Product Name

  • Name

    3,5-BIS(TRIFLUOROMETHYL)IODOBENZENE

  • EINECS
  • CAS No. 328-73-4
  • Article Data13
  • CAS DataBase
  • Density 1.904 g/cm3
  • Solubility Slightly soluble in water.
  • Melting Point
  • Formula C8H3F6I
  • Boiling Point 184 °C at 760 mmHg
  • Molecular Weight 340.007
  • Flash Point 74.4 °C
  • Transport Information
  • Appearance clear light pink to yellow liquid
  • Safety 26-36/37/39
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 328-73-4 (3,5-BIS(TRIFLUOROMETHYL)IODOBENZENE)
  • Hazard Symbols IrritantXi
  • Synonyms Benzene,5-iodo-1,3-bis(trifluoromethyl)- (8CI);1,3-Bis(trifluoromethyl)-5-iodobenzene;1-Iodo-3,5-bis(trifluoromethyl)benzene;3,5-Bis(trifluoromethyl)iodobenzene;3,5-Bis(trifluoromethyl)phenyl iodide;5-Iodo-1,3-bis(trifluoromethyl)benzene;
  • PSA 0.00000
  • LogP 4.32880

Synthetic 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%

3,5-Bis(trifluoromethyl)iodobenzene Specification

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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