5693-95-8

Basic information

• Product Name: 6-Thioxopiperidine-2-one
• Synonyms: 6-Thioxo-2-piperidone;6-Thioxopiperidine-2-one;USAF WI-5
• CAS NO: 5693-95-8
• Molecular Formula: C₅H₇NOS
• Molecular Weight: 129.1802
• Mol File: 5693-95-8.mol
• Article Data: 7

Chemical Properties

• Melting Point: 118-119 °C(Solv: benzene (71-43-2))
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.25g/cm³
• Refractive Index: 1.576
• PKA: 9.20±0.20(Predicted)
• CAS DataBase Reference: 6-Thioxopiperidine-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Thioxopiperidine-2-one(5693-95-8)
• EPA Substance Registry System: 6-Thioxopiperidine-2-one(5693-95-8)

Safety Data

• Hazardous Substances Data: 5693-95-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C5H7NOS/c7-4-2-1-3-5(8)6-4/h1-3H2,(H,6,7,8)

Upstream product

• 325956-77-2 N-3,4-dimethyl-3-pentenylmonothioglutarimide 
• 1121-89-7 piperidine-2,6-dione 

Downstream Products

• 78312-57-9 2,3,5,6,7,8-Hexahydro-5-thioxo-indolizin-1-carbonsaeure-ethylester 
• 78312-54-6 4-(2-Oxo-5-thioxo-1-piperidinyl)-2-triphenylphosphorandiylbuttersaeure-ethylester 
• 77784-29-3 2,3,5,6,7,8-Hexahydro-5-oxo-indolizin-1-carbonsaeure-ethylester 
• 80362-98-7 2-(4-Chlorophenyl)-5,6,7,8-tetrahydro-3-hydroxythiazolo[3,2-a]-pyridinium bromide 

Relevant articles and documents

Lewis acid enhanced axial ligation of [Mo2]4+ complexes

We report here the syntheses, X-ray crystal structures, electrochemistry, and density functional theory (DFT) single-point calculations of three new complexes: tetrakis(monothiosuccinimidato)dimolybdenum(II) [Mo 2(SNO5)4, 1a], tetrakis(6-thioxo-2-piperidinonato) dimolybdenum(II) [Mo2(SNO6)4, 1b], and chlorotetrakis(monothiosuccinimidato)pyridinelithiumdimolybdenum(II) [pyLiMo2(SNO5)4Cl, 2-py]. X-ray crystallography shows unusually short axial Mo2-Cl bond lengths in 2-py, 2.6533(6) A, and dimeric 2-dim, 2.644(1) A, which we propose result from an increased Lewis acidity of the Mo2 unit in the presence of the proximal Li + ion. When 2-py is dissolved in MeCN, the lithium reversibly dissociates, forming an equilibrium mixture of (MeCNLiMo2(SNO5) 4Cl) (2-MeCN) and [Li(MeCN)4]+[Mo 2(SNO5)4Cl]- (3). Cyclic voltammetry was used to determine the equilibrium lithium binding constant (room temperature, K eq = 95 ± 1). From analysis of the temperature dependence of the equilibrium constant, thermodynamic parameters for the formation of 2-MeCN from 3 (ΔH = -6.96 ± 0.93 kJ mol-1 and ΔS = 13.9 ± 3.5 J mol-1 K-1) were extracted. DFT calculations indicate that Li+ affects the Mo-Cl bond length through polarization of metal-metal bonding/antibonding molecular orbitals when lithium and chloride are added to the dimolybdenum core.

A thionation process and a thionating agent

A process for transforming a group >C=O (I) in a compound into a group >C=S (II) or into a tautomeric form of group (II) in a reaction giving a thionated reaction product, by use of crystalline P2S5·2 C5H5N as a thionating agent. A thionating agent which is crystalline P2S5·2 C5H5N.

THALIDOMIDE ANALOGS

Thalidomide analogs that modulate tumor necrosis factor alpha (TNF-α) activity and angiogenesis are disclosed. In particularly disclosed embodiments, the thalidomide analogs are isosteric sulfur-containing analogs. Also disclosed are methods of treating a subject with the analogs.