99-91-2

Basic information

• Product Name: 4'-Chloroacetophenone
• Synonyms: 1-(4-chlorophenyl)-ethanon;1-(4-chlorophenyl)ethanone[qr];4’-chloro-acetophenon;4-acetylchlorobenzene;4-chloroacetophenone[qr];4-chlorophenylmethylketone;Acetophenone, 4'-chloro-;acetophenone,4-chloro-[qr]
• CAS NO: 99-91-2
• Molecular Formula: C₈H₇ClO
• Molecular Weight: 154.59
• EINECS: 202-800-7
• Product Categories: Chlorobenzene Series;Acetophenone Series;FINE Chemical & INTERMEDIATES;Aromatic Acetophenones & Derivatives (substituted);Organics;C7 to C8;Carbonyl Compounds;Ketones
• Mol File: 99-91-2.mol

Chemical Properties

• Melting Point: 74-76 °C(lit.)
• Boiling Point: 232 °C(lit.)
• Flash Point: 194 °F
• Appearance: Clear colorless to yellow/Liquid After Melting
• Density: 1.192 g/mL at 25 °C(lit.)
• Vapor Pressure: 8 mm Hg ( 90 °C)
• Refractive Index: n20/D 1.554(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: 111mg/l (slow decomposition)
• Water Solubility: 111 mg/L (25 ºC)
• Merck: 14,2116
• BRN: 386014
• CAS DataBase Reference: 4'-Chloroacetophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-Chloroacetophenone(99-91-2)
• EPA Substance Registry System: 4'-Chloroacetophenone(99-91-2)

Safety Data

• Hazard Codes: T+,Xn
• Statements: 22-26-37/38-41-36/37/38-36/37
• Safety Statements: 26-28-36/37/39-45-28A-36
• RIDADR: UN 3416 6.1/PG 2
• WGK Germany: 3
• RTECS: KM5600000
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 99-91-2(Hazardous Substances Data)

Usage

Uses

Used in Law Enforcement:
4'-Chloroacetophenone is used as a tear gas for riot control, serving as an effective means to manage and disperse crowds during civil unrest or protests. Its ability to cause intense irritation to the eyes, respiratory tract, and skin makes it a potent agent for controlling large groups of people.
Used in Personal Defense:
In addition to its role in riot control, 4'-Chloroacetophenone is also utilized as a component of chemical mace or pepper spray. It is employed for self-defense purposes against small groups or individuals, providing a non-lethal means of protection. When used in this context, 4'-Chloroacetophenone can incapacitate an aggressor temporarily, allowing the user to escape or seek assistance.

Synthesis Reference(s)

The Journal of Organic Chemistry, 44, p. 2568, 1979 DOI: 10.1021/jo01328a051Tetrahedron Letters, 42, p. 265, 2001 DOI: 10.1016/S0040-4039(00)01935-3Synthetic Communications, 25, p. 2261, 1995 DOI: 10.1080/00397919508011781

Safety Profile

Poison by intraperitoneal route. Moderately toxic by ingestion. A powerful irritant and lachrymator. Human systemic effects by inhalation: lachrymation and unspecified effects on the eye and sense of smell. Combustible when exposed to heat or flame. To fight fire, use water, foam, alcohol foam, dry chemical. When heated to decomposition or on contact with water or steam it emits toxic fumes of Cl-

Upstream product

• 1073-67-2 4-vinylbenzyl chloride 
• 107-29-9 Acetaldehyde oxime 
• 17333-85-6 4-chlorophenyldiazonium salt 
• 1615-02-7 p-chlorocinnamic acid 
• 3710-84-7 N-ethyl-N-hydroxy-ethanamine 
• 127-19-5 N,N-dimethyl acetamide 
• 14774-78-8 4-chlorophenyl lithium 
• 3391-10-4 1-(p-chlorophenyl)ethyl alcohol 
• 17589-68-3 3-(4-chlorophenyl)-3-oxopropanoic acid 
• 108-24-7 acetic anhydride 
• 108-90-7 chlorobenzene 
• 99187-99-2 2-(4-chlorophenyl)butane-2,3-diol 
• 546-67-8 lead(IV) tetraacetate 
• 64-19-7 acetic acid 

