613-59-2

Basic information

• Product Name: 2-BENZYLNAPHTHALENE
• Synonyms: 2-(Phenylmethyl)naphthalene;Naphthalene, 2-benzyl-;naphthalene,2-(phenylmethyl)-;2-BENZYLNAPHTHALENE;2-Naphtylphenylmethane
• CAS NO: 613-59-2
• Molecular Formula: C₁₇H₁₄
• Molecular Weight: 218.29
• Mol File: 613-59-2.mol

Chemical Properties

• Melting Point: 58°C
• Boiling Point: 293.99°C (rough estimate)
• Flash Point: 163.8°C
• Appearance: /
• Density: 1.1760
• Vapor Pressure: 9.15E-05mmHg at 25°C
• Refractive Index: 1.5566 (estimate)
• CAS DataBase Reference: 2-BENZYLNAPHTHALENE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-BENZYLNAPHTHALENE(613-59-2)
• EPA Substance Registry System: 2-BENZYLNAPHTHALENE(613-59-2)

Safety Data

• Hazardous Substances Data: 613-59-2(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2-BENZYLNAPHTHALENE is used as a building block for the synthesis of various organic compounds due to its polycyclic aromatic structure and reactivity.
Used in Fragrance Industry:
2-BENZYLNAPHTHALENE is used as a fragrance ingredient in the production of perfumes and cosmetics, adding to their aromatic profiles.
Used in Candle Manufacturing:
2-BENZYLNAPHTHALENE is used in the manufacturing of candles and other scented products to provide a pleasant aroma.
However, it is crucial to handle 2-BENZYLNAPHTHALENE with care, as it is considered toxic and can cause skin and eye irritation.

InChI:InChI=1/C17H14/c1-2-6-14(7-3-1)12-15-10-11-16-8-4-5-9-17(16)13-15/h1-11,13H,12H2

Upstream product

• 644-13-3 C₆H₅COC₁₀H₇ 
• 2657-20-7 phenyl(5,6,7,8-tetrahydronaphthalen-2-yl)methanone 
• 27019-11-0 3-benzyl-1,2-dihydronaphthalene 
• 91-20-3 naphthalene 
• 100-44-7 benzyl chloride 
• 5435-44-9 (E)-3-Ureido-but-2-enoic acid ethyl ester 
• 100-51-6 benzyl alcohol 
• 54538-01-1 2-[2]naphthylmethyl-aniline 
• 6261-31-0 2-benzylidene-1-tetralol 
• 129113-13-9 2E-benzylidene-1,2,3,4-tetrahydronaphthalene 
• 71-43-2 benzene 
• 167561-52-6 <2-Methylcinnamoyl(phenyl)methylene>triphenylphosphorane 
• 28867-76-7 benzaldehyde benzylidenehydrazone 
• 286-85-1 1H-cyclopropa[b]naphthalene 

Downstream Products

• 859197-14-1 (6-benzyl-[2]naphthyl)-phenyl ketone 
• 859197-29-8 1-(6-benzyl-[2]naphthyl)-ethanone 
• 123239-63-4 2-benzyl-[1]naphthoic acid 
• 205-12-9 benzo[c]fluorene 
• 644-13-3 C₆H₅COC₁₀H₇ 
• 65-85-0 benzoic acid 
• 33440-68-5 2-benzyl-1,4-naphthoquinone 
• 1020537-23-8 naphthalen-2-yl(phenyl)methyl acetate 
• 35060-38-9 (R)-naphthalen-2-yl(phenyl)methanol 

Relevant articles and documents

Nickel-Catalyzed Electrochemical C(sp3)?C(sp2) Cross-Coupling Reactions of Benzyl Trifluoroborate and Organic Halides**

Reported here is the redox neutral electrochemical C(sp2)?C(sp3) cross-coupling reaction of bench-stable aryl halides or β-bromostyrene (electrophiles) and benzylic trifluoroborates (nucleophiles) using nonprecious, bench-stable NiCl2?glyme/polypyridine catalysts in an undivided cell configuration under ambient conditions. The broad reaction scope and good yields of the Ni-catalyzed electrochemical coupling reactions were confirmed by 50 examples of aryl/β-styrenyl chloride/bromide and benzylic trifluoroborates. Potential applications were demonstrated by electrosynthesis and late-stage functionalization of pharmaceuticals and natural amino acid modification, and three reactions were run on gram-scale in a flow-cell electrolyzer. The electrochemical C?C cross-coupling reactions proceed through an unconventional radical transmetalation mechanism. This method is highly productive and expected to find wide-spread applications in organic synthesis.

Desulfurative Ni-Catalyzed Reductive Cross-Coupling of Benzyl Mercaptans/Mercaptoacetates with Aryl Halides

The C-S activation and sulfur removal from native thiols is challenging, which limits their application as feedstock materials in organic synthesis despite their natural abundance. Herein, we introduce a per-/polyfluoroaryl moiety, which serves as a redox-active scaffold, into sp3-hybridized thiols to activate the C-S bond. Using a Ni catalyst with MgBr2 as an additive, the S group can be removed to yield an aliphatic radical that can react with an aryl halide in a reductive cross-coupling.

