1-Ethynyl-4-methoxy-2-methylbenzene

Base Information

• Chemical Name: 1-Ethynyl-4-methoxy-2-methylbenzene
• CAS No.: 74331-69-4
• Molecular Formula: C10H10 O
• Molecular Weight: 146.189
• Hs Code.: 2909309090
• European Community (EC) Number: 627-373-8
• DSSTox Substance ID: DTXSID70584120
• Nikkaji Number: J2.700.759G
• Wikidata: Q72477802
• Mol file: 74331-69-4.mol

Synonyms:1-Ethynyl-4-methoxy-2-methylbenzene;74331-69-4;Benzene,1-ethynyl-4-methoxy-2-methyl-;SCHEMBL987451;DTXSID70584120;IETBNYUYILAKFK-UHFFFAOYSA-N;AKOS010651629;AS-81932;1-Ethynyl-4-methoxy-2-methylbenzene, 97%;CS-0266219;G73611;EN300-1250140;A838094;A1-00963

Chemical Property of 1-Ethynyl-4-methoxy-2-methylbenzene

Chemical Property:

• Vapor Pressure: 0.149mmHg at 25°C
• Melting Point: 30-34 ºC
• Refractive Index: 1.525
• Boiling Point: 222.7°C at 760 mmHg
• Flash Point: 94 ºC
• PSA: 9.23000
• Density: 1g/cm³
• LogP: 1.98490
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 146.073164938
• Heavy Atom Count: 11
• Complexity: 165

Purity/Quality:

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

1-Ethynyl-4-methoxy-2-methylbenzene 97% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36-43
• Safety Statements: 26-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C=CC(=C1)OC)C#C
• Uses: 1-Ethynyl-4-methoxy-2-methylbenzene may be used in the preparation of 5-chloro-3-[(4-methoxy-2-methylphenyl)ethynyl]pyridin-2-amine.

Technology Process of 1-Ethynyl-4-methoxy-2-methylbenzene

There total 7 articles about 1-Ethynyl-4-methoxy-2-methylbenzene 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: 71.0%

(4-methoxy-2-methylphenylethynyl)trimethylsilane → 1-ethynyl-4-methoxy-2-methylbenzene (74331-69-4)

Guidance literature:

With triethylamine trihydrochloride; In tetrahydrofuran; at 35 ℃; for 140h;

DOI:10.1039/c6cc07313a

Reference yield: 17.6%

3-methoxy-6-ethynylbenzyl bromide (82064-55-9) + 8-bromo-2-methyl-1-octen-6-yn-3-one ethylene ketal (82064-58-2) → 2,2-dimethyl-3-<3-(4-ethynylanisyl)>propane (89414-54-0) + 1,2-bis<3-(4-ethynylanisyl)>ethane + 1-ethynyl-4-methoxy-2-methylbenzene (74331-69-4) + 9-<3-(4-ethynylanisyl)>-2-methyl-1-nonen-6-yn-3-one ethylene ketal (82064-62-8)

Guidance literature:

With tert.-butyl lithium; In tetrahydrofuran; pentane; -78 deg C to room temperature;

DOI:10.1021/jo00183a018

Reference yield:

4-bromo-3-methylanisole (27060-75-9) → 1-ethynyl-4-methoxy-2-methylbenzene (74331-69-4)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine; copper(l) iodide; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / tetrahydrofuran / 6 h / 65 °C / Inert atmosphere

2: triethylammonium dihydrofluoride / tetrahydrofuran / 48 h / 35 °C / Inert atmosphere

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; copper(l) iodide; triethylammonium dihydrofluoride; triethylamine; In tetrahydrofuran; 1: |Sonogashira Cross-Coupling;

DOI:10.1039/c4ob01143k

upstream raw materials:

1-(4-Methoxy-2-methylphenyl)vinyl chloride

3-methoxy-6-ethynylbenzyl bromide

8-bromo-2-methyl-1-octen-6-yn-3-one ethylene ketal

1-(4-methoxy-2-methylphenyl)ethanone

Downstream raw materials:

1-(3,3-difluoroprop-1-ynyl)-4-methoxy-2-methylbenzene

N-(2,6-dimethylphenyl)-2-((4-methoxy-2-methylphenyl)ethynylthio)-5-nitrobenzamide

Refernces

• 1、 Frawley, Andrew T.,Pal, Robert,Parker, David. "Very bright, enantiopure europium(III) complexes allow time-gated chiral contrast imaging". . p. 13349 - 13352. Retrieved 2016/11/18.
• 2、 Beshai, Mira,Dhudshia, Bhartesh,Mills, Ryan,Thadani, Avinash N.. "Terminal alkynes from aldehydes via dehydrohalogenation of (Z)-1-iodo-1-alkenes with TBAF". supporting information; experimental part. p. 6794 - 6796. Retrieved 2009/04/07.