Stannane, tributyl(4-nitrophenyl)-

Base Information

• Chemical Name: Stannane, tributyl(4-nitrophenyl)-
• CAS No.: 79048-32-1
• Molecular Formula: C18H31NO2Sn
• Molecular Weight: 412.16
• DSSTox Substance ID: DTXSID20451095
• Mol file: 79048-32-1.mol

Synonyms:79048-32-1;Stannane, tributyl(4-nitrophenyl)-;tributyl(4-nitrophenyl)tin;p-nitrophenyltributylstannane;SCHEMBL2922658;DTXSID20451095;SGYDQFRDDMXSMY-UHFFFAOYSA-N;tributyl-(4-nitro-phenyl)-stannane;TRIBUTYL(4-NITROPHENYL)STANNANE;EN300-7469071

Chemical Property of Stannane, tributyl(4-nitrophenyl)-

Chemical Property:

• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 10
• Exact Mass: 413.137682
• Heavy Atom Count: 22
• Complexity: 287

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCC[Sn](CCCC)(CCCC)C1=CC=C(C=C1)[N+](=O)[O-]

Technology Process of Stannane, tributyl(4-nitrophenyl)-

There total 7 articles about Stannane, tributyl(4-nitrophenyl)- 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: 90.0%

tri-n-butyl-tin hydride (688-73-3) + 4-chlorobenzonitrile (100-00-5) → 4-(tri-n-butylstannyl)nitrobenzene (79048-32-1)

Guidance literature:

With potassium acetate; In further solvent(s); addn. of arene and tin compd. to a mixt. of palladium catalyst and potassium acetate in 1-methyl-2-pyrrolidone, stirring at 50°C for 16 h; addn. of benzene, washing with water, evapn.;

DOI:10.1021/ja026975w

Reference yield: 90.0%

bis(tri-n-butyltin) (813-19-4) + para-nitrophenyl bromide (586-78-7) → 4-(tri-n-butylstannyl)nitrobenzene (79048-32-1)

Guidance literature:

With potassium fluoride; tetraethylene glycol monododecyl ether; tetrabutyl-ammonium chloride; C₃₄H₃₄NO₃PPdS; In tetrahydrofuran; water; at 65 ℃; for 6h; Inert atmosphere;

DOI:10.1002/anie.202014141

Reference yield: 82.0%

p-nitrobenzene iodide (636-98-6) + bis(tri-n-butyltin) (813-19-4) → tributyltin iodide (7342-47-4) + 4-(tri-n-butylstannyl)nitrobenzene (79048-32-1)

Guidance literature:

dichloro bis(acetonitrile) palladium(II); In N,N-dimethyl-formamide; 20°C, molar ratio distannane/halide 1.2:1, 150 min;

DOI:10.1007/BF01141722

upstream raw materials:

bis(tri-n-butyltin)

para-nitrophenyl bromide

tri-n-butyl-tin hydride

4-chlorobenzonitrile

Downstream raw materials:

1-(4-nitrophenyl)propan-2-one

4,4'-dinitrobiphenyl

(4S,4aR,5S,5aR,6R,12aS)-9-Amino-4-dimethylamino-3,5,10,12,12a-pentahydroxy-6-methyl-8-(4-nitro-phenyl)-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-naphthacene-2-carboxylic acid amide

4-[¹²⁵I]iodonitrobenzene

Refernces

• 1、 Gribanov, Pavel S.,Golenko, Yulia D.,Topchiy, Maxim A.,Minaeva, Lidiya I.,Asachenko, Andrey F.,Nechaev, Mikhail S.. "Stannylation of Aryl Halides, Stille Cross-Coupling, and One-Pot, Two-Step Stannylation/Stille Cross-Coupling Reactions under Solvent-Free Conditions". supporting information. p. 120 - 125. Retrieved 2018/01/17.
• 2、 Bumagin, N. A.,Gulevich, Yu. V.,Beletskaya, I. P.. "SYNTHESIS OF HEXAALKYL(ARYL)DISTANNANES AND THEIR REACTION WITH ORGANIC HALIDES UNDER CONDITIONS OF CATALYSIS BY PALLADIUM COMPLEXES". . p. 1044 - 1049. Retrieved 2007/10/02.