103143-23-3

Basic information

• Product Name: Naphthalene, 2-(bromomethyl)-7-methoxy-
• CAS NO: 103143-23-3
• Molecular Formula: C12H11BrO
• Mol File: 103143-23-3.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Naphthalene, 2-(bromomethyl)-7-methoxy-(CAS DataBase Reference)
• NIST Chemistry Reference: Naphthalene, 2-(bromomethyl)-7-methoxy-(103143-23-3)
• EPA Substance Registry System: Naphthalene, 2-(bromomethyl)-7-methoxy-(103143-23-3)

Safety Data

• Hazardous Substances Data: 103143-23-3(Hazardous Substances Data)

Upstream product

• 5665-20-3 20(hydroxymethyl)-7-methoxynaphthalene 
• 72775-48-5 7-methoxynaphthalene-2-carboxylic acid ethyl ester 
• 135653-94-0 7-methoxy-2-trifluoromethanesulfonyloxynaphthalene 
• 5060-82-2 7-methoxy-2-naphthol 
• 1131-53-9 2-methoxy-7-methylnaphthalene 

Downstream Products

• 72907-96-1 2-ethoxalyl-8-methoxy-1-oxo-2,3-dihydro-1H-cyclopentanaphthalene 
• 72907-97-2 2-(carbethoxymethyl)-8-methoxy-1-oxo-2,3-dihydro-1H-cyclopentanaphthalene 
• 72907-99-4 2-(carbethoxymethyl)-8-hydroxy-1-oxo-2,3-dihydro-1H-cyclopentanaphthalene 
• 72908-00-0 2-(carbamylmethyl)-8-hydroxy-1-oxo-2,3-dihydro-1H-cyclopentanaphthalene 
• 72908-01-1 2-(carbamylmethyl)-8-hydroxy-3H-cyclopenta[a]naphthalene 
• 5665-25-8 2-(β-carboxyethyl)-7-methoxynaphthalene 
• 5670-11-1 8-methoxy-1-oxo-2,3-dihydro-1H-cyclopentanaphthalene 
• 3451-02-3 benzene-1,2,3,4-tetracarboxylic acid tetramethyl ester 

Relevant articles and documents

A rationally designed prototype of a molecular motor

A proof of principle of the first rationally designed, chemically powered, molecular-scale motor is described. The thermodynamic considerations leading to the choice of 6a and 7a as the initial prototypes are provided, and the synthesis of 6a and 7a and the separation of them from their atropisomers are detailed. The phosgene-powered unidirectional rotation of 6a to its rotamer 6b is demonstrated. It is further established that shortening the length of the tether (→7a) changes the rate-limiting step and accelerates the speed of rotation.

New cyclopenta[a]naphthalene derivatives: Synthesis of 2-(carbamylmethyl)-8-hydroxy-3H-cyclopenta[a]naphthalene as a possible deoxyribonucleic acid binding agent

8-Methoxy-1-oxo-2,3-dihydro-1H-cyclopental[a]naphthalene (4) was converted to the oxalyl derivative (7) by treatment with diethyl oxalate in the presence of sodium ethoxide. Compound 7 in the form of the sodium salt was alkylated with ethyl bromoacetate in DMF to 2-(carbethoxymethyl)-8-methoxy-1-oxo-2,3-dihydro-1H-cyclopenta[a]naphthalene (8). Treatment of 8 with methanolic ammonia yielded the corresponding amide (9). Dealkylation of 8 with 48% HBr and subsequent esterification gave compound 10. Ammonolysis of 10 led to the amide 11, which after reduction and subsequent dehydration of the reduced product afforded the desired compound, 2-(carbamylmethyl)-8-hydroxy-3H-cyclopenta[a]naphthalene (2). Compound 2 was found to be mildly growth inhibitory to L1210 and CCRF-CEM leukemic cells in culture. From thermal transition temperature studies, compound 2 was found to bind to calf thymus DNA and the poly(deoxyribonucleotides), e.g., poly(dG)-poly(dC), poly(dG-dC), poly(dA)-poly(dT), and poly (dA-dT).