15231-91-1

Basic information

• Product Name: 6-Bromo-2-naphthol
• Synonyms: 2-Naphthol, 6-bromo-;6-bromo-2-naphthaleno;6-bromo-2-naphtho;6-Bromo-beta-naphthol;Bromo-6 naphtol-2;bromo-6naphtol-2;6-BROMO-2-NAPHTHOL;6-BROMO-2-NAPHTHALENOL
• CAS NO: 15231-91-1
• Molecular Formula: C₁₀H₇BrO
• Molecular Weight: 223.07
• EINECS: 239-279-0
• Product Categories: Aromatic Phenols;Heterocycles series;Halides;Phenoles and thiophenoles;Fused Ring Systems;Organic Building Blocks;Oxygen Compounds;Phenols;Building Blocks;C9 to C20+;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds
• Mol File: 15231-91-1.mol

Chemical Properties

• Melting Point: 122-124 °C(lit.)
• Boiling Point: 130°C (rough estimate)
• Flash Point: 167.8 °C
• Appearance: Off-white to beige/Powder
• Density: 1.4412 (rough estimate)
• Vapor Pressure: 1.71E-05mmHg at 25°C
• Refractive Index: 1.5700 (estimate)
• Storage Temp.: Store at RT.
• Solubility: Chloroform, Methanol
• PKA: 9.26±0.40(Predicted)
• Water Solubility: 不溶于水，溶于醇。
• BRN: 1100270
• CAS DataBase Reference: 6-Bromo-2-naphthol(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Bromo-2-naphthol(15231-91-1)
• EPA Substance Registry System: 6-Bromo-2-naphthol(15231-91-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• RTECS: QL3365000
• Hazardous Substances Data: 15231-91-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
6-Bromo-2-naphthol is used as a pharmaceutical agent for its steroid hormone activity. Its potential application in anticancer therapy makes it a promising candidate for the development of new cancer treatments.
Used in Anticancer Applications:
In the field of oncology, 6-Bromo-2-naphthol is utilized as an anticancer agent. Its steroid hormone activity may contribute to the modulation of various cancer-related signaling pathways, potentially leading to the inhibition of tumor growth and progression. Further research and development are necessary to fully understand its efficacy and potential synergistic effects when combined with conventional chemotherapeutic drugs.
Used in Chemical Research:
6-Bromo-2-naphthol's unique chemical structure and properties make it a valuable compound for chemical research. It can be used in the synthesis of various organic compounds and may serve as a building block for the development of new pharmaceuticals and other chemical products.

Purification Methods

Crystallise the naphthol from EtOH or *C6H6/pet ether (m 128o). The benzoyl derivative has m 122o, (from EtOH). [Ruggli & Michels Helv Chim Acta 14 779 1931, Beilstein 6 H 651, 6 II 605, 6 III 2996.]

InChI:InChI=1/C10H7BrO/c11-9-3-1-8-6-10(12)4-2-7(8)5-9/h1-6,12H

Upstream product

• 16239-18-2 1,6-dibromo-2-naphthol 
• 102153-55-9 3,6-dibromo-[2]naphthol 
• 102153-54-8 4,6-dibromo-β-naphthol 
• 116632-10-1 1,4,6-tribromo-[2]naphthol 
• 98994-65-1 1,3,4,6-tetrabromo-[2]naphthol 
• 610277-16-2 6-bromo-2-methoxy-1-naphthoic acid 
• 64-19-7 acetic acid 
• 135-19-3 β-naphthol 
• 108-85-0 1-bromocyclohexane 
• 78232-03-8 6-bromo-2-naphthoxide anion 
• 6343-72-2 6-bromonaphthalen-2-yl acetate 
• 5111-65-9 2-Bromo-6-methoxynaphthalene 
• 10035-10-6 hydrogen bromide 
• 66217-19-4 2-ethoxy-6-bromo-naphthalene 

