| Identification | More | [Name]
1-BROMO-2-NAPHTHOIC ACID | [CAS]
20717-79-7 | [Synonyms]
1,2-BNCA
Einecs 243-984-9
RARECHEM AL BE 0298
1-BroMo-2-phthoic acid
1-BROMO-2-NAPTHOIC ACID
1-Bromo-2-naphtoic acid
1-BROMO-2-NAPHTHOIC ACID
1-Bromo-2-naphthoic Acid >
1-bromonaphthalene-2-carboxylicaci
1-BROMO-2-NAPHTHALENECARBOXYLIC ACID
1-Bromonaphthalene-2-carboxylic acid
1-bromo-2-naphthoic acid crystalline
2-Naphthalenecarboxylicacid, 1-bromo- | [EINECS(EC#)]
243-984-9 | [Molecular Formula]
C11H7BrO2 | [MDL Number]
MFCD00021408 | [Molecular Weight]
251.08 | [MOL File]
20717-79-7.mol |
| Chemical Properties | Back Directory | [Melting point ]
191 °C | [Boiling point ]
372.7±25.0 °C(Predicted) | [density ]
1.648 | [storage temp. ]
Sealed in dry,Room Temperature | [form ]
Powder or Crystalline Powder | [pka]
2.85±0.30(Predicted) | [color ]
White to yellow to light brown | [InChI]
InChI=1S/C11H7BrO2/c12-10-8-4-2-1-3-7(8)5-6-9(10)11(13)14/h1-6H,(H,13,14) | [InChIKey]
VUVIRKAVBZITDO-UHFFFAOYSA-N | [SMILES]
C1(Br)=C2C(C=CC=C2)=CC=C1C(O)=O | [CAS DataBase Reference]
20717-79-7(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Chemical Properties]
Solid | [Uses]
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.
| [Synthesis]
4) 1.59 g of 2-hydroxymethyl-1-bromonaphthalene and 22 mL of acetone were added to a 250 mL round bottom flask and heated to reflux. 3.67 g of potassium permanganate was dissolved in 8.1 mL of water and 55 mL of acetone, heated and slowly added to the round-bottomed flask, and the reaction mixture was maintained at reflux for 30 min, then continued at reflux for 5 hr. The solution gradually turned brown during the reaction and the heating was stopped when the reaction was completed. The reaction mixture was filtered to remove the resulting MnO2 solid precipitate and the precipitate was washed with ether. Concentration of the filtrate gave 1.32 g of the target product 1-bromo-2-naphthoic acid in 78.6% yield. | [References]
[1] Patent: CN105541605, 2016, A. Location in patent: Paragraph 0017; 0026; 0035; 0044; 0071; 0080
[2] Journal of Organic Chemistry, 1983, vol. 48, # 21, p. 3869 - 3876 |
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