10394-57-7

Basic information

• Product Name: 9-BUTYLPHENANTHRENE
• Synonyms: 9-BUTYLPHENANTHRENE;9-n-Butylphenanthrene
• CAS NO: 10394-57-7
• Molecular Formula: C₁₈H₁₈
• Molecular Weight: 234.34
• Mol File: 10394-57-7.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 9-BUTYLPHENANTHRENE(CAS DataBase Reference)
• NIST Chemistry Reference: 9-BUTYLPHENANTHRENE(10394-57-7)
• EPA Substance Registry System: 9-BUTYLPHENANTHRENE(10394-57-7)

Safety Data

• Hazardous Substances Data: 10394-57-7(Hazardous Substances Data)

Upstream product

• 109-65-9 1-bromo-butane 
• 71112-64-6 9-phenanthrylmagnesium bromide 
• 109-72-8 n-butyllithium 
• 60-29-7 diethyl ether 
• 947-72-8 9-chlorophenanthrene 
• 2311-91-3 monoperoxyphthalic acid 
• 16703-29-0 9-butyl-1,2,3,4,5,6,7,8-octahydrophenanthrene 
• 501680-77-9 1-biphenyl-2-yl-2-methoxy-ethanone 
• 693-04-9 butyl magnesium bromide 
• 102950-20-9 9-butyl-1,2,3,4-tetrahydro-phenanthrene 
• 95870-55-6 p-Toluolsulfonsaeure-<9-butyl-fluorenyl-(9)-methylester> 
• 217-59-4 triphenylene 
• 585-08-0 1a,9b-dihydrophenanthro<9,10-b>oxirene 
• 13029-09-9 2,2'-dibromobiphenyl 

Relevant articles and documents

Iron-Catalyzed C(sp2)–C(sp3) Cross-Coupling of Alkyl Grignard Reagents with Polyaromatic Tosylates

The iron-catalyzed cross-coupling of polyaromatic tosylates with alkyl Grignard reagents controlled by O-coordinating ligand is reported. The reaction operates under very mild, operationally practical conditions to furnish alkylated polyaromatics that are a common motif in a wide range of electronic-material, pharmaceutical and high-performance fluid applications. The challenging C(sp2)–C(sp3) cross-coupling products are obtained in good to excellent yields obviating the problems associated with β-hydride elimination. For the first time the coupling of polyaromatic tosylates can be achieved in the presence of sensitive carboxylic acid derived functional groups. Mechanistic studies suggest that the reaction selectivity can be correlated with the reduction potential of polyaromatic hydrocarbons. The method represents a rare example of sustainable C–O bond alkylation of polyarenes at room temperature.

Nickel-Catalyzed C(sp2)?C(sp3) Kumada Cross-Coupling of Aryl Tosylates with Alkyl Grignard Reagents

Aryl tosylates are an attractive class of electrophiles for cross-coupling reactions due to ease of synthesis, low price, and the employment of C?O electrophiles, however, the reactivity of aryl tosylates is low. Herein, we report the Ni-catalyzed C(sp2)?C(sp3) Kumada cross-coupling of aryl tosylates with primary and secondary alkyl Grignard reagents. The method delivers valuable alkyl arenes by cross-coupling with challenging alkyl organometallics possessing β-hydrogens that are prone to β-hydride elimination and homo-coupling. The reaction is catalyzed by an air- and moisture stable-Ni(II) precatalyst. A broad range of electronically-varied aryl tosylates, including bis-tosylates, underwent this transformation, and many examples are suitable at mild room temperature conditions. The combination of Ar?X cross-coupling with the facile Ar?OH activation/cross-coupling strategy permits for orthogonal cross-coupling with challenging alkyl organometallics. Furthermore, we demonstrate that the method operates with TON reaching 2000, which is one of the highest turnovers observed to date in Ni-catalyzed cross-couplings. (Figure presented.).

Cobalt?NHC Catalyzed C(sp2)?C(sp3) and C(sp2)?C(sp2) Kumada Cross-Coupling of Aryl Tosylates with Alkyl and Aryl Grignard Reagents

The first cobalt-catalyzed cross-coupling of aryl tosylates with alkyl and aryl Grignard reagents is reported. The catalytic system uses CoF3 and NHCs (NHC=N-heterocyclic carbene) as ancillary ligands. The reaction proceeds via highly selective C?O bond functionalization, leading to the corresponding products in up to 98 % yield. The employment of alkyl Grignard reagents allows to achieve a rare C(sp2)?C(sp3) cross-coupling of C?O electrophiles, circumventing isomerization and β-hydride elimination problems. The use of aryl Grignards leads to the formation of biaryls. The C?O cross-coupling sets the stage for a sequential cross-coupling by exploiting the orthogonal selectivity of the catalytic system.

