3-undecylthieno[3,2-b]thiophene CAS#: 950223-97-9; ChemWhat Code: 1372851
Identification
| Product Name | 3-undecylthieno[3,2-b]thiophene |
| IUPAC Name | 6-undecylthieno[3,2-b]thiophene |
| Molecular Structure | ![Structure of 3-undecylthieno[3,2-b]thiophene CAS 950223-97-9](https://www.chemwhat.com/wp-content/uploads/2020/04/Structure-of-3-undecylthieno32-bthiophene-CAS-950223-97-9.png) |
| CAS Registry Number | 950223-97-9 |
| EINECS Number | No data available |
| MDL Number | No data available |
| Beilstein Registry Number | No data available |
| Synonyms | 3-Undecylthieno[3,2-b]thiophen 3-Undecylthieno[3,2-b]thiophene 3-Undécylthiéno[3,2-b]thiophène Thieno[3,2-b]thiophene, 3-undecyl- 950223-97-9 |
| Molecular Formula | C17H26S2 |
| Molecular Weight | 294.518 |
| InChI | InChI=1S/C17H26S2/c1-2-3-4-5-6-7-8-9-10-11-15-14-19-16-12-13-18-17(15)16/h12-14H,2-11H2,1H3 |
| InChI Key | BVCVLQZKDYRAHL-UHFFFAOYSA-N |
| Canonical SMILES | CCCCCCCCCCCc1csc2c1scc2 |
| Patent Information |
| No data available |
Physical Data
| Appearance | Colorless liquid |
| Solubility | No data available |
| Flash Point | No data available |
| Refractive index | No data available |
| Sensitivity | No data available |
| Density, g·cm-3 |
| 1.097 |
| 0.977 |
Spectra
| Description (NMR Spectroscopy) | Nucleus (NMR Spectroscopy) | Solvents (NMR Spectroscopy) | Frequency (NMR Spectroscopy), MHz |
| Chemical shifts | 1H | chloroform-d1 | 400 |
| Chemical shifts | 1H | chloroform-d1 | 100 |
![HNMR of 3-undecylthieno[3,2-b]thiophene CAS 950223-97-9](https://www.chemwhat.com/wp-content/uploads/2020/04/HNMR-of-3-undecylthieno32-bthiophene-CAS-950223-97-9-.png)
| Description (Mass Spectroscopy) | Solvent (IR Spectroscopy) | Temperature (IR Spectroscopy), °C |
| Spectrum |
Route of Synthesis (ROS)
![Route of Synthesis (ROS) of 3-undecylthieno[3,2-b]thiophene CAS# 950223-97-9](https://www.chemwhat.com/wp-content/uploads/2020/04/Route-of-Synthesis-ROS-of-3-undecylthieno32-bthiophene-CAS-950223-97-9.png)
| Conditions | Yield |
| Stage #1: 3-undecylthieno[3,2-b]thiophene With n-butyllithium In tetrahydrofuran at 0℃; for 1.5h; Inert atmosphere; Stage #2: With trimethyltin(IV)chloride In tetrahydrofuran at 0 – 20℃; for 6h; Inert atmosphere; Stage #3: 4,7-dibromobenzo[c][1,2,5]thiadiazole With tetrakis(triphenylphosphine) palladium(0) for 12h; Reflux; Inert atmosphere; | 47% |
| Stage #1: 3-undecylthieno[3,2-b]thiophene With n-butyllithium In tetrahydrofuran at 0℃; for 1.5h; Inert atmosphere; Stage #2: With trimethyltin(IV)chloride In tetrahydrofuran at 0 – 20℃; for 6h; Stage #3: 4,7-dibromobenzo[c][1,2,5]thiadiazole With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran for 12h; Reflux; Experimental Procedure 4.4.2 4,7-Bis(6-undecylthieno[3,2-b]thiophen-2-yl)benzothiadiazole (5) In a 250ml argon purged round flask, n-BuLi (2.88M, 18.89ml) was injected slowly by a syringe into a solution of compound 4 (16.0g, 54.4mmol) in THF (100ml) at 0°C, and then the mixture was stirred at this temperature for 1.5h. Subsequently, chlorotrimethylstannane (1.0M, 54.4ml) was added at 0°C and heated to room temperature for 6h, then 4,7-dibromobenzothiadiazole (6.76g, 23mmol) and Pd(PPh3)4 (2.65g, 2.3mmol) were added together into the solution and the mixture was refluxed for 12h. After cooled to room temperature, water (100ml) was added to the solution and extracted by chloroform twice, then the combined organic phase was concentrated. The residue was purified by chromatographic column using dichloromethane (10:1) as eluent to obtain compound 5 as deep red power (7.79g, yield 47%). 1H NMR (CDCl3, 400MHz), δ (ppm): δ 8.39 (s, 2H), 7.78 (s, 2H), 7.04 (s, 2H), 2.75 (t, J=6.9Hz, 4H), 1.78 (m, 4H), 1.51-1.14 (br, 32H), 0.88 (m, 6H). 13C NMR (CDCl3, 100MHz), δ (ppm): δ 152.48, 140.50, 140.18, 139.68, 135.17, 126.35, 125.36, 122.95, 121.00, 31.95, 29.97, 29.70, 29.67, 29.63, 29.46, 29.44, 29.39, 28.67, 22.72, 14.15. MS: m/z = 721. | 47% |
Safety and Hazards
| GHS Hazard Statements | No data available [Warning Hazardous to the aquatic environment, long-term hazard] Information may vary between notifications depending on impurities, additives, and other factors. |
| Precautionary Statement Codes | No data available (The corresponding statement to each P-code can be found at the GHS Classification page.) For more detailed information, please visit ECHA C&L website |
| Source: European Chemicals Agency (ECHA) License Note: Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: “Source: European Chemicals Agency, http://echa.europa.eu/”. Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page. License URL: https://echa.europa.eu/web/guest/legal-notice Record Name: (1-Cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino-carbenium hexafluorophosphate URL: https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/213446 Description: The information provided here is aggregated from the “Notified classification and labelling” from ECHA’s C&L Inventory. Read more: https://echa.europa.eu/information-on-chemicals/cl-inventory-database |
Other Data
| Transportation | No data available |
| Under the room temperature and away from light | |
| HS Code | 294200 |
| Storage | Under the room temperature and away from light |
| Shelf Life | 1 year |
| Market Price | USD 25/g |
| Druglikeness | |
| Lipinski rules component | |
| Molecular Weight | 294.525 |
| logP | 7.58 |
| HBA | 0 |
| HBD | 0 |
| Matching Lipinski Rules | 3 |
| Veber rules component | |
| Polar Surface Area (PSA) | 56.48 |
| Rotatable Bond (RotB) | 10 |
| Matching Veber Rules | 2 |
| Use Pattern |
| 3-undecylthieno[3,2-b]thiophene CAS#: 950223-97-9 is used as optoelectronic materials or intermediates. |
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