Trimethyl orthoformate (TMOF) is the organic compound with the formula HC(OCH3)3. A colorless liquid, it is the simplest orthoester. It is a reagent used in organic synthesis for the formation of methyl ethers.[3] The product of reaction of an aldehyde with trimethyl orthoformate is an acetal. In general cases, these acetals can be deprotected back to the aldehyde by using hydrochloric acid.
Trimethyl orthoformate is a useful building block for creating methoxymethylene groups and heterocyclic ring systems. It introduces a formyl group to a nucleophilic substrate, e.g. RNH2 to form R-NH-CHO, which can undergo further reactions. It is used in the production of the fungicides, azoxystrobin, and picoxystrobin, as well as for some members of the floxacin family of antibacterial drugs.
A number of pharmaceutical intermediates are also made from trimethyl orthoformate.[4]
Trimethyl orthoformate is also an effective reagent for converting compatible carboxylic acids to their corresponding methyl esters.[5] Alternatively, acid-catalyzed esterifications with methanol can be driven closer to completion by employing trimethyl orthoformate to convert water byproduct to methanol and methyl formate.
^Liu, Hui; Tomooka, Craig S.; Xu, Simon L.; Yerxa, Benjamin R.; Sullivan, Robert W.; Xiong, Yifeng; Moore, Harold W. (1999). "Dimethyl Squarate and ITS Conversion to 3-Ethenyl-4-Methoxycyclobutene-1,2-Dione and 2-Butyl-6-Ethenyl-5-Methoxy-1,4-Benzoquinone". Organic Syntheses. 76: 189. doi:10.15227/orgsyn.076.0189.
^ abAshford's Dictionary of Industrial Chemicals, Third edition, 2011, ISBN978-0-9522674-3-0, page 9388
^Paine, John B. (1 July 2008). "Esters of Pyromellitic Acid. Part I. Esters of Achiral Alcohols: Regioselective Synthesis of Partial and Mixed Pyromellitate Esters, Mechanism of Transesterification in the Quantitative Esterification of the Pyromellitate System Using Orthoformate Esters, and a Facile Synthesis of the Ortho Pyromellitate Diester Substitution Pattern". The Journal of Organic Chemistry. 73 (13): 4929–4938. doi:10.1021/jo800543w.
January 29, 2023
trimethyl, orthoformate, tmof, organic, compound, with, formula, och3, colorless, liquid, simplest, orthoester, reagent, used, organic, synthesis, formation, methyl, ethers, product, reaction, aldehyde, with, trimethyl, orthoformate, acetal, general, cases, th. Trimethyl orthoformate TMOF is the organic compound with the formula HC OCH3 3 A colorless liquid it is the simplest orthoester It is a reagent used in organic synthesis for the formation of methyl ethers 3 The product of reaction of an aldehyde with trimethyl orthoformate is an acetal In general cases these acetals can be deprotected back to the aldehyde by using hydrochloric acid Trimethyl orthoformate 1 NamesPreferred IUPAC name TrimethoxymethaneOther names 2 Methoxyacetaldehyde dimethyl acetal Methoxymethylal Methyl orthoformateIdentifiersCAS Number 149 73 5 Y3D model JSmol Interactive imageChemSpider 8655ECHA InfoCard 100 005 224EC Number 205 745 7PubChem CID 9005UNII XAM28819YJ YCompTox Dashboard EPA DTXSID7027122InChI InChI 1S C4H10O3 c1 5 4 6 2 7 3 h4H 1 3H3SMILES O C C OC OCPropertiesChemical formula C 4H 10O 3Molar mass 106 121 g mol 1Appearance Colorless liquidOdor pungentDensity 0 9676 g cm3Melting point 53 C 63 F 220 K Boiling point 100 6 C 213 1 F 373 8 K Solubility soluble in ethanol etherVapor pressure 1 kPa at 7 C 2 Refractive index nD 1 3773HazardsGHS labelling PictogramsSignal word DangerHazard statements H225 H315 H319 H335Precautionary statements P210 P233 P240 P241 P242 P243 P261 P264 P271 P280 P302 P352 P303 P361 P353 P304 P340 P305 P351 P338 P312 P321 P332 P313 P337 P313 P362 P370 P378 P403 P233 P403 P235 P405 P501Flash point 13 C 55 F 286 K Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox references Contents 1 Synthesis 2 Use 3 See also 4 ReferencesSynthesis EditTrimethyl orthoformate is prepared on an industrial scale by the methanolysis of hydrogen cyanide 4 HCN 3 HOCH3 HC OCH3 3 NH3Trimethyl orthoformate can also be prepared from the reaction between chloroform and sodium methoxide an example of the Williamson ether synthesis Use EditTrimethyl orthoformate is a useful building block for creating methoxymethylene groups and heterocyclic ring systems It introduces a formyl group to a nucleophilic substrate e g RNH2 to form R NH CHO which can undergo further reactions It is used in the production of the fungicides azoxystrobin and picoxystrobin as well as for some members of the floxacin family of antibacterial drugs A number of pharmaceutical intermediates are also made from trimethyl orthoformate 4 Trimethyl orthoformate is also an effective reagent for converting compatible carboxylic acids to their corresponding methyl esters 5 Alternatively acid catalyzed esterifications with methanol can be driven closer to completion by employing trimethyl orthoformate to convert water byproduct to methanol and methyl formate See also EditPinner reactionReferences Edit Trimethyl orthoformate at Sigma Aldrich Alfa Aesar SDS Liu Hui Tomooka Craig S Xu Simon L Yerxa Benjamin R Sullivan Robert W Xiong Yifeng Moore Harold W 1999 Dimethyl Squarate and ITS Conversion to 3 Ethenyl 4 Methoxycyclobutene 1 2 Dione and 2 Butyl 6 Ethenyl 5 Methoxy 1 4 Benzoquinone Organic Syntheses 76 189 doi 10 15227 orgsyn 076 0189 a b Ashford s Dictionary of Industrial Chemicals Third edition 2011 ISBN 978 0 9522674 3 0 page 9388 Paine John B 1 July 2008 Esters of Pyromellitic Acid Part I Esters of Achiral Alcohols Regioselective Synthesis of Partial and Mixed Pyromellitate Esters Mechanism of Transesterification in the Quantitative Esterification of the Pyromellitate System Using Orthoformate Esters and a Facile Synthesis of the Ortho Pyromellitate Diester Substitution Pattern The Journal of Organic Chemistry 73 13 4929 4938 doi 10 1021 jo800543w Retrieved from https en wikipedia org w index php title Trimethyl orthoformate amp oldid 1055797725, wikipedia, wiki, book, books, library,
