triethyl orthoformate
triethoxymethane
Identification
| Name | triethyl orthoformate |
| IUPAC | diethoxymethoxyethane |
| CAS Number | 122-51-0 |
| EINECS | 204-550-4 |
| FDA UNII | 355LRR361Q |
| Molecular Formula | C7 H16 O3 |
| Molecular Weight | 148.20212000 |
| MDL Number | MFCD00009230 |
| Nikkaji Number | J5.533F |
| Beilstein | 0605384 |
| CoE Number | 10903 |
| XlogP3 | 1.20 (est) |
Regulatory
| DG SANTE Food Flavourings | 06.096 triethoxymethane |
Physical Properties
| Appearance | colorless clear liquid (est) |
| Assay | 98.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Specific Gravity | 0.88600 to 0.89500 @ 25.00 °C. |
| Pounds per Gallon - (est). | 7.372 to 7.447 |
| Refractive Index | 1.38900 to 1.39500 @ 20.00 °C. |
| Melting Point | -76.00 °C. @ 760.00 mm Hg |
| Boiling Point | 144.00 °C. @ 760.00 mm Hg |
| Vapor Pressure | 6.987000 mmHg @ 25.00 °C. (est) |
| Vapor Density | 5.11 ( Air = 1 ) |
| Flash Point | 95.00 °F. TCC ( 35.00 °C. ) |
| logP (o/w) | 1.200 |
| Soluble in | alcohol |
| Insoluble in | water |
No sensory data available
Safety Information
| Preferred SDS | View |
| European information | Most important hazard(s): |
| Oral/Parenteral Toxicity | oral-rat LD50 7060 mg/kg |
| Dermal Toxicity | skin-rabbit LD50 20 ml/kg |
| Inhalation Toxicity | inhalation-rat LCLo 4000 ppm/8H |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | flavoring agents |
| Recommendation for triethyl orthoformate usage levels up to | not for fragrance use. |
| Maximised Survey-derived Daily Intakes (MSDI-EU) | 0.013 (μg/capita/day) |
| Modified Theoretical Added Maximum Daily Intake (mTAMDI) | 1600 (μg/person/day) |
| Threshold of Concern | 90 (μg/person/day) |
| Structure Class | III |
| Dairy products, excluding products of category 02.0 (01.0) | 3.00000 |
| Fats and oils, and fat emulsions (type water-in-oil) (02.0) | 2.00000 |
| Edible ices, including sherbet and sorbet (03.0) | 3.00000 |
| Processed fruit (04.1) | 2.00000 |
| Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2) | - |
| Confectionery (05.0) | 4.00000 |
| Chewing gum (05.3) | - |
| Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0) | 2.00000 |
| Bakery wares (07.0) | 5.00000 |
| Meat and meat products, including poultry and game (08.0) | 1.00000 |
| Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0) | 1.00000 |
| Eggs and egg products (10.0) | - |
| Sweeteners, including honey (11.0) | 2.00000 |
| Salts, spices, soups, sauces, salads, protein products, etc. (12.0) | - |
| Foodstuffs intended for particular nutritional uses (13.0) | 3.00000 |
| Non-alcoholic ("soft") beverages, excl. dairy products (14.1) | 2.00000 |
| Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2) | 4.00000 |
| Ready-to-eat savouries (15.0) | 5.00000 |
| Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0) | 2.00000 |
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Potential Uses
Natural Occurrence
Synonyms
diethoxymethoxy)ethane
diethoxymethoxyethane
ethane, 1,1',1''-[methylidynetris(oxy)]tris-
ortho
formic acid ethyl ester
ortho
formic acid triethyl ester
ortho
formic acid, triethyl ester
1,1',1''-[
methanetriyltris(oxy)]triethane
1,1',1'-(
methylidynetris(oxy))tris(ethane)
tri ethyl orthoformate
triethoxymethane
triethyl -o- formate
triethylorthoformate
PubMed:
Triethyl orthoformate mediated a novel crosslinking method for the preparation of hydrogels for tissue engineering applications: characterization and in vitro cytocompatibility analysis.
PubMed:
Ultrasound-promoted one-pot three component synthesis of tetrazoles catalyzed by zinc sulfide nanoparticles as a recyclable heterogeneous catalyst.
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Design and synthesis of new barbituric- and thiobarbituric acid derivatives as potent urease inhibitors: Structure activity relationship and molecular modeling studies.
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Synthesis and evaluation of in vitro antimicrobial activity of novel 2-[2-(aroyl)aroyloxy]methyl-1,3,4-oxadiazoles.
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Synthesis and antimycobacterial activity of novel thiadiazolylhydrazones of 1-substituted indole-3-carboxaldehydes.
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A rapid route to aminocyclopropanes via carbamatoorganozinc carbenoids.
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The chemistry of 5-(tetrazol-1-yl)-2H-tetrazole: an extensive study of structural and energetic properties.
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Enaminonitriles in heterocyclic synthesis: a route to 1,3-diaryl-4-aminopyrazole derivatives.
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Multi-component one-pot synthesis and antimicrobial activities of 3-methyl-1,4-diphenyl-7-thioxo-4,6,8,9-tetrahydro-pyrazolo[5,4-b]pyrimidino[5,4-e]pyridine-5-one and related derivatives.
