1-Naphthyl isothiocyanate

Base Information

• Chemical Name: 1-Naphthyl isothiocyanate
• CAS No.: 551-06-4
• Deprecated CAS: 2124236-76-4
• Molecular Formula: C11H7 N S
• Molecular Weight: 185.249
• Hs Code.: 29309090
• European Community (EC) Number: 249-976-1,208-990-8
• NSC Number: 89741
• UN Number: 2811
• UNII: HG44814A3V
• DSSTox Substance ID: DTXSID8025703
• Nikkaji Number: J1.612H
• Wikipedia: 1-Naphthyl_isothiocyanate
• Wikidata: Q4545797
• Pharos Ligand ID: 593977YXG217
• Metabolomics Workbench ID: 55114
• ChEMBL ID: CHEMBL1381098
• Mol file: 551-06-4.mol

Synonyms:1 Naphthylisothiocyanate;1-Naphthylisothiocyanate;alpha Naphthylisothiocyanate;alpha-Naphthylisothiocyanate

Chemical Property of 1-Naphthyl isothiocyanate

Chemical Property:

• Appearance/Colour: white crystalline powder
• Melting Point: 55.5-57 ºC
• Refractive Index: 1.5500 (estimate)
• Boiling Point: 339.3°Cat760mmHg
• Flash Point: 167.2°C
• PSA: 44.45000
• Density: 1.11g/cm³
• LogP: 3.57410
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Water Solubility.: insoluble
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 185.02992040
• Heavy Atom Count: 13
• Complexity: 220
• Transport DOT Label: Poison

Purity/Quality:

99.3% ^*data from raw suppliers

1-Naphthyl isothiocyanate ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T
• Statements: 20/21-25-36/37/38-42-23/24/25
• Safety Statements: 22-26-36/37-45-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Isothiocyanates
• Canonical SMILES: C1=CC=C2C(=C1)C=CC=C2N=C=S
• Description: 1-Napthylisothiocyanate is a toxic chemical that has been used to create experimental cholestasis in rodents. Laboratory studies have also shown that 1-napthylisothiocyanate can act as a chemoprotectant in rodents challenged with a tumorinducing agent such as phorbol-12 myristate 13-acetate.
• Uses: 1-Naphthylisothiocyanate is used as an ingredient in insecticides. It is also found in cyanamide, which is used in many industrial applications. It is commonly used in medical and drug studies in animals as a model hepatotoxicant producing experimental cholestasis in rats and mice. 1-Naphthyl isothiocyanate is a tool for the study of liver damage which causes bile stasis and hyperbilirubinemia acutely and bile duct hyperplasia and biliary cirrhosis chronically, with changes in hepatocyte function. 1-Naphthyl isothiocyanate (NITC) can be used as a source of thiourea moiety to synthesize derivatives of calix[4]arenes to be used as anion acceptors. It can also be used for the synthesis of naphthyl substituted 1,2,4-triazoles and 1,3,4-thiadiazoles.

Technology Process of 1-Naphthyl isothiocyanate

There total 41 articles about 1-Naphthyl 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: 99.0%

carbon disulfide (75-15-0,12122-00-8) + 1-amino-naphthalene (134-32-7) → 1-isothiocyanatonaphthalene (551-06-4)

Guidance literature:

carbon disulfide; 1-amino-naphthalene; With triethylamine; In tetrahydrofuran; at 0 - 20 ℃;

With dmap; di-tert-butyl dicarbonate; In tetrahydrofuran; at 0 - 20 ℃; for 2h;

DOI:10.1002/cmdc.201500418

Reference yield: 99.0%

thiophosgene (463-71-8) + 1-amino-naphthalene (134-32-7) → 1-isothiocyanatonaphthalene (551-06-4)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1016/j.bmcl.2007.04.099

Reference yield: 98.0%

(naphth-1-ylamino)phenoxymethane-1-thione (29647-76-5) → 1-isothiocyanatonaphthalene (551-06-4)

Guidance literature:

With trichlorosilane; triethylamine; In benzene; at 20 ℃; for 1h;

DOI:10.1021/jo000139s

upstream raw materials:

N,N'-bis(1-naphthyl)thiourea

carbon disulfide

1-<(Triphenylphosphoranylidene)amino>naphthalene

thiophosgene

Downstream raw materials:

1-naphthalen-1-yl-3-phenyl-thiourea

1H-naphtho[1,2-d]thiazole-2-thione

1-naphthalen-1-yl-3-o-tolyl-thiourea

Refernces

• 1、 Cheng, Minghui,Meng, Xin,Tang, Haikang,Xu, Wenqing,Yang, Fujun,Zhang, Yuan. "Design, synthesis, and biological evaluation of novel substituted thiourea derivatives as potential anticancer agents for NSCLC by blocking K-Ras protein-effectors interactions". . p. 344 - 353. Retrieved 2019/12/30.
• 2、 Feng, Wei,Zhang, Xing-Guo. "Organophosphine-free copper-catalyzed isothiocyanation of amines with sodium bromodifluoroacetate and sulfur". supporting information. p. 1144 - 1147. Retrieved 2019/01/28.