(1-Isoquinolin-1-ylnaphthalen-2-yl)-diphenylphosphane

Base Information

• Chemical Name: (1-Isoquinolin-1-ylnaphthalen-2-yl)-diphenylphosphane
• CAS No.: 149341-34-4
• Molecular Formula: C₃₁H₂₂NP
• Molecular Weight: 439.496
• Hs Code.: 29334990
• European Community (EC) Number: 695-230-7,802-896-6,808-767-0
• DSSTox Substance ID: DTXSID601318345
• Nikkaji Number: J1.147.192G,J915.684D,J2.171.121G
• Mol file: 149341-34-4.mol

Synonyms:149341-33-3;149245-03-4;149341-34-4;QUINAP;(R)-(+)-1-(2-DIPHENYLPHOSPHINO-1-NAPHTHYL)ISOQUINOLINE;(1-isoquinolin-1-ylnaphthalen-2-yl)-diphenylphosphane;(S)-1-(2-(Diphenylphosphino)naphthalen-1-yl)isoquinoline;(RS)-1-(2-DIPHENYLPHOSPHINO-1-NAPHTHYL)ISOQUINOLINE;(R)-QUINAP;(S)-QUINAP;(1-(1-Isoquinolinyl)-2-naphthyl)diphenylphosphine;Isoquinoline, 1-[2-(diphenylphosphino)-1-naphthalenyl]-;(R)-1-(2-(Diphenylphosphanyl)naphthalen-1-yl)isoquinoline;Isoquinoline, 1-[2-(diphenylphosphino)-1-naphthalenyl]-, (1S)-;SCHEMBL225995;YMJAIEYASUCCMJ-UHFFFAOYSA-N;DTXSID601318345;(S)-(-)-1-(2-Diphenylphosphino-1-naphthyl)isoquinoline (S)-QUINAP;MFCD01073773;SC11381;BP-12299;CS-0165869;FT-0755419;FT-0769701;E85041;(aR)-1-[2-(Diphenylphosphino)-1-naphthyl]isoquinoline;(RS)-1-(2-Diphenylphosphino-1-naphthyl)isoquinoline, 95%;(R)-(+)-1-(2-Diphenylphosphino-1-naphthyl)isoquinoline R-QUINAP;(R)-(+)-1-(2-diphenylphosphino-1-naphthyl)isoquinoline, AldrichCPR;(R)-(+)-1-(2-Diphenylphosphino-1-naphtyl)isoquinoline R-QUINAR;(S)-(-)-1-(2-Diphenylphosphino-1-naphthyl)isoquinoline S-QUINAP;(R)-(+)-1-(2-Diphenylphosphino-1-naphthyl)isoquinoline, >=95.0% (qNMR);(S)-(-)-1-(2-Diphenylphosphino-1-naphthyl)isoquinoline, >=95.0% (qNMR);(S)-(-)-1-(2-DIPHENYLPHOSPHINO-1-NAPHTHYL)ISOQUINOLINE;(R)-(+)-2-[2-(Diphenylphosphino)phenyl]-4-(1-methylethyl)-4,5-dihydrooxazole

Chemical Property of (1-Isoquinolin-1-ylnaphthalen-2-yl)-diphenylphosphane

Chemical Property:

• Melting Point: 226-230°C
• Boiling Point: 588.1±38.0 °C(Predicted)
• PKA: 4.45±0.30(Predicted)
• PSA: 26.48000
• LogP: 6.81320
• Storage Temp.: 2-8°C
• XLogP3: 7.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 439.148986704
• Heavy Atom Count: 33
• Complexity: 590

Purity/Quality:

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

(R)-(+)-1-(2-Diphenylphosphino-1-naphthyl)isoquinoline ≥95.0% (qNMR) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 20/21/22-53-36/37/38
• Safety Statements: 22-36/37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=NC=CC6=CC=CC=C65

Technology Process of (1-Isoquinolin-1-ylnaphthalen-2-yl)-diphenylphosphane

There total 32 articles about (1-Isoquinolin-1-ylnaphthalen-2-yl)-diphenylphosphane 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: 99.0%

1-(2-bromonaphthalen-1-yl)isoquinoline (1000062-70-3) + diphenylphosphane (829-85-6) → (R,S)-(±)-1-(2-diphenylphosphino-1-naphthyl)isoquinoline (149341-33-3,149245-03-4,149341-34-4)

Guidance literature:

diphenylphosphane; With copper(l) iodide; N,N`-dimethylethylenediamine; In toluene; at 20 ℃; for 0.5h; Inert atmosphere;

1-(2-bromonaphthalen-1-yl)isoquinoline; With caesium carbonate; In toluene; at 20 - 100 ℃; Inert atmosphere;

DOI:10.1039/b913336d

Reference yield: 90.0%

1-(2-trifluoromethanesulfonyloxy-1-naphthyl)isoquinoline (149245-06-7) + (trimethylsilyl)diphenylphosphine (17154-34-6) → (R,S)-(±)-1-(2-diphenylphosphino-1-naphthyl)isoquinoline (149341-33-3,149245-03-4,149341-34-4)

Guidance literature:

With 1,3-bis-(diphenylphosphino)propane; cesium fluoride; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In 1,4-dioxane; at 65 ℃; for 20h; Glovebox; Inert atmosphere;

DOI:10.1021/jacs.6b07972

Reference yield: 85.0%

1-(2-trifluoromethanesulfonyloxy-1-naphthyl)isoquinoline (149245-06-7) + diphenylphosphane (829-85-6) → (R,S)-(±)-1-(2-diphenylphosphino-1-naphthyl)isoquinoline (149341-33-3,149245-03-4,149341-34-4)

Guidance literature:

With dmap; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; o-phenylenebis(diphenylphosphine); In 1,4-dioxane; at 80 ℃; for 24h; Schlenk technique; Inert atmosphere;

upstream raw materials:

(1-(isoquinolin-1-yl)naphthalen-2-yl)diphenylphosphine oxide

chloro-diphenylphosphine

1-(2-trifluoromethanesulfonyloxy-1-naphthyl)isoquinoline

1-(2-hydroxy-1-naphthyl)isoquinoline

Downstream raw materials:

[Cu(1-(2-diphenylphosphini-1-naphthyl)isoquinoline)I]2

(1-(isoquinolin-1-yl)naphthalen-2-yl)diphenylphosphine oxide

Refernces

• 1、 -. "1-aryl isoquinoline compound and synthetic method thereof". . . Retrieved 2020/11/25.
• 2、 Bhat, Vikram,Wang, Su,Stoltz, Brian M.,Virgil, Scott C.. "Asymmetric synthesis of QUINAP via dynamic kinetic resolution". . p. 16829 - 16832. Retrieved 2013/12/04.