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Triethyl orthoformate= Triethoxymethane= Ethyl orthoformate

CAS Number :122-51-0
EC Number: 204-550-4

Triethyl orthoformate is an organic compound with the formula HC(OC2H5)3.
Triethyl orthoformate, an orthoester of formic acid, is a colorless volatile liquid commercially available.
The industrial synthesis of triethyl orthoformate is made from hydrogen cyanide and ethanol.

Triethyl orthoformate can also be prepared from the reaction of sodium ethoxide and chloroform formed in situ from sodium and absolute ethanol:
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
Triethyl orthoformate coordination chemistry is used to convert metal aquo complexes into 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, which are refluxed purely in excess TEOF until low boilers stop evolution, are quantitatively converted to ethyl esters without the need for foreign catalysis.
Alternatively, TEOF added to ordinary esterifications using catalytic acid and ethanol helps complete the esterification by converting the formed by-product water into ethanol and ethyl formate.

Preferred IUPAC name: (Diethoxymethoxy)ethane
Other names: Triethoxymethane; ethyl orthoformate

CAS Number :122-51-0
ChEMBL : ChEMBL1476236
Chemical Spider: 28955
ECHA Information Card: 100.004.138
EC Number: 204-550-4
PubChem Client ID: 31214
UNII: 355LRR361Q
UN number: 2524
CompTox Control Panel (EPA): DTXSID8041957
Chemical formula :C 7H16O3
Molar mass: 148.202 g mol−1
Density: 0.891 g/mL
Melting point: −76 °C (−105 °F; 197 K)
Boiling point 146 °C (295 °F; 419 K)

Triethyl orthoformate can be used to synthesize:
Formyl ferrocene by reacting with ferrocene in the presence of aluminum chloride.
By cyclocondensation with 5-nitropyridines, nitroacetone and different enamines.
3-Aryl-4(3H)-quinazolinones by reacting with anthranilic acid via heterocyclization catalyzed by concentrated sulfuric acid.

Alternative Name: triethoxymethane
Physical Data: (1) bp 146 °C; d = 0.891 g cm−3; (2) bp 102°C; d = 0.970 g cm−3.
Solubility: dissolve most organic solvents.
Form Provided: clear liquid; widely used.
Refinement: distillation.
Handling, Storage and Precautions: extremely sensitive to moisture; flammable; irritant with high volatility. Use in the hood.

Current Use: TMOF is an essential organic synthesis tool, mainly used to synthesize azoxystrobin and some other pesticides.
Its formal aspect includes pipemidic acid, vitamins, cephalo-type antibiotics, etc. It is used to synthesize, also widely used in the coating, paint and perfume industries.

Storage and Transport: Airtight, dry, ventilation. Tinder should be stored away from the heat source.
Packing: 200KGS/DRUM; ISO TANK

Appearance : Colorless transparent liquid
Experiment: ≥99.4%
Methyl Format: ≤0.2%
Methanol : ≤0.3%
CAS No.: 149-73-5 UN N0.: 3272
Physical properties :
Density: 0.97
Melting Point: -53 ℃
Boiling Point: 103-105 ℃
Refractive Index: 1.379
Flash Point: 15 ℃
Molecular Formula: C4H10O3
Molecular Weight: 106.12

Triethyl orthoformate is used in aldehyde synthesis to prepare an aldehyde with one carbon higher by reacting with Grignard's reagent.
It is also used in the electrophilic formulation of activated aromatic species such as phenol.

Miscible with alcohols, acetone, ethers and chloroform.
It is slightly miscible with water.

Moisture sensitive.
Incompatible with acids and strong oxidizing agents.

Triethyl orthoformate is a useful organic synthesis reagent for acetylation, imidic ester formation and activated aromatic species formation.

Chemical properties
Colorless liquid; pungent odor. Extremely flammable.
Slightly soluble in water; alcohol, soluble in ether; decomposes in water.

