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2-(4-Fluorophenyl)thiophene
Cas No: 58861-48-6
No Data 100 Gram 5 Metric Ton/Month Hebei Maison Chemical Co.,Ltd Contact Supplier
2-(4-Fluorophenyl)thiophene Manufacturer/High quality/Best price/In stock
Cas No: 58861-48-6
USD $ 3.0-3.0 / Kilogram 1 Kilogram 1-100 Metric Ton/Month Dayang Chem (Hangzhou) Co.,Ltd. Contact Supplier
High quality 2-(4-Fluorophenyl)thiophene with high purity
Cas No: 58861-48-6
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High purity Various Specifications 2-(4-Fluorophenyl)thiophene CAS:58861-48-6
Cas No: 58861-48-6
USD $ 100.0-500.0 / Gram 1 Gram 99999 Gram/Year Hangzhou Dingyan Chem Co., Ltd Contact Supplier
58861-48-6 Thiophene,2-(4-fluorophenyl)-
Cas No: 58861-48-6
USD $ 40.0-50.0 / Gram 1 Gram 1000 Metric Ton/Day WUHAN MULEI NEW MATERIAL CO., LTD Contact Supplier
Factory supply high quality 2-(4-Fluorophenyl)thiophene,58861-48-6
Cas No: 58861-48-6
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58861-48-6 2-(4-FLUOROPHENYL)THIOPHENE
Cas No: 58861-48-6
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2-(4-Fluorophenyl)-thiophene
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2-(4-FLUOROPHENYL)THIOPHEN
Cas No: 58861-48-6
USD $ 1.0-1.0 / Kilogram 1 Kilogram 1000 Kilogram/Month Enke Pharma-tech Co.,Ltd. (Cangzhou, China ) Contact Supplier
2-(4-Fluorophenyl)thiophene
Cas No: 58861-48-6
USD $ 1.0-1.0 / Kilogram 1 Kilogram 1000 Metric Ton/Year Henan Sinotech Import&Export Corporation Contact Supplier

58861-48-6 Usage

Chemical Properties

white solid
InChI:InChI=1/C10H7FS/c11-9-5-3-8(4-6-9)10-2-1-7-12-10/h1-7H

58861-48-6SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-(4-Fluorophenyl)thiophene

1.2 Other means of identification

Product number -
Other names 2-(4-FLUOROPHENYL)THIOPHENE

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:58861-48-6 SDS

58861-48-6Synthetic route

2-bromothiophene
1003-09-4

2-bromothiophene

4-fluoroboronic acid
1765-93-1

4-fluoroboronic acid

2-(4-fluorophenyl)thiophene
58861-48-6

2-(4-fluorophenyl)thiophene

Conditions
ConditionsYield
With Tedicyp; potassium carbonate; bis(η3-allyl-μ-chloropalladium(II)) In xylene at 130℃; for 20h; Suzuki cross-coupling reaction;95%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In N,N-dimethyl-formamide at 120℃; for 15h; Inert atmosphere;85%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water at 25 - 75℃; Inert atmosphere;82.5%
2-bromothiophene
1003-09-4

2-bromothiophene

4-flourophenylmagnesium bromide
352-13-6

4-flourophenylmagnesium bromide

2-(4-fluorophenyl)thiophene
58861-48-6

2-(4-fluorophenyl)thiophene

Conditions
ConditionsYield
Stage #1: 2-bromothiophene With 1,2-bis(diphenylphosphino)ethane nickel(II) chloride In tetrahydrofuran at 2℃; for 0.666667h;
Stage #2: 4-flourophenylmagnesium bromide In tetrahydrofuran at 10 - 23℃; for 1.66667h;
Stage #3: With acetic acid In tetrahydrofuran; water at 7℃; for 0.75h;
95%
Stage #1: 2-bromothiophene; 1,3-bis-(diphenylphosphino)propane; palladium diacetate In tetrahydrofuran at 50℃; for 0.0833333h; Inert atmosphere;
Stage #2: 4-flourophenylmagnesium bromide In tetrahydrofuran at 60℃; for 7h;
Stage #3: With hydrogenchloride In tetrahydrofuran; water at 30℃; Cooling with ice;
2-Iodothiophene
3437-95-4

