(R)-(-)-1-(1-Naphthyl)ethyl isothiocyanate

Base Information

• Chemical Name: (R)-(-)-1-(1-Naphthyl)ethyl isothiocyanate
• CAS No.: 138617-82-0
• Molecular Formula: C13H11NS
• Molecular Weight: 213.3
• Hs Code.: 2930909090
• DSSTox Substance ID: DTXSID10426818
• Nikkaji Number: J1.235.934I
• Mol file: 138617-82-0.mol

Synonyms:(R)-(-)-1-(1-Naphthyl)ethyl isothiocyanate;138617-82-0;1-[(1R)-1-ISOTHIOCYANATOETHYL]NAPHTHALENE;Naphthalene, 1-[(1R)-1-isothiocyanatoethyl]-;SCHEMBL3886974;DTXSID10426818;MFCD04039332;(R)-1-(1-Naphthyl)ethyl isothiocyanate;BP-12879;[(R)-1-(1-Naphthyl)ethyl] isothiocyanate

Chemical Property of (R)-(-)-1-(1-Naphthyl)ethyl isothiocyanate

Chemical Property:

• Vapor Pressure: 6.85E-05mmHg at 25°C
• Refractive Index: 1.6
• Boiling Point: 354.4°Cat760mmHg
• Flash Point: 177.8°C
• PSA: 44.45000
• Density: 1.08g/cm³
• LogP: 4.00360
• Sensitive.: Moisture Sensitive
• XLogP3: 5.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 213.06122053
• Heavy Atom Count: 15
• Complexity: 257

Purity/Quality:

99% ^*data from raw suppliers

(R)-(-)-1-(1-Naphthyl)ethylisothiocyanate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.; R36/37/38:Irritating to eyes, respiratory system
• Hazard Codes: R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.; R36/37/38:Irritating to eyes, respiratory system
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C1=CC=CC2=CC=CC=C21)N=C=S
• Isomeric SMILES: C[C@H](C1=CC=CC2=CC=CC=C21)N=C=S

Technology Process of (R)-(-)-1-(1-Naphthyl)ethyl isothiocyanate

There total 4 articles about (R)-(-)-1-(1-Naphthyl)ethyl isothiocyanate 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: 95.0%

carbon disulfide (75-15-0,12122-00-8) + (R)-1-(1-Naphthyl)ethylamine (3886-70-2) → (R)-[1-(1-naphthyl)ethyl] isothiocyanate (138617-82-0)

Guidance literature:

With dicyclohexyl-carbodiimide; In diethyl ether; at -10 - 20 ℃; for 15h;

DOI:10.1039/b517937h

Reference yield: 88.0%

thiophosgene (463-71-8) + (R)-1-(1-Naphthyl)ethylamine (3886-70-2) → (R)-[1-(1-naphthyl)ethyl] isothiocyanate (138617-82-0)

Guidance literature:

With sodium hydrogencarbonate; In dichloromethane; water; at 20 ℃;

DOI:10.1246/cl.2000.40

Reference yield:

((R)-1-Naphthalen-2-yl-ethyl)-dithiocarbamic acid; compound with triethyl-amine → (R)-[1-(1-naphthyl)ethyl] isothiocyanate (138617-82-0)

Guidance literature:

With 2-chloro-1,3-dimethylimidazolinium chloride; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1021/jo000745n

upstream raw materials:

thiophosgene

(R)-1-(1-Naphthyl)ethylamine

carbon disulfide

Downstream raw materials:

N-[(1S,2S)-2-tert-butoxycarbonylamino-1,2-diphenylethyl]-N'-[(R)-1-(1-naphthyl)ethyl]thiourea

(4S,5S)-1-tert-butoxycarbonyl-4,5-diphenyl-2-[(R)-1-(1-naphthyl)ethylimino]imidazolidine

Refernces

• 1、 Bassas, Oriol,Huuskonen, Juhani,Rissanen, Kari,Koskinen, Ari M.P.. "A simple organocatalytic enantioselective synthesis of pregabalin". experimental part. p. 1340 - 1351. Retrieved 2009/07/26.
• 2、 Jeon, Dong Ju,Kim, Jung Soo,Lee, Jung No,Kim, Hyoung Rae,Ryu, Eung K.. "(R)-[1-(1-Naphthyl)ethyl] isothiocyanate and (S)-1-phenylethyl isothiocyanate. New chirality recognizing reagents for the determination of enantiomeric purity of chiral amines by NMR". . p. 40 - 41. Retrieved 2007/10/03.