alpha-[4-[2-(dimethylamino)ethoxy]phenyl]-beta-ethyl-alpha-phenylphenethyl alcohol

Base Information

• Chemical Name: alpha-[4-[2-(dimethylamino)ethoxy]phenyl]-beta-ethyl-alpha-phenylphenethyl alcohol
• CAS No.: 748-97-0
• Molecular Formula: C26H31 N O2
• Molecular Weight: 389.538
• European Community (EC) Number: 212-023-5
• UNII: ZF9GQ0WZ9X
• DSSTox Substance ID: DTXSID70862399
• Nikkaji Number: J193.112A
• Wikidata: Q27295435
• Mol file: 748-97-0.mol

Synonyms:1-Butanol,1-[p-[2-(dimethylamino)ethoxy]phenyl]-1,2-diphenyl- (7CI,8CI); (?à)-1,2-Diphenyl-1-[4-[2-(dimethylamino)ethoxy]phenyl]butan-1-ol

Chemical Property of alpha-[4-[2-(dimethylamino)ethoxy]phenyl]-beta-ethyl-alpha-phenylphenethyl alcohol

Chemical Property:

• Vapor Pressure: 5.43E-11mmHg at 25°C
• Melting Point: 120-121℃
• Boiling Point: 504.3°C at 760 mmHg
• PKA: 13.31±0.29(Predicted)
• Flash Point: 258.8°C
• PSA: 32.70000
• Density: 1.085g/cm³
• LogP: 5.05670
• XLogP3: 5.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 9
• Exact Mass: 389.235479232
• Heavy Atom Count: 29
• Complexity: 448

Purity/Quality:

99.9% ^*data from raw suppliers

(±)-1,2-Diphenyl-1-[4-[2-(dimethylamino)ethoxy]phenyl]butan-1-ol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C1=CC=CC=C1)C(C2=CC=CC=C2)(C3=CC=C(C=C3)OCCN(C)C)O
• Uses: (±)-1,2-Diphenyl-1-[4-[2-(dimethylamino)ethoxy]phenyl]butan-1-ol is an impurity of Tamoxifen (T006000); a selective estrogen response modifier (SERM), protein kinase C inhibitor and anti-angiogenetic factor.

Technology Process of alpha-[4-[2-(dimethylamino)ethoxy]phenyl]-beta-ethyl-alpha-phenylphenethyl alcohol

There total 13 articles about alpha-[4-[2-(dimethylamino)ethoxy]phenyl]-beta-ethyl-alpha-phenylphenethyl alcohol 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: 86.0%

1-[4-[2-(N,N-dimethylamino)ethoxy]phenyl]-2-phenyl-1-butanone (68047-07-4) + phenylmagnesium bromide (100-58-3) → 1-(4-(2-(dimethylamino)ethoxy)phenyl)-1,2-diphenylbutan-1-ol (748-97-0,82407-94-1)

Guidance literature:

In tetrahydrofuran; at -20 - 60 ℃; for 25h; Inert atmosphere; Schlenk technique;

DOI:10.1002/chem.202103851

Reference yield: 72.0%

[2-(4-bromophenoxy)ethyl]dimethylamine (2474-07-9) + 1,2-diphenyl-butan-1-one (16282-16-9) → 1-(4-(2-(dimethylamino)ethoxy)phenyl)-1,2-diphenylbutan-1-ol (748-97-0,82407-94-1)

Guidance literature:

[2-(4-bromophenoxy)ethyl]dimethylamine; With n-butyllithium; 4-methyltetrahydropyran; In hexane; at -78 ℃; for 1h; Inert atmosphere; Green chemistry;

1,2-diphenyl-butan-1-one; In hexane; at -78 - 0 ℃; for 1.5h; Inert atmosphere; Green chemistry;

DOI:10.1002/asia.201901169

Reference yield:

(4-(2-(dimethylamino)ethoxy)phenyl)(phenyl)methanone (51777-15-2) + (1-Chloro-propyl)-benzene (934-11-2) → 1-(4-(2-(dimethylamino)ethoxy)phenyl)-1,2-diphenylbutan-1-ol (748-97-0,82407-94-1)

Guidance literature:

With 4,4'-di-tert-butylbiphenyl; lithium; In tetrahydrofuran; at -78 ℃; for 1h;

DOI:10.1016/S0040-4020(03)00428-9

upstream raw materials:

bromobenzene

1-[4-[2-(N,N-dimethylamino)ethoxy]phenyl]-2-phenyl-1-butanone

phenylpropane

(4-(2-(dimethylamino)ethoxy)phenyl)(phenyl)methanone

Downstream raw materials:

tamoxifen

tamoxifen

(E)-tamoxifen

tamoxifen citrate

Refernces

• 1、 Kobayashi, Shoji,Tamura, Tomoki,Yoshimoto, Saki,Kawakami, Takashi,Masuyama, Araki. "4-Methyltetrahydropyran (4-MeTHP): Application as an Organic Reaction Solvent". . p. 3921 - 3937. Retrieved 2019/11/11.
• 2、 Thurner, Angelika,Agai, Bela,Faigl, Ferenc. "Regioselective Metallation of Propylbenzene with Superbase: A Convenient Route to Stilbene Derivatives". . p. 158 - 159. Retrieved 2007/10/03.