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Tetraethyl orthocarbonate

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Tetraethyl orthocarbonate Basic information

Product Name:
Tetraethyl orthocarbonate
Synonyms:
  • ORTHOCARBONIC ACID TETRAETHYL ESTER
  • TETRAETHOXYMETHANE
  • TETRAETHYL ORTHOCARBONATE
  • 1-(Triethoxymethoxy)ethane
  • 1,1’,1’’,1’’’-[methanetetrayltetrakis(oxy)]tetrakis-ethan
  • Tetraehtylorthocarbonate
  • [methanetetrayltetrakis(oxy)]tetrakis-
  • Ethane, 1,1‘,1‘‘,1‘‘‘-
CAS:
78-09-1
MF:
C9H20O4
MW:
192.25
EINECS:
201-082-2
Product Categories:
  • Acetals/Ketals/Ortho Esters
  • Organic Building Blocks
  • Oxygen Compounds
  • 78-09-1
Mol File:
78-09-1.mol
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Tetraethyl orthocarbonate Chemical Properties

Melting point:
222 °C
Boiling point:
159 °C (lit.)
Density 
0.919 g/mL at 25 °C (lit.)
refractive index 
n20/D 1.392(lit.)
Flash point:
127 °F
storage temp. 
Inert atmosphere,Room Temperature
solubility 
soluble in Chloroform, Methanol
form 
clear liquid
Specific Gravity
0.919
color 
Colorless to Almost colorless
Water Solubility 
Insoluble
Sensitive 
Moisture Sensitive
BRN 
1747401
CAS DataBase Reference
78-09-1(CAS DataBase Reference)
NIST Chemistry Reference
Ethane, 1,1',1'',1'''-[methanetetrayltetrakis(oxy)]tetrakis-(78-09-1)
EPA Substance Registry System
Ethane, 1,1',1'',1'''-[methanetetrayltetrakis(oxy)]tetrakis- (78-09-1)
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Safety Information

Hazard Codes 
Xi,F
Risk Statements 
10-36/37/38
Safety Statements 
37/39-26-16-36-24/25
RIDADR 
UN 3272 3/PG 3
WGK Germany 
3
21
HazardClass 
3
PackingGroup 
III
HS Code 
29209010

MSDS

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Tetraethyl orthocarbonate Usage And Synthesis

Chemical Properties

clear colorless liquid

Uses

Tetraethyl Orthocarbonate is used in the synthesis of chemokine receptor-5 inhibitors against HIV-1, benzobisoxazoles and in the preparation of organic semiconductors. It is also employed in the synthesis of 2,7-dimethylene-1,4,6,9-tetraoxaspiro[4,4]nonane and in the synthesis of cross linked poly(orthocarbonate)s used as organic solvent absorbent.

Purification Methods

Likely impurities are hydrolysis products. Shake the orthocarbonate with brine (saturated NaCl, dilute with a little Et2O if amount of material is small) and dry (MgSO4). The organic layer is filtered off and evaporated, and the residue is distilled through a helices packed fractionating column with a total reflux partial take-off head. All distillations can be done at atmospheric pressure in an inert atmosphere (e.g. N2). [Roberts & McMahon Org Synth Coll Vol IV 457 1963, Connolly & Dyson J Chem Soc 828 1937, Tieckelmann & Post J Org Chem 13 266 1948, for review see Kantlehner et al. Justus Liebigs Ann Chem 507 207 1982, Beilstein 3 IV 6.]

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