9-Allyl-9H-purin-6-amine

Base Information

• Chemical Name: 9-Allyl-9H-purin-6-amine
• CAS No.: 4121-39-5
• Molecular Formula: C8H9N5
• Molecular Weight: 175.193
• Hs Code.: 2933990090
• NSC Number: 77154
• UNII: 79SW4GB7Y4
• DSSTox Substance ID: DTXSID00194135
• Nikkaji Number: J1.276.777C
• Mol file: 4121-39-5.mol

Synonyms:9-ALLYL-9H-PURIN-6-AMINE;4121-39-5;9-prop-2-enylpurin-6-amine;9H-Purin-6-amine, 9-(2-propenyl)-;9-(2-Propenyl)adenine;NSC 77154;79SW4GB7Y4;NSC-77154;9-Allyladenin;9-(allyl)adenine;NSC77154;9-(2-propen-1-yl)-9H-Purin-6-amine;9H-Purin-6-amine,9-(2-propen-1-yl)-;UNII-79SW4GB7Y4;SCHEMBL1798270;DTXSID00194135;AMY22218;AKOS006324816;CS-0164422;A873108;9H-PURIN-6-AMINE, 9-(2-PROPEN-1-YL)-;9-allyl-9H-purin-6-amine? (Tenofovir Impurity pound(c)

Chemical Property of 9-Allyl-9H-purin-6-amine

Chemical Property:

• Vapor Pressure: 3.06E-06mmHg at 25°C
• Refractive Index: 1.714
• Boiling Point: 388.4 °C at 760 mmHg
• Flash Point: 188.7 °C
• PSA: 69.62000
• Density: 1.39 g/cm³
• LogP: 1.17570
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Ethanol (Slightly), Methanol (Slightly)
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 175.08579531
• Heavy Atom Count: 13
• Complexity: 195

Purity/Quality:

99% ^*data from raw suppliers

9-(2-Propenyl)adenine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=CCN1C=NC2=C(N=CN=C21)N
• Uses: 9-(2-Propenyl)adenine is an N-substituted purine used in the preparation of mesityl dihydroisoxazolyl homo-N-nucleosides.

Technology Process of 9-Allyl-9H-purin-6-amine

There total 21 articles about 9-Allyl-9H-purin-6-amine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 76.0%

allyl bromide (106-95-6) + adenine (66224-66-6,66224-67-7,66224-68-8,66224-69-9,134434-48-3,134434-49-4,134454-76-5,134461-75-9) → 9-allyl-9H-adenine (4121-39-5)

Guidance literature:

With sodium hydroxide; In water; at 100 ℃; for 0.166667h; regioselective reaction; Microwave irradiation;

DOI:10.1080/15257770.2015.1114129

Reference yield: 37.0%

mesityl nitrile oxide + N-(9-Allyl-9H-purin-6-yl)-N-benzoyl-benzamide (191086-68-7) → 9-[(3-mesityl-4,5-dihydroisoxazol-5-yl)methyl]-9H-purin-6-amine (1201794-61-7) + N-{9-[(3-mesityl-4,5-dihydroisoxazol-5-yl)methyl]-9H-purin-6-yl}benzamide (1201794-60-6) + 9-allyl-6-N-benzoyladenine (27507-29-5) + 9-allyl-9H-adenine (4121-39-5)

Guidance literature:

In toluene; for 168h; Reflux;

DOI:10.1016/j.bmcl.2009.09.040

Reference yield: 27.0%

allyl bromide (106-95-6) + adenine (66224-66-6,66224-67-7,66224-68-8,66224-69-9,134434-48-3,134434-49-4,134454-76-5,134461-75-9) → 9-allyl-6-(N-allylamino)purine (112615-67-5) + 9-allyl-6-N-diallylaminopurine (112615-68-6) + 9-allyl-9H-adenine (4121-39-5) + 3-Allyladenin (13532-34-8)

Guidance literature:

With potassium hydroxide; Aliquat 336; In neat (no solvent); for 3h; Ambient temperature;

DOI:10.1016/S0040-4020(01)86791-0

upstream raw materials:

9-((RS)-2-phenyl-1,3-dithiolane-4-ylmethyl)adenine

allyl bromide

adenine

Allyl acetate

Downstream raw materials:

N-(9-Allyl-9H-purin-6-yl)-N-benzoyl-benzamide

N-{9-[3-(Bis-hydroxymethyl-methyl-silanyl)-propyl]-9H-purin-6-yl}-benzamide

N-Benzoyl-N-{9-[3-(bis-chloromethyl-methyl-silanyl)-propyl]-9H-purin-6-yl}-benzamide

Acetic acid {acetoxymethyl-[3-(6-dibenzoylamino-purin-9-yl)-propyl]-methyl-silanyl}-methyl ester

Refernces

• 1、 Qin, Tao,Li, Jian-Ping,Xie, Ming-Sheng,Qu, Gui-Rong,Guo, Hai-Ming. "Synthesis of Chiral Acyclic Nucleosides by Sharpless Asymmetric Dihydroxylation: Access to Cidofovir and Buciclovir". . p. 15512 - 15523. Retrieved 2019/01/04.
• 2、 Boucherle, Benjamin,Bertrand, Johanna,Maurin, Bruno,Renard, Brice-Lo?c,Fortuné, Antoine,Tremblier, Brice,Becq, Frédéric,Norez, Caroline,Décout, Jean-Luc. "A new 9-alkyladenine-cyclic methylglyoxal diadduct activates wt- and F508del-cystic fibrosis transmembrane conductance regulator (CFTR) in vitro and in vivo". . p. 455 - 465. Retrieved 2014/07/21.