4780-79-4

Usage

Uses

1. Used in Chemical Research:
1-Naphthalenemethanol is used as a research compound for investigating various chemical reactions and processes. Its role in the UV photooxidation of 1-methylnaphthalene in the presence of dry or humid air has been a subject of study, contributing to the understanding of chemical behavior under different environmental conditions.
2. Used in Pharmaceutical Industry:
As an intermediate in the synthesis of various pharmaceutical compounds, 1-Naphthalenemethanol plays a crucial role in the development of new drugs and medications. Its unique chemical properties make it a valuable component in the creation of novel therapeutic agents.
3. Used in Environmental Science:
1-Naphthalenemethanol's involvement in the study of UV photooxidation processes helps researchers understand the impact of air quality on chemical reactions. This knowledge can be applied to develop strategies for mitigating pollution and improving air quality.
4. Used in Material Science:
The unique chemical properties of 1-Naphthalenemethanol make it a potential candidate for the development of new materials with specific characteristics. Its application in material science can lead to the creation of innovative products with improved performance and functionality.

Synthesis Reference(s)

Tetrahedron Letters, 34, p. 4893, 1993 DOI: 10.1016/S0040-4039(00)74039-1

InChI:InChI=1/C11H10O/c12-8-10-6-3-5-9-4-1-2-7-11(9)10/h1-7,12H,8H2

Upstream product

• 2459-24-7 methyl 1-naphthoate 
• 2243-81-4 1-naphthylcarboxamide 
• 50-00-0 formaldehyd 
• 703-55-9 1-naphthylmagnesiumbromide 
• 51042-38-7 1,3-di(naphthalen-1-yl)propan-2-one 
• 5292-43-3 bromoacetic acid tert-butyl ester 
• 66-77-3 1-naphthaldehyde 
• 138556-70-4 di(1-naphthylmethyl) peroxydicarbonate 
• 56-23-5 tetrachloromethane 
• 64-17-5 ethanol 
• 26870-27-9 1-(naphthalen-1-yl)-2-phenoxyethan-1-one 
• 91-20-3 naphthalene 
• 60-29-7 diethyl ether 
• 71-43-2 benzene 

Downstream Products

• 143659-23-8 naphthalen-1-ylmethyl 2-(4-methoxyphenyl)acetate 
• 143659-24-9 1-Naphthylmethyl 3-methoxyphenylacetate 
• 36707-32-1 1-(1-naphthyl)-2-phenylethane 
• 172154-18-6 naphthalen-1-ylmethyl (4-nitrophenyl) carbonate 
• 86-53-3 1-Cyanonaphthalene 
• 375385-38-9 4-(2-iodo-1-naphthalenemethyl)cyclohex-2-en-1-one 
• 375385-34-5 6-(2-iodo-1-naphthylmethyl)-3-isobutoxycyclohex-2-en-1-one 
• 66-77-3 1-naphthaldehyde 
• 32280-54-9 N-(naphthalen-1-ylmethyl)benzamide 
• 4730-77-2 naphthalen-1-ylmethylphosphonic acid 
• 1071907-22-6 (naphthalen-1-ylmethyl)(phenyl)phosphinic acid 
• 1264675-72-0 C₂₇H₃₂N₂OSi 
• 65426-83-7 p-nitrophenyl 1-naphthoate 

Relevant academic research and scientific papers

The lewis base-catalyzed silylation of alcohols-a mechanistic analysis

Reaction rates for the base-catalyzed silylation of primary, secondary, and tertiary alcohols depend strongly on the choice of solvent and catalyst. The reactions are significantly faster in Lewis basic solvents such as dimethylformamide (DMF) compared with those in chloroform or dichloromethane (DCM). In DMF as the solvent, the reaction half-lives for the conversion of structurally similar primary, secondary, and tertiary alcohols vary in the ratio 404345:20232:1. The effects of added Lewis base catalysts such as 4-N,N-dimethylaminopyridine (DMAP) or 4-pyrrolidinopyridine (PPY) are much larger in apolar solvents than in DMF. The presence of an auxiliary base such as triethylamine is required in order to drive the reaction to full conversion.

Leaving Group Effects on the Selectivity of the Silylation of Alcohols: The Reactivity-Selectivity Principle Revisited

TBS protection of primary alcohol naphthalen-1-ylmethanol (4a) and secondary alcohol 1-(naphthalen-1-yl)ethanol (4b) has been studied under various reaction conditions. The primary/secondary selectivity is largest in the comparatively slow Lewis base catalyzed silylation in apolar solvents and systematically lower in DMF. Lowest selectivities (and fastest reaction rates) are found for TBS triflate 1b, where only minor effects of solvent polarity or Lewis base catalysis can be observed. (Chemical Equation Presented).

