Conditions | Yield |
---|---|
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
4-flourophenylmagnesium bromide
2-(4-fluorophenyl)thiophene
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
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
1-Bromo-4-fluorobenzene
2-(4-fluorophenyl)thiophene
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
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
2-(4-fluorophenyl)thiophene
Conditions | Yield |
---|---|
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
2-(4-fluorophenyl)thiophene
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); silver tetrafluoroborate In N,N-dimethyl-formamide at 80℃; for 16h; chemoselective reaction; | 88% |
2-bromothiophene
2-(4-fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
2-(4-fluorophenyl)thiophene
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In Dimethyl ether; water at 70 - 75℃; | 87% |
thiophene boronic acid
4-fluoro-1-iodobenzene
2-(4-fluorophenyl)thiophene
Conditions | Yield |
---|---|
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
2-(4-fluorophenyl)thiophene
Conditions | Yield |
---|---|
With tetraphosphorus decasulfide In toluene for 0.5h; Microwave irradiation; | 85% |
5-(4-fluorophenyl)thiophene-2-carboxaldehyde
2-(4-fluorophenyl)thiophene
Conditions | Yield |
---|---|
With Pd-γ-Fe2O3 In cyclohexane at 130℃; for 24h; Inert atmosphere; Molecular sieve; Sealed tube; | 83% |
2-(4-fluorophenyl)thiophene
Conditions | Yield |
---|---|
With potassium sulfide; iodine In N,N-dimethyl-formamide at 110℃; for 11.8h; Inert atmosphere; chemoselective reaction; | 76% |
2-(4-fluorophenyl)thiophene
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In ethanol at 40℃; for 3h; | 74% |
Conditions | Yield |
---|---|
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; |
2-(4-fluorophenyl)thiophene
Conditions | Yield |
---|---|
With potassium ethyl xanthogenate; tetrabutyl phosphonium bromide In water at 130℃; for 20h; Schlenk technique; chemoselective reaction; | 73% |
2-bromothiophene
4-flourophenylmagnesium bromide
A
2-(4-fluorophenyl)thiophene
B
4,4'-difluorobiphenyl
C
2,2'-Bithiophene
Conditions | Yield |
---|---|
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
2-(4-fluorophenyl)thiophene
Conditions | Yield |
---|---|
With copper In sulfolane at 200℃; for 2h; | 72% |
2-(4-fluorophenyl)thiophene
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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
2-(4-fluorophenyl)thiophene
Conditions | Yield |
---|---|
With silica gel In neat (no solvent) at 215℃; Inert atmosphere; | 70% |
thiophene
4-fluorobenzenediazonium tetrafluoroborate
2-(4-fluorophenyl)thiophene
Conditions | Yield |
---|---|
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. |
Conditions | Yield |
---|---|
With palladium diacetate; potassium carbonate; catacxium A; Trimethylacetic acid In N,N-dimethyl-formamide at 110℃; for 12h; Schlenk technique; Inert atmosphere; | 58% |
2-(n-butyltellanyl)thiophene
2-(4-fluorophenyl)thiophene
Conditions | Yield |
---|---|
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
4-flourophenylmagnesium bromide
2-(4-fluorophenyl)thiophene
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With (triphenylphosphine)gold(I) chloride; [bis(acetoxy)iodo]benzene; camphor-10-sulfonic acid In 1,4-dioxane at 70℃; for 16h; | 48% |
4-Fluorothiophenol
2-(4-fluorophenyl)thiophene
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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
2-bromo-5-(4-fluorophenyl)thiophene
Conditions | Yield |
---|---|
With N-Bromosuccinimide In dichloromethane | 95.3% |
2-(4-fluorophenyl)thiophene
5-bromo-2-methylbenzoic acid
(5-bromo-2-methylphenyl)[5-(p-fluorophenyl)thiophene-2-yl]methanone
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
With aluminum (III) chloride In dichloromethane at -20 - 20℃; for 3h; Inert atmosphere; | 92% |
Conditions | Yield |
---|---|
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
5-bromo-2-methylbenzoyl chloride
(5-bromo-2-methylphenyl)[5-(p-fluorophenyl)thiophene-2-yl]methanone
Conditions | Yield |
---|---|
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
carbon dioxide
5-(4-fluorophenyl)thiophene-2-carboxylic acid
Conditions | Yield |
---|---|
With ethylaluminum dichloride In hexane; toluene at 100℃; under 22502.3 Torr; for 3h; Autoclave; Inert atmosphere; regioselective reaction; | 90% |
Conditions | Yield |
---|---|
With aluminum (III) chloride In dichloromethane at -20 - 20℃; for 3h; Inert atmosphere; | 90% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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
N,N-dimethyl-formamide
5-(4-fluorophenyl)thiophene-2-carboxaldehyde
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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
2,2,2-trifluoro-1-(1H-indol-3-yl)-1-(thiophen-2-yl)ethan-1-ol
Conditions | Yield |
---|---|
With dodecylbenzenesulfonic acid In water at 80℃; for 24h; Green chemistry; | 83% |
2-(4-fluorophenyl)thiophene
5-iodo-2-methylbenzoic acid
Conditions | Yield |
---|---|
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
5-iodo-2-methylbenzoyl chloride
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)
Conditions | Yield |
---|---|
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
phenylboronic acid
2-(4-fluorophenyl)-4-phenylthiophene
Conditions | Yield |
---|---|
With palladium(II) trifluoroacetate; cesium trifluoroacetate; p-benzoquinone; silver(l) oxide In acetic acid; trifluoroacetic acid at 20℃; for 15h; regioselective reaction; | 80% |
The 2-(4-Fluorophenyl)thiophene with the CAS number 58861-48-6 is also called Thiophene,2-(4-fluorophenyl)-. Its molecular formula is C10H7FS. This chemical is a kind of organics. It should be stored in dry and cool environment.
The properties of the 2-(4-Fluorophenyl)thiophene are: (1)ACD/LogP: 3.83; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 4; (4)ACD/LogD (pH 7.4): 4; (5)ACD/BCF (pH 5.5): 391; (6)ACD/BCF (pH 7.4): 391; (7)ACD/KOC (pH 5.5): 2497; (8)ACD/KOC (pH 7.4): 2497; (9)#H bond acceptors: 0; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 28.24 Å2; (13)Index of Refraction: 1.578; (14)Molar Refractivity: 49.223 cm3; (15)Molar Volume: 148.407 cm3; (16)Polarizability: 19.513×10-24cm3; (17)Surface Tension: 39.02 dyne/cm; (18)Enthalpy of Vaporization: 46.986 kJ/mol; (19)Vapour Pressure: 0.031 mmHg at 25°C.
You can still convert the following datas into molecular structure:
(1)SMILES: Fc1ccc(cc1)c2cccs2
(2)InChI: InChI=1/C10H7FS/c11-9-5-3-8(4-6-9)10-2-1-7-12-10/h1-7H
(3)InChIKey: PURJRGMZIKXDMW-UHFFFAOYAA
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