75503-13-8

Basic information

• Product Name: 3,3,6,6-Tetramethylbicyclo[2.2.1]heptane-2-one-5-thione
• Synonyms: 3,3,6,6-Tetramethylbicyclo[2.2.1]heptane-2-one-5-thione
• CAS NO: 75503-13-8
• Molecular Formula: C11H16 O S
• Molecular Weight: 0
• Mol File: 75503-13-8.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 272.1°C at 760 mmHg
• Flash Point: 118.4°C
• Appearance: /
• Density: 1.1g/cm³
• Vapor Pressure: 0.00619mmHg at 25°C
• Refractive Index: 1.545
• CAS DataBase Reference: 3,3,6,6-Tetramethylbicyclo[2.2.1]heptane-2-one-5-thione(CAS DataBase Reference)
• NIST Chemistry Reference: 3,3,6,6-Tetramethylbicyclo[2.2.1]heptane-2-one-5-thione(75503-13-8)
• EPA Substance Registry System: 3,3,6,6-Tetramethylbicyclo[2.2.1]heptane-2-one-5-thione(75503-13-8)

Safety Data

• Hazardous Substances Data: 75503-13-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H16OS/c1-10(2)7-5-6(8(10)12)11(3,4)9(7)13/h6-7H,5H2,1-4H3

Upstream product

• 57239-03-9 3,3,6,6-tetramethylbicyclo<2.2.1>heptane-2.5-dione 

Relevant articles and documents

Synthesis of bicyclic diones and thiones. Facile methylation of the enolates of bicycloheptane-2,5-dione and bicyclooctane-2,5-dione. An AM1 computational study of bicyclic enolates

A group of bicyclic ketones and thiones have been synthesized for homenolization studies.Bicycloheptane-2,5-dione (6) undergoes unusually rapid tetramethylation giving 3,3,6,6-tetramethylbicycloheptane-2,5-dione (1) in good yield.Treatment of 1 with P2S5 in xylene gave 3,3,6,6-tetramethylbicycloheptane-2,5-dithione (2) and 3,3,6,6-tetramethyl-5-oxo-bicycloheptane-2-thione (3), which was converted into 4 with Raney nickel.Bicyclooctane-2,5-dione (7), prepared via Diels-Alder reaction between 2-trimethylsilyloxy-1,3-cyclohexadiene and α-acetoxyacrylonitrile followed by a one-step desilylation/hydrolysis, also undergoes facile tetramethylation giving 3,3,6,6-tetramethylbicyclooctane-2,5-dione (5) in good yields.AM1 calculations were carried out on the α-enolates of bicycloheptan-2-one, 6, 5-methylidenebicycloheptan-2-one, and 4-acetylbicycloheptan-2-one in an attempt to gain information on the source of the enhanced acidity of the C-3 hydrogens of 6 and 7. Key words: bicyclic ketones, thiones, synthesis.