Chemoselective Cleavage of Acylsulfonamides and Sulfonamides by Aluminum Halides

The chemoselective cleavage of C-N bonds of amides, sulfonamides, and acylsulfonamides by aluminum halides is described. AlCl3and AlI3display complementary reactivities toward N-alkyl and N-acyl moieties. N-Alkylacylsulfonamides, sec

Supported Iridium Catalyst for Clean Transfer Hydrogenation of Aldehydes and Ketones using Methanol as Hydrogen Source

The use of methanol as abundant and low-toxic hydrogen source under mild and clean conditions is promising for the development of safe and sustainable reduction processes, but remains a daunting challenge. This work presents a recyclable ZnO-supported Ir

Silver-Catalyzed Hydroboration of C-X (X = C, O, N) Multiple Bonds

AgSbF6 was developed as an effective catalyst for the hydroboration of various unsaturated functionalities (nitriles, alkenes, and aldehydes). This atom-economic chemoselective protocol works effectively under low catalyst loading, base- A nd solvent-free moderate conditions. Importantly, this process shows excellent functional group tolerance and compatibility with structurally and electronically diverse substrates (>50 examples). Mechanistic investigations revealed that the reaction proceeds via a radical pathway. Further, the obtained N,N-diborylamines were showcased to be useful precursors for amide synthesis.

Hydroboration Reaction and Mechanism of Carboxylic Acids using NaNH2(BH3)2, a Hydroboration Reagent with Reducing Capability between NaBH4and LiAlH4

Hydroboration reactions of carboxylic acids using sodium aminodiboranate (NaNH2[BH3]2, NaADBH) to form primary alcohols were systematically investigated, and the reduction mechanism was elucidated experimentally and computationally. The transfer of hydride ions from B atoms to C atoms, the key step in the mechanism, was theoretically illustrated and supported by experimental results. The intermediates of NH2B2H5, PhCH= CHCOOBH2NH2BH3-, PhCH= CHCH2OBO, and the byproducts of BH4-, NH2BH2, and NH2BH3- were identified and characterized by 11B and 1H NMR. The reducing capacity of NaADBH was found between that of NaBH4 and LiAlH4. We have thus found that NaADBH is a promising reducing agent for hydroboration because of its stability and easy handling. These reactions exhibit excellent yields and good selectivity, therefore providing alternative synthetic approaches for the conversion of carboxylic acids to primary alcohols with a wide range of functional group tolerance.

Membrane transport inspired hydrolysis of non-activated esters at near physiological pH

A positively charged micelle loaded with substrates was transported selectively to the reaction site (cathode) to promote the proximity and localization of the reactants (ester and hydroxide). The guided vehicular delivery coupled with electrolysis allows the hydrolysis of non-activated esters at near physiological pH with significant yields along with recyclability.

Sodium Aminodiboranate, a New Reagent for Chemoselective Reduction of Aldehydes and Ketones to Alcohols

Sodium aminodiboranate (NaNH 2(BH 3) 2, NaADBH) is a new member of the old borane family, which exhibits superior performance in chemoselective reduction. Experimental results show that NaADBH can rapidly reduce aldehydes and ketones to the corresponding alcohols in high efficiency and selectivity under mild conditions. There are little steric and electronic effects on this reduction.

A Bifunctional Copper Catalyst Enables Ester Reduction with H2: Expanding the Reactivity Space of Nucleophilic Copper Hydrides

Employing a bifunctional catalyst based on a copper(I)/NHC complex and a guanidine organocatalyst, catalytic ester reductions to alcohols with H2 as terminal reducing agent are facilitated. The approach taken here enables the simultaneous activation of esters through hydrogen bonding and formation of nucleophilic copper(I) hydrides from H2, resulting in a catalytic hydride transfer to esters. The reduction step is further facilitated by a proton shuttle mediated by the guanidinium subunit. This bifunctional approach to ester reductions for the first time shifts the reactivity of generally considered "soft"copper(I) hydrides to previously unreactive "hard"ester electrophiles and paves the way for a replacement of stoichiometric reducing agents by a catalyst and H2.

Efficient and chemoselective hydrogenation of aldehydes catalyzed by well-defined PN3-pincer manganese(ii) catalyst precursors: An application in furfural conversion

Well-defined and air-stable PN3-pincer manganese(ii) complexes were synthesized and used for the hydrogenation of aldehydes into alcohols under mild conditions using MeOH as a solvent. This protocol is applicable for a wide range of aldehydes containing various functional groups. Importantly, α,β-unsaturated aldehydes, including ynals, are hydrogenated with the CC double bond/CC triple bond intact. Our methodology was demonstrated for the conversion of biomass derived feedstocks such as furfural and 5-formylfurfural to furfuryl alcohol and 5-(hydroxymethyl)furfuryl alcohol respectively.