305472
Trimethyl orthoformate
anhydrous, 99.8%
Synonym(s):
TMOF, Trimethoxymethane
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About This Item
Linear Formula:
CH(OCH3)3
CAS Number:
Molecular Weight:
106.12
NACRES:
NA.22
PubChem Substance ID:
eCl@ss:
39021015
UNSPSC Code:
12352112
EC Number:
205-745-7
MDL number:
Beilstein/REAXYS Number:
969215
Assay:
99.8%
Form:
liquid
grade
anhydrous
Quality Level
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
<0.005% water (100 mL pkg), <0.002% water
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
SMILES string
COC(OC)OC
InChI
1S/C4H10O3/c1-5-4(6-2)7-3/h4H,1-3H3
InChI key
PYOKUURKVVELLB-UHFFFAOYSA-N
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.
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signalword
Danger
hcodes
Hazard Classifications
Eye Irrit. 2 - Flam. Liq. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
3 - Flammable liquids
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
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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)
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)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 305472-2L | 04061826668139 |
| 305472-100ML | 04061826667866 |
| 305472-1L | 04061837522451 |