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Cas Database |
| Name |
2-Thiophenecarbonyl chloride |
EINECS | 226-092-4 |
| CAS No. | 5271-67-0 | Density | 1.391 g/cm3 |
| PSA | 45.31000 | LogP | 2.12710 |
| Solubility | N/A | Melting Point |
N/A |
| Formula | C5H3ClOS | Boiling Point | 201.8 °C at 760 mmHg |
| Molecular Weight | 146.597 | Flash Point | 75.9 °C |
| Transport Information | UN 3265 8/PG 2 | Appearance | clear colourless to yellow-grey liquid |
| Safety | 26-36/37/39-45 | Risk Codes | 34-37 |
| Molecular Structure |
|
Hazard Symbols |
 C, Xi
|
| Synonyms |
2-(Chlorocarbonyl)thiophene;2-(Chloroformyl)thiophene;2-Thenoyl chloride;2-Thienylcarbonyl chloride;2-Thiophenecarboxylic acid chloride;2-Thiophenecarboxylic chloride;Thenoyl chloride;Thiophen-2-ylcarbonyl chloride;a-Thenoyl chloride; |
Article Data | 26 |
2-Thiophenecarbonyl chloride Synthetic route
| 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% |
- 30717-57-8
N, N-dimethylthiophene-2-carboxamide
- 5271-67-0
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% |
- 3437-95-4
2-Iodothiophene
- 122-04-3
4-nitro-benzoyl chloride
A
- 636-98-6
p-nitrobenzene iodide
B
- 5271-67-0
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 |
- 39880-77-8
N‐methyl‐2‐thiophenecarboxamide
A
- 5271-67-0
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 |
- 156330-47-1
methyl N-methylthiophene-2-carboximidate
A
- 5271-67-0
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 |
2-Thiophenecarbonyl chloride Specification
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.
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The yield is 97 %.
6. Use of 2-Thiophenecarbonylchloride
2-Thiophenecarbonylchloride can react with diazomethane to get 2-diazo-1-thiophen-2-yl-ethanone.
.jpg)
The yield is 60 %.
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