1-Naphthyl isocyanate

Base Information

• Chemical Name: 1-Naphthyl isocyanate
• CAS No.: 86-84-0
• Molecular Formula: C11H7 N O
• Molecular Weight: 169.183
• Hs Code.: 29291090
• European Community (EC) Number: 201-703-7,250-067-7
• NSC Number: 4023
• UNII: 5LH2P0691E
• DSSTox Substance ID: DTXSID9058949
• Nikkaji Number: J56.211D
• Wikidata: Q27262522
• ChEMBL ID: CHEMBL2074791
• Mol file: 86-84-0.mol

Synonyms:1-isocyanatonaphthalene;1-naphthyl isocyanate;alpha-naphthyl isocyanate

Chemical Property of 1-Naphthyl isocyanate

Chemical Property:

• Appearance/Colour: colourless or slightly yellow liquid
• Vapor Pressure: 168.8 mm Hg ( 37.7 °C)
• Melting Point: 4-7 °C(lit.)
• Refractive Index: n20/D 1.6344(lit.)
• Boiling Point: 270 ºC
• Flash Point: 135 ºC
• PSA: 29.43000
• Density: 1.18
• LogP: 2.80710
• Storage Temp.: 0-10°C
• Sensitive.: Moisture Sensitive
• Solubility.: Miscible with alcohol, chloroform and diethyl ether.
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 169.052763847
• Heavy Atom Count: 13
• Complexity: 220

Purity/Quality:

99.9% ^*data from raw suppliers

1-Naphthyl isocyanate ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38-42
• Safety Statements: 9-16-25-33-60-61-62-36/37/39-26-45-27-23

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Toxic Gases & Vapors -> Monoisocyanates
• Canonical SMILES: C1=CC=C2C(=C1)C=CC=C2N=C=O
• Uses: 1-Naphthyl isocyanate is used in the preparation of cationic aromatic urethane. It is useful for the study of cholangiolitic hepatotoxicity in laboratory animals. It is also employed as separate enantiomers of beta-blockers.

Technology Process of 1-Naphthyl isocyanate

There total 13 articles about 1-Naphthyl isocyanate 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: 94.0%

bis(trichloromethyl) carbonate (32315-10-9) + 1-amino-naphthalene (134-32-7) → 1-Naphthyl isocyanate (86-84-0)

Guidance literature:

In ethyl acetate; for 4h; Heating;

DOI:10.1080/00397910601055156

Reference yield: 91.0%

methyl 1-naphthylcarbamate (5449-00-3) → 1-Naphthyl isocyanate (86-84-0)

Guidance literature:

With 2-chloro-1,3,2-benzodioxaborole; triethylamine; In toluene; 1.) reflux, 5 min, 2.) 0.5 h;

DOI:10.1021/jo00106a044

Reference yield: 86.13%

→ 1-Naphthyl isocyanate (86-84-0)

Guidance literature:

In 1,2-dichloro-ethane; at 0 - 20 ℃; Reflux;

upstream raw materials:

1-<(Triphenylphosphoranylidene)amino>naphthalene

methylammonium carbonate

phosgene

1-amino-naphthalene

Downstream raw materials:

N-[1]naphthyl-N'-p-tolyl-urea

[1]naphthyl-carbamic acid o-tolyl ester

N-[1]naphthyl-N'-phenethyl-urea

N-methyl-N'-[1]naphthyl-N-phenethyl-urea

Refernces

Synthesis and isolation of bromo-β-carbolines obtained by bromination of β-carboline alkaloids

10.1002/jhet.5570380512

The study focuses on the synthesis and isolation of bromo-β-carbolines, which are derivatives of β-carboline alkaloids. The researchers used N-bromosuccinimide (NBS) as the brominating agent to induce electrophilic aromatic substitution in various β-carbolines, including nor-harmane, harmane, harmine, harmol, and 7-acetylharmol. The purpose of using these chemicals was to explore the behavior of substituted β-carbolines, prepare nitro-β-carbolines and bromo-β-carbolines, and investigate their potential use as matrices (photosensitizers) in matrix-assisted ultraviolet laser desorption/ionization time-of-flight mass spectrometry (uv-maldi-tof ms). The study also aimed to understand the effects of substituents on the acid-base properties and electronic excited states of these molecules. The researchers compared the use of NBS in solution and in solid state, and employed semiempirical AM1 and PM3 calculations to predict reactivity in terms of molecular orbital energies and charge density. The results provided insights into the regioselectivity of bromination and the influence of the β-carboline/NBS molar ratio and reaction time on product selectivity.