Skip to Content
Merck
CN

305472

Trimethyl orthoformate

anhydrous, 99.8%

Synonym(s):

TMOF, Trimethoxymethane

Sign In to View Organizational & Contract Pricing.

Select a Size

About This Item

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

Key Documents

View All Documentation
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

Product Name

Trimethyl orthoformate, anhydrous, 99.8%

impurities

<0.005% water (100 mL pkg)
<0.002% water

InChI key

PYOKUURKVVELLB-UHFFFAOYSA-N

InChI

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

SMILES string

COC(OC)OC

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%

form

liquid

expl. lim.

5.1 %

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.)

functional group

ether

Quality Level

200

Looking for similar products? Visit Product Comparison Guide

Related Categories

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.

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.

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

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

Regulatory Information

危险化学品
This item has

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
SHBT5397
SHBS6760
SHBR8057
SHBS1423
SHBS1014

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Alkyl Orthoformate: A Versatile Reagent in Organic Synthesis
Frizzo CP
Synlett, 2009(06), 1019-1020 (2009)
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)
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)
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 new method for the esterification of sulfonic-acids
Padmapriya, AA and Just, G and Lewis, NG
Synthetic Communications, 15, 1057-1062 (1985)
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service