22808-03-3

Basic information

• Product Name: 3,4-Di-tert-butylthiophene
• Synonyms: 3,4-Di-tert-butylthiophene
• CAS NO: 22808-03-3
• Molecular Formula: C₁₂H₂₀S
• Molecular Weight: 196.35
• Mol File: 22808-03-3.mol
• Article Data: 14

Chemical Properties

• Melting Point: 43-43.5 °C
• Boiling Point: 75 °C(Press: 4 Torr)
• Appearance: /
• Density: 0.924±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 3,4-Di-tert-butylthiophene(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-Di-tert-butylthiophene(22808-03-3)
• EPA Substance Registry System: 3,4-Di-tert-butylthiophene(22808-03-3)

Safety Data

• Hazardous Substances Data: 22808-03-3(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron Letters, 29, p. 1161, 1988 DOI: 10.1016/S0040-4039(00)86677-0

Upstream product

• 5469-26-1 1-Bromopinacolon 
• 75-97-8 3,3-dimethyl-butan-2-one 
• 116375-55-4 3,4-di-tert-butyl-tetrahydrothiophene-3,4-diol 
• 52196-65-3 1,1'-thiobis(3,3-dimethylbutan-2-one) 
• 118888-09-8 3,4-Di-tert-butylthiophene S-oxide 
• 6262-42-6 1,2,3,3-tetrachlorocyclopropene 
• 3189-43-3 tetracyanoethylene oxide 
• 746646-01-5 C₁₂H₂₀Cl₂OS₃ 
• 581776-45-6 (3aR,6aS)-3a,6a-di(tert-butyl)tetrahydrothienol[3,4-d][1,3,2]dioxathiolate 
• 581776-38-7 (3aR,6aS)-3a,6a-di(tert-butyl)tetrahydrothieno[3,4-d][1,3,2]dioxathiolate 2-sulfide 
• 23695-65-0 adamantane-2-thione 
• 116375-55-4 cis-3,4-di-(tert-butyl)tetrahydrothiophene-3,4-diol 
• 134132-40-4 4,5-Di-tert-butyl-6-oxa-2-thia-bicyclo[3.1.0]hex-3-ene 2,2-dioxide 
• 116375-45-2 3,4-di-tert-butyl-thiophene 1,1-dioxide 

Downstream Products

• 243123-91-3 3,4-di-tert-butyl-1-[(p-tolylsulfonyl)imino]-1,1-dihydrothiophene 
• 130826-16-3 1-(p-tolylsulfonyl)-3,4-di-tert-butylpyrrole 
• 33369-81-2 2,4-di(tert-butyl)thiophene 

Relevant articles and documents

Synthesis of π-conjugated copolymers composed of benzo[2,1,3]thiadiazole and thiophene units bearing various alkyl groups and their application to photovoltaic cells

π-Conjugated polymers, PTOTBT, PTEHTBT, and PTt-BTBT, composed of benzothiadiazole as an electron accepting unit and terthiophene as an electron donating unit in the backbone were prepared. PTOTBT, PTEHTBT, and PTt-BTBT contained side chain groups of n-octyl, 2-ethylhexyl, and t-butyl groups, respectively. Solubility, optical and thermal properties of the polymers showed strong dependences on their side chain groups. PTEHTBT having 2-ethylhexyl groups in the side chain exhibited absorption maximum (Imax) at longer wavelength (565 nm) than PTOTBT (534 nm) and PTt-BTBT (495 nm). PTOTBT showed higher thermal stability than the others. The prepared polymers were employed to polymer solar cells (PSCs) with a configuration of ITO/PEDOT-PSS/polymer: PC61BH/LiF/Al. Power conversion efficiency of the PSC-based on PTEHTBT was 1.32%.

Synthesis of an octa-tert-butylphthalocyanine: A low-aggregating and photochemically stable photosensitizer

The synthesis of a new octa-tert-butylphthalocyanine is described. First, the 4,5-di-tert-butylphthalonitrile building block was synthesized in a six-step approach, in which the last step is a three reaction domino sequence. Then, this phthalonitrile was cyclotetramerized to furnish a new phthalocyanine dye, which presented no aggregation in solution and good photophysical properties. The synthesis of a new octa-tert-butylphthalocyanine is described. First, the 4,5-di-tert-butylphthalonitrile building block was synthesized in a six-step approach, in which the last step is a three reaction domino sequence. Then, this phthalonitrile was cyclotetramerized to furnish a new phthalocyanine dye, which presented no aggregation in solution and good photophysical properties. Copyright

The chemistry of the thiosulfinyl group: Preparation, structure, and spectroscopic and chemical properties of cyclic thionosulfites

Treatment of the tetrahydrothiophene-3,4-diol 5 with 1,1′-thiobis- (1H-benzimidazole) (6) furnished two diastereoisomers of the novel cyclic thionosulfite 4 with different configurations at the pseudo-tetrahedral center of the thiosulfinyl (S=S) group. The configuration of the S=S group of the major diastereoisomer (isolated in 45% yield) was established to be syn to the thiolane ring, as determined by X-ray crystallographic analysis, while that of the minor diastereoisomer (isolated in 10% yield) was anti. 1H-NMR Spectroscopic analysis clarified that the shielding and deshielding zones of the S=S group are similar to those of the well-documented S=O group. Characteristic absorptions of the S=S group in the IR, Roman, and UV/VIS spectra were assigned on the basis of calculations at the B3LYP/6-31G* level. The reactivity of the S=S group toward thermolysis, hydrolysis, and oxidation was examined. The S=S group is more resistant toward oxidation than the divalent sulfide S-atom, but is oxidatively converted to the S=O group.

So2-extrusion of an 8-thiabicylo[3.2.1]octa-2,6-diene 8,8-dioxide and rearrangement of the resulting cycloheptatriene

The reaction of 3,4-di-tert-butylthio-phene 1-oxide (8) with tetrachlorocyclopropene provided 6,7-di-tert-butyl-2,3,4,4-tetrachloro-8-thia- bicylo[3.2.1]-octa-2,6-diene 8-oxide (10), which was oxidized to the corresponding 8,8-dioxide 16 by m-chloroperbenzoic acid. The thermolysis of 16 in refluxing chlorobenzene, xylene, or octane gave 5-tert-butyl-1,2-dichloro-3- [(1,1-dichloro-2,2-dimethyl)propyl]benzene (18) with extrusion of SO2 and 2-tert-butyl-4,5,6-trichloro-9,9-dimethylbicyclo[5.2.0]nona-1,3,5-triene (19) with extrusion of SO2 and HCl in 73-78% combined yields. On the other hand, the thermolysis of 16 in the presence of triethylamine gave 19 as the sole product in 98% yield. A mechanism that involves the initial formation of 4,5-di-tert-butyl-1,2,7,7-tetrachlorocycloheptatriene (17) is proposed to explain the observed products.