131-09-9

Basic information

• Product Name: 2-Chloroanthraquinone
• Synonyms: anthraquinone,2-chloro-;β-chloroanthrapuinone ;Melting point standard 2-chloroanthraquinone;2-Chloroanthraqukinone;MELTING POINT STANDARD 2-CHLORO- &;2-Chloranthrachinon;2-Chloroanthraquinone,99%;2-Chloroanthraquinone,97%
• CAS NO: 131-09-9
• Molecular Formula: C₁₄H₇ClO₂
• Molecular Weight: 242.66
• EINECS: 205-010-0
• Product Categories: Intermediates of Dyes and Pigments;Organics;Electronic Chemicals;Anthraquinones;Chloroanthraquine, etc.;C13 to C14;Carbonyl Compounds;Ketones;API Intermediate
• Mol File: 131-09-9.mol

Chemical Properties

• Melting Point: 209-211 °C(lit.)
• Boiling Point: 345.65°C (rough estimate)
• Flash Point: 179.7 °C
• Appearance: beige powder
• Density: 1.2377 (rough estimate)
• Vapor Pressure: 1.1E-07mmHg at 25°C
• Refractive Index: 1.5380 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility: insoluble
• BRN: 2051842
• CAS DataBase Reference: 2-Chloroanthraquinone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloroanthraquinone(131-09-9)
• EPA Substance Registry System: 2-Chloroanthraquinone(131-09-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-43-36/37
• Safety Statements: 26-36-37/39-24
• WGK Germany: 1
• RTECS: CB6151000
• F: 10
• TSCA: Yes
• Hazardous Substances Data: 131-09-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Chloroanthraquinone is used as an intermediate in the synthesis of various pharmaceutical compounds due to its unique chemical structure and reactivity. Its ability to form different types of chemical bonds makes it a valuable building block for the development of new drugs.
Used in Analytical Chemistry:
2-Chloroanthraquinone is used as a photo-reagent for the analysis of ginsenosides, a group of compounds found in ginseng that have various pharmacological properties. The photoreduction fluorescence (PRF) detection method employs 2-Chloroanthraquinone to analyze and quantify ginsenosides, providing a reliable and sensitive technique for their determination.

Synthesis Reference(s)

Tetrahedron Letters, 24, p. 5499, 1983 DOI: 10.1016/S0040-4039(00)94122-4

InChI:InChI=1/C14H9ClO2/c15-8-5-6-11-12(7-8)14(17)10-4-2-1-3-9(10)13(11)16/h1-7,9-10H

Upstream product

• 110-89-4 piperidine 
• 53175-28-3 2-chloro-2-butenal 
• 64-17-5 ethanol 
• 64-19-7 acetic acid 
• 130-15-4 [1,4]naphthoquinone 
• 87-41-2 2-benzofuran-1(3H)-one 
• 108-90-7 chlorobenzene 
• 859944-53-9 3,10,10-trichloro-anthrone 
• 82-44-0 1-chloroanthracene-9,10-dione 
• 32017-70-2 methyl 2-(4-chlorobenzoyl)benzoate 
• 15100-53-5 anthracene-2-sulfonic acid 
• 84-48-0 2-sulfo-anthraquinone 
• 13450-37-8 o-(3-chloro-benzoyl)-benzoic acid 
• 42156-76-3 2-(4-chloro-benzoyl)-benzoyl chloride 

Downstream Products

• 69470-36-6 2-chloro-9,10-diphenyl-9,10-dihydro-anthracene-9,10-diol 
• 6417-48-7 1,5-bis-(9,10-dioxo-9,10-dihydro-[2]anthrylamino)-anthraquinone 
• 4003-36-5 NSC 74702 
• 5594-08-1 2-(toluene-4-sulfonyl)-anthraquinone 
• 13354-40-0 2-phenylsulfanyl-anthraquinone 
• 43217-28-3 2-chloro-9,10-diphenylanthracene 
• 605-32-3 2-hydroxy-9,10-anthraquinone 
• 6374-88-5 1-nitro-2-chloroanthraquinone 
• 72-48-0 1,2-dihydroxy-9,10-anthracenedione 
• 1594-46-3 1,2-dichloro-anthraquinone 
• 17135-78-3 2-chloroanthracene 
• 572-84-9 2-fluoroanthraquinone 
• 501076-50-2 2-hydrazino-anthraquinone 
• 117-79-3 2-aminoanthraquinone 

Relevant articles and documents

Intramolecular acylation of aryl- and aroyl-aliphatic acids by the action of pyrophosphoryl chloride and phosphorus oxychloride

Both pyrophosphoryl chloride and phosphorus oxychloride react with aryl aliphatic acids to form mixed anhydrides which undergo intramolecular acylation to afford cyclic ketones without the addition of a Friedel-Crafts catalyst. Aryl and aroyl-benzoic acids could be cyclized to the corresponding anthrones and anthraquinones respectively.

