CID 6101206

Base Information

• Chemical Name: CID 6101206
• CAS No.: 13146-23-1
• Molecular Formula: C8H5 Cu
• Molecular Weight: 164.674
• Hs Code.: 2902909090
• DSSTox Substance ID: DTXSID40927207
• Mol file: 13146-23-1.mol

Synonyms:13146-23-1;Copper (I) phenylacetylide;DTXSID40927207;SFLVZUJLUPAJNE-UHFFFAOYSA-N;Copper(1+) 2-phenylethyn-1-ide

Chemical Property of CID 6101206

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 0.00000
• Density: g/cm³
• LogP: 1.54240
• Sensitive.: Air & Moisture Sensitive
• Water Solubility.: Soluble in acetone and acetonitrile. Insoluble in water
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 163.968722
• Heavy Atom Count: 9
• Complexity: 98.5

Purity/Quality:

98%Min ^*data from raw suppliers

Copper(I) phenylacetylide, min. 97% ^*data from reagent suppliers

Safty Information:

• Statements: 20/21/22
• Safety Statements: 22-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: [C-]#CC1=CC=CC=C1.[Cu+]
• Uses: Copper(I) phenylacetylide participates in efficient coupling with a range of aryl iodides and bromides to give substituted tolanes?which, if possessing an?ortho?amino or hydroxy group, can be thermolyzed to yield 2-phenylbenzofurans, -indoles, and -furo[3,2-b]pyridines.

Technology Process of CID 6101206

There total 48 articles about CID 6101206 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: 97.2%

copper (12775-96-1,15158-11-9,15721-63-8,16941-75-6,17493-86-6,19498-52-3,20499-83-6,20499-84-7,20499-85-8,20499-86-9,20573-10-8,20573-11-9,21595-51-7,21595-52-8,22206-52-6,26445-28-3,28959-95-7,37362-93-9,39417-05-5,54603-16-6,54603-23-5,54603-32-6,54603-40-6,54603-48-4,54603-81-5,54603-89-3,56316-56-4,95985-91-4,122297-32-9,7440-50-8) + phenylacetylene (536-74-3) → copper(I) phenylacetylide (13146-23-1)

Guidance literature:

With tetraethylammonium bromide; In acetonitrile; byproducts: H2; Electrolysis; electrolysis conducted at room temp., controlled potential -2.4V, electrolyte soln.: 0.76 M PhC2H and 0.12 Et4NBr in CH3CN, pptn.; ppt. filtered, washed with hot CH3CN, dried (room temp., under N2);

Reference yield: 97.0%

copper (12775-96-1,15158-11-9,15721-63-8,16941-75-6,17493-86-6,19498-52-3,20499-83-6,20499-84-7,20499-85-8,20499-86-9,20573-10-8,20573-11-9,21595-51-7,21595-52-8,22206-52-6,26445-28-3,28959-95-7,37362-93-9,39417-05-5,54603-16-6,54603-23-5,54603-32-6,54603-40-6,54603-48-4,54603-81-5,54603-89-3,56316-56-4,95985-91-4,122297-32-9,7440-50-8) + phenylacetylene (536-74-3) → copper(I) phenylacetylenide (13146-23-1)

Guidance literature:

With Et₄N(CH₃C₆H₄SO₃); In acetonitrile; at 20 ℃; for 4h; Reagent/catalyst; Electrochemical reaction;

DOI:10.1039/c9ra06782e

Reference yield: 96.0%

tetrahydrofuran (109-99-9,24979-97-3,77392-70-2) + bis(tetrahydrofuran)ytterbium tris(phenylethynyl)cuprate + methyl iodide (74-88-4) → 1-Phenylprop-1-yne (673-32-5) + copper(I) phenylacetylenide (13146-23-1) + YbI2(thf)4

Guidance literature:

at 20 ℃; for 3h; Schlenk technique;

DOI:10.1134/S1070363214110206

upstream raw materials:

phenylacetylene

acetophenone oxime benzenesulfonate

benzophenone O-tosyloxime

bromostyrene

Downstream raw materials:

7t-phenyl-(6rH)-4-oxa-1-aza-bicyclo[4.2.0]octan-8-one

2-phenylfuro<3,2-b>pyridine

1,5-diphenyl-penta-1,4-diyn-3-one

1-Phenyl-3-methyl-4-penten-1-yne

Refernces

• 1、 Kumar, Rajesh,Tuck, Dennis G.. "AN EFFICIENT ELECTROCHEMICAL SYNTHESIS OF PHENYLETHYNYLCOPPER(I), C6H5CCCu". . p. C47 - C48. Retrieved 1985.
• 2、 Dai, Jingwen,Li, Zili,Wang, Taisheng,Bai, Ruke. "A highly stable and versatile heterobifunctional fluoroalkylation reagent for preparation of fluorinated organic compounds". . p. 4382 - 4386. Retrieved 2016.
• 3、 Li, Gang,Cao, Yi-Xuan,Luo, Chen-Guang,Su, Yi-Ming,Li, Yan,Lan, Quan,Wang, Xi-Sheng. "Copper-Catalyzed Decarboxylative Atom Transfer Radical Addition of Iododifluoroacetate to Alkynyl Carboxylic Acids". . p. 4806 - 4809. Retrieved 2016.
• 4、 Wang, Zijing,Zheng, Tingting,Sun, Hongjian,Li, Xiaoyan,Fuhr, Olaf,Fenske, Dieter. "Sonogashira reactions of alkyl halides catalyzed by NHC [CNN] pincer nickel(II) complexes". . p. 11465 - 11470. Retrieved 2018.
• 5、 Nishihara, Yasushi,Takemura, Miwa,Mori, Atsunori,Osakada, Kohtaro. "Reaction of alkynylsilanes with CuCl in polar solvents leading to alkynyl group transfer from Si to Cu". . p. 282 - 286. Retrieved 2001.
• 6、 Charpe, Vaibhav Pramod,Das, Deb Kumar,Hwang, Kuo Chu,Hwu, Jih Ru,Lin, Chun-Cheng,Pampana, V. K. K.,Sagadevan, Arunachalam. "Oxy-sulfonylation of terminal alkynesviaC-S coupling enabled by copper photoredox catalysis". supporting information. p. 3569 - 3574. Retrieved 2021/06/06.
• 7、 Guo, Zhonglin,Zhou, Pan,Song, Hongjian,Liu, Yuxiu,Zhang, Jingjing,Li, Yongqiang,Wang, Qingmin. "Design, Synthesis, and Bioactivities of Phthalide and Coumarin Derivatives Based on the Biosynthesis and Structure Simplification of Gossypol". . p. 15123 - 15135. Retrieved 2021/12/27.