Trimethyl orthoformate
TRIMETHYL ORTHOFORMATE · TMOF · CH(OCH3)3 · ch(ome)3 · METHYL ORTHOFORMATE · Trimethyl ester · Thrimethyl orthoformate · orthoformicacidmethylester
Identifiers & Physical Properties
| CAS No. | 149-73-5 |
|---|---|
| Molecular formula | C4H10O3 |
| Average molar mass | 106.12 g/mol |
| Monoisotopic mass | 106.06299418 g/mol |
| SMILES | COC(OC)OC |
| InChIKey | PYOKUURKVVELLB-UHFFFAOYSA-N |
| PubChem CID | 9005 |
| ChEMBL | CHEMBL3187679 |
| EC No. | 205-745-7 |
| DTXSID | DTXSID7027122 |
Chemical & Physical Properties
| XLogP | 0.2 |
|---|---|
| Topological polar surface area | 27.7 |
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 3 |
| Rotatable bonds | 3 |
| Heavy atoms | 7 |
| Formal charge | 0 |
| Complexity | 28.4 |
| Chemical classes | Other Classes -> Ethers, Other |
| SpringerMaterials Properties | Schoenflies notation |
| Odor | PUNGENT ODOR |
| Density | 0.9676 @ 20 °C/4 °C0.9676 @ 20°C0.97 g/mL at 25 °C(lit.) |
| Color/Form | COLORLESS LIQUID |
| Solubility | SOL IN ETHANOL, IN ETHERMiscible with ether, alcohol and benzene.10 g/L (hydrolysis) |
| Boiling point | 100.6 °C @ 760 MM HG100.6 °C @760 [mm Hg]101-102 °C(lit.) |
| Vapor density | 3.67 (AIR= 1)3.67 (vs air) |
| Vapor pressure | 81.4 [mmHg]23.5 mm Hg ( 20 °C) |
| Refractive index | INDEX OF REFRACTION: 1.3773 @ 25 °C/Dn20/D 1.379(lit.) |
| Physical Description | LiquidColorless liquid with a pungent odor[HSDB] |
| Melting point | -53 °C |
| Flash point | 60 °F |
| Storage conditions | Store below +30°C. |
| Physical state | Liquid |
| Color | Clear colorless |
| Explosive limits | 1.4-44.6%(V) |
| Sensitivity | Moisture Sensitive |
| Merck | 14,6884 |
| BRN | 969215 |
| Henry's law constant | 6.9×10-1 mol/(m3Pa) at 25℃, Guthrie (1973) |
| InChI | 1S/C4H10O3/c1-5-4(6-2)7-3/h4H,1-3H3 |
| InChIKey | PYOKUURKVVELLB-UHFFFAOYSA-N |
| SMILES | COC(OC)OC |
| LogP (partition coefficient) | -0.03-0.09 at 20℃ |
| CAS DataBase Reference | 149-73-5(CAS DataBase Reference) |
| FDA UNII | XAM28819YJ |
| NIST Chemistry Reference | Methane, trimethoxy-(149-73-5) |
| EPA Substance Registry System | Trimethoxymethane (149-73-5) |
| UNSPSC Code | 12352112 |
| NACRES | NA.22 |
| GHS pictogram | GHS02,GHS07 |
| Signal word | Danger |
| GHS hazard statements | H316-H319-H225 |
| GHS precautionary statements | P501-P240-P210-P233-P243-P241-P242-P264-P280-P370+P378-P337+P313-P305+P351+P338-P303+P361+P353-P332+P313-P403+P235 |
| Target organs | Respiratory system |
| Personal protective equipment (PPE) | Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter |
| Hazard symbols | F,Xi |
| Risk statements (R) | 11-36 |
| Safety statements (S) | 9-16-26-29 |
| UN transport number | UN 3272 3/PG 2 |
| Water hazard class (WGK) | 1 |
| RTECS number | RM6650000 |
| Autoignition temperature | 255 °C |
| TSCA inventory status | TSCA listed |
| Hazard class | 3Eye Irrit. 2Flam. Liq. 2STOT SE 3 |
| Packing group | II |
| Customs code | 29159080 |
| Storage class | 3 - Flammable liquids |
| Hazardous substances data | 149-73-5(Hazardous Substances Data) |
| Toxicity | LD50 orally in Rabbit: 3130 mg/kg |
| REACH registrations | Active |
| Limited quantities | 1.0 L (0.3 gallon) (liquid) |
