Trimethylacetyl chloride

• Catalog No.: A15051
• CAS Number: 3282-30-2
• M. F.: C5H9ClO
• M. W.: 120.57736
• Purity: 98+%

SYNONYMS

• Title: 三甲基乙酰氯
• IUPAC name: 2,2-dimethylpropanoyl chloride
• IUPAC Traditional name: 2,2-dimethylpropanoyl chloride
• Synonyms: Pivaloyl chloride

DATABASE IDS

• Beilstein Number: 385668
• CAS Number: 3282-30-2
• MDL Number: MFCD00000709
• EC Number: 221-921-6

PROPERTIES

• Purity: 98+%
• Boiling Point: 105-106°C
• Density: 0.985
• Flash Point: 8°C(46°F)
• Melting Point: -57°C
• Refractive Index: 1.4120
• GHS Hazard statements: H225-H301-H330-H314-H318
• European Hazard Symbols: Highly toxic (T+)
• European Hazard Symbols: Flammable (F)
• GHS Precautionary statements: P210-P301+P310-P303+P361+P353-P304+P340-P305+P351+P338-P320-P330-P405-P501A
• Risk Statements: 11-14-22-26-34
• Safety Statements: 4-8-9-16-20-23-26-28-30-33-36/37/39-45
• Storage Warning: Moisture Sensitive
• TSCA Listed: 是
• Hazard Class: 6.1
• UN Number: UN2438
• Packing Group: I

REFERENCES

• In the presence of Cu(I) halides, reacts with Grignard and organolithium reagents to give t-butyl ketones: Tetrahedron Lett., 829 (1971).
• Activates heteroaromatic amines to ring-lithiation. For example: Synthesis, 670 (1986):
  
• Reacts with sodium formate to give the mixed formic pivalic anhydride, a highly effective reagent for N-formylation: Rec. Trav. Chim., 101, 460 (1982). Similarly, has been used to form mixed anhydrides, particularly of N-protected amino acids and peptides, prior to coupling: Coll. Czech. Chem. Commun., 27, 1273 (1962). The sterically-hindered nature of the pivaloyl group greatly reduces attack at the 'wrong' carbonyl group. For peptide reagents, see Appendix 6.
• Has also been used as a reagent for protection of alcohols as their pivaloyl (Pv) esters, allowing selective acylation of a primary over a secondary alcohol: Synthesis, 453 (1986); selective protection of the less hindered of two primary alcohols is possible: J. Chem. Soc., Chem. Commun., 354 (1988). See also Trimethylacetic anhydride, B22983. Cleavage is by room temperature basic hydrolysis: Tetrahedron Lett., 317 (1973); 3561 (1979); J. Org. Chem., 42, 918 (1977), or methanolysis: J. Am. Chem. Soc., 112, 3693 (1990), or a number of other methods, including aqueous methylamine: Tetrahedron, 24, 639 (1968).