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305472 Sigma-Aldrich

Trimethyl orthoformate

anhydrous, 99.8%

Synonym: TMOF, Trimethoxymethane

  • CAS Number 149-73-5

  • Linear Formula CH(OCH3)3

  • Molecular Weight 106.12

  •  Beilstein/REAXYS Number 969215

  •  EC Number 205-745-7

  •  MDL number MFCD00008483

  •  eCl@ss 39021015

  •  PubChem Substance ID 24858434

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Properties

Related Categories Chemical Synthesis, Other Protecting and Derivatizing Reagents, Protecting and Derivatizing Reagents, Protection and Derivatization, Solvent Bottles,
Quality Level   200
grade   anhydrous
vapor density   3.67 (vs air)
vapor pressure   23.5 mmHg ( 20 °C)
  40 mmHg ( 30 °C)
  57 mmHg ( 40 °C)
assay   99.8%
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.)
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.

Packaging

1, 2 L in Sure/Seal™

100 mL in Sure/Seal™

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
RIDADR 
UN 3272 3 / PGII
WGK Germany 
WGK 1
RTECS 
RM6650000
Flash Point(F) 
55.4 °F - closed cup
Flash Point(C) 
13 °C - closed cup

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

Pressure-Temperature Calculator for Solvents

*Calculations provide estimated results based on Antoine's Coefficients and their associated temperature range values. Antoine's Coefficients were obtained from the National Institute of Standards an...

Peer-Reviewed Papers
15

References

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