Trimethylacetic anhydride
Mechanism of Hydrolysis- Product Name
- Trimethylacetic anhydride
- CAS No.
- 1538-75-6
- Chemical Name
- Trimethylacetic anhydride
- Synonyms
- PIVALIC ANHYDRIDE;Bis(2,2-dimethylpropionic)anhydride;Pivalic anydride;Bis(pivalic)anhydride;Pivalic acid anhydride;2,2-Dimethylpropanoicanhydride;2,2-dimethylpropanoyl 2,2-dimethylpropanoate;Pivolic Anhydride;Dipivalic anhydride;PivalicAnhydride>
- CBNumber
- CB9470666
- Molecular Formula
- C10H18O3
- Formula Weight
- 186.25
- MOL File
- 1538-75-6.mol
Trimethylacetic anhydride Property
- 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
- 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
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Danger
- Hazard statements
-
H226Flammable liquid and vapour
H314Causes severe skin burns and eye damage
- Precautionary statements
-
P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.
P233Keep container tightly closed.
P240Ground/bond container and receiving equipment.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- 143502
- Product name
- Trimethylacetic anhydride
- Purity
- 99%
- Packaging
- 25g
- Price
- $64.7
- Updated
- 2026/04/30
- Product number
- 143502
- Product name
- Trimethylacetic anhydride
- Purity
- 99%
- Packaging
- 100g
- Price
- $193
- Updated
- 2026/04/30
- Product number
- P1414
- Product name
- Pivalic Anhydride
- Purity
- >98.0%(GC)
- Packaging
- 25mL
- Price
- $56
- Updated
- 2026/04/30
- Product number
- P1414
- Product name
- Pivalic Anhydride
- Purity
- >98.0%(GC)
- Packaging
- 250mL
- Price
- $280
- Updated
- 2026/04/30
- Product number
- 02352
- Product name
- Trimethylacetic anhydride
- Purity
- 99%
- Packaging
- 25G
- Price
- $74.81
- Updated
- 2026/05/19
Trimethylacetic anhydride Chemical Properties,Usage,Production
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 Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from Trimethylacetic anhydride manufacturers
- Product
- Trimethylacetic anhydride 1538-75-6
- Price
- US $0.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 1
- Release date
- 2025-09-26
- Product
- Pivalic anhydride 1538-75-6
- Price
- US $13.00/kg
- Min. Order
- 1kg
- Purity
- 99.0%
- Supply Ability
- 1000MT
- Release date
- 2024-01-24
- Product
- Trimethylacetic Anhydride 1538-75-6
- Price
- US $180.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 20ton
- Release date
- 2024-06-05