Trimethylacetyl chloride, 98+%

Name: Trimethylacetyl chloride, 98+%
SKU: A15051.AP

CAS: 3282-30-2 | C5H9ClO | 120.58 g/mol

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產品號碼 A15051.AP

亦稱為 A15051-AP

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Quantity:

500 mL

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化學識別

CAS3282-30-2

IUPAC Name2,2-dimethylpropanoyl chloride

Molecular FormulaC5H9ClO

InChI KeyJVSFQJZRHXAUGT-UHFFFAOYSA-N

SMILESCC(C)(C)C(Cl)=O

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規格

規格表

Appearance (Color)Clear colorless

FormLiquid

Assay (GC)≥98.0%

CommentSpecification differs for U.S. and non-U.S. material where indicated

Identification (FTIR)Conforms (non-U.S. specification)

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Trimethylacetyl chloride is used as a precursor in the preparation of tert-butyl peroxypivalate, guttiferon A derivatives, which is potential for the treatment of malaria. It is used as a raw material in the production of synthetic acidamide medicament and phenol ester medicament. In addition to this, it is used for the synthesis of active pharmaceutical ingredients such as aminobenzylpenicilin, cephalexin, cefazolin, dipivefrin and dipivalyl epinephrine. It is also used in heavy polymerization, N-acylating agent for amines, Schiff bases, pyrrolidinones as well as an O-acylating agent for alcohols, lactones and saccharides.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

Applications
Trimethylacetyl chloride is used as a precursor in the preparation of tert-butyl peroxypivalate, guttiferon A derivatives, which is potential for the treatment of malaria. It is used as a raw material in the production of synthetic acidamide medicament and phenol ester medicament. In addition to this, it is used for the synthesis of active pharmaceutical ingredients such as aminobenzylpenicilin, cephalexin, cefazolin, dipivefrin and dipivalyl epinephrine. It is also used in heavy polymerization, N-acylating agent for amines, Schiff bases, pyrrolidinones as well as an O-acylating agent for alcohols, lactones and saccharides.

Solubility
Miscible with acetonitrile.

Notes
Moisture sensitive. Incompatible withalcohols, oxidizing agents and strong bases.

RUO – Research Use Only

General References:

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 Trimethyl acetic 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).
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):
Moon, S. Y.; Jung, S. H.; Kim, U. B.; Kim, W. S. Synthesis of ketones via organolithium addition to acid chlorides using continuous flow chemistry. RSC Adv. 2015, 5 (97), 79385-79390.
Frömmel, J.; Šebela, M.; Demo, G.; Lenobel, R.; Pospíšil, T.; Soural, M.; Kopečný, D. N-acyl-μ-aminoaldehydes are efficient substrates of plant aminoaldehyde dehydrogenases. Amino Acids 2015, 47 (1), 175-187.