Current use
Labeled Prednisolone 21-Sulphate (P703755).
Prednisolone 21-Sulphate is a metabolite of Prednisolone (P703740).
A useful reagent for acetylation and imidic ester formation.
Triethyl orthoformate is used in the Bodroux-Chichibabin aldehyde synthesis to prepare an aldehyde with one carbon higher by reacting with the Grignard reagent.
Triethyl orthoformate is also used in the electrophilic formulation of activated aromatic species such as phenol.

General description
A clear, colorless liquid with a pungent odour.
Less dense than water.
Flash point is 86°F.
Vapors are heavier than air.
May irritate skin and eyes.
It is used to make other chemicals.

Reactivity Profile
Triethyl orthoformate is an ester. It reacts with acids to release heat along with esters, alcohols and acids.
Strong oxidizing acids can cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products.
Heat is also produced by the interaction of esters with caustic solutions.
Combustible hydrogen is produced by mixing esters with alkali metals and hydrides.

Treatment Methods
Disassemble first at atmospheric pressure, then in vacuum.
Triethyl orthoformate impure, then rinse with aqueous 2% NaOH, dry with solid KOH and distill from sodium via a 20 cm Vigreux column (p 11).
Alternatively, wash with H2O, dry over anhydrous K2CO3, filter and fractionate with a Widmer column.

Orthoester (1,1,1-triorganyloxyalkane)
(1) is the general name of a functional group containing three alkoxy groups attached to a central carbon atom with the general formula RC(OR')3. In fact, they are esters of orthoacids that are not in free form.1,2 Orthoesters were first synthesized via the nucleophilic substitution reaction of chloroform.
(2) with alkoxides
(3) by Williamson and Kay in 1854. There are several examples of acyclic alkylorthoesters.

(a) Trimethyl orthoformate (TMOF) is the simplest orthoester in organic chemistry and is also called trimethoxymethane, 2-methoxyacetaldehyde dimethyl acetal, methoxymethylal and methyl orthoformate.
This colorless liquid with a pungent odor is soluble in ethanol and ether ((CH(OMe)3, 4), bp = 100.6 °C and d = 0.9676 g mL-1.
(b) Triethyl orthoformate (TEOF, CH(OEt)3, 5), also called diethoxymethoxyethane, triethoxymethane and ethyl orthoformate, is a colorless volatile liquid with bp = 146 °C and d = 0.891 g mL-1. acid .
(c) Triethyl orthoacetate (TEOAc, CH3C(OEt)3, 6) 1,1,1-triethoxyethane, (bp = 142 °C, d = 0.885 g mL-1), is an oily yellow to colorless liquid with a pungent odour.
(d) 1,1,1-triethoxypropane and triethyl orthopropionate (CH3CH2C(OEt)3, 7), also called orthopropionic acid triethyl ester, is a clear colorless liquid (bp = 155–169 °C, d = 0.886 g mL−1 ) dissolves in alcohol, chloroform, ethyl acetate and ether and hydrolyzes slowly in water.

Orthoesters can be considered as products of extensive alkylation of labile orthocarboxylic acids, from which the name "orthoester" is derived.
Orthoesters are highly reactive due to the electron-deficient central carbon atom caused by the –I effect of electronegative groups OR.
Among these introduced orteosters, TEOF is maximally exploited in reactions based on our literature search followed by TMOF, TEOAc, TMOAc and triethyl orthopropionate (2 cases) and other types of alkyl orthoesters (1 case).
Several orthoesters have been applied in various fields such as dehydrating agents, alkylating agents, dialkoxymethylating agents, esterifying agents, methoxy sources, additives, solvents and protecting groups.
This functional group is also required for some transformations, such as the Johnson-Claisen rearrangement. indicates the various applications indicated against the orthoester type.
As mentioned, TMOF and TEOF are the most commonly used in different processes, except in the case of rearrangements where TMOAc is most abundant.

( a ), various applications of different types of orthoesters in some processes
(b) and classification of their use in various fields of science and technology
( c ). Analysis of different types of orthoesters, as well as polymers, liquid crystal compounds, biochemistry, medical and medicinal organic chemistry, inorganic chemistry, organometallic chemistry, dynamic covalent chemistry,64 supramolecular chemistry and crystal structure.
Orthoesters have also been used in the synthesis of natural products, eg. Loganin is a monoterpene glucoside that occupies a central position in the formation of secoiridoids and alkaloids obtained biosynthetically from orthoesters.
Therefore, in 1973 Buechi and colleagues described the total synthesis of loganin.
It should be noted that trimethyl orthoformate is used in some steps in the preparation of loganine and in the total synthesis of (-)-monomorin and (±)-vernolepine.
Triethyl orthoformate, TEOF, has been reported to be used in the total synthesis of palytoxin as a marine natural product.
Triethyl orthoformate 1976, Greenlee and Woodward reported the total synthesis of marasmic acid, one of many fungal metabolites from Basidiomycetes, to which trialkyl orthoformates were applied in some syntheses.
Chan and Koide used orthoesters for the first total synthesis of the stressgene B scaffold as a heat shock protein expression inhibitor.
Triethyl orthoformate 1967, Gauthier and Deslongchamps achieved spinning by a multistep process initiated by TEOF as one of the substrates.
 The triethyl orthoformate diagram illustrates a wide variety of applications of different types of orthoesters in various sciences.
The results demonstrate the extensive use of orthoesters in many fields of science and technology.

In addition to the Williamson and Kay method, there are several procedures for preparing orthoesters.
Pinner reaction of nitriles with alcohols in the presence of strong acids formed orthoesters.
Electrochemical approaches78-81 are also used for the synthesis of these compounds; for example, various fluoro alcohols (1,1,1,3,3,3-hexafluoropropan-2-ol (HFIP, 12) or 2,2,2-trifluoroethanol (TFE, 13)) undivided at the 2-position boron-doped diamond (BDD) electrodes in a cell and under constant current density of 5.4.0]undec-7-ene (DIPEA/DBU), 7.2 mA cm−2 in the presence of N,N-diisopropylethylamine or 1,8-diazabicyclo-[ until a catalytic amount of electricity of 3.0 F mol-1 was obtained as the basic electrolytes by

The triethyl orthoformate invention describes a synthesis method for triethyl orthoformate.
The synthesis method uses a dehydrating agent and contains glycerine, active argyl and 4A molecular sieve in a mass ratio of 10:(2- 1):( 2-1).
Thanks to the dehydration agent, the moisture in the synthesis process of triethyl orthoformate can be greatly reduced, the loss amount of the triethyl orthoformate product in the separation stage can be reduced, the raw material waste and industrial energy consumption can be reduced, and the synthesis method is applicable to large-scale industrial production.

The triethyl orthoformate process for synthesizing triethyl orthoformate is the characteristics of using sodium hydroxide with chloroform drop by drop in time, controlling the pH value up to 7-10 during the whole reaction process and controlling the proportion of materials and using a scientific washing method in separation refining. step of reusing the azeotropic agent.
Its advantages include high purity up to 98-99%, less raw material consumption and high efficiency up to 65-75%.

Triethyl orthoformate is C7H16O3, a colorless liquid mainly used in organic synthesis.

Current Use: TMOF is an essential organic synthesis tool, mainly used to synthesize azoxystrobin and some other pesticides.
Its formal aspect includes pipemidic acid, vitamins, cephalo-type antibiotics, etc. It is used to synthesize, also widely used in the coating, paint and perfume industries.
Storage and Transport: Airtight, dry, ventilation. Tinder should be stored away from the heat source.

Precautionary Statements - Prevention
Wash face, hands and exposed skin thoroughly after use.
Wear protective gloves/protective clothing/eye protection/face protection
Avoid breathing dust/fume/gas/mist/vapour/spray
Use only outdoors or in a well-ventilated area.
Keep away from heat/sparks/open flames/hot surfaces. - No smoking
Keep container tightly closed Ground/connect container and receiving equipment
Use explosion-proof electrical/ventilation/lighting equipment
Only use non sparking tools
Take precautions against static discharge

Precautionary Statements - Intervention
Special treatment (see additional first aid instructions on this label)
IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present, and
to do . Keep rinsing
If eye irritation persists: Get medical advice/attention
If skin irritation occurs: Get medical advice/attention
IF ON SKIN (or hair): Take off/take off immediately all contaminated clothing. Rinse skin with water/shower Wash contaminated clothing before reuse
IF INHALED: Remove casualty to fresh air and rest in a position comfortable for breathing.
Call a POISON CENTER or doctor/physician if you feel unwell
In case of fire: Use CO2, dry chemical or foam to extinguish.
Precautionary Statements - Storage
Store in a well-ventilated place. Keep container tightly closed
Store is locked
Precautionary Statements - Disposal
Dispose of contents/container to an approved waste disposal facility
Hazards not otherwise classified (HNOC): None known
Appearance: Colorless Transparent
Physical State: Liquid
Odor: pungent

General Advice: Show this safety data sheet to the attending physician.
Eye Contact: Immediately flush with plenty of water, also under the eyelids, for at least 15 minutes.
Consult a doctor.
Skin Contact: Remove all contaminated clothing and shoes and wash immediately with soap and plenty of water. Wash contaminated clothing before reuse. Consult a doctor.
Inhalation: Get to fresh air. If breathing is difficult, give oxygen. If not breathing, give artificial respiration. Consult a doctor.
Ingestion: Do not induce vomiting. Rinse mouth. Never give anything by mouth to an unconscious person. Consult a doctor.
First Aid Protection: Remove all sources of ignition. Use personal protective equipment.
Avoid contact with skin, eyes and clothing.
Most Important Symptoms and Effects, Both Acute and Delayed
Main Symptoms: No information available.
Symptom Requirement of Emergency Medical Intervention and Special Treatment
Notes to Physician: Treat symptomatically.

Fire Fighting Measures
Flammable Properties: Flammable liquid. Vapors may cause flash fire or explosion.
Suitable Extinguishing Media: Water spray. Carbon dioxide (CO2). Dry powder. Torn. Water mist can be used to cool closed containers.
Unsuitable Extinguishing Media: Water. Do not use straight streams of water.
Hazardous Combustion Products: Thermal decomposition or combustion may produce hazardous gases and/or materials.
Explosion Data
Susceptibility to Mechanical Impact: Not available.
Static Discharge Sensitivity: Not available.
Special Hazards from Chemicals: Keep product and empty container away from sources of heat and ignition. Kickback is possible from a considerable distance.
Container explosion may occur under fire conditions.
Protective Equipment and Precautions for Firefighters: As with any fire, wear self-contained breathing apparatus, pressure-requiring, MSHA/NIOSH (approved or equivalent), and full protective clothing.

Personal Precautions, Protective Equipment and Emergency Procedures
Personal Precautions: Evacuate personnel to safe areas. Provide adequate ventilation. Use personal protective equipment. Avoid contact with skin, eyes and clothing. In case of insufficient ventilation, wear appropriate respiratory equipment. Eliminate all ignition sources. Take precautions against static discharges. Watch out for flashback.
Other Information: Not applicable.
Environmental Precautions: If significant spillage cannot be contained, local authorities should be notified. If safe, prevent further leaks or spills. Do not allow material to contaminate the groundwater system. Prevent the product from entering the sewer. surface water or
sanitary sewer system. It should not be released into the environment. Methods and Materials for Containment and Cleaning
Limitation Methods: Not available.
Clean Up Methods: Evacuate personnel to safe areas. Absorb spillage with inert material (eg dry sand or earth), then place in chemical waste container. Clean the contaminated surface
thoroughly . Eliminate all ignition sources. Use spark-proof tools and explosion-proof equipment.
When transferring material to ground and bond containers. Take precautions against static discharges.