2-Iodothiophene

4-fluoroboronic acid
1765-93-1

4-fluoroboronic acid

2-(4-fluorophenyl)thiophene
58861-48-6

2-(4-fluorophenyl)thiophene

Conditions
ConditionsYield
With potassium carbonate In water; N,N-dimethyl-formamide at 100℃; under 2585.81 Torr; for 0.333333h; Suzuki reaction; Microwave irradiation;94%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In Dimethyl ether; water at 100℃; for 0.5h; Microwave irradiation;86.1%
With potassium carbonate; Pd-N-heterocyclic carbene-organic silica In water; N,N-dimethyl-formamide at 100℃; for 0.16h; Suzuki reaction; microwave irradiation;91 % Chromat.
thiophene boronic acid
6165-68-0

thiophene boronic acid

1-Bromo-4-fluorobenzene
460-00-4

1-Bromo-4-fluorobenzene

2-(4-fluorophenyl)thiophene
58861-48-6

2-(4-fluorophenyl)thiophene

Conditions
ConditionsYield
With potassium carbonate; tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine In ethanol; water at 90℃; Inert atmosphere;92%
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In toluene at 90℃; for 0.5h; Schlenk technique; Inert atmosphere;92%
With C33H48Cl2N4O9Pd; oxygen; potassium carbonate In water at 80℃; Suzuki-Miyaura Coupling;85%
Stage #1: thiophene boronic acid; 1-Bromo-4-fluorobenzene With sodium carbonate In water; N,N-dimethyl-formamide at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: With tetrakis(triphenylphosphine) palladium(0) In water; N,N-dimethyl-formamide at 85℃; for 3.03333h; Inert atmosphere;
82%
2-bromothiophene
1003-09-4

2-bromothiophene

1-Bromo-4-fluorobenzene
460-00-4

1-Bromo-4-fluorobenzene

2-(4-fluorophenyl)thiophene
58861-48-6

2-(4-fluorophenyl)thiophene

Conditions
ConditionsYield
Stage #1: 1-Bromo-4-fluorobenzene With iodine; magnesium In tetrahydrofuran at 36 - 40℃; for 4h; Inert atmosphere;
Stage #2: 2-bromothiophene With 1,2-bis(diphenylphosphino)ethane nickel(II) chloride In tetrahydrofuran at 20 - 25℃; for 5h; Temperature; Solvent; Inert atmosphere;
91.3%
Stage #1: 2-bromothiophene With magnesium In tetrahydrofuran at 30 - 45℃; Inert atmosphere;
Stage #2: 1-Bromo-4-fluorobenzene With tetrakis(triphenylphosphine)nickel(0) In tetrahydrofuran at 60 - 80℃; for 6h; Inert atmosphere;
Stage #3: With sulfuric acid In tetrahydrofuran; water at 40 - 60℃; pH=2.2; Reagent/catalyst;
87.6%
Stage #1: 2-bromothiophene With magnesium In tetrahydrofuran at 30 - 45℃; for 2h; Inert atmosphere; Sealed tube;
Stage #2: 1-Bromo-4-fluorobenzene With tetrakis(triphenylphosphine)nickel(0) In tetrahydrofuran at 60 - 80℃; for 6h; Kumada Cross-Coupling; Inert atmosphere;
Stage #3: With water at 40 - 60℃; Reagent/catalyst;
87.6%
Stage #1: 1-Bromo-4-fluorobenzene With magnesium In tetrahydrofuran; ethylene dibromide for 1.5h; Inert atmosphere;
Stage #2: 2-bromothiophene With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In tetrahydrofuran at 10 - 75℃; for 0.5h;
75%
Stage #1: 1-Bromo-4-fluorobenzene With magnesium In 2-Me-THF Reflux; Inert atmosphere;
Stage #2: 2-bromothiophene; 1,2-bis(diphenylphosphino)ethane nickel(II) chloride In 2-Me-THF at 2 - 22℃; Inert atmosphere;
Stage #3: With acetic acid In 2-Me-THF; water for 0.25h; Inert atmosphere;
2-thienyl chloride
96-43-5

