4300-97-4

Basic information

• Product Name: 3-Chloropivaloyl chloride
• Synonyms: CHLOROPIVALOYL CHLORIDE;CPC;3-CHLOROPIVALIC CHLORIDE;3-CHLOROPIVALOYL CHLORIDE;3-chloro-2,2-dimethylpropanoyl chloride;3-CHLORO-2,2-DIMETHYLPROPIONYL CHLORIDE;3-chloro-2,2-dimethylpropaneyl chloride;3-Chloro-2,2-dimethylpropionyl chloride, tech
• CAS NO: 4300-97-4
• Molecular Formula: C₅H₈Cl₂O
• Molecular Weight: 155.02
• EINECS: 224-311-8
• Product Categories: Acid Halides;Building Blocks;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 4300-97-4.mol

Chemical Properties

• Boiling Point: 85-86 °C60 mm Hg(lit.)
• Flash Point: 145 °F
• Appearance: clear colorless to light yellow-brown liquid
• Density: 1.199 g/mL at 25 °C(lit.)
• Vapor Pressure: 2.44mmHg at 25°C
• Refractive Index: n20/D 1.453(lit.)
• Water Solubility: reacts
• CAS DataBase Reference: 3-Chloropivaloyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Chloropivaloyl chloride(4300-97-4)
• EPA Substance Registry System: 3-Chloropivaloyl chloride(4300-97-4)

Safety Data

• Hazard Codes: C,Xi,T+
• Statements: 34-36/37-23-22-26
• Safety Statements: 26-36/37/39-45-28
• RIDADR: UN 3390 6.1/PG 1
• WGK Germany: 3
• F: 19
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 4300-97-4(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
3-Chloropivaloyl chloride is used as a key intermediate in the synthesis of various compounds, particularly those with antimicrobial and antioxidant activities. Its chemical properties make it a valuable building block for creating new molecules with potential applications in different industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3-Chloropivaloyl chloride is used as a reagent for the synthesis of drugs with antimicrobial properties. Its ability to form compounds with potent antimicrobial activity makes it a valuable asset in the development of new antibiotics and antifungal agents.
Used in Cosmetics Industry:
3-Chloropivaloyl chloride is also utilized in the cosmetics industry for the synthesis of compounds with antioxidant properties. These antioxidants can be incorporated into skincare products to protect the skin from oxidative stress and environmental damage, promoting overall skin health and longevity.
Used in Agricultural Industry:
In the agricultural industry, 3-Chloropivaloyl chloride is used as a starting material for the development of compounds with antimicrobial and antifungal properties. These compounds can be applied to crops to protect them from diseases and pests, ensuring a higher yield and better quality produce.
Overall, 3-Chloropivaloyl chloride is a versatile compound with a wide range of applications across various industries, primarily due to its ability to synthesize compounds with antimicrobial and antioxidant activities. Its use in chemical synthesis, pharmaceuticals, cosmetics, and agriculture highlights its importance in the development of new products and technologies.

Air & Water Reactions

Highly flammable. Slightly soluble in water and less dense than water. Hence floats on water. Reacts with water to form hydrochloric acid (hydrogen chloride).

Reactivity Profile

3-Chloropivaloyl chloride is incompatible with strong oxidizing agents, alcohols, bases, including amines. 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

TOXIC; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death. Contact with molten substance may cause severe burns to skin and eyes. Reaction with water or moist air will release toxic, corrosive or flammable gases. Reaction with water may generate much heat that will increase the concentration of fumes in the air. Fire will produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.

Fire Hazard

Combustible material: may burn but does not ignite readily. Substance will react with water (some violently) releasing flammable, toxic or corrosive gases and runoff. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapors may travel to source of ignition and flash back. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated or if contaminated with water.