Precautions for Safe Use
Handling: Use only in an area with a safety shower. Make sure eyewash stations and safety showers are close to the workstation location. Provide adequate ventilation. Do not breathe vapors or spray mist. Avoid contact with skin, eyes and clothing. Avoid repeated exposure. Keep away from open flames, hot surfaces and sources of ignition. All metal parts of equipment must be grounded to prevent ignition of vapors by static electricity discharge.
Conditions for safe storage, including any incompatibilities
Storage: Keep container tightly closed. Store in appropriately labeled containers. Keep away from open flames, hot surfaces and sources of ignition. Protect from moisture. Protect from water.
Incompatible Materials Acids: Oxidizing agents.

Category: Ethers, Other
Description: Sweet-smelling liquid like pine needles; [Merck Index] Clear colorless liquid with a pungent odour; [CAMEO]
Sources/Uses: Used in the manufacture of chemicals; [CAMEO] In chemical synthesis, paint-lacquer-varnish industry and as a stabilizer; [IUCLID] Used to make large-scale and fine chemicals; [ECHA REACH Registers] Authorized for use as an inert ingredient in non-food pesticide products; [EPA]
Comments: Mild skin and moderate eye irritant; Dermal LD50 (rabbit) = 20 mL/kg; [RTECS] Not skin sensitizer in guinea pig maximization study; No sensitivity reaction was observed in the maximization test of 26 volunteers at 4% in petrolatum; [IUCLID] Safe when used as a flavoring agent in foods; [EFSA] A mild skin irritant; [Sigma-Aldrich MSDS] See. "1,1-Dimethoxyethane".

Triethyl Orthoformate, also known as Triethoxymethane or Ethyl orthoformate, is commercially available as a formic acid orthoester.
Unrated products provided by Spectrum are indicative of a grade suitable for general industrial or research purposes and are typically not suitable for human consumption or therapeutic use.
Size: 100mL
Manufacturer: Spectrum Chemical
Catalog Number: T2231
CAS No: 122-51-0
MSDS: Material Safety Data Sheet
DOT: UN2524, Ethyl orthoformate, 3, PG III
Tariff No 2915905000

Triethyl orthoformate is an organic compound with the formula HC(OC2H5)3. It is a colorless volatile liquid.
Triethyl orthoformate is the orthoester of formic acid.
Commercially available industrial synthesis is made from hydrogen cyanide and ethanol.
There is a need for the development of pro-angiogenic biomaterials to promote wound healing and aid regenerative medicine.
For this purpose, various growth factors that have the potential to promote angiogenesis have been utilized.
However, they are often expensive and variable, limiting their effectiveness.
An alternative approach to triethyl orthoformate is to immobilize heparin on biocompatible degradable hydrogels.
Triethyl orthoformate heparin will then bind endogenous proangiogenic growth factors to induce the formation of new blood vessels.

We continue our wound healing hydrogel development by exploring covalently cross-linked chitosan and polyvinyl alcohol hydrogels using triethyl orthoformate.
Two concentrations of triethyl orthoformate (4 and 16%) were compared for their effects on the structure of the hydrogels - their swelling, pore size and degradation rate, and their ability to support cell growth and bind to heparin. Effects on angiogenesis in a chick chorioallantoic membrane assay.

Hydrogels formed with 4% or 16% of both triethyl orthoformate crosslinkers were equally cytocompatible.
Hydrogels formed with 4% triethyl orthoformate absorbed slightly more water than those made with 16% triethyl orthoformate and degraded slightly faster than non-crosslinked hydrogels.
When dipped in heparin, the hydrogel formed with 16% triethyl orthoformate showed greater blood vessel formation in the CAM assay than that formed with 4% triethyl orthoformate.