Downstream Products

• 5111-65-9 2-Bromo-6-methoxynaphthalene 
• 97476-14-7 2-propyloxy-6-bromonaphthalene 
• 16712-64-4 6-Hydroxy-2-naphthoic acid 
• 873381-94-3 7-bromo-1,2-diphenyl-naphtho[2,1-b]furan 
• 7499-66-3 6-Bromonaphthalen-2-amine 
• 2065-70-5 2,6-dichloronaphthalene 
• 6954-48-9 6-bromo-1,2-naphthoquinone 
• 74634-34-7 6-bromonaphthalen-2-yl benzoate 
• 18768-91-7 6-triphenylsilanyl-[2]naphthol 
• 202831-66-1 6-bromo-N-phenylnaphthalene-2-amine 

Relevant articles and documents

Chiral phosphoric acid catalyzed asymmetric addition of naphthols to para -quinone methides

An asymmetric addition of naphthols to in situ generated para-quinone methides catalyzed by a chiral phosphoric acid is described. A range of useful triarylmethanes can be generated from stable general para-hydroxybenzyl alcohols with good efficiency and enantioselectivity.

Reductive dehalogenation of halophenols in sulfite-bisulfate medium

The KHSO4-Na2SO3 system is found to be simple and inexpensive for reductive elimination of halogens (Br, I) from the corresponding halophenols under reflux conditions in dry methanol. Under similar conditions the reaction is sluggish with chlorophenols.

Pyrene based conjugated materials: Synthesis, characterization and electroluminescent properties

In this work, three novel pyrene cored small conjugated molecules, namely 1,3,6,8-tetrakis(6-(octyloxy)naphthalene-2-yl)pyrene (PY-1), 1,3,6,8-tetrakis((E)-2-(6-(n-octyloxy)naphthalene-2-yl)vinyl)pyrene (PY-2) and 1,3,6,8-tetrakis((6-(n-octyloxy)naphthalene-2-yl)ethynyl)pyrene (PY-3) have been synthesized by Suzuki, heck and Sonogashira organometallic coupling reactions, respectively. The effects of single, double and triple bonds on their optical, electrochemical, and thermal properties are studied in detail. These are all materials fluorescent and they have been used in organic light-emitting diodes (OLEDs) and their electroluminescent properties have been studied. This journal is

Synthesis and antitumor effects of novel benzyl naphthyl sulfoxide/sulfone derivatives derived from Rigosertib

In this work, a series of novel benzyl naphthyl sulfoxides/sulfones derived from Rigosertib were designed and synthesized as potential antitumor agents. The in vitro cytotoxicity against four human cancer cell lines (HeLa, MCF-7, HepG2 and SCC-15) and two normal human cell lines (HUVEC and 293T) indicated that some of the sulfones and sulfoxides possessed potent antineoplastic activity that reached nanomolar levels and relatively low toxicity to normal cells. Among them, (2-methoxy-5-((naphthalen-2-ylsulfonyl)methyl)phenyl)glycine (15b) was found to be a promising antitumor drug candidate that could significantly inhibit tumor cell migration and induce tumor cell apoptosis via the p53-Bcl-2-Bax signaling pathway at nanomolar concentrations.

Synthesis and radioprotective effects of novel benzyl naphthyl sulfoxide (sulfone) derivatives transformed from Ex-RAD

In this work, a series of novel benzyl naphthyl sulfoxides (sulfones) derived from Ex-RAD were designed and synthesized as potential radioprotective agents. Some of the compounds considerably protected HUVECs against 60Co γ-irradiation, accompanied by the absence of cytotoxicity. Compared to Ex-RAD, compound 8n not only exhibited a significant protective effect on cell survival and radiation-induced DNA damage, but also remarkably enhanced the survival (100%) of mice in 30 days after being exposed to irradiation. The results suggested that some target compounds are valuable for further research as promising radioprotectors.

NAPHTHALENE-CONTAINING POLYMERS AND METHODS OF MAKING THE SAME

The present disclosure relates to a dimer that includes a first hydroxyl-functionalized naphthalene group and a second hydroxyl-functionalized naphthalene group, where the first hydroxyl-functionalized naphthalene group and the second hydroxyl-functionalized naphthalene group are connected by a bridging group. The present disclosure also relates to a polymer synthesized using the dimer, as well as methods for synthesizing both the dimer and the polymer.