| Excepted quantities | Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml) |
Safety & Regulations
| GHS classification | This chemical does not meet GHS hazard criteria for 0.7% (2 of 294) of reports.DangerH225 (99.3%): Highly Flammable liquid and vapor [Danger Flammable liquids]P210, P233, P240, P241, P242, P243, P261, P264+P265, P271, P280, P303+P361+P353, P304+P340, P305+P351+P338, P319, P337+P317, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 294 reports by companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatory information | Chemical: Methane, trimethoxy-Methane, trimethoxy- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Methane, trimethoxy- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 08-09-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/12626Trimethyl orthoformate: Does not have an individual approval but may be used under an appropriate group standard |
| Fire potential | SLIGHT, WHEN EXPOSED TO HEAT OR FLAMECAN REACT WITH OXIDIZING MATERIALS. |
| Hazards summary | A skin, eye, and mucous membrane irritant[HSDB] Findings in lethal dose animal experiments include cyanosis, loss of muscle tone, and unresponsiveness. [ToxPlanet: IUCLID] Hydrolyzed by water producing methanolAn irritant[MSDSonline] See Methyl alcohol. |
| Hazard Classes and Categories | Flam. Liq. 2 (99.3%)Flammable liquids - Category 2 |
| Explosive Limits and Potential | SEE CHLOROFORM: UNPUBLISHED INFORMATION (1948). DURING ATTEMPTED PREPN OF TRIMETHYL ORTHOFORMATE, ADDITION OF SODIUM TO AN INADEQUATELY COOLED CHLOROFORM-METHANOL MIXTURE CAUSED VIOLENT EXPLOSION. |
| Protective Action Criteria (PAC) | 12 [mg/m3]130 [mg/m3]790 [mg/m3] |
| Adverse effects | Neurotoxin - Other CNS neurotoxin |
| Human Toxicity Excerpts | AN IRRITANT TO SKIN, EYES, & MUCOUS MEMBRANES. |
| Toxicity Data | LC50 (rat) = 40,000 mg/m3 |
| Personal protective equipment (PPE) | Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter |
| Water hazard class (WGK) | 1 |
| TSCA inventory status | TSCA listed |
| RTECS number | RM6650000 |
| UN transport number | UN 3272 3/PG 2 |
| Customs code | 29159080 |
| Toxicity | LD50 orally in Rabbit: 3130 mg/kg |
| Risk statements (R) | 11-36 |
| Signal word | Danger |
| GHS pictogram | GHS02,GHS07 |
| Hazard symbols | F,Xi |
| Safety statements (S) | 9-16-26-29 |
| Hazard class | 3Eye Irrit. 2Flam. Liq. 2STOT SE 3 |
| Storage class | 3 - Flammable liquids |
| Packing group | II |
| Target organs | Respiratory system |
| GHS hazard statements | H316-H319-H225 |
| Limited quantities | 1.0 L (0.3 gallon) (liquid) |
| Excepted quantities | Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml) |
| REACH registrations | Active |
| Autoignition temperature | 255 °C |
| GHS precautionary statements | P501-P240-P210-P233-P243-P241-P242-P264-P280-P370+P378-P337+P313-P305+P351+P338-P303+P361+P353-P332+P313-P403+P235 |
| Hazardous substances data | 149-73-5(Hazardous Substances Data) |
Applications & Uses
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 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 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 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.
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.