Arylketones as Aryl Donors in Palladium-Catalyzed Suzuki-Miyaura Couplings

Herein, we report the arylation, alkylation, and alkenylation of aryl ketones via a palladium-catalyzed Suzuki-Miyaura cross-coupling reaction. The use of the pyridine-oxazoline ligand is the key to the cleavage of the unstrained C-C bond. The late-stage arylation of aryl ketones derived from drugs and natural products demonstrated the synthetic utility of this protocol.

Palladium-Catalyzed Cross-Coupling of Superbase-Generated C(sp3) Nucleophiles

A range of methods has been investigated recently for the arylation of weakly acidic C(sp3)-H bonds, primarily exploiting directed metalation with a transition metal catalyst or radical formation via hydrogen atom transfer. In this work, a classical base-mediated approach is taken, exploiting the ability of organometallic superbases to metalate very weakly acidic (pKa> 40) C-H bonds. Conditions are developed with eithern-BuLi/diamine orn-BuLi/KOtBu superbases to enable metalation to occur with high selectivity. Organolithium nucleophiles can be directly used in cross-coupling, or organozincs can be formed to enable reactions with functional group-dense organohalides.

Selective Conversion of Benzylic Phosphates into Diarylmethanes Through Al(OTf)3-Catalyzed Friedel–Crafts-Type Benzylation

Al(OTf)3 was identified as a high-performance catalyst for Friedel–Crafts-type benzylation using benzylic phosphates as electrophiles. The reaction proceeded even with 0.2 mol-% of the catalyst. A series of diarylmethanes (21 examples) was obtained in moderate to high yield. The catalyst showed unique chemoselectivity, preferentially converting the benzylic phosphate motif, even with a benzylic acetate group existed in the same molecule.

Alumina grafted SBA-15 sustainable bifunctional catalysts for direct cross-coupling of benzylic alcohols to diarylmethanes

AlSBA-15 catalysts possessing Br?nsted acid and Lewis acid-base bifunctionalities catalyze the direct arylation of benzyl alcohols to diarylmethanes with an 85% product yield through C-O bond activation. 2 and 4wt%AlSBA-15 catalysts have been synthesised by adopting a simple and efficient post-synthetic metal implantation route. The synthesised catalysts were characterized using XRD, N2 adsorption and desorption, 27Al MAS NMR, XPS, HR-TEM, NH3 and CO2-temperature-programmed desorption (TPD) and pyridine-transmission-FTIR spectroscopy techniques to confirm the existence of Br?nsted acid and Lewis acid-base bifunctionalities. Through various control experiments, it is verified that Br?nsted acid sites activate the benzyl alcohol and Lewis base sites interact with phenylboronic acid concurrently to accomplish the coupling reaction. In the recyclability study, 4wt%AlSBA-15 preserves its activity and stability up to 5 cycles. The 4wt%AlSBA-15 catalyst unlike homogeneous catalysts does not require additives, long reaction time and expensive metals.

Super electron donor-mediated reductive desulfurization reactions

The desulfurization of thioacetals and thioethers by a pyridine-derived electron donor is described. This methodology provides efficient access to the reduced products in high yields and does not require the use of transition-metals, elemental alkali-metals, or hydrogen atom donors.

Palladium-Catalyzed Hiyama Coupling of Benzylic Ammonium Salts via C-N Bond Cleavage

The first palladium-catalyzed Hiyama cross-coupling of arylsilanes with benzyltrimethylammonium salts is reported. The reaction proceeds smoothly to facilitate C(sp2)-C(sp3) bond formation via cleavage of the C-N bond and provides a useful approach to various diarylmethanes with a broad substrate scope and excellent functional group tolerance in good to excellent yields.

Cross coupling of benzylammonium salts with boronic acids using a well-defined N-heterocyclic carbene-palladium(ii) precatalyst

N-heterocyclic carbene-palladium(ii)-catalyzed cross-coupling of benzylammonium salts with arylboronic acids for the synthesis of diarylmethane derivatives via C-N bond activation has been developed. Notably, in the presence of the easily prepared and bench-stable Pd-PEPPSI precatalyst, the Csp3-N bond activation of the benzylammonium salt even proceeded smoothly in isopropanol at room temperature.

Construction of Di(hetero)arylmethanes Through Pd-Catalyzed Direct Dehydroxylative Cross-Coupling of Benzylic Alcohols and Aryl Boronic Acids Mediated by Sulfuryl Fluoride (SO2F2)

A practical Pd-catalyzed direct dehydroxylative coupling of (hetero)benzylic alcohols with (hetero)arylboronic acids for the constructions of di(hetero)arylmethane derivatives under SO2F2 was described. This new method provided a strategically distinct approach to di(hetero)arylmethane derivatives from readily available and abundant benzylic alcohols under mild condition.