40888-18-4

Usage

Physical state

Colorless to pale yellow liquid

Molecular weight

210.27 g/mol

Usage

Reagent in organic synthesis, pharmaceutical intermediate, building block in the synthesis of pharmaceuticals and agrochemicals, reagent in chemical reactions (Sonogashira coupling and Click chemistry), production of fragrances, flavors, and other fine chemicals

Value

Versatile and valuable compound in organic chemistry with a wide range of applications

InChI:InChI=1/C15H14O/c1-15(2,16)11-10-13-8-5-7-12-6-3-4-9-14(12)13/h3-9,16H,1-2H3

Upstream product

• 90-14-2 1-Iodonaphthalene 
• 115-19-5 2-methyl-but-3-yn-2-ol 
• 90-11-9 1-Bromonaphthalene 
• 1139705-28-4 naphthalene-1-yl 1H-imidazole-1-sulfonate 
• 40888-12-8 1-[3-(1-Ethoxy-ethoxy)-3-methyl-but-1-ynyl]-naphthalene 

Downstream Products

• 15727-65-8 1-ethynylnaphthalene 
• 1360703-67-8 (Z)-3-benzoyl-5,5-dimethyl-4-(naphthalen-1-ylmethylene)oxazolidin-2-one 
• 1367363-62-9 C₂₉H₂₆O₂ 
• 41790-87-8 (E)-1,4-di-(1-naphthyl)butenyne 

Relevant academic research and scientific papers

Synthesis of a deep cavity calix[4]arene by fourfold Sonogashira cross-coupling reaction and selective fluorescent recognition toward p-nitrophenol

A new tetranaphthyl-calix[4]arene (C4N4) was synthesized by a fourfold Sonogashira cross-coupling reaction, and exhibited high affinity and selectivity for p-nitrophenol (3c) by fluorescence spectroscopy. The NMR, AFM, IR, MALDI-TOF mass spectroscopy, and computational calculations revealed the formation of a host-guest complex driven by π-π stacking interactions.

Bimetal Cooperatively Catalyzed Arylalkynylation of Alkynylsilanes

An unprecedented Pd/Rh cooperatively catalyzed arylalkynylation of alkynylsilanes was developed to merge an alkynylidene moiety with benzosilacycle. These silaarenes possess a particular aggregation-induced emission behavior. Mechanistic investigations demonstrate that the relay trimetallic transmetalation plays a pivotal role in governing this transformation.

Ru(ii)-catalyzed allenylation and sequential annulation of: N -tosylbenzamides with propargyl alcohols

We hereby report Ru(ii)-catalyzed C(sp2)-H allenylation of N-tosylbenzamides to access multi-substituted allenylamides. Furthermore, the allenylamides were converted to the corresponding isoquinolone derivatives via base mediated annulation. The current protocol features low catalyst loading, mild reaction conditions, high functional group compatibility and desired scalability. The unique functionality of the afforded allenes allowed further transformations to expand the practicality of the protocol. This journal is

Sonogashira-Hagihara and Buchwald-Hartwig cross-coupling reactions with sydnone and sydnone imine derived catalysts

Seven different palladium complexes of sydnones and sydnone imines and a co-catalyst system consisting of lithium sydnone-4-carboxylate and Pd(PPh3)4 catalyzed Sonogashira-Hagihara reactions between (hetero)- aromatic bromides and 2-methylbut-3-yn-2-ol (52 examples, up to 100% yield). The co-catalyst system and a sydnone Pd complex were also tested in Buchwald-Hartwig reactions (9 examples, up to 100% yield). (Equation Presented).

Cleavage of C–C and C–O Bonds to Form C–C Bonds: Direct Cross-Coupling between Acetylenic Alcohols and Benzylic Carbonates

A palladium-catalyzed cross-coupling reaction between C(sp) and C(sp3) centers was achieved in excellent yields via C–C bond cleavage and C–O bond cleavage. This procedure uses relatively stable acetylenic alcohols as reactants instead of unsta

Anionic N-heterocyclic carbenes derived from sydnone imines such as molsidomine. Trapping reactions with selenium, palladium, and gold

The sydnone imines Molsidomine and 5-(benzoylimino)-3-(2-methoxyphenyl)-1,2,3-oxadiazolium-2-ide gave anionic N-heterocyclic carbenes on deprotonation at C4 which were trapped as methylated selenium adducts, gold complexes (X-ray analysis) as well as palladium complexes (X-ray analysis). The 13C NMR resonance frequencies of the carbene carbon atom are extremely shifted upfield and appear at δ = 142.1 ppm (Molsidomine carbene) and δ = 159.8 ppm (sydnone imine carbene). The Pd complexes were applied as catalysts in Suzuki-Miyaura and Sonogashira-Hagihara cross-coupling reactions.

Efficient Microwave-Assisted Synthesis of Sonogashira-Coupled Perylene Monoimide Derivatives: Impact of Electron-Donating Groups on Optoelectronic Properties

An efficient microwave-assisted Sonogashira-coupling protocol for the synthesis of peri-functionalized perylene monoimide dye derivatives was developed. This method was found to be significantly faster than the conventional coupling method and provided pr

A through bond energy transfer based ratiometric probe for fluorescent imaging of Sn2+ ions in living cells

A 4-(naphthalen-1-ylethynyl) aniline appended rhodamine based fluorescent chemosensor 'NAP-RD' is synthesized which undergoes through bond energy transfer in the presence of Sn2+ ions in mixed aqueous media. NAP-RD is an excellent colorimetric

Palladium-catalyzed oxidative deacetonative coupling of 4-aryl-2-methyl-3-butyn-2-ols with H-phosphonates

An efficient and generally applicable protocol for palladium-catalyzed oxidative deacetonative coupling of 4-aryl-2-methyl-3-butyn-2-ols with dialkyl H-phosphonates has been developed. This methodology provides a new and practical route to alkynylphosphonates using the inexpensive 4-aryl-2-methyl-3-butyn-2-ols as the alkyne sources. This reaction could also be performed with aryl bromides, 2-methyl-3-butyne-2-ol and dialkyl H-phosphonates using the cheap 2-methyl-3-butyne-2-ol as an alkyne source. This journal is

Practical synthesis of aryl-2-methyl-3-butyn-2-ols from aryl bromides via conventional and decarboxylative copper-free Sonogashira coupling reactions

Two efficient protocols for the palladium-catalyzed synthesis of aryl-2-methyl-3-butyn-2-ols from aryl bromides in the absence of copper were developed. A simple catalytic system consisting of Pd(OAc)2 and P(p-tol)3 using DBU as the base and THF as the solvent was found to be highly effective for the coupling reaction of 2-methyl-3-butyn-2-ol (4) with a wide range of aryl bromides in good to excellent yields. Analogously, the synthesis of aryl-2-methyl-3-butyn-2-ols was performed also through the decarboxylative coupling reaction of 4-hydroxy-4-methyl-2-pentynoic acid with aryl bromides, using a catalyst containing Pd(OAc)2 in combination with SPhos or XPhos in the presence of tetra-n-butylammonium fluoride (TBAF) as the base and THF as the solvent. Therefore, new efficient approaches to the synthesis of terminal acetylenes from widely available aryl bromides rather than expensive iodides and using 4 or propiolic acid rather than TMS-acetylene as inexpensive alkyne sources are described.