2-thienyl chloride

4-fluoroboronic acid
1765-93-1

4-fluoroboronic acid

2-(4-fluorophenyl)thiophene
58861-48-6

2-(4-fluorophenyl)thiophene

Conditions
ConditionsYield
With potassium phosphate tribasic trihydrate; C31H41P; palladium diacetate In tetrahydrofuran at 110℃; for 3h; Suzuki-Miyaura Coupling; Inert atmosphere;91%
With C27H39Br2N3Pd; potassium hydroxide In isopropyl alcohol at 82℃; for 0.166667h; Suzuki-Miyaura Coupling;87%
1-ethoxythiocarbonylsulfanyl-4-(4-fluorophenyl)-4-oxobutyl 2,2-dimethylpropionate
517867-11-7

1-ethoxythiocarbonylsulfanyl-4-(4-fluorophenyl)-4-oxobutyl 2,2-dimethylpropionate

2-(4-fluorophenyl)thiophene
58861-48-6

2-(4-fluorophenyl)thiophene

Conditions
ConditionsYield
With acetic acid; potassium iodide at 110℃; for 0.0833333h; Microwave irradiation;88%
Multi-step reaction with 2 steps
1: titanium tetrachloride / dichloromethane / 0 - 20 °C / Inert atmosphere
2: silica gel / neat (no solvent) / 215 °C / Inert atmosphere
View Scheme
4-fluoro-1-iodobenzene
352-34-1

4-fluoro-1-iodobenzene

triethyl(thiophen-2-yl)germane

triethyl(thiophen-2-yl)germane

2-(4-fluorophenyl)thiophene
58861-48-6

2-(4-fluorophenyl)thiophene

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); silver tetrafluoroborate In N,N-dimethyl-formamide at 80℃; for 16h; chemoselective reaction;88%
2-bromothiophene
1003-09-4

2-bromothiophene

2-(4-fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
214360-58-4

2-(4-fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

2-(4-fluorophenyl)thiophene
58861-48-6

2-(4-fluorophenyl)thiophene

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In Dimethyl ether; water at 70 - 75℃;87%
thiophene boronic acid
6165-68-0

thiophene boronic acid

4-fluoro-1-iodobenzene
352-34-1

4-fluoro-1-iodobenzene

2-(4-fluorophenyl)thiophene
58861-48-6

2-(4-fluorophenyl)thiophene

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; N,N-dimethyl-formamide at 85℃; Inert atmosphere;86%
With tetrakis(triphenylphosphine) palladium(0) In water; N,N-dimethyl-formamide at 85℃; Inert atmosphere;86%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; N,N-dimethyl-formamide at 85℃; for 3h;86%
4-(4-fluorophenyl)-4-oxopropionic acid
366-77-8

4-(4-fluorophenyl)-4-oxopropionic acid

2-(4-fluorophenyl)thiophene
58861-48-6

2-(4-fluorophenyl)thiophene

Conditions
ConditionsYield
With tetraphosphorus decasulfide In toluene for 0.5h; Microwave irradiation;85%
5-(4-fluorophenyl)thiophene-2-carboxaldehyde
249504-38-9

5-(4-fluorophenyl)thiophene-2-carboxaldehyde

2-(4-fluorophenyl)thiophene
58861-48-6

2-(4-fluorophenyl)thiophene

Conditions
ConditionsYield
With Pd-γ-Fe2O3 In cyclohexane at 130℃; for 24h; Inert atmosphere; Molecular sieve; Sealed tube;83%
C10H8BrF

C10H8BrF

2-(4-fluorophenyl)thiophene
58861-48-6

2-(4-fluorophenyl)thiophene

Conditions
ConditionsYield
With potassium sulfide; iodine In N,N-dimethyl-formamide at 110℃; for 11.8h; Inert atmosphere; chemoselective reaction;76%
C26H37FOS

C26H37FOS

2-(4-fluorophenyl)thiophene
58861-48-6

2-(4-fluorophenyl)thiophene

Conditions
ConditionsYield
Stage #1: C26H37FOS With hydrazine hydrate In dimethyl sulfoxide at 80℃;
Stage #2: With potassium hydroxide In dimethyl sulfoxide at 200℃; for 4h;
74.9%
thiophene boronic acid
6165-68-0

thiophene boronic acid

C10H12FS(1+)*F6P(1-)

