1-Ethynyl-4-methoxybenzene

Base Information

• Chemical Name: 1-Ethynyl-4-methoxybenzene
• CAS No.: 768-60-5
• Molecular Formula: C9H8O
• Molecular Weight: 132.162
• Hs Code.: 29093090
• European Community (EC) Number: 640-179-8
• NSC Number: 71091
• DSSTox Substance ID: DTXSID20290800
• Nikkaji Number: J401.609B
• Wikidata: Q69758029
• ChEMBL ID: CHEMBL232552
• Mol file: 768-60-5.mol

Synonyms:4-Ethynylanisole;768-60-5;1-Ethynyl-4-methoxybenzene;4-Methoxyphenylacetylene;1-eth-1-ynyl-4-methoxybenzene;4'-Methoxyphenyl acetylene;Benzene, 1-ethynyl-4-methoxy-;1-ethynyl-4-methoxy-benzene;4-ethynyl anisole;p-methoxyphenylacetylene;MFCD00168815;4-methoxyphenyl acetylene;4'-Methoxyphenylacetylene;4-ethynyl-1-methoxybenzene;p-ethynylanisole;4-ethynyl-anisole;NSC71091;p-Methoxyphenylethyne;4-methoxyphenylethyne;4-methoxy-phenylacetylene;4-Ethynylanisole, 97%;4'-methoxy phenylacetylene;4-methoxy-phenyl-acetylene;1-methoxy-4-ethynylbenzene;4-methoxy-1-ethynyl benzene;1-(4-methoxyphenyl)acetylene;4-CH3O-C6H4-CCH;SCHEMBL187127;1-Ethynyl-4-methoxybenzene #;CHEMBL232552;DTXSID20290800;CHEBI:194788;BBL104009;NSC 71091;NSC-71091;STL557821;AKOS005146078;CS-W004104;PS-4187;AC-19401;BP-12812;SY013463;A9736;AM20060729;E0603;FT-0618957;EN300-83248;Q-102460;F0001-1960;Z1080385508

Chemical Property of 1-Ethynyl-4-methoxybenzene

Chemical Property:

• Appearance/Colour: pale yellow oil
• Melting Point: 28-29 °C(lit.)
• Refractive Index: n20/D 1.563(lit.)
• Boiling Point: 194.8 °C at 760 mmHg
• Flash Point: 63.5 °C
• PSA: 9.23000
• Density: 1.01 g/cm³
• LogP: 1.67650
• Storage Temp.: Store Cold
• Sensitive.: Light Sensitive
• Solubility.: Acetontrile (Slightly), Chloroform (Slightly)
• Water Solubility.: Insoluble in water. Soluble in chloroform, acetone, dichloromethane, and methanol.
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 132.057514874
• Heavy Atom Count: 10
• Complexity: 134

Purity/Quality:

99% ^*data from raw suppliers

4-Methoxyphenylacetylene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xn
• Hazard Codes: Xn,F
• Statements: 22
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)C#C
• Uses: Intermediate in the synthesis of histamine H3-receptor antagonists. Also utilized to prepare its luminescent copper complex Intermediates of Liquid Crystals 1,3-dipolar cycloaddition of acceptor-cyclopropylmethylsilanes affords functionalized cyclopentenes in good yields.1 4-Ethynylanisole was used in the synthesis of photo luminescent 1,2-dihydrophosphinines via a [4 + 2] cycloaddition. Along with an arylboronic acid and sodium azide in a copper-catalyzed, three-component synthesis of trisubstituted 1,2,4-triazoles. In a study of a gold (III)-catalyzed hydroamination of alkynes leading to N-vinylindoles3.

Technology Process of 1-Ethynyl-4-methoxybenzene

There total 106 articles about 1-Ethynyl-4-methoxybenzene 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%

(4-methoxyphenylethynyl)trimethylsilane (3989-14-8) → 4-methoxyphenylacetylen (768-60-5)

Guidance literature:

With methanol; potassium carbonate; In tetrahydrofuran; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1016/j.tet.2010.11.012

Reference yield: 96.0%

4-(4-methoxyphenyl)-2-methyl-3-butyn-2-ol (84384-30-5) → 4-methoxyphenylacetylen (768-60-5)

Guidance literature:

With potassium phosphate; In dimethyl sulfoxide; at 80 ℃; for 24h;

DOI:10.1016/j.tet.2005.07.099

Reference yield: 94.0%

dimethyl 1-(1-diazo-2-oxopropyl)phosphonate (90965-06-3) + 4-methoxy-benzaldehyde (123-11-5) → 4-methoxyphenylacetylen (768-60-5)

Guidance literature:

With potassium carbonate; In methanol; at 20 ℃; for 12h; Inert atmosphere;

DOI:10.1002/chem.201100609

upstream raw materials:

3-(4-methoxyphenyl)propynoic acid

4-(2-bromo-vinyl)-anisole

sodium methylate

1-(1-chloroethenyl)-4-methoxybenzene

Downstream raw materials:

N,N-diethyl-3-(4-methoxyphenyl)prop-2-yn-1-amine

5-(4-methoxyphenyl)-3-phenylisoxazole

(4-methoxy-phenyl)-glyoxal-2-(4-nitro-phenylhydrazone)

1-bromo-2-(4-methoxyphenyl)acetylene

Refernces

Mechanism of formation of [(PMe₃)₃Rh(-C≡C-R)₂(H)] via C-H oxidative addition: Isomerization, alkyne exchange, and hydride replacement

10.1021/om010685r

The study investigates the mechanism of formation of mer,trans-[(PMe3)3Rh(-CtC-R)2H] complexes from [(PMe3)4Rh(Me)] and terminal alkynes. The research explores the initial steps of the reaction, which involve the elimination of methane and the formation of a trigonal bipyramidal complex, followed by an oxidative addition reaction with a second equivalent of alkyne to yield the kinetic product fac-[(PMe3)3Rh(-CtC-R)2H]. This fac isomer is unstable and isomerizes to the thermodynamic product mer,trans-[(PMe3)3Rh(-CtC-R)2H]. The study also examines alkyne exchange reactions and the configurational stability of the formed complexes. Chemicals used include [(PMe3)4Rh(Me)], terminal alkynes such as ethynyltrimethylsilane (TMSA), p-methoxyphenylethyne, and p-cyanophenylethyne, which serve as reactants in the synthesis and investigation of the reaction mechanisms. The purpose of these chemicals is to understand the formation and behavior of rhodium complexes with potential applications in areas such as molecular wires, polymeric systems, catalysts, liquid crystals, and nonlinear optics. Density functional theory (DFT) studies were also conducted to support the experimental observations.