3-undecylthieno[3,2-b]thiophene CAS#: 950223-97-9; 凯望编码 (ChemWhat Code): 1372851

IdentificationPhysical DataSpectra
Route of Synthesis (ROS)Safety and HazardsOther Data

Identification

英文名3-undecylthieno[3,2-b]thiophene
IUPAC Name6-undecylthieno[3,2-b]thiophene
分子结构Structure of 3-undecylthieno[3,2-b]thiophene CAS 950223-97-9
CAS编号 950223-97-9
EINECS NumberNo data available
MDL NumberNo data available
Beilstein Registry NumberNo data available
别名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
分子式C17H26S2
分子量294.518
InChIInChI=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 KeyBVCVLQZKDYRAHL-UHFFFAOYSA-N
Canonical SMILESCCCCCCCCCCCc1csc2c1scc2
Patent Information
No data available

Physical Data

AppearanceColorless liquid
SolubilityNo data available
Flash PointNo data available
Refractive indexNo data available
SensitivityNo 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 shifts1Hchloroform-d1400
Chemical shifts1Hchloroform-d1100
3-undecylthieno[3,2-b]thiophene CAS#: 950223-97-9 HNMRHNMR of 3-undecylthieno[3,2-b]thiophene CAS 950223-97-9
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
Route of Synthesis (ROS) of 3-undecylthieno[3,2-b]thiophene CAS# 950223-97-9
ConditionsYield
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 StatementsNo 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 CodesNo 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

TransportationNo data available
Under the room temperature and away from light
HS Code294200
StorageUnder the room temperature and away from light
Shelf Life1 year
Market PriceUSD 25/g
Druglikeness
Lipinski rules component
分子量294.525
logP7.58
HBA0
HBD0
Matching Lipinski Rules3
Veber rules component
Polar Surface Area (PSA)56.48
Rotatable Bond (RotB)10
Matching Veber Rules2
Use Pattern
3-undecylthieno[3,2-b]thiophene CAS#: 950223-97-9 is used as optoelectronic materials or intermediates.

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