C10H12FS(1+)*F6P(1-)

2-(4-fluorophenyl)thiophene
58861-48-6

2-(4-fluorophenyl)thiophene

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In ethanol at 40℃; for 3h;74%
thiophene
188290-36-0

thiophene

4-fluoroaniline
371-40-4

4-fluoroaniline

2-(4-fluorophenyl)thiophene
58861-48-6

2-(4-fluorophenyl)thiophene

Conditions
ConditionsYield
With tert.-butylnitrite In acetonitrile at 25℃; for 0.75h; Flow reactor; Irradiation;74%
Stage #1: 4-fluoroaniline With tetrafluoroboric acid; sodium nitrite In water at 0℃; for 1h; Green chemistry;
Stage #2: thiophene With 3,4,5-trihydroxybenzoic acid In water; acetone at 20℃; for 12h; Inert atmosphere; Green chemistry;
Stage #1: 4-fluoroaniline With tetrafluoroboric acid; sodium nitrite In water at 0℃; for 0.666667h;
Stage #2: thiophene In ethanol at 25℃; for 1h; Irradiation; Inert atmosphere;
80 %Chromat.
Stage #1: 4-fluoroaniline With tetrafluoroboric acid; sodium nitrite In water; acetone for 1h; Cooling;
Stage #2: thiophene With 1,2,3,4-tetrahydrocarbazole In dimethyl sulfoxide Inert atmosphere; Darkness; regioselective reaction;
(Z)-1-(4-bromobut-3-en-1-yn-1-yl)-4-fluorobenzene

(Z)-1-(4-bromobut-3-en-1-yn-1-yl)-4-fluorobenzene

2-(4-fluorophenyl)thiophene
58861-48-6

2-(4-fluorophenyl)thiophene

Conditions
ConditionsYield
With potassium ethyl xanthogenate; tetrabutyl phosphonium bromide In water at 130℃; for 20h; Schlenk technique; chemoselective reaction;73%
2-bromothiophene
1003-09-4

2-bromothiophene

4-flourophenylmagnesium bromide
352-13-6

4-flourophenylmagnesium bromide

A

2-(4-fluorophenyl)thiophene
58861-48-6

2-(4-fluorophenyl)thiophene

B

4,4'-difluorobiphenyl
398-23-2

4,4'-difluorobiphenyl

C

2,2'-Bithiophene
492-97-7

2,2'-Bithiophene

Conditions
ConditionsYield
Stage #1: 4-flourophenylmagnesium bromide With bismuth(III) chloride
Stage #2: 2-bromothiophene With potassium phosphate; palladium diacetate; triphenylphosphine In N,N-dimethyl-formamide at 90℃; for 1h; Inert atmosphere;
A 72%
B n/a
C n/a
5-(4-fluorophenyl)thiophene-2-carboxylic acid
115933-30-7

5-(4-fluorophenyl)thiophene-2-carboxylic acid

2-(4-fluorophenyl)thiophene
58861-48-6

2-(4-fluorophenyl)thiophene

Conditions
ConditionsYield
With copper In sulfolane at 200℃; for 2h;72%
phenyl 5-(4-fluorophenyl)thiophene-2-carboxylate

phenyl 5-(4-fluorophenyl)thiophene-2-carboxylate

2-(4-fluorophenyl)thiophene
58861-48-6

2-(4-fluorophenyl)thiophene

Conditions
ConditionsYield
With nickel(II) acetate tetrahydrate; 1,2-bis-(dicyclohexylphosphino)ethane In toluene at 170℃; for 24h; Inert atmosphere; Glovebox; Sealed tube;71%
With nickel(II) acetate tetrahydrate; 1,2-bis-(dicyclohexylphosphino)ethane In toluene at 170℃; for 24h;71%
2-bromothiophene
1003-09-4

2-bromothiophene

4-fluoro-1-iodobenzene
352-34-1

4-fluoro-1-iodobenzene

2-(4-fluorophenyl)thiophene
58861-48-6

2-(4-fluorophenyl)thiophene

Conditions
ConditionsYield
Stage #1: 2-bromothiophene With magnesium; ethylene dibromide In tetrahydrofuran at 20℃; for 0.75h; Kumada Cross-Coupling; Inert atmosphere;
Stage #2: 4-fluoro-1-iodobenzene With 1,2-bis(diphenylphosphino)ethane nickel(II) chloride In tetrahydrofuran at 20℃; Inert atmosphere; Reflux;
70%
4-[3-(4-fluorophenyl)-3-oxopropyl][1,3]dithietan-2-one
1509927-78-9

4-[3-(4-fluorophenyl)-3-oxopropyl][1,3]dithietan-2-one

2-(4-fluorophenyl)thiophene
58861-48-6

2-(4-fluorophenyl)thiophene

Conditions
ConditionsYield
With silica gel In neat (no solvent) at 215℃; Inert atmosphere;70%
thiophene
188290-36-0

thiophene

4-fluorobenzenediazonium tetrafluoroborate
459-45-0

4-fluorobenzenediazonium tetrafluoroborate

2-(4-fluorophenyl)thiophene
58861-48-6

2-(4-fluorophenyl)thiophene

Conditions
ConditionsYield
With cymantrene In dimethyl sulfoxide at 25℃; for 0.5h; Inert atmosphere; Irradiation; Flow reactor; regioselective reaction;59%
With epi-Cercosporin In dimethyl sulfoxide at 20℃; for 8h; Schlenk technique; Inert atmosphere; Irradiation; Green chemistry; regioselective reaction;57%
With graphitic carbon nitride/reduced graphene oxide nanocomposite In N,N-dimethyl-formamide at 20℃; for 1.5h; Inert atmosphere; UV-irradiation; Green chemistry;60 %Chromat.
thiophene
188290-36-0

thiophene

1-Bromo-4-fluorobenzene
460-00-4

1-Bromo-4-fluorobenzene

2-(4-fluorophenyl)thiophene
58861-48-6

2-(4-fluorophenyl)thiophene

Conditions
ConditionsYield
With palladium diacetate; potassium carbonate; catacxium A; Trimethylacetic acid In N,N-dimethyl-formamide at 110℃; for 12h; Schlenk technique; Inert atmosphere;58%
potassim 4-fluorophenyltrifluoroborate

potassim 4-fluorophenyltrifluoroborate

2-(n-butyltellanyl)thiophene
403617-22-1

2-(n-butyltellanyl)thiophene

2-(4-fluorophenyl)thiophene
58861-48-6

2-(4-fluorophenyl)thiophene

Conditions
ConditionsYield
With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; silver(l) oxide In methanol at 20℃; for 1.5h; Suzuki-Miyaura cross- coupling; Inert atmosphere;56%
thiophen-2-yl magnesium bromide
5713-61-1

thiophen-2-yl magnesium bromide

4-flourophenylmagnesium bromide
352-13-6

4-flourophenylmagnesium bromide

2-(4-fluorophenyl)thiophene
58861-48-6

2-(4-fluorophenyl)thiophene

Conditions
ConditionsYield
Stage #1: thiophen-2-yl magnesium bromide; 4-flourophenylmagnesium bromide With lithium chloride; manganese(ll) chloride In tetrahydrofuran at -10℃; Inert atmosphere;
Stage #2: With oxygen In tetrahydrofuran at 10 - 20℃;
51%
thiophene
188290-36-0

thiophene

triethyl(4-fluorophenyl)germane

triethyl(4-fluorophenyl)germane

2-(4-fluorophenyl)thiophene
58861-48-6

2-(4-fluorophenyl)thiophene

Conditions
ConditionsYield
With (triphenylphosphine)gold(I) chloride; [bis(acetoxy)iodo]benzene; camphor-10-sulfonic acid In 1,4-dioxane at 70℃; for 16h;48%
4-Fluorothiophenol
371-42-6

4-Fluorothiophenol

2-(4-fluorophenyl)thiophene
58861-48-6

2-(4-fluorophenyl)thiophene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 2.) NH4PF6 / 1.) MTBE, 23 deg C, 2.) acetone, 23 deg C
2: 74 percent / Pd(dppf)Cl2, K2CO3*H2O / aq. ethanol / 3 h / 40 °C
View Scheme
2-(4-fluorophenyl)thiophene
58861-48-6

