20717-79-7

Basic information

• Product Name: 1-BROMO-2-NAPHTHOIC ACID
• Synonyms: 1-BROMO-2-NAPHTHALENECARBOXYLIC ACID;1-BROMO-2-NAPHTHOIC ACID;1-BROMO-2-NAPTHOIC ACID;1-bromo-2-naphthoic acid crystalline;1-Bromo-2-naphtoic acid;Einecs 243-984-9;1-BroMo-2-phthoic acid;1,2-BNCA
• CAS NO: 20717-79-7
• Molecular Formula: C₁₁H₇BrO₂
• Molecular Weight: 251.08
• EINECS: 243-984-9
• Product Categories: Building Blocks;C11 to C12;Carbonyl Compounds;Carboxylic Acids;Chemical Synthesis;Organic Building Blocks
• Mol File: 20717-79-7.mol
• Article Data: 17

Chemical Properties

• Melting Point: 191 °C
• Boiling Point: 372.7 °C at 760 mmHg
• Flash Point: 179.2 °C
• Appearance: White to yellow to light brown/Powder or Crystalline Powder
• Density: 1.648
• Vapor Pressure: 3.24E-06mmHg at 25°C
• Refractive Index: 1.697
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 2.85±0.30(Predicted)
• CAS DataBase Reference: 1-BROMO-2-NAPHTHOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 1-BROMO-2-NAPHTHOIC ACID(20717-79-7)
• EPA Substance Registry System: 1-BROMO-2-NAPHTHOIC ACID(20717-79-7)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 20717-79-7(Hazardous Substances Data)

Usage

Description

1-Bromo-2-naphthoic acid is an organic compound that features a naphthalene ring with a bromine atom and a carboxylic acid group. It is a solid with chemical properties that make it a versatile reactant in various organic synthesis processes.

Uses

Used in Pharmaceutical and Chemical Industries:
1-Bromo-2-naphthoic acid is used as a reactant for the synthesis of Binaphthyl-based amino acids and amino alcohols via domino coupling reactions and lactam ring opening of intermediates. This application is crucial for the development of chiral molecules with potential pharmaceutical applications.
Used in Heterocyclic Chemistry:
1-Bromo-2-naphthoic acid is used as a reactant for the synthesis of Benzimidazoles and Benzimidazolequinone derivatives via cyclocondensation. These heterocyclic compounds are important in the development of pharmaceuticals, agrochemicals, and other organic compounds.
Used in Chiral Compounds Synthesis:
1-Bromo-2-naphthoic acid is used as a reactant for the synthesis of Axially chiral biaryls via Suzuki-Miyaura reactions. Axially chiral biaryls are valuable building blocks in the creation of enantioselective catalysts and ligands.
Used in Organic Synthesis:
1-Bromo-2-naphthoic acid is used as a reactant for the synthesis of Aryl ring-fused benzimidazolequinones via radical cyclization. These compounds have potential applications in various fields, including materials science and medicinal chemistry.
Used in Enzyme Research:
1-Bromo-2-naphthoic acid is used as a reactant for the synthesis of Probes for human cytochrome P450 enzymes. These probes are essential for studying enzyme activity and understanding the metabolism of various compounds.
Used in Organic Synthesis:
1-Bromo-2-naphthoic acid is used as a reactant for the synthesis of Phananthridinone derivatives via domino coupling reactions. These derivatives have potential applications in the development of novel organic compounds and materials.

InChI:InChI=1/C11H7BrO2/c12-10-8-4-2-1-3-7(8)5-6-9(10)11(13)14/h1-6H,(H,13,14)

Upstream product

• 3378-82-3 1-bromo-2-naphthaldehyde 
• 91-57-6 2-Methylnaphthalene 
• 117582-62-4 1-bromo-2-formyl-3,4-dihydronaphthalene 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 87262-94-0 1-bromo-2-(acetoxymethyl)naphthalene 
• 37763-43-2 1-bromo-2-(bromomethyl)naphthalene 
• 127349-02-4 1-bromo-2-(dibromomethyl)naphthalene 
• 20176-08-3 1-bromo-2-naphthalenyl-2-carbonitrile 
• 76635-70-6 (1-bromo-2-naphthyl)methanol 
• 2586-62-1 1-bromo-2-methylnaphtalene 