Process for synthesizing 6-bromo-2-naphthol

The invention relates to a process for synthesizing 6-bromo-2-naphthol. The process comprises the following steps: (S1) mixing 2-naphthol and a bromo salt, and adding the mixture into a reactor; (S2) adding an acetic solution into the reactor in the step (S1); (S3) dropwise adding an oxidant into the reactor while carrying out stirring, and carrying out a heat-insulating reaction after dropwise adding is completed, so as to obtain an intermediate solution; (S4) heating the temperature of the reactor to a definite value, adding nano Pd/Fe into the intermediate solution obtained in the step (S3), introducing nitrogen gas into the reactor, and carrying out a reaction while controlling the temperature and pressure to definite values; (S5) cooling the reactor, adding pure water into the reactor in the step (S4) for dilution, and carrying out standing for a period of time for crystallization; and (S6) subjecting the crystals obtained in the step (S5) to filtering and washing, adding the crystals into an acetic solution for recrystallization, and subjecting the recrystallized crystals to filtering, washing and drying, thereby obtaining a finished product. According to the process, on one hand, the utilization ratio of atoms is increased, and large-area pollution to environments caused by reactions is prevented; and on the other hand, the requirements of a reaction process on public works are relatively low, the reaction rate is relatively high, and the purity and yield of the obtained final product are relatively high, so that the process is applicable to industrial mass production.

A conjugated system of curcumin analogs increase and its preparation method and application

The invention discloses a curcumin analogue with an enlarged conjugated system and a preparation method and application thereof. The structural feature of the curcumin analogue is shown in the general formula (I), wherein R1 is hydrogen and methoxyl, R2 is hydrogen, hydroxy and methoxyl, and two naphthalene nucleuses are connected through a 1,6-heptadiene-3,5-diketone joining chain. The naphthol is used as a raw material, the naphthalene nucleus curcumin analogue with the superior activity for hepatoma carcinoma cell HepG2 cell proliferation is synthesized, and the activity of the curcumin analogue is superior to that of natural curcumin. The curcumin analogue with the enlarged conjugated system has the great significance in guiding discovery of prodrugs and designing lead compounds.

Synthesis and cytotoxicity of n-substituted dibenzo[a,j]xanthene-3,11-dicarboxamide derivatives

In order to study the structure-activity relationships of xanthene derivatives, four series of N-substituted 14-aryl-14H-dibenzo[a,j]xanthene-3,11-dicarboxamide derivatives were synthesized. The structures of all compounds were identified by 1H-NMR HR-MS and IR spectra in which compounds 6a-h were further identified by 13C-NMR spectra. The in vitro antitumor activity of the synthesized compounds was tested by MTT assay. Most of them displayed strong inhibitory activity on human hepatocellular carcinoma cell lines (SK-HEP-1 HepG2 and SMMC-7721 cells) and acute promyelocytic leukemia NB4 cells. Compounds 6c-6e exhibited significant inhibitory activity against NB4 cells with IC50 values of 0.52 μM and 0.76 μM respectively much lower than 5.31 μM of the positive control As2O3.

Ene Reductase Enzymes for the Aromatisation of Tetralones and Cyclohexenones to Naphthols and Phenols

Ene reductases (EREDs) have great potential as oxidation biocatalysts, as demonstrated by their efficient conversion of a number of tetralones to the corresponding naphthols. Of 96 enzymes tested, 57 were able to produce 2-naphthol in this way. Further tests with substituted tetralones revealed typically high conversions up to >99%. The reactions were performed under mild conditions in aqueous buffer with only co-solvent, biocatalyst and oxidation substrate required for conversion. Production of a methoxy-substituted naphthol was also successfully performed on a gram scale, with 91% yield. This methodology provides a new avenue to produce substituted naphthols as valuable building blocks, with the possibility to extend the approach to the production of phenols also being demonstrated.