1154-13-8

Usage

Chemical Class

Polycyclic aromatic hydrocarbons (PAHs)

Explanation

1,1'-Binaphthalene, 1,1',2,2',3,3',4,4'-octahydrobelongs to a group of chemical compounds known as polycyclic aromatic hydrocarbons, which are characterized by their fused aromatic rings.

Explanation

This is an alternative name for the compound, which highlights the presence of a tetramethylene bridge connecting the two naphthalene units.

Explanation

The compound appears as a solid with a color ranging from colorless to light yellow, indicating its relatively low volatility and stability at room temperature.

Explanation

The molecular formula represents the number of carbon (C) and hydrogen (H) atoms present in the compound, which is 22 and 24, respectively.

Explanation

The compound has various applications in the chemical industry, including its use as a chiral auxiliary in organic synthesis, the production of chiral ligands for asymmetric catalysis, and as a stabilizer and antioxidant in the rubber and plastic industries. It is also used as an intermediate in the synthesis of pharmaceuticals and other fine chemicals.

Explanation

It is important to handle 1,1'-Binaphthalene, 1,1',2,2',3,3',4,4'-octahydrowith caution due to its potential carcinogenic properties and toxic effects on both human health and the environment. Proper safety measures should be taken during its production, use, and disposal to minimize risks.

Physical State

Colorless to light yellow solid

Applications

Organic synthesis, chiral auxiliary, chiral ligands for asymmetric catalysis, stabilizer and antioxidant in rubber and plastic industries, intermediate in pharmaceutical synthesis

Potential Hazards

Carcinogenicity, 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 
• 30332-83-3 1-(perfluorophenyl)-2-(1-phenylethylidene)hydrazine 
• 101749-61-5 tri-sec-butylindium 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 69339-77-1 1,2,3-trihydronaphthyl radical 
• 86769-21-3 acetophenone 1,3,4,5,6,7,8-heptafluoro-2-naphthylhydrazone 
• 39588-43-7 1,2,3-Benzothiadiazol-6-carbonsaeure-methylester 

Relevant academic research and scientific papers

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).

HOMOLYTIC PYRIDYLETHYLATION OF CYCLOHEXANE AND TETRALIN

The homolytic pyridylethylation of cyclohexene and tetraline with 2-vinylpyridine under conditions of peroxide and thermal initiation was investigated.In addition to the main reaction products, i.e., cycloalkylethylpyridines (1 : 1 adducts), compounds indicating rearrangement of the radicals with H migration were also isolated and identified.

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).

Investigations on Benzothiirene

Thermolysis and photolysis of 1,2,3-benzothiadiazole 10c furnish the products 11c - 15c. 13C-labelling experiments demonstrate that an intermediate benzothiirene 1c is not formed.Isotopomeric reaction products are due to H-shifts.Electron withdrawing ester groups in 6-position enable the ring closure to the substituted benzothiirenes 1d, e on the photochemical but not on the thermal route.A proof is given by an extensive study of the disulfides 14d, e, 14d', e', and 14d'', e'', generated in the thermolysis, photolysis and by an independent procedure.The results are based on 13C and 1H NMR measurements.Unequivocal signal correlations were made by deuterations and heteronuclear double resonances.

Partially Fluorinated Heterocyclic Compounds. Part 18. Formation of Fischer Indole Products from Acetophenone 1,3,4,5,6,7,8-Heptafluoro-2-naphthylhydrazone and Acetophenone Pentafluorophenylhydrazone. The Surprising Loss of o-Fluorine

Acetophenone 1,3,4,5,6,7,8-heptafluoro-2-naphthylhydrazone (2) and acetophenone pentafluorophenylhydrazone (3) react in tetralin at reflux temperature to give among the products 4,5,6,7,8,9-hexafluoro-2-phenylbenzindole (6) and 4,5,6,7-tetrafluoro-2-ph

The Thermal Decomposition of N,O-Diacyl-N-t-butylhydroxylamines

Several N,O-diacyl-N-t-butylhydroxylamines and O-acyl-N-t-butylhydroxylamines were prepared, and their thermal decompositions were studied.The thermal decompositions of N,O-diacyl-N-t-butylhydroxylamines in tetralin gave substituted N-t-butylbenzamides, carbocyclic acids 1,1'-bitetrayl, and 1,2-dihydronaphtalene as the major products, together with small amounts of carbon dioxide, t-butylamine, and benzanilides.In the thermal decompositions of O-acyl-N-t-butylhydroxylamines, the products were t-butylamine, carbocyclic acids, substituted N-t-butylbenzamides, 1,1'-bi tetrayl, and 1,2-dihydronaphtalene.