305472

Sigma-Aldrich

Trimethyl orthoformate

anhydrous, 99.8%

Synonym(s):
TMOF, Trimethoxymethane
Linear Formula:
CH(OCH3)3
CAS Number:
Molecular Weight:
106.12
Beilstein/REAXYS Number:
969215
EC Number:
MDL number:
eCl@ss:
39021015
PubChem Substance ID:
Pricing and availability is not currently available.

Quality Level

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

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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.

Packaging

1, 2 L in Sure/Seal™
100 mL in Sure/Seal™

Pictograms

FlameExclamation mark

Signal Word

Danger

Hazard Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Hazard Codes

F,Xi

Risk Statement

11-36

Safety Statement

9-16-26

RIDADR

UN 3272 3 / PGII

WGK Germany

WGK 1

Flash Point(F)

55.4 °F - closed cup

Flash Point(C)

13 °C - closed cup

Indium triflate-catalyzed one-pot synthesis of 1-substituted-1H-1, 2, 3, 4-tetrazoles under solvent-free conditions
Kundu, Dhiman and Majee, Adinath and Hajra, Alakananda
Tetrahedron Letters, 50(22), 2668-2670 (2009)
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)
A new method for the esterification of sulfonic-acids
Padmapriya, AA and Just, G and Lewis, NG
Synthetic Communications, 15, 1057-1062 (1985)
Synthesis of 2?, 3?-dideoxyuridine
FU Y, et al.
Journal of Non-Newtonian Fluid Mechanics, (4), 13-13 (2013)
Efficient pinacol rearrangement mediated by trimethyl orthoformate
Kita Y, et al.
Tetrahedron Letters, 38(48), 8315-8318 (1997)

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