24781-50-8

Basic information

• Product Name: 3-(NAPHTHALEN-1-YL)PROPAN-1-AMINE
• Synonyms: 3-(NAPHTHALEN-1-YL)PROPAN-1-AMINE;[3-(1-naphthyl)propyl]amine;3-(1-naphthyl)propan-1-amine;3-(1-naphthyl)propylamine
• CAS NO: 24781-50-8
• Molecular Formula: C₁₃H₁₅N
• Molecular Weight: 185.26
• Mol File: 24781-50-8.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 328.899 °C at 760 mmHg
• Flash Point: 159.425 °C
• Appearance: /
• Density: 1.049 g/cm³
• PKA: 10.22±0.10(Predicted)
• CAS DataBase Reference: 3-(NAPHTHALEN-1-YL)PROPAN-1-AMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(NAPHTHALEN-1-YL)PROPAN-1-AMINE(24781-50-8)
• EPA Substance Registry System: 3-(NAPHTHALEN-1-YL)PROPAN-1-AMINE(24781-50-8)

Safety Data

• Hazardous Substances Data: 24781-50-8(Hazardous Substances Data)

Usage

General Description

3-(Naphthalen-1-yl)propan-1-amine, also known as beta-naphthylpropylamine, is a chemical compound that is derived from naphthalene and belongs to the class of amines. It is a colorless to pale yellow liquid with a strong amine odor and is insoluble in water but soluble in most organic solvents. This chemical has various industrial and commercial uses, such as being used as a chemical intermediate in the production of pharmaceuticals, dyes, and other organic compounds. However, it is important to handle this chemical with caution as it can be harmful if swallowed, inhaled, or comes in contact with skin, and proper safety precautions should be taken when dealing with it.

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Relevant articles and documents

Studies on the solvent dependence of the carbamic acid formation from ω-(1-naphthyl)alkylamines and carbon dioxide

Carbamic acid formation from amine and carbon dioxide in a variety of solvents was investigated by measuring NMR (1H, 13C, HMBC) and IR spectra in situ. Bubbling of CO2 through solutions of naphthylalkylamines 1-3 in DMSO, DMF or pyridine (protophilic, highly dipolar, aprotic solvent) resulted in complete conversion of the amines to the corresponding carbamic acids 4-6. In dioxane (protophilic, dipolar, aprotic solvent), the carbamic acid and a small amount of the ammonium carbamate were formed. By contrast, in MeCN (protophobic, dipolar, aprotic solvent), in benzene or CHCl3 (apolar, aprotic solvent), or in 2-PrOH or MeOH (dipolar, amphiprotic solvent), ammonium carbamates 7-9 rather than 4-6 were formed, although the ammonium bicarbonates/carbonates were competitively formed in MeOH. The ammonium carbamates precipitated in many cases and hence they could be separated. The selective generation of the undissociated carbamic acids in preference to the ammonium carbamates in protophilic, dipolar, aprotic solvents (DMSO, DMF, pyridine, and dioxane) is rationalized by considering the acid-base equilibria between the amines 1-3 and the carbamic acids 4-6 in nonaqueous media. The obtained selectivity is likely due to the larger pKa values for 4-6 than the amines 1-3 in these solvents. Interestingly, the fluorescence intensities for 1-3 were dramatically enhanced (4-50 times) in DMSO or DMF upon introduction of CO2, while they were not altered very much in dioxane, MeCN, benzene, CHCl3, 2-PrOH, and MeOH, except small to medium increases (1.3-3 times) for 1 in dioxane, MeCN, 2-PrOH and MeOH. As a whole, the solvent effects observed in these fluorescence studies are consistent with those observed in the above NMR and IR studies. Finally, methoxycarbonylation of amine 3 into the methyl carbamate was successfully accomplished by using (trimethylsilyl)diazomethane in the presence of CO 2. Probably due to pKa(6)>pKa(3) in protophilic dipolar aprotic solvents, the conversion 3→6 is nearly complete while the formation of 9 is minimal.

Structure-based design and synthesis of high affinity tripeptide ligands of the Grb2-SH2 domain

The X-ray structure of the Grb2-SH2 domain in complex with a specific phosphopeptide ligand has revealed the existence of an extended hydrophobic area adjacent to the primary binding site of the ligand on the SH2 domain. This has been exploited to design hydrophobic C-terminal groups that improve the binding affinity of the minimal sequence pTyr-Ile-Asn recognized by the Grb2-SH2 domain. The most significant increase in affinity (25-fold compared to that of the reference peptide having a nonsubstituted carboxamide C- terminus) was obtained with a 3-naphthalen-1-yl-propyl group which was predicted to have the largest contact area with the SH2 domain hydrophobic region. This modification combined with replacement of the minimal sequence isoleucine residue by 1-aminocyclohexane carboxylic acid to stabilize the β- turn conformation required for recognition by the Grb2-SH2 domain resulted in the high affinity (47 nM in an ELISA assay) and selective phosphopeptide Ac- pTyr-Ac6c-Asn-NH(3-naphthalen-1-yl-propyl).

A new type of ketolides bearing an N-aryl-alkyl acetamide moiety at the C-9 iminoether synthesis and structure-activity relationships

A new type of ketolides, bearing an N-aryl-alkyl acetamide moiety at the C-9 iminoether and a cyclic carbonate at the C-11,12 position was prepared and the antibacterial activities of the compounds were evaluated. Some of the derivatives showed potent ant