5395-25-5

Basic information

• Product Name: N-hydroxy-9H-thioxanthen-9-imine 10,10-dioxide
• CAS NO: 5395-25-5
• Molecular Formula: C₁₃H₉NO₃S
• Molecular Weight: 259.2805
• Mol File: 5395-25-5.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 500.8°C at 760 mmHg
• Flash Point: 256.7°C
• Density: 1.45g/cm³
• Vapor Pressure: 7.55E-11mmHg at 25°C
• Refractive Index: 1.692
• CAS DataBase Reference: N-hydroxy-9H-thioxanthen-9-imine 10,10-dioxide(CAS DataBase Reference)
• NIST Chemistry Reference: N-hydroxy-9H-thioxanthen-9-imine 10,10-dioxide(5395-25-5)
• EPA Substance Registry System: N-hydroxy-9H-thioxanthen-9-imine 10,10-dioxide(5395-25-5)

Safety Data

• Hazardous Substances Data: 5395-25-5(Hazardous Substances Data)

Upstream product

• 492-22-8 thio-xanthene-9-one 
• 3166-15-2 thioxanthen-9-one 10,10-dioxide 

Relevant articles and documents

Relationship between structure of conjugated oxime esters and their ability to cleave DNA

The size and geometry of polycycles are critical to intercalation into DNA. This work involves the establishment of a new compound library that includes 35 O-benzoyl oxime esters with intercalators of five types. These conjugated compounds were synthesized by the condensation of substituted benzoyl chlorides (XC6H4COCl; X = H, Me, CN, F, and NO2) or naphthoyl chlorides with oximes of fluoren-9-one, 9,10-anthraquinone, xanthen-9-one, thioxanthen-9-one, and 9H-thioxanthen-9-one 10,10-dioxide to give the corresponding esters in 80-99% yields. All of these compounds could cleave DNA when photolyzed by UV light. Of these conjugates, 9,10-anthraquinone-O-9-(4- fluorobenzoyl)oxime with a binding constant of 4.49 × 104 M-1 cleaved DNA most efficiently. Examination of the structure-activity relationship supports a conclusion that two factors affect DNA-cleaving potency. These are (1) the planarity of the intercalating moiety, and (2) the size and substituents of the benzoyl ring. The DNA-cleaving ability followed the order 9,10-anthraquinone > fluoren-9-one ≥ xanthen-9-one ～ thioxanthen-9-one > 9H-thioxanthen-9-one 10,10-dioxide. The benzoyl-containing oxime ester conjugates were more active than the corresponding naphthoyl-containing conjugates. The potency that was associated with the different substituents on the benzoyl ring followed the order F > CN ≥ NO2 > Me ～ H.

New approach to biomimetic transamination using bifunctional [1,3]-proton transfer catalysis in thioxanthenyl dioxide imines

A pyridoxamine equivalent, 9-aminothioxanthene 10,10-dioxide, has been designed that is capable of affording transamination in good to excellent yields of natural as well as artificial amino acids. Amidines and guanidines in catalytic amounts were capable of performing [1,3]-proton transfer in the imines under mild conditions, whereas various simple amines failed. The use of chiral catalysts resulted in modest asymmetric induction (ee ≤ 45%). The electronic dependence in para-substituted phenyl glyoxylate imines, isotope effects, and computational studies support a stepwise, bifunctional mechanism for amidine and guanidine catalysts. Attempts toward an autocatalytic model system are described.