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Usage

Uses

Used in Cosmetic and Skincare Industry:
Benzo[a]azulene is used as an active ingredient in cosmetic and skincare products for its anti-inflammatory and skin-soothing properties. It provides calming and soothing effects on the skin, making it suitable for various skin types, including sensitive skin.
Used in Pharmaceutical Industry:
Benzo[a]azulene is used as a key component in the synthesis of various pharmaceuticals and organic compounds due to its unique aromatic structure and reactivity. Its properties make it a valuable compound for developing new drugs and therapeutic agents.

Upstream product

• 623-73-4 diazoacetic acid ethyl ester 
• 86-73-7 9H-fluorene 
• 64-17-5 ethanol 
• 14189-83-4 5-(N-methyl-anilino)-penta-2,4-dienal 
• 141-52-6 sodium ethanolate 
• 95-13-6 1-indene 
• 110190-24-4 4b,10-etheno-benzazulene 
• 860686-65-3 4b.5.6.7.8.9.9a.10-octahydro-benz[a]azulenol-⁽⁶⁾ 
• 118-92-3 anthranilic acid 
• 108011-63-8 2--benzylalkohol 
• 34824-53-8 2-(7'-cyclohepta-1',3',5'-trienyl)benzaldehyde 
• 186581-53-3 diazomethane 
• 18663-27-9 triethyl(9H-fluoren-9-yl)silane 
• 860686-83-5 4b,7,8,9,9a,10-hexahydro-benz[a]azulen-6-one 

Downstream Products

• 111531-45-4 3-Pikryl-1,2-benzazulen 
• 85-01-8 phenanthrene 

Relevant academic research and scientific papers

Reaction of Benzazulene with Dimethyl Acetylenedicarboxylate. Formation of a ?-Bond Fixed Heptalene Derivative

Reaction of benzazulene with dimethyl acetylenedicarboxylate (DMAD) in tetralin at 200 deg C gave a new ?-electron system, dimethyl benzoheptalene-6,7-dicarboxylate and dimethyl indenoazulene-5,6-dicarboxylate.The reaction of a non-fused azulene, 6-isopropyl-1-phenylazulene, gave extremely different results indicating strong effects of the fused benzene ring on the reactivities of azulenes with DMAD.Coupling constants of the protons on the seven-membered ring and variable temperature 1H NMR of the heptalene indicated ?-bond fixation of the molecule.

Rhodium(II)-catalysed Cyclisation of Diazoketones derived from Biphenyl; A New Route to Benzazulenes and Related Systems

Cyclisation of 2-diazoacetylbiphenyl with rhodium(II) acetate or mandelate yields the unstable benzazulen-10(9aH)-one from which benzazulene can be obtained by lithium aluminium hydride reduction; similar reactions with the related diazoketones (2)-(5) yield stable benzobicyclotrienones in high yield.

An Efficient Straightforward Synthesis of Benzazulene

Benzazulene (1) is synthesized in five steps (cf.Scheme 2) starting from commercially available 2-iodobenzyl alcohol (4) and tropylium tetrafluoroborate in an overall yield of 44percent.The key step (cf. also Scheme 1) is the intramolecular Heck reacti

THE ADDITION OF BENZYNE TO AZULENE

The title reaction afforded the Diels-Alder adduct 4b,10-etheno-benzazulene (4), while an analogous reacton involving 5,6-dichloroazulene gave the 6,7- and 7,8-dichloro-derivatives of (4).Treatment of (4) with 3,6-di(pyridin-2-yl)-s-tetrazine yielded b

THE ADDITION OF BENZOCYCLOBUTENYLIDENE TO BENZENE. THE FACILE REARRANGEMENT OF SPIRO(BENZOCYCLOBUTENE-1,7'-CYCLOHEPTA-1',3',5'-TRIENE) TO 9a,10-DIHYDROBENZ(a)AZULENE

Thermal decomposition of the sodium salts of benzocyclobutenone tosylhydrazone and 2-methylbenzocyclobutenone tosylhydrazone in benzene affords 9a,10-dihydrobenz(a)azulene 4 and trans-10-methyl-9a,10-dihydrobenz(a)azulene 3, respectively.A mechanism involving initially the addition of the carbene benzocyclobutenylidene, or its 2-Me derivative, to the benzene ring is postulated.A proposed intermediate in the reaction, spiro(benzocyclobutene-1,7'-cyclohepta-1',3',5'-triene) 12 has been synthesised, and shown to give rise to 4 under the reaction conditions.The rate of rearrangement of 12 -> 4 has been measured, and the activation energy determined: Ea = 125.9 +/- 0.8 kJmol-1 and A = 1.38*1014 sec-1.The mechanism for the rearrangement must involve ring opening of the benzocyclobutene moiety of 12 to give an o-xylylene intermediate which is postulated to possess considerable diradical character.At 71.8 deg C this ring opening is 2.7*106 times faster than the ring opening of the parent benzocyclobutene molecule.The decomposition of the sodium salt of 2-(7'-cyclohepta-1',3',5'-trienyl)benzaldehyde tosylhydrazone has also been investigated, and is shown to yield 4a,10-dihydrobenz(a)azulene, 9,10-dihydrobenz(a)azulene and 8,9-benzotricyclo(5.3.0.02.10)deca-3,5,8-triene.A mechanism involving intramolecular 1,3-dipolar addition of a diazo grouping to a cycloheptatriene Π-bond, followed by decomposition of the resulting pyrazoline intermediate, is proposed.