Triethyl orthoformate

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Structural formula
Structural formula of triethyl orthoformate
General
Surname Triethyl orthoformate
other names
  • Triethoxymethane
  • Triethyl orthoformate
Molecular formula C 7 H 16 O 3
Brief description

Flammable, moisture-sensitive, colorless liquid with an aromatic odor

External identifiers / databases
CAS number 122-51-0
EC number 204-550-4
ECHA InfoCard 100.004.138
PubChem 31214
Wikidata Q421330
properties
Molar mass 148.20 g mol −1
Physical state

liquid

density

0.895 g cm −3

Melting point

−76.1 ° C

boiling point

146 ° C

Vapor pressure

4 hPa (20 ° C)

solubility

Slightly soluble in water (1.35 g l −1
slow decomposition
at 20 ° C)

Refractive index

1.3922 (20 ° C)

safety instructions
GHS labeling of hazardous substances
02 - Highly / extremely flammable

Caution

H and P phrases H: 226
P: 210
Toxicological data

7060 mg kg −1 ( LD 50 ,  rat ,  oral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Triethyl orthoformate is a chemical compound from the group of orthoesters . It is an ester of the hypothetical orthoformic acid HC (OH) 3 .

Extraction and presentation

In addition to the esterification of formic acid, triethyl orthoformate can be obtained by reacting sodium ethanolate and chloroform :

Preparation of triethyl orthoformate from sodium ethanolate and chloroform

properties

Triethyl orthoformate is a flammable, moisture-sensitive, colorless liquid with an aromatic odor.

use

Triethyl orthoformate is part of the Bodroux-Chichibabin-aldehyde synthesis , for example:

Bodroux-Chichibabin aldehyde synthesis of n-hexaldehyde.png

safety instructions

Triethyl orthoformate forms highly flammable vapor-air mixtures. The compound has a flash point of 34 ° C. The explosion range is between 0.85% by volume (52 g / m 3 ) as the lower explosion limit (LEL) and 27.2% by volume (1676 g / m 3 ) as the upper explosion limit (UEL). The ignition temperature is 188 ° C. The substance therefore falls into temperature class T4.

Related links

Individual evidence

  1. ↑ a b c d e f g h i j k l m n Entry on triethyl orthoformate in the GESTIS substance database of the IFA , accessed on February 2, 2016(JavaScript required) .
  2. ↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-498.
  3. ↑ WE Kaufmann and EE Dreger: Ethyl orthoformate In: Organic Syntheses . 5, 1925, p. 55, doi : 10.15227 / orgsyn.005.0055 ; Coll. Vol. 1, 1941, p. 258 ( PDF ).
  4. ^ G. Bryant Bachman: n-Hexaldehyde In: Organic Syntheses . 16, 1936, p. 41, doi : 10.15227 / orgsyn.016.0041 ; Coll. Vol. 2, 1943, p. 323 ( PDF ).
  5. ^ A b E. Brandes, W. Möller: Safety-related parameters - Volume 1: Flammable liquids and gases , Wirtschaftsverlag NW - Verlag für neue Wissenschaft GmbH, Bremerhaven 2003.