1689-77-6

Basic information

• Product Name: 2,5-Di-tert-butylthiophene
• Synonyms: 2,5-Di-tert-butylthiophene
• CAS NO: 1689-77-6
• Molecular Formula: C₁₂H₂₀S
• Molecular Weight: 196.3522
• Mol File: 1689-77-6.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 223.2°Cat760mmHg
• Flash Point: 63.1°C
• Appearance: /
• Density: 0.924g/cm³
• Vapor Pressure: 0.145mmHg at 25°C
• Refractive Index: 1.49
• CAS DataBase Reference: 2,5-Di-tert-butylthiophene(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Di-tert-butylthiophene(1689-77-6)
• EPA Substance Registry System: 2,5-Di-tert-butylthiophene(1689-77-6)

Safety Data

• Hazardous Substances Data: 1689-77-6(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 70, p. 3623, 1948 DOI: 10.1021/ja01191a025The Journal of Organic Chemistry, 49, p. 4161, 1984 DOI: 10.1021/jo00196a012

InChI:InChI=1/C12H20S/c1-11(2,3)9-7-8-10(13-9)12(4,5)6/h7-8H,1-6H3

Upstream product

• 1003-09-4 2-bromothiophene 
• 507-20-0 tertiary butyl chloride 
• 188290-36-0 thiophene 
• 67-64-1 acetone 
• 14630-42-3 (3,3-dimethyl-1-butynyl)trimethylsilane 
• 234773-08-1 3,6-bis(tert-butyl)-1,2-dithiin 
• 917-92-0 3,3-Dimethylbut-1-yne 
• 31681-44-4 2,5-di-tert-butylthiophene S-oxide 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 75-15-0 carbon disulfide 
• 7646-78-8 tin(IV) chloride 
• 142-82-5 n-heptane 
• 7705-08-0 iron(III) chloride 
• 86119-84-8 phosphoric acid 

Downstream Products

• 33369-81-2 2,4-di(tert-butyl)thiophene 
• 145083-23-4 2,3,4,5-Tetra-tert-butyl-thiophene 
• 2040-08-6 3,6-bis(tert-butyl)acetophenone 
• 40196-79-0 3,4-Dibrom-2,5-di-tert-butyl-thiophen 
• 6407-02-9 2,5-bis(tert-butyl)thiophene 1,1-dioxide 

Relevant articles and documents

Phthalimidosulphenyl chloride part 2. Synthesis of unusual thiirane derivatives

Vinylthio phthalimides 1, synthesized by addition of phtalimidosulphenyl chloride to some alkynes, react with 2 equivalents of lithiumtriethylboron hydride to give vinylthio substituted thiiranes 3 with high degree of diasteroselectivity. The reaction of

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Synthesis, properties, oxidation, and electrochemistry of 1,2- dichalcogenins

Syntheses are presented of the 1,2-dichalcogenins: 1,2-dithiin, 1,2- diselenin, and 2-selenathiin, both substituted and unsubstituted. 1,2-Dithiin and 1,2-diselenin are prepared by reaction of PhCH2XNa (X = S or Se) with 1,4-bis(trimethylsilyl)-1,3-butadiyne followed by reductive cleavage and oxidation. 2-Selenathiin is similarly prepared using a mixture of PhCH2SeNa and PhCH2SNa. Reaction of titanacyclopentadienes with (SCN)2 or (SeCN)2 followed by bis(thiocyanate) or bis(selenocyanate) cyclization affords substituted 1,2-dithiins or 1,2-diselenins, respectively. With S2Cl2, 1,2- dithiins are directly formed from titanacyclopentadienes. Oxidation of 1,2- dithiins and 1,2-diselenins gives the corresponding 1-oxide and, with 1,2- dithiins and excess oxidant, 1,1-dioxides; oxidation of 2-selenathiin gives the 2-oxide. Electrochemical oxidation of 1,2-dichalcogenins, which have a twisted geometry, affords planar radical cations by an EC mechanism. One- electron AlCl3 oxidation of 3,6-diphenyl-1,2-dithiin gives the corresponding radical cation, characterized by EPR spectroscopy. Theoretical calculations result in a flattened structure for the 1,2-dithiin radical cation and a fully planar structure for the 1,2-diselenin radical cation. The 77Se NMR chemical shifts of 1,2-diselenin are characteristically high-field-shifted with respect to open chain diselenides in good agreement with results of GIAO-DFT calculations based on MP2 and DFT optimum geometries.

A Convenient Synthesis of 1,2-Dithietes and 1,2-Dithioxo Compounds Stabilized by Buttressing and Resonance Effects, Respectively, by Sulfuration of Alkynes with Elemental Sulfur

Sulfuration of a series of alkynes by elemental sulfur was investigated.Alkynes carrying highly bulky substituents, 2,2,5,5-tetramethyl-3-hexyne (6a), 1,2-di-(1-adamantyl)ethyne (6b), 3,3-dimethyl-1-phenyl-1-butyne (6c), and 1-(1-adamantyl)-2-phenylethyne (6d), reacted with sulfur to give the corresponding stable 1,2-dithietes 7a-d in 46-65percent yields.Less hindered alkynes reacted with sulfur to afford 1,4-dithiins and thiophenes as the final products which were derived from the initial products, 1,2-dithietes, via their tautomerization to the corresponding 1,2-dithioxo compounds, while extremely congested alkynes failed to react with sulfur even under forcing conditions.On the other hand, ynamines, a typical electron-rich alkyne, 1-diethylamino-2-phenylthioethyne (6o), 1-diethylamino-2-phenylselenoethyne (6p), and tetraethylethynediamine (6q) were sulfurated under milder conditions to afford resonance-stabilized 1,2-dithioxo compounds 19o-q as the principal products.Mechanism of the formation of 1,2-dithietes, 1,2-dithioxo compounds, and other products is discussed.