(3R)-3-(4-Trifluoromethyl-phenylamino)-pentanenitrile

Base Information

• Chemical Name: (3R)-3-(4-Trifluoromethyl-phenylamino)-pentanenitrile
• CAS No.: 474645-91-5
• Molecular Formula: C12H13F3N2
• Molecular Weight: 242.244
• European Community (EC) Number: 610-351-7
• DSSTox Substance ID: DTXSID10431866
• Wikidata: Q82245866
• Mol file: 474645-91-5.mol

Synonyms:(3R)-3-(4-Trifluoromethyl-phenylamino)-pentanenitrile;474645-91-5;SCHEMBL5129528;DTXSID10431866

Chemical Property of (3R)-3-(4-Trifluoromethyl-phenylamino)-pentanenitrile

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• PSA: 35.82000
• LogP: 3.88258
• XLogP3: 4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 242.10308291
• Heavy Atom Count: 17
• Complexity: 271

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCC(CC#N)NC1=CC=C(C=C1)C(F)(F)F
• Isomeric SMILES: CC[C@H](CC#N)NC1=CC=C(C=C1)C(F)(F)F

Technology Process of (3R)-3-(4-Trifluoromethyl-phenylamino)-pentanenitrile

There total 4 articles about (3R)-3-(4-Trifluoromethyl-phenylamino)-pentanenitrile 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:

(R)-3-aminopentanenitrile methanesulfonic acid salt (474645-97-1) + 4-chlorobenzotrifluoride (98-56-6) + DavePhos (213697-53-1) + phenylboronic acid (98-80-6) → (R)-3-((4-(trifluoromethyl)phenyl)amino)pentanenitrile (474645-91-5)

Guidance literature:

With nitrogen; sodium carbonate; caesium carbonate; palladium diacetate; In tetrahydrofuran; dichloromethane; toluene;

Reference yield:

4-chlorobenzotrifluoride (98-56-6) + (R)-3-aminopentanenitrile (400090-60-0) → (R)-3-((4-(trifluoromethyl)phenyl)amino)pentanenitrile (474645-91-5)

Guidance literature:

4-chlorobenzotrifluoride; (R)-3-aminopentanenitrile; With caesium carbonate; In toluene; at 20 ℃; for 1h; Inert atmosphere;

With palladium diacetate; DavePhos; phenylboronic acid; In toluene; at 20 - 79 ℃; for 16h; Reagent/catalyst; Solvent; Inert atmosphere;

DOI:10.1021/op060013i

Reference yield:

(R)-3-aminopentanenitrile methanesulfonic acid salt (474645-97-1) + 4-chlorobenzotrifluoride (98-56-6) → (R)-3-((4-(trifluoromethyl)phenyl)amino)pentanenitrile (474645-91-5)

Guidance literature:

With palladium diacetate; caesium carbonate; DavePhos; phenylboronic acid; In dichloromethane; toluene; at 80 ℃;

DOI:10.1016/j.bmcl.2012.04.042

upstream raw materials:

(R)-3-aminopentanenitrile methanesulfonic acid salt

4-chlorobenzotrifluoride

DavePhos

phenylboronic acid

Downstream raw materials:

(2R,4S)-(2-ethyl-6-trifluoromethyl-1,2,3,4-tetrahydroquinolin-4-yl)carbamic acid benzyl ester

C₂₆H₂₄F₉N₃O₂

C₃₀H₃₁F₉N₆O₂

C₂₈H₂₆F₉N₇O₂

Refernces

• 1、 Damon, David B.,Dugger, Robert W.,Hubbs, Stephen E.,Scott, Jill M.,Scott, Robert W.. "Asymmetric synthesis of the cholesteryl ester transfer protein inhibitor torcetrapib". . p. 472 - 480. Retrieved 2012/12/22.