3282-30-2 Usage
Description
Pivaloyl chloride, also known as trimethylacetyl chloride, is a colorless fuming liquid with a pungent odor. It has a boiling point of 105-106°F (40.5-41.1°C) and a density of 0.979 g/cm3. Pivaloyl chloride is very toxic by inhalation, ingestion, or skin absorption, and its fumes can irritate the eyes and mucous membranes. It is also corrosive to most metals and tissue.
Uses
1. Pharmaceutical Industry:
Pivaloyl chloride is used as a precursor in the preparation of various pharmaceutical compounds, such as tert-butyl peroxypivalate, guttiferon A derivatives (potential treatment for malaria), synthetic acidamide medicament, and phenol ester medicament. It is also utilized in the synthesis of active pharmaceutical ingredients like aminobenzylpenicilin, cephalexin, cefazolin, dipivefrin, and dipivalyl epinephrine.
2. Chemical Synthesis:
Pivaloyl chloride serves as a widely used N-acylating agent for amines, Schiff bases, and pyrrolidinones. It is also an O-acylating agent for alcohols, lactones, and saccharides, making it a versatile compound in chemical synthesis.
3. Polymerization:
In the field of polymer science, Pivaloyl chloride is used in heavy polymerization processes, contributing to the development of various polymer materials.
4. Industrial Applications:
Due to its reactivity and versatility, Pivaloyl chloride finds applications in various industrial processes, particularly in the synthesis of intermediates and final products for different industries.
Synthesis Reference(s)
Tetrahedron Letters, 29, p. 4569, 1988 DOI: 10.1016/S0040-4039(00)80549-3
Air & Water Reactions
Highly flammable. Fumes in air. Reacts vigorously and exothermically with water to form trimethylacetic acid and corrosive hydrochloric acid; both acids corrode metals and tissue [AAR 1991].
Reactivity Profile
Pivaloyl chloride is acidic. Incompatible with bases (including amines), strong oxidizing agents, and alcohols. May react vigorously or explosively if mixed with diisopropyl ether or other ethers in the presence of trace amounts of metal salts [J. Haz. Mat., 1981, 4, 291].
Health Hazard
May cause toxic effects if inhaled or ingested/swallowed. Contact with substance may cause severe burns to skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.
Fire Hazard
Flammable/combustible material. May be ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.
Flammability and Explosibility
Flammable
Safety Profile
A corrosive irritant to
skin, eyes, and mucous membranes. The
liquid is flammable when exposed to heat,
flame, or oxiduers. When heated to
decomposition it emits toxic fumes of Cl-.
Purification Methods
First check the IR to see if OH bands are present. If absent, or present in small amounts, then redistil it under a moderate vacuum. If present in large amounts then treat it with oxalyl chloride or thionyl chloride and reflux for 2-3hours, evaporate and distil the residue. Strongly LACHRYMATORY -work in a fumecupboard. Store it in sealed ampoules under N2. [Traynham & Battiste J Org Chem 22 1551 1957, Grignard reactions: Whitmore et al. J Am Chem Soc 63 647 1941, Beilstein 2 IV 912.]
Check Digit Verification of cas no
The CAS Registry Mumber 3282-30-2 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,2,8 and 2 respectively; the second part has 2 digits, 3 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 3282-30:
(6*3)+(5*2)+(4*8)+(3*2)+(2*3)+(1*0)=72
72 % 10 = 2
So 3282-30-2 is a valid CAS Registry Number.
InChI:InChI=1/C5H9ClO/c1-5(2,3)4(6)7/h1-3H3
3282-30-2Relevant articles and documents
Nickel-catalyzed direct C-H bond sulfenylation of acylhydrazines
Li, Jun-Ming,Yu, Yang,Weng, Jiang,Lu, Gui
, p. 6047 - 6056 (2018)
A Ni-catalyzed direct C-H bond sulfenylation of acylhydrazines was developed. The reaction used N-(pyridinyl)hydrazine as the bidentate-directing group, which can be smoothly removed through reductive N-N cleavage. This system can bear various important functional groups, providing an efficient route for the preparation of diverse diaryl sulfides.
REACTION OF SULFURYL CHLORIDE WITH P-TRIMETHYLSILYL-C-TERT-BUTYL-C-TRIMETHYLSILYLOXYMETHYLENEPHOSPHINE
Ionkin, A. S.,Nikolaeva, N. V.,Arbuzov, B. A.
, (1990)
-
Rhodium(III)-catalyzed chemodivergent annulations between phenyloxazoles and diazos via C–H activation
Zhang, Xueguo,Wang, Peigen,Zhu, Liangwei,Chen, Baohua
supporting information, p. 695 - 699 (2020/06/28)
Acid-controlled, chemodivergent and redox-neutral annulations for the synthesis of isocoumarins and isoquinolinones have been realized via Rh(III)-catalyzed C[sbnd]H activation. Diazo compounds act as a carbene precursor, and coupling occurs in one-pot process, where adipic acid and trimethylacetic acid promote chemodivergent cyclizations.
Benzimidazole tethered thioureas as a new entry to elastase inhibition and free radical scavenging: Synthesis, molecular docking, and enzyme inhibitory kinetics
Abbas, Qamar,Ashraf, Saba,Channar, Pervaiz Ali,Hassan, Abbas,Hassan, Mubashar,Rafique, Hummera,Raza, Hussain,Rind, Mahboob Ali,Saeed, Aamer,Seo, Sung-Yum,Ujan, Rabail,Ul-Hamid, Anwar
, (2021/07/02)
The porcine pancreatic elastase inhibition and free-radical scavenging play a crucial role in age progression. All the series of 10 newly synthesized benzimidazole thioureas (4a-j) were assessed for elastase inhibition and radical scavenging activity to identify the suitable anti-aging ingredient for cosmetics products. The compounds 4e, 4f, 4g, and 4h showed inhibition better than the standard, while compound 4f showed the most significant elastase inhibition with the IC50 value of 1.318 ± 0.025 μM compared with oleanic acid IC50 13.451 ± 0.014 used ±1.989 and 41.563 ± 0.824, respectively, as standard. Molecular docking studies were performed and the compound 4f showed binding energy of 7.2 kcal/mol. Kinetics studies revealed inhibition of the pancreatic elastase in a competitive manner. The relative binding energy and structure activity relationship (SAR) identified compound 4f as an effective inhibitor of porcine pancreatic elastase. Compounds 4e and 4i showed remarkable free-radical scavenging activity with SC50 values of 26.421.
Palladium-catalyzed cascade decarboxylative amination/6- endo-dig benzannulation of o-alkynylarylketones with n-hydroxyamides to access diverse 1-naphthylamine derivatives
Zuo, Youpeng,He, Xinwei,Tang, Qiang,Hu, Wangcheng,Zhou, Tongtong,Shang, Yongjia
supporting information, p. 3890 - 3894 (2020/05/18)
An efficient and practical one-pot strategy to produce highly substituted 1-naphthylamines via sequential palladium-catalyzed decarboxylative amination/intramolecular 6-endo-dig benzannulation reactions has been described. In this reaction, a broad range of electron-rich, electron-neutral, and electron-deficient o-alkynylarylketones react well with N-hydroxyl aryl/alkylamides to give a diversity of 1-naphthylamines in good to excellent yields under mild reaction conditions. The gram-scale synthesis, with benefits such as undiminished product yield and easy transformation, illustrated the practicality of this method.