16649-49-3

Basic information

• Product Name: ACETIC ANHYDRIDE-D6
• Synonyms: Acetic-d3 acid, anhydride;Acetic anhydride-D6 98.5 atom % D;Bis(2,2,2-2H3)acetic anhydride;Bis[(2,2,2-2H3)acetic acid]anhydride;Di[(2,2,2-2H3)acetic]anhydride;Acetic anhydride-d6,for NMR,98.5 atom % D;-acetic anhydride;ACETIC ANHYDRIDE-D6
• CAS NO: 16649-49-3
• Molecular Formula: C₄H₆O₃
• Molecular Weight: 108.13
• EINECS: 240-697-0
• Product Categories: A;Alphabetical Listings;Stable Isotopes
• Mol File: 16649-49-3.mol
• Article Data: 4

Chemical Properties

• Melting Point: -73 °C(lit.)
• Boiling Point: 138-140 °C(lit.)
• Flash Point: 130 °F
• Appearance: Clear colorless/Liquid
• Density: 1.143 g/mL at 25 °C
• Vapor Pressure: 5.94mmHg at 25°C
• Refractive Index: n20/D 1.3875(lit.)
• Storage Temp.: Flammables area
• Stability: Stable, but reacts violently with water. Combustible. Incompatible with strong oxidising agents, alcohols, strong bases.
• BRN: 1910689
• CAS DataBase Reference: ACETIC ANHYDRIDE-D6(CAS DataBase Reference)
• NIST Chemistry Reference: ACETIC ANHYDRIDE-D6(16649-49-3)
• EPA Substance Registry System: ACETIC ANHYDRIDE-D6(16649-49-3)

Safety Data

• Hazard Codes: C
• Statements: 10-34-20/22
• Safety Statements: 26-45-36/37/39
• RIDADR: UN 1715 8/PG 2
• WGK Germany: 3
• F: 10-21
• Hazardous Substances Data: 16649-49-3(Hazardous Substances Data)

Usage

Chemical Properties

colourless liquid

Uses

Acetic Anhydride-d6 is the labeled analog of acetic anhydride, a reagent used generally in acetylation reactions in organic chemistry, primarily cellulose acetate and film material.

InChI:InChI=1/C4H6O3/c1-3(5)7-4(2)6/h1-2H3/i1D3,2D3

Upstream product

• 1186-52-3 tetradeuterioacetic acid 
• 56-81-5 glycerol 
• 81408-98-2 p-nitrophenyl acetate-d3 
• 1941-22-6 CD₃COO^(1-)*K⁽¹⁺⁾=CD₃COOK 
• 19259-90-6 [2H₃]acetyl chloride 
• 14044-94-1 sodium trideuterioacetate 

Downstream Products

• 42198-69-6 (E)-3-deuteriocinnamic acid 
• 122570-76-7 trans-<α,β-2H2>cinnamic acid 
• 126295-06-5 methyl 3-O-<2,2,2-D3>acetyl-2,4,6-tri-O-benzoyl-β-D-galactopyranoside 
• 80949-93-5 methyl 6,2',3'-tri-O-acetyl-2,3,4'-tri-O-trideuterioacetyl-6'-O-trityl-β-cellobioside 
• 80949-92-4 methyl 6,2',3',4'-tetra-O-acetyl-2,3-di-O-trideuterioacetyl-6'-O-trityl-β-cellobioside 
• 80949-91-3 methyl 2,6,3',4'-tetra-O-acetyl-3,2'-di-O-trideuterioacetyl-6'-O-trityl-β-cellobioside 
• 80949-90-2 methyl 2,6,2',3'-tetra-O-acetyl-3,4'-di-O-trideuterioacetyl-6'-O-trityl-β-cellobioside 
• 80949-86-6 1,2,6,2',3'-penta-O-acetyl-3,4'-di-O-trideuterioacetyl-6'-O-trityl-α-cellobiose 
• 80949-89-9 methyl 2,6,2',3',4'-penta-O-acetyl-3-O-trideuterioacetyl-6'-O-trityl-β-cellobioside 
• 80949-88-8 methyl 2,3,2',3',4'-penta-O-acetyl-6-O-trideuterioacetyl-6'-O-trityl-β-cellobioside 
• 80949-87-7 methyl 2,3,6,2',3'-penta-O-acetyl-4'-O-trideuterioacetyl-6'-O-trityl-β-cellobioside 
• 80949-85-5 1,2,6,2',3',4'-hexa-O-acetyl-3-O-trideuterioacetyl-6'-O-trityl-α-cellobiose 
• 80956-50-9 methyl 2',3'-di-O-acetyl-2,3,4'-tri-O-trideuterioacetyl-6,6'-di-O-trityl-β-cellobioside 
• 80956-49-6 methyl 2,3'-di-O-acetyl-3,2',4'-tri-O-trideuterioacetyl-6,6'-O-trityl-β-cellobioside 

Relevant articles and documents

A transesterification-acetalization catalytic tandem process for the functionalization of glycerol: The pivotal role of isopropenyl acetate

At 30 °C, in the presence of Amberlyst-15 as a catalyst, a tandem sequence was implemented by which a pool of innocuous reactants (isopropenyl acetate, acetic acid and acetone) allowed upgrading of glycerol through selective acetylation and acetalization processes. The study provided evidence for the occurrence of multiple concomitant reactions. Isopropenyl acetate acted as a transesterification agent to provide glyceryl esters, and it was concurrently subjected to an acidolysis reaction promoted by AcOH. Both these transformations co-generated acetone which converted glycerol into the corresponding acetals, while acidolysis sourced also acetic anhydride that acted as an acetylation reactant. However, tuning of conditions, mostly by changing the reactant molar ratio and optimizing the reaction time, was successful to steer the set of all reactions towards the synthesis of either a 1?:?1 mixture of acetal acetates (97% of which was solketal acetate) and triacetin, or acetal acetates in up to 91% yield, at complete conversion of glycerol. To the best of our knowledge, a one-pot protocol with such a degree of control on the functionalization of glycerol via transesterification and acetalization reactions has not been previously reported. The procedure was also easily reproduced on a gram scale, thereby proving its efficiency for preparative purposes. Finally, the design of experiments with isotopically labelled reagents, particularly d4-acetic acid and d6-acetone, helped to estimate the contribution of different reaction partners (iPAc/AcOH/acetone) to the formation of final products. This journal is

Reinvestigation of a Synthesis of (R,S)-Mevalonolactone

An n.m.r. study of the reaction of 3-hydroxy-3-methylpentane-1,5-dioic acid (5) with excess of acetic anhydride is described.It has shown that 3-hydroxy-3-methylpentane-1,5-dioic acid anhydride (2), previously described by Scott and Shishido as an intermediate in their synthesis of mevalonolactone, is formed only transiently, along with 3-acetoxy-3-methylpentane-1,5-dioic acid (6).Both intermediates eventually give 3-acetoxy-3-methylpentane-1,5-dioic acid anhydride (3).To obtain (R,S)-mevalonolactone, sodium borohydride reduction of 3-hydroxy-3-methylpentane-1,5-dioic acid anhydride (2), prepared from the diacid (5) and N,N-dicyclohexylcarbodi-imide, is shown to be better than reduction of 3-acetoxy-3-methylpentane-1,5-dioic acid anhydride (3).