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Merck
CN

304050

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
UNSPSC Code:
12352001
NACRES:
NA.21
PubChem Substance ID:
24858320
EC Number:
204-550-4
Beilstein/REAXYS Number:
605384
MDL number:
MFCD00009230
Assay:
98%
Grade:
anhydrous
Bp:
146 °C (lit.)
Vapor pressure:
2.9 mmHg ( 20 °C)

Key Documents

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Product Name

Triethyl orthoformate, anhydrous, 98%

InChI key

GKASDNZWUGIAMG-UHFFFAOYSA-N

InChI

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

SMILES string

CCOC(OCC)OCC

grade

anhydrous

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.)

Quality Level

100

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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

signalword

Warning

hcodes

H226

Hazard Classifications

Flam. Liq. 3

Storage Class

3 - Flammable liquids

wgk

WGK 1

flash_point_f

95.0 °F - closed cup

flash_point_c

35 °C - closed cup

ppe

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

Regulatory Information

危险化学品
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Certificates of Analysis (COA)

Lot/Batch Number
SHBT5345
SHBR9920
SHBP8214
SHBM8966
SHBM3189

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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)
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)
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)
Synthesis of 8-demethyl-8-hydroxy-5-deazariboflavins
Ashton WT and Brown RD
Journal of Heterocyclic Chemistry, 17(8), 1709-1712 (1980)
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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