Palladium-Catalyzed Sequential Vinyl C–H Activation/Dual Decarboxylation: Regioselective Synthesis of Phenanthrenes and Cyclohepta[1,2,3-de]naphthalenes

The application of a C(vinyl), C(aryl)-palladacycle from vinyl-containing substrates is challenging due to the interference of a reactive double bond in palladium catalysis. This Letter describes a [4 + 2] or [4 + 3] cyclization based on a C(vinyl), C(aryl)-palladacycle by employing α-oxocarboxylic acids as the insertion units under a palladium/air system. The reaction proceeded through the key vinyl C–H activation and dual decarboxylation sequence, forming phenanthrenes and cyclohepta[1,2,3-de]naphthalenes regioselectively in good yields. The synthetic versatility of this protocol is highlighted by the gram-scale synthesis and synthesizing functional material molecule.

Murahashi Cross-Coupling at ?78 °C: A One-Pot Procedure for Sequential C?C/C?C, C?C/C?N, and C?C/C?S Cross-Coupling of Bromo-Chloro-Arenes

The coupling of organolithium reagents, including strongly hindered examples, at cryogenic temperatures (as low as ?78 °C) has been achieved with high-reactivity Pd-NHC catalysts. A temperature-dependent chemoselectivity trigger has been developed for the selective coupling of aryl bromides in the presence of chlorides. Building on this, a one-pot, sequential coupling strategy is presented for the rapid construction of advanced building blocks. Importantly, one-shot addition of alkyllithium compounds to Pd cross-coupling reactions has been achieved, eliminating the need for slow addition by syringe pump.

Nickel-Catalyzed Reductive Cross-Coupling of Aryl Triflates and Nonaflates with Alkyl Iodides

A nickel-catalyzed cross-electrophile coupling of aryl triflates and nonaflates with alkyl iodides using manganese(0) as a reductant is described. The method is applicable to the reductive alkylation of various aryl sulfonates, including o -borylaryl triflate, which enabled efficient construction of diverse alkylated arenes under mild conditions.

Synthesis of Functionalized Phenanthrenes via Regioselective Oxidative Radical Cyclization

The majority of Sn-mediated cyclizations are reductive and, thus, cannot give a fully conjugated product. This is a limitation in the application of Sn-mediated radical cascades for the preparation of fully conjugated molecules. In this work, we report an oxidatively terminated Bu3Sn-mediated cyclization of an alkyne where AIBN, the commonly used initiator, takes on a new function as an oxidative agent. Sn-mediated radical transformation of biphenyl aryl acetylenes into functionalized phenanthrenyl stannanes can be initiated via two potentially equilibrating vinyl radicals, one of which can be trapped by the fast 6-endoclosure at the biphenyl moiety in good to excellent yields. The efficient preparation of Sn-substituted phenanthrenes opens access to convenient building blocks for the construction of larger polyaromatics.

Expedient synthesis of phenanthrenes via In(III)-catalyzed 6-exo-dig cycloisomerization

This paper documents the first example of In(III)-catalyzed selective 6-exo-dig hydroarylation of o-propargylbiaryls and their subsequent double-bond migration to obtain functionalized phenanthrenes. Electron-rich biaryl substrates undergo hydroarylation

Gold-catalyzed efficient tandem assembly of terminal alkynes and arynes: Synthesis of alkynylated biphenyl derivatives

Gold catalysts have been found to catalyze the tandem assembly of arynes and terminal alkynes efficiently in the presence of CuI under mild reaction conditions to provide useful alkynylated biphenyl derivatives. The Royal Society of Chemistry.

Site-specific preparation of 2-carboalkoxy-4-substituted naphthalenes and 9-alkylphenanthrenes and evidence for an allene intermediate in the novel base-catalyzed cyclization of 2-alkynylbiphenyls

A site-specific preparation of 2-carboalkoxy-4-substituted naphthalenes and 9-alkylphenanthrenes is described. The successful cyclization of an allene intermediate provides supportive evidence for the previously proposed mechanism.