Trimethoxymethane

Base Information

• Chemical Name: Trimethoxymethane
• CAS No.: 149-73-5
• Deprecated CAS: 251301-35-6
• Molecular Formula: C4H10O3
• Molecular Weight: 106.122
• Hs Code.: 29159080
• European Community (EC) Number: 205-745-7
• NSC Number: 147479
• UNII: XAM28819YJ
• DSSTox Substance ID: DTXSID7027122
• Nikkaji Number: J8.664I
• Wikipedia: Trimethyl_orthoformate
• Wikidata: Q408190
• ChEMBL ID: CHEMBL3187679
• Mol file: 149-73-5.mol

Synonyms:Trimethoxymethane;TRIMETHYL ORTHOFORMATE;149-73-5;Methyl orthoformate;Methane, trimethoxy-;Orthoformic acid methyl ester;Orthoformic acid, trimethyl ester;Orthomravencan methylnaty;Methoxymethylal;Methylester kyseliny orthomravenci;trimethoxy-methane;NSC 147479;Orthoformic acid trimethyl ester;HSDB 1006;Orthomravencan methylnaty [Czech];Trimethylester kyseliny orthomravenci;EINECS 205-745-7;Orthoformic acid trimethyl;BRN 0969215;UNII-XAM28819YJ;CH(OCH3)3;Methylester kyseliny orthomravenci [Czech];AI3-23842;XAM28819YJ;DTXSID7027122;Trimethylester kyseliny orthomravenci [Czech];NSC-147479;EC 205-745-7;4-02-00-00022 (Beilstein Handbook Reference);trimethyl ortho formate;trimethoxy methane;trimethylorthoformat;trimethylorthoformate;trimetyl orthoformate;trirnethylorthoformate;MFCD00008483;trimethyl-orthoformate;trimethylortho-formate;tri-methyl orthoformate;trim ethyl orthoformate;trimethyl ortho-formate;trimethyl-ortho-formate;PERMA-FLO OF;(MeO)3CH;CH(OMe)3;HC(OMe)3;C(OC)(OC)OC;SCHEMBL6919;Trimethyl orthoformate, 99%;(CH3O)3CH;HC(OCH3)3;DTXCID307122;ortho-formic acid trimethylester;CHEMBL3187679;WLN: 1OYO1 & O1;ortho-formic acid trimethyl ester;PYOKUURKVVELLB-UHFFFAOYSA-;AMY41181;Tox21_200062;NSC147479;STL185659;TRIMETHYL ORTHOFORMATE [HSDB];AKOS000121043;NCGC00248510-01;NCGC00257616-01;BP-21313;CAS-149-73-5;LS-98477;Trimethyl orthoformate, anhydrous, 99.8%;O0068;ORTHOFORMIC ACID TRIMETHYL ESTER [MI];EN300-21653;A808947;Q408190;Q-201888;F0001-0529;(Trimethyl orthoformate)

Chemical Property of Trimethoxymethane

Chemical Property:

• Appearance/Colour: Colorless transparent liquid
• Vapor Pressure: 23.5 mm Hg ( 20 °C)
• Melting Point: -53 °C
• Refractive Index: n20/D 1.379(lit.)
• Boiling Point: 104 °C at 760 mmHg
• Flash Point: 15.6 °C
• PSA: 27.69000
• Density: 0.93 g/cm³
• LogP: 0.20920
• Storage Temp.: Store at RT.
• Sensitive.: Moisture Sensitive
• Solubility.: Miscible with ether, alcohol and benzene.
• Water Solubility.: 10 g/L (hydrolysis)
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 106.062994177
• Heavy Atom Count: 7
• Complexity: 28.4

Purity/Quality:

99% ^*data from raw suppliers

Trimethyl orthoformate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xi
• Hazard Codes: F,Xi
• Statements: 11-36
• Safety Statements: 9-16-26-29

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Ethers, Other
• Canonical SMILES: COC(OC)OC
• Description: Trimethyl orthoformate is an effective solvent for thallium(III) nitrate-mediated oxidations. It undergoes acid catalyzed reaction with 6-(N-D-ribitylanilino) uracils to form 8-demethyl-8-hydroxy-5-deazariboflavins.
• Uses: Trimethyl orthoformate is used as a protecting group for aldehydes in organic synthesis, as an additive in polyurethane coatings and as a dehydrating agent in the preparation of surface modified colloidal silica nanoparticles. It is also used as a chemical intermediate in the preparation of vitamin B1 and sulfa drugs. It acts as an effective solvent for thallium(III) nitrate-mediated oxidations. Furthermore. It is utilized for the synthesis of chromone from keto-hydroxy naphthol in the presence of trimethylamine. Trimethyl Orthoformate is the most simple orthoester. Used in organic synthesis as a reagent for introducing a protecting group for aldehydes and in the creation of methoxymethylene groups and heterocyclic ring systems. Trimethyl orthoformate can be used:To convert sulfonic acids to methyl esters.To convert 2-acylcyclohexanones to the corresponding acetal derivatives.To mediate Pinacol reaction of various 1,2-diols with tin(IV) chloride without the formation of water.To synthesize 1-substituted-1H-1,2,3,4-tetrazoles via a three-component condensation with amine and sodium azide catalyzed by indium triflate under solvent-free conditions.For the N-methylation of amines in the presence of sulfuric acid.

Technology Process of Trimethoxymethane

There total 34 articles about Trimethoxymethane 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: 90.0%

Dimethyl ether (115-10-6,157621-61-9) + Methyl formate (107-31-3) → trimethyl orthoformate (149-73-5)

Guidance literature:

With boron trifluoride; In Hexadecane; at 110 ℃; for 12h; Autoclave;

Reference yield: 89.7%

methanol (67-56-1) + hydrogen cyanide (74-90-8) → trimethyl orthoformate (149-73-5)

Guidance literature:

methanol; hydrogen cyanide; With hydrogenchloride; In cyclohexane; water; at -15 - 35 ℃; Large scale;

In cyclohexane; water; at 50 - 60 ℃; for 24h; pH=3 - 4; Solvent; Large scale;

Reference yield: 88.0%

1'-naphthacetophenone (941-98-0) → Bromoform (75-25-2) + methyl 1-naphthoate (2459-24-7) + trimethyl orthoformate (149-73-5)

Guidance literature:

With methanol; sodium bromide; at 30 ℃; electrolysis (Pt-anode, Cu-Zn (60:40)-cathode, 220 mA/cm² constant current density);

DOI:10.1016/S0040-4020(01)87078-2

upstream raw materials:

methanol

hydrogen cyanide

chloroform

formimidomethylester hydrochloride

Downstream raw materials:

4-(dimethoxymethyl)phenol

N-(4-chlorophenyl)-N-methylformamide

2-(dimethoxymethyl)phenol

1-ethoxy-1,3,3-trimethoxypropane

Refernces

• 1、 Anelli, Pier Lucio,Brocchetta, Marino,Copez, Debora,Palano, Daniela,Visigalli, Massimo,Paoli, Paola. "Unexpected formation of acylformamidines by reaction of primary carboxamides with MeONa in DMF in the presence of CHCl3". . p. 15827 - 15832. Retrieved 1997.
• 2、 Hine,Porter. "-". . p. 5493,5494,5495. Retrieved 1957.
• 3、 -. "Synthesis method of crude carboxylic ester (by machine translation)". Paragraph 0021; 0022. . Retrieved 2020/08/09.
• 4、 -. "Method for producing high purity orthoformate simple and convenient method of". Paragraph 0014-0017; 0029-0031. . Retrieved 2017/12/04.