Downstream Products

• 89555-39-5 methyl 1-bromo-2-naphthalenecarboxylate 
• 1221726-55-1 1-bromo-N-(4-methoxybenzyl)-2-naphthamide 
• 1221726-56-2 3-(p-methoxybenzyl)dibenzo[a,k]phenanthridin-4(3H)-one 
• 129667-82-9 phenyl 1-bromo-2-naphthoate 

Relevant articles and documents

Synthesis and cytotoxic activity of acronycine analogues in the benzo[c]pyrano[3,2-h]acridin-7-one and naphtho[1,2-b][1,7] and [1,10]-phenanthrolin-7(14H)-one series

Condensation of 1-bromo-2-naphthalenecarboxylic acid (9) with 7-methoxy-2,2-dimethyl-2H-1-benzopyran-5-ylamine (13) followed by acid-mediated cyclization afforded 6-methoxy-3,3-dimethyl-3,14-dihydro-7H-benzo[c]pyrano[3,2- h]acridin-7-one (15), which was further methylated into 6-methoxy-3,3,14- trimethyl-3,14-dihydro-7H-benzo[c]pyrano[3,2-h]acridin-7-one (benzo[c]acronycine) (3) and 6,7-dimethoxy-3,3-dimethyl-3H-benzo[c]pyrano[3,2-h] acridine (4). Osmium tetroxide oxidation of 15 gave the (±)-cis-diol 16, which afforded the benzopyranoacridine and benzopyranoacridone esters 17-22 upon acylation. Condensation of 9 with suitable aminoquinolines 23-25 afforded the carboxylic naphthylquinolylamines 26-28. Cyclization gave the corresponding naphtho[1,2-b][1,10]-phenanthrolin-7(14H)-ones 29 and 30, and naphtho[1,2-b][1,7]-phenanthrolin-7(14H)-one 31, which were subsequently N-methylated to the desired 14-methylnaphtho[1,2-b][1,10] and [1,7]-phenanthrolinones 6, 7, and 8. Benzo[c]pyrano[3,2-h]acridin-7-one derivatives 3, 16, and 22 displayed cytotoxic activities within the same range of magnitude as acronycine itself, whereas 7-alkoxybenzo[c]pyrano[3,2-h]acridine and 7-acyloxybenzo[c]pyrano[3,2-h]acridine derivatives 4 and 17-21 were less active when tested against L1210 murine leukemia cells in vitro. Naphthophenanthrolinones 6-8 were devoid of significant antiproliferative activity, but compounds 29-31 bearing no substituent on the nitrogen atom at position 14 were more potent.

Synthesis method of benzoic acid compounds

The invention discloses a photocatalytic oxidation synthesis method of benzoic acid compounds, and the photocatalytic oxidation synthesis method comprises the following specific steps: mixing and dissolving toluene compounds and a catalyst in a solvent, reacting for 24-60h in the presence of an oxidant under the conditions of 350-460 nm LED illumination and a temperature of 20-80 DEG C, and performing post-treatment on the reaction liquid to obtain the benzoic acid compounds. The photocatalytic oxidation synthesis method has the advantages of no need of metal catalysts, simple operation and mild reaction conditions; oxygen is used as an oxidant, and the photocatalytic oxidation synthesis method has high atom economy, cheap reagent and environmental protection. The photocatalytic oxidationsynthesis method has good substrate applicability, and various substituents can realize the synthesis of corresponding benzoic acid compounds.

Atropoenantioselective Redox-Neutral Amination of Biaryl Compounds through Borrowing Hydrogen and Dynamic Kinetic Resolution

We report herein a novel atropoenantioselective redox-neutral amination of biaryl compounds triggered by a cascade of borrowing hydrogen and dynamic kinetic resolution under the cooperative catalysis of a chiral iridium complex and an achiral Br?nsted acid. This protocol features broad substrate scope and good functional-group tolerance, and allows the rapid assembly of axially chiral biaryl compounds in good to high yields and with high to excellent enantioselectivity.