1-Butyltheobromine

Base Information

• Chemical Name: 1-Butyltheobromine
• CAS No.: 1143-30-2
• Molecular Formula: C11H16 N4 O2
• Molecular Weight: 236.274
• Hs Code.: 2933990090
• NSC Number: 3111
• UNII: AMU665LKFR
• DSSTox Substance ID: DTXSID60150691
• Nikkaji Number: J21.567H
• Wikidata: Q27274005
• Mol file: 1143-30-2.mol

Synonyms:1-Butyltheobromine;1-n-Butyl-3,7-dimethylxanthine;1143-30-2;Theobromine, 1-butyl-;1-butyl-3,7-dimethylpurine-2,6-dione;NSC 3111;UNII-AMU665LKFR;AMU665LKFR;BRN 0026680;1H-Purine-2,6-dione, 1-butyl-3,7-dihydro-3,7-dimethyl-;NSC-3111;4-26-00-02348 (Beilstein Handbook Reference);n-Butyltheobromin;NSC3111;SCHEMBL516018;BDBM82046;DTXSID60150691;CAS_70835;NSC_70835;LS-149359;WLN: T56 BN DN FNVNVJ B1 F1 H4;1H-Purine-2, 1-butyl-3,7-dihydro-3,7-dimethyl-;Q27274005

Chemical Property of 1-Butyltheobromine

Chemical Property:

• Vapor Pressure: 9.41E-08mmHg at 25°C
• Melting Point: 108°C
• Refractive Index: 1.6081 (estimate)
• Boiling Point: 434.5°C at 760 mmHg
• Flash Point: 216.6°C
• PSA: 61.82000
• Density: 1.29g/cm³
• LogP: 0.23380
• Water Solubility.: 5.6g/L(30 oC)
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 236.12732577
• Heavy Atom Count: 17
• Complexity: 333

Purity/Quality:

98%,99%, ^*data from raw suppliers

1-N-BUTYL-3,7-DIMETHYLXANTHINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCN1C(=O)C2=C(N=CN2C)N(C1=O)C

Technology Process of 1-Butyltheobromine

There total 6 articles about 1-Butyltheobromine 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: 84.0%

theobromine / (83-67-0) → 1-n-Butyl-3,7-dimethylxanthine (1143-30-2)

Guidance literature:

theobromine /; With sodium hydride; In dimethyl sulfoxide; at 60 ℃; for 0.333333h; Inert atmosphere;

1-butylhalide; In dimethyl sulfoxide; at 60 ℃; Inert atmosphere;

DOI:10.1021/ja200551y

Reference yield: 4.0%

isoalantolactone (470-17-7) + 1-(n-butyl)-8-bromotheobromine → Asterolide (73069-14-4) + 1-n-Butyl-3,7-dimethylxanthine (1143-30-2) + 1-butyl-3,7-dimethyl-8-((E)-((3aR,4aS,8aR,9aR)-8a-methyl-5-methylene-2-oxodecahydronaphtho[2,3-b]furan-3(2H)ylidene)methyl)-1H-purine-2,6(3H,7H)dione + 1-butyl-3,7-dimethyl-8-(((4aS,8aR,9aS)-8a-methyl-5-methylene-2-oxo-2,4,4a,5,6,7,8,8a,9,9a-decahydronaphtho[2,3-b]furan-3-yl)methyl)-1H-purine-2,6(3H,7H)dione + 8,8'-bis-(1-butyl-3,7-dimethyl-1H-purine-2,6(3H,7H)-dione)

Guidance literature:

With tetrabutylammomium bromide; palladium diacetate; triethylamine; tris-(o-tolyl)phosphine; In N,N-dimethyl-formamide; at 140 ℃; for 40h; Inert atmosphere; Molecular sieve; Sealed tube;

DOI:10.1016/j.tet.2017.03.016

Reference yield:

C19H25N7O2 → 1-n-Butyl-3,7-dimethylxanthine (1143-30-2)

Guidance literature:

With bis(1,5-cyclooctadiene)iridium(I) tetrakis[3,5-bis(trifluoromethyl)phenyl]borate; 1,1-bis-(diphenylphosphino)ethene; buta-1,3-diene; In 1,4-dioxane; toluene; at 160 ℃; for 72h; Molecular sieve; Glovebox; Sealed tube;

DOI:10.1038/s41586-019-0926-8

upstream raw materials:

1-bromo-butane

theobromine /

1-iodo-butane

isoalantolactone

Downstream raw materials:

1-butyl-8-(4-methoxyphenyl)-3,7-dimethyl-1H-purine-2,6(3H,7H)-dione

Refernces

• 1、 Xu, Yan,Qi, Xiaotian,Zheng, Pengfei,Berti, Carlo C.,Liu, Peng,Dong, Guangbin. "Deacylative transformations of ketones via aromatization-promoted C–C bond activation". . p. 373 - 378. Retrieved 2019/05/22.
• 2、 Madyastha,Sridhar. "Highly efficient C-8 oxidation of substituted xanthines with substitution at the 1-, 3-, and 7- Positions using biocatalysts". . p. 677 - 680. Retrieved 2007/10/03.