PRODUCTS

TRIMETHYL ORTHOFORMATE

Trimethyl orthoformate (TMOF) is the organic compound with the formula HC(OCH3)3.
A colorless liquid, trimethyl orthoformate is the simplest orthoester.
Trimethyl orthoformate is a reagent used in organic synthesis for the formation of methyl ethers.
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.

CAS number: 149-73-5
EC number: 205-745-7

IUPAC Name: trimethoxymethane

Molecular Formula: C4H10O3
Molecular Weight: 106.12 g/mol

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, Trimethylester kyseliny orthomravenci, CH(OCH3)3, XAM28819YJ, DTXSID7027122, MFCD00008483, NSC-147479, HSDB 1006, trimethyl ortho formate, Orthomravencan methylnaty [Czech], EINECS 205-745-7, Orthoformic acid trimethyl, BRN 0969215, UNII-XAM28819YJ, Methylester kyseliny orthomravenci [Czech], AI3-23842, Trimethylester kyseliny orthomravenci [Czech], trimethoxy methane, trimethylorthoformat, trimethylorthoformate, trimetyl orthoformate, trirnethylorthoformate, 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, EC 205-745-7, SCHEMBL6919, Trimethyl orthoformate, 99%, (CHO)3CH, 4-02-00-00022 (Beilstein Handbook Reference), 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-13013, Trimethyl orthoformate, anhydros, 99.8%, NS00005988, O0068, ORTHOFORMIC ACID TRIMETHYL ESTER [MI], EN300-21653, A808947, Q408190, Q-201888, F0001-0529, InChI=1/C4H10O3/c1-5-4(6-2)7-3/h4H,1-3H3

Trimethyl orthoformate is a commonly used reagent in organic synthesis for the preparation of useful building blocks.
Trimethyl orthoformate is also used to introduce the protecting group for aldehydes by the preparation of acetals.
Acetals can be deprotected back to the aldehyde by using acid catalysts.

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.
Trimethyl orthoformate is also used as a chemical intermediate in the preparation of vitamin B1 and sulfa drugs.
Trimethyl orthoformate acts as an effective solvent for thallium(III) nitrate-mediated oxidations.
Furthermore, Trimethyl orthoformate is utilized for the synthesis of chromone from keto-hydroxy naphthol in the presence of trimethylamine.

Solubility: Miscible with ether, alcohol and benzene.

Trimethyl orthoformate (TMOF) is the organic compound with the formula HC(OCH₃)₃.
A colorless liquid, Trimethyl orthoformate is the simplest orthoester.
Trimethyl orthoformate is a reagent used in organic synthesis for the formation of methyl ethers.
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 the simplest orthoester.
Trimethyl orthoformate is a reagent used in organic synthesis for the introduction of a protecting group for aldehydes.
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.
The industrial synthesis of Trimethyl orthoformate is from hydrogen cyanide and methanol.
Trimethyl orthoformate is a useful building block for creating methoxymethylene groups and heterocyclic ring systems.
Trimethyl orthoformate introduces a formyl group to a nucleophilic substrate, e.g. RNH2 to form R-NH-CHO, which can undergo further reactions.
Trimethyl orthoformate 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.

Trimethyl orthoformate is an effective solvent for thallium(III) nitrate-mediated oxidations.
Trimethyl orthoformate undergoes acid catalyzed reaction with 6-(N-D-ribitylanilino) uracils to form 8-demethyl-8-hydroxy-5-deazariboflavins.
Trimethyl orthoformate was used as dehydrating agent in the preparation of surface-modified colloidal silica nanoparticles.

Trimethyl orthoformate, with the chemical formula C4H10O3, is an organic compound that serves as a valuable reagent in organic synthesis.
This colorless liquid is widely utilized in various fields, including the pharmaceutical and fine chemical industries.
Trimethyl orthoformate's versatility and ability to generate diverse reactive species make it a valuable tool in organic chemistry.

In organic synthesis, trimethyl orthoformate finds extensive application.
Trimethyl orthoformate plays a crucial role in the preparation of pharmaceuticals and other fine chemicals, where it acts as a key building block.
Additionally, trimethyl orthoformate plays a significant part in the production of agricultural intermediates, which are vital for creating pesticides, herbicides, and Plant Growth Regulators (PGRs).

One notable application of trimethyl orthoformate is its use as a protecting group for alcohols.
By employing an acid catalyst and treating an alcohol with trimethyl orthoformate, it is possible to convert the alcohol into an acetate or acetal derivative.
This protective modification shields the alcohol functionality from undesired reactions.
Later, under mild conditions, the trimethyl orthoformate can be easily removed, restoring the original alcohol.

