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6-Methoxy-2-Naphthaldehyde
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Name

6-Methoxy-2-Naphthaldehyde

 EINECS 222-377-2
CAS No. 3453-33-6 Density 1.169 g/cm3
PSA 26.30000 LogP 2.66090
Solubility 150.1mg/L at 25℃ Melting Point 80-82 °C
Formula C12H10O2 Boiling Point 340.2 °C at 760 mmHg
Molecular Weight 186.21 Flash Point 162.7 °C
Transport Information N/A Appearance Slightly yellow crystalline powder
Safety 26-36-24/25-37/39 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 3453-33-6 (6-Methoxy-2-naphthaldehyde) Hazard Symbols IrritantXi
Synonyms

2-Naphthaldehyde,6-methoxy- (6CI,7CI,8CI);2-Methoxy-6-naphthalenecarboxaldehyde;6-Methoxy-2-naphthalenecarboxaldehyde;MONAL 62;6-Methoxy-2-naphthaldehyde;

Article Data 67

6-Methoxy-2-Naphthaldehyde Synthetic route

5111-65-9

2-Bromo-6-methoxynaphthalene

68-12-2, 33513-42-7

N,N-dimethyl-formamide

3453-33-6

6-methoxynaphthalene-2-carbaldehyde

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃;97%
Stage #1: 2-Bromo-6-methoxynaphthalene With n-butyllithium In tetrahydrofuran
Stage #2: N,N-dimethyl-formamide		90%
Stage #1: 2-Bromo-6-methoxynaphthalene With n-butyllithium In tetrahydrofuran; cyclohexane at -78℃; for 0.25h;
Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; cyclohexane at -78℃; for 0.25h; Further stages.;		74%
60201-22-1

(6-methoxy-2-naphthyl)methanol

3453-33-6

6-methoxynaphthalene-2-carbaldehyde

Conditions
ConditionsYield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In water; acetic acid for 4h; Heating;95%
With