1. Absolute Alcohol.— Good absolute alcohol is essential. Use of about 98 percent alcohol yields only about two-thirds of the yield with absolute alcohol. Alcohol dried on lime is usually around 98.5-99.5 percent. A good method of obtaining a higher grade of absolute alcohol is to treat it with some sodium. When the sodium dissolves, the alcohol is distilled from a steam bath. Under these conditions, any traces of water that may be present due to equilibrium remain in the concentrated sodium ethoxide and sodium hydroxide solution.
2. At the end of the reaction, sufficient chloroform should be used so that the solution is not alkaline.
3. Care is taken not to allow moisture to enter the alcohol-chloroform mixture, which is recovered from triethyl orthoformate, this mixture can be used repeatedly. After using it four or five times, the efficiency starts to decrease.
4. The triethyl orthoformate long fractionation column used by Clarke and Rahrs1 is satisfactory. If there is no such column, then 80 cm. The water-free reflux condenser can be used by connecting it via a large, bent glass tube to a condenser located downwards for distillation at the top.
5. Bottle type satisfying triethyl orthoformate for distillation,
6. The present method is better than the method using dry ether as solvent.
7. Yields as good as those specified in the above procedure are obtained by first preparing a sodium ethoxide solution, taking the amounts given above, and adding it to an alcohol-chloroform solution.
A disadvantage agreed with this alternative procedure is that unless much more alcohol is used, the sodium ethoxide solution tends to become semisolid and cannot be readily incorporated into the chloroform-alcohol solution.
If reclaimed alcohol containing chloroform is attempted to be used, sodium chloride, which separates as soon as sodium is added, increases its tendency to become semisolid.
The triethyl orthoformate reaction is best performed without mixing so that the sodium is allowed to float on top.
In this way, hydrogen escapes quickly and there is little reduction in chloroform.

( triethyl orthoformate + diethyl malonate) were measured with an inclined ebulliometer.
Triethyl orthoformate test results are analyzed using the UNIQUAC equation with temperature dependent binary parameters with satisfactory results. Experimental vapor pressures of triethyl orthoformate are also included.

Triethyl Orthoformate - Preparation Method
The sodium ethoxide method uses sodium ethoxide and chloroform as raw materials to react at 60 to 65 °C.
To produce a crude triethyl orthoformate which is then fractionated to obtain a finished product.
Ethanol method for ethanol and sodium hydroxide instead of sodium ethoxide, use of solid-liquid phase transfer catalysis, catalyst for PTC.
The method of benzoyl chloride with benzoyl chloride, formamide and anhydrous ethanol as raw materials under the action of the catalyst, the formation of a mixture of triethyl orthoformate, benzoic acid and ammonium chloride, the separation of the finished product of triethyl orthoformate and benzoic acid.

Triethyl Orthoformate - Nature
Colorless liquid with a pungent odor.
The relative density was 0.8909.
Melting point <-18 °C.
Boiling point is 143 C (102 kPa).
Flash point 27 °C.
The refractive index is 3900.
Miscible with ethanol and ether.
It is slightly soluble in water, but decomposes in water.

Triethyl Orthoformate - Usage
pharmaceutical raw materials, antimalarial drugs are chloroquine, kikin and other synthetic raw materials.
Triethyl orthoformate is also used in the manufacture of polymers, photographic drugs, photosensitive materials, anti-halo dyes, cyanine dyes and synthetic pesticides.

Triethyl Orthoformate - Safety
The toxicity of triethyl orthoformate of this product is very low, and the oral LD50 of rats is 7.06g/kg.
The triethyl orthoformate product is packaged in an iron barrel and the muzzle must be sealed.
According to the general provisions regarding the storage and transportation of chemicals.

triethyl orthoformate
ethyl orthoformate
methane, triethoxy-
Ethyl format(ortho)
Orthoformic acid triethyl ester
Ethane, 1,1',1''-[methylidinetris(oxy )]tris -
orthomravencan ethylnati
Orthoformic acid, triethyl ester
ethylester kyseliny orthomravenci
triethoxy methane
MGK 5289
orthoformic acid ethyl ester
Triethylester kiselini orthomravenci
Ethane, 1,1',1''-(methylidinetris(oxy ))tris -
1,1',1''-[methantriyltris(oxy )]triethane

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