2-Naphthylamine

Base Information

• Chemical Name: 2-Naphthylamine
• CAS No.: 91-59-8
• Molecular Formula: C10H9N
• Molecular Weight: 143.188
• Hs Code.: 2921.45
• European Community (EC) Number: 210-313-6,202-080-4
• ICSC Number: 0610
• UN Number: 1650
• UNII: CKR7XL41N4
• DSSTox Substance ID: DTXSID2020921
• Nikkaji Number: J3.925J
• Wikipedia: 2-Naphthylamine
• Wikidata: Q209450
• NCI Thesaurus Code: C44311
• Metabolomics Workbench ID: 49545
• ChEMBL ID: CHEMBL278164
• Mol file: 91-59-8.mol

Synonyms:2 Aminonaphthalene;2 Naphthylamine;2-Aminonaphthalene;2-Naphthylamine;beta Naphthylamine;beta-Naphthylamine

Chemical Property of 2-Naphthylamine

Chemical Property:

• Appearance/Colour: Light brown sSolid
• Vapor Pressure: 2.56 x 10-4 mmHg at 20–30 °C (quoted, Mercer et al., 1990)
• Melting Point: 111-113 °C(lit.)
• Refractive Index: 1.5000 (estimate)
• Boiling Point: 307.5 °C at 760 mmHg
• PKA: 4.16(at 25℃)
• Flash Point: 157.1 °C
• PSA: 26.02000
• Density: 1.137 g/cm³
• LogP: 3.00320
• Storage Temp.: -20°C Freezer
• Solubility.: Solubility Soluble in hot water, ethanol, ether
• Water Solubility.: <0.1 g/100 mL at 22℃
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 143.073499291
• Heavy Atom Count: 11
• Complexity: 133
• Transport DOT Label: Poison

Purity/Quality:

99% ^*data from raw suppliers

2-Naphthylamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T; N
• Hazard Codes: T,N
• Statements: 45-22-51/53
• Safety Statements: 53-45-61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Naphthylamines
• Canonical SMILES: C1=CC=C2C=C(C=CC2=C1)N
• Inhalation Risk: Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly when dispersed.
• Effects of Short Term Exposure: The substance may be irritating to the respiratory tract and skin. The substance may cause effects on the blood. This may result in the formation of methaemoglobin. The substance may cause effects on the bladder. This may result in inflammation and blood in the urine. Medical observation is indicated. The effects may be delayed.
• Effects of Long Term Exposure: This substance is carcinogenic to humans.
• Uses: Amino and nitrite of Aminonaphthalene can form diazonium salt, and can turn into a variety of hydrocarbon derivatives of naphthalene, it can be used in the manufacture of dyes and organic synthesis, also used as indicators of organic analytical reagents and fluorescent agents. It is listed as a known human carcinogen. Used in manufacturing of dyes, as antioxidant in rubber An amine compound used for research purposes 2-Naphthylamine was widely used in themanufacture of dyes and in rubber. Currently, its use is curtailed because of thehealth hazard.
• Production method: Since the nitration of naphthalene can not obtain 2-nitro-naphthalene, so the producing methods is different from 1-Naphthylamine. 2-Naphthylamine is derived by 2-naphthol pressurized ammonia solution.
• Physical properties: White crystals becomes purplish-red on exposure to air. Odor threshold concentrations ranged from 1.4 to 1.9 mg/m3 (quoted, Keith and Walters, 1992).

Technology Process of 2-Naphthylamine

There total 199 articles about 2-Naphthylamine 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: 42.0%

methanol (67-56-1) + 2-azidonaphthalene (20937-86-4) → 2-nitronaphthalene (581-89-5) + 2-methoxynaphthylamine (2246-42-6) + dibenzo[a,h]phenazine (226-47-1) + 1-amino-2-chloronaphthalene (13711-39-2) + naphthalen-2-ylamine (91-59-8) + 2,2'-azonaphthalene (582-08-1)

Guidance literature:

With hydrogenchloride; Product distribution; Irradiation;

Reference yield: 10.0%

naphthalene (91-20-3,71998-51-1,72931-45-4) → 1-amino-naphthalene (134-32-7) + naphthalen-2-ylamine (91-59-8)

Guidance literature:

With tris-(2-chloro-ethyl)-amine; trifluorormethanesulfonic acid; trifluoroacetic acid; In chloroform; at 25 ℃; for 12h;

Reference yield: 2.0%

2-azidonaphthalene (20937-86-4) + potassium cyanide (151-50-8) → 2-nitronaphthalene (581-89-5) + dibenzo[a,h]phenazine (226-47-1) + 2-aminonaphthalene-1-carbonitrile (7066-13-9) + 1-amino-2-naphthalenecarbonitrile (3100-67-2) + naphthalen-2-ylamine (91-59-8) + 2,2'-azonaphthalene (582-08-1)

Guidance literature:

In water; acetonitrile; Product distribution; Irradiation;

upstream raw materials:

naphthalene

4-bromo-2-nitronaphthalene

2-nitronaphthalene

1-<(2-Amino-1-naphthyl)methyl>-2-naphthol

Downstream raw materials:

N-(naphthalen-2-yl)-3-oxobutanamide

3-[2]naphthylamino-crotonic acid-[2]naphthylamide

N-(2-thienylmethylene)-2-naphthalenamine

N-(2-naphthalenyl)-pyrrolidine-2,5-dione

Refernces

New mesogenic homologous series of schiff base cinnamates comprising naphthalene moiety

10.1080/10587250307066

The research presents the synthesis and characterization of a new mesogenic homologous series of Schiff base cinnamates that incorporate a naphthalene moiety. The study aimed to understand the impact of the ethylene linking group (cinnamoyl linkage) and the naphthalene moiety on the mesomorphic properties of these molecules. The reactants used in the synthesis included 4-(40-n-alkoxy cinnamoyloxy) benzaldehydes, 2-amino naphthalene, malonic acid, n-alkyl halide, K2CO3, p-hydroxy benzaldehyde, and solvents like ethanol, which were dried prior to use. The synthesized compounds were characterized using elemental analysis and various spectroscopic techniques, including infrared (IR), ultraviolet (UV), and proton nuclear magnetic resonance (1H NMR) spectroscopy. The study found that all synthesized compounds exhibited mesomorphism, and the mesophase properties were compared with other structurally related series. The results indicated that the presence of the naphthalene moiety and the cinnamoyl linkage influenced the mesophase transition temperatures and the overall thermal stability of the mesophases.

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