Downstream Products

• 42945-85-7 2-(4-chlorophenyl)-1-(morpholin-4-yl)-ethanethione 
• 7469-98-9 1,4-bis-[3-(4-chloro-phenyl)-3-oxo-propyl]-piperazine; dihydrochloride 
• 28561-06-0 1-(4-chloro-phenyl)-1-pyridin-4-yl-ethanol 
• 197512-40-6 1-(4-chlorophenyl)-1-(pyridin-2-yl)ethan-1-ol 
• 105688-33-3 1-[2-(4-chloro-phenyl)-2-oxo-ethyl]-pyridinium iodide 
• 5337-52-0 (E)-1-(4-chlorophenyl)-3-(pyridin-2-yl)prop-2-en-1-one 
• 14385-65-0 (2E)-1-(4-chlorophenyl)-3-(2-furyl)prop-2-en-1-one 
• 4397-43-7 1-(4-chloro-phenyl)-3-quinolin-2-yl-propenone 
• 351332-56-4 2-(4-chlorophenyl)-6-methylquinoline-4-carboxylic acid 
• 69538-64-3 (E)-3-(benzo[d][1,3]dioxol-5-yl)-1-(4-chlorophenyl)prop-2-en-1-one 
• 124930-93-4 8-chloro-2-(4-chlorophenyl)cinchoninic acid 
• 5466-31-9 2-(4-chlorophenyl)quinoline-4-carboxylic acid 
• 23241-13-6 3-(2-(4-chlorophenyl)-2-oxoethyl)-3-hydroxyindolin-2-one 
• 126088-20-8 6-chloro-2-(4-chlorophenyl)quinoline-4-carboxylic acid 

Relevant articles and documents

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Selective Activation of Unstrained C(O)-C Bond in Ketone Suzuki-Miyaura Coupling Reaction Enabled by Hydride-Transfer Strategy

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Stepwise benzylic oxygenation via uranyl-photocatalysis

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METHOD FOR OXIDATIVE CLEAVAGE OF COMPOUNDS WITH UNSATURATED DOUBLE BOND

A method for oxidative cleavage of a compound with an unsaturated double bond is provided. The method comprises the following step: (A) providing a compound (I) with an unsaturated double bond, a reagent with trifluoromethyl, and a catalyst; wherein the catalyst is represented by the following formula (II): M(O)mL1yL2z (II); wherein, M, L1, L2, m, y, z, R1, R2 and R3 are defined in the specification; and (B) mixing the compound with an unsaturated double bond and the reagent with a trifluoromethyl to perform an oxidation of the compound with the unsaturated double bond by using the catalyst at air or an oxygen condition to get a compound presented as formula (III):

Surfactant-Assisted Ozonolysis of Alkenes in Water: Mitigation of Frothing Using Coolade as a Low-Foaming Surfactant

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Linkage engineering mediated carriers transfer and surface reaction over carbon nitride for enhanced photocatalytic activity

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Method for oxidative cracking of compound containing unsaturated double bonds

The invention relates to a method for oxidative cracking of a compound containing unsaturated double bonds. The method comprises the following steps: (A) providing a compound (I) containing unsaturated double bonds, a trifluoromethyl-containing reagent and a catalyst, wherein the catalyst is shown as a formula (II): M(O)mL1yL2z (II), M, L1, L2, m, y, z, R1, R2 and R3 being defined in the specification; and (B) mixing the compound containing the unsaturated double bonds and the trifluoromethyl-containing reagent, and performing an oxidative cracking reaction on the compound containing the unsaturated double bonds in the presence of air or oxygen by using the catalyst to obtain a compound represented by formula (III),.

METHOD FOR OXIDATIVE CLEAVAGE OF COMPOUNDS WITH UNSATURATED DOUBLE BOND

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Electrochemical reactivity of S-phenacyl-O-ethyl-xanthates in hydroalcoholic (MeOH/H2O 4:1) and anhydrous acetonitrile media

The electrochemical behavior of a series of S-phenacyl-O-ethyl-xanthates (O-ethyl-dithiocarbonate acetophenone derivatives) in hydroalcoholic (MeOH/H2O 4:1) and anhydrous media (ACN/TBAPF6) using carbon electrodes was studied. Cyclic voltammetry showed in hydroalcoholic media only two cathodic waves, whereas in ACN one anodic and two cathodic waves were present. The first cathodic wave corresponded to the reduction of the phenylketone group, whereas the first anodic was attributed to the xanthate unit. Macroelectrolysis on graphite and vitreous carbon at anodic and cathodic potentials, let us to explore the synthetic potential of this electrochemical reactions. With some compounds in hydroalcoholic media and using carbon electrodes, polymeric material was deposited on the electrode impeding the reaction; this deposit was characterized by AFM and SEM-EDS. The electroreduction on Ti electrode overcome this problem and gave the corresponding acetophenones (>95%). On the other hand, in ACN, small quantities of the dimeric 1,4-dicarbonyl compounds X-PhCOCH2CH2COPh-X (7–15%), as well as the corresponding acetophenones (ca. 50%) were isolated. Oxidation macroelectrolysis showed a very complicated transformation without synthetic value. The reaction mechanism for the reduction and the homolytic dissociation into the phenacyl radical was supported by DFT calculations.