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149-73-5 - Trimethyl orthoformate, 99% - Methyl orthoformate - Orthoformic acid trimethyl ester - A13760 - Alfa Aesar

A13760 Trimethyl orthoformate, 99%

CAS Number
149-73-5
Synonyms
Methyl orthoformate
Orthoformic acid trimethyl ester

Size Price ($) Quantity Availability
100ml 19.98
500ml 43.36
2500ml 139.05
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Trimethyl orthoformate, 99%

MDL
MFCD00008483
EINECS
205-745-7

Chemical Properties

Formula
HC(OCH3)3
Formula Weight
106.12
Melting point
-53°
Boiling Point
101-102°
Flash Point
15°(59°F)
Density
0.968
Refractive Index
1.3790
Sensitivity
Moisture Sensitive
Solubility
Miscible with ether, alcohol and benzene.

Applications

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.

Notes

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

Literature References

Reagent for the acid-catalyzed conversion of ketones to their methyl enol ethers in good yield: Synthesis, 38 (1974). For an example, see: Org. Synth. Coll., 8, 357 (1993).

Protects the cis-2,3-diol system of ribonucleosides as their methoxymethylene acetals (cyclic orthoformates), readily hydrolyzed by mild acid: Synthesis, 408 (1985).

In the presence of HCl, is an alternative to formic acid in the synthesis of benzoxazoles from ortho-amino phenols: Org. Prep. Proced. Int., 22, 613 (1990).

For further reactions of alkyl orthoformates, see Triethyl­ orthoformate, A13587.

Nemeth, I.; Kiss-Szikszai, A.; Illyes, T. Z.; Mandi, A.; Komaromi, I.; Kurtan, T.; Antus, S. Oxidative Rearrangement of Flavanones with Thallium(III) Nitrate, Lead Tetraacetate and Hypervalent Iodines in Trimethyl Orthoformate and Perchloric or Sulfuric Acid. Z. Naturforsch. B Chem. Sci. 2012, 67B (12), 1289-1296.

Pospech, J.; Lennox, A. J.; Beller, M. Rhodium-catalysed alkoxylation/acetalization of diazo compounds: one-step synthesis of highly functionalised quaternary carbon centres. Chem. Commun. 2015, 51 (77), 14505-14508.

GHS Hazard and Precautionary Statements

Hazard Statements: H225-H315-H319-H335

Highly flammable liquid and vapour. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Precautionary Statements: P210-P261-P280-P240-P303+P361+P353-P305+P351+P338-P304+P340-P362-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. Ground/bond container and receiving equipment. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Take off contaminated clothing and wash before reuse. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Merck
14,6884
Beilstein
969215
Hazard Class
3
Packing Group
II
Harmonized Tariff Code
2915.90
TSCA
Yes
RTECS
RM6650000

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