2-(4-fluorophenyl)thiophene

C20H15NO

C20H15NO

C30H20FNOS

C30H20FNOS

Conditions
ConditionsYield
With 2-(1,3-dioxo-1H,3H-benzo[de]isoquinolin-2-yl)-3-methylbutyric acid; C30H33O2Rh; silver fluoride In N,N-dimethyl-formamide at 60℃; for 48h; Inert atmosphere; Schlenk technique; enantioselective reaction;99%
2-(4-fluorophenyl)thiophene
58861-48-6

2-(4-fluorophenyl)thiophene

1-(naphthalene-1-yl)benzo[h]isoquinoline

1-(naphthalene-1-yl)benzo[h]isoquinoline

C33H20FNS

C33H20FNS

Conditions
ConditionsYield
With 2-(1,3-dioxo-1H,3H-benzo[de]isoquinolin-2-yl)-3-methylbutyric acid; C30H33O2Rh; silver fluoride In N,N-dimethyl-formamide at 60℃; for 24h; Inert atmosphere; Schlenk technique; enantioselective reaction;98%
2-(4-fluorophenyl)thiophene
58861-48-6

2-(4-fluorophenyl)thiophene

C23H14FN

C23H14FN

C33H19F2NS

C33H19F2NS

Conditions
ConditionsYield
With 2-(1,3-dioxo-1H,3H-benzo[de]isoquinolin-2-yl)-3-methylbutyric acid; C30H33O2Rh; silver fluoride In N,N-dimethyl-formamide at 60℃; for 24h; Inert atmosphere; Schlenk technique; enantioselective reaction;97%
2-(4-fluorophenyl)thiophene
58861-48-6

2-(4-fluorophenyl)thiophene

2-bromo-5-(4-fluorophenyl)thiophene
1073313-97-9

2-bromo-5-(4-fluorophenyl)thiophene

Conditions
ConditionsYield
With N-Bromosuccinimide In dichloromethane95.3%
2-(4-fluorophenyl)thiophene
58861-48-6

2-(4-fluorophenyl)thiophene

5-bromo-2-methylbenzoic acid
79669-49-1

5-bromo-2-methylbenzoic acid

(5-bromo-2-methylphenyl)[5-(p-fluorophenyl)thiophene-2-yl]methanone
1132832-75-7

(5-bromo-2-methylphenyl)[5-(p-fluorophenyl)thiophene-2-yl]methanone

Conditions
ConditionsYield
Stage #1: 5-bromo-2-methylbenzoic acid With thionyl chloride In dichloromethane; N,N-dimethyl-formamide at 20 - 25℃;
Stage #2: 2-(4-fluorophenyl)thiophene With aluminum (III) chloride In dichloromethane at 0 - 25℃; for 12.5h; Solvent; Reagent/catalyst;
93.2%
Stage #1: 5-bromo-2-methylbenzoic acid With thionyl chloride In dichloromethane; N,N-dimethyl-formamide at 0 - 35℃;
Stage #2: 2-(4-fluorophenyl)thiophene With aluminum (III) chloride In dichloromethane; N,N-dimethyl-formamide at 0 - 35℃;
89%
Stage #1: 5-bromo-2-methylbenzoic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 25 - 30℃; for 0.1h; Inert atmosphere;
Stage #2: 2-(4-fluorophenyl)thiophene With aluminum (III) chloride In dichloromethane at 0 - 15℃; Inert atmosphere;
80.4%
Stage #1: 5-bromo-2-methylbenzoic acid With oxalyl dichloride In dichloromethane at 20℃; for 2h;
Stage #2: 2-(4-fluorophenyl)thiophene With aluminum (III) chloride In dichloromethane at -15 - 35℃; for 4h;
80%
2-(4-fluorophenyl)thiophene
58861-48-6

