82-44-0

Basic information

• Product Name: 1-Chloro anthraquinone
• Synonyms: 1-CHLOROANTHRACENE-9,10-DIONE;1-CHLOROANTHRAQUINONE;1-CHLORO AQ;1-chloro-9,10-anthracenedione;TIMTEC-BB SBB000825;.alpha.-Chloroanthraquinone;10-Anthracenedione,1-chloro-9;1-Chloranthrachinon
• CAS NO: 82-44-0
• Molecular Formula: C₁₄H₇ClO₂
• Molecular Weight: 242.66
• EINECS: 201-421-4
• Product Categories: Intermediates of Dyes and Pigments;Anthraquinones;Chloroanthraquine, etc.;C13 to C14;Carbonyl Compounds;Ketones;API Intermediate
• Mol File: 82-44-0.mol
• Article Data: 10

Chemical Properties

• Melting Point: 159-160 °C(lit.)
• Boiling Point: 345.65°C (rough estimate)
• Flash Point: 179.7 °C
• Appearance: Light yellow to yellow/Powder or Chunks
• Density: 1.2377 (rough estimate)
• Vapor Pressure: 1.87E-07mmHg at 25°C
• Refractive Index: 1.5380 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: Soluble in hot toluene. (almost transparency)
• BRN: 1912752
• CAS DataBase Reference: 1-Chloro anthraquinone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Chloro anthraquinone(82-44-0)
• EPA Substance Registry System: 1-Chloro anthraquinone(82-44-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-24/25
• WGK Germany: 3
• RTECS: CB6150000
• TSCA: Yes
• Hazardous Substances Data: 82-44-0(Hazardous Substances Data)

Usage

Uses

Used in Dye Manufacturing Industry:
1-Chloro anthraquinone is used as an intermediate for manufacturing vat dyes, specifically CI Vat Brown 1. Its chemical structure allows for the formation of color-producing compounds that are widely used in the textile industry for dyeing fabrics.
Used in Pharmaceutical Industry:
1-Chloro anthraquinone is used to characterize anthraquinone intercalators as carrier molecules for second-generation platinum anticancer drugs. Its unique properties enable it to interact with DNA and deliver the anticancer agents to cancer cells, improving the effectiveness of the treatment and reducing side effects.

Safety Profile

Poison by intravenous route. An eye irritant. When heated to decomposition it emits very toxic fumes of Cland NOx.

InChI:InChI=1/C14H7ClO2/c15-11-7-3-6-10-12(11)14(17)9-5-2-1-4-8(9)13(10)16/h1-7H

Upstream product

• 4888-02-2 4-chloroanthrone 
• 25186-79-2 1-chloro-9,10-dioxo 9,10-dihydro-3-anthracenecarboxylic acid 
• 82-34-8 1-nitroanthraquinone 
• 7782-50-5 chlorine 
• 87-61-6 1,2,3-trichlorobenzene 
• 7647-01-0 hydrogenchloride 
• 82-49-5 1-anthraquinonesulfonic acid 
• 4887-98-3 1-chloro-9-anthrone 
• 117-21-5 3-chlorophthalic anhydride 
• 1234379-63-5 C₁₄H₁₁ClN₂ 
• 82-46-2 1,5-Dichloroanthraquinone 
• 103244-78-6 1,5-dichloroanthrahydroquinone 
• 82-45-1 1-amino-9,10-anthracenedione 
• 4025-69-8 anthraquinone-1-sulfonyl chloride 

Downstream Products

• 6545-54-6 2-bromo-1,1'-imino-di-anthraquinone 
• 117-03-3 1,5-bis-(9,10-dioxo-9,10-dihydro-[1]anthrylamino)-anthraquinone 
• 116-76-7 1,4-bis-(1-anthraquinonylamino)anthraquinone 
• 396732-60-8 2-(9,10-dioxo-9,10-dihydro-[1]anthrylmercapto)-benzoic acid 
• 75083-42-0 4-benzoylamino-1,1'-imino-di-anthraquinone 
• 81-94-7 1-[(7-oxo-7H-benz[de]anthracene-3-yl)amino]anthraquinone 
• 4478-06-2 2,6-bis-(9,10-dioxo-9,10-dihydro-[1]anthrylamino)-anthraquinone 
• 55868-88-7 1-[methyl-(toluene-4-sulfonyl)-amino]-anthraquinone 
• 13354-35-3 1-phenylsulfanyl-anthraquinone 
• 122357-52-2 1-(3-methoxy-phenoxy)-anthraquinone 
• 75507-60-7 1-(toluene-4-sulfonyl)-anthraquinone 
• 111063-69-5 anthra[9,1-ef]benzo[b][1,4]thiazepin-9-one 
• 43217-27-2 1-chloro-9,10-diphenylanthracene 
• 81-64-1 1,4-dihydroxy-9,10-anthracenedione 

Relevant articles and documents

Efficient indium-mediated dehalogenation of aromatics in ionic liquid media

An efficient indium-mediated dehalogenation reaction of haloaromatics and haloheteroaromatics in ionic liquids has been studied. This method is simple and effective in the presence of [bmim]Br. Furthermore, this methodology is environmentally friendly compared with conventional ones.

