2,5-Dimethylfuran-3-thiol

Base Information

• Chemical Name: 2,5-Dimethylfuran-3-thiol
• CAS No.: 55764-23-3
• Molecular Formula: C6H8OS
• Molecular Weight: 128.195
• Hs Code.: 29321900
• European Community (EC) Number: 259-800-5
• UNII: WCT2259X5L
• DSSTox Substance ID: DTXSID10204315
• Nikkaji Number: J75.520F
• Wikidata: Q27292562
• Metabolomics Workbench ID: 48896
• Mol file: 55764-23-3.mol

Synonyms:2,5-Dimethylfuran-3-thiol;55764-23-3;2,5-Dimethyl-3-furanthiol;3-Mercapto-2,5-dimethylfuran;3-FURANTHIOL, 2,5-DIMETHYL-;2,5-Dimethyl-3-mercaptofuran;FEMA No. 3451;2,5-Dimethyl-3-furylmercaptan;EINECS 259-800-5;UNII-WCT2259X5L;2,5-dimethyl-3-furan thiol;2,5-dimethyl-furan-3-thiol;WCT2259X5L;2.5-Dimethyl-3-furanthiol;SCHEMBL755488;2,5-Dimethyl-3-Mercapto Furan;FEMA 3451;DTXSID10204315;MFCD00801026;2,5-2-3-furan mercaptan methylation;AKOS006229372;DIMETHYL-3-FURANTHIOL, 2,5-;LS-2683;SB61020;2,5-dimethylfuran-3-thiol, AldrichCPR;2,5-DIMETHYL-3-FURANTHIOL [FHFI];D3764;FT-0654251;EN300-205666;A830796;Q-100645;Q27292562

Chemical Property of 2,5-Dimethylfuran-3-thiol

Chemical Property:

• Appearance/Colour: clear amber to orange liquid
• Vapor Pressure: 1.91mmHg at 25°C
• Refractive Index: 1.505-1.515
• Boiling Point: 170.9 ºC at 760 mmHg
• PKA: 6.43±0.50(Predicted)
• Flash Point: 57.2 ºC
• PSA: 51.94000
• Density: 1.092 g/cm³
• LogP: 2.18510
• Storage Temp.: Flammables area
• Water Solubility.: insoluble
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 128.02958605
• Heavy Atom Count: 8
• Complexity: 84.6

Purity/Quality:

99% ^*data from raw suppliers

2,5-Dimethylfuran-3-thiol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T,Xn
• Statements: 36/37/38-23/24/25-10-22-2017/10/22
• Safety Statements: 45-36/37/39-16-15

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=C(O1)C)S
• Description: 2,5-Dimethylfuran-3-thiol is a chemical substance known as an orange-red liquid. Its chemical structure consists of a furan ring with methyl groups at positions 2 and 5, along with a thiol group at position 3.
• Uses and Mechanism of Action: The production of the active metabolite (AM) from 2-oxoclopidogrel by human liver microsomes (HLMs) is greatly affected by the thiol reductants used. Among the 10 thiol compounds tested, glutathione (GSH) is most efficient in producing the AM at a rate of 167 pmoles AM/min/mg HLM. Interestingly, no AM but only the mixed disulfide conjugates were formed in the presence of 6-chloropyridazine-3-thiol (CPT), 2,5-dimethylfuran-3-thiol, and 3-nitropyridine-2-thiol (NPT). The mass spectrometry (MS) and MS2 spectra of the conjugates of these thiol compounds confirmed the presence of a mixed disulfide bond linkage between the AM and the thiol reductants. Kinetic studies revealed that the mixed disulfide conjugates were capable of exchanging thiols with GSH to release the AM with second order rate constants ranging from 1.2 to 28 M?1s?1. The mixed disulfide conjugates of CPT and NPT showed potent inhibition of platelet aggregation after pretreatment with 1 mM GSH, confirming that the AM is responsible for the antiplatelet activity of clopidogrel. ^[1]
• Handling Precautions: It can decompose to produce toxic fumes when burned or exposed to high temperatures. Due to its potentially hazardous properties, precautions such as the use of explosion-proof equipment, protective gear, and appropriate firefighting measures are necessary.
• References: [1] Formation, Reactivity, and Antiplatelet Activity of Mixed Disulfide Conjugates of Clopidogrel; DOI 10.1124/mol.112.084392

Technology Process of 2,5-Dimethylfuran-3-thiol

There total 8 articles about 2,5-Dimethylfuran-3-thiol 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: 62.0%

bis (2,5-dimethyl-furan-3-yl)-disulfide (28588-73-0) → 3-mercapto-2,5-dimethylfuran (55764-23-3)

Guidance literature:

With tributylphosphine; In water; isopropyl alcohol; for 0.5h;

DOI:10.1002/hlca.19930760711

Reference yield: 25.0%

2,5-dimethylfur-3-yl thiocyanate (149428-23-9) → 3-mercapto-2,5-dimethylfuran (55764-23-3) + 2'-mercaptoethyl 2,5-dimethylfur-3-yl sulfide + 2'-hydroxyethyl 2,5-dimethylfur-3-yl disulfide + bis (2,5-dimethyl-furan-3-yl)-disulfide (28588-73-0)

Guidance literature:

With potassium hydroxide; sodium dithionite; 2-hydroxyethanethiol; In water; for 0.5h;

DOI:10.1002/hlca.19930760711

Reference yield: 25.0%

2,5-dimethylfur-3-yl thiocyanate (149428-23-9) + 2-hydroxyethanethiol (60-24-2) → 3-mercapto-2,5-dimethylfuran (55764-23-3) + 2'-mercaptoethyl 2,5-dimethylfur-3-yl sulfide + 2'-hydroxyethyl 2,5-dimethylfur-3-yl disulfide + bis (2,5-dimethyl-furan-3-yl)-disulfide (28588-73-0)

Guidance literature:

With potassium hydroxide; sodium dithionite; In water; for 0.5h;

DOI:10.1002/hlca.19930760711

upstream raw materials:

2,5-dimethylfur-3-yl thiocyanate

bis (2,5-dimethyl-furan-3-yl)-disulfide

2-hydroxyethanethiol

S-(2,5-dimethylfur-3-yl) thioacetate

Downstream raw materials:

2-benzyl-5-(2,5-dimethyl-furan-3-ylsulfanylmethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-ol

Refernces

• 1、 -. "Process for the manufacture of furan derivatives". . . Retrieved 2008/06/13.
• 2、 -. "Certain 3-furyl sulfides". . . Retrieved 2008/06/13.