While not directly involved in the synthesis of sulfa drugs, trimethyl orthoformate may serve as a reagent or intermediate in specific steps of the process.
Sulfa drugs, a class of antibiotics containing sulfonamide functional groups, rely on complex synthesis routes.
In these routes, trimethyl orthoformate may contribute to the production of certain intermediates.

Furthermore, trimethyl orthoformate can be employed as an intermediate in the synthesis of vitamin B1, also known as thiamine.
Vitamin B1 is an essential nutrient that plays a crucial role in various biological processes.

Trimethyl orthoformate, with the chemical formula (CH3O)3CH, is an organic compound commonly used as a reagent in organic synthesis.
Trimethyl orthoformate appears as a colorless liquid with a pungent odor.

Acylation Reactions: Trimethyl orthoformate is used as a reagent in acylation reactions to introduce formyl groups into organic compounds.

Protecting Group: Trimethyl orthoformate serves as a protecting group for alcohols in organic synthesis, preventing unwanted reactions at the hydroxyl group.

Methylation Reactions: Trimethyl orthoformate is employed in methylation reactions, where it serves as a source of methyl groups.

Intermediate: Trimethyl orthoformate is utilized as an intermediate in the pharmaceutical and agrochemical industries for the synthesis of various compounds.

Trimethyl orthoformate is a glycoside that is used as a substrate for the production of methyl glycosides.
Trimethyl orthoformate has been shown to have antibacterial activity in vitro against gram-positive bacteria and methicillin-resistant Staphylococcus aureus (MRSA).
Trimethyl orthoformate can be synthesized by condensation of formaldehyde and methanol with sodium ethoxide, followed by hydrolysis with dilute acid.
Trimethyl orthoformate can also be prepared from trimethylamine and formaldehyde with sodium ethoxide in acidic media.
The reaction mechanism of this reaction involves the formation of an iminium ion intermediate, which undergoes nucleophilic attack by water followed by elimination of hydrogen cyanide to form the desired product.
Methyl glycosides are formed when trimethyl orthoformate reacts with acetic anhydride or acetone.
These compounds inhibit bacterial growth by inhibiting protein synthesis at the ribosome level.

Trimethyl Orthoformate is a colorless liquid with pungent smell.
Trimethyl orthoformate is flammable and decomposes when meeting water.
Trimethyl orthoformate can be dissolved in ethanol, ether, etc.
Trimethoxymethane is an important organic synthesis intermediate, which is used in the synthesis of many kinds of medicine, dyes and spices.

Trimethyl orthoformate is mainly used as an intermediate in organic synthesis and widely used in pharmaceutical synthesis, such as the synthesis of vitamin B1, vitamin B, sulfadiazine, Pipemidic Acid drugs, antibiotics, etc;

In terms of coatings, Trimethyl Orthoformate is a dehydrating agent used to prevent the hardening of polyurethane or epoxy coatings due to hydration; it can also be used for the synthesis of dyes and perfumes.

Use
Trimethyl orthoformate is a useful building block for creating methoxymethylene groups and heterocyclic ring systems.
Trimethyl orthoformate introduces a formyl group to a nucleophilic substrate, e.g. RNH2 to form R-NH-CHO, which can undergo further reactions.
Trimethyl orthoformate is used in the production of some fungicides (for example: 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.

Trimethyl orthoformate is also an effective reagent for converting compatible carboxylic acids to their corresponding methyl esters.
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.

Trimethyl orthoformate is the simplest orthoester.
Trimethyl orthoformate is aa reagent used in organic synthesis for the introduction of a protecting groupfor aldehydes.
The product of reactaion 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.
The industrial synthesis of this chemical is from hydrogen cyanide and methanol.
Trimethyl orthoformate is a useful building block for creating methoxymethylene groups and heterocyclic ring system.
Trimethyl orthoformate introduces a formyl group to a nucleophillic substrate, e.g. RNH2 to form r-nh-cho , which can undergo further reactions.
Trimethyl orthoformate is used in the production of the fungicides.
Azoxystrobin and picoxystrobin, as well as for some members of the floxacin family of antibacterial trimethyl orthoromate also find application in aromatic fragrance manufacturing industry.

