947-62-6

Basic information

• Product Name: 2-METHOXY-1-NAPHTHOIC ACID
• Synonyms: 2-METHOXYNAPHTHOIC ACID;2-METHOXY-1-NAPHTHOIC ACID;AKOS 243-07;RARECHEM AL BO 1095;2-METHOXY-1-NAPHTOIC ACID;2-methoxynaphthalene-1-carboxylic acid
• CAS NO: 947-62-6
• Molecular Formula: C₁₂H₁₀O₃
• Molecular Weight: 202.21
• EINECS: 213-429-5
• Product Categories: Building Blocks;C11 to C12;Carbonyl Compounds;Carboxylic Acids;Chemical Synthesis;Organic Building Blocks
• Mol File: 947-62-6.mol
• Article Data: 14

Chemical Properties

• Melting Point: 177-180 °C(lit.)
• Boiling Point: 390.2°Cat760mmHg
• Flash Point: 156.5°C
• Appearance: /Solid
• Density: 1.263g/cm³
• Vapor Pressure: 8.67E-07mmHg at 25°C
• Refractive Index: 1.64
• PKA: 3.11±0.10(Predicted)
• CAS DataBase Reference: 2-METHOXY-1-NAPHTHOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-METHOXY-1-NAPHTHOIC ACID(947-62-6)
• EPA Substance Registry System: 2-METHOXY-1-NAPHTHOIC ACID(947-62-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 947-62-6(Hazardous Substances Data)

Usage

Uses

2-Methoxy-1-naphthoic acid may be used in the synthesis of chiral (methoxynaphthyl)oxazoline.

General Description

2-Methoxy-1-naphthoic acid is the 3-methoxy derivative of 1-napthoic acid. It can be prepared from a Grignard reagent derived from 1-bromo-2-methoxynaphthalene. 2-Methoxy-1-naphthoic acid undergoes Birch reduction to afford 2-methoxy-1,4,5,8-tetrahydro-1-naphthoic acid.

InChI:InChI=1/C12H10O3/c1-15-10-7-6-8-4-2-3-5-9(8)11(10)12(13)14/h2-7H,1H3,(H,13,14)

Upstream product

• 109-72-8 n-butyllithium 
• 3401-47-6 1-bromo-2-methoxynaphthalene 
• 5392-12-1 2-methoxy-1-naphthaldehyde 
• 77-78-1 dimethyl sulfate 
• 2283-08-1 2-hydroxy-1-naphthalenecarboxylic acid 
• 124-38-9 carbon dioxide 
• 32721-21-4 1-iodo-2-methoxynapthalene 
• 141-82-2 malonic acid 
• 93-04-9 2-Methoxynaphthalene 
• 74-88-4 methyl iodide 
• 145117-62-0 1-naphthoyloxyl radical 
• 13101-92-3 1-chloro-2-methoxynaphthalene 
• 708-06-5 2-hydroxynaphthalene-1-carbaldehyde 
• 858199-99-2 (2-methoxy-[1]naphthyl)-glyoxylic acid 

Downstream Products

• 93-04-9 2-Methoxynaphthalene 
• 135-19-3 β-naphthol 
• 78594-16-8 2-methoxy-1-(phenylethynyl)naphthalene 
• 1415045-77-0 N,N-diethyl-2-phenyl-1-naphthamide 
• 1415046-43-3 2-phenyl-6-(4-methoxyphenyl)-N,N-dimethyl-1-naphthamide 
• 1415046-44-4 2-phenyl-6-(4-methoxyphenyl)-N,N-diethyl-1-naphthamide 
• 1415046-41-1 2-methoxy-6-(4-methoxyphenyl)-N,N-dimethyl-1-naphthamide 
• 1415046-42-2 2-methoxy-6-(4-methoxyphenyl)-N,N-diethyl-1-naphthamide 
• 13101-92-3 1-chloro-2-methoxynaphthalene 
• 108981-94-8 2-phenyl-1-naphthalenecarboxylic acid 
• 855261-19-7 [2,2'-binaphthalene]-1-carboxylic acid 
• 16000-39-8 1-cyano-2-methoxynaphthalene 
• 5111-65-9 2-Bromo-6-methoxynaphthalene 
• 15231-91-1 6-bromo-naphthalen-2-ol 

Relevant articles and documents

6,7-Dimethoxy-2-phenethyl-1,2,3,4-tetrahydroisoquinoline amides and corresponding ester isosteres as multidrug resistance reversers

Aiming to deepen the structure–activity relationships of the two P-glycoprotein (P-gp) modulators elacridar and tariquidar, a new series of amide and ester derivatives carrying a 6,7-dimethoxy-2-phenethyl-1,2,3,4-tetrahydroisoquinoline scaffold linked to different methoxy-substituted aryl moieties were synthesised. The obtained compounds were evaluated for their P-gp interaction profile and selectivity towards the two other ABC transporters, multidrug-resistance-associated protein-1 and breast cancer resistance protein, showing to be very active and selective versus P-gp. Two amide derivatives, displaying the best P-gp activity, were tested in co-administration with the antineoplastic drug doxorubicin in different cancer cell lines, showing a significant sensitising activity towards doxorubicin. The investigation on the chemical stability of the derivatives towards spontaneous or enzymatic hydrolysis, showed that amides are stable in both models while some ester compounds were hydrolysed in human plasma. This study allowed us to identify two chemosensitizers that behave as non-transported substrates and are characterised by different selectivity profiles.

Decarbonylative halogenation by a vanadium complex

Metal-catalyzed halogenation of the C-H bond and decarbonylation of aldehyde are conventionally done in nature. However, metal-mediated decarbonylative halogenation is unknown. We have developed the first metal-mediated decarbonylative halogenation reaction starting from the divanadium oxoperoxo complex K3V5+2(O 22-)4(O2-)2(μ-OH) (1). A concerted decarbonylative halogenation reaction was proposed based on experimental observations.

Metalation of 2-heterosubstituted naphthalenes at the 1- or 3- position: Factors that may determine the regiochemistry

Upon metalation and subsequent electrophilic trapping, 2-fluoronaphthalene inevitably gives rise to regioisomeric mixtures in varying proportions, whereas 2-(trifluoromethyl)naphthalene undergoes deprotonation either at the 1- or the 3-position, depending on the choice of the reagent. On the other hand, 2-(trifluo-romethoxy)naphthalene and 2-methoxynaphthalene react exclusively at the 3-position when, respectively, sec-butylhthium and superbasic reagents are employed. Steric repulsion by the peri hydrogen in combination with crowding due to coordination of the lithium atom with the methoxy group disfavors attack at the 1-position. Georg Thieme Verlag Stuttgart.