2-(4-fluorophenyl)thiophene

C8H7ClO2

C8H7ClO2

(2-methylphenyl)(5-(4-fluorophenyl)thiophen-2-yl)methanone

(2-methylphenyl)(5-(4-fluorophenyl)thiophen-2-yl)methanone

Conditions
ConditionsYield
With aluminum (III) chloride In dichloromethane at -20 - 20℃; for 3h; Inert atmosphere;92%
2-(4-fluorophenyl)thiophene
58861-48-6

2-(4-fluorophenyl)thiophene

C24H17N

C24H17N

C34H22FNS

C34H22FNS

Conditions
ConditionsYield
With 2-(1,3-dioxo-1H,3H-benzo[de]isoquinolin-2-yl)-3-methylbutyric acid; C30H33O2Rh; silver fluoride In N,N-dimethyl-formamide at 60℃; for 24h; Inert atmosphere; Schlenk technique; enantioselective reaction;92%
2-(4-fluorophenyl)thiophene
58861-48-6

2-(4-fluorophenyl)thiophene

5-bromo-2-methylbenzoyl chloride
21900-41-4

5-bromo-2-methylbenzoyl chloride

(5-bromo-2-methylphenyl)[5-(p-fluorophenyl)thiophene-2-yl]methanone
1132832-75-7

(5-bromo-2-methylphenyl)[5-(p-fluorophenyl)thiophene-2-yl]methanone

Conditions
ConditionsYield
With aluminum (III) chloride In dichloromethane at -10 - 25℃; for 5.5h; Friedel-Crafts Acylation; Inert atmosphere;90.1%
With aluminum (III) chloride In dichloromethane at 0 - 20℃; Friedel Crafts acylation;85.7%
Stage #1: 2-(4-fluorophenyl)thiophene; 5-bromo-2-methylbenzoyl chloride With aluminum (III) chloride In dichloromethane at -10 - 20℃; for 2.5 - 3.5h;
Stage #2: With hydrogenchloride; water In n-heptane; dichloromethane at -12℃;
Stage #1: 2-(4-fluorophenyl)thiophene; 5-bromo-2-methylbenzoyl chloride With aluminum (III) chloride In dichloromethane at 0 - 20℃;
Stage #2: With water In tetrahydrofuran cooling with ice;
2-(4-fluorophenyl)thiophene
58861-48-6

2-(4-fluorophenyl)thiophene

carbon dioxide
124-38-9

carbon dioxide

5-(4-fluorophenyl)thiophene-2-carboxylic acid
115933-30-7

5-(4-fluorophenyl)thiophene-2-carboxylic acid

Conditions
ConditionsYield
With ethylaluminum dichloride In hexane; toluene at 100℃; under 22502.3 Torr; for 3h; Autoclave; Inert atmosphere; regioselective reaction;90%
2-(4-fluorophenyl)thiophene
58861-48-6

2-(4-fluorophenyl)thiophene

C8H6BrClO2

C8H6BrClO2

C18H12BrFOS

C18H12BrFOS

Conditions
ConditionsYield
With aluminum (III) chloride In dichloromethane at -20 - 20℃; for 3h; Inert atmosphere;90%
2-(4-fluorophenyl)thiophene
58861-48-6

2-(4-fluorophenyl)thiophene

C24H17NO

C24H17NO

C34H22FNOS

C34H22FNOS

Conditions
ConditionsYield
With 2-(1,3-dioxo-1H,3H-benzo[de]isoquinolin-2-yl)-3-methylbutyric acid; C30H33O2Rh; silver fluoride In N,N-dimethyl-formamide at 60℃; for 24h; Inert atmosphere; Schlenk technique; enantioselective reaction;90%
2-(4-fluorophenyl)thiophene
58861-48-6

2-(4-fluorophenyl)thiophene

C25H17N

C25H17N

C35H22FNS

C35H22FNS

Conditions
ConditionsYield
With 2-(1,3-dioxo-1H,3H-benzo[de]isoquinolin-2-yl)-3-methylbutyric acid; C30H33O2Rh; silver fluoride In N,N-dimethyl-formamide at 60℃; for 24h; Inert atmosphere; Schlenk technique; enantioselective reaction;90%
2-(4-fluorophenyl)thiophene
58861-48-6

