Benzenamine, N-methyl-N-(3-methyl-2-butenyl)-

Base Information

• Chemical Name: Benzenamine, N-methyl-N-(3-methyl-2-butenyl)-
• CAS No.: 10229-37-5
• Molecular Formula: C12H17N
• Molecular Weight: 175.274
• DSSTox Substance ID: DTXSID90440996
• Nikkaji Number: J904.270I
• Mol file: 10229-37-5.mol

Synonyms:10229-37-5;N-Prenyl-N-methylaniline;Benzenamine, N-methyl-N-(3-methyl-2-butenyl)-;SCHEMBL6543119;DTXSID90440996;AKOS024263115

Chemical Property of Benzenamine, N-methyl-N-(3-methyl-2-butenyl)-

Chemical Property:

• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 175.136099547
• Heavy Atom Count: 13
• Complexity: 162

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCN(C)C1=CC=CC=C1)C

Technology Process of Benzenamine, N-methyl-N-(3-methyl-2-butenyl)-

There total 19 articles about Benzenamine, N-methyl-N-(3-methyl-2-butenyl)- 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: 95.0%

3,3-dimethyl acrylaldehyde (107-86-8) + N-methylaniline hydrochloride (2739-12-0) → N-(3-methylbut-2-enyl)-N-methylaniline (10229-37-5)

Guidance literature:

3,3-dimethyl acrylaldehyde; N-methylaniline hydrochloride; In methanol; at 20 ℃; for 1h;

With triethylsilane; indium(III) chloride; In methanol; at 20 ℃; for 24h;

DOI:10.1021/jo8016082

Reference yield: 90.0%

2-methyl-3-buten-2-ol (115-18-4) + N-methylaniline (100-61-8) → N-(3-methylbut-2-enyl)-N-methylaniline (10229-37-5)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; bis(η3-allyl-μ-chloropalladium(II)); Methyl formate; polyoxyethanyl-α-tocopheryl sebacate; potassium carbonate; In water; at 20 ℃; for 20h; regioselective reaction; Inert atmosphere;

DOI:10.1021/ol900235s

Reference yield: 87.0%

3-methyl-2-buten-1-ol (556-82-1) + N-methylaniline (100-61-8) → N-(3-methylbut-2-enyl)-N-methylaniline (10229-37-5)

Guidance literature:

With boric acid; In dichloromethane; for 12h; regioselective reaction; Reflux; Inert atmosphere;

DOI:10.1016/j.tetlet.2010.02.017

upstream raw materials:

N-methylaniline

3,3-dimethyl-allyl chloride

3,3-dimethylallyl diphenyl phosphate

prenyl diisopropyl phosphate

Downstream raw materials:

N-methyl-N-phenylformamide

(7-(3-(dimethylamino)phenylthio)-1,4,4-trimethyl-1,2,3,4-tetrahydroquinolin-6-yl)(piperidin-1-yl)methanone

C₁₂H₁₇NO

O-[2-(2-methylbut-3-enyl)]-N-methyl-N-phenylhydroxylamine

Refernces

• 1、 Carden, Robert G.,Duncan, Alethea N.,Harris, Robert J.,Nakafuku, Kohki,Timmerman, Jacob C.,Widenhoefer, Ross A.. "Kinetics and Mechanism of the Gold-Catalyzed Hydroamination of 1,1-Dimethylallene with N-Methylaniline". supporting information. p. 10377 - 10386. Retrieved 2021/06/08.
• 2、 Gans?uer, Andreas,Hildebrandt, Sven,Michelmann, Antonius,Dahmen, Tobias,Von laufenberg, Daniel,Kube, Christian,Fianu, Godfred D.,Flowers, Robert A.. "Cationic Titanocene(III) Complexes for Catalysis in Single-Electron Steps". supporting information. p. 7003 - 7006. Retrieved 2015/06/08.