Carbon-carbon cleavage of aryl diamines and quinone formation using sodium periodate: a novel application

A first novel synthetic utility of sodium periodate for aryl diamine carbon-carbon cleavage is described. Aryl 1,2-diamine compounds were successfully converted into corresponding nitriles, while the developed method is also useful for the preparation of quinones from corresponding aryl 1,4-diamine compounds. The advantages of this protocol are shorter reaction time and mild reaction conditions to obtain moderate to good yields.

A novel application of (Diacetoxyiodo)benzene for carbon-carbon cleavage of aryl diamines and synthesis of quinones

A novel synthetic utility of hypervalent iodine reagent, (diacetoxyiodo)benzene for diamino aryl carbon-carbon cleavage is described. 1,2-Diamino aryl compounds were successfully converted into the corresponding nitriles, while the developed method was also useful for the preparation of quinones from corresponding 1,4-diamino aryl compounds. The advantages of this protocol are shorter reaction times and mild reaction conditions to obtain moderate to good yields.

Reaction of anthrone and its 1- and 4-substituted derivatives with sulfur in the presence of nucleophiles

Anthrone and its 1-substituted derivatives react with molecular sulfur in the presence of nucleophiles (aromatic amines, hydrazine, substituted hydrazines, and malononitrile) to give intermediate monothioanthraquinones which are then converted into mixtures of the corresponding anthraquinones and 10-imino-, 10-hydrazono-, or 10-dicyanomethylene-9,10-dihydroanthracen-9-ones. Unlike 1-substituted derivatives, 4-substituted anthrones react with sulfur in the presence of phenylhydrazine to give only 1-substituted anthraquinones.

1-Anthraquinonediazonium Tetrachlorocuprate(II) and Its Dediazotization

1-Anthraquinonediazonium tetrachlorocuprate(II) was synthesized and underwent dediazotization in polar solvents at ambient temperature to give 1-chloroanthraquinone; furthermore, products of addition of 1-anthraquinonyl and a chlorine atom or hydroxy group to the double bond were obtained in the presence of esters of acrylic acid.

Application of Organolithium and Related Reagents in Synthesis XVI: Synthetic Strategies Based on Aromatic Metallation. A Concise Regiospecific Conversion of Chlorobenzoic Acids into their Benzylated Derivatives

The reaction of benzyl bromide with bis-(N- and C-ortho)-lithiated chloroanilides 4, 5, and 6 has been examined.It has been found that in the case where the lithiated compound was derived from meta-methoxyanilides, pre-addition of LiBr or TMEDA was required to achieve C-benzylation.These results were accounted for by the conversion of the usually formed dimer into a mixed dimer with the LiBr or TMEDA complex in which the C-lithium bond appears to be more accessible towards electrophiles.The practical synthesis of o-benzylchlorobenzoic acids 10, 11, and 12 was accomplished via ionic reductive cleavage (Et3SiH/TiCl4) of the corresponding phthalides 18, 19, and 20.The acids 10, 11b, and 11c afforded the corresponding anthrones, upon treatment with trifluoroacetic anhydride which were oxidized by chromium trioxide to the new chloroantraquinones 21, 22, and 23. - Keywords: Chlorophthalides; Reduction; Benzylation; Benzylbenzoic acids; Chloroantraquinones

Process for purifying crude monochloro- and monobromoanthraquinone

A process for purifying crude monochloro- or monobromoanthraquinone is described. In this process, monochloro- or monobromoanthraquinone which contains by-products as impurities is mixed with a hot non-polar aliphatic solvent in such a ratio that more than half of the crude product goes into solution and the remainder which contains the impurities forms a second lower phase, said eutectic melt is separated, and the saturated solution is allowed to cool, and the monochloro- or monobromoanthraquinone, which precipitates in pure form, is isolated.

PHOTOCHEMICAL REACTIONS OF CHLOROANTHRAQUINONES

Irradation of 1,5-dichloroanthraquionone (1,5-DCAQ) with 366 nm light in ethanol gives anthrahydroquinone (AQH2) as a final product.This is interpreted interms of the following cosecutive reactions; 1,5-DCAQ --hν--> 1,5-dichloroanthrahydroquinone --hν--> 1-chloroanthraquinone --hν--> 1-chloroanthrahydroquinone --hν--> anthraquinone --hν--> AQH2.Similar reactions were also observed for other α-chloroanthraquinones.

Triazinyl dyes

Vat dyestuffs of the formula EQU1 wherein R represents alkyl with 1 to 4 carbon atoms, R1 and R2 represent hydrogen or alkyl with 1 to 4 carbon atoms and each of A1 and A2 represents a vattable radical with 3 to 7 condensed rings are characterized by improved resistance to alkali and are suitable for dyeing and printing the most diverse materials, in particular fibers made from natural or regenerated cellulose.

Production of 1-chloroanthraquinone

1-Chloroanthraquinone is produced by decarboxylation of 4-chloroanthraquinone-1-carboxylic acid in the presence of a carboxamide. The product is a starting material for the production of dyes, pest control agents and pigments.