Compound: Triethyl orthoformate
SMILES: O(C(OCC)OCC)CC
InChIKey: GKASDNZWUGIAMG-UHFFFAOYSA-N
Synonyms: Triethyl orthoformate, 122-51-0, Triethoxymethane, ETHYL ORTHOFORMATE, Aethon, Orthoformic acid triethyl ester, Methane, triethoxy-, Ethyl formate(ortho), Ethane, 1,1',1''-[methylidynetris(oxy)]tris-, Orthomravencan ethylnaty, Orthoformic acid, triethyl ester, Orthoformic acid ethyl ester, 108055-42-1, Ethylester kyseliny orthomravenci, NSC 5289, Orthoformic acid, ethyl ester, UN2524, Orthomravencan ethylnaty [Czech], Triethylester kyseliny orthomravenci, Orthoformic acid ethyl ester (VAN), EINECS 204-550-4, AETHONE, BRN 0605384, Ethane, 1,1',1''-(methylidynetris(oxy))tris-, Ethylester kyseliny orthomravenci [Czech], DTXSID8041957, AI3-24333, 355LRR361Q, Triethylester kyseliny orthomravenci [Czech], 1,1',1'-(Methylidynetris(oxy))tris(ethane), NSC-5289, OFE (ETHER), 1,1',1''-[methanetriyltris(oxy)]triethane, DTXCID6021957, 1,1',1''-(Methylidynetris(oxy))tris(ethane), EC 204-550-4, 4-02-00-00025 (Beilstein Handbook Reference), ETHYL ORTHOFORMATE [WHO-DD], UN-2524, ORTHOFORMIC ACID TRIETHYL ESTER [MI], 1,1',1''-(methanetriyltris(oxy))triethane, triethoxymethan, Ethylorthoformiat, Methane, triethoxy, Triethylorthoformiat, Triethyl orthoformiate, Orthoformiate d ethyle, 1,1',1''triethane, RefChem:596352, Orthoameisensaeuretriethylester, 1,1',1"(Methylidynetris(oxy))tris(ethane), Ethane, 1,1',1''(methylidynetris(oxy))tris, 204-550-4, InChI=1/C7H16O3/c1-4-8-7(9-5-2)10-6-3/h7H,4-6H2,1-3H, diethoxymethoxyethane, (diethoxymethoxy)ethane, triethylorthoformate, Triethoxmethane, 1,1,1-Triethoxymethane, triethoxy methane, Triethyl orthoformate-d1, MFCD00009230, Triethyl ortho formate, UNII-355LRR361Q, ethylorthoformiate, 1,1',1''-[Methylidyne-tris(oxy)]tris-Ethane; Orthoformic Acid Triethyl Ester;, tri(ethoxy)methane, triethyl-o-formate, triethy orthoformate, triethyl orthoformat, trietyl orthoformate, triethylorthoforrnate, triethy lorthoformate, triethyl-orthoformate, diethoxymethoxy ethane, diethoxymethoxy-ethane, triethyl orthoforrnate, tri-ethyl orthoformate, triethyl ortho-formate, (diethoxymethoxy) ethane, (EtO)3CH, 1-(Diethoxymethoxy)ethane, CH(OEt)3, HC(OEt)3, CH(OCH2CH3)3, SCHEMBL18928, 1-(Diethoxymethoxy)ethane #, Orthoformic acid triethylester, orthoformic acidtriethyl ester, SCHEMBL618158, (C2H5O)3CH, CH(OC2H5)3, SCHEMBL7066332, CHEMBL1476236, ortho-formic acid triethyl-ester, WLN: 2OYO2 & O2, NSC5289, Triethyl ester of Orthoformic acid, STR00668, Tox21_301314, BBL027745, STL197942, AKOS000120197, FT02309, Triethyl orthoformate, anhydrous, 98%, UN 2524, NCGC00166027-01, NCGC00255741-01, CAS-122-51-0, Triethyl orthoformate, analytical standard, Triethyl orthoformate, reagent grade, 98%, 1,1',1"-[methylidynetris(oxy)]trisethane, Ethane,1',1''-[methylidynetris(oxy)]tris-, NS00002726, O0066, EN300-19201, Ethyl orthoformate [UN2524]  [Flammable liquid], F044717, Q421330, doi:10.14272/GKASDNZWUGIAMG-UHFFFAOYSA-N.1, Triethyl Orthoformate(Discontinued,See C4X-1720170), F1908-0165
Theoretical properties:
molecular_formula: C7H16O3
molecular_weight: 148.20 g/mol
exact_mass: 148.109944368 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 6
heavy_atom_count: 10
topological_polar_surface_area: 27.7 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
vapor_pressure: 3.86 [mmHg]
Descriptions:
chembl: Unnamed Compound is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Triethyl orthoformate is an organic compound with the formula HC(OC2H5)3.  This colorless volatile liquid, the ortho ester of formic acid, is commercially available.  The industrial synthesis is from hydrogen cyanide and ethanol.
It may also be prepared from the reaction of sodium ethoxide, formed in-situ from sodium and absolute ethanol, and chloroform:

CHCl3 + 3 Na + 3 EtOH → HC(OEt)3 + 3⁄2 H2 + 3 NaCl
Triethyl orthoformate is used in the Bodroux–Chichibabin aldehyde synthesis, for example:

RMgBr  +  HC(OC2H5)3   →   RC(H)(OC2H5)2  +  MgBr(OC2H5)
RC(H)(OC2H5)2  +  H2O   →    RCHO  +  2 C2H5OH
In coordination chemistry, it is used to convert metal aquo complexes to the corresponding ethanol complexes:

[Ni(H2O)6](BF4)2  +  6  HC(OC2H5)3   →  [Ni(C2H5OH)6](BF4)2  +  6 HC(O)(OC2H5)  +  6  HOC2H5
Triethyl orthoformate (TEOF) is an excellent reagent for converting compatible carboxylic acids to ethyl esters. Such carboxylic acids, refluxed neat in excess TEOF until low-boilers cease evolution, are quantitatively converted to the ethyl esters, without need for extraneous catalysis.  Alternatively, added to ordinary esterifications using catalytic acid and ethanol, TEOF helps drive esterification to completion by converting the byproduct water formed to ethanol and ethyl formate.