Conditions | Yield |
---|---|
97% | |
With thionyl chloride for 2h; Heating; | 82% |
With thionyl chloride; N,N-dimethyl-formamide; sodium hydroxide In ethyl acetate at 58 - 65℃; for 2.5h; Inert atmosphere; | 81% |
Conditions | Yield |
---|---|
With sulfolane at 200℃; under 60006 Torr; for 0.75h; Temperature; Pressure; Reagent/catalyst; | 93% |
N, N-dimethylthiophene-2-carboxamide
2-Thiophenecarbonyl chloride
Conditions | Yield |
---|---|
With iodine; N,N-dimethyl-formamide; phosphorus trichloride In 1,2-dichloro-ethane at 100℃; for 12h; Schlenk technique; Sealed tube; | 92% |
Conditions | Yield |
---|---|
Stage #1: 2-Acetylthiophene With pyridine; disulfur dichloride In chlorobenzene at 20℃; for 1.75h; Stage #2: With sulfuryl dichloride In chlorobenzene at 20 - 132℃; for 14.5h; Temperature; Time; Reagent/catalyst; | 90% |
Stage #1: 2-Acetylthiophene With pyridine; sulfur monochloride at 20℃; for 0.166667h; Stage #2: at 70℃; for 3h; Stage #3: at 137℃; for 18h; | 86% |
With α-picoline; thionyl chloride at 70 - 140℃; for 17.75h; Temperature; Reagent/catalyst; | 72% |
With pyridine; disulfur dichloride at 70 - 137℃; for 21.5h; Concentration; Temperature; | 86 %Spectr. |
Multi-step reaction with 2 steps 1: propionic acid; cobalt(II) nitrate hexahydrate; manganese (II) nitrate tetrahydrate; oxygen / 125 °C / 760.05 Torr 2: N,N-dimethyl-formamide; thionyl chloride; sodium hydroxide / ethyl acetate / 2.5 h / 58 - 65 °C / Inert atmosphere View Scheme |
Conditions | Yield |
---|---|
With bis(tri-t-butylphosphine)palladium(0); benzyltriphenylphosphonium chloride In toluene at 110℃; under 38002.6 Torr; for 48h; Glovebox; Autoclave; Inert atmosphere; | 78% |
2-Iodothiophene
4-nitro-benzoyl chloride
A
p-nitrobenzene iodide
B
2-Thiophenecarbonyl chloride
Conditions | Yield |
---|---|
With (Xantphos)Pd(4-C6H4NO2)(I) In benzene at 90℃; for 20h; Sealed tube; Inert atmosphere; | A n/a B 52% |
Conditions | Yield |
---|---|
With iodine; phosphorus trichloride at 160℃; for 48h; Schlenk technique; Sealed tube; | 26% |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 97 percent / 10 percent aq. HCl / dioxane / 1 h / Heating 2: SOCl2 / 5 h / Heating View Scheme |
N‐methyl‐2‐thiophenecarboxamide
A
2-Thiophenecarbonyl chloride
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 96 percent / SOCl2 / 18 h / Heating 2: 97 percent / methanol; tetrahydrofuran / 1.) 0 deg C, 0.5 h, 2.) room temperature, 12 h 3: 76 percent / 10 percent aq. HCl / 0.5 h / Ambient temperature 4: 97 percent / 10 percent aq. HCl / dioxane / 1 h / Heating 5: SOCl2 / 5 h / Heating View Scheme |
methyl N-methylthiophene-2-carboximidate
A
2-Thiophenecarbonyl chloride
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 76 percent / 10 percent aq. HCl / 0.5 h / Ambient temperature 2: 97 percent / 10 percent aq. HCl / dioxane / 1 h / Heating 3: SOCl2 / 5 h / Heating View Scheme |
N-methylthiophene-2-carboximidoyl chloride
A
2-Thiophenecarbonyl chloride
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 97 percent / methanol; tetrahydrofuran / 1.) 0 deg C, 0.5 h, 2.) room temperature, 12 h 2: 76 percent / 10 percent aq. HCl / 0.5 h / Ambient temperature 3: 97 percent / 10 percent aq. HCl / dioxane / 1 h / Heating 4: SOCl2 / 5 h / Heating View Scheme |
potassium thiophene-2-carboxylate
2-Thiophenecarbonyl chloride
Conditions | Yield |
---|---|
With oxalyl dichloride In dichloromethane for 3.5h; Cooling with ice; Reflux; |
