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)
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AKT INHIBITOR
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Paragraph 0122-0123; 0128; 096-0197, (2021/12/18)
The present invention discloses an AKT inhibitor, and specifically relates to a compound represented by formula I or a pharmaceutically acceptable salt thereof. The present invention further provides a preparation method thereof, and the use thereof in prevention and/or treatment of a disease mediated by AKT protein kinase.
Synthesis, computational studies and enzyme inhibitory kinetics of benzothiazole-linked thioureas as mushroom tyrosinase inhibitors
Ujan, Rabail,Saeed, Aamer,Ashraf, Saba,Channar, Pervaiz Ali,Abbas, Qamar,Rind, Mahboob Ali,Hassan, Mubashir,Raza, Hussain,Seo, Sung-Yum,El-Seedi, Hesham R.
, p. 7035 - 7043 (2020/08/12)
Herein, we report synthesis of a set of benzothiazole-thiourea hybrids with aromatic and aliphatic side chains (BT1 to BT9) using an elegant synthetic strategy. The newly synthesized benzothiazole-thiourea conjugates were subjected to In-vitro tyrosinase inhibition and free radical scavenging activity. Majority of the compounds indicated inhibition considerably improved than the standard; compound (Kojic acid with IC50 = 16.8320 ± 1.1600 μM) BT2 with IC50 = 1.3431 ± 0.0254 μM was found to be the best inhibitor. A non-competitive mode of inhibition of BT2 was disclosed with Ki value of 2.8 μM. In order to study enzyme-inhibitor interactions SAR analysis molecular docking was carried out. The amino groups of thiourea were involved in hydrogen bonding with Glu322 showing the bond length of 1.74 and 2.70 ?, respectively. Moreover, the coupling of π-π was displayed between benzothiazole and benzene rings of His244 and His263, respectively. The outcome of this study might help to develop new inhibitors of melanogenesis, important for cosmetic and food products. Communicated by Ramaswamy H. Sarma.
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.