Triethyl orthoformate

Base Information

• Chemical Name: Triethyl orthoformate
• CAS No.: 122-51-0
• Molecular Formula: C7H16O3
• Molecular Weight: 148.202
• Hs Code.: 29159080
• European Community (EC) Number: 204-550-4
• NSC Number: 5289
• UN Number: 2524
• UNII: 355LRR361Q
• DSSTox Substance ID: DTXSID8041957
• Nikkaji Number: J5.533F
• Wikipedia: Triethyl_orthoformate
• Wikidata: Q421330
• Metabolomics Workbench ID: 123528
• ChEMBL ID: CHEMBL1476236
• Mol file: 122-51-0.mol

Synonyms:Triethyl orthoformate;122-51-0;Triethoxymethane;ETHYL ORTHOFORMATE;diethoxymethoxyethane;Aethon;Methane, triethoxy-;Ethyl formate(ortho);Orthoformic acid triethyl ester;(diethoxymethoxy)ethane;Ethane, 1,1',1''-[methylidynetris(oxy)]tris-;Orthomravencan ethylnaty;triethylorthoformate;Orthoformic acid, triethyl ester;Orthoformic acid ethyl ester;108055-42-1;Triethoxmethane;Ethylester kyseliny orthomravenci;1,1,1-Triethoxymethane;triethoxy methane;NSC 5289;UN2524;Orthoformic acid, ethyl ester;Orthomravencan ethylnaty [Czech];Triethylester kyseliny orthomravenci;Orthoformic acid ethyl ester (VAN);Triethyl orthoformate-d1;EINECS 204-550-4;Ethane, 1,1',1''-(methylidynetris(oxy))tris-;BRN 0605384;Ethylester kyseliny orthomravenci [Czech];UNII-355LRR361Q;AI3-24333;Triethylester kyseliny orthomravenci [Czech];DTXSID8041957;1,1',1'-(Methylidynetris(oxy))tris(ethane);355LRR361Q;NSC-5289;1,1',1''-[methanetriyltris(oxy)]triethane;1,1',1''-(Methylidynetris(oxy))tris(ethane);EC 204-550-4;26387-53-1;4-02-00-00025 (Beilstein Handbook Reference);Triethyl ortho formate;ethylorthoformiate;tri(ethoxy)methane;triethyl-o-formate;triethy orthoformate;triethyl orthoformat;trietyl orthoformate;triethylorthoforrnate;triethy lorthoformate;triethyl-orthoformate;Triethyl orthofromate;MFCD00009230;AETHONE;diethoxymethoxy ethane;diethoxymethoxy-ethane;triethyl orthoforrnate;tri-ethyl orthoformate;triethyl ortho-formate;(diethoxymethoxy) ethane;Orthoformiate de trithyle;OFE (ETHER);(EtO)3CH;1-(Diethoxymethoxy)ethane;CH(OEt)3;HC(OEt)3;CH(OCH2CH3)3;SCHEMBL18928;1-(Diethoxymethoxy)ethane #;Orthoformic acid triethylester;orthoformic acidtriethyl ester;(C2H5O)3CH;CH(OC2H5)3;CHEMBL1476236;DTXCID6021957;ortho-formic acid triethyl-ester;WLN: 2OYO2 & O2;NSC5289;Triethyl ester of Orthoformic acid;AMY40134;ETHYL ORTHOFORMATE [WHO-DD];STR00668;Tox21_301314;BBL027745;NA2524;STL197942;AKOS000120197;Triethyl orthoformate, anhydrous, 98%;UN 2524;UN-2524;NCGC00166027-01;NCGC00255741-01;CAS-122-51-0;LS-98476;Triethyl orthoformate, analytical standard;Triethyl orthoformate, reagent grade, 98%;1,1',1"-[methylidynetris(oxy)]trisethane;Ethane,1',1''-[methylidynetris(oxy)]tris-;O0066;ORTHOFORMIC ACID TRIETHYL ESTER [MI];EN300-19201;Ethyl orthoformate [UN2524] [Flammable liquid];Ethyl orthoformate [UN2524] [Flammable liquid];Q421330;Etano, 1,1', 1''-[metilidinetris (oxi)] tris-;Q-201870;ETHANE, 1,1',1"-[METHYLIDYNETRIS(OXY)]TRIS-;ETHANE, 1,1',1"[METHYLIDYNETRIS(OXY)]TRIS-;F1908-0165

