2,2-dimethylpropanoyl 2,2-dimethylpropanoate

• ChemBase ID: 112723
• Molecular Formular: C10H18O3
• Molecular Mass: 186.24812
• Monoisotopic Mass: 186.12559444
• SMILES: CC(C)(C)C(=O)OC(=O)C(C)(C)C
• Canonical SMILES: O=C(C(C)(C)C)OC(=O)C(C)(C)C
• InChI: InChI=1S/C10H18O3/c1-9(2,3)7(11)13-8(12)10(4,5)6/h1-6H3
• InChIKey: PGZVFRAEAAXREB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,2-dimethylpropanoyl 2,2-dimethylpropanoate
• IUPAC Traditional name: trimethylacetic anhydride
• Synonyms: PIVALIC ANHYDIRIDE; Pivalic anhydride; 2,2-Dimethylpropionic anhydride; Pivalic anhydride; Trimethylacetic anhydride; Pivalic anhydride; 2,2-Dimethylpropanoic Acid 1,1'-Anhydride; 2,2,2-Trimethylacetic Anhydride; 2,2-Dimethylpropanoyl Anhydride; Neopentanoic Anhydride; Pivalic Acid Anhydride; Pivaloyl Anhydride; Trimethylacetic Anhydride; 特戊酸酐; 2,2-二甲基丙酸酐; 特戊酸酐; 三甲基乙酸酐

Database IDs

• CAS Number: 1538-75-6
• EC Number: 216-263-1
• MDL Number: MFCD00008842
• Beilstein Number: 386552
• PubChem SID: 162097636; 24887588; 24848589
• PubChem CID: 15234

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 3.2865534
• LogD (pH = 7.4): 3.2865534
• Log P: 3.2865534
• Molar Refractivity: 49.4868 cm^3
• Polarizability: 19.997911 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 193 °C(lit.); 193°C
• Flash Point: 134.6 °F; 57 °C; 63°C(145°F)
• Density: 0.918; 0.918 g/mL at 25 °C(lit.)
• Refractive Index: 1.4090; n20/D 1.409; n20/D 1.409(lit.)

Safety Information

• Storage Condition: Refrigerator
• Storage Warning: Moisture Sensitive
• European Hazard Symbols: Corrosive (C)
• UN Number: 2920; UN3265
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2; III
• Risk Statements: 34
• Safety Statements: 26-36/37/39-45
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H226-H314; H314-H318-H227
• GHS Precautionary statements: P280-P305 + P351 + P338-P310; P280-P305+P351+P338-P309-P310
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2920 8/PG 2

Product Information

• Purity: ≥98.0% (GC); 95+%; 99%
• Grade: purum
• Linear Formula: [(CH3)3CCO]2O

DETAILS

MP Biomedicals - 05225502

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 143502

Packaging
25, 100 g in glass bottle
Application
Acylation and esterification reagent for anilines1,2 and phenols,3,4 respectively.

Toronto Research Chemicals - T795760

A metabolite of a double prodrug (6-dGCV-DPiv) of Ganciclovir (G235000).

REFERENCES

• Krasny, H.C., et al.: Drug Metab. Dispos., 23, 1242 (1995)
• The direct hydrogenation of carboxylic acids to aldehydes has been achieved in the presence of pivalic anhydride and Tetrakis(triphenylphosphine)palladium(0), 10548: Chem. Lett., 1143 (1998).
• Alcohols can be protected as their pivaloyl (Pv) esters by reaction with the anhydride in the presence of MgBr₂ - Et₃N or Sc(OTf)₃ in acetonitrile: J. Org. Chem., 61, 5702 (1996). See also Trimethylacetyl chloride, A15051.