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
• Article Data: 17

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

Chemical Properties

clear colorless to light yellow-brown liquid

Uses

3-Chloropivaloyl Chloride is useful in the synthesis of compounds with antimicrobial and antioxidant activities.

General Description

A colorless liquid. Very toxic by ingestion, inhalation and skin absorption. Flash point near 70°F. Corrosive. Contact may severely irritate skin, eyes, and mucous membranes. Used to make other chemicals.

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

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

Downstream Products

• 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 
• 93623-84-8 3,3-Dimethyl-1-{[1-phenyl-meth-(Z)-ylidene]-amino}-azetidin-2-one 
• 71663-75-7 N-(benzyloxy)-3,3-dimethyl-2-azetidinone 
• 79289-24-0 benzophenone β-chloro-α,α-dimethylpropionylhydrazone 
• 79289-47-7 1-<(diphenylmethylene)amino>-3,3-dimethylazetidin-2-one 
• 77868-89-4 (R)-(3-Bromo-3-methyl-2-oxo-azetidin-1-yl)-phenyl-acetic acid 
• 84669-88-5 3,3-Dimethyl-2-oxo-azetidine-1-carbothioic acid cyclohexylamide 
• 84669-89-6 3-(3-Cyclohexyl-thioureido)-2,2-dimethyl-propionic acid 
• 86727-02-8 3-Benzyl-1,5,5-trimethyl-2-thioxo-tetrahydro-pyrimidin-4-one 

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.

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.

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.