50-66-8

Basic information

• Product Name: 6-METHYLMERCAPTOPURINE
• Synonyms: 6-METHYLMERCAPTOPURINE;6-(METHYLSULFANYL)-9H-PURINE;6-(METHYLTHIO)PURINE;1H-Purine, 6-(methylthio)-;6-(Methylsulfanyl)-7H-purine;6-(methylthio)-1h-purin;6-(methylthio)-purin;6-Methyl MP
• CAS NO: 50-66-8
• Molecular Formula: C₆H₆N₄S
• Molecular Weight: 166.2
• EINECS: 200-057-3
• Product Categories: Bases & Related Reagents;Intermediates & Fine Chemicals;Metabolites & Impurities;Nucleotides;Pharmaceuticals
• Mol File: 50-66-8.mol
• Article Data: 12

Chemical Properties

• Melting Point: 219-223 °C
• Boiling Point: 470.2 °C at 760 mmHg
• Flash Point: 238.2 °C
• Appearance: White/Powder
• Density: 1.380 (estimate)
• Vapor Pressure: 0.00351mmHg at 25°C
• Refractive Index: 1.5605 (estimate)
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• Water Solubility: Soluble in water (769 mg/L).
• Stability: Hygroscopic
• BRN: 7695
• CAS DataBase Reference: 6-METHYLMERCAPTOPURINE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-METHYLMERCAPTOPURINE(50-66-8)
• EPA Substance Registry System: 6-METHYLMERCAPTOPURINE(50-66-8)

Safety Data

• Safety Statements: 24/25
• RTECS: UO8976000
• Hazardous Substances Data: 50-66-8(Hazardous Substances Data)

Usage

Chemical Properties

white powder

Uses

6-(Methylthio)purine is an immunosuppressive drug used to treat leukemia.

InChI:InChI=1/C6H6N4S/c1-11-6-4-5(8-2-7-4)9-3-10-6/h2-4H,1H3

Upstream product

• 353-43-5 boron dimethyl-trifluoro sulphide 
• 87-42-3 6-chloro-7H-purine 
• 157930-09-1 6-Mercaptopurine 
• 74-88-4 methyl iodide 
• 87-42-3 6-chloropurine 
• 5188-07-8 sodium thiomethoxide 
• 14031-35-7 S-Adenosyl-L-methionine 
• 50-44-2 6-mercaptopurine 
• 342-69-8 6-methylmercaptopurine riboside 
• 85110-41-4 9-(1-Ethoxyethyl-1)-6-methylthiopurine 
• 485-80-3 S-adenosyl-L-methionine 
• 6258-60-2 p-methoxybenzylmercaptan 
• 157930-09-1 6-Mercaptopurine 
• 68-94-0 1,7-dihydro-6H-purin-6-one 

Downstream Products

• 2846-96-0 6-morpholino-7⁽⁹⁾H-purine 
• 525-81-5 (7(9)H-purin-6-yl)-[2]thienylmethyl-amine 
• 16370-58-4 propyl-(7(9)H-purin-6-yl)-amine 
• 13268-73-0 6-(2-methylbenzylamino)purine 
• 88166-55-6 dodecyl-(7⁽⁹⁾H-purin-6-yl)-amine 
• 36412-32-5 octyl-(7(9)H-purin-6-yl)-amine 
• 14333-96-1 hexyl-(7⁽⁹⁾H-purin-6-yl)-amine 
• 14814-48-3 heptyl-(7(9)H-purin-6-yl)-amine 
• 15500-82-0 (2-phenoxy-propyl)-(7⁽⁹⁾H-purin-6-yl)-amine 
• 20366-83-0 6-(2-hydroxybenzylamino)purine 
• 15500-86-4 (4-phenoxy-butyl)-(7⁽⁹⁾H-purin-6-yl)-amine 
• 15396-43-7 (3-phenyl-propyl)-(7⁽⁹⁾H-purin-6-yl)-amine 
• 99989-91-0 4-[(7⁽⁹⁾H-purin-6-ylamino)-methyl]-benzenesulfonic acid 
• 5450-44-2 (4-chloro-phenyl)-(7⁽⁹⁾H-purin-6-yl)-amine 

Relevant articles and documents

Human thiopurine methyltransferase: No evidence of activation by its substrates

A HPLC assay was developed to assay baculovirus expressed human thiopurine methyltransferase activity. Using 6-mercaptopurine as substrate, the expressed thiopurine methyltransferase was found to have an apparent Km of 0.99 mM and a Vmax of 19 nmoles/mg/min. These values are in agreement with those determined using the standard radiometric assay for thiopurine methyltransferase activity. The effects of 6-thioguanine on 6-mercaptopurine metabolism were determined. 6-Thioguanine was found to be a mixed inhibitor of 6-mercaptopurine methylation.

Metal-Free Aminomethylation of Aromatic Sulfones Promoted by Eosin Y

A metal-free α-aminomethylation of heteroaryls promoted by eosin Y under green light irradiation is reported. A large variety of α-trimethylsilylamines as precursor of α-aminomethyl radical species were engaged to functionalize sulfonyl-heteroaryls following a Homolytic Aromatic Substitution (HAS) pathway. This method has provided a range of α-aminoheteroaryl compounds including a functionalized natural product. The mechanism of this late-stage functionalization of aryls was investigated and suggests the formation of a sulfonyl radical intermediate over a reductive quenching cycle.

BF3·SMe2 for Thiomethylation, Nitro Reduction and Tandem Reduction/SMe Insertion of Nitrogen Heterocycles

Herein, a general, solvent-free and straightforward thiomethylation of electron deficient heterocycles using BF3·SMe2 as a dual thiomethyl source and Lewis acidic activator is presented. A range of heterocycles including pyrimidine, pyrazine, pyridazine, thiazole and purine derivatives were successfully substituted using this method. An unexpected reductive property of BF3·SMe2 towards nitropyridines was also discovered including an intriguing tandem reduction/SMe insertion process in certain substrates. Notable features of the present work include its convenience and use of a non-malodorous reagent while the discovery of novel chemical transformations using BF3·SMe2 provides fundamental new insights into the reactivity of this commonly employed reagent.