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A15051 Trimethylacetyl chloride, 98+%

CAS Number
3282-30-2
Synonyms
Pivaloyl chloride

Stock No. Size Price ($) Quantity Availability
A15051-AE 100ml 15.70
A15051-AP 500ml 53.70
A15051-0F 2500ml 203.00
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Trimethylacetyl chloride, 98+%

MDL
MFCD00000709
EINECS
221-921-6

Chemical Properties

Formula
(CH3)3CCOCl
Formula Weight
120.58
Melting point
-57°
Boiling Point
105-106°
Flash Point
8°(46°F)
Density
0.985
Refractive Index
1.4120
Storage & Sensitivity
Moisture Sensitive. Ambient temperatures.
Solubility
Miscible with acetonitrile.

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.

Notes

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

Literature 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 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.

GHS Hazard and Precautionary Statements

Hazard Statements: H225-H290-H302-H314-H330

Highly flammable liquid and vapour. May be corrosive to metals. Harmful if swallowed. Causes severe skin burns and eye damage. Fatal if inhaled.

Precautionary Statements: P210-P233-P234-P235-P240-P241-P242-P243-P260-P264b-P270-P271-P280-P284-P303+P361+P353-P304+P340-P305+P351+P338-P310-P330-P331-P363-P370+P378q-P390-P501c

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep container tightly closed. Keep only in original container. Keep cool. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Use only non-sparking tools. Take precautionary measures against static discharge. Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. 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. Immediately call a POISON CENTER or doctor/physician. Rinse mouth. Do NOT induce vomiting. Wash contaminated clothing before reuse. In case of fire: Use CO2, dry chemical, or foam Absorb spillage to prevent material damage. Dispose of contents/ container to an approved waste disposal plant

Other References

Beilstein
385668
Hazard Class
6.1
Packing Group
I
Harmonized Tariff Code
2915.90
TSCA
Yes

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