21856-74-6

Basic information

• Product Name: 2,8-Dibenzylidenecyclooctanone
• Synonyms: 2,8-Dibenzylidenecyclooctanone
• CAS NO: 21856-74-6
• Molecular Formula: C₂₂H₂₂O
• Molecular Weight: 0
• Mol File: 21856-74-6.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 493.7°Cat760mmHg
• Flash Point: 216.7°C
• Appearance: /
• Density: 1.103g/cm³
• Vapor Pressure: 6.88E-10mmHg at 25°C
• Refractive Index: 1.636
• CAS DataBase Reference: 2,8-Dibenzylidenecyclooctanone(CAS DataBase Reference)
• NIST Chemistry Reference: 2,8-Dibenzylidenecyclooctanone(21856-74-6)
• EPA Substance Registry System: 2,8-Dibenzylidenecyclooctanone(21856-74-6)

Safety Data

• Hazardous Substances Data: 21856-74-6(Hazardous Substances Data)

Usage

Physical state

Yellowish to brown crystalline solid

Use in organic synthesis

As a ligand for metal catalysts

Industrial application

Widely used in the pharmaceutical industry for the production of various drugs and as a key intermediate in the synthesis of various bioactive compounds

Potential properties

Studied for its potential anticancer, anti-inflammatory, and antioxidant properties

Other uses

Used in the production of dyes, perfumes, and other specialty chemicals.

InChI:InChI=1/C22H22O/c23-22-20(16-18-10-4-1-5-11-18)14-8-3-9-15-21(22)17-19-12-6-2-7-13-19/h1-2,4-7,10-13,16-17H,3,8-9,14-15H2/b20-16+,21-17+

Upstream product

• 502-49-8 cycloactanone 
• 100-52-7 benzaldehyde 
• 108-94-1 cyclohexanone 

Downstream Products

• 34403-32-2 cis-2,8-Dibenzylcyclooctanon 
• 34403-32-2 trans-2,8-Dibenzylcyclooctanon 
• 77109-59-2 4-Phenyl-10-[1-phenyl-meth-(E)-ylidene]-3,4,5,6,7,8,9,10-octahydro-1H-cyclooctapyrimidine-2-thione 
• 77109-77-4 5-Phenyl-11-[1-phenyl-meth-(E)-ylidene]-2,3,6,7,8,9,10,11-octahydro-5H-1-thia-4a,12-diaza-cycloocta[b]naphthalen-4-one 
• 77109-65-0 4-Phenyl-10-[1-phenyl-meth-(E)-ylidene]-5,6,7,8,9,10-hexahydro-4H-1-thia-3a,11-diaza-cycloocta[f]inden-3-one 

Relevant articles and documents

Cycloalkanones V: Synthesis, distribution, and effects on triglyceride metabolism

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The synthesis and chlorosulfonation of some diarylidene and heteroarylidene ketones with varying alicyclic ring size

A series of diarylidene and heteroarylidene ketones (1-20) was prepared using alicyclic ketones ((CH2)nC=O where n=3 to 7).An improved synthesis of 2,4-dibenzylidenecyclobutanone (1) is described and the ease of preparation of the arylidene derivatives is considered in terms of the size of the alicyclic ring.Treatment of 2,5-dibenzylidenecyclopentanone (2) with chlorosulfonic acid (10 mole equivalents) afforded the 4,4'-bis-sulfonyl chloride (23), reducing the amount of chlorosulfonis acid (6 mole equivalents) produced the corresponding mono-sulfonyl chloride (24).Only the respective 4,4'-bis-sulfonyl chlorides (39, 45, 51) could be isolated from the diarylidene ketones derived from larger alicyclic rings.Attempted chlorosulfonation of 2,4-dibenzylidene cyclobutanone (1) gave a mixture of products which could not be clearly characterised.The sulfonyl chlorides were converted into stable sulfonamides (25-29, 35, 36, 38, 40-44, 46-48, 52, 54) by condensation with amines, and selected samples were screened for biological activity as potential insecticides, herbicides, and fungicides.The orientation of sulfonation is discussed in relation to stereoelectronic factors and the relevant spectral data.Key words: Arylidene and heteroarylidene ketones, chlorosulfonation, sulfonamides