Chemical Property of Triethyl orthoformate

Chemical Property:

• Appearance/Colour: colorless liquid, with spicy odor
• Vapor Pressure: 2.9 mm Hg ( 20 °C)
• Melting Point: -76 °C(lit.)
• Refractive Index: n20/D 1.391(lit.)
• Boiling Point: 142.5 °C at 760 mmHg
• Flash Point: 30 °C
• PSA: 27.69000
• Density: 0.891 g/cm³
• LogP: 1.37950
• Storage Temp.: Flammables area
• Sensitive.: Moisture Sensitive
• Water Solubility.: 1.35 g/L
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 148.109944368
• Heavy Atom Count: 10
• Complexity: 51.6
• Transport DOT Label: Flammable Liquid

Purity/Quality:

99%, ^*data from raw suppliers

Triethyl Orthoformate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 10-36-36/38
• Safety Statements: 16-26-37/39-36-45-36/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Ethers, Other
• Canonical SMILES: CCOC(OCC)OCC
• Uses: Labelled Prednisolone 21-Sulfate (P703755). Prednisolone 21-Sulfate is a metabolite of Prednisolone (P703740). A reagent useful for acetylization and imidic ester formation. Triethyl orthoformate is used in Bodroux-Chichibabin aldehyde synthesis to prepare an aldehyde with one carbon higher by reacting with Grignard reagent. It is also used in the electrophilic formylation of activated aromatic species such as phenol.

Technology Process of Triethyl orthoformate

There total 43 articles about Triethyl orthoformate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

ethanol (64-17-5) + trimethyl orthoformate (149-73-5) → orthoformic acid triethyl ester (122-51-0)

Guidance literature:

sulfuric acid; at 140 ℃; under 750.075 Torr; Product distribution / selectivity;

Reference yield: 92.0%

diethyl ether (60-29-7,927820-24-4) + formic acid ethyl ester (109-94-4) → orthoformic acid triethyl ester (122-51-0)

Guidance literature:

With boron trifluoride; In Hexadecane; at 110 ℃; for 18h; Autoclave;

Reference yield: 90.8%

ethanol (64-17-5) + hydrogen cyanide (74-90-8) → orthoformic acid triethyl ester (122-51-0)

Guidance literature:

hydrogen cyanide; With hydrogenchloride; In ethanol; mineral oil; at -10 - 30 ℃; for 2.33333h; Large scale;

ethanol; In mineral oil; at 32 - 55 ℃; for 4h; Concentration; Temperature; Large scale;

upstream raw materials:

tetrachloromethane

sodium ethanolate

ethanol

hydrogen cyanide

Downstream raw materials:

7-hydroxyisoflavone

3-(diethoxymethyl)-2-ethoxytetrahydrofuran

2-Ethoxytetrahydropyran-3-carboxaldehyde-diethylacetal

2-thiophenealdehyde diethyl acetal

Refernces

• 1、 Mochel,Agre,Hanford. "-". . p. 2268. Retrieved 1948.
• 2、 Miloserdov, Fedor M.,Grushin, Vladimir V.. "Alcoholysis of fluoroform". . p. 105 - 109. Retrieved 2014.
• 3、 L?w, Henrik,Mena-Osteritz, Elena,Von Delius, Max. "Self-assembled orthoester cryptands: Orthoester scope, post-functionalization, kinetic locking and tunable degradation kinetics". . p. 4785 - 4793. Retrieved 2018/06/07.
• 4、 -. "Green preparing orthoformate cleaning process". Paragraph 0046; 0048; 0049. . Retrieved 2016/10/07.