1708-32-3

Basic information

• Product Name: 2,5-Dihydrothiophene
• Synonyms: 2,5-Dihydrothiophene
• CAS NO: 1708-32-3
• Molecular Formula: C4H6S
• Molecular Weight: 86.1554
• Mol File: 1708-32-3.mol
• Article Data: 21

Chemical Properties

• Melting Point: -49.3°C
• Boiling Point: 122.4°C
• Flash Point: 23.5°C
• Appearance: /
• Density: 0.972 (estimate)
• Vapor Pressure: 18.7mmHg at 25°C
• Refractive Index: 1.4800 (estimate)
• CAS DataBase Reference: 2,5-Dihydrothiophene(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Dihydrothiophene(1708-32-3)
• EPA Substance Registry System: 2,5-Dihydrothiophene(1708-32-3)

Safety Data

• Hazardous Substances Data: 1708-32-3(Hazardous Substances Data)

Usage

Uses

2,5-Dihydrothiophene is mainly used in organic synthesis and pharmaceutical intermediates.

Preparation

2,5-Dihydrothiophene can be obtained in reasonable yield by reaction of cis-1,4-dichloro-2-butene with anhydrous sodium sulfide in a mixture of methanol and dimethyl sulfoxide.

InChI:InChI=1/C4H6S/c1-2-4-5-3-1/h1-2H,3-4H2

Upstream product

• 40018-26-6 1,4-dithiane-2,5-diol 
• 5044-52-0 vinyltriphenylphosphonium bromide 
• 188290-36-0 thiophene 
• 67-56-1 methanol 
• 7664-41-7 ammonia 
• 52-90-4 L-Cysteine 
• 178101-88-7 [1-¹³C]ascorbic acid 
• 50-81-7 ascorbic acid 
• 592-88-1 diallyl sulphide 
• 689-97-4 3-buten-1-yne 

Downstream Products

• 110-01-0 thiophene 
• 77-79-2 3-Sulfolene 
• 14176-47-7 trans-3,4-dihydroxytetrahydrothiophene-1,1-dioxide 
• 69520-31-6 1-phenacyl-2,5-dihydrothiophenium bromide 
• 14852-22-3 2,5-dihydrothiophene 1-oxide 
• 106-99-0 buta-1,3-diene 

Relevant articles and documents

Synthesis of sulphur-containing heterocycles by ring closing diene metathesis

We have shown that, surprisingly, the Schrock molybdenum alkylidene catalyst 1 can perform ring closing metathesis reactions on substrates containing a sulphide group, converting diallyl sulphide 5 to 2,5-dihydrothiophene 6 with >99% conversion. By contrast, the ruthenium alkylidene catalyst 2, which is generally more tolerant of functional groups in the substrate, is unreactive towards diallylsulphide. However even the molybdenum catalyst 1 proved unable to catalyse ring closure of tetrathiafulvalene derivative 7.

Highly efficient Ru-pseudohalide catalysts for olefin metathesis

Ruthenium alkylidene complexes containing one aryloxide "pseudohalide" ligand catalyze ring-closing metathesis of diene and ene-yne substrates with exceptionally high efficiency. Chromatographic removal of Ru residues is unexpectedly facile, offering a convenient means of isolating pure organic products in high yields. Copyright

N-Heterocyclic Carbene Complexes Of Metal Imido Alkylidenes And Metal OXO Alkylidenes, And The Use Of Same

The invention relates to an N-heterocyclic carbene complex of general formulas I to IV (I) (II) (III) (IV), according to which A1 stands for NR2 or PR2, A2 stands for CR2 R2′, NR2, PR2, 0 or S, A3 stands for N or P, and C stands for a carbene carbon atom, ring B is an unsubstituted or a mono or poly-substituted 5 to 7-membered ring, substituents R2 and R2′ stand, inter alia, for a linear or branched C1-Cw-alkyl group and, if N and N each stand for NR2 or PR2, are the same or different, M in formulas I, II, III or IV stands for Cr, Mo or W, X 1 or X2 in formulas I to IV are the same or different and represent, inter alia, C1-C1s carboxylates and C1-C1s-alkoxides, Y is inter alia oxygen or sulphur, Z is inter alia a linear or branched C1-Cw-alkylenoxy group, and R 1 and R1′ in formulas I to IV are, inter alia, an aliphatic or aromatic group. These compounds are particularly suitable for use as catalysts for olefin metathesis reactions and have the advantage, compared to known Schrock carbene complexes, of displaying clearly increased tolerance to functional groups such as, in particular, aldehydes, secondary amines, nitriles, carboxylic acids and alcohols.

Grubbs-Hoveyda type catalysts bearing a dicationic N-heterocyclic carbene for biphasic olefin metathesis reactions in ionic liquids

The novel dicationic metathesis catalyst [(RuCl2(H2ITapMe2)(=CH-2-(2-PrO)-C6H4))2+(OTf-)2] (Ru-2, H2ITapMe2 = 1,3-bis(2',6'-dimethyl-4'-trimethylammoniumphenyl)-4,5-dihydroimidazol-2-ylidene, OTf- = CF3SO3-) based on a dicationic N-heterocyclic carbene (NHC) ligand was prepared. The reactivity was tested in ring opening metathesis polymerization (ROMP) under biphasic conditions using a nonpolar organic solvent (toluene) and the ionic liquid (IL) 1-butyl-2,3-dimethylimidazolium tetrafluoroborate [BDMIM+][BF4-]. The structure of Ru-2 was confirmed by single crystal X-ray analysis.