2-thiophenylcarboxylic acid
oxalyl dichloride
2-Thiophenecarbonyl chloride
Conditions | Yield |
---|---|
In dichloromethane; N,N-dimethyl-formamide at 20℃; for 2h; |
2-Iodothiophene
terephthaloyl chloride
A
2-Thiophenecarbonyl chloride
B
4-iodobenzoic acid chloride
Conditions | Yield |
---|---|
With (Xantphos)Pd(4-C6H4NO2)(I) In benzene at 110℃; for 20h; Sealed tube; Inert atmosphere; | A 92 %Spectr. B n/a |
N-chlorosulfonyl-thiophene-2-carboxamide
2-Thiophenecarbonyl chloride
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: hydrogenchloride / dibutyl ether; water / 20 °C 2: hydrogenchloride / dibutyl ether / 7 h / 100 °C 3: N,N-dimethyl-formamide; thionyl chloride / 1.5 h / 65 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: hydrogenchloride / dibutyl ether / 7 h / 100 °C 2: N,N-dimethyl-formamide; thionyl chloride / 1.5 h / 65 °C View Scheme |
Conditions | Yield |
---|---|
With N-chloro-succinimide; thio-xanthene-9-one In acetonitrile at 20℃; for 7h; Irradiation; |
2-Thiophenecarbonyl chloride
α-naphthol
1-naphthyl thiophen-2-carboxylate
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at 20℃; for 14h; | 100% |
Stage #1: 2-Thiophenecarbonyl chloride; α-naphthol In tetrahydrofuran at 0 - 20℃; Stage #2: With triethylamine In tetrahydrofuran for 4h; | 99% |
Stage #1: 2-Thiophenecarbonyl chloride; α-naphthol With triethylamine In tetrahydrofuran at 0℃; for 4h; Stage #2: With hydrogenchloride In tetrahydrofuran | 99% |
With sodium hydroxide |
2-Thiophenecarbonyl chloride
2-methoxy-phenylamine
N-(2-methoxyphenyl)-2-thiophenecarboxamide
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; | 100% |
In toluene |
2-Thiophenecarbonyl chloride
phenethylamine
N-(2-phenylethyl)thiophene-2-carboxamide
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 23℃; | 100% |
In dichloromethane for 4h; Ambient temperature; | 87% |
In dichloromethane at 20 - 70℃; for 5h; Alkaline conditions; | 71% |
With morpholinomethyl polystyrene HL In dichloromethane at 20℃; |
Conditions | Yield |
---|---|
With sodium azide In water; acetone at 0℃; for 3.5h; | 100% |
With sodium azide In water; acetone for 0.333333h; | |
With sodium azide |
Conditions | Yield |
---|---|
With bis(iodozinc)methane at 25℃; Substitution; | 100% |
2-Thiophenecarbonyl chloride
4-[3-aminobenzoyl]-1-methylpiperidine
4-[3-(thien-2-ylamidyl)benzoyl]-1-methylpiperidine
Conditions | Yield |
---|---|
With (piperidinomethyl)-polystyrene In tetrahydrofuran for 18h; | 100% |
2-Thiophenecarbonyl chloride
2-amino-4-chloro-6-(2-methoxyphenyl)pyridin trifluoroacetate
N-[4-chloro-6-(2-methoxyphenyl)pyridin-2-yl]thiophene-2-carboxamide
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; for 16h; | 100% |
2-Thiophenecarbonyl chloride
phosphorous acid trimethyl ester
dimethyl thiophene-2-carbonylphosphonate
Conditions | Yield |
---|---|
at 20℃; for 1h; | 100% |
2-Thiophenecarbonyl chloride
C17H18N2O5S
Conditions | Yield |
---|---|
With pyridine In dichloromethane at -10℃; | 100% |
2-Thiophenecarbonyl chloride
ethyl 2-((4-methoxyphenyl)imino)-4-(triethylsilyl)but-3-ynoate
ethylmagnesium bromide
ethyl 2-(ethyl(4-methoxyphenyl)amino)-2-(thiophen-2-carbonyl)-4-(triethylsilyl)but-3-ynoate
Conditions | Yield |
---|---|
