6374-87-4 Usage
Description
2-(Chloromethyl)anthraquinone is an anthraquinone derivative characterized by the presence of a chloromethyl group at the 2nd position. It is known for its versatile chemical properties and has been utilized in various synthetic processes and applications, particularly in the field of electrochemistry and dye synthesis.
Uses
Used in Chemical Synthesis:
2-(Chloromethyl)anthraquinone is used as a starting reagent for the synthesis of various complex organic compounds. It serves as a key intermediate in the production of specialized dyes and pigments, as well as in the creation of advanced metallophthalocyanines, which have potential applications in areas such as solar energy conversion and photocatalysis.
Used in Dye Synthesis:
2-(Chloromethyl)anthraquinone is used as a substrate in the synthesis of Cibanone yellow R, a vat dye. This dye finds applications in the textile industry for coloring fabrics, particularly those requiring high colorfastness and resistance to fading.
Used in Electrochemistry:
2-(Chloromethyl)anthraquinone is employed to modify the glassy carbon (GC) electrode surface, which is crucial for investigating the oxygen reduction reaction (ORR) in alkaline medium. This modification enhances the electrode's performance and provides valuable insights into the underlying electrochemical processes, contributing to the development of more efficient energy conversion systems.
Used in Pharmaceutical Applications:
Although not explicitly mentioned in the provided materials, anthraquinone derivatives, in general, have been explored for their potential applications in the pharmaceutical industry. They may exhibit various biological activities, such as anti-cancer, anti-inflammatory, and anti-parasitic properties, making them promising candidates for drug development.
Check Digit Verification of cas no
The CAS Registry Mumber 6374-87-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 6,3,7 and 4 respectively; the second part has 2 digits, 8 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 6374-87:
(6*6)+(5*3)+(4*7)+(3*4)+(2*8)+(1*7)=114
114 % 10 = 4
So 6374-87-4 is a valid CAS Registry Number.
InChI:InChI=1/C15H9ClO2/c16-8-9-5-6-12-13(7-9)15(18)11-4-2-1-3-10(11)14(12)17/h1-7H,8H2
6374-87-4Relevant articles and documents
S(RN)1 reactions of anthraquinone alkylating agents
Crozet,Vanelle,Jentzer,Donini,Maldonado
, p. 11253 - 11262 (2007/10/02)
The C-alkylation reaction of three reductive alkylating agents prepared from 2-methylanthraquinone by 2-nitropropane anion is shown to proceed by the S(RN)1 mechanism. The S(RN)1 mechanism is confirmed by the leaving group effect and the inhibitory effect of dioxygen, p-dinitrobenzene, cupric chloride and di-tert-butylnitroxide. This reaction can be extended to 1-methyl-3-nitropyrolidin-2-one anion.
2-Methylanthraquinone derivatives as potential bioreductive alkylating agents
Lin,Teicher,Sartorelli
, p. 1237 - 1242 (2007/10/02)
Hypoxic cells of solid tumors are an obstacle to effective cancer therapy. Since hypoxic cells remote from the tumor blood supply may have a greater capacity for reductive reactions than well-oxygenated cells, the authors have prepared a series of anthraquinone prodrugs which may be capable of generating a reactive quinonemethide species following enzymatic reduction to the hydroquinone and loss of the substituent on the methylene group in the 2 position. The synthesized 2-methyl-substituted anthraquinone derivatives have first half-wave reduction potentials of -0.52 to -0.56 V at pH 7.0, which are the lowest oxidation-reduction potentials of quinone bioreductive alkylating agents synthesized by this laboratory to date. Tests of the cytotoxicity of these agents to oxygenated and chronically hypoxic EMT6 tumor cells in culture demonstrated that 2-(hydroxymethyl)anthraquinone, 2-[(N-methylcarbamyl)-methyl]anthraquinone, 2-[(p-toluenesulfonyl)oxy]methyl]anthraquinone, and 2-(methoxymethyl)anthraquinone were significantly more toxic to hypoxic cells than to their normally aerated counterparts. The findings demonstrate differences between various leaving groups in the 2 position for the expression of differential cytotoxicity.
