| Identification | More | [Name]
TRIMETHYLACETIC ANHYDRIDE | [CAS]
1538-75-6 | [Synonyms]
2,2-DIMETHYLPROPIONIC ACID ANHYDRIDE
2,2-DIMETHYLPROPIONIC ANHYDRIDE
BIS(TRIMETHYLACETIC) ANHYDRIDE
PIVALIC ANHYDRIDE
TRIMETHYLACETIC ACID ANHYDRIDE
TRIMETHYLACETIC ANHYDRIDE
1,1-Dimethylpropanoic anhydride
2,2-dimethyl-propanoicacianhydride
2,2-Dimethylpropanoicanhydride
Pivalic anydride
Propanoic acid, 2,2-dimethyl-, anhydride
Propanoicacid,2,2-dimethyl-,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
Dipivalic anhydride
Pivalic acid anhydride | [EINECS(EC#)]
216-263-1 | [Molecular Formula]
C10H18O3 | [MDL Number]
MFCD00008842 | [Molecular Weight]
186.25 | [MOL File]
1538-75-6.mol |
| Chemical Properties | Back Directory | [Appearance]
clear colourless liquid | [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.)
| [Fp ]
135 °F
| [storage temp. ]
Store at RT. | [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 Data | Back Directory | [Symbol(GHS) ]
 
GHS02,GHS05 | [Signal word ]
Danger | [Hazard statements ]
H226-H314 | [Precautionary statements ]
P210-P233-P240-P280-P303+P361+P353-P305+P351+P338 | [Hazard Codes ]
C | [Risk Statements ]
R34:Causes burns. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [RIDADR ]
UN 2920 8/PG 2
| [WGK Germany ]
3
| [F ]
9-13-21 | [TSCA ]
Yes | [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 |
| Questions And Answer | Back Directory | [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]. |
| Hazard Information | Back Directory | [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]
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
| [Uses]
A metabolite of a double prodrug (6-dGCV-DPiv | [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]
Notclassified | [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 |
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