Stage #1: ethyl 2-((4-methoxyphenyl)imino)-4-(triethylsilyl)but-3-ynoate; ethylmagnesium bromide In tetrahydrofuran at -78℃; Inert atmosphere; Stage #2: 2-Thiophenecarbonyl chloride In tetrahydrofuran at -78 - 20℃; for 0.5h; Inert atmosphere; regioselective reaction; | 100% |
2-Thiophenecarbonyl chloride
benzyl 2,2-dimethyl-3-hydroxypropanoic acid
3-(benzyloxy)-2,2-dimethyl-3-oxopropyl thiophene-2-carboxylate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane for 2h; Cooling with ice; | 100% |
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane at 20℃; for 4h; | 100% |
2-Thiophenecarbonyl chloride
Conditions | Yield |
---|---|
With sodium hydroxide In tetrahydrofuran; water for 0.166667h; Cooling with ice; | 100% |
2-Thiophenecarbonyl chloride
N-aminopyridin-1-ium iodide
(pyridin-1-ium-1-yl)(thiophene-2-carbonyl)amide
Conditions | Yield |
---|---|
With sodium hydroxide for 24h; Ambient temperature; | 99.5% |
With potassium carbonate In methanol at 20℃; for 72h; | 98% |
2-Thiophenecarbonyl chloride
anthranilic acid
2-Thiophen-2-yl-4H-3,1-benzoxazin-4-one
Conditions | Yield |
---|---|
With acetic anhydride; triethylamine In ethyl acetate | 99% |
Stage #1: 2-Thiophenecarbonyl chloride; anthranilic acid In N,N-dimethyl acetamide at 7 - 13℃; for 4h; Cooling with ice; Stage #2: With acetic anhydride In N,N-dimethyl acetamide at 98 - 118℃; for 2h; | 95% |
With pyridine at 0 - 20℃; for 0.583333h; | 37% |
2-Thiophenecarbonyl chloride
2-methylmethoxybenzene
(4-methoxy-3-methylphenyl)(2-thienyl)methanone
Conditions | Yield |
---|---|
With aluminium trichloride In dichloromethane for 0.75h; < 12 deg C; | 99% |
2-Thiophenecarbonyl chloride
2-Chloroaniline
N-(2-chlorophenyl)thiophene-2-carboxamide
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; for 24h; | 99% |
In toluene |
2-Thiophenecarbonyl chloride
2-bromoaniline
thiophene-2-carboxylic acid (2-bromophenyl)amide
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; for 24h; | 99% |
In tetrahydrofuran at 20℃; for 24h; | 96% |
With triethylamine In dichloromethane at 0 - 20℃; | 84% |
In toluene | |
With triethylamine In dichloromethane at 20℃; for 3h; |
2-Thiophenecarbonyl chloride
thiophen-2-carboxylic anhydride
Conditions | Yield |
---|---|
With N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate In toluene for 3h; Heating; | 99% |
With zinc In N,N-dimethyl-formamide; pentane at 20℃; for 20h; Inert atmosphere; Schlenk technique; | 33% |
With water; triethylamine In acetone at 20℃; for 12h; Schlenk technique; Inert atmosphere; Sealed tube; |
Conditions | Yield |
---|---|
Stage #1: 3,3-Dimethylbut-1-yne With polymethylhydrosiloxane; trifuran-2-yl-phosphane; trimethyltin fluoride; tris-(dibenzylideneacetone)dipalladium(0); tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 2h; Stage #2: 2-Thiophenecarbonyl chloride In tetrahydrofuran at 65℃; for 2h; Stille reaction; | 99% |
2-Thiophenecarbonyl chloride
4-Isopropyl-5-methyl-2-phenyl-2,4-dihydro-pyrazol-3-one
Conditions | Yield |
---|---|
With triethylamine In chloroform for 1h; Heating; | 99% |
2-Thiophenecarbonyl chloride
N-(tert-butyl)thiophene-2-carboxamide
Conditions | Yield |
---|---|
99% |
2-Thiophenecarbonyl chloride
benzyl alcohol
benzyl thiophen-2-ylcarbamate
Conditions | Yield |
---|---|
Stage #1: 2-Thiophenecarbonyl chloride With pyridine; trimethylsilylazide In N,N-dimethyl-formamide at 20℃; Curtius rearrangement; Microflow reaction; Inert atmosphere; Stage #2: benzyl alcohol With acetic acid In N,N-dimethyl-formamide at 110℃; Microflow reaction; Inert atmosphere; | 99% |
