1154-13-8

Basic information

• Product Name: 1,1'-Binaphthalene, 1,1',2,2',3,3',4,4'-octahydro-
• CAS NO: 1154-13-8
• Molecular Formula: C20H22
• Molecular Weight: 262.395
• Mol File: 1154-13-8.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: 1,1'-Binaphthalene, 1,1',2,2',3,3',4,4'-octahydro-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1'-Binaphthalene, 1,1',2,2',3,3',4,4'-octahydro-(1154-13-8)
• EPA Substance Registry System: 1,1'-Binaphthalene, 1,1',2,2',3,3',4,4'-octahydro-(1154-13-8)

Safety Data

• Hazardous Substances Data: 1154-13-8(Hazardous Substances Data)

Usage

General Description

1,1'-Binaphthalene, 1,1',2,2',3,3',4,4'-octahydro- is a chemical compound that belongs to the class of polycyclic aromatic hydrocarbons (PAHs). It is also known as tetramethylenenaphthalene, and is a colorless to light yellow solid with a molecular formula of C22H24. 1,1'-Binaphthalene, 1,1',2,2',3,3',4,4'-octahydro- is used in organic synthesis as a chiral auxiliary and in the production of chiral ligands for asymmetric catalysis. It is also used as a stabilizer and antioxidant in the rubber and plastic industries, as well as an intermediate in the synthesis of pharmaceuticals and other fine chemicals. However, it is important to handle this compound with caution, as it is a potential carcinogen and may have toxic effects on human health and the environment.

Upstream product

• 100-69-6 2-vinylpyridine 
• 119-64-2 tetralin 
• 51339-08-3 N-benzoyl-O-benzoyl-N-t-butylhydroxylamine 
• 69339-77-1 1,2,3-trihydronaphthyl radical 
• 30332-83-3 1-(perfluorophenyl)-2-(1-phenylethylidene)hydrazine 
• 101749-61-5 tri-sec-butylindium 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 39588-43-7 1,2,3-Benzothiadiazol-6-carbonsaeure-methylester 
• 86769-21-3 acetophenone 1,3,4,5,6,7,8-heptafluoro-2-naphthylhydrazone 

Relevant articles and documents

Unusual selective α-fission of indium-sec-alkyl bonds in solution

Indium trialkyls possessing an α-branch such as In(Bu-s)3 and In(Pr-i)3 decompose through a-fission to give the corresponding alkyl radical selectively during solution pyrolysis.

PARTIALLY FLUORINATED HETEROCYCLIC COMPOUNDS. PART 24. A PLAUSIBLE MECHANISM FOR THE FORMATION OF THE FISCHER INDOLE PRODUCT FROM ACETOPHENONE 1,3,4,5,6,7,8,-HEPTAFLUORO-2-NAPHTHYLHYDRAZONE IN WHICH o-FLUORINE IS LOST

Acetophenone 1,3,4,5,6,7,8,-heptafluoro-2-naphthylhydrazone (1) reacts in tetralin at reflux to give 4,5,6,7,8,9,-hexafluoro-2-phenylbenzindole (2) as the major product, accompanied by other materials including acetophenone 3,4,5,6,7,8,-hexafluoro-2-naphthylhydrazone (4) which is proposed as the true precursor to the Fischer indole product (2) since it gives (2) under the same conditions.The presence of α-tetralone in the reaction mixture provides the clue to a reductive elimination of F- from (1).

Disproportionation-Recombination Rate Ratios for Hydroaromatic Radicals

Relative rates for radical disproportionation (R. + R'. RH + R'd) and recombination (R. + R'. RR') have been determined in the liquid phase at 150 deg C for a series of reactions involving resonance-stabilized hydroaromatic radicals.Self-reactions were studied for the 1-tetralyl, 1-indanyl, 9,10-dihydro-9-phenanthryl, and 9,10-dihydro-9-anthryl radicals.Four cross-radical reactions involving benzyl, diphenylmethyl, and 1-tetralyl radical as H-atom acceptors were also examined.Rate constant ratios (kd/kr) span the range of 1.34 for the self-reaction of 9,10- dihydro-9-phenanthryl radicals to 0.05 for the self-reaction of 9,10-dihydro-9-anthryl radicals.When disproportionation reaction exothermicity is sufficiently small, -ΔHd -1 (210 kJ mol-1), disproportionation rate constants decrease with decreasing exothermicity.A fit of liquid-phase data yields ln (kd/kr) per H atom = -10.1 - 0.163 ΔHd (kcal mol-1).