684-78-6

Basic information

• Product Name: N,O-BIS(TRIFLUOROACETYL)HYDROXYLAMINE
• Synonyms: O,N-BIS(TRIFLUOROACETYL)HYDROXYLAMINE;N,O-BIS(TRIFLUOROACETYL)HYDROXYLAMINE;2,2,2-trifluoro-n-[(trifluoroacetyl)oxy]-acetamid;trifluoroacetic trifluoroacetohydroxamic anhydride;N,O-Bis(trifluoroacetyl)hydroxylamine 97%;N,O-Bis(trifluoroacetyl)hydroxylamine97%;2,2,2-Trifluoro-N-[(trifluoroacetyl)oxy]acetamide;N-(Trifluoroacetoxy)-2,2,2-trifluoroacetamide
• CAS NO: 684-78-6
• Molecular Formula: C₄HF₆NO₃
• Molecular Weight: 225.05
• EINECS: 211-677-9
• Product Categories: Hydroxylamines;Hydroxylamines (N-Substituted);Hydroxylamines (O-Substituted)
• Mol File: 684-78-6.mol
• Article Data: 5

Chemical Properties

• Melting Point: 59-60°C
• Appearance: /
• Density: 1.645 g/cm³
• Refractive Index: 1.316
• Storage Temp.: Refrigerator
• CAS DataBase Reference: N,O-BIS(TRIFLUOROACETYL)HYDROXYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: N,O-BIS(TRIFLUOROACETYL)HYDROXYLAMINE(684-78-6)
• EPA Substance Registry System: N,O-BIS(TRIFLUOROACETYL)HYDROXYLAMINE(684-78-6)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 24/25-26-36/37/39
• RIDADR: 3261
• HazardClass: CORROSIVE
• Hazardous Substances Data: 684-78-6(Hazardous Substances Data)

Usage

Description

N,O-Bis(trifluoroacetyl)hydroxylamine is a chemical compound belonging to the class of organic compounds known as acetamides, specifically a tertiary amide. It is a derivative of hydroxylamine and is characterized by a hydroxylamine functional group and two trifluoroacetyl functional groups. This colorless crystalline solid is typically used in scientific research for specialized chemical reactions and is known for its role in the synthesis of nitrogen-containing compounds. Its IUPAC name is N,N-Bis(trifluoroacetyl)hydroxylamine.

Uses

Used in Chemical Synthesis:
N,O-Bis(trifluoroacetyl)hydroxylamine is used as a reagent in the synthesis of nitrogen-containing compounds due to its unique functional groups and properties.
Used in Scientific Research:
In the field of scientific research, N,O-Bis(trifluoroacetyl)hydroxylamine is employed as a specialized chemical for conducting various chemical reactions, contributing to the advancement of chemical knowledge and the development of new compounds.
Used in Pharmaceutical Industry:
N,O-Bis(trifluoroacetyl)hydroxylamine may be utilized in the pharmaceutical industry for the development of new drugs, given its role in the synthesis of nitrogen-containing compounds, which are common in many pharmaceutical agents.
Used in Material Science:
In material science, N,O-Bis(trifluoroacetyl)hydroxylamine could be employed in the development of new materials with specific properties, such as those with enhanced stability or reactivity, due to its unique chemical structure.

InChI:InChI=1/C4HF6NO3/c5-3(6,7)1(12)11-14-2(13)4(8,9)10/h(H,11,12)

Upstream product

• 407-25-0 trifluoroacetic anhydride 

Downstream Products

• 2024-83-1 veratronitrile 
• 629-08-3 heptanenitrile 
• 619-24-9 3-nitrobenzonitrile 
• 773-82-0 Pentafluorobenzonitrile 
• 611-20-1 salicylonitrile 
• 1885-38-7 cinnamic nitrile 
• 874-90-8 4-methoxybenzonitrile 

Relevant articles and documents

N,O-bis(trifluoroacetyl)hydroxylamine as a useful electrophilic nitrogen source: Catalytic synthesis of N-(trifluoroacetyl)sulfilimines

(equation presented) In the presence of catalytic quantites of Cu(OTf)2 the novel hydroxamic acid anhydride salt functions competently in the trifluoroacetamidation of sulfides to afford N-(trifluoroacetyl)sulfilimines. The salient features of this salt include its ease of synthesis from the inexpensive, commercially available starting materials trifluoroacetic anhydride and hydroxylamine hydrochloride.

ENCHAINEMENTS HETEROATOMIQUES ET LEURS PRODUITS DE CYCLISATION - VIII METHYLENE-2-DIHYDRO-3,6-2H-THIAZINES-1,3-FONCTIONNALISEES EN POSITION 4 PAR SUBSTITUTION NUCLEOPHILE D'UN GROUPEMENT BROMOMETHYLE ET PAR CONVERSION D'UN GROUPEMENT DIBROMOMETHYLENE EN ALDEHYDE, NITRILE ET ESTER

Treatment with NBS of 2-methylene-3,6-dihydro-2H-1,3-thiazines carrying an ester function on 5 and a methyl on 4 gives the corresponding 4-bromomethyl and 4,4-dibromomethyl derivatives in a perfectly selective manner.The monobromo compounds give access to 4-aminomethyl, 4-alkoxymethyl, 4-alkylthiomethyl, 4-acetoxymethyl and 4-formyl thiazines.These aldehydes, also prepared from the dibromo derivatives, are converted into 4-cyano and 4-alkoxycarbonyl thiazines.In certain cases, interactions with the neighbouring ester group, leading to lactones are observed.

Trifluoroacetonitrile Oxide

Trifluoroacetonitrile oxide (1) is a reactive intermediate that can be generated by the dehydrochlorination of trifluoroacetohydroximoyl chloride (2) with base.It reacts with mercaptans and amines in a stereospecific manner to give Z oximes 3 and 15 and forms a cycloadduct (10) with benzonitrile.In the absence of trapping agents, it dimerizes to give either the expected furoxan dimer 7 or the unusual dioxadiazine dimer 8, depending upon conditions.A convenient synthesis for 2 based on hydroxylamine hydrochloride, trifluoroacetic anhydride, and PCl3 was developedto make 1 easily accessible.