Trimethylacetic anhydride Chemical Properties

Boiling point:

193 °C(lit.)

Density 

0.918 g/mL at 25 °C(lit.)

vapor pressure 

62.1Pa at 25℃

refractive index 

n20/D 1.409(lit.)

Flash point:

135 °F

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Miscible with acetonitrile.

form 

Liquid

color 

Clear colorless

Sensitive 

Moisture Sensitive

BRN 

386552

InChI

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

InChIKey

PGZVFRAEAAXREB-UHFFFAOYSA-N

SMILES

C(C)(C)(C)C(=O)OC(=O)C(C)(C)C

LogP

2.15

CAS DataBase Reference

1538-75-6(CAS DataBase Reference)

EPA Substance Registry System

Propanoic acid, 2,2-dimethyl-, anhydride (1538-75-6)

Safety Information

Hazard Codes 

C

Risk Statements 

34

Safety Statements 

26-36/37/39-45

RIDADR 

UN 2920 8/PG 2

WGK Germany 

3

F 

9-13-21

TSCA 

TSCA listed

HazardClass 

8

PackingGroup 

II

HS Code 

29159000

Storage Class

10 - Combustible liquids

Hazard Classifications

Acute Tox. 4 Oral
Eye Irrit. 2
Skin Irrit. 2
Skin Sens. 1
STOT SE 3

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Trimethylacetic anhydride Usage And Synthesis

Mechanism of Hydrolysis

The acid hydrolysis of trimethylacetic anhydride follows an A-2 mechanism in both water and aqueous dioxane and is slower than that of acetic anhydride. acetic anhydride also follows an A-2 mechanism.

These observations suggest that the acid hydrolysis of Perchloric, sulfuric, and hydrochloric acid catalyze hydrolysis to different extents, and plots of the logarithms of the rate constants against log [H+] or Ho are curved. These reactions are likely to involve a bimolecular attack by water molecules on the anhydride or its conjugate acid, as the methyl group is expected to hinder the incoming nucleophile through steric hindrance and, possibly, through inductive effects[1].

Description

Trimethylacetic anhydride is a pivalic acid derivative that is used in organic synthesis. The compound's reaction mechanism is believed to be the formation of an alkanoic acid, which reacts with a hydroxyl group to form an anhydride. Trimethyl acetic anhydride has been shown to have pharmacokinetic properties and can be used as a nonsteroidal anti-inflammatory drug. This compound has also been found to have a matrix effect on crystalline cellulose and is capable of forming nitrogen-containing carboxylic acids.

Chemical Properties

clear colourless liquid

Uses

A metabolite of a double prodrug (6-dGCV-DPiv

Uses

Trimethylacetic anhydride was used:

• in solid-phase oligonucleotide synthesis
• in kinetic resolution of racemic 2-hydroxy-γ-butyrolactones with diphenylacetic acid
• as acylation and esterification reagent for anilines
• as acylation and esterification reagent for phenols

Application

Trimethylacetic anhydride (TMA) as a new reagent for efficient histone derivatization, which is a requirement for bottom-up proteomic hPTM analysis. TMA can derivatize unmodified amine groups of lysine residues and amine groups generated at peptide N-termini by trypsin digestion. It afforded over 98% and 99% labelling efficiencies for histones H4 and H3 respectively, thereby enabling accurate quantification of the peptide forms[2].

Flammability and Explosibility

Not classified

References

[1] C. A. Bunton, & J. H. F. (1965). The Hydrolysis of Carboxylic Anhydrides. V.1,2 The Acid Hydrolysis of Acetic and Trimethylacetic Anhydride. Journal of Organic Chemistry, 30 5, 1365–1371. https://doi.org/10.1021/jo01016a006
[2] Hana Kuchaříková. (2021). Trimethylacetic Anhydride-Based Derivatization Facilitates Quantification of Histone Marks at the MS1 Level. ACS Applied Nano Materials, 100114. https://doi.org/10.1016/j.mcpro.2021.100114

Trimethylacetic anhydride(1538-75-6)Related Product Information

• Iodomethyl pivalate
• Pivalic acid
• silver pivalate
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• PotassiuM triMethylacetate, 95%
• Pivaldehyde
• Ethyl trimethylacetate
• DIISOBUTYL ETHER
• Isobutyl propionate
• Isobutyl isobutyrate
• ISOBUTYRIC ACID N-PROPYL ESTER
• VALERIC ANHYDRIDE
• Propionic anhydride
• Methyl trimethylacetate
• Isobutyl acetate
• Isobutyl formate
• TRIMETHYLACETIC ANHYDRIDE