604-44-4

Basic information

• Product Name: 4-CHLORO-1-NAPHTHOL
• Synonyms: 4-chloro-1-nahphthol;4-chloro-1-naphthaleno;4-chloro-1-Naphthalenol;CHLORONAPHTHOL;CHLORONAPTHOL;1-CHLORO-4-HYDROXYNAPHTHALENE;4-CN;4CN PLUS
• CAS NO: 604-44-4
• Molecular Formula: C₁₀H₇ClO
• Molecular Weight: 178.61
• EINECS: 210-068-5
• Product Categories: Naphthalene derivatives;Biochemistry;Enzyme;Substrates;Enzyme Substrates;Peroxidase Substrates;Substrates by Enzyme;Alphabetical ListingWestern Blotting;PeroxidaseWestern Blotting;Tablets;Fluorescent Enzyme Substrates for ElectrophoresisEnzyme Substrates;Peroxidase SubstratesAnalytical Reagents;Fluorescent Enzyme Substrates;Fluorescent Probes, Labels, Particles and Stains;Microscopy Reagents;Stains and Dyes;BiochemicalsWestern Blotting;Molecular Biology;Molecular Biology Reagents;Peroxidase;Fluorescent Enzyme Substrates for ElectrophoresisWestern Blotting;Alphabetical ListingFluorescent Probes, Labels, Particles and Stains;Detection Substrates;Powders
• Mol File: 604-44-4.mol
• Article Data: 15

Chemical Properties

• Melting Point: 118-121 °C(lit.)
• Boiling Point: 254.41°C (rough estimate)
• Flash Point: 73 °C
• Appearance: Off-white to gray to light brown/tablets (~32 mg each)
• Density: 密度
• Vapor Pressure: 7.74E-05mmHg at 25°C
• Refractive Index: 1.4575 (estimate)
• Storage Temp.: 2-8°C
• Solubility: methanol: 50 mg/mL, clear, colorless to very faintly yellow
• PKA: 9.11±0.40(Predicted)
• BRN: 509750
• CAS DataBase Reference: 4-CHLORO-1-NAPHTHOL(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLORO-1-NAPHTHOL(604-44-4)
• EPA Substance Registry System: 4-CHLORO-1-NAPHTHOL(604-44-4)

Safety Data

• Hazard Codes: Xi,T
• Statements: 36/37/38-39/23/24/25-20/21/22
• Safety Statements: 26-36-45-36/37
• RIDADR: UN 2810 6.1/PG 3
• WGK Germany: 3
• F: 8-9-23
• TSCA: Yes
• Hazardous Substances Data: 604-44-4(Hazardous Substances Data)

Usage

Chemical Properties

Off white to tan crystals

Uses

Different sources of media describe the Uses of 604-44-4 differently. You can refer to the following data:
1. 4-Chloro-1-naphthol has been used to visualize protein bands in western blotting. It has also been used in staining polyvinylidene fluoride (PVDF) membrane by Nakane method.
2. Suitable for visualizing protein-peroxidase conjugates in western blotting.

Synthesis Reference(s)

Tetrahedron, 38, p. 2347, 1982 DOI: 10.1016/0040-4020(82)87012-9

General Description

4-Chloro-1-naphthol is primarily used for the detection of proteins, it gives a characteristic purple precipitate and the reactions are easily controllable. It can be used as a substitute for benzidine compounds, which are considered to be carcinogenic.

Biochem/physiol Actions

4-Chloro-1-naphthol serves as a substrate for horseradish peroxidase.

Purification Methods

Crystallise the naphthol from EtOH or CHCl3. [Beilstein 6 H 611, 6 II 582, 6 III 2933, 6 IV 4233.]

InChI:InChI=1/C10H7ClO/c11-9-5-6-10(12)8-4-2-1-3-7(8)9/h1-6,12H

Upstream product

• 90-15-3 α-naphthol 
• 10443-43-3 1-chloro-4-methoxynaphthalene 
• 628-13-7 pyridine hydrochloride 
• 94688-65-0 4,4'-trisulfanediyl-di-[1]naphthol 
• 68211-49-4 1-naphthyl tosylate 
• 90-13-1 1-Chloronaphthalene 
• 86-48-6 1-hydroxy-2-naphthoic acid 
• 2216-69-5 1-Methoxynaphthalene 
• 871887-68-2 5-chloro-8-hydroxy-naphthalene-1-sulfonic acid 
• 7732-18-5 water 
• 7791-25-5 sulfuryl dichloride 
• 60-29-7 diethyl ether 
• 302938-42-7 di(4-hydroxy-1-naphthyl)disulfide 
• 71-43-2 benzene 

Downstream Products

• 75365-96-7 (6-chloro-2-oxo-2H-benzo[h]chromen-4-yl)-acetic acid 
• 530740-47-7 1-(4-chloro-1-hydroxy-2-naphthyl)ethanone 
• 2050-76-2 2,4-dichloronaphthol 
• 38710-97-3 2-Amino-5-(4-chloro-naphthalen-1-yloxy)-benzonitrile 
• 7469-77-4 2-methylnaphthalen-1-ol 
• 30235-98-4 3-(4-bromophenyl)naphthalen-1-ol 
• 30069-65-9 3-phenylnaphthalen-1-ol 
• 72774-01-7 4,4-diphenyl-3,4-dihydronaphthalen-1(2H)-one 
• 57396-88-0 C₁₄H₁₁ClO₄ 
• 198645-64-6 ethyl 2-amino-6-chloro-4-(4-methylphenyl)-4H-benzo[h]chromene-3-carboxylate 

Relevant articles and documents

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Regioselective Oxidative Chlorination of Arenols Using NaCl and Oxone

We developed a practical and environmentally benign method for the chlorinative dearomatization of arenols using transient electrophilic chlorinating species generated in situ from inexpensive sodium chloride and Oxone as a Cl source and oxidant, respectively, under mild conditions. Moreover, the regioselective chlorination or chlorinative dearomatization of 1-naphthols was also achieved by changing the reaction conditions.

Role of substituents on the reactivity and product selectivity in reactions of naphthalene derivatives catalyzed by the orphan thermostable cytochrome P450, CYP175A1

The thermostable nature of CYP175A1 enzyme is of potential interest for the biocatalysis at ambient temperature or at elevated temperature under environmentally benign conditions. Although little is known about the substrate selectivity of this enzyme, the biocatalytic activities of CYP175A1 on different substituted naphthalenes have been studied in oxidative pathway, and the effect of the substituent on the reaction has been determined. The enzyme first acts as a peroxygenase to convert these substituted naphthalenes to the corresponding naphthols, which subsequently undergo in-situ oxidative dimerization to form dyes of different colors possibly by the peroxidase-type activity of CYP175A1. The product analyses and kinetic measurements suggested that the presence of electron releasing substituent (ERS) in the substrate enhanced the substrate conversion, whereas the presence of electron withdrawing substituent (EWS) in the substrate drastically reduced the substrate conversion. The position of the ERS in the substrate was also found to play an important role in the transformation of the substrate. The results further demonstrate that mutation of the Leu80 residue to Phe enhances the reactivity of the enzyme by favoring the substrate association in the active site. The observed rates of the enzymatic oxygenation reaction of the substituted naphthalenes followed the Hammett correlation of substituent effect, supporting aromatic electrophilic substitution mechanism catalyzed by the cytochrome P450 enzyme.