1538-75-6

Basic information

• Product Name: TRIMETHYLACETIC ANHYDRIDE
• Synonyms: BIS(TRIMETHYLACETIC) ANHYDRIDE;2,2-DIMETHYLPROPIONIC ACID ANHYDRIDE;2,2-DIMETHYLPROPIONIC ANHYDRIDE;2,2-Dimethylpropionic anhydride, Pivalic anhydride;Bis(2,2-dimethylpropionic acid)anhydride;Bis(2,2-dimethylpropionic)anhydride;Bis(pivalic acid)anhydride;Bis(pivalic)anhydride
• CAS NO: 1538-75-6
• Molecular Formula: C₁₀H₁₈O₃
• Molecular Weight: 186.25
• EINECS: 216-263-1
• Product Categories: Aliphatics;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Aliphatics, Metabolites & Impurities, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 1538-75-6.mol
• Article Data: 41

Chemical Properties

• Boiling Point: 193 °C(lit.)
• Flash Point: 135 °F
• Appearance: Clear colorless/Liquid
• Density: 0.918 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.475mmHg at 25°C
• Refractive Index: n20/D 1.409(lit.)
• Storage Temp.: Store at RT.
• Solubility: Miscible with acetonitrile.
• Sensitive: Moisture Sensitive
• BRN: 386552
• CAS DataBase Reference: TRIMETHYLACETIC ANHYDRIDE(CAS DataBase Reference)
• NIST Chemistry Reference: TRIMETHYLACETIC ANHYDRIDE(1538-75-6)
• EPA Substance Registry System: TRIMETHYLACETIC ANHYDRIDE(1538-75-6)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 2920 8/PG 2
• WGK Germany: 3
• F: 9-13-21
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 1538-75-6(Hazardous Substances Data)

Usage

Description

TRIMETHYLACETIC ANHYDRIDE is a clear, colorless liquid that serves as a versatile reagent in various chemical reactions and applications due to its anhydride structure.

Uses

Used in Pharmaceutical Industry:
TRIMETHYLACETIC ANHYDRIDE is used as a prodrug metabolite for the development of double prodrugs, such as 6-dGCV-DPiv. This application aids in enhancing the drug's bioavailability and therapeutic efficacy.
Used in Chemical Synthesis:
TRIMETHYLACETIC ANHYDRIDE is used as an acylation and esterification reagent for anilines. This application is crucial in the synthesis of various organic compounds and pharmaceuticals, as it helps in the formation of amide and ester linkages.
Used in Chemical Synthesis (continued):
TRIMETHYLACETIC ANHYDRIDE is also used as an acylation and esterification reagent for phenols. This application is essential in the synthesis of a wide range of phenolic compounds, which have diverse applications in the chemical, pharmaceutical, and material science industries.
Used in Oligonucleotide Synthesis:
TRIMETHYLACETIC ANHYDRIDE is used in solid-phase oligonucleotide synthesis, a technique employed in the production of DNA and RNA fragments. This application is vital for research, diagnostics, and therapeutics in the field of molecular biology.
Used in Enzyme Kinetic Resolution:
TRIMETHYLACETIC ANHYDRIDE is used in the kinetic resolution of racemic 2-hydroxy-γ-butyrolactones with diphenylacetic acid. This application is significant in the production of enantiomerically pure compounds, which are essential in the pharmaceutical industry for the development of chiral drugs with improved efficacy and reduced side effects.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C10H18O3/c1-9(2,3)7(11)13-8(12)10(4,5)6/h1-6H3

Upstream product

• 677-22-5 tert-butylmagnesium chloride 
• 3282-30-2 pivaloyl chloride 
• 75-98-9 Trimethylacetic acid 
• 75-36-5 acetyl chloride 
• 6443-91-0 ethynyl methyl ether 
• 80057-39-2 thallium(I) 2,2-dimethylpropanoate 
• 19820-60-1 Benzoic trimethylacetic anhydride 
• 630-19-3 pivalaldehyde 
• 65-85-0 benzoic acid 
• 98-73-7 4-(1,1-dimethylethyl)benzoic acid 
• 50-43-1 2,4,6-trichlorobenzoic acid 
• 50-84-0 2,4 dichlorobenzoic acid 
• 92-92-2 biphenyl-4-carboxylic acid 
• 535-80-8 3-chlorobenzoate 

