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Triethyl orthoformate

Triethyl orthoformate structure

CAS No:
122-51-0
Formula:
C7H16O3
Chemical Name:
Triethyl orthoformate
Synonyms:
Ethane,1,1′,1′′-[methylidynetris(oxy)]tris-;Orthoformic acid,triethyl ester;1,1′,1′′-[Methylidynetris(oxy)]tris[ethane];Aethon;Ethyl orthoformate;Triethoxymethane;Triethyl orthoformate;Orthoformic acid ethyl ester;Ethone;OF;OFE (ether);OFE;NSC 5289;(Diethoxymethoxy)ethane;Triethylorthformate
Categories:
Organic Chemistry > Carboxylic Acids and Derivatives

Description

Triethyl Orthoformate, also known as triethyl orthoformate, is an organic compound with a specific chemical structure, the form C₇H₁₈O₄. This compound plays an important role in the field of organic chemistry and is often widely used as an important reagent in organic synthesis reactions. Triethyl Orthoformate is a colorless, transparent liquid with a distinctive pungent odor, which is particularly pronounced when dealing with the compound. As a Orthoformate, Triethyl Orthoformate has a molecular structure that contains multiple ethyl groups (-C₂H₅) attached to a central carbon atom, which also forms part of the formate. This structure allows it to serve as a source of formic acid in various chemical reactions, thus playing a key role in the synthesis process. The physical properties of Triethyl Orthoformate are also worth mentioning. It's less dense than water, which means it floats to the surface in water. At the same time, its vapor density is greater than that of air, which indicates that its vapor sinks in air. When used, it is important to note that Triethyl Orthoformate may have an irritating effect on the skin and eyes, so appropriate safety measures should be taken during operation, such as wearing protective glasses and gloves. Because of its importance in organic synthesis, Triethyl Orthoformate is widely used in the manufacture of a variety of other chemicals. It plays an integral role both as an intermediate in the reaction and in the synthesis of the final product. Because of its unique chemical properties and reaction ability, Triethyl Orthoformate has a wide range of applications in chemical research and industrial production.

Triethyl orthoformate Basic Attributes

Molecular Weight：

148.20000

Exact Mass：

148.20

EC Number：

204-550-4

UNII：

355LRR361Q

NSC Number：

5289

UN Number：

2524

DSSTox ID：

DTXSID8041957

HScode：

2915130000

Characteristics

PSA：

27.69000

XLogP3：

1.37950

Appearance：

Ethyl orthoformate appears as a clear, colorless liquid with a pungent odor. Less dense than water. Vapors heavier than air. May irritate skin and eyes. Used to make other chemicals.

Density：

0.8858 g/cm³ @ Temp: 25 °C

Melting Point：

-61ºC

Boiling Point：

143 °C

Flash Point：

30ºC

Refractive Index：

1.39-1.392

Water Solubility：

H2O: 1.35 g/L

Storage Conditions：

Flammables area

Vapor Pressure：

2.9 mm Hg ( 20 °C)

Vapor Density：

5.11 (vs air)

Air and Water Reactions：

Highly flammable. Slightly soluble in water.

Reactive Group：

Ethers

Reactivity Alerts：

Highly Flammable

Reactivity Profile：

ETHYL ORTHOFORMATE is an ether. Ethers can act as bases. They form salts with strong acids and addition complexes with Lewis acids. The complex between diethyl ether and boron trifluoride is an example. Ethers may react violently with strong oxidizing agents. In other reactions, which typically involve the breaking of the carbon-oxygen bond, ethers are relatively inert.

Safety Information

Packing level：

III

Hazard category：

Transport codes：

UN 2524

wgk germany：

hazard class code：

R10; R36/38

safety instructions：

S16-S26-S37/39

RTECS Number：

RM6475000

Marks：

Stability/Shelf Life：

Stable under normal temperatures and pressures.

