10381-82-5

Basic information

• Product Name: xanthobine
• Synonyms: xanthobine;8-BROMOCAFFEINE;1,3,7-Trimethyl-8-bromo-7H-purine-2,6(1H,3H)-dione;1,3,7-Trimethyl-8-bromoxanthine;8-Bromo-3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione;Xanthobin;8-bromo-1,3,7-trimethylpurine-2,6-dione;8-Bromo-1,3,7-trimethylxanthine
• CAS NO: 10381-82-5
• Molecular Formula: C₈H₉BrN₄O₂
• Molecular Weight: 273.08666
• Mol File: 10381-82-5.mol
• Article Data: 17

Chemical Properties

• Melting Point: 208-210°C
• Boiling Point: 440.1°Cat760mmHg
• Flash Point: 220°C
• Appearance: /
• Density: 1.87g/cm³
• Vapor Pressure: 6.04E-08mmHg at 25°C
• Refractive Index: 1.724
• CAS DataBase Reference: xanthobine(CAS DataBase Reference)
• NIST Chemistry Reference: xanthobine(10381-82-5)
• EPA Substance Registry System: xanthobine(10381-82-5)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• Hazardous Substances Data: 10381-82-5(Hazardous Substances Data)

Usage

Uses

8-Bromo-1,3,7-trimethylxanthine is an intermediate in the synthesis of 1,3,7-Trimethyluric Acid (T798000) is a caffeine derivative, and a methyl derivative of uric acid. Detected as a urine marker of caffeine consumption.

InChI:InChI=1/C8H9BrN4O2/c1-11-4-5(10-7(11)9)12(2)8(15)13(3)6(4)14/h1-3H3

Upstream product

• 58-08-2 3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione 
• 42297-40-5 1,3,7-trimethyl-2,6-dioxo-8-nitro-1H,3H,7H-xanthine 
• 10381-75-6 8-bromotheophylline 
• 74-88-4 methyl iodide 
• 6937-66-2 8,8'-mercuribis-caffeine 
• 6336-13-6 8-acetoxymercuri-caffeine 
• 77-78-1 dimethyl sulfate 
• 93703-24-3 3-methyl-8-bromoxanthine 

Downstream Products

• 4921-49-7 8-chlorocaffeine 
• 76-84-6 triphenylmethyl alcohol 
• 92-52-4 biphenyl 
• 108-95-2 phenol 
• 1790-74-5 1,3,7-trimethyl-8-thio-uric acid 
• 53703-63-2 8-hydrazino-1,3,7-trimethyl-3,7-dihydropurine-2,6-dione 
• 5415-44-1 1,3,7-trimethyluric acid 
• 99765-13-6 (E)-8-(2-Phenylethenyl)-3,7-dihydro-1,3,7-trimethyl-1H-purin-2,6-dion 
• 6439-88-9 1,3,7-trimethyl-8-phenylxanthine 
• 1388116-81-1 8-hydroxyamino-1,3,7-trimethyl-3,7-dihydropurine-2,6-dione 
• 619-72-7 4-nitrobenzonitrile 
• 1276683-39-6 1-benzhydryl-4-[1,3,7-trimethyl-2,6(3H,7H)-dioxo-1H-purine-8-yl]piperazine 
• 1268823-08-0 1,3,7-trimethyl-8-(3',4'-dimethoxyphenyl) xanthine 
• 6287-54-3 1,3,7-trimethyl-8-(methylthio)-1H-purine-2,6(3H,7H)-dione 

Relevant articles and documents

Synthesis of palladium complexes with anionic N,NR- or neutral NH,NR-theophylline-derived NHC ligands

Four C8-halogenated theophyllines (1–4) featuring N7-methyl or N7-allyl and C8-chloro or C8-bromo substituents have been prepared. The halogenotheophyllines react with [Pd(PPh3)4] in an oxidative addition to give complexes of type trans-[Pd(theophyllinato)X(PPh3)2] (trans-[5]–trans-[8]). The protonation of the unsubstituted theophyllinato ring-nitrogen atom to give the pNHC complexes was achieved either by performing the oxidative addition of 1 in the presence of NH4BF4 to give complex trans-[9]BF4 or by N-protonation of the coordinated theophyllinato ligand in trans-[6]–trans-[8] with HBF4·Et2O to give complexes trans-[10]BF4–trans-[12]BF4. The molecular structures of trans-[5], trans-[7], trans-[9]BF4, trans-[11]BF4 and trans-[12]BF4 were determined by X-ray diffraction showing significant differences of comparable metric parameters in the theophylline-derived five-membered diaminoheterocycles. No interaction of the N-allyl substituents with the metal center was observed.

Synthetic Transformations of Sesquiterpene Lactones. 11.* Conjugates Based on Caffeine and Eudesmanolides with N-Containing Linkers

8-(Aminoalkylamino)caffeine or 8-(piperazinyl)caffeine were formed in high yields by reacting 8-bromo- or 8-chlorocaffeine with linear and cyclic diamines using microwave-assisted organic synthesis. These amines were highly reactive in Michael reactions with sesquiterpene lactones containing active methylene groups. Conjugates with caffeine and eudesmanolide moieties bonded by a N-containing linker were synthesized.

8-Ethynylxanthines as promising antiproliferative agents, angiogenesis inhibitors, and calcium channel activity modulators

[Figure not available: see fulltext.] Synthetic procedures for the preparation of 8-ethynylxanthines by treating 8-bromocaffeine and 8-bromopentoxifylline with terminal acetylenes were elaborated. Certain ethynylxanthine derivatives exhibit high in vitro antiproliferative activity against a panel of cancer cell lines, matrix metalloproteinase and in vitro angiogenesis inhibitory activity. Ca2+ channel blocking and agonist activity of the synthesized ethynylxanthines was discussed based on data obtained on the H9C2, SH-SY5Y, and A7R5 cell lines.