2-Ethynylnaphthalene

Base Information

• Chemical Name: 2-Ethynylnaphthalene
• CAS No.: 123333-47-1
• Molecular Formula: C12H8
• Molecular Weight: 152.19
• European Community (EC) Number: 676-241-6
• DSSTox Substance ID: DTXSID50183690
• Nikkaji Number: J325.145D
• Wikidata: Q83054514
• ChEMBL ID: CHEMBL1743361
• Mol file: 123333-47-1.mol

Synonyms:2-ethynylnaphthalene;2-ethynylnaphthalene, 3H-labeled

Chemical Property of 2-Ethynylnaphthalene

Chemical Property:

• XLogP3: 3.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 152.062600255
• Heavy Atom Count: 12
• Complexity: 195

Purity/Quality:

98% ^*data from raw suppliers

NAPHTHYLENE-2-ACETYLENE 95 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C#CC1=CC2=CC=CC=C2C=C1

Technology Process of 2-Ethynylnaphthalene

There total 46 articles about 2-Ethynylnaphthalene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

trimethyl(2-(naphthalen-2-yl)ethynyl)silane (40231-00-3) → 2-ethynylnaphthalene (2949-26-0,123333-47-1)

Guidance literature:

With potassium carbonate; In tetrahydrofuran; methanol; at 0 - 20 ℃; for 12h;

DOI:10.1039/c8cc07380e

Reference yield: 96.4%

2-methyl-4-(naphthalen-2-yl)but-3-yn-2-ol (40888-19-5) → 2-ethynylnaphthalene (2949-26-0,123333-47-1)

Guidance literature:

With potassium hydroxide; In toluene; for 3h; Reflux; Inert atmosphere;

DOI:10.1002/ejoc.201701310

Reference yield: 94.0%

2-(2,2-dibromo-vinyl)-naphthalene (218902-65-9) → 2-ethynylnaphthalene (2949-26-0,123333-47-1)

Guidance literature:

With caesium carbonate; dimethyl sulfoxide; at 115 ℃; for 12h;

DOI:10.1016/j.tetlet.2010.12.071

upstream raw materials:

2-(1-bromo-vinyl)-naphthalene

trimethyl(2-(naphthalen-2-yl)ethynyl)silane

β-Chlor-β-(β-naphthyl)-acrolein

methyl 2-naphthyl ketone

Downstream raw materials:

1‐(2‐naphthyl)‐3‐phenylpropan‐1‐one

1-(4-bromo-phenyl)-3-[2]naphthyl-allene

N,4-dimethyl-N-(naphthalen-2-ylethynyl)benzenesulfonamide

1,4-Di-(2-naphthyl)-1,3-butadien

Refernces

• 1、 Shibuya, Masatoshi,Matsuda, Miki,Yamamoto, Yoshihiko. "1,2-Carbopentafluorophenylation of Alkynes: The Metallomimetic Pull-Push Reactivity of Tris(pentafluorophenyl)borane". . p. 8822 - 8831. Retrieved 2021.
• 2、 Chou, Pi-Tai,Fang, Yu,Jiang, Qingwei,Liu, Fengyi,Liu, Ke,Shang, Congdi,Wang, Gang. "Perylene Bisimide and Naphthyl-Based Molecular Dyads: Hydrogen Bonds Driving Co-planarization and Anomalous Temperature-Response Fluorescence". . p. 8579 - 8585. Retrieved 2020.
• 3、 Wentrup, Curt,Becker, Jürgen,Winter, Hans-Wilhelm. "Falling-solid flash vacuum pyrolysis: An efficient preparation of arylacetylenes". . p. 5702 - 5704. Retrieved 2015.
• 4、 Hyacinth, Marilise,Chruszcz, Maksymilian,Lee, Ki Sung,Sabat, Michal,Gao, Ge,Pu, Lin. "Supramolecular assemblies of chiral propargylic alcohols". . p. 5358 - 5360. Retrieved 2006.
• 5、 Uji, Hirotaka,Ogawa, Junya,Itabashi, Kenji,Imai, Tomoya,Kimura, Shunsaku. "Compartmentalized host spaces accommodating guest aromatic molecules in a chiral way in a helix-peptide-aromatic framework". . p. 12483 - 12486. Retrieved 2018.
• 6、 Benanti, Travis L.,Saejueng, Pranorm,Venkataraman. "Segregated assemblies in bridged electron-rich and electron-poor π-conjugated moieties". . p. 692 - 694. Retrieved 2007.
• 7、 Nakasuji,K. et al.. "-". . p. 3567 - 3576. Retrieved 1970.
• 8、 Zhao, Ming,Kuang, Chunxiang,Yang, Qing,Cheng, Xuezhi. "Cs2CO3-mediated synthesis of terminal alkynes from 1,1-dibromo-1-alkenes". . p. 992 - 994. Retrieved 2011.
• 9、 Kinoshita, Hidenori,Kumaki, Wataru,Miura, Katsukiyo. "Regio- and stereoselective synthesis of bromoalkenes by homolytic hydrobromination of alkynes with hydrogen bromide". supporting information. . Retrieved 2022/03/07.
• 10、 Dengiz, ?a?atay. "Polycyclic aromatic hydrocarbon-substituted push-pull chromophores: An investigation of optoelectronic and nonlinear optical properties using experimental and theoretical approaches". . p. 1375 - 1390. Retrieved 2021/10/26.