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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
Assay:
98%
bp:
146 °C (lit.)
vapor pressure:
2.9 mmHg ( 20 °C)
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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.[1]
  • 5-Nitropyridines via cyclocondensation with nitroacetone and different enamines.[2]
  • 3-Aryl-4(3H)-quinazolinones by reacting with anthranilic acid via heterocyclization catalyzed by concentrated sulfuric acid.[3]

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

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Certificates of Analysis (COA)

Lot/Batch Number
SHBR9920
SHBP8214
SHBM8966
SHBM3189
SHBM3187

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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)
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
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)
Adenine complexes with 3d metal perchlorates from ethanol-triethyl orthoformate.
Speca AN, et al.
Inorgorganica Chimica Acta, 37, L551-L554 (1979)
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Questions

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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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