3-Methyl-2,5-dihydrothiophene 1,1-dioxide

Base Information

• Chemical Name: 3-Methyl-2,5-dihydrothiophene 1,1-dioxide
• CAS No.: 1193-10-8
• Molecular Formula: C5H8 O2 S
• Molecular Weight: 132.183
• Hs Code.: 2934999090
• European Community (EC) Number: 214-765-5
• NSC Number: 15090
• UNII: ND7G34ZF4C
• DSSTox Substance ID: DTXSID4061597
• Nikkaji Number: J80.074K
• Wikidata: Q27161636
• Mol file: 1193-10-8.mol

Synonyms:1193-10-8;3-Methylsulfolene;3-Methyl-2,5-dihydrothiophene 1,1-dioxide;3-Methyl-3-sulfolene;3-METHYL-2,5-DIHYDROTHIOPHENE-1,1-DIOXIDE;3-methyl sulfolene;Thiophene, 2,5-dihydro-3-methyl-, 1,1-dioxide;3-Methyl-2,5-dihydrothiophene dioxide;NSC 15090;1,3-Butadiene, 2-methyl-, sulfone;C5H8O2S;AI3-23650;EINECS 214-765-5;NSC-15090;3-Methyl-2,5-dihydrothiophene1,1-dioxide;2,5-Dihydro-3-methylthiophene 1,1-dioxide;2,5-Dihydro-3-methyl-thiophene 1,1-dioxide;NSC15090;I+/--Isoprensulfon;3-Methyl-2,1-dioxide;1, 2-methyl-, sulfone;ND7G34ZF4C;SCHEMBL1352528;DTXSID4061597;CHEBI:89440;MFCD00005482;STK370726;AKOS000269391;3-methyl-1,1-dioxido-2,5-dihydrothiophene;CS-0324826;FT-0633451;3-methyl-2,5-dihydro-thiophene 1,1-dioxide;Thiophene,5-dihydro-3-methyl-, 1,1-dioxide;Thiophene,2,5-dihydro-3-methyl-,1,1-dioxide;2,5-Dihydrothiophene, 1,1-dioxide, 3-methyl-;2,5-Dihydro-3-methylthiophene 1,1-dioxide, 99%;A804252;J-004097;Q27161636

Chemical Property of 3-Methyl-2,5-dihydrothiophene 1,1-dioxide

Chemical Property:

• Vapor Pressure: 0.00322mmHg at 25°C
• Melting Point: 62-64°C
• Refractive Index: 1.5160 (estimate)
• Boiling Point: 292.4°C at 760 mmHg
• Flash Point: 171.9°C
• PSA: 42.52000
• Density: 1.24g/cm³
• LogP: 1.44190
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 132.02450067
• Heavy Atom Count: 8
• Complexity: 205

Purity/Quality:

98%,99%, ^*data from raw suppliers

3-Methyl-2,5-dihydrothiophene-1,1-dioxide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CCS(=O)(=O)C1
• Uses: 3-Methyl-2,5-dihydrothiophene-1,1-dioxide is a reagent used in Diels-Alder reactions of butadienylpyridinium bromides. Chemical intermediate, catalyst.

Technology Process of 3-Methyl-2,5-dihydrothiophene 1,1-dioxide

There total 9 articles about 3-Methyl-2,5-dihydrothiophene 1,1-dioxide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

isoprene (78-79-5,9003-31-0) → 3-methyl-2,5-dihydrothiophen-1,1-dioxide (1193-10-8)

Guidance literature:

With sodium metabisulfite; potassium hydrogensulfate; In methanol; water; at 100 ℃; for 14h; under 517.162 - 1034.32 Torr; Reagent/catalyst; Solvent; Temperature; Sealed tube;

DOI:10.1039/c8ob00745d

Reference yield: 96.0%

3-Methyl-3-(phenylsulfonyl)-2,3-dihydrothiophene 1,1-dioxide (127844-17-1) → 3-methyl-2,5-dihydrothiophen-1,1-dioxide (1193-10-8)

Guidance literature:

With sodium amalgam; phosphoric acid; In tetrahydrofuran; Ambient temperature;

DOI:10.1016/S0040-4039(00)94423-X

Reference yield: 25.0%

4-bromo-3-methyl-2-sulfolene (65017-48-3) → 3-methyl-2,5-dihydrothiophen-1,1-dioxide (1193-10-8) + 2-n-butyl-3-methyl-3-sulfolene (105246-98-8)

Guidance literature:

In tetrahydrofuran; at -78 ℃; for 2h;

DOI:10.1021/jo00391a042

upstream raw materials:

3-methyl-2,5-dihydro-thiophene

isoprene

3-Methyl-3-(phenylsulfonyl)-2,3-dihydrothiophene 1,1-dioxide

ethanol

Downstream raw materials:

4-acrylamido-4-methyltetrahydrothiophene-3-sulfonic acid 1,1-dioxide

4-methyl-2,3-dihydro-thiophene 1,1-dioxide

isoprene

2-methyl-3-(phenylthio)-1,3-butadiene

Refernces

• 1、 Bertolini, Thomas M,Nguyen, Que Huong,Harvey, Daniel F. "Construction of [4.3.1]propellanes via molybdenum fischer carbene complexes.". . p. 8675 - 8678. Retrieved 2002.
• 2、 Martial, Ludovic,Bischoff, Laurent. "Stoichiometric release of SO2 from adducts: Application to the direct synthesis of protected dienes". . p. 1225 - 1229. Retrieved 2015.
• 3、 Dang, Hang T.,Nguyen, Vu T.,Nguyen, Viet D.,Arman, Hadi D.,Larionov, Oleg V.. "Efficient synthesis of 3-sulfolenes from allylic alcohols and 1,3-dienes enabled by sodium metabisulfite as a sulfur dioxide equivalent". supporting information. p. 3605 - 3609. Retrieved 2018/05/26.