85-18-7

Basic information

• Product Name: 8-Chlorotheophylline
• Synonyms: H-Purine-2,6-dione, 8-chloro-3,7-dihydro-1,3-dimethyl-;1,3-Dimethyl-8-chloro-9H-purine-2,6(1H,3H)-dione;8-Chloro-1,2,3,6-tetrahydro-1,3-dimethyl-7H-purine-2,6-dione;8-Chlorotheophylline,99%;8-chloro-3,9-dihydro-1,3-diMethyl-1H-Purine-2,6-dione;NSC 6113;8-chloro-1,3-diMethyl-1H-purine-2,6(3H,7H)-dione;8-CHLOROTHEOPHYLLINE
• CAS NO: 85-18-7
• Molecular Formula: C₇H₇ClN₄O₂
• Molecular Weight: 214.61
• EINECS: 201-590-4
• Product Categories: Bases & Related Reagents;Heterocycles;Nucleotides;Pharmaceutical Raw Materials;Alkaloids (Others);Alkaloids;Biochemistry
• Mol File: 85-18-7.mol
• Article Data: 6

Chemical Properties

• Melting Point: 290 °C (dec.)(lit.)
• Boiling Point: 455 °C at 760 mmHg
• Flash Point: 229 °C
• Appearance: white to light yellow crystal powder
• Density: 1.8869 (rough estimate)
• Vapor Pressure: 1.82E-08mmHg at 25°C
• Refractive Index: 1.5560 (estimate)
• Storage Temp.: Refrigerator
• Solubility: Soluble in sodium hydroxide.
• PKA: pKa 5.28 (Uncertain)
• Water Solubility: SLIGHTLY SOLUBLE
• BRN: 203068
• CAS DataBase Reference: 8-Chlorotheophylline(CAS DataBase Reference)
• NIST Chemistry Reference: 8-Chlorotheophylline(85-18-7)
• EPA Substance Registry System: 8-Chlorotheophylline(85-18-7)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38-22
• Safety Statements: 36-37/39-26
• RIDADR: 2811
• WGK Germany: 3
• RTECS: XH5063000
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 85-18-7(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powder

Uses

8-Chlorotheophylline is a stimulant drug. It can be used as a binding agent to form stable salts of pharmaceutical drugs.

Definition

ChEBI: 1,3-Dimethylxanthine in which the hydrogen at position 8 is substituted by chlorine.

Purification Methods

It crystallises from H2O or EtOH (m 304o, dec). The choline salt crystallises from H2O with m 60-62o (2 H2O) and m 97-99o (anhydrous). [Beilstein 26 H 473, II 276, 26 III/IV 2442.]

InChI:InChI=1/C7H7ClN4O2/c1-11-4-3(9-6(8)10-4)5(13)12(2)7(11)14/h1-2H3,(H,9,10)

Upstream product

• 58-55-9 theophylline 
• 944-73-0 1,3-dimethyluric acid 
• 7647-01-0 hydrogenchloride 
• 2099-73-2 8-nitrotheophylline 
• 52943-89-2 8-pyridinium theophyllinate 
• 148122-86-5 8-trimethylammonium theophyllinate 

Downstream Products

• 4638-03-3 3-allyloxy-1-chloro-2-propanol 
• 145072-22-6 7-Allyloxymethyl-1,3-dimethyl-6,7-dihydro-1H-oxazolo[2,3-f]purine-2,4-dione 
• 58-55-9 theophylline 
• 147699-92-1 1,3-dimethyl-8-(E)-styryl-3,7-dihydro-1H-purine-2,6-dione 
• 93214-88-1 8-biphenyl-1,3-dimethyl-3,7-dihydro-1H-purine-2,6-dione 
• 109286-40-0 7-benzyl-8-chloro-1,3-dimethyl-1,3,7-trihydropurine-2,6-dione 
• 4921-49-7 8-chlorocaffeine 
• 961-45-5 1,3-dimethyl-8-phenylxanthine 
• 346597-03-3 7-(2-bromobenzyl)-8-chloro-1,3-dimethyl-3,7-dihydropurine-2,6-dione 
• 586408-02-8 4-[7-(2-Butynyl)-1,3-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester 
• 57260-71-6 1-t-Butoxycarbonylpiperazine 
• 78960-54-0 1,3-dimethyl-2,4-dioxo-7-phenoxymethyl-1,2,3,4,6,7-hexahydrooxazolido<2,3-f>purine 
• 59426-33-4 (8-chloro-1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydro-purin-7-yl)-acetic acid 
• 860710-53-8 8-chloro-8'-diethylamino-1,3,1',3'-tetramethyl-3,7,3',7'-tetrahydro-7,7'-ethanediyl-bis-purine-2,6-dione 

Relevant articles and documents

Reactions of theophyllines. Chemical conversions of 8-aminotheophyllinates

Thermally stable, colored 8-aminotheophyllinates (betaine derivatives of theophylline) form unstable, colorless salts with strong mineral acids and undergo partial decomposition to a uric acid upon prolonged refluxing with concentrated base solution. Substituted 8-pyridinium theophyllinates readily take part in typical reactions of the functional group in the substituted pyridine ring with retention of the betaine structure. The formation of the synthesized compounds was confirmed by IR and NMR spectroscopy.

Preparation method of low-cost 8-chlorotheophylline

The invention discloses a preparation method of low-cost 8-chlorotheophylline. The preparation method of the low-cost 8-chlorotheophylline comprises the following steps: adding theophylline into a mixed solution of DMF and SOCl2, introducing chlorine to react, and crystallizing, washing and drying after the reaction to obtain the final product. According to the method, the target product is synthesized by taking the recyclable DMF as a solvent at one step and the finished product can be obtained by pulping with tap water, so that the cost is low, the pollution is low and the yield is high.

Purines. XIV [1]. Synthesis and properties of 8-nitroxanthine and its N- methyl derivatives

Xanthine (1) and its N-methyl derivatives 2-16 have been nitrated to the corresponding 8-nitro derivatives 17-32 under different reaction conditions. Nitration in glacial acetic acid with nitric acid works well with the N-7 unsubstituted and some of the 9-methylxanthines, respectively, whereas the 7- methylxanthine derivatives react best with nitronium tetrafluoroborate in sulfolane or glacial acetic acid. The 8-nitro group can be displaced nucleophilically to form 8-chloro-, 33, 34, 8-ethoxy-, 35, 36, and uric acid derivatives 37-40, respectively. The newly synthesized 8-nitroxanthines have been characterized by elemental analyses, pK-determinations and uv and 1H- nmr spectra.