20669-52-7

Basic information

• Product Name: 3-phenyl-1,2-dihydronaphthalene
• Synonyms: 1,2-Dihydro-3-phenylnaphthalene; 3-Phenyl-1,2-dihydronaphthalene
• CAS NO: 20669-52-7
• Molecular Formula: C₁₆H₁₄
• Molecular Weight: 206.2824
• Mol File: 20669-52-7.mol
• Article Data: 26

Chemical Properties

• Boiling Point: 327.6°C at 760 mmHg
• Flash Point: 159.4°C
• Density: 1.075g/cm³
• Vapor Pressure: 0.000382mmHg at 25°C
• Refractive Index: 1.616
• CAS DataBase Reference: 3-phenyl-1,2-dihydronaphthalene(CAS DataBase Reference)
• NIST Chemistry Reference: 3-phenyl-1,2-dihydronaphthalene(20669-52-7)
• EPA Substance Registry System: 3-phenyl-1,2-dihydronaphthalene(20669-52-7)

Safety Data

• Hazardous Substances Data: 20669-52-7(Hazardous Substances Data)

Upstream product

• 143139-14-4 trifluoromethanesulfonic acid 3,4-dihydronaphthalen-2-yl ester 
• 849943-93-7 3,4-dihydronaphthalen-2-yl 4-methylbenzenesulfonate 
• 98-80-6 phenylboronic acid 
• 591-51-5 phenyllithium 
• 591-50-4 iodobenzene 
• 123994-49-0 3,4-dihydro-1-naphthyl triflate 
• 1078-58-6 diphenylzinc 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 107408-16-2 3-(o-bromophenyl)propanal 
• 1282418-35-2 3-(2-bromophenyl)-1-phenylpropan-1-ol 
• 530-93-8 1,2,3,4-tetrahydronaphthalen-2-one 
• 100-58-3 phenylmagnesium bromide 
• 91388-41-9 (E)-1-formyl-2-(2-methyl-2-phenylethenyl)benzene tosylhydrazone 
• 447-53-0 1,2-Dihydronaphthalene 

Downstream Products

• 7498-87-5 2-phenyl-3,4-dihydro-2H-naphthalen-1-one 
• 881851-79-2 (1S,2R)-2-phenyl-1,2,3,4-tetrahydronaphthalen-1-ol 
• 57653-11-9 1-Hydroxy-2-phenyl-1,4-dihydronaphthalin 
• 40650-73-5 and 2-phenyl-1,4-dihydronaphthalene 
• 612-94-2 2-phenylnaphthalene 
• 62019-39-0 2-phenyl-1,2-dihydronaphthalene 
• 135042-37-4 1,1-Dibrom-1a,2,3,7b-tetrahydro-1a-phenyl-1H-cyclopropanaphthalin 

Relevant articles and documents

Catalytic 1,2-dihydronaphthalene and: E -aryl-diene synthesis via CoIII-Carbene radical and o -quinodimethane intermediates

Catalytic synthesis of substituted 1,2-dihydronaphthalenes via metalloradical activation of o-styryl N-tosyl hydrazones ((E)-2-(prop-1-en-1-yl)benzene-N-tosyl hydrazones) is presented, taking advantage of the intrinsic reactivity of a cobalt(iii)-carbene radical intermediate. The method has been successfully applied to a broad range of substrates with various R1 substituents at the aromatic ring, producing the desired ring products in good to excellent isolated yields for substrates with an R2 = COOEt substituent at the vinylic position (～70-90%). Changing the R2 moiety from an ester to other substituents has a surprisingly large influence on the (isolated) yields. This behaviour is unexpected for a radical rebound ring-closure mechanism, and points to a mechanism proceeding via ortho-quinodimethane (o-QDM) intermediates. Furthermore, substrates with an alkyl substituent on the allylic position reacted to form E-aryl-dienes in excellent yields, rather than the expected 1,2-dihydronaphthalenes. This result, combined with the outcome of supporting DFT calculations, strongly points to the release of reactive o-QDM intermediates from the metal centre in all cases, which either undergo a 6π-cyclisation step to form the 1,2-dihydronaphthalenes, or a [1,7]-hydride shift to produce the E-aryl-dienes. Trapping experiments using TEMPO confirm the involvement of cobalt(iii)-carbene radical intermediates. EPR spectroscopic spin-trapping experiments using phenyl N-tert-butylnitrone (PBN) confirm the radical nature of the catalytic reaction.

Synthesis of multisubstituted cycloalkenes through carbomagnesiation of strained cycloalkynes

An efficient synthetic method of seven- and six-membered cycloalkenes through the generation of strained cycloalkynes and following carbomagnesiation is described. Further bond formations of the resulting cycloalkenylmagnesium intermediates with a wide variety of electrophiles enabled us to prepare diverse cycloalkene derivatives including benzoxepine analogs having a fully substituted alkene structure.

Gold(I)-Catalyzed Intramolecular C(sp3)?H Insertion by Decarbenation of Cycloheptatrienes

A novel synthesis of indanes and dihydronaphtalenes based on the intramolecular insertion into C(sp3)?H bonds of gold(I) carbenes generated by retro-Buchner reaction (decarbenation) has been developed. Deuterium-labeling and kinetic isotope effect experiments, DFT calculations, and generation of the proposed carbene intermediate from a well-characterized gold(I) carbenoid support the involvement of a three-center concerted mechanism for the C(sp3)?H functionalization process.