Synthesis
Trimethyl orthoformate is prepared on an industrial scale by the methanolysis of hydrogen cyanide:

HCN + 3 HOCH3 → HC(OCH3)3 + NH3
Trimethyl orthoformate can also be prepared from the reaction between chloroform and sodium methoxide, an example of the Williamson ether synthesis.

The preparation method of the trimethyl orthoformate comprises the steps of obtaining amine salt by reaction between hydrocyanic acid and carbinol and hydrogen chloride and obtaining a trimethyl orthoformate coarse product through alcoholysis; and carrying out centrifugal separation on alcoholysis reaction liquid, and refining the obtained coarse product by adding aqueous alkali.
The purity of the trimethyl orthoformate product obtained with the refining method can reach to 99.6%-99.8wt%, triazine impurity content is pretty small and is only 0.001-0.06%, and particularly purification yield of the refining method is more than 90% and can reach to 96% to the maximum degree.
According to the trimethyl orthoformate and the preparation method of the trimethyl orthoformate, treating agents can be obtained easily, cost is low, reaction condition is moderate, and the trimethyl orthoformate and the preparation method of the trimethyl orthoformate are particularly suitable for industrial mass production.

Physicochemical Information

Boiling point: 102 °C (1013 hPa)
Density: 0.96 g/cm3 (20 °C)
Explosion limit: 1.4 - 44.6 %(V)
Flash point: 13 °C
Ignition temperature: 255 °C
Melting Point: -53 °C
Vapor pressure: 10 hPa (7 °C)
Solubility: 10 g/l Hydrolysis

Product Information

CAS number: 149-73-5
EC number: 205-745-7
Hill Formula: C₄H₁₀O₃
Chemical formula: CH(OCH₃)₃
Molar Mass: 106.12 g/mol

Application
• 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.

• Trimethyl orthoformate is the simplest orthoester.
Trimethyl orthoformate is aa reagent used in organic synthesis for the introduction of a protecting groupfor aldehydes.
The product of reactaion 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.

• The industrial synthesis of this chemical is from hydrogen cyanide and methanol.

• Trimethyl orthoformate is a useful building block for creating methoxymethylene groups and heterocyclic ring system.
Trimethyl orthoformate introduces a formyl group to a nucleophillic substrate, e.g. RNH2 to form r-nh-cho , which can undergo further reactions.
Trimethyl orthoformate is used in the production of the fungicides.
Azoxystrobin and picoxystrobin, as well as for some members of the floxacin family of antibacterial trimethyl orthoromate also find application in aromatic fragrance manufacturing industry.

• Acylation Reactions: Trimethyl orthoformate is used as a reagent in acylation reactions to introduce formyl groups into organic compounds.

• Protecting Group: Trimethyl orthoformate serves as a protecting group for alcohols in organic synthesis, preventing unwanted reactions at the hydroxyl group.

• Methylation Reactions: Trimethyl orthoformate is employed in methylation reactions, where it serves as a source of methyl groups.

• Intermediate: Trimethyl orthoformate is utilized as an intermediate in the pharmaceutical and agrochemical industries for the synthesis of various compounds.

Trimethyl orthoformate is the simplest orthoester.
Trimethyl orthoformate is a reagent used in organic synthesis for the introduction of a protecting group for aldehydes.
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.
The industrial synthesis of this chemical is from hydrogen cyanide and methanol.
Trimethyl orthoformate is a useful building block for creating methoxymethylene groups and heterocyclic ring systems.
Trimethyl orthoformate introduces a formyl group to a nucleophilic substrate, e.g. RNH2 to form R-NH-CHO, which can undergo further reactions.
Trimethyl orthoformate 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.

Physical Properties

Physical state at 20 °C: Liquid
Colour:   Clear Colorless
Odour: Pungent,Aromatic, ester-like
Melting point/ Freezing point [°C]: -53°C
Auto-ignition temperature [°C]:   255 °C
Flammability (solid, gas): Flammable
Flash point [°C]: 13 °C
Boiling point [°C]: 101 - 102 °C
Initial boiling point [°C]: 101 °C
Final boiling point [°C]: 102 °C
Vapour pressure [20°C]:   53 hPa at 30 °C
Vapour density:   3.67
Density [g/cm3]: 0.9676
Solubility in water [% weight]:   Hydrolyzes in water
Partition coefficient Log Pow octanol / water at 20°C: 0.3
Explosion limits - upper [%]: 5.10%
Explosion limits -lower [%]: 1.40%

Notes
Moisture sensitive.
Keep the container tightly closed in a dry and well-ventilated place.
Incompatible with acids and strong oxidizing agents.