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.)

Flash point:

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

• Language:English Provider:Methyl orthoformate
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

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. Slightly soluble in water, miscible with alcohol and oils.
Very diffusive, ethereal, pungent or nauseating odor, pleasant in dilution, slightly wineyfruity, Brandy-like.
Sweet taste in concentrations below 100 ppm. Barely perceptible at 10 ppm.

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.

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(149-73-5)Related Product Information

• Methyl acetate
• 5-Chlorovaleric acid
• Pralmorelin
• Methyl anthranilate
• 4-(Diethylamino)salicylaldehyde
• Trimethyl phosphate
• Trimethyl phosphonoacetate
• METSULFURON METHYL
• Methylparaben
• Kresoxim-methyl
• Trimethyl borate
• Methyl benzoate
• Methyl salicylate
• Diphenolic acid
• Methyl carbamate
• Methyl formate
• Thiophanate-methyl
• Tribenuron methyl