3,5-bis(trifluoromethyl)phenyl)(p-tolyl)sulfane

Conditions
ConditionsYield
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
1076-38-6

4-hydroxy[1]benzopyran-2-one

1,2-propanediene
463-49-0

1,2-propanediene

3,5-bis(trifluoromethyl)iodobenzene
328-73-4

3,5-bis(trifluoromethyl)iodobenzene

3-{2-[3,5-bis(trifluoromethyl)phenyl]prop-2-en-1-yl}-4-hydroxy-2H-chromen-2-one

3-{2-[3,5-bis(trifluoromethyl)phenyl]prop-2-en-1-yl}-4-hydroxy-2H-chromen-2-one

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In acetonitrile at 65℃; under 760.051 Torr; for 20h;97%
3,5-bis(trifluoromethyl)iodobenzene
328-73-4

3,5-bis(trifluoromethyl)iodobenzene

trifluoroacetic anhydride
407-25-0

trifluoroacetic anhydride

(3,5-bis(trifluoromethyl)phenyl)-λ3-iodanediyl bis(2,2,2-trifluoroacetate)

(3,5-bis(trifluoromethyl)phenyl)-λ3-iodanediyl bis(2,2,2-trifluoroacetate)

Conditions
ConditionsYield
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;
1-(4-methoxyphenyl)-p-carborane

1-(4-methoxyphenyl)-p-carborane

3,5-bis(trifluoromethyl)iodobenzene
328-73-4

3,5-bis(trifluoromethyl)iodobenzene

1-[3,5-bis(trifluoromethyl)phenyl]-12-(4-methoxyphenyl)-p-carborane

1-[3,5-bis(trifluoromethyl)phenyl]-12-(4-methoxyphenyl)-p-carborane

Conditions
ConditionsYield
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
328-73-4

3,5-bis(trifluoromethyl)iodobenzene

1,1’-bis[3,5-bis(trifluoromethyl)phenyl]sulfide

1,1’-bis[3,5-bis(trifluoromethyl)phenyl]sulfide

Conditions
ConditionsYield
With copper(ll) sulfate pentahydrate; ethane-1,2-dithiol; potassium hydroxide In water; N,N-dimethyl-formamide at 120℃; for 18h; Inert atmosphere;96%
3,5-bis(trifluoromethyl)iodobenzene
328-73-4

3,5-bis(trifluoromethyl)iodobenzene

3,5-bis-(trifluoromethyl)phenol
349-58-6

3,5-bis-(trifluoromethyl)phenol

Conditions
ConditionsYield
With water; ethylene glycol; potassium hydroxide; copper dichloride In dimethyl sulfoxide at 120℃; for 24h; Inert atmosphere;96%
3,5-bis(trifluoromethyl)iodobenzene
328-73-4

3,5-bis(trifluoromethyl)iodobenzene

tert-butyl (3-methylbenzyl)(3-methylpyridin-2-yl)carbamate

tert-butyl (3-methylbenzyl)(3-methylpyridin-2-yl)carbamate

tert-butyl ((5-methyl-3',5'-bis(trifluoromethyl)-[1,1'-biphenyl]-3-yl)methyl)(3-methylpyridin-2-yl)carbamate

tert-butyl ((5-methyl-3',5'-bis(trifluoromethyl)-[1,1'-biphenyl]-3-yl)methyl)(3-methylpyridin-2-yl)carbamate

Conditions
ConditionsYield
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
769-42-6

1,3-dimethylbarbituric acid

1,2-propanediene
463-49-0

1,2-propanediene

3,5-bis(trifluoromethyl)iodobenzene
328-73-4

3,5-bis(trifluoromethyl)iodobenzene

5,5-bis{2-[3,5-bis(trifluoromethyl)phenyl]prop-2-en-1-yl}-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione

5,5-bis{2-[3,5-bis(trifluoromethyl)phenyl]prop-2-en-1-yl}-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione

Conditions
ConditionsYield
With caesium carbonate; tetrakis(triphenylphosphine) palladium(0) In acetonitrile at 80℃; under 750.075 Torr; for 20h;95%
o-methylphenylacetic acid
644-36-0

o-methylphenylacetic acid

3,5-bis(trifluoromethyl)iodobenzene
328-73-4

3,5-bis(trifluoromethyl)iodobenzene

2-(4-methyl-3',5'-bis(trifluoromethyl)-[1,1'-biphenyl]-3-yl)acetic acid

2-(4-methyl-3',5'-bis(trifluoromethyl)-[1,1'-biphenyl]-3-yl)acetic acid

Conditions
ConditionsYield
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%
3,5-bis(trifluoromethyl)iodobenzene
328-73-4

3,5-bis(trifluoromethyl)iodobenzene

trifluoroacetic acid
76-05-1

trifluoroacetic acid

(3,5-bis(trifluoromethyl)phenyl)-λ3-iodanediyl bis(2,2,2-trifluoroacetate)

(3,5-bis(trifluoromethyl)phenyl)-λ3-iodanediyl bis(2,2,2-trifluoroacetate)

Conditions
ConditionsYield
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
328-73-4

3,5-bis(trifluoromethyl)iodobenzene

tert-butyl ((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)(m-tolyl)carbamate

tert-butyl ((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)(m-tolyl)carbamate

tert-butyl ((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)(5 methyl-3’,5’-bis(trifluoromethyl)-[1,1’-biphenyl]-3-yl)carbamate

tert-butyl ((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)(5 methyl-3’,5’-bis(trifluoromethyl)-[1,1’-biphenyl]-3-yl)carbamate

Conditions
ConditionsYield
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%
3,5-bis(trifluoromethyl)iodobenzene
328-73-4

3,5-bis(trifluoromethyl)iodobenzene

4-nitro-aniline
100-01-6

4-nitro-aniline

C14H8F6N2O2

C14H8F6N2O2

Conditions
ConditionsYield
With silver hexafluoroantimonate; chloro[di(1-adamantyl)-2-dimethylaminophenylphosphine]gold(I) In methanol at 0 - 80℃; Inert atmosphere;94%
3,5-bis(trifluoromethyl)iodobenzene
328-73-4

3,5-bis(trifluoromethyl)iodobenzene

phenylacetylene
536-74-3

phenylacetylene

1-(3,5-bis(trifluoromethyl)phenyl)-2-phenylacetylene

1-(3,5-bis(trifluoromethyl)phenyl)-2-phenylacetylene

Conditions
ConditionsYield
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
328-73-4

3,5-bis(trifluoromethyl)iodobenzene

N-(cyclopropylmethyl)-1,1,1-trifluoromethanesulfonamide
357383-42-7

N-(cyclopropylmethyl)-1,1,1-trifluoromethanesulfonamide

N-((2-(3,5-bis(trifluoromethyl)phenyl)cyclopropyl)methyl)-1,1,1-trifluoromethanesulfonamide

N-((2-(3,5-bis(trifluoromethyl)phenyl)cyclopropyl)methyl)-1,1,1-trifluoromethanesulfonamide

Conditions
ConditionsYield
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%
3,5-bis(trifluoromethyl)iodobenzene
328-73-4

3,5-bis(trifluoromethyl)iodobenzene

propargyl 2-azidobenzoate

propargyl 2-azidobenzoate

C18H10F6N4O

C18H10F6N4O

Conditions
ConditionsYield
With cuprous oxide; caesium carbonate In water at 80℃; Sonication; Green chemistry;92%
3,5-bis(trifluoromethyl)iodobenzene
328-73-4

3,5-bis(trifluoromethyl)iodobenzene

1-iodyl-3,5-bis(trifluoromethyl)benzene

1-iodyl-3,5-bis(trifluoromethyl)benzene

Conditions
ConditionsYield
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%

328-73-4Relevant articles and documents

Direct Pd(II)-Catalyzed Site-Selective C5-Arylation of 2-Pyridone Using Aryl Iodides

Maity, Saurabh,Das, Debapratim,Sarkar, Souradip,Samanta, Rajarshi

supporting information, p. 5167 - 5171 (2018/09/13)

A straightforward Pd(II)-catalyzed general strategy was developed for the C5-selective arylation of the 2-pyridone core with easily available aryl iodides. The transformation was highly regioselective and accomplished with a wide scope and functional group tolerance. Silver nitrate played a crucial role in this direct site-selective arylation. The method was extended to synthesize biologically active molecules.

One-Pot, Metal-Free Conversion of Anilines to Aryl Bromides and Iodides

Leas, Derek A.,Dong, Yuxiang,Vennerstrom, Jonathan L.,Stack, Douglas E.

supporting information, p. 2518 - 2521 (2017/05/24)

A metal-free synthesis of aryl bromides and iodides from anilines via halogen abstraction from bromotrichloromethane and diiodomethane is described. This one-pot reaction affords aryl halides from the corresponding anilines in moderate to excellent yields without isolation of diazonium salts. The transformation has short reaction times, a simple workup, and insensitivity to moisture and air and avoids excess halogenation. DFT calculations support a SRN1 mechanism. This method represents a convenient alternative to the classic Sandmeyer reaction.

Iron(II)-catalyzed direct cyanation of arenes with aryl(cyano)iodonium triflates

Shu, Zhibin,Ji, Wenzhi,Wang, Xi,Zhou, Yujing,Zhang, Yan,Wang, Jianbo

, p. 2186 - 2189 (2014/03/21)

A direct oxidative cyanation of arenes under FeII catalysis with 3,5-di(trifluoromethyl)phenyl(cyano)iodonium triflate (DFCT) as the cyanating agent has been developed. The reaction is applicable to wide range of aromatic substrates, including polycyclic structures and heteroaromatic compounds. Copyright

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