Lithium phenylacetylide

Base Information

• Chemical Name: Lithium phenylacetylide
• CAS No.: 4440-01-1
• Molecular Formula: C8H5Li
• Molecular Weight: 108.069
• Hs Code.: 2902909090
• European Community (EC) Number: 684-516-7
• DSSTox Substance ID: DTXSID20392474
• Mol file: 4440-01-1.mol

Synonyms:lithium phenylacetylide

Chemical Property of Lithium phenylacetylide

Chemical Property:

• Flash Point: 1 °F
• PSA: 0.00000
• Density: 0.91 g/mL at 25 °C
• LogP: 1.54490
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 108.05512859
• Heavy Atom Count: 9
• Complexity: 103

Purity/Quality:

98%,99%, ^*data from raw suppliers

LithiumPhenylacetylide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F; C
• Hazard Codes: F,C
• Statements: 11-14-19-20/21/22-34-40-37
• Safety Statements: 16-26-27-36/37/39-45

MSDS Files:

Useful:

• Canonical SMILES: [Li+].[C-]#CC1=CC=CC=C1
• Uses: Lithium Phenylacetylide is used in organic reaction to add the ethynylbenzene group to a compound.

Technology Process of Lithium phenylacetylide

There total 9 articles about Lithium phenylacetylide 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%

phenylacetylene (536-74-3) → lithium phenylacetylide (4440-01-1)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h; Inert atmosphere;

DOI:10.1002/anie.201101948

Reference yield: 65.0%

lithium bis(trimethylsilyl)phosphanide-tetrahydrofuran (1/2) (59610-41-2) + phenylacetylene (536-74-3) → bis(trimethylsilyl)phosphine (15573-39-4) + lithium phenylacetylide (4440-01-1)

Guidance literature:

In toluene; for 12h; Ambient temperature;

Reference yield: 56.0%

2-(2-Bromo-thiophen-3-ylmethyl)-3-[2-oxo-2-phenyl-eth-(E)-ylidene]-2,3-dihydro-isoindol-1-one → 3-[2-Oxo-2-phenyl-eth-(E)-ylidene]-2-thiophen-3-ylmethyl-2,3-dihydro-isoindol-1-one + lithium phenylacetylide (4440-01-1)

Guidance literature:

With palladium diacetate; triethylamine; triphenylphosphine; In acetonitrile; for 144h; Yield given; Heating;

DOI:10.1016/0040-4039(96)01738-8

upstream raw materials:

phenyllithium

phenylacetylene

n-butyllithium

lithium bis(trimethylsilyl)phosphanide-tetrahydrofuran (1/2)

Downstream raw materials:

5-phenylisoxazole

(E)-1,5-diphenyl-3-(phenylethynyl)pent-1-en-4-yn-3-ol

10-hydroxy-10-(phenylethynyl)anthracen-9(10H)-one

9,10-bis(phenylethynyl)phenanthrene-9,10-diol

Refernces

• 1、 Marchetti, Fabio,Zacchini, Stefano,Zanotti, Valerio. "Carbon monoxide-isocyanide coupling promoted by acetylide addition to a diiron complex". . p. 8101 - 8104. Retrieved 2015.
• 2、 Bai, Ruopeng,Zhang, Guanghui,Yi, Hong,Huang, Zhiliang,Qi, Xiaotian,Liu, Chao,Miller, Jeffrey T.,Kropf, A. Jeremy,Bunel, Emilio E.,Lan, Yu,Lei, Aiwen. "Cu(II)-Cu(I) synergistic cooperation to lead the alkyne C-H activation". . p. 16760 - 16763. Retrieved 2014.
• 3、 Buter, Jeffrey,Doze, Anna M.,Feringa, Ben L.,Mondal, Anirban,Visser, Paco. "Pd-catalyzed sp-sp3cross-coupling of benzyl bromides using lithium acetylides". supporting information. p. 7529 - 7532. Retrieved 2021/08/05.
• 4、 Lee, Jae In. "Novel Synthesis of Aurones by 2-PyONa-catalyzed Regioselective Cyclization of o-(Alkynon-1-yl)phenols". . p. 679 - 682. Retrieved 2018/04/05.