6844-18-4

Usage

Appearance

White crystalline solid

Common uses

Synthesis of pharmaceuticals and organic compounds, fragrance ingredient in perfumes, starting material for the production of other chemicals, building block for the synthesis of pharmaceuticals and other organic compounds, production of various drugs, reagent in organic chemistry reactions

Safety

Relatively safe when handled and used according to proper precautions and guidelines

Upstream product

• 5720-07-0 4-methoxyphenylboronic acid 
• 66-77-3 1-naphthaldehyde 
• 18052-80-7 1-naphthyltrimethylsilane 
• 123-11-5 4-methoxy-benzaldehyde 
• 100-66-3 methoxybenzene 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 86-55-5 1-naphthalenecarboxylic acid 
• 39070-92-3 (4-methoxyphenyl)(naphthalen-1-yl)methanone 
• 703-55-9 1-naphthylmagnesiumbromide 

Downstream Products

• 861068-51-1 (+/-)-phthalic acid mono-[(4-methoxy-phenyl)-(naphthyl-⁽¹⁾)-methyl ester] 
• 32891-88-6 (4-methoxyphenyl)(naphth-1-yl)methane 
• 677761-68-1 (4-methoxyphenyl)(2-methyl-4-hydroxyphenyl)(naphth-1-yl)methane 
• 586949-84-0 (4-methoxyphenyl)(3-methyl-4-hydroxyphenyl)(naphth-1-yl)methane 
• 144867-03-8 1-[methoxy(4-methoxypehnyl)methyl]naphthalene 
• 1456695-48-9 C₂₄H₂₀OS 
• 1456695-49-0 C₂₄H₂₁NO 
• 1456695-59-2 C₂₄H₂₁NO 
• 1456695-50-3 C₂₅H₂₃NO 
• 1456695-60-5 C₂₅H₂₃NO 
• 1456695-51-4 C₂₆H₂₅NO 

Relevant academic research and scientific papers

Nickel-Catalyzed Addition of Aryl Bromides to Aldehydes to Form Hindered Secondary Alcohols

Transition-metal-catalyzed addition of aryl halides across carbonyls remains poorly developed, especially for aliphatic aldehydes and hindered substrate combinations. We report here that simple nickel complexes of bipyridine and PyBox can catalyze the addition of aryl halides to both aromatic and aliphatic aldehydes using zinc metal as the reducing agent. This convenient approach tolerates acidic functional groups that are not compatible with Grignard reactions, yet sterically hindered substrates still couple in high yield (33 examples, 70% average yield). Mechanistic studies show that an arylnickel, and not an arylzinc, adds efficiently to cyclohexanecarboxaldehyde, but only in the presence of a Lewis acid co-catalyst (ZnBr2).

The cooperative effect of Lewis pairs in the Friedel-Crafts hydroxyalkylation reaction: A simple and effective route for the synthesis of (±)-carbinoxamine

An efficient C-C bond formation strategy between aromatic/heteroaromatic π-nucleophiles and Lewis acid activated aldehydes is described. This aromatic electrophilic substitution reaction of arenes or heteroarenes is facilitated by Lewis acid AlBr3. Aromatic rings with electron donating substituents are excellent nucleophilic counterparts in this reaction, generating carbinols in excellent yields (61-94%). The formation of triarylmethanes is also witnessed in the case of certain reactive aldehydes and aromatic π-nucleophiles through reactive carbocation formation. The formation of triarylmethane is reduced to a greater extent via retardation of the second π-nucleophile addition through a Lewis base, for example, pyridine, coordination with an aluminium alkoxide intermediate. Various aliphatic aldehydes also underwent Friedel-Crafts type hydroxyalkylation and generated the expected carbinols in moderate yields (41-53%) in the presence of AlBr3. This protocol has been successfully applied to the synthesize of the (±)-carbinoxamine, a therapeutically important histamine H1 antagonist, in a one-pot manner.

Synthetic approach towards trisubstituted methanes and a chiral tertiary α-hydroxyaldehyde, a possible intermediate for tetrasubstituted methanes

A series of trisubstituted methanes containing aryl and heteroaryl rings, as well as a sulfur spacer between the central methano-carbon and benzene ring, is reported. In an approach towards asymmetric tetrasubstituted methane with high enantioselectivity,

Phosphazene base-promoted functionalization of aryltrimethylsilanes

The activation of Ar-Si bonds in aryltrimethylsilane was investigated using a catalytic amount of t-Bu-P4 base and selective functionalizations of aryltrimethylsilanes in the absence of strong electron withdrawing groups on the aromatic rings were accomplished. The Royal Society of Chemistry 2006.

Use of cheaper metal than Rh, CHCl3-free Pd catalyst, in 1,2-addition of aromatic aldehydes with arylboronic acids

Pd(OAc)2-(±)-tol-BINAP-catalyzed arylation reaction of aromatic aldehydes with arylboronic acids in the absence of CHCl3 is described.

Diaryl naphthyl methanes a novel class of anti-implantation agents

Diaryl naphthyl methanes and the corresponding 1, 2, 3, 4- and 5, 6, 7, 8-tetrahydro naphthyl methane derivatives have been synthesized as novel estrogen receptor binding ligands. The secondary and tertiary amino alkoxy derivatives of diaryl naphthyl and

Rhodium-catalysed aryl transfer to aldehydes: Counterion effects with nitrogen containing ligands

Cationic rhodium complexes of certain nitrogen-containing ligands exhibit excellent activity in the addition of arylboronic acids to aldehydes. The counterion had a notable effect with the weakly coordinating carborane anion affording a highly active catalyst.

Research on antibacterial and antifungal agents. 16. Synthesis and antifungal activities of 1-[α-(1-naphthyl)benzyl]imidazole derivatives and related 2-naphthyl isomers

Some 1-arylmethylimidazoles bearing a naphthyl group at the α position of benzyl moiety have been synthesized and tested as antifungal agents against Candida albicans and Candida spp. Such derivatives resemble bifonazole and naftifine, two important antim

Laser flash photolysis studies of the formation and reactivities of phenyl(naphthyl)methyl carbocations generated from phosphonium salt precursors

The photolysis of several substituted phenyl(naphthyl)methyl triphenylphosphonium chlorides has been examined using a combination of laser flash photolysis experiments and product studies.Both carbocation and radical intermediates have been characterized in the transient experiments, with the relative yields depending strongly on the solvent.For example, in alcohols, acetonitrile, or aqueous solvents cation formation predominates while acetonitrile/dioxane mixtures (5-10percent) are required for the observation of radicals.Quantum yields for cation formation vary from 0.79 in methanol to 0.093 in 1:4 acetonitrile/dioxane, as measured by product studies and transient experiments, respectively.The addition of perchlorate salts leads to dramatic enhancements in the cation lifetimes; the effects are particularly pronounced for acetonitrile/dioxane mixtures where the cation yields also increase by factors of 3-4.In this case the effects are attributed primarily to replacement of chloride by perchlorate in the initial ion pairs.The combined data from both solvent and perchlorate salt effects on the cation lifetimes and yields suggest that the excited state of the phosphonium salt cleaves homolytically, followed by electron transfer within the initial radical/triphenylphosphine radical cation pair to generate carbocation, as opposed to direct heterolytic cleavage.The cation yields also indicate the back reaction to regenerate starting material, as well as product formation within the initial geminate cage, occur in some solvents.The effects of solvent and added perchlorate salts on the rate constants for reaction with nucleophiles have been examined.For example, rate constants that vary by an order of magnetitude have been measured for quenching by azide ion in various aqueous acetonitrile and trifluoroethanol mixtures.