2-Naphthalenecarboxylic acid, 6-bromo-, methyl ester
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2-Naphthalenecarboxylic acid, 6-bromo-, methyl ester
structure -
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CAS No:
33626-98-1
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Formula:
C12H9BrO2
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Chemical Name:
2-Naphthalenecarboxylic acid, 6-bromo-, methyl ester
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Synonyms:
2-Naphthalenecarboxylic acid,6-bromo-,methyl ester;2-Naphthoic acid,6-bromo-,methyl ester;Methyl 6-bromonaphthalene-2-carboxylate;Methyl 6-bromo-2-naphthoate;6-Bromonaphthalene-2-carboxylic acid methyl ester;2-Bromo-6-methoxycarbonylnaphthalene;Methyl 6-(3-benzyl-4-((2-methoxyethoxy)methoxy)phenyl)-2-naphthoate
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CAS No:
2-Naphthalenecarboxylic acid, 6-bromo-, methyl ester Basic Attributes
265.1
265.10
2578943
-0
47YX2K4GR3
DTXSID50357551
2916399090
Characteristics
26.3
3.7
Off-white to cream or light brown Crystalline Powder
1.5±0.1 g/cm3
125-127 °C
357°C at 760 mmHg
169.7±20.4 °C
1.635
Safety Information
NONH for all modes of transport
3
20/21/22-34
24/25-45-36/37/39-27-26
C
P264, P273, P280, P302+P352, P321, P332+P313, P362, P501
H315
|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P264, P273, P280, P302+P352, P321, P332+P313, P362, and P501|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
2-Naphthalenecarboxylic acid, 6-bromo-, methyl ester Use and Manufacturing
6-Bromo-2-naphthalenecarboxylic acid (2.4996 g, 10.0 mmol) was added50mL dried egg-shaped flask, add 20mL of anhydrous methanol to dissolve, Then 1 mL of concentrated sulfuric acid was slowly added dropwise and the system was refluxed overnight.TLC tracking until the conversion of raw materials is completed, stop heating, After cooling to room temperature, saturated aqueous sodium carbonate solution was added to quench the reaction.The reaction system was adjusted to neutrality, extracted with ethyl acetate, The organic phase is washed three times with anhydrous sodium sulfate.Concentration under reduced pressure afforded S7 (2.63 g, 100percent yield) as a white solid.To a solution of 6-bromo-2-naphthoic acid (2.65 g, 10 mmol) in methanol 30 mL, concentrated sulfuric acid 1 mL was added drop wise. The reaction mixture was refluxed for 2 h, then added water 150 mL. The foliated crystal was collected thought filtration. Yield: 93percent;Reactor to 6-bromo-2-naphthalene carboxylic acid (T-1, manufactured by Tokyo Kasei Kogyo (Ltd.)) (25g, 99.6mmol), concentrated sulfuric acid (5.4ml, 99.6mmol), and methanol (80ml) It was placed. The mixture was stirred with heating under reflux for 7 hours. After cooling to room temperature, water was added to the reaction mixture and extracted with dichloromethane. Aqueous organic layers were washed with sodium carbonate, washed with water, then saturated brine, and dried over anhydrous magnesium sulfate. By concentrating the solution under reduced pressure to give compound (T-2) (26.4g, 99.6mmol) and. Compound (T-2) was used in the next reaction without purification.
Methyl 6-Bromo-2-napthoate is used in the synthesis of Adapalene, a retinoid specific for RARβ and RARγ receptors.
Computed Properties
Molecular Weight:265.10
XLogP3:3.7
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:263.97859
Monoisotopic Mass:263.97859
Topological Polar Surface Area:26.3
Heavy Atom Count:15
Complexity:242
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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