2-Thiophenecarbonyl chloride
10-Undecen-1-ol
2-thiophenecarboxylic acid, undec-10-enyl ester
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 1h; Inert atmosphere; | 99% |
2-Thiophenecarbonyl chloride
1-hydrazino-4-(4-methoxyphenyl)-5H-2,3-benzodiazepine
Conditions | Yield |
---|---|
In 1,4-dioxane for 1h; Reflux; | 99% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; for 1h; Inert atmosphere; | 99% |
2-Thiophenecarbonyl chloride
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at 0 - 20℃; for 1h; Inert atmosphere; | 99% |
2-Thiophenecarbonyl chloride
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; for 1h; | 99% |
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane at 0℃; for 2h; Inert atmosphere; | 99% |
With dmap; triethylamine In dichloromethane at 20℃; | 90% |
With dmap; triethylamine In dichloromethane at 0 - 20℃; | 83% |
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 21 - 23℃; for 24h; Inert atmosphere; | 99% |
1. Introduction of 2-Thiophenecarbonylchloride
2-Thiophenecarbonyl chloride with the CAS registry number of 5271-67-0, is also named as 2-Thenoyl chloride. The systematic name of 2-Thiophenecarbonylchloride is thiophene-2-carbonyl chloride. The product's categories are Acidhalide; Thiophene & Benzothiophene; Heterocyclic Compounds. Besides, it is clear colourless to yellow-grey liquid, which should be sealed in a dark, cool, dry place at 2-8 °C. In addition, its molecular formula is C5H3ClOS and molecular weight is 146.59.
2. Properties of 2-Thiophenecarbonylchloride
The other characteristics of 2-Thiophenecarbonyl chloride can be summarized as: (1)EINECS: 226-092-4; (2)ACD/LogP: 1.89; (3)# of Rule of 5 Violations: 0; (4)ACD/LogD (pH 5.5): 1.89; (5)ACD/LogD (pH 7.4): 1.89; (6)ACD/BCF (pH 5.5): 16.01; (7)ACD/BCF (pH 7.4): 16.01; (8)ACD/KOC (pH 5.5): 253.39; (9)ACD/KOC (pH 7.4): 253.39; (10)#H bond acceptors: 1; (11)#H bond donors: 0; (12)#Freely Rotating Bonds: 1; (13)Polar Surface Area: 45.31 Å2; (14)Index of Refraction: 1.576; (15)Molar Refractivity: 34.88 cm3; (16)Molar Volume: 105.3 cm3; (17)Polarizability: 13.82×10-24cm3; (18)Surface Tension: 45.9 dyne/cm; (19)Density: 1.391 g/cm3; (20)Flash Point: 75.9 °C; (21)Enthalpy of Vaporization: 43.81 kJ/mol; (22)Boiling Point: 201.8 °C at 760 mmHg; (23)Vapour Pressure: 0.302 mmHg at 25 °C.
3. Structure Descriptors of 2-Thiophenecarbonylchloride
(1)SMILES: ClC(=O)c1sccc1
(2)InChI: InChI=1/C5H3ClOS/c6-5(7)4-2-1-3-8-4/h1-3H
(3)InChIKey: QIQITDHWZYEEPA-UHFFFAOYAG
(4)Std. InChI: InChI=1S/C5H3ClOS/c6-5(7)4-2-1-3-8-4/h1-3H
(5)Std. InChIKey: QIQITDHWZYEEPA-UHFFFAOYSA-N
4. Safety Information of 2-Thiophenecarbonylchloride
When you are using this chemical, please be cautious about it as the following: it is toxic to aquatic organisms. It also irritates to respiratory system. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. And you should wear suitable protective clothing, gloves and eye/face protection. Moreover, in case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
5. Preparation of 2-Thiophenecarbonylchloride
2-Thiophenecarbonylchloride can be prepared by thiophene-2-carboxylic acid.
The yield is 97 %.
6. Use of 2-Thiophenecarbonylchloride
2-Thiophenecarbonylchloride can react with diazomethane to get 2-diazo-1-thiophen-2-yl-ethanone.
The yield is 60 %.
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