Conformational analysis of 2-anthryl-ethylene derivatives: Photochemical and computational investigation

2-Anthrylethylene derivatives 1 E-5 E and 1 Z are synthesized to study the cis-trans photoisomerization. Interestingly, unlike 9-anthrylethylene derivatives, 2-anthrylethylene derivatives 1 E to 5 E do not exhibit E(trans) to Z (cis) photoisomerization upon direct and triplet sensitization. One-way Z (cis) to E (trans) photoisomerization of 1 Z is found to be very efficient under direct and triplet sensitization conditions, demonstrating the involvement of both singlet and triplet states. 1 E-5 E exhibits excitation wavelength dependent fluorescence indicating the existence of conformers (rotamers) at room temperature, which is confirmed by fluorescence lifetimes measurements of compounds 1 E and 2 E. Theoretical studies are carried out at DFT and ab initio methodology and the calculated relative energy difference of the conformers is very small; it ranges between 2.9 kJ·mol-1 to 6.3 kJ·mol-1 for both ground and excited states.

Design, Synthesis, Molecular Docking, and Biological Evaluation of New Emodin Anthraquinone Derivatives as Potential Antitumor Substances

The emodin anthraquinone derivatives are generally used in traditional Chinese medicine due to their various pharmacological activities. In the present study, a series of emodin anthraquinone derivatives have been designed and synthesized, among which 1,3-dihydroxy-6,8-dimethoxyanthracene-9,10-dione is a natural compound that has been synthesized for the very first time, and 1,3-dimethoxy-5,8-dimethylanthracene-9,10-dione is a compound that has never been reported earlier. Interestingly, while total seven of these compounds showed neuraminidase inhibitory activity in influenza virus with inhibition rate more than 50 %, specific four compounds exhibited significant inhibition of tumor cell proliferation. The further results demonstrate that 1,3-dimethoxy-5,8-dimethylanthracene-9,10-dione showed the best anticancer activity among all the synthesized compounds by inducing highest apoptosis rate to HCT116 cancer cells and arresting their G0/G1 cell cycle phase, through elevation of intracellular level of reactive oxygen species (ROS). Moreover, the binding of 1,3-dimethoxy-5,8-dimethylanthracene-9,10-dione with BSA protein has thoroughly been investigated. Altogether, this study suggests the neuraminidase inhibitory activity and antitumor potential of the new emodin anthraquinone derivatives.

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 preparation of 2-substituted 1,4-naphthoquinone

A process for preparation of a 2-substituted-1,4-naphthoquinone which comprises oxidizing a 2-substituted naphthalene to obtain reaction products comprising a 2-substituted-1,4-naphthoquinone and a 6-substituted-1,4-naphthoquinone; adding a diene compound to the reaction products and heating the mixture to form a Diels-Alder reaction adduct between the diene compound and the 6-substituted-1,4-naphthoquinone in the reaction products; and separating the 2-substituted-1,4-naphthoquinone from the adduct.

Process for the preparation of anthraquinone and its substituted derivatives

A process for the preparation of anthraquinone compounds by condensation of phthalic anhydride with a benzene derivative wherein a mixture of hydrofluoric acid and boron trifluoride is utilized as catalyst.

Rh-CATALYZED OXIDATION OF ANTHRACENES TO ANTHRAQUINONES USING t-BUTYLHYDROPEROXIDE

Rh-catalyzed oxidation of 2-substituted anthracene with t-butylhydroperoxide affords anthraquinones in yields up to 90percent, while V-catalyzed oxidation and stoichiometric oxidation with CrO3 are less efficient.

Process for the preparation of anthraquinone compounds

The invention relates to the preparation of partially known anthraquinone compounds of the formula STR1 wherein Z1 represents an optionally substituted hydrocarbon radical, Z2 represents hydrogen or alkyl, one X represents a chlorine atom and the other X denotes a hydrogen atom, by subjecting technical chloroanthraquinone mixtures to a fractional vacuum distillation and reacting the 1,6(1,7)-dichloranthraquinone fraction thereby obtained with amines of the formula HNZ1 Z2. Moreover the invention relates to novel compounds of the above formula wherein Z2 is H and Z1 is alkyl, alkenyl, aralkyl or cycloalkyl. They are good dyestuffs for synthetic fibres or dyestuff intermediates.

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.