4-Butylbenzonitrile

Base Information

• Chemical Name: 4-Butylbenzonitrile
• CAS No.: 20651-73-4
• Molecular Formula: C11H13N
• Molecular Weight: 159.231
• Hs Code.: 2926909090
• European Community (EC) Number: 623-190-2
• DSSTox Substance ID: DTXSID40174693
• Nikkaji Number: J30.851J
• Wikidata: Q83044799
• Mol file: 20651-73-4.mol

Synonyms:4-Butylbenzonitrile;20651-73-4;Benzonitrile, 4-butyl-;Benzonitrile,4-butyl-;4-n-Butylbenzonitrile;4-butylbenzenecarbonitrile;4-butyl-benzonitrile;4-Butylbenzonitrile #;1-Butyl-4-cyanobenzene;4-(n-butyl)benzonitrile;4-Butylbenzonitrile, 98%;p-tertiary butylbenzyl cyanide;SCHEMBL3753968;DTXSID40174693;MFCD00052345;AKOS015839523;AS-57716;CS-0186971;FT-0617945;D97359;A814768;J-013490

Chemical Property of 4-Butylbenzonitrile

Chemical Property:

• Appearance/Colour: clear colorless liquid
• Vapor Pressure: 0.0114mmHg at 25°C
• Refractive Index: n20/D 1.515(lit.)
• Boiling Point: 261.7 °C at 760 mmHg
• Flash Point: 112.2 °C
• PSA: 23.79000
• Density: 0.96 g/cm³
• LogP: 2.90088
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 159.104799419
• Heavy Atom Count: 12
• Complexity: 157

Purity/Quality:

99% ^*data from raw suppliers

4-Butylbenzonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCCC1=CC=C(C=C1)C#N

Technology Process of 4-Butylbenzonitrile

There total 45 articles about 4-Butylbenzonitrile 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: 97.0%

4-Cyanochlorobenzene (623-03-0) + butylboronic acid (4426-47-5) → 4-butylbenzonitrile (20651-73-4)

Guidance literature:

With potassium phosphate; monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In toluene; at 100 ℃; for 12h;

DOI:10.1021/jo025732j

Reference yield: 95.0%

4-bromobenzenecarbonitrile (623-00-7) + n-butylzinc bromide (92273-73-9) → 4-butylbenzonitrile (20651-73-4)

Guidance literature:

With Ditricyp; bis(η3-allyl-μ-chloropalladium(II)); In tetrahydrofuran; N,N-dimethyl-formamide; at 70 ℃; for 20h;

DOI:10.1016/j.tet.2007.06.072

Reference yield: 94.0%

zinc(II) cyanide (557-21-1) + 4-n-butylchlorobenzene (15499-27-1) → 4-butylbenzonitrile (20651-73-4)

Guidance literature:

With dmap; (dppf)Ni(o-tol)Cl; In acetonitrile; at 60 ℃; for 4h; Reagent/catalyst; Schlenk technique; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.orglett.7b00732

upstream raw materials:

terephthalonitrile

tetrabutylsilane

tetra-n-butyltin(IV)

tetrabutylgermanium

Downstream raw materials:

C₁₉H₂₀F₃NO

C₂₈H₂₂F₆O₂

[4-n-Bu(C₆H₄)C(NSiMe₃)2]Li(TMEDA)

N-(4-n-butylphenyl)benzenamine

Refernces

• 1、 Jones, Andrew C.,Nicholson, William I.,Leitch, Jamie A.,Browne, Duncan L.. "A Ball-Milling-Enabled Cross-Electrophile Coupling". supporting information. p. 6337 - 6341. Retrieved 2021/08/23.
• 2、 Dilauro, Giuseppe,Azzollini, Claudia S.,Vitale, Paola,Salomone, Antonio,Perna, Filippo M.,Capriati, Vito. "Scalable Negishi Coupling between Organozinc Compounds and (Hetero)Aryl Bromides under Aerobic Conditions when using Bulk Water or Deep Eutectic Solvents with no Additional Ligands". supporting information. p. 10632 - 10636. Retrieved 2021/04/09.