InChI:InChI=1/C5H8Cl2O/c1-5(2,3-6)4(7)8/h3H2,1-2H3

Upstream product

• 3282-30-2 pivaloyl chloride 
• 7791-25-5 sulfuryl dichloride 
• 78-67-1 2,2'-azobis(isobutyronitrile) 
• 71-43-2 benzene 
• 56-23-5 tetrachloromethane 
• 94-36-0 dibenzoyl peroxide 
• 594-37-6 1,2-dichloro-2-methylpropane 
• 75-98-9 Trimethylacetic acid 
• 4835-90-9 3-Hydroxy-2,2-dimethylpropanoic acid 
• 13511-38-1 3-chloropivalic acid 

Downstream Products

• 2654-58-2 4,4-dimethyl-1-phenylpyrazolidin-3-one 
• 25218-69-3 3-Chloro-2,2-dimethyl-N-(3-propionylamino-phenyl)-propionamide 
• 68428-95-5 3-Chloro-2,2-dimethyl-propionic acid 2-(2,4-dimethyl-phenyl)-5,5-dimethyl-3-oxo-cyclohex-1-enyl ester 
• 59517-53-2 2-Methyl-pentanoic acid [3-(3-chloro-2,2-dimethyl-propionylamino)-phenyl]-amide 
• 25218-70-6 3'-(2,2-dimethyl-3-chloropropionamido)2,2-dimethylvaleranilide 
• 59517-35-0 3-Chloro-N-[3-(2,2-dimethyl-propionylamino)-phenyl]-2,2-dimethyl-propionamide 
• 25218-68-2 3'-(2,2-dimethyl-3-chloropropionamido)2,2-dimethyl-3-chloropropionanilide 
• 82820-74-4 N-phenyl β-chloro-α,α-dimethylpropionamide 
• 104224-04-6 5,6-dihydro-5,5-dimethyl-2-phenyl-1,3-thiazin-4-one 
• 86726-94-5 3,5,5-Trimethyl-1-phenyl-2-thioxo-tetrahydro-pyrimidin-4-one 
• 73434-12-5 N-Methyl-3-chloropivalamide 
• 107288-85-7 2-(2-chloro-1,1-dimethylethyl)-4-phenyl-quinazoline 
• 84669-85-2 3,3-Dimethyl-2-oxo-azetidine-1-carbothioic acid phenylamide 
• 84669-86-3 2,2-Dimethyl-3-(3-phenyl-thioureido)-propionic acid 

Relevant articles and documents

Method for preparing 3-chloro-2,2-dimethylpropionyl chloride

The invention discloses a method for preparing 3-chloro-2,2-dimethylpropionyl chloride. The method is characterized in that 3-chloro-2,2-dimethylpropioric acid and phosgene undergo an acylating chlorination reaction in the presence of a catalyst to obtain the 3-chloro-2,2-dimethylpropionyl chloride. The method has the advantages of simple process, easiness in operation, mild and easily-controlledconditions, low energy consumption, low cost, high yield, high purity, clean reaction, no pollution, realization of comprehensive utilization of a byproduct hydrochloric acid, and suitableness for industrial production.

Palladium-catalyzed C(carbonyl)-C bond cleavage of amides: a facile access to phenylcarbamate derivatives with alcohols

A sulfur-containing auxiliary enabled palladium-catalyzed C(carbonyl)-C bond activation of amides was reported to form phenylcarbamate derivatives with alcohols. Both alkyl and benzyl alcohols could be employed well with yields up to 85%. Derivations from phenylcarbamates to ureas and thiocarbamates illustrated the potential applications of this sequential C-C cleavage/C-O coupling reaction.

Cu-Catalyzed Alkynylation of Unactivated C(sp3)-X Bonds with Terminal Alkynes through Directing Strategy

In this letter, we report an efficient and concise protocol for Cu-catalyzed cross-coupling of unactivated alkyl halides/peusudohalides with terminal alkynes to afford internal alkynes with the assistance of various amides as directing groups. Different alkyl halides/pseudohalides exhibited excellent reactivities, and the inactivated alkyl chlorides and sulfonates showed better reactivity than bromides/iodides. This is the first successful example to apply alkyl chlorides and sulfonates directly in cross-coupling with terminal alkynes in the absence of any additives. A Cu catalyst was found to be more effective than other transition metal catalysts. This reaction also exhibited a broad substrate scope with respect to terminal alkynes.

