N-(3-Methylbut-2-EN-1-YL)-9H-purin-6-amine

Base Information

• Chemical Name: N-(3-Methylbut-2-EN-1-YL)-9H-purin-6-amine
• CAS No.: 2365-40-4
• Deprecated CAS: 13255-47-5,5122-37-2
• Molecular Formula: C10H13N5
• Molecular Weight: 203.247
• Hs Code.: 2934993000
• European Community (EC) Number: 812-988-8
• NSC Number: 106958
• UNII: V500BB256Z
• DSSTox Substance ID: DTXSID10178325
• Nikkaji Number: J120.788A
• Wikidata: Q569031
• Metabolomics Workbench ID: 49874
• ChEMBL ID: CHEMBL476189
• Mol file: 2365-40-4.mol

Synonyms:6-(3-methyl-2-butenylamino)purine;dimethylallyladenine;i6Ade;IPADE;isopentenyladenine;N(6)-(delta(2)-isopentenyl)adenine

Chemical Property of N-(3-Methylbut-2-EN-1-YL)-9H-purin-6-amine

Chemical Property:

• Vapor Pressure: 0.000352mmHg at 25°C
• Melting Point: 218-220 °C
• Refractive Index: 1.659
• Boiling Point: 477.144 °C at 760 mmHg
• PKA: 9.36±0.20(Predicted)
• Flash Point: 242.368 °C
• PSA: 66.49000
• Density: 1.267 g/cm³
• LogP: 1.80400
• Storage Temp.: −20°C
• Solubility.: DMF (Slightly), Methanol (Slightly)
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 203.11709544
• Heavy Atom Count: 15
• Complexity: 236

Purity/Quality:

99% ^*data from raw suppliers

N6-(2-Isopentenyl)adenine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Nucleic Acids and Derivatives
• Canonical SMILES: CC(=CCNC1=NC=NC2=C1NC=N2)C
• Uses: N6-(2-Isopentenyl)adenine can be used in biological study for cytokinins stimulated expression of stress-related proteins and transcripts in Arabidopsis thaliana with isopentenyltransferase overexpression. 6-(γ,γ-Dimethylallylamino)purine (2iP) is a bacteria-derived riboside cytokinin used to grow plant tissues such as tobacco and soybean callus. 2iP is a precursor of the cytokinin Zeatin. 2iP has been used in Schenk and Hildebrandt medium to support in vitro propagation of microshoot cultures from shoot tips of Genista plants.
• Description: A purine alkaloid, this base was first isolated from the leaves of Gleditsia triacanthus L., and subsequently discovered in Chidlowia sanguinea and Holar_x0002_rhena floribunda (G. Don.) Dur. et Schinz. The free alkaloid forms colourless crystals and yields crystalline salts and derivatives, e.g. the hydrochloride, m.p. 218-9°C; hydrobromide, m.p. 215-6°C; sulphate, two salts are formed with m.p. 175-6°C and 216-7°C respectively depending upon the amount of acid used in their preparation; picrate, m.p. 246-7°C (dec.); picrolonate, m.p. 229-231 0 C; methiodide, m.p. 227-9°C and the N-benzyl derivative, m.p. 150°C. Oxidation of the alkaloid with KMn04 gives 7-(2:3-dihydroxy-3-methylbutyl)-6-aminopurine which, on periodate oxidation, furnishes 7-(formylmethyl)- 6-aminopurine and Me2CO. Heating the base with Ba(OHh gives one mole each of NH3, C02 and 4-N-(r:r-dimethylallyl)-N-amino-imidazole-5-carboxamide.

Technology Process of N-(3-Methylbut-2-EN-1-YL)-9H-purin-6-amine

There total 16 articles about N-(3-Methylbut-2-EN-1-YL)-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: 96.6%

3,3-dimethylallylamine (13822-06-5,108963-90-2) + 6-chloropurine (87-42-3) → N6-(2-isopentenyl)adenine (2365-40-4)

Guidance literature:

With triethylamine; In ethanol; for 5h; Reflux;

Reference yield: 79.0%

6-N-(2-isopentenyl)adenosine (7724-76-7,33156-15-9) → N6-(2-isopentenyl)adenine (2365-40-4)

Guidance literature:

With disodium hydrogen arsenate heptahydrate; recombinant E_. coli purine nucleoside phosphorylase; In aq. buffer; at 50 ℃; for 16h; pH=7.5; Enzymatic reaction;

DOI:10.1039/c8ob00223a

Reference yield: 73.0%

(2-chloro-7(9)H-purin-6-yl)-(3-methyl-but-2-enyl)-amine (29911-54-4) → N6-(2-isopentenyl)adenine (2365-40-4)

Guidance literature:

(2-chloro-7⁽⁹⁾H-purin-6-yl)-(3-methyl-but-2-enyl)-amine; With bis(cyclopentadienyl)titanium dichloride; isopropylmagnesium bromide; In tetrahydrofuran; for 24h; Reflux;

With water; at 0 ℃;

DOI:10.1021/bi4000832

upstream raw materials:

trans-zeatin O-β-D-glucopyranoside

6-N-2',3',5'-tri-O-tetraacetyladenosine

N⁶-acetyl-N⁶-isopentenyl-2',3',5'-tri-O-acetyladenosine

6-N-(2-isopentenyl)adenosine

Downstream raw materials:

OsO₂(O₂C₅H₉NH)C₅N₄H₃(C₅H₄N)2

[ZnCl₃(N₆-isopentenyladeninium⁽¹⁺⁾)]*water

[5-amino-4-(4,4-dimethyl-3,4,5,6-tetrahydropyrimidin-2-yl)imidazolium⁽²⁺⁾][ZnCl₄]

[5-amino-4-(4,4-dimethyl-3,4,5,6-tetrahydropyrimidin-2-yl)imidazolium⁽²⁺⁾][Cu(II)Cl₄]

Refernces

• 1、 Leonard et al.. "-". . p. 709,714. Retrieved 1966.
• 2、 Oslovsky, Vladimir E.,Solyev, Pavel N.,Polyakov, Konstantin M.,Alexeev, Cyril S.,Mikhailov, Sergey N.. "Chemoenzymatic synthesis of cytokinins from nucleosides: Ribose as a blocking group". . p. 2156 - 2163. Retrieved 2018/03/26.
• 3、 Tararov, Vitali I.,Tijsma, Aloys,Kolyachkina, Svetlana V.,Oslovsky, Vladimir E.,Neyts, Johan,Drenichev, Mikhail S.,Leyssen, Pieter,Mikhailov, Sergey N.. "Chemical modification of the plant isoprenoid cytokinin N 6-isopentenyladenosine yields a selective inhibitor of human enterovirus 71 replication". . p. 406 - 413. Retrieved 2015/02/19.