2-(4-fluorophenyl)thiophene

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

5-(4-fluorophenyl)thiophene-2-carboxaldehyde
249504-38-9

5-(4-fluorophenyl)thiophene-2-carboxaldehyde

Conditions
ConditionsYield
Stage #1: 2-(4-fluorophenyl)thiophene; N,N-dimethyl-formamide With tris(trimethylsilyl)amine; tetramethylammonium fluoride at 20℃; for 24h; Inert atmosphere; Sealed tube;
Stage #2: With hydrogenchloride In water at 20℃; for 1.5h;
86%
2-(4-fluorophenyl)thiophene
58861-48-6

2-(4-fluorophenyl)thiophene

1-(pyren-1-yl)benzo[h]isoquinoline

1-(pyren-1-yl)benzo[h]isoquinoline

C39H22FNS

C39H22FNS

Conditions
ConditionsYield
With 2-(1,3-dioxo-1H,3H-benzo[de]isoquinolin-2-yl)-3-methylbutyric acid; C30H33O2Rh; silver fluoride In N,N-dimethyl-formamide at 60℃; for 24h; Inert atmosphere; Schlenk technique; enantioselective reaction;86%
2-(4-fluorophenyl)thiophene
58861-48-6

2-(4-fluorophenyl)thiophene

2,2,2-trifluoro-1-(1H-indol-3-yl)-1-(thiophen-2-yl)ethan-1-ol
1150561-00-4

2,2,2-trifluoro-1-(1H-indol-3-yl)-1-(thiophen-2-yl)ethan-1-ol

3-(2,2,2-trifluoro-1-(5-(4-fluorophenyl)thiophen-2-yl)-1-(thiophen-2-yl)ethyl)-1H-indole

3-(2,2,2-trifluoro-1-(5-(4-fluorophenyl)thiophen-2-yl)-1-(thiophen-2-yl)ethyl)-1H-indole

Conditions
ConditionsYield
With dodecylbenzenesulfonic acid In water at 80℃; for 24h; Green chemistry;83%
2-(4-fluorophenyl)thiophene
58861-48-6

2-(4-fluorophenyl)thiophene

5-iodo-2-methylbenzoic acid
54811-38-0

5-iodo-2-methylbenzoic acid

(5-(4-fluorophenyl)thiophen-2-yl)(5-iodo-2-methylphenyl)methanone

(5-(4-fluorophenyl)thiophen-2-yl)(5-iodo-2-methylphenyl)methanone

Conditions
ConditionsYield
Stage #1: 5-iodo-2-methylbenzoic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 2h;
Stage #2: 2-(4-fluorophenyl)thiophene With aluminum (III) chloride In dichloromethane at -15 - 35℃; for 4h;
81%
Stage #1: 5-iodo-2-methylbenzoic acid With thionyl chloride In dichloromethane; N,N-dimethyl-formamide for 1h; Reflux;
Stage #2: 2-(4-fluorophenyl)thiophene With aluminum (III) chloride In dichloromethane; N,N-dimethyl-formamide at 0 - 30℃; for 1h;
222 g
2-(4-fluorophenyl)thiophene
58861-48-6

2-(4-fluorophenyl)thiophene

5-iodo-2-methylbenzoyl chloride
108440-70-6

5-iodo-2-methylbenzoyl chloride

(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)
898566-17-1

(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)

Conditions
ConditionsYield
With aluminum (III) chloride Solvent; Temperature; Friedel-Crafts Acylation;80%
Stage #1: 5-iodo-2-methylbenzoyl chloride With aluminum (III) chloride In dichloromethane at 2℃; for 0.25h;
Stage #2: 2-(4-fluorophenyl)thiophene In dichloromethane at 2 - 20℃; for 2.41667h; Product distribution / selectivity;
2-(4-fluorophenyl)thiophene
58861-48-6

2-(4-fluorophenyl)thiophene

phenylboronic acid
98-80-6

phenylboronic acid

2-(4-fluorophenyl)-4-phenylthiophene
1415605-87-6

2-(4-fluorophenyl)-4-phenylthiophene

Conditions
ConditionsYield
With palladium(II) trifluoroacetate; cesium trifluoroacetate; p-benzoquinone; silver(l) oxide In acetic acid; trifluoroacetic acid at 20℃; for 15h; regioselective reaction;80%

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