1,2,4-Trimethoxybenzene

Base Information

• Chemical Name: 1,2,4-Trimethoxybenzene
• CAS No.: 135-77-3
• Molecular Formula: C9H12O3
• Molecular Weight: 168.192
• Hs Code.: 29093090
• European Community (EC) Number: 205-219-7
• UNII: 3KU3WD07SS
• DSSTox Substance ID: DTXSID5035163
• Nikkaji Number: J141.476C
• Wikidata: Q27257439
• Pharos Ligand ID: MBD5NWWHW9P8
• ChEMBL ID: CHEMBL1668605
• Mol file: 135-77-3.mol

Synonyms:1,2,4-trimethoxybenzene

Chemical Property of 1,2,4-Trimethoxybenzene

Chemical Property:

• Appearance/Colour: clear light yellow to yellow-brown liquid
• Vapor Pressure: 0.0413mmHg at 25°C
• Melting Point: 19 - 21oC
• Refractive Index: n20/D 1.533(lit.)
• Boiling Point: 247 °C at 760 mmHg
• Flash Point: 77.9 °C
• PSA: 27.69000
• Density: 1.041 g/cm³
• LogP: 1.71240
• Storage Temp.: Store below +30°C.
• Solubility.: Chloroform, Ethyl Acetate
• Water Solubility.: Not miscible in water.
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 168.078644241
• Heavy Atom Count: 12
• Complexity: 127

Purity/Quality:

99% ^*data from raw suppliers

1,2,4-Trimethoxybenzene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=CC(=C(C=C1)OC)OC
• Uses: 1,2,4-Trimethoxybenzene is used as a reagent in the synthesis of barbigerone derivatives which can be used as antiproliferative and antiangiogenesis agents. Also used as a reagent in the synthesis of Malvone A (M161525) which is a phytoalexin found in Malva sylvestris.

Technology Process of 1,2,4-Trimethoxybenzene

There total 35 articles about 1,2,4-Trimethoxybenzene 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: 99.4%

1,2,4-triacetoxybenzene (613-03-6) + dimethyl sulfate (77-78-1) → 1,2,4-trimethoxy-benzene (135-77-3)

Guidance literature:

1,2,4-triacetoxybenzene; With methanol; potassium hydroxide; at 40 ℃; for 0.133333h; Inert atmosphere;

dimethyl sulfate; With potassium carbonate; at 60 ℃; for 0.5h; pH=8.5; Reagent/catalyst; Inert atmosphere;

Reference yield: 99.0%

1,2,4-Trihydroxybenzene (533-73-3) + dimethyl sulfate (77-78-1) → 1,2,4-trimethoxy-benzene (135-77-3)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 20 ℃; for 12h;

DOI:10.1016/j.bmcl.2008.06.065

Reference yield: 98.0%

2,4-dibromoanisole (21702-84-1) + sodium methylate (124-41-4) → 1,2,4-trimethoxy-benzene (135-77-3)

Guidance literature:

With methanol; Methyl formate; copper(l) chloride; at 115 ℃; for 2h; Autoclave; Green chemistry;

DOI:10.1007/s11164-014-1917-x

upstream raw materials:

2',4'-dihydroxy-4-acetophenone

1-(2,4-dihydroxyphenyl)-2-(4-methoxyphenyl)ethanone

asaronic acid

1,2,4-Trihydroxybenzene

Downstream raw materials:

1-(2,4,5-trimethoxy-phenyl)-dodecan-1-one

5-oxo-5-(2,4,5-trimethoxy-phenyl)-valeric acid

2-hydroxy-4,5-dimethoxybenzophenone

(phenyl)(2,4,5-trimethoxyphenyl)methanone

Refernces

• 1、 v. Hemmelmayr. "-". . p. 4. Retrieved 1914.
• 2、 -. "Synthetic method of medical intermediate 1,2,4-trimethoxybenzene". Paragraph 0008-0029. . Retrieved 2018/07/30.
• 3、 Gadge, Sandip T.,Mishra, Ashish,Gajengi, Aravind L.,Shahi, Nileshkumar V.,Bhanage, Bhalchandra M.. "Magnesium oxide as a heterogeneous and recyclable base for the N-methylation of indole and O-methylation of phenol using dimethyl carbonate as a green methylating agent". . p. 50271 - 50276. Retrieved 2014/12/10.