[(R)-alpha-(1-Naphthyl)benzyl]amine

Base Information

• Chemical Name: [(R)-alpha-(1-Naphthyl)benzyl]amine
• CAS No.: 3789-61-5
• Molecular Formula: C17H15N
• Molecular Weight: 233.313
• DSSTox Substance ID: DTXSID501282066
• Nikkaji Number: J467.568A
• Mol file: 3789-61-5.mol

Synonyms:DTXSID501282066;[(R)-alpha-(1-Naphthyl)benzyl]amine;(alphaR)-alpha-Phenyl-1-naphthalenemethanamine;3789-61-5

Chemical Property of [(R)-alpha-(1-Naphthyl)benzyl]amine

Chemical Property:

• Boiling Point: 400.5±14.0 °C(Predicted)
• Density: 1.125±0.06 g/cm3(Predicted)
• XLogP3: 4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 233.120449483
• Heavy Atom Count: 18
• Complexity: 256

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(C2=CC=CC3=CC=CC=C32)N
• Isomeric SMILES: C1=CC=C(C=C1)[C@H](C2=CC=CC3=CC=CC=C32)N

Technology Process of [(R)-alpha-(1-Naphthyl)benzyl]amine

There total 9 articles about [(R)-alpha-(1-Naphthyl)benzyl]amine 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: 74.0%

(R)-4-methyl-N-(naphthalen-1-yl(phenyl)methyl)benzenesulfonamide (66558-07-4) → (R)-α-(1-naphthyl)benzylamine (3789-61-5)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; samarium diiodide; In tetrahydrofuran; for 6h; Heating;

DOI:10.1021/ol060755w

Reference yield: 70.0%

4-Methyl-benzenesulfinic acid ((S)-naphthalen-1-yl-phenyl-methyl)-amide (66558-08-5,66558-10-9) → (R)-α-(1-naphthyl)benzylamine (3789-61-5) + (α1S)-α-phenyl-1-naphthalenemethanamine (6150-02-3,726124-83-0) + methyl (R)-4-methylbenzenesulfinate (64396-66-3)

Guidance literature:

With trifluoroacetic acid; In methanol; at 0 ℃; for 1h; Yield given. Title compound not separated from byproducts;

Reference yield:

phenyltriisopropoxytitanium(IV) (16635-23-7) → (R)-α-(1-naphthyl)benzylamine (3789-61-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / (S)-segphos / [RhCl(C₂H₄)2]2 / tetrahydrofuran / 1 h / 30 °C

2: 76 percent / NaAlH₂(OCH₂CH₂OCH₃)2 / toluene / 5 h / 80 °C

With (S)-((4,4’-bi-1,3-benzodioxole)-5,5’-diyl)bis(diphenylphosphine); sodium bis(2-methoxyethoxy)aluminium dihydride; bis(ethylene)rhodium(I) chloride dimer; In tetrahydrofuran; toluene;

DOI:10.1002/anie.200461338

upstream raw materials:

4-Methyl-benzenesulfinic acid ((S)-naphthalen-1-yl-phenyl-methyl)-amide

(R)-4-methyl-N-(naphthalen-1-yl(phenyl)methyl)benzenesulfonamide

phenyltriisopropoxytitanium(IV)

(1R,1'R)-2'-Hydroxy-1'-(phenylethyl)-1-(1-naphthyl)-phenylmethylamine

Downstream raw materials:

(R)-4-methyl-N-(naphthalen-1-yl(phenyl)methyl)benzenesulfonamide