Triethyl orthoacetate

Base Information

• Chemical Name: Triethyl orthoacetate
• CAS No.: 78-39-7
• Molecular Formula: C8H18O3
• Molecular Weight: 162.229
• Hs Code.: 29159080
• European Community (EC) Number: 201-112-4
• NSC Number: 5596
• UNII: 48352MHC78
• DSSTox Substance ID: DTXSID4058815
• Nikkaji Number: J4.220J
• Wikipedia: Triethyl_orthoacetate
• Wikidata: Q489234
• RXCUI: 2474630
• Mol file: 78-39-7.mol

Synonyms:Triethyl orthoacetate;1,1,1-Triethoxyethane;78-39-7;Ethane, 1,1,1-triethoxy-;Ethyl orthoacetate;Orthoacetic acid, triethyl ester;TRIETHYL ORTHO ACETATE;C8H18O3;1,1,1-triethoxy-ethane;Orthoacetic Acid Triethyl Ester;UNII-48352MHC78;NSC 5596;NSC-5596;EINECS 201-112-4;48352MHC78;AI3-23843;triethoxyethane;triethoxy ethane;triethy orthoacetate;triethylorthoacetat-;diethoxydiethyl ether;MFCD00009223;triethyl ortho-aceate;1,1-Triethoxyethane;triethyl ortho-acetate;(EtO)3CMe;MeC(OEt)3;Ethane,1,1-triethoxy-;Orthoacetic acid triethyl;1,1,1-triethoxy ethane;(EtO)3CCH3;CH3C(OEt)3;Triethyl orthoacetate, 97%;SCHEMBL40105;DTXSID4058815;NSC5596;BBL011491;STL146603;AKOS000119996;1,1',1"-[ethylidynetris(oxy)]trisethane;1,1', 1"-[ethylidynetris(oxy)]trisethane;LS-191571;FT-0621758;FT-0651307;FT-0657987;FT-0675473;O0105;EN300-20407;E75963;Triethyl orthoacetate, purum, >=98.0% (GC);A839409;Q489234;Q-201869;F0001-2051;ETHANE,1,1,1-TRIETHOXY ORTHOACETIC ACID,TRIETHYL ESTER

Chemical Property of Triethyl orthoacetate

Chemical Property:

• Appearance/Colour: clear colourless liquid
• Vapor Pressure: 3.4 hPa (20 °C)
• Refractive Index: n20/D 1.396(lit.)
• Boiling Point: 145 °C at 760 mmHg
• Flash Point: 36.1 °C
• PSA: 27.69000
• Density: 0.902 g/cm³
• LogP: 1.76960
• Storage Temp.: Flammables area
• Sensitive.: Moisture Sensitive
• Water Solubility.: SLIGHTLY SOLUBLE
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 162.125594432
• Heavy Atom Count: 11
• Complexity: 76.3

Purity/Quality:

99% ^*data from raw suppliers

Triethyl Orthoacetate ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Ethers, Other
• Canonical SMILES: CCOC(C)(OCC)OCC
• Description: Triethyl orthoacetate is the ethyl orthoester of acetic acid. It is an oily liquid with a pungent odor. Triethyl orthoacetate is used as a water scavenger and as intermediate for synthesis of pharmaceuticals. It is used in organic synthesis for the introduction of the acetate group to an alcohol and in the Johnson-Claisen rearrangement.
• Uses: Intermediate. Triethyl orthoacetate is used as pharmaceutical and water scavenger. It is also used in organic synthesis to introduce the acetate group into an alcohol. It is involved in the Johnson-Claisen rearrangement.

Technology Process of Triethyl orthoacetate

There total 36 articles about Triethyl orthoacetate 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: 90.0%

diethyl ether (60-29-7,927820-24-4) + ethyl acetate (141-78-6) → Triethyl orthoacetate (78-39-7)

Guidance literature:

With boron trifluoride; In Hexadecane; at 110 ℃; for 12h; Autoclave;

Reference yield: 34.0%

ketene diethyl acetal (2678-54-8) + dimethylglyoxal (431-03-8) → 3-hydroxy-3-methyl-levulinic acid ethylester (67079-92-9) + 2,2-diethoxy-4-acetyl-4-methyl-oxetane (93183-68-7) + ethyl acetate (141-78-6) + Triethyl orthoacetate (78-39-7)