Reductive synthesis of aminal radicals for carbon-carbon bond formation

Aminal radicals were generated by reduction of the corresponding amidine or amidinium ion. The intermediate radicals participate in C-C bond-forming reactions to produce fully substituted aminal stereocenters. No toxic additives or reagents are required. More than 30 substrate combinations are reported, and chemical yields are as high as 99%.

Copper-catalyzed site-selective intramolecular amidation of unactivated C(sp3)-H bonds

The intramolecular dehydrogenative amidation of aliphatic amides, directed by a bidentate ligand, was developed using a copper-catalyzed sp3 C-H bond functionalization process. The reaction favors predominantly the C-H bonds of β-methyl groups over the unactivated methylene C-H bonds. Moreover, a preference for activating sp3 C-H bonds of β-methyl groups, via a five-membered ring intermediate, over the aromatic sp2 C-H bonds was also observed in the cyclometalation step. Additionally, sp3 C-H bonds of unactivated secondary sp3 C-H bonds could be functionalized by favoring the ring carbon atoms over the linear carbon atoms. Getting ahead on tams: The intramolecular dehydrogenative amidation of aliphatic amides, directed by a bidentate ligand, was developed using a copper-catalyzed sp 3 C-H bond functionalization process to deliver β-lactams. The reaction favors the C-H bonds of β-methyl groups over the unactivated methylene C-H bonds, as well as aromatic C(sp2)-H bonds and unactivated secondary C(sp3)-H bonds of rings.

Inhibitors of CYP 17

The present invention provides compounds of Formula (I) and (II), or a pharmaceutically acceptable salts thereof, where R53, R54, p, q, and n are as defined herein. The compounds of the present invention have been found to be useful as 17α-hydroxylase/C17,20-lyase inhibitors.

1, 3-DISUBSTITUTED IMIDAZOLIDIN-2-ONE DERIVATIVES AS INHIBITORS OF CYP 17

The present invention provides compounds of Formula (I) and (II), or a pharmaceutically acceptable salts thereof, where R53, R54, p, q and n are as defined herein. The compounds of the present invention have been found to be useful as 17α-hydroxylase/C17,20-lyase inhibitors.

Converting gem-dimethyl groups into cyclopropanes via Pd-catalyzed sequential C-H activation and radical cyclization

(Diagram presented) A novel route to the synthesis of cyclopropane derivatives is described. 1,1-Dimethyls in 2-(1,1-dimethylalkyl) dimethyloxazolines are first converted into 1,3-diiodide derivatives via Pd-catalyzed sequential C-H activation and then radically cyclized to provide 2-(1-alkylcylclopropyl)-dimethyloxazolines. The use of EtOAc as a solvent is crucial for the diiodination of the functionalized substrates.

CATALYTICS ASYMMETRIC ACTIVATION OF UNACTIVATED C-H BONDS, AND COMPOUNDS RELATED THERETO

One aspect of the present invention is directed in part to catalytic and stereoselective functionalization of unactivated C-H bonds of simple organic substrates. The compounds and methods provided herein allow one to control the stereochemistry in a C-H activation step, activate substrates containing α-hydrogens next to the directing group, and remove a directing group under mild conditions. One aspect of the present invention relates to a transition-metal-catalyzed method for selective and asymmetric oxidation of carbons located in a β- or γ-position relative to an auxiliary. Another aspect of the invention relates to the enantiomerically-enriched substrates and the enantiomerically-enriched products formed via said method. In certain embodiments, oxazoline and oxazinone directing groups are used. In addition, the Boc protecting group has been identified as a directing group which does not necessitate removal.

Process for preparing acid halides

Acid halides of the formula (R1, R2, R3)C--CO--Hal are obtained by reacting alkyl halides of the formula (R1, R2, R3)C--Hal with carbon monoxide under a pressure of 5 to 1,000 bar and at a temperature of -20° C. to +100° C. in the presence of 0.001 to 0.3 mol of AlCl3 and/or FeCl3, if appropriate in the presence of a further Bronsted or Lewis acid, per mol of the alkyl halide. The process is carried out, if desired in the presence of a solvent which is customary for Friedel-Crafts or Friedel-Crafts-related reactions and, if appropriate in the presence of a hydrogen halide. The acid chloride can be isolated from the reaction mixture or further reacted.