(S)-4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile

Base Information

• Chemical Name: (S)-4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile
• CAS No.: 488787-59-3
• Molecular Formula: C20H23FN2O2
• Molecular Weight: 342.413
• Hs Code.: 2926909090
• UNII: F848JLN2QI
• DSSTox Substance ID: DTXSID80197624
• Nikkaji Number: J2.015.543D
• Wikidata: Q27277795
• Mol file: 488787-59-3.mol

Synonyms:488787-59-3;(S)-4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile;(S)-Citadiol;Citadiol, (S)-;4-[(1S)-4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl]-3-(hydroxymethyl)benzonitrile;UNII-F848JLN2QI;F848JLN2QI;(-)-4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile;(S)-4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxy-1-butyl)-3-(hydroxymethyl)benzonitrile;Benzonitrile, 4-((1S)-4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)-;C20H23FN2O2;(-)-4-[4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl]-3-(hydroxymethyl)benzonitrile;SCHEMBL907571;DTXSID80197624;GNULRNVWXYXBQY-FQEVSTJZSA-N;AKOS015998934;SB44350;DS-18489;CS-0151290;D82411;Q27277795;4-[(S)-1-Hydroxy-1-(4-fluorophenyl)-4-(dimethylamino)butyl]-3-(hydroxymethyl)benzonitrile;(s)-(-)-4-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxy-1-butyl]-3-(hydroxymethyl)-benzonitrile;(S)-(-)-4-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxy-1-butyl]-3-(hydroxymethyl)benzonitrile

Chemical Property of (S)-4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile

Chemical Property:

• Boiling Point: 537.2 °C at 760 mmHg
• PKA: 12.97±0.29(Predicted)
• Flash Point: 278.7 °C
• PSA: 67.49000
• Density: 1.22 g/cm³
• LogP: 2.76738
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 342.17435614
• Heavy Atom Count: 25
• Complexity: 456

Purity/Quality:

99% ^*data from raw suppliers

(S)-4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)CCCC(C1=CC=C(C=C1)F)(C2=C(C=C(C=C2)C#N)CO)O
• Isomeric SMILES: CN(C)CCC[C@](C1=CC=C(C=C1)F)(C2=C(C=C(C=C2)C#N)CO)O

Technology Process of (S)-4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile

There total 38 articles about (S)-4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile 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: 100.0%

(1S)-4-[4-(dimethylamino)-1-(4'-fluorophenyl)-1-hydroxybutyl]-3-(hydroxymethyl)benzonitrile hemi-(+)-di-(p-toluoyl) tartaric acid salt (128173-53-5,912452-31-4) → (S)-(-)-4-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxy-1-butyl]-3-(hydroxymethyl)benzonitrile (488787-59-3,219861-18-4,481047-48-7)

Guidance literature:

With sodium hydroxide; In diethyl ether; water; at 25 ℃; for 0.5h;

Reference yield: 96.4%

C17H26N2O2Si + 4-flourophenylmagnesium bromide (352-13-6) → (S)-(-)-4-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxy-1-butyl]-3-(hydroxymethyl)benzonitrile (488787-59-3,219861-18-4,481047-48-7)

Guidance literature:

4-flourophenylmagnesium bromide; With C₄₅H₅₅FeNP₂; copper dichloride; In toluene; at 60 ℃; for 1h; Inert atmosphere; Large scale;

C₁₇H₂₆N₂O₂Si; In toluene; at 60 ℃; for 12h; Reagent/catalyst; Temperature; Solvent; Inert atmosphere; Large scale;

Reference yield: 70.0%

4-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl]-3-(hydroxymethyl)benzonitrile (103146-25-4,219861-18-4,481047-48-7) → (S)-(-)-4-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxy-1-butyl]-3-(hydroxymethyl)benzonitrile (488787-59-3,219861-18-4,481047-48-7)

Guidance literature:

4-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl]-3-(hydroxymethyl)benzonitrile; With D-di-4-methylbenzoyl tartaric acid; In isopropyl alcohol; at 20 ℃; for 12h; Resolution of racemate;

With sodium hydroxide; In water; toluene;

upstream raw materials:

vinyl acetate

4-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl]-3-(hydroxymethyl)benzonitrile

(+/-)-3-(acetoxymethyl)-4-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl]benzonitrile

vinyl n-butyrate

Downstream raw materials:

1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile

(S)-(-)-4-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxy-1-butyl]-3-(2-nitro-4-chlorophenoxymethyl)benzonitrile hydrochloride

escitalopram oxalate

succinic acid mono-{5-cyano-2-[(S)-4-dimethylamino-1-(4-fluorophenyl)-1-hydroxybutyl]-benzyl} ester

Refernces

• 1、 -. "PRODUCTION METHOD OF (1S)-4-[4-(DIMETHYLAMINO)-1-(4'-FLUOROPHENYL)-1-HYDROXYBUTYL]-3-(HYDROXYMETHYL)-BENZONITRILE HEMI(+)-DI-(p-TOLUOYL) TARTRATE, AND PRODUCTION METHOD OF (1S)-1-[3-(DIMETHYLAMINO)PROPYL]-1-(4-FLUOROPHENYL)-1,3-DIHYDROISOBENZOFURAN-5-CARBONITRILE AND SALT THEREOF USING THE TARTRATE". . . Retrieved 2018/05/03.
• 2、 -. "PROCESS FOR PRODUCING (1S)-4-[4-(DIMETHYLAMINO)-1-(4'-FLUOROPHENYL)-1-HYDROXYBUTYL]-3-(HYDROXYMETHYL)-BENZONITRILE HEMI(+)-DI-(p-TOLUOYL) TARTARIC ACID SALT, AND PROCESS FOR PRODUCING (1S)-1-[3-(DIMETHYLAMINO)PROPYL]-1-(4-FLUOROPHENYL)-1,3-DIHYDRO-ISOBENZOFURAN-5-CARBO-NITRILE AND SALT THEREOF USING SAID TARTARIC ACID SALT". . . Retrieved 2018/07/28.