3647-48-1

Basic information

• Product Name: 6-AMINO-2-MERCAPTOPURINE
• Synonyms: 2-mercaptoadenine;2-thioadenine;6-amino-1,3-dihydro-2h-purine-2-thion;6-amino-purine-2-thio;6-AMINO-2-MERCAPTOPURINE;6-Amino-1,7-dihydro-2H-purine-2-thione;6-Amino-2-mercapto-9H-purine;6-Amino-7H-purine-2-thiol
• CAS NO: 3647-48-1
• Molecular Formula: C₅H₅N₅S
• Molecular Weight: 167.19
• Mol File: 3647-48-1.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 273.3°Cat760mmHg
• Flash Point: 119.1°C
• Appearance: /
• Density: 2.08g/cm³
• Vapor Pressure: 0.000373mmHg at 25°C
• Refractive Index: 2.07
• PKA: 5.81±0.40(Predicted)
• CAS DataBase Reference: 6-AMINO-2-MERCAPTOPURINE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-AMINO-2-MERCAPTOPURINE(3647-48-1)
• EPA Substance Registry System: 6-AMINO-2-MERCAPTOPURINE(3647-48-1)

Safety Data

• Hazardous Substances Data: 3647-48-1(Hazardous Substances Data)

Usage

Description

6-AMINO-2-MERCAPTOPURINE, also known as 6-Aminopurine, is an organic compound with the molecular formula C5H4N4S. It is a purine derivative characterized by the presence of an amino group at the 6th position and a thiol (mercapto) group at the 2nd position. 6-AMINO-2-MERCAPTOPURINE is known for its biological and chemical properties, making it a versatile molecule with various applications in different fields.

Uses

Used in Chemical Synthesis:
6-AMINO-2-MERCAPTOPURINE is used as a reagent for the preparation of alkylated heterocyclic bases. Its unique structure allows it to be a valuable building block in the synthesis of various complex organic molecules, particularly those with potential applications in pharmaceuticals and materials science.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 6-AMINO-2-MERCAPTOPURINE is utilized as an intermediate in the development of new drugs, especially those targeting purine-related metabolic pathways. Its ability to form covalent bonds with other molecules makes it a promising candidate for the design of novel therapeutic agents.
Used in Biochemical Studies:
6-AMINO-2-MERCAPTOPURINE is also employed in biochemical research as a tool to study the mechanisms of enzyme-catalyzed reactions involving purine nucleotides. Its reactivity with various enzymes and its ability to act as a substrate or inhibitor can provide valuable insights into the regulation of cellular processes.
Used in Analytical Chemistry:
As an analytical reagent, 6-AMINO-2-MERCAPTOPURINE can be used to develop new methods for the detection and quantification of purine derivatives in biological samples. Its unique chemical properties make it suitable for the development of selective and sensitive assays, contributing to the advancement of analytical techniques in the field.

InChI:InChI=1/C5H5N5S/c6-3-2-4(8-1-7-2)10-5(11)9-3/h1-2H,(H3,6,7,8,9,10,11)

Upstream product

• 77287-34-4 formamide 
• 1073-99-0 4,5,6-triamino-2-mercapto-pyrimidine 
• 753502-74-8 N-(4,6-diamino-2-thioxo-1,2-dihydro-pyrimidin-5-yl)-formamide 

Downstream Products

• 73-24-5 7H-purin-6-ylamine 
• 28128-25-8 2-bromo-9H-purin-6-amine 
• 68-94-0 1,7-dihydro-6H-purin-6-one 
• 43003-87-8 3-ethyl-3H-purin-6-ylamine 

Relevant articles and documents

Method for synthesis of adenine (by machine translation)

The invention discloses a synthetic method for adenine. Malononitrile and thiourea are employed as raw materials. The raw materials are subjected to a cyclization reaction under action of sodium alkoxide, and 4,6-diamino-2-sulfydryl pyrimidine. Then through three reaction routes, adenine is obtained. Though the method has many reaction steps, no refining or drying are needed for the product of each reaction step, the product can be used in the next reaction step, and the operation is simple. The raw materials are easily available, the prices are relatively low, the reaction conditions are mild, the operation is simple, the reaction steps are decreased, the reaction time is shortened, the overall reaction yield is high, and the synthetic method is suitable for industrial production.

PURINE DERIVATIVES HAVING PHOSPHODIESTERASE IV INHIBITION ACTIVITY

A compound of the formula: wherein R2 is O or S; R3, R6a and R8 are the same or different and each represent a C1-8 alkyl which is unbranched or branched and unsubstituted or substituted with OH, alkoxy, CO2H, =NOH, =NOCONH2, or =O; C3-8 cycloalkyl which is unsubstituted or substituted with OH, alkoxy, CO2H, =NOH, =NOCONH2, or =O; C4-8 cycloalkylalkyl wherein the cycloalkyl portion is unsubstituted or substituted with OH, alkoxy, CO2H, =NOH, =NOCONH2, or =O; aryl which is unsubstituted or substituted with Cl, NH2, alkylamino, dialkylamino, amido, C1-C8 alkylamido, C1-C3 dialkylamido, OH, alkoxy, HC=NOH, HC=NOCONH2, C1-C3 alkyl, phenyl or benzyl; aralkyl (C1-4); heterocyclyl; heterocyclylalkyl (C1-C4); and heteroaryl; R6b represents a H or R6a, or together R6b, N, and R6a make a 3 to 8 member ring containing at least one carbon, from one to three nitrogen atoms, from zero to two oxygen atoms, from zero to two sulfur atoms, said ring optionally substituted with alkoxy, CO2H, CONH2, =NOH, =NOCONH2, =O; and where aryl is phenyl or naphthyl, the heterocyclyl is a 5, 6 or 7 membered ring including from one to three nitrogen atoms, and from zero to two oxygen atoms, from zero to two sulfur atoms, and can be substituted as in aryl on the carbons or nitrogens of that ring; or a pharmaceutically acceptable salt thereof, provided that when R3 is propyl, R8 is not cyclopentyl, noradamantyl, or dicyclopropylmethyl.