85923-37-1

Basic information

• Product Name: 3,6-dimethylcholanthrene
• Synonyms: 3,6-dimethylcholanthrene
• CAS NO: 85923-37-1
• Molecular Formula: C22H18
• Molecular Weight: 282.40
• Mol File: 85923-37-1.mol

Chemical Properties

• Boiling Point: 504.99°C (rough estimate)
• Flash Point: 260.8°C
• Appearance: /
• Density: 1.0848 (estimate)
• Vapor Pressure: 2.7E-10mmHg at 25°C
• Refractive Index: 1.7810 (estimate)
• CAS DataBase Reference: 3,6-dimethylcholanthrene(CAS DataBase Reference)
• NIST Chemistry Reference: 3,6-dimethylcholanthrene(85923-37-1)
• EPA Substance Registry System: 3,6-dimethylcholanthrene(85923-37-1)

Safety Data

• Hazardous Substances Data: 85923-37-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C22H18/c1-13-7-9-17-14(2)21-18-6-4-3-5-15(18)8-10-19(21)20-12-11-16(13)22(17)20/h3-10H,11-12H2,1-2H3

Upstream product

• 90823-01-1 Methyl 2-(4-Methylindan-1-yl)-1-naphthyl Ketone 
• 85923-38-2 3,6-dimethylcholanthrene picrate 

Relevant articles and documents

Syntheses of 3,6-Dimethylcholanthrene, 3,6-Dimethyl-7-methoxycholanthrene, and 7-Methoxy-3-methylcholanthrene

The condensations of 2-lithio-N,N-diethyl-1-naphthamide and 2-lithio-N,N-diethyl-8-methoxy-1-naphthamide with 4-methyl-1-indanone, followed by hydrolysis, afforded 2-(1-hydroxy-4-methylindan-1-yl)-1-naphthoic acid lactone (6) and 2-(1-hydroxy-4-methylindan-1-yl)-8-methoxy-1-naphthoic acid lactone (6a), respectively.Reduction of 6 followed by esterification yielded methyl 2-(4-methylindan-1-yl)-1-naphthoate (7a) which by reaction with methyllithium in ether-hexamethylphosphoramide yielded methyl 2-(4-methylindan-1-yl)-1-naphthyl ketone (8).Treatment of 8 with hydrogenfluoride yielded 3,6-dimethylcholanthrene (1).Treatment of 8 with 57 percent hydroiodic acid and phosphorus yielded 6,12-dihydro-3,6-dimethylcholanthrene which could readily be oxidized to 3,6-dimethylcholanthrene (1).The lactone 6a was reduced to 2-(4-methylindan-1-yl)-8-methoxy-1-naphthoic acid (9).Treatment of 9 with oxalyl chloride followed by reduction with triethylsilane and trifluoroacetic acid yielded a crude product which contained 2-(4-methylindan-1-yl)-8-methoxy-1-naphthaldehyde since it afforded 7-methoxy-3-methylcholanthrene (3) on treatment with polyphosphoric acid (PPA).Alternately, methyl 2-(4-methylindan-1-yl)-8-methoxy-1-naphthoate gave 7-methoxy-3-methylcholanthrene on treatment with PPA.Treatment of 9 with 57 percent hydroiodic acid as above gave 8-hydroxy-2-(4-methylindan-1-yl)-1-naphthoic acid lactone (11).Treatment of the acid chloride of 9 with dimethylcuprate yielded methyl 2-(4-methylindan-1-yl)-8-methoxy-1-naphthyl ketone (8a), which by HF cyclization afforded 3,6-dimethyl-7-methoxycholanthrene (2).