Precautionary statement(s)：

P210-P403 + P235

Hazard Statements：

H226

Fire Hazards：

Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. (ERG, 2016)|Flammable - 3rd degree

GHS Classification：

|Warning|H226 (89.09%): Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P261, P264, P271, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P370+P378, P403+P233, P403+P235, P405, and P501|Aggregated GHS information provided by 511 companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H226: Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P261, P271, P280, P303+P361+P353, P304+P312, P304+P340, P312, P370+P378, P403+P235, and P501

Fire Fighting：

Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]: CAUTION: All these products have a very low flash point: Use of water spray when fighting fire may be inefficient. SMALL FIRE: Dry chemical, CO2, water spray or alcohol-resistant foam. Do not use dry chemical extinguishers to control fires involving nitromethane (UN1261) or nitroethane (UN2842). LARGE FIRE: Water spray, fog or alcohol-resistant foam. Do not use straight streams. Move containers from fire area if you can do it without risk. FIRE INVOLVING TANKS OR CAR/TRAILER LOADS: Fight fire from maximum distance or use unmanned hose holders or monitor nozzles. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire. For massive fire, use unmanned hose holders or monitor nozzles; if this is impossible, withdraw from area and let fire burn. (ERG, 2016)

Isolation and Evacuation：

Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]: As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. LARGE SPILL: Consider initial downwind evacuation for at least 300 meters (1000 feet). FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

Nonfire Spill Response：

Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). All equipment used when handling the product must be grounded. Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. A vapor-suppressing foam may be used to reduce vapors. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. Use clean, non-sparking tools to collect absorbed material. LARGE SPILL: Dike far ahead of liquid spill for later disposal. Water spray may reduce vapor, but may not prevent ignition in closed spaces. (ERG, 2016)

Personal Protective Equipment：

Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection. (ERG, 2016)

Drug Information

Health Hazards：

Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]: May cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution. (ERG, 2016)

First Aid：

Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]: Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. Wash skin with soap and water. In case of burns, immediately cool affected skin for as long as possible with cold water. Do not remove clothing if adhering to skin. Keep victim calm and warm. Effects of exposure (inhalation, ingestion or skin contact) to substance may be delayed. (ERG, 2016)

Triethyl orthoformate Use and Manufacturing

Uses

Triethyl Orthoformate is a compound widely used in organic chemical synthesis, which plays a crucial role in the preparation of various organic molecules. This compound is mainly used for the synthesis of acetal and hemiacetal compounds, through its unique chemical properties, can effectively promote the formation of these compounds. In organic synthesis reactions, an important use of Triethyl Orthoformate is as a carbonyl protective agent, by protecting the carbonyl group, it can ensure that the carbonyl group will not have unnecessary side reactions with other reactants during the selective reaction, thereby improving the selectivity and yield of the reaction. In addition to its applications in the synthesis of acetal and hemiacetal compounds, Triethyl Orthoformate is also widely used in the pharmaceutical industry, agrochemicals, and the production of fine chemicals. In these fields, as a multifunctional organic synthesis reagent, it can participate in many types of chemical reactions, such as condensation reaction, esterification reaction, etc., thus providing convenience for the production of various complex organic molecules. Its high reactivity and good selectivity enable it to effectively control the direction of reaction, reduce the generation of by-products, and improve the purity and yield of target products. These characteristics of Triethyl Orthoformate not only make it of great value in laboratory research, but also show its irreplaceable role in industrial production. Due to its extensive application and significant advantages in organic synthesis, Triethyl Orthoformate has become increasingly important in the field of chemistry and has become one of the indispensable tools for organic synthetic chemists.

Production

25,000 - 100,000 lb

Manufacturing Info：

Adhesive manufacturing|Ethane, 1,1',1''-[methylidynetris(oxy)]tris-: ACTIVE

Use Classification：

Food additives -> Flavoring Agents|Fire Hazards -> Flammable - 3rd degree

Food Additive Classes：

Flavoring Agents

Computed Properties

Molecular Weight:148.20
XLogP3:1.2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:6
Exact Mass:148.109944368
Monoisotopic Mass:148.109944368
Topological Polar Surface Area:27.7
Heavy Atom Count:10
Complexity:51.6
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

Trimethyl orthoformate

Ethanol

Hydrochloric acid

Downstream Products

Ethanol

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