483-78-3

Basic information

• Product Name: CADALENE
• Synonyms: 1,6-Dimethyl-4-isopropylnaphthaIene;1,6-dimethyl-4-isopropylnaphthalene;4-(1-methylethyl)-1,6-dimethylnaphthalene;4-Isopropyl-1,6-dimethylnaphthalene;Cadalin;Naphthalene, 4-isopropyl-1,6-dimethyl-;naphthalene,1,6-dimethyl-4-(1-methylethyl)-;CADALENE
• CAS NO: 483-78-3
• Molecular Formula: C₁₅H₁₈
• Molecular Weight: 198.3
• Mol File: 483-78-3.mol
• Article Data: 6

Chemical Properties

• Melting Point: -14.17°C (estimate)
• Boiling Point: bp720 291-292°; bp10 149°
• Flash Point: 140.3°C
• Appearance: /
• Density: d425 0.9667
• Vapor Pressure: 0.00173mmHg at 25°C
• Refractive Index: nD25 1.5785
• CAS DataBase Reference: CADALENE(CAS DataBase Reference)
• NIST Chemistry Reference: CADALENE(483-78-3)
• EPA Substance Registry System: CADALENE(483-78-3)

Safety Data

• Hazardous Substances Data: 483-78-3(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 72, p. 3468, 1950 DOI: 10.1021/ja01164a039

InChI:InChI=1/C15H18/c1-10(2)13-8-6-12(4)14-7-5-11(3)9-15(13)14/h5-10H,1-4H3

Upstream product

• 523-47-7 cadinene 
• 489-84-9 7-isopropyl-1,4-dimethyl-azulene 
• 55732-91-7 7,10-epoxy-1,3,5-bisabolatrien-11-ol 
• 54274-73-6 (1S,4R,4aS)-1,2,3,4,4a,5,6,7-octahydro-4-methyl-7-methylene-1-(1-methylethyl)naphthalene 
• 5937-11-1 (-)-α-Cadinol 
• 152694-88-7 [1aR-(1a-alpha,7alpha,7a-beta,7b-alpha)]-1a,2,3,5,6,7,7a,7b-octahydro-1,1,4,7-tetramethyl-1H-cycloprop[e]azulene 
• 14087-01-5 (-)-isozingiberene 
• 1121-05-7 2,3-dimethylcyclopent-2-enone 
• 187737-37-7 propene 
• 76739-27-0 ar-himachalene 

Downstream Products

• 575-43-9 1,6-dimethylnaphthalene 
• 581-42-0 2.6-dimethylnaphthalene 
• 87018-28-8 cadalenequinone mono 2,4-dinitrophenylhydrazone 

Relevant articles and documents

Versatile synthesis of cadalene and iso-cadalene from himachalene mixtures: Evidence and application of unprecedented rearrangements

From a mixture of α-, β- and γ-himachalenes extracted from waste wood of Atlas cedar (Cedrus atlantica), cadalene (1,6-dimethyl-4-isopropylnaphthalene) and iso-cadalene (1,6-dimethyl-3-isopropylnaphthalene) were produced in two steps with up to 71percent ± 5percent yield through the ar-himachalene intermediate using I2 and/or AlCl3 as reagents. The selectivity is shown to sharply depend on the operating conditions: while I2/AlCl3 in dichloromethane promotes the formation of cadalene, the formation of iso-cadalene is favored in the presence of AlCl3 in cyclohexane. The bicyclic aromatic compounds were thus obtained through unique rearrangements involving sequential C–C bond cleavage/formation and hydride transfer processes. In the absence of AlCl3 or I2, dihydrocurcumene was also found to be formed with up to 70percent selectivity. A tentative mechanism is proposed and discussed.

Sesquiterpenoid constituents of the liverwort Marsupella aquatica

Nine new amorphane sesquiterpenoids, (+)-7β-hydroxyamorpha-4,11-diene, (-)-9α-hydroxyamorpha-4,7(11)-diene, (-)-3α-hydroxyamorpha-4,7(11)-diene, (-)-3α-acetoxyamorpha-4,7(11)-diene, (-)-amorpha-4,7(11)-dien-3-one, (+)-2,8-epoxyamorpha-4,7(11)-diene, (+)-5,9-epoxyamorpha-3,7(11)-diene, (-)-2α-hydroxyamorpha-4,7(11)-diene and (-)-2β-acetoxyamorpha-4,7(11)-diene, were isolated from the essential oil of the liverwort Marsupella aquatica, collected near Gaschurn/Montafon, Austria. The isolated compounds and their chemical transformations were investigated using enantioselective GC and extensive spectroscopic studies (HRMS, 1H, 13C and 2D NMR). The absolute configuration of most of the isolated compounds were established by conversions to known compounds. In addition, 1H, and 13C NMR data of (-)-myltayl-4-ene are reported for the first time.

OXIDATION OF AZULENE DERIVATIVES. AUTOXIDATION OF GUAIAZULENE IN A POLAR APROTIC SOLVENT

Autoxidation of guaiazulene at 100 deg C in N,N-dimethylformamide afforded twenty-three separable products including seven known compounds.Most of these new compounds possess highly interesting structures of azulenoquinone, inden-1-one, benzocyclobutadien