Downstream Products

• 142645-50-9 6-methyl-2-pivaloylamino-4(3H)-pteridinone 
• 82247-50-5 3-pivaloxy-6-ethyl-2-cyclohexen-1-one 
• 82247-51-6 3-pivaloxy-4-ethyl-2-cyclohexen-1-one 
• 82212-47-3 <(Pivalyloxy)methoxy>benzene 
• 866605-70-1 [1-(2,2-Dimethyl-propionylamino)-2-phenyl-ethyl]-phosphonic acid 
• 866605-69-8 [(2,2-Dimethyl-propionylamino)-phenyl-methyl]-phosphonic acid 
• 137601-34-4 (2R,5S)-2-isopropyl-5-methyl-cyclohexyl 2,2-dimethylpropanoate 
• 30314-46-6 1-(3,4-dimethoxyphenyl)-2,2-dimethylpropan-1-one 
• 181260-67-3 1-(4-methoxy-3-methyl-phenyl)-2,2-dimethyl-propan-1-one 
• 132836-68-1 (S)-3-(tert-butoxycarbonyl)-4-benzyl-2-oxazolidinone 
• 185426-06-6 (1S,2R,1'R)-(-)-N-<2-(2'-tert-butoxycarbonylamino-1'-methylethoxy)-1-methyl-2-phenylethyl>formamide 
• 185426-07-7 (1S,2R,1'R)-(-)-N-<2-(1'-tert-butoxycarbonylaminomethylpropoxy)-1-methyl-2-phenylethyl>formamide 
• 185426-09-9 (1S,2R,1'R)-(-)-N-<2-(1'-tert-butoxycarbonylaminomethyl-2',2'-dimethylpropoxy)-1-methyl-2-phenylethyl>formamide 
• 185426-08-8 (1S,2R,1'R)-(-)-N-<2-(1'-tert-butoxycarbonylaminomethyl-2'-methylpropoxy)-1-methyl-2-phenylethyl>formamide 

Relevant articles and documents

Reactions of Tris(dialkylamino)phosphines with Carbonyl Compounds

The reactions of hexamethylphosphorous triamide and some cyclic analogues with anhydrides, acid chorides, and esters are reported.A mechanism is postulated which involves nucleophilic attack of trivalent phosphorus upon the carbonyl carbon, followed by phosphorane formation and a concerted fragmentation to products.

Electrochemical Reduction of Trimethylacetyl Chloride at Carbon and Mercury Electrodes in Acetonitrile

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PPh3/Selectfluor-Mediated Transformation of Carboxylic Acids into Acid Anhydrides and Acyl Fluorides and Its Application in Amide and Ester Synthesis

By taking the advantage of PPh3/Selectfluor system, carboxylic acids are efficiently converted into the pivotal intermediates acyloxyphosphonium ions that can selectively react with a second carboxylic acid or fluoride to in situ yield the corresponding acid anhydrides or acyl fluorides. The developed protocol features commercially availabile reagents, no involvement of base, room temperature conditions, and simple experimental procedure. Additionally, various amides or esters are readily achieved, respectively, with the addition of amines or alcohols.

METHOD FOR PRODUCING CARBOXYLIC ACID ANHYDRIDE AND METHOD FOR PRODUCING CARBOXYLIC ACID ESTER

Provided is a production method whereby corresponding carboxylic acid anhydrides and carboxylic acid esters can be obtained at high yield from various carboxylic acids even without a solvent and near room temperature. A method for producing a carboxylic acid anhydride represented by formula (II), the method comprising reacting a compound represented by formula (I) and a carboxylic acid in the presence of a Group II metal compound having an ionic ligand containing an oxygen atom. A method for producing a carboxylic acid ester, the method comprising reacting a carboxylic acid anhydride produced by the aforementioned method and an alcohol. In formula (I), R1 represents a C1-20 hydrocarbon group. In formula (II), R2 represents a C1-20 hydrocarbon group.