PubMed:
Synthesis and biological evaluation of 4-alkoxy-6,9-dichloro[1,2,4]triazolo[4,3-a]quinoxalines as inhibitors of TNF-α and IL-6.
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Single step synthesis of new fused pyrimidine derivatives and their evaluation as potent Aurora-A kinase inhibitors.
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Syntheses, electronic structures, and EPR/UV-vis-NIR spectroelectrochemistry of nickel(II), copper(II), and zinc(II) complexes with a tetradentate ligand based on S-methylisothiosemicarbazide.
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Concurrent esterification and N-acetylation of amino acids with orthoesters: A useful reaction with interesting mechanistic implications.
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Towards the synthesis of inosine building blocks for the preparation of oligonucleotides with hydrophobic alkyl chains between the nucleotide units.
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Efficient synthesis of naphtho[1,2-e][1,3]oxazine derivatives via a chemoselective reaction with the aid of low-valent titanium reagent.
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One-pot synthesis of unsymmetrical N-heterocyclic carbene ligands from N-(2-iodoethyl)arylamine salts.
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The synthesis of some perhydrobenzimidazolinium salts and their application in pd-carbene catalyzed heck and suzuki reactions.
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An unprecedented approach to 4,5-disubstituted pyrimidine derivatives by a ZnCl(2)-catalyzed three-component coupling reaction.
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Functionalization of colloidal mesoporous silica by metalorganic reagents.
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First synthesis of [1,3,5-(13)C3]gallic acid.
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Synthesis and antimicrobial activity of some new pyrazole, fused pyrazolo[3,4-d]-pyrimidine and pyrazolo[4,3-e][1,2,4]-triazolo[1,5-c]pyrimidine derivatives.
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Synthesis and antifungal activities of novel 5-amino-6-arylamino-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one derivatives.
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3-[5-(4-Bromophenyl)-1H-pyrazol-3-ylamino]-5,5-dimethylcyclohex-2-en-1-one-(Z)-3-(4-bromophenyl)-3-chloroacrylonitrile (2/1): a stoichiometric cocrystal of a reaction product with one of its early precursors.
PubMed:
Syntheses, structures, near-infrared and visible luminescence, and magnetic properties of lanthanide-organic frameworks with an imidazole-containing flexible ligand.
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Synthesis of new iso-C-nucleoside analogues from 2-(methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-alpha-D-altropyranosid-3-yl)ethanal.
PubMed:
Synthesis of some new annulated pyrazolo-pyrido (or pyrano) pyrimidine, pyrazolopyridine and pyranopyrazole derivatives.
PubMed:
Functionalisation reactions of 2,5-diphenyl-1,3,4-oxadiazoles bearing a terminal ethynyl or butadiynyl substituent: X-ray crystal structures of the products.
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Synthesis of triazole nucleoside derivatives.
PubMed:
Efficient synthesis of 3H-imidazo[4,5-b]pyridines from malononitrile and 5-amino-4-(cyanoformimidoyl)imidazoles.
PubMed:
Solid-phase synthesis of 4(1H)-quinolone and pyrimidine derivatives based on a new scaffold-polymer-bound cyclic malonic acid ester.
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(4R,5S)/(4S,5R)-4,5-Bis(4-hydroxyphenyl)-2-imidazolines: ligands for the estrogen receptor with a novel binding mode.
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[Synthesis of spin labeled analogue of podophyllotoxin glycoside].
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Facile synthesis of 9-substituted 9-deazapurines as potential purine nucleoside phosphorylase inhibitors.
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Nucleosteroids: carbocyclic nucleoside analogs of androst-4-en-17 beta-ol.
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Convenient synthesis of 4,6-di-O-benzyl-myo-inositol and myo-inositol 1,3,5-orthoesters.
PubMed:
Synthesis of some biologically active agents derived from thieno[2,3-d]pyrimidine derivatives.
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Bicyclic [b]-heteroannelated pyridazine derivatives. Part 5. Synthesis of some triazolo[4,3-b]pyridazine and pyridazino[6,1-c]triazine derivatives as potential benzodiazepine receptor ligands.
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Synthesis of thiazole-4-carboxamide-adenine difluoromethylenediphosphonates substituted with fluorine at C-2' of the adenosine.
PubMed:
The reactions of pindolol, mepindolol, carazolol, and related model compounds with triethyl orthoformate: pathways and products of a new colour reaction.
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Synthesis and antiviral activity of carbocyclic analogues of 2'-deoxyribofuranosides of 2-amino-6-substituted-purines and of 2-amino-6-substituted-8-azapurines.
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Synthesis of 5,11-methenyltetrahydrohomofolate and its antifolate activity in vitro.
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Synthesis of dicytidylyl-(3'-5')-1,2-di(adenosin-N6-yl)ethane and dicytidylyl-(3'-5')-1,4-di(adenosin-N6-yl)butane: covalently joined terminals of two transfer ribonucleic acids and their behavior toward snake venom phosphodiesterase.
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Facile syntheses of 1,2,4-triazole and s-triazine glycosides from glycosyl isothiocyanates.
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Model membranes for the study of active transport phenomena.
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