Trimethyl orthobenzoate

Base Information

• Chemical Name: Trimethyl orthobenzoate
• CAS No.: 707-07-3
• Molecular Formula: C10H14O3
• Molecular Weight: 182.219
• Hs Code.: 29163100
• European Community (EC) Number: 211-897-5
• NSC Number: 67391
• UNII: 3755490344
• DSSTox Substance ID: DTXSID5061039
• Nikkaji Number: J32.055B
• Wikidata: Q27231270
• Mol file: 707-07-3.mol

Synonyms:Trimethyl orthobenzoate;707-07-3;(Trimethoxymethyl)benzene;Trimethyl orthobeznoate;Benzene, (trimethoxymethyl)-;Methyl orthobenzoate;Trimethylorthobenzoate;trimethoxymethylbenzene;Orthobenzoic acid, trimethyl ester;MFCD00008474;Orthobenzoic Acid Trimethyl Ester;EINECS 211-897-5;NSC 67391;NSC-67391;UNII-3755490344;AI3-11562;trimethoxyphenylmethane;trimethoxytoluene;trimethyl-orthobenzoate;PhC(OMe)3;(Trimethoxymethyl);benzene;Orthobenzoic acid trimethyl;(Trimethoxymethyl)benzene #;NCIOpen2_000040;SCHEMBL487231;Trimethyl orthobenzoate, 98%;AMY404;DTXSID5061039;IECKAVQTURBPON-UHFFFAOYSA-;alpha,alpha,alpha-Trimethoxytoluene;NSC67391;BBL027715;STL185669;AKOS009158355;AS-10661;SY048255;CS-0011453;FT-0654327;T2287;EN300-82362;F16433;.ALPHA.,.ALPHA.,.ALPHA.-TRIMETHOXYTOLUENE;A836971;Q27231270

Chemical Property of Trimethyl orthobenzoate

Chemical Property:

• Appearance/Colour: clear colorless liquid
• Vapor Pressure: 0.344mmHg at 25°C
• Refractive Index: n20/D 1.489(lit.)
• Boiling Point: 223.9 °C at 760 mmHg
• Flash Point: 82.2 °C
• PSA: 27.69000
• Density: 1.04 g/cm³
• LogP: 1.73610
• Storage Temp.: Inert atmosphere,Room Temperature
• Sensitive.: Moisture Sensitive
• Solubility.: Soluble in organic solvents.
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 182.094294304
• Heavy Atom Count: 13
• Complexity: 129

Purity/Quality:

99% ^*data from raw suppliers

Trimethyl Orthobenzoate >95.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(C1=CC=CC=C1)(OC)OC
• Uses: Trimethyl Orthobenzoate is a reagent used in the synthesis of quinazolines. Also used in the prepaaration of nintedanib (N478290), used in the treatment of idiopathic pulmonary fibrosis. Also inhibits the process blood vessel formation which may be used to assist in cancer therapy.

Technology Process of Trimethyl orthobenzoate

There total 27 articles about Trimethyl orthobenzoate 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: 98.0%

methanol (67-56-1) + C11H12O2S2 → orthobenzoic acid trimethyl ester (707-07-3)

Guidance literature:

With sodium methylate; Electrochemical reaction; Green chemistry;

DOI:10.1021/acs.orglett.0c01324

Reference yield: 86.0%

methanol (67-56-1) + N-methyl-N-phenyl-benzamide (1934-92-5) + sodium methylate (124-41-4) + methyl trifluoromethanesulfonate (333-27-7) → orthobenzoic acid trimethyl ester (707-07-3)

Guidance literature:

N-methyl-N-phenyl-benzamide; methyl trifluoromethanesulfonate; In dichloromethane; at 20 ℃; for 20h;

methanol; sodium methylate; at 20 ℃; for 0.166667h;

With acetic acid; In methanol; at 20 ℃; for 0.25h;

DOI:10.1021/acs.joc.9b00108

Reference yield: 85.6%

methanol (67-56-1) + benzaldehyde dimethyl acetal (1125-88-8) → benzoic acid methyl ester (93-58-3,5705-52-2,80226-58-0) + orthobenzoic acid trimethyl ester (707-07-3)

Guidance literature:

With sodium methylate; lithium perchlorate; Tris(2,4-dibromophenyl)amine; In dichloromethane; indirect electrochemical oxidation;

DOI:10.1016/S0040-4020(01)87454-8

upstream raw materials:

tetramethoxymethane

sodium methylate

Benzotrichlorid

methyl dithiobenzoate

Downstream raw materials:

2-phenyl-2-methoxy-1,3-dioxolane

2-(methoxyphenylmethylene)malononitrile

3-Phenyl-2,4,10-trioxa-adamantane

trimethyloxonium hexachloroantimonate^(1-)

Refernces

• 1、 Cortigiani, Mauro,Gillick Healy, Malachi,Mereu, Andrea,Adamo, Mauro F. A.. "Enantioselective Desymmetrization of cis-3,5- O-Arylidenecyclohexanones Catalyzed by Cinchona-Derived Quaternary Ammonium Salts". . p. 4112 - 4119. Retrieved 2019/04/30.
• 2、 Ogibin, Yu. N.,Sokolov, A. B.,Ilovaiskii, A. I.,Elison, M. N.,Nikishin, G. I.. "ELECTROCHEMICAL CLEAVAGE OF THE DOUBLE BOND OF 1-ALKENYLARENES". . p. 561 - 566. Retrieved 2007/10/02.