305472

Trimethyl orthoformate

anhydrous, 99.8%

• Synonym(s): TMOF, Trimethoxymethane
• Linear Formula: CH(OCH₃)₃
• CAS Number: 149-73-5
• Molecular Weight: 106.12
• Beilstein: 969215
• EC Number: 205-745-7
• MDL number: MFCD00008483
• UNSPSC Code: 12352112
• eCl@ss: 39021015
• PubChem Substance ID: 24858434
• NACRES: NA.22

Properties

• grade: anhydrous
• Quality Level: 200
• vapor density: 3.67 (vs air)
• vapor pressure: 23.5 mmHg ( 20 °C); 40 mmHg ( 30 °C); 57 mmHg ( 40 °C)
• Assay: 99.8%
• form: liquid
• expl. lim.: 5.1 %
• impurities: <0.002% water; <0.005% water (100 mL pkg)
• evapn. residue: <0.0005%
• refractive index: n20/D 1.379 (lit.)
• bp: 101-102 °C (lit.)
• density: 0.97 g/mL at 25 °C (lit.)
• functional group: ether
• SMILES string: COC(OC)OC
• InChI: 1S/C4H10O3/c1-5-4(6-2)7-3/h4H,1-3H3
• InChI key: PYOKUURKVVELLB-UHFFFAOYSA-N

Description

General description

Trimethyl orthoformate is a commonly used reagent in organic synthesis for the preparation of useful building blocks. It 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.

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.

Safety Information

• Pictograms: GHS02,GHS07
• Signal Word: Danger
• Hazard Statements: H225,H319,H335
• Precautionary Statements: P210 - P233 - P240 - P241 - P242 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Flam. Liq. 2 - STOT SE 3
• Target Organs: Respiratory system
• Storage Class Code: 3 - Flammable liquids
• WGK: WGK 1
• Flash Point(F): 55.4 °F - closed cup
• Flash Point(C): 13 °C - closed cup
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves