4-Chloro-1-naphthol

Base Information

• Chemical Name: 4-Chloro-1-naphthol
• CAS No.: 604-44-4
• Molecular Formula: C10H7 Cl O
• Molecular Weight: 178.618
• Hs Code.: 2908199090
• European Community (EC) Number: 210-068-5
• NSC Number: 44345
• UNII: P4NNY2FQ2A
• DSSTox Substance ID: DTXSID3060536
• Nikkaji Number: J95.406C
• Wikidata: Q22668708
• ChEMBL ID: CHEMBL3310663
• Mol file: 604-44-4.mol

Synonyms:4-chloro-1-naphthalenol;4-chloro-1-naphthol

Chemical Property of 4-Chloro-1-naphthol

Chemical Property:

• Appearance/Colour: Off white to tan crystals
• Vapor Pressure: 7.74E-05mmHg at 25°C
• Melting Point: 118-121 °C(lit.)
• Refractive Index: 1.4575 (estimate)
• Boiling Point: 332.1oC at 760 mmHg
• PKA: 9.11±0.40(Predicted)
• Flash Point: 73°C
• PSA: 20.23000
• Density: 1.333g/cm3
• LogP: 3.19880
• Storage Temp.: 2-8°C
• Solubility.: methanol: 50 mg/mL, clear, colorless to very faintly yellow
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 178.0185425
• Heavy Atom Count: 12
• Complexity: 160

Purity/Quality:

99% ^*data from raw suppliers

4-Chloro-1-naphthol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,T
• Statements: 36/37/38-39/23/24/25-20/21/22
• Safety Statements: 26-36-45-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Naphthols
• Canonical SMILES: C1=CC=C2C(=C1)C(=CC=C2Cl)O
• General Description: **4-Chloro-1-naphthol** is a key intermediate used in the synthesis of halogenated benzo[h]chromene and benzo[a]anthracene derivatives with antimicrobial properties. It reacts with 4-halobenzylidenmalononitriles and ethyl 4-halobenzylidenmalonates in the presence of ethanolic piperidine to form intermediates that are further derivatized into bioactive compounds. While the study focuses on the antimicrobial potential of the final products, 4-chloro-1-naphthol itself serves as a crucial building block in these synthetic pathways. **Return:** 4-Chloro-1-naphthol is a synthetic intermediate used in the preparation of antimicrobial halogenated benzo[h]chromene and benzo[a]anthracene derivatives, demonstrating its utility in medicinal chemistry.

Technology Process of 4-Chloro-1-naphthol

There total 29 articles about 4-Chloro-1-naphthol 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: 76.0%

α-naphthol (90-15-3) → 4-chloronaphthalen-1-ol (604-44-4) + 2-chloro-1-naphthol (606-40-6)

Guidance literature:

With sulfuryl dichloride; In 1,2-dichloro-ethane; at 0 - 25 ℃; for 7h;

DOI:10.1002/asia.201000804

Reference yield: 44.0%

α-naphthol (90-15-3) → 4-chloronaphthalen-1-ol (604-44-4) + 2,4-dichloronaphthol (2050-76-2) + 2-chloro-1-naphthol (606-40-6)

Guidance literature:

With sulfuryl dichloride; In dichloromethane; at 0 ℃; for 3.5h;

DOI:10.1002/asia.201000804

Reference yield: 40.0%

α-naphthol (90-15-3) → 4-chloronaphthalen-1-ol (604-44-4)

Guidance literature:

With sulfuryl dichloride; In chlorobenzene; at 20 - 73 ℃; for 15h;

DOI:10.1002/asia.201000804

upstream raw materials:

α-naphthol

1-chloro-4-methoxynaphthalene

pyridine hydrochloride

1-naphthyl tosylate

Downstream raw materials:

indophenol blue

(6-chloro-2-oxo-2H-benzo[h]chromen-4-yl)-acetic acid

1-(4-chloro-1-hydroxy-2-naphthyl)ethanone

2,4-dichloronaphthol

Refernces

Synthesis of halogen derivatives of benzo[h]chromene and benzo[a]anthracene with promising antimicrobial activities.

10.1016/S0014-827X(02)01263-6

The study reports the synthesis and antimicrobial evaluation of novel 7-(4-halophenyl)-8,9-dihydro-7H-12-oxa-9,11-diaza-benzo[a]anthracene derivatives. The key intermediate, 3-amino-9-chloro-1-(4-halophenyl)-1H-benzo[h]chromene-2-carbonitrile (3), was synthesized by reacting 4-halobenzylidenmalononitriles (1a–c) and ethyl 4-halobenzylidenmalonates (1d–f) with 4-chloro-1-naphthol (2) in an ethanolic piperidine solution. This intermediate was then used to produce a variety of derivatives through reactions with acetic anhydride, benzaldehydes, hydrazine, triethyl orthoformate, and other reagents, resulting in compounds such as 5-chloro-10-methyl-7-(4-halophenyl)-8,9-dihydro-7H-12-oxa-9,11-diaza-benzo[a]anthracene-8-one (6a–c) and 9-amino-5-chloro-8-imino-7-(4-halophenyl)-8,9-dihydro-7H-12-oxa-9,11-diaza-benzo[a]anthracene (11a–c). The synthesized compounds were characterized using IR, UV, 1H NMR, and mass spectroscopy. The antimicrobial activity of these compounds was tested against various bacterial and fungal strains, with several compounds showing significant activity. The study highlights the potential of these synthesized compounds as new antimicrobial agents.