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

General Description

N,O-Bis(trifluoroacetyl)hydroxylamine is a chemical compound that belongs to the class of organic compounds known as acetamides, specifically, a tertiary amide. It is a derivative of the more general compound, hydroxylamine, and is typically used in scientific research for a variety of specialised chemical reactions. Structurally, it is characterized by both a hydroxylamine functional group and two trifluoroacetyl functional groups. It is known for its role in the synthesis of nitrogen-containing compounds. Its physical characteristics include its colorless appearance and the crystalline solid form at room temperature. Its IUPAC name is N,N-Bis(trifluoroacetyl)hydroxylamine.

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

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

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.