Product Introduction
| Trimethoxymethane Basic information |
| Product Name: | Trimethoxymethane |
| Synonyms: | orthoformicacidmethylester;Thrimethyl orthoformate;TRIMETHYL ORTHOFORMATE, ANHYDROUS, 99.8%;TrimethylOrthoFormate(Tmof);Trimethylorthoformate, 98+%;METHYLFORMIAT-ORTHO;Trimethylorthoformiat;TRIMETHYL ORTHOFORMATE 98.5% |
| CAS: | 149-73-5 |
| MF: | C4H10O3 |
| MW: | 106.12 |
| EINECS: | 205-745-7 |
| Product Categories: | Organic synthesis;straight chain compounds;Orthoesters;149-73-5 |
| Mol File: | 149-73-5.mol |
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| Trimethoxymethane Chemical Properties |
| Melting point | -53 °C |
| Boiling point | 101-102 °C(lit.) |
| density | 0.97 g/mL at 25 °C(lit.) |
| vapor density | 3.67 (vs air) |
| vapor pressure | 23.5 mm Hg ( 20 °C) |
| refractive index | n20/D 1.379(lit.) |
| Fp | 60 °F |
| storage temp. | Store below +30°C. |
| solubility | Miscible with ether, alcohol and benzene. |
| form | Liquid |
| color | Clear colorless |
| explosive limit | 1.4-44.6%(V) |
| Water Solubility | 10 g/L (hydrolysis) |
| Sensitive | Moisture Sensitive |
| Merck | 14,6884 |
| BRN | 969215 |
| InChIKey | PYOKUURKVVELLB-UHFFFAOYSA-N |
| LogP | -0.03-0.09 at 20℃ |
| CAS DataBase Reference | 149-73-5(CAS DataBase Reference) |
| NIST Chemistry Reference | Methane, trimethoxy-(149-73-5) |
| EPA Substance Registry System | Trimethoxymethane (149-73-5) |
| Safety Information |
| Hazard Codes | F,Xi |
| Risk Statements | 11-36 |
| Safety Statements | 9-16-26-29 |
| RIDADR | UN 3272 3/PG 2 |
| WGK Germany | 1 |
| RTECS | RM6650000 |
| Autoignition Temperature | 255 °C |
| TSCA | Yes |
| HazardClass | 3 |
| PackingGroup | II |
| HS Code | 29159080 |
| Hazardous Substances Data | 149-73-5(Hazardous Substances Data) |
| Toxicity | LD50 orally in Rabbit: 3130 mg/kg |
| MSDS Information |
| Provider | Language |
|---|---|
| Methyl orthoformate | English |
| SigmaAldrich | English |
| ACROS | English |
| ALFA | English |
| Trimethoxymethane Usage And Synthesis |
| 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. |
| Chemical Properties | Colorless liquid |
| 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. |
| Uses | 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. |
| Uses | 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. |
| Application | Trimethyl orthoformate was used as dehydrating agent in the preparation of surface-modified colloidal silica nanoparticles. MOM protection of Diols using Trimethyl Orthoformate N-Formylation of Amino Acid Esters |
| General 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. |
| Flammability and Explosibility | Highly flammable |
| Safety Profile | A skin and eye irritant. A very dangerous fire hazard when exposed to heat or flame; can react with oxidizing materials. Hazardous to prepare. To fight fire, use CO2, fog, haze. When heated to decomposition it emits acrid smoke and irritating fumes. See also ESTERS. |
| 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. |
| Precautions | Moisture sensitive. Keep the container tightly closed in a dry and well-ventilated place. Incompatible with acids and strong oxidizing agents. |
| References | Protection for the Hydroxyl Group, Including 1,2- and 1,3-Diols P. G. M. Wuts, in Greene's Protective Groups in Organic Synthesis, 5th ed., ed. by P. G. M. Wuts, John Wiley & Sons, Inc., Hoboken, New Jersey, 2014, Chap. 2, 17. A Facile Procedure for the Synthesis of N-Formyl Amino Acid Esters T. Chancellor, C. Morton, Synthesis 1994, 10, 1023. |
| Trimethoxymethane Preparation Products And Raw materials |
| Raw materials | Sodium hydroxide-->Sodium-->Chloroform |
| Preparation Products | N-METHYL-P-ANISIDINE-->N-Boc-5,6,7,8-tetrahydro-3-methoxy-[1,2,4]triazolo[4,3-A]pyrazine ,98%-->6-BROMO-4-CHLOROQUINOLINE-->5,6-DIHYDRO-4-METHOXY-2H-PYRAN-->4,7-DIMETHOXY-1,10-PHENANTHROLINE, 97%-->4-TRIFLUOROMETHYL-N-METHYLANILINE 97-->3-METHOXY-N-METHYLANILINE-->6-bromoquinolin-4(3H)-one-->Pipemidic acid-->Methyl trifluoroacetate-->Methyl methanesulfonate-->Tetramethoxyethylene-->ETHYL 5-AMINO-1-PYRIDIN-2-YL-1H-PYRAZOLE-4-CARBOXYLATE-->Bromoform-->THEBAINE-->2-Methylundecanal dimethylacetal-->(-)-Dimethyl D-tartrate-->P-ANISALDEHYDE DIMETHYL ACETAL-->6,7-DIHYDRO-2-PHENYL-5H-PYRROLO[2,1-C]-1,2,4-TRIAZOLIUM CHLORIDE-->BASIC RED 12 |
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