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305472

Sigma-Aldrich

Trimethyl orthoformate

anhydrous, 99.8%

Synonym(s):

TMOF, Trimethoxymethane

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About This Item

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

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.)

SMILES string

COC(OC)OC

InChI

1S/C4H10O3/c1-5-4(6-2)7-3/h4H,1-3H3

InChI key

PYOKUURKVVELLB-UHFFFAOYSA-N

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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.

pictograms

FlameExclamation mark
GHS02,GHS07

signalword

Danger

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

3 - Flammable liquids

wgk_germany

WGK 1

flash_point_f

55.4 °F - closed cup

flash_point_c

13 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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A convenient one pot procedure for N-methylation of aromatic amines using trimethyl orthoformate
Padmanabhan, Seetharamaiyer and Reddy, N Laxma and Durant, Graham J
Synthetic Communications, 27(4), 691-699 (1997)
Regiochemistry of the Reaction of 2-Acylcyclohexanones with Trimethyl Orthoformate: A Convenient One-Pot Method to Obtain 7, 7-Dimethoxy Alkanoate Methyl Esters
Martins MAP, et al.
Synlett, 6(06), 789-791 (1999)
Alkyl Orthoformate: A Versatile Reagent in Organic Synthesis
Frizzo CP
Synlett, 2009(06), 1019-1020 (2009)
Tetrafluoroboric acid adsorbed on silica gel as a reusable heterogeneous dual-purpose catalyst for conversion of aldehydes/ketones into acetals/ketals and back again
Kumar D, etal.
Synthesis, 2008(08), 1249-1256 (2008)
Efficient pinacol rearrangement mediated by trimethyl orthoformate
Kita Y, et al.
Tetrahedron Letters, 38(48), 8315-8318 (1997)
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