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

Chemical Properties

Solid

Uses

Different sources of media describe the Uses of 20717-79-7 differently. You can refer to the following data:
1. Reactant involved in synthesis of:Binaphthyl-based amino acids and amino alcohols via domino coupling reactions and lactam ring opening of intermediatesBenzimidazoles and benzimidazolequinone derivatives via cyclocondensationAxially chiral biaryls via Suzuki-Miyaura reactionsAryl ring-fused benzimidazolequinones via radical cyclizationProbes for human cytochrome P450 enzymesPhananthridinone derivatives via domino coupling reactions
2. 1-Bromo-2-naphthoic acid is a reactant involved in synthesis of:? ;Binaphthyl-based amino acids and amino alcohols via domino coupling reactions and lactam ring opening of intermediates? ;Benzimidazoles and benzimidazolequinone derivatives via cyclocondensation? ;Axially chiral biaryls via Suzuki-Miyaura reactions? ;Aryl ring-fused benzimidazolequinones via radical cyclization? ;Probes for human cytochrome P450 enzymes? ;Phananthridinone derivatives via domino coupling reactions.

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 
• 2586-62-1 1-bromo-2-methylnaphtalene 
• 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 
• 91-57-6 2-Methylnaphthalene 
• 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 

Downstream Products

• 138435-68-4 3,5-diisopropylphenyl 1-bromo-2-naphthoate 
• 89555-39-5 methyl 1-bromo-2-naphthalenecarboxylate 

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.