4121-39-5

Basic information

• Product Name: NSC 77154
• Synonyms: NSC 77154;9-(2-Propenyl)adenine;9-Allyl-9H-purin-6-aMine;9-(prop-2-en-1-yl)-9H-purin-6-aMine;Tenofovir Impurity U;9-(2-propen-1-yl)-9H-Purin-6-amine
• CAS NO: 4121-39-5
• Molecular Formula: C₈H₉N₅
• Molecular Weight: 175.194
• Mol File: 4121-39-5.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 388.4 °C at 760 mmHg
• Flash Point: 188.7 °C
• Appearance: /
• Density: 1.39 g/cm³
• Vapor Pressure: 3.06E-06mmHg at 25°C
• Refractive Index: 1.714
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), DMSO (Slightly), Ethanol (Slightly), Methanol (Slightly)
• CAS DataBase Reference: NSC 77154(CAS DataBase Reference)
• NIST Chemistry Reference: NSC 77154(4121-39-5)
• EPA Substance Registry System: NSC 77154(4121-39-5)

Safety Data

• Hazardous Substances Data: 4121-39-5(Hazardous Substances Data)

Usage

Description

NSC 77154, also known as 9-(2-Propenyl)adenine, is an N-substituted purine derivative that has been identified for its potential applications in various fields. It is characterized by its unique chemical structure, which allows it to interact with other molecules and exhibit specific properties.

Uses

Used in Pharmaceutical Industry:
NSC 77154 is used as a key compound in the preparation of mesityl dihydroisoxazolyl homo-N-nucleosides. These nucleosides are of significant interest due to their potential therapeutic applications, particularly in the development of new drugs for the treatment of various diseases.
In addition to its use in the pharmaceutical industry, NSC 77154 may also have applications in other fields, such as chemical research and material science, where its unique properties can be utilized for the development of novel materials and technologies. However, further research and development are required to fully explore and understand the potential applications of NSC 77154 in these areas.

InChI:InChI=1/C8H9N5/c1-2-3-13-5-12-6-7(9)10-4-11-8(6)13/h2,4-5H,1,3H2,(H2,9,10,11)

Upstream product

• 81546-93-2 9-((RS)-2-phenyl-1,3-dithiolane-4-ylmethyl)adenine 
• 106-95-6 allyl bromide 
• 66224-66-6 adenine 
• 591-87-7 Allyl acetate 
• 191086-68-7 N-(9-Allyl-9H-purin-6-yl)-N-benzoyl-benzamide 
• 87-42-3 6-chloropurine 
• 1258274-91-7 6-chloro-7-(3-methylbut-2-en-1-yl)-7H-purine 
• 520-54-7 7-(3-methylbut-2-en-1-yl)-7H-purin-6-amine 
• 169558-41-2 6-chloro-9-(3-methylbut-2-en-1-yl)-9H-purine 
• 5122-38-3 9-(3-methylbut-2-en-1-yl)-9H-purin-6-amine 
• 1164283-79-7 (E)-6-chloro-9-cinnamyl-9H-purine 
• 1013022-27-9 (E)-9-cinnamyl-9H-purin-6-amine 
• 1446486-34-5 1-(adenin-9-yl)propan-2-yl methanesulfonate 
• 73-24-5 7H-purin-6-ylamine 

Downstream Products

• 191086-68-7 N-(9-Allyl-9H-purin-6-yl)-N-benzoyl-benzamide 
• 191086-74-5 N-{9-[3-(Bis-hydroxymethyl-methyl-silanyl)-propyl]-9H-purin-6-yl}-benzamide 
• 191086-70-1 N-Benzoyl-N-{9-[3-(bis-chloromethyl-methyl-silanyl)-propyl]-9H-purin-6-yl}-benzamide 
• 191086-72-3 Acetic acid {acetoxymethyl-[3-(6-dibenzoylamino-purin-9-yl)-propyl]-methyl-silanyl}-methyl ester 
• 191086-94-9 N-[9-(3-{[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-hydroxymethyl-methyl-silanyl}-propyl)-9H-purin-6-yl]-benzamide 
• 1464851-21-5 (Z)-6-amino-9-(prop-1-en-1-yl)-9H-purine 
• 1446486-33-4 (E)-6-amino-9-(prop-1-en-1-yl)-9H-purine 
• 1547236-41-8 3-allyl-7-nitro-8-phenyl-3H-imidazo[2,1-i]purine 
• 55559-72-3 9-<(2R)-2,3-dihydroxypropyl>adenine 
• 54262-83-8 (S)-9-(2,3-dihydroxypropyl)adenine 

Relevant articles and documents

Customizable and Regioselective One-Pot N?H Functionalization of DNA Nucleobases to Create a Library of Nucleobase Derivatives for Biomedical Applications

DNA is one of the most exciting biomolecules in nature for developing supramolecular biofunctional nanoarchitectures owing to the highly specific and selective interactions between complementary Watson-Crick base pairing. Herein, simple and one-pot synthetic procedures have been implemented for producing a library of DNA nucleobase derivatives endowed with reactive functional groups for bioconjugation and cross-linking strategies with other (bio)molecules. Purine and pyrimidine molecules have been regioselectively N?H functionalized either via N-alkylation, N-allylation, N-propargylation or Michael-type reactions and structurally characterized. The influence of the reaction conditions was assessed and discussed. The in vitro biocompatibility of the native and nucleobase derivatives was evaluated by culturing them with human fibroblasts, revealing their cytocompatibility. The library of nucleobase derivatives holds great promise for being coupled to different biomolecules, including biopolymeric materials, lipids, and peptides, thus potentially leading to modular supramolecular nanobiomaterials for biomedicine.

The Convenient Synthesis of Unsaturated Nucleoside Analogues in Water under Microwave Irradiation

A convenient method for the regioselective synthesis of unsaturated nucleoside analogs in water under microwave irradiation was developed. All pyrimidine and purine nucleoside derivatives were exclusively alkylated at N1 and N9 respectively in good to excellent yields. In addition, this system could tolerate a broad range of functional groups, such as chloro, bromo, iodo, alkyl, amino, and hydroxyl groups. More importantly, the reaction scale could be enlarged to 50 mmol which made this route attractive for industrial application.

A new 9-alkyladenine-cyclic methylglyoxal diadduct activates wt- and F508del-cystic fibrosis transmembrane conductance regulator (CFTR) in vitro and in vivo

Cystic fibrosis transmembrane conductance regulator (CFTR) is the main chloride channel present in the apical membrane of epithelial cells and the F508 deletion (F508del-CFTR) in the CF gene is the most common cystic fibrosis-causing mutation. In the sear