3485-80-1

Basic information

• Product Name: 1-iodoanthracene-9,10-dione
• Synonyms: 1-Iodo-9,10-anthraquinone; 1-Iodo-anthraquinone; 9,10-anthracenedione, 1-iodo-; Anthraquinone, 1-iodo-
• CAS NO: 3485-80-1
• Molecular Formula: C₁₄H₇IO₂
• Molecular Weight: 334.1086
• Mol File: 3485-80-1.mol

Chemical Properties

• Boiling Point: 462.6°C at 760 mmHg
• Flash Point: 233.6°C
• Density: 1.844g/cm³
• Vapor Pressure: 9.72E-09mmHg at 25°C
• Refractive Index: 1.72
• CAS DataBase Reference: 1-iodoanthracene-9,10-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1-iodoanthracene-9,10-dione(3485-80-1)
• EPA Substance Registry System: 1-iodoanthracene-9,10-dione(3485-80-1)

Safety Data

• Hazardous Substances Data: 3485-80-1(Hazardous Substances Data)

Usage

Chemical Family

1-Iodoanthracene-9,10-dione belongs to the anthracenedione family.

Iodine Content

It contains an iodine atom.

Physical Appearance

It is a yellow to green powder.

Solubility

It is insoluble in water but soluble in organic solvents.

Uses

It is commonly used as a reagent in organic synthesis.

Reactivity

It can undergo halogenation, reduction, and substitution reactions.

Photophysical Properties

It has photophysical properties, making it suitable for use in the field of photophysics.

Photochemical Properties

It has photochemical properties, making it suitable for use in the field of photochemistry.

Potential Applications

It has potential applications in dye synthesis and as a building block in the preparation of complex organic molecules.

Upstream product

• 82-45-1 1-amino-9,10-anthracenedione 

Downstream Products

• 914-20-5 [1,1']bianthryl-9,10,9',10'-tetraone 
• 40650-85-9 1-diphenylamino-anthraquinone 
• 78053-66-4 1-(phenylethynyl)-9,10-anthraquinone 
• 152190-76-6 1-(phenylsulfonylmethoxycarbonylmethyl)anthraquinone 
• 152190-64-2 1-(phenylsulfonylethoxycarbonylmethyl)anthraquinone 
• 84-65-1 9,10-phenanthrenequinone 
• 129-45-3 1-butylamino-9,10-anthraquinone 
• 83790-95-8 6-oxo-1-phenyl-2-(phenylformylmethylene)-2,6-dihydroaceanthrylene 
• 1714-14-3 1-phenyl-anthraquinone 
• 853993-35-8 1-(4-isopropylphenyl)-9,10-anthraquinone 
• 20600-74-2 1-(4-methylphenyl)-9,10-anthraquinone 
• 853993-37-0 1-(3-isopropylphenyl)-9,10-anthraquinone 
• 853993-38-1 1-(3,5-diisopropyl-phenyl)-anthraquinone 
• 853993-36-9 1-(4-t-butylphenyl)-9,10-anthraquinone 

Relevant articles and documents

Direct sequential C-H iodination/organoyl-thiolation for the benzenoid A-ring modification of quinonoid deactivated systems: A new protocol for potent trypanocidal quinones

We report a sequential C-H iodination/organoyl-thiolation of naphthoquinones and their relevant trypanocidal activity. Under a combination of AgSR with a copper source, sulfur-substituted benzenoid quinones were prepared in high yields (generally >90%). This provides an efficient and general method for preparing A-ring modified naphthoquinoidal systems, recognized as a challenge in quinone chemistry.

Late stage iodination of biologically active agents using a one-pot process from aryl amines

A simple and effective one-pot tandem procedure that generates aryl iodides from readily available aryl amines via stable diazonium salts has been developed. The operationally simple procedure and mild conditions allow late-stage iodination of a wide range of aryl compounds bearing various functional groups and substitution patterns. A novel synthetic strategy involving the preparation of nitroaryl compounds followed by a chemoselective tin(ii) dichloride reduction and the use of the one-pot diazotisation-iodination transformation was also developed. The general applicability of this approach was demonstrated with the preparation of a number of medicinally important compounds including CNS1261, a SPECT imaging agent of the N-methyl-d-aspartate (NMDA) receptor and IBOX, a compound used to detect amyloid plaques in the brain.

A new, one-step, effective protocol for the iodination of aromatic and heterocyclic compounds via aprotic diazotization of amines

We have developed a convenient one-step preparation of aromatic and some heterocyclic iodides by the sequential diazotization-iodination of the aromatic amines with a KI/NaNO2/p-TsOH system in acetonitrile at room temperature. This method has general character and allows aryl iodides with either donor or acceptor substituents in various positions to be obtained from the corresponding amines in 50-90% yield. Georg Thieme Verlag Stuttgart.

Waste-free chemistry of diazonium salts and benign separation of coupling products in solid salt reactions

Gas-solid and solid-solid techniques allow for waste-free and quantitative syntheses in the chemistry of diazonium salts. Five techniques for diazotations with the reactive gases NO2, NO and NOCl are studied. Two types are mechanistically investigated with atomic force microscopy (AFM) and are interpreted on the basis of known crystal packings. The same principles apply to the cascade reactions that had been derived from one-step reactions. Solid diazonium salts couple quantitatively with solid diphenylamine and anilines to give the triazenes. Azo couplings are achieved with quantitative yields by cautious co-grinding of solid diazonium salts with β-naphthol and C-H acidic heterocycles, such as barbituric acids or pyrazolinones. Solid diazonium salts may be more easily applied in a stoichiometric ratio for couplings in solution. Co-grinding of solid diazonium salts with KI gives quantitative yields of various solid aryl iodides. The unavoidable coupling products in salt reactions are completely separated from the insoluble products in a highly benign manner. The solid-state reactions compare favourably with similar solution reactions that produce much waste. The structures of the products are elucidated with IR and NMR spectroscopy and mass spectrometry, while the tautomeric properties of the compounds are studied with density functional calculations at the B3LYP/6-31G* and BLYP/6-31G** levels.