Guidance literature:

In acetonitrile; Ambient temperature; thermal reaction;

DOI:10.1016/S0040-4039(01)80035-6

Reference yield: 27.0%

ethanol (64-17-5) + C7H14NO2(1+)*CH3O4S(1-) → Triethyl orthoacetate (78-39-7)

Guidance literature:

With ethyl acetate; 1) 16h, 2) 4h, 40 deg C;

upstream raw materials:

piperidine

ketene diethyl acetal

diethyl ether

1,1,1-trichloroethane

Downstream raw materials:

1-methyl-2-[2-(2-methyl-indol-3-yl)-propenyl]-naphtho[1,2-d]thiazolium; toluene-4-sulfonate

ethyl 2-pyridinylcarbamate

1,3-di-pyridin-2-yl-urea

1-methyl-[1,2,4]triazolo[4,3-a]quinoline

Refernces

Synthesis and cytotoxicity studies of quinoline-3-carbonitrile derivatives

10.1016/j.cclet.2010.03.016

The study focuses on the design, synthesis, and in vitro cytotoxicity evaluation of a series of quinoline-3-carbonitrile derivatives against four cancer cell lines: A549 (lung), HT-29 (colon), MDA-MB-231 (breast), and SMMC-7721 (liver). The research aimed to develop potent and selective anti-tumor agents by replacing the quinazoline scaffold of Gefitinib, an EGFR tyrosine kinase inhibitor, with a quinoline-3-carbonitrile scaffold. The synthesized compounds were tested for their cytotoxic effects using the MTT assay, and the results showed that several of these derivatives exhibited superior selective cytotoxicity against the SMMC-7721 cell line compared to Gefitinib, with compound 11g being the most potent among them. The study also provided preliminary insights into the structure-activity relationships of these compounds, suggesting their potential as anti-cancer agents. Further research on their anti-tumor activities and detailed structure-activity relationships is ongoing.

Regioselective synthesis of pyrimido[1,2-a][1,3,5]triazin-6-ones via reaction of 1-(6-oxo-1,6-dihydropyrimidin-2-yl)guanidines with triethylorthoacetate: Observation of an unexpected rearrangement

10.1039/c2ob25195g

The research focuses on the regioselective synthesis of pyrimido[1,2-a][1,3,5]triazin-6-ones, which are structurally significant due to their presence in numerous biologically active compounds with potential anti-cancer properties. The study investigates the thermal rearrangement reactions of (6-oxo-1,6-dihydropyrimidin-2-yl)guanidines with triethyl orthoacetate, leading to the formation of 4-substituted-2-methyl-6H-pyrimido[1,2-a][1,3,5]triazin-6-ones and their ring-opened products. The research explores the regioselective synthesis of these compounds and the conditions under which an unexpected rearrangement occurs, depending on the substituents present in the starting guanidine. The experiments involved the use of various analytical techniques such as mass spectrometry, NMR, elemental analysis, and X-ray crystallography to characterize the synthesized compounds and understand the observed thermal rearrangement. The study also discusses the antiproliferative activity of the synthesized compounds against specific cancer cell lines.

An efficient synthesis of 2,6-disubstituted benzobisoxazoles: New building blocks for organic semiconductors

10.1021/ol802011y

The study presents an efficient synthesis method for 2,6-disubstituted benzobisoxazoles, which are promising building blocks for organic semiconductors. The key chemicals involved are diaminobenzene diols, specifically 2,5-diaminohydroquinone (DAHQ) and 4,6-diaminoresorcinol (DAR), which react with various orthoesters to form the desired benzobisoxazoles. Orthoesters, such as triethyl orthoformate, triethyl orthoacetate, trimethylsilyl ethyl orthopropiolate, triethyl orthobromoacetate, and triethyl orthochloroacetate, serve as both reactants and solvents in the reactions. The study explores different catalysts, including traditional acids like H2SO4 and rare earth metal triflates like Y(OTf)3 and La(OTf)3, to optimize the reaction conditions. The optimized conditions involve using DMSO as a cosolvent, a catalytic amount of metal triflate, and pyridine to enhance yields and reduce reaction temperatures. The synthesized benzobisoxazoles can be further transformed into monomers for the synthesis of conjugated polymers, as demonstrated by the synthesis of a soluble PBO derivative through the Arbuzov reaction and subsequent polymerization.