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122-51-0 molecular structure
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(diethoxymethoxy)ethane

ChemBase ID: 104743
Molecular Formular: C7H16O3
Molecular Mass: 148.20014
Monoisotopic Mass: 148.10994437
SMILES and InChIs

SMILES:
CCOC(OCC)OCC
Canonical SMILES:
CCOC(OCC)OCC
InChI:
InChI=1S/C7H16O3/c1-4-8-7(9-5-2)10-6-3/h7H,4-6H2,1-3H3
InChIKey:
GKASDNZWUGIAMG-UHFFFAOYSA-N

Cite this record

CBID:104743 http://www.chembase.cn/molecule-104743.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(diethoxymethoxy)ethane
IUPAC Traditional name
triethyl orthoformate
Synonyms
1,1,1-Triethoxymethane
Triethyl orthoformate
ETHYL ORTHOFORMATE
TRIETHYL ORTHOFORMATE
Triethoxymethane
Ethyl orthoformate
triethoxymethane
Orthoformic acid triethyl ester
1,1,1-三乙氧基甲烷
原甲酸三乙酯
CAS Number
122-51-0
EC Number
204-550-4
MDL Number
MFCD00009230
Beilstein Number
605384
Merck Index
146884
PubChem SID
24900342
24858320
162092273
24886840
PubChem CID
31214
Wikipedia Title
Triethyl_orthoformate

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
H Acceptors H Donor
LogD (pH = 5.5) 1.8138654  LogD (pH = 7.4) 1.8138654 
Log P 1.8138654  Molar Refractivity 39.5842 cm3
Polarizability 15.720697 Å3 Polar Surface Area 27.69 Å2
Rotatable Bonds Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Melting Point
-61°C expand Show data source
-61°C expand Show data source
-76 °C(lit.) expand Show data source
-76°C expand Show data source
Boiling Point
144°C expand Show data source
144-146°C expand Show data source
146 °C(lit.) expand Show data source
146°C expand Show data source
Flash Point
30°C(86°F) expand Show data source
35 °C expand Show data source
95 °F expand Show data source
Density
0.891 expand Show data source
0.891 g/mL expand Show data source
0.891 g/mL at 25 °C(lit.) expand Show data source
0.9 g/ml expand Show data source
0.90 g/ml expand Show data source
Refractive Index
1.3910 expand Show data source
n20/D 1.391 expand Show data source
n20/D 1.391(lit.) expand Show data source
Vapor Pressure
2.9 mmHg ( 20 °C) expand Show data source
Vapor Density
5.11 (vs air) expand Show data source
Storage Warning
Moisture Sensitive expand Show data source
RTECS
RM6475000 expand Show data source
European Hazard Symbols
Flammable Flammable (F) expand Show data source
Irritant Irritant (Xi) expand Show data source
UN Number
2524 expand Show data source
UN2524 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
1 expand Show data source
Hazard Class
3 expand Show data source
Packing Group
3 expand Show data source
III expand Show data source
Risk Statements
10 expand Show data source
10-36/37/38 expand Show data source
R:10-36/37 expand Show data source
Safety Statements
16-36/39-45 expand Show data source
26-37-60 expand Show data source
S:9-16-26 expand Show data source
TSCA Listed
expand Show data source
GHS Pictograms
GHS02 expand Show data source
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H226 expand Show data source
H226-H315-H319-H335 expand Show data source
GHS Precautionary statements
P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A expand Show data source
Personal Protective Equipment
Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter expand Show data source
RID/ADR
UN 2524 3/PG 3 expand Show data source
Purity
≥98.0% (GC) expand Show data source
97% expand Show data source
98% expand Show data source
Grade
anhydrous expand Show data source
purum expand Show data source
reagent grade expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Evaporation Residue
<0.0005% expand Show data source
Impurities
<0.003% water expand Show data source
<0.005% water(100 mL pkg) expand Show data source
Linear Formula
CH(OC2H5)3 expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich
MP Biomedicals - 05209901 external link
MP Biomedicals Rare Chemical collection
MP Biomedicals - 02157013 external link
(1,1′,1′′-[Methylidynetris(oxyl)]-tris[ethanel])
1 ml = approx. 0.90 g
Sigma Aldrich - T60453 external link
Packaging
1 L in glass bottle
20 L in steel drum
500 mL in glass bottle
Sigma Aldrich - 304050 external link
Packaging
1, 2 L in Sure/Seal™
100 mL in Sure/Seal™

REFERENCES

REFERENCES

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  • • For further reactions of alkyl orthoformates, see Trimethyl orthoformate, A13760.
  • • Acid-catalyzed reaction with an arylamine gives the N-ethoxymethylene derivative (imidic ester); see, e.g.: Org. Synth. Coll., 4, 464 (1963); reduction (NaBH4) gives the monomethyl amine: Synthesis, 55 (1974).
  • • Due to their intrinsic dehydrating property, orthoformates are convenient reagents for acetalization of carbonyl compounds, under acid catalysis, e.g. tosic acid: J. Am. Chem. Soc., 60, 1905 (1938); J. Org. Chem., 20, 1695 (1955), or acidic ion-exchange resin: Synthesis, 348 (1974). Selective catalysis with NBS has been found to give high yields of acetals under almost neutral conditions: Synlett, 1456 (1999).
  • • In the presence of BF3 etherate, is a source of the diethoxycarbenium ion: Synth. Commun., 19, 2307 (1989), a selective alkylating agent and a useful intermediate for the diethoxymethylenation of ketones, to give protected ?-ketoaldehydes: J. Org. Chem., 46, 2557 (1981). For a similar reaction with enamines to give the same products, see: Chem. Lett., 1307 (1982); Bull. Chem. Soc. Jpn., 57, 1876 (1984).
  • • Orthoformates have also found use in the electrophilic formylation of activated aromatic species, e.g.: phenols (in the presence of AlCl3): Chem. Ber., 96, 308 (1963); pyrrole derivatives (with TFA): Austral. J. Chem., 25, 1979 (1972).
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PATENTS

PATENTS

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INTERNET

INTERNET

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