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Safety Information

304050

Sigma-Aldrich

Triethyl orthoformate

anhydrous, 98%

Synonym(s):

Diethoxymethoxyethane, 1,1,1-Triethoxymethane

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About This Item

Linear Formula:
CH(OC2H5)3
CAS Number:
122-51-0
Molecular Weight:
148.20
Beilstein:
605384
EC Number:
204-550-4
MDL number:
MFCD00009230
UNSPSC Code:
12352001
PubChem Substance ID:
24858320
NACRES:
NA.21

grade

anhydrous

Quality Level

100

vapor density

5.11 (vs air)

vapor pressure

2.9 mmHg ( 20 °C)

Assay

98%

form

liquid

impurities

<0.003% water
<0.005% water (100 mL pkg)

evapn. residue

<0.0005%

refractive index

n20/D 1.391 (lit.)

bp

146 °C (lit.)

mp

−76 °C (lit.)

density

0.891 g/mL at 25 °C (lit.)

SMILES string

CCOC(OCC)OCC

InChI

1S/C7H16O3/c1-4-8-7(9-5-2)10-6-3/h7H,4-6H2,1-3H3

InChI key

GKASDNZWUGIAMG-UHFFFAOYSA-N

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Application

Triethyl orthoformate may be used to synthesize:
  • Formyl ferrocene by reacting with ferrocene in the presence of aluminium chloride.
  • 5-Nitropyridines via cyclocondensation with nitroacetone and different enamines.
  • 3-Aryl-4(3H)-quinazolinones by reacting with anthranilic acid via heterocyclization catalyzed by concentrated sulfuric acid.

Pictograms

Flame
GHS02

Signal Word

Warning

Hazard Statements

H226

Hazard Classifications

Flam. Liq. 3

Storage Class Code

3 - Flammable liquids

WGK

WGK 1

Flash Point(F)

95.0 °F - closed cup

Flash Point(C)

35 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 4: Flammable liquids
Type 2 petroleums
Hazardous rank III
Water insoluble liquid

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

304050-VAR:
304050-BULK:
304050-1L:
304050-2L:
304050-100ML:
304050-6X1L:

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Certificates of Analysis (COA)

Lot/Batch Number
SHBR9920
SHBP8214
SHBM8966
SHBM3189
SHBM3187

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A new convenient method for the synthesis of formyl ferrocene with triethyl orthoformate and A1C13
Tang J, et al.
Synthetic Communications, 30(9), 1657-1660 (2000)
One-pot synthesis of 5-nitropyridines by the cyclocondensation of nitroacetone, triethyl orthoformate and enamines
Sagitullina GP, et al.
Mendeleev Communications, 19(3), 155-156 (2009)
Adenine complexes with 3d metal perchlorates from ethanol-triethyl orthoformate.
Speca AN, et al.
Inorgorganica Chimica Acta, 37, L551-L554 (1979)
Synthesis of 3-Aryl-4 (3 H)-quinazolinones from Anthranilic Acids and Triethyl Orthoformate
Cao SL, et al.
Synthetic Communications, 38(13), 2227-2236 (2008)
Mark S Kerr et al.
The Journal of organic chemistry, 70(14), 5725-5728 (2005-07-02)
[reaction: see text] The promising utility of triazolyl N-heterocyclic carbene catalysts in umpolung aldehyde chemistry requires a straightforward reliable synthesis from readily available materials. Herein, we describe the synthesis of a variety of triazolyl N-heterocyclic carbene precursors. The reactions commence
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