4-Methoxy-4-phenylbutanenitrile

Base Information

• Chemical Name: 4-Methoxy-4-phenylbutanenitrile
• CAS No.: 71172-63-9
• Molecular Formula: C11H13 N O
• Molecular Weight: 175.23
• Hs Code.: 2926909090
• European Community (EC) Number: 275-236-2
• NSC Number: 66264
• DSSTox Substance ID: DTXSID501307848
• Nikkaji Number: J308.734D
• Mol file: 71172-63-9.mol

Synonyms:4-methoxy-4-phenylbutanenitrile;71172-63-9;gamma-Methoxybenzenebutyronitrile;gamma-Methoxybenzenebutanenitrile;EINECS 275-236-2;4-Methoxy-4-phenyl-butyronitrile;NSC66264;SCHEMBL2974616;4-methoxy-4-phenylbutyronitrile;DTXSID501307848;MFCD00019887;NSC 66264;NSC-66264;STK502930;AKOS000321470;AKOS016342129;LS-01509;BB 0240837;CS-0315641

Chemical Property of 4-Methoxy-4-phenylbutanenitrile

Chemical Property:

• Boiling Point: 290.6oC at 760 mmHg
• Flash Point: 122.3oC
• PSA: 33.02000
• Density: 1.017g/cm3
• LogP: 2.67788
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 175.099714038
• Heavy Atom Count: 13
• Complexity: 176

Purity/Quality:

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

4-Methoxy-4-phenylbutanenitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(CCC#N)C1=CC=CC=C1

Technology Process of 4-Methoxy-4-phenylbutanenitrile

There total 10 articles about 4-Methoxy-4-phenylbutanenitrile 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: 92.0%

methanol (67-56-1) + 2-phenylcyclobutan-1-one O-(4-(trifluoromethyl)benzoyl) oxime → 4-phenyl-4-methoxybutanenitrile (71172-63-9)

Guidance literature:

methanol; With tetrakis(actonitrile)copper(I) hexafluorophosphate; tert-butyl XPhos; at 20 ℃; for 0.25h; Schlenk technique; Inert atmosphere;

2-phenylcyclobutan-1-one O-(4-(trifluoromethyl)benzoyl) oxime; at 60 ℃; for 5h; Reagent/catalyst; Schlenk technique; Inert atmosphere;

DOI:10.1021/acs.orglett.7b03707

Reference yield: 87.0%

styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + methanol (67-56-1) + cyanomethyl bromide (590-17-0) → 4-phenyl-4-methoxybutanenitrile (71172-63-9)

Guidance literature:

With tris[2-phenylpyridinato-C₂,N]iridium(III); sodium hydrogencarbonate; at 20 ℃; for 24h; Inert atmosphere; Irradiation;

DOI:10.1002/adsc.201400548

Reference yield: 56.0%

benzaldehyde dimethyl acetal (1125-88-8) + acrylonitrile (107-13-1,25014-41-9) → 4-phenyl-4-methoxybutanenitrile (71172-63-9)

Guidance literature:

With manganese; tetrachloro(N,N,N',N'-tetramethylethane-1,2-diamine)titanium(IV); triethylamine hydrochloride; In tetrahydrofuran; at 70 ℃; for 20h; Time; Solvent; Reagent/catalyst; Inert atmosphere;

DOI:10.1246/bcsj.20200364

upstream raw materials:

styrene

methanol

cyanomethyl bromide

2-phenylcyclobutanone

Downstream raw materials:

cis-bis(4-methoxy-4-phenylbutyronitrile)dichloroplatinum (II)

Refernces

• 1、 Suga, Takuya,Nakamura, Masaharu,Takada, Ryusei,Ukaji, Yutaka. "Conjugate addition of acetal-derived benzyl radicals generated from low-valent titanium-mediated CO bond cleavage". supporting information. p. 1258 - 1260. Retrieved 2021/05/17.
• 2、 Ai, Wenying,Liu, Yaqian,Wang, Qian,Lu, Zhonglin,Liu, Qiang. "Cu-Catalyzed Redox-Neutral Ring Cleavage of Cycloketone O-Acyl Oximes: Chemodivergent Access to Distal Oxygenated Nitriles". supporting information. p. 409 - 412. Retrieved 2018/01/27.