Trifluoroacetic Anhydride CAS 407-25-0


Factory wholesale Trifluoroacetic Anhydride CAS 407-25-0
- Appearance:Liquid
- Purity:99.8%
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Name: Trifluoroacetic Anhydride
CAS: 407-25-0
MOQ: 1KG
Directory Guidance on Trifluoroacetic Anhydride
Chemical Structure
Basic Info:
Melting point | -65 °C (lit.) |
Boiling point | 39.5-40 °C (lit.) |
density | 1.511 g/mL at 20 °C (lit.) |
vapor pressure | 6.28 psi ( 20 °C) |
refractive index | n20/D 1.3(lit.) |
Fp | -26 °C |
storage temp. | 2-8°C |
Product Introduction:
Trifluoroacetic anhydride (TFAA) is an important organic compound with a chemical formula of (CF₃CO)₂O, a molecular weight of 210.03, and a CAS number of 407-25-0. It is a colorless, transparent liquid with a pungent odor, volatile, a melting point of -65°C, a boiling point of 39.5-40.1°C, a relative density of 1.490 (d254), and is soluble in a variety of organic solvents, such as benzene, dichloromethane, ether, N,N-dimethylformamide, tetrahydrofuran, and acetonitrile. Trifluoroacetic anhydride is hygroscopic and will decompose in water and ethanol to produce trifluoroacetic acid. Therefore, it is necessary to strictly control the contact between water and alcohol during storage and use.
There are two main methods for preparing trifluoroacetic anhydride: one is through the reaction of trifluoroacetic acid and dichloroacetic anhydride, the reaction equation is CF₃COOH+(Cl₂CHCO)₂O→(CF₃CO)₂O+Cl₂CHCOOH; the other is the phosphorus pentoxide method, using trifluoroacetic acid and phosphorus pentoxide as raw materials, and reacting in a fully closed state. By controlling the reaction conditions, such as temperature, time and reactant ratio, the purity and yield of the product can be effectively improved, while reducing environmental pollution and production costs.
Trifluoroacetic anhydride is a strong dehydrating agent with a wide range of chemical reactivity. Its structure contains two strong electron-withdrawing groups, trifluoromethyl, which makes it a relatively strong organic anhydride with active chemical properties and great use in organic synthesis. For example, it can react with carboxylic acid to generate the corresponding mixed anhydride, enhance the electrophilicity of the carboxylic acid carbonyl group, and make the carboxylic acid less susceptible to attack by nucleophilic reagents; it can also be used as a dehydrating agent to dehydrate amides, oximes, hydroxy ketones or hydroxy acid esters in the presence of a weak base to generate the corresponding nitriles and unsaturated ketones or carboxylic acid esters; in addition, a mixture of trifluoroacetic anhydride and sodium iodide can be used as a reducing agent, and a mixture with dimethyl sulfoxide can be used as an oxidant.
Trifluoroacetic anhydride needs to be used with caution. It is corrosive and has a strong irritating effect on the skin and mucous membranes. It can cause burns and is classified as a Class 8.1 hazardous chemical. Therefore, the operation must be carried out in a fume hood, and appropriate protective equipment such as gloves, goggles and masks must be worn to avoid inhalation or contact with the skin and eyes. In the event of accidental contact, rinse immediately with plenty of water and seek medical attention in time.
Nature and Specifications:
Item | Specification |
Product Name | Trifluoroacetic Anhydride |
CAS No. | 407-25-0 |
Appearance | Liquid |
Shelf Life | 2 years |
Packing | As your requirements |
pka | 0.43[at 20 ℃] |
form | Liquid |
color | Clear |
Specific Gravity | 1.487 |
Water Solubility | Hydrolysis |
Sensitive | Moisture Sensitive |
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Trifluoroacetic anhydride plays an integral part in organic synthesis due to its versatility. As an acylating agent, activated esters generated from its reaction with carboxylic acids significantly increase electrophilicity of carbonyl groups, and therefore accelerate nucleophilic addition or substitution reactions. Friedel-Crafts reactions play an integral part in the preparation of drug intermediates. For instance, aromatic rings can be acylated using this reaction with up to 98% yield achieved using it. Trifluoroacetic anhydride has also proven its efficiency at converting alcohols, turning primary and secondary alcohols into halogenated hydrocarbons or carbonyl compounds via trifluoroacetate ester intermediates, often in one pot method compared to traditional multi-step synthesis routes.
Trifluoroacetic anhydride often works effectively when combined with other reagents during redox reactions. For instance, using sodium iodide can act as an efficient reducing agent while dimethyl sulfoxide (DMSO) forms an ideal oxidant that allows alcohols to convert to carbonyl compounds. Compare it with traditional Swern oxidant solutions such as DMSO/oxalyl chloride for better tolerance when handling substrates containing sensitive functional groups like halogens. Thus expanding its application in complex molecular synthesis. Trifluoroacetic anhydride acts as a powerful dehydrating agent and is useful in the dehydration of amides, oximes or hydroxyl compounds to form nitriles, unsaturated ketones or carboxylates in the presence of weak bases (such as triethylamine and pyridine). Such reactions provide important steps towards creating natural products and fine chemicals.
Recently, free radical chemistry has given a boost to trifluoroacetic anhydride applications. Visible light catalysis strategies provide a viable means of using trifluoroacetyl radical precursor as a radical initiator to couple with alkyl bromides to form trifluoromethyl ketones efficiently in one step. This method overcomes the dependence of traditional trifluoromethylation reactions on stoichiometric reagents, making them compatible with multiple functional groups like primary to tertiary alkyl bromides, amides and esters – providing an efficient tool for fluorine drug discovery. Trifluoroacetic anhydride and hydrogen peroxide can also be combined to oxidize thiophene derivatives into cyclic sulfone compounds, with potential applications in materials science as well as bioactive molecules.
Trifluoroacetic anhydride’s downstream demand continues to expand rapidly in industry, particularly when used for manufacturing medicines, pesticides and high-end chemicals. Used as an intermediate in drug synthesis to produce active molecules containing trifluoromethyl that can significantly enhance metabolic stability and solubility of medications; trifluoroacetic anhydride also plays a vital role in producing high-efficiency insecticides and herbicides to upgrade agricultural production into green production; its applications also enhance technological innovation within chemical industry.
Trifluoroacetic anhydride serves many different functions as an indispensable multifunctional reagent, including activation, dehydration, oxidation and reduction. Traditional synthetic routes usually involve the replacement of multiple reagents at different reaction steps; trifluoroacetic anhydride makes this much simpler by offering “one dose for multiple uses”, thus simplifying and cutting costs associated with production processes. Dehydration systems made with weak bases offer several advantages over traditional strong acid catalysts; one such advantage lies in realizing amide-to-nitrile conversion under mild conditions while minimizing corrosion and by-product generation. Additionally, its growing use in free radical reactions demonstrates its adaptability, while construction of C-C bonds under mild conditions through photocatalytic strategies is in line with green chemistry’s development trend.
Trifluoroacetic anhydride stands out economically by being easy to obtain raw materials and well-established preparation processes, with major global reagent suppliers being able to stably supply high purity products at price competitive unit costs – making industrial applications possible with price competitiveness in mind. Furthermore, its mild reaction conditions and high yield can reduce waste generation, meet environmental regulations, and are ideal for pharmaceutical and pesticide industries that demand clean production environments.
Trifluoroacetic anhydride has become an indispensable tool in fluorine-containing compound synthesis, playing an indispensable role. Trifluoromethyl can greatly enhance the physical-chemical properties of molecules, including increasing lipid solubility, improving metabolic stability and controlling electronic effects – all which makes trifluoromethyl-containing drug molecules (such as antiviral agents and cancer therapeutics ) highly effective clinically. As an efficient source of trifluoroacetyl groups, trifluoroacetic anhydride allows drug developers to efficiently construct trifluoroacetyl groups more quickly and thus speed up development cycles. Furthermore, trifluoroacetic anhydride can also be used in materials science to synthesize fluorine-containing polymers or coatings with dielectric properties which improve weather resistance, corrosion resistance, dielectric properties of materials as well as meet high-end industrial needs more effectively.
trifluoroacetic anhydride has emerged as a cornerstone reagent in modern organic synthesis and industrial manufacturing due to its high reactivity, functional diversity, and economy. Furthermore, with new technologies like photocatalysis and free radical chemistry integrating more widely, its application boundaries continue to broaden, spurring innovation in medicine, agriculture, materials etc.
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