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3282-30-2 - Trimethylacetyl chloride, 98+% - Pivaloyl chloride - A15051 - Alfa Aesar

A15051 Trimethylacetyl chloride, 98+%

Codice CAS
3282-30-2
Sinonimi
Pivaloyl chloride

Dimensioni Prezzo ($) Quantità Disponibilità
100ml 14,94
500ml 51,09
2500ml 177,30
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Trimethylacetyl chloride, 98+%

MDL
MFCD00000709
EINECS
221-921-6

Proprietà chimiche

Formula
(CH3)3CCOCl
Peso formula
120.58
Punto di fusione
-57°
Punto di ebollizione
105-106°
Punto di infiammabilità
8°(46°F)
Densità
0.985
Indice di rifrazione
1.4120
Sensibilità
Moisture Sensitive
Solubilità
Miscible with acetonitrile.

Applicazioni

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.

Note

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

Letteratura

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).

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.

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (UE): H225-H330-H302-H314-H318

Highly flammable liquid and vapour. Fatal if inhaled. Harmful if swallowed. Causes severe skin burns and eye damage. Causes serious eye damage.

Dichiarazioni precauzionali: P210-P260-P284-P303+P361+P353-P304+P340-P305+P351+P338-P320-P330-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Do not breathe dust/fume/gas/mist/vapours/spray. Wear respiratory protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Specific treatment is urgent (see label). Rinse mouth. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Altri riferimenti

Beilstein
385668
Classe di rischio
6.1
Gruppo di imballaggio
I
Codice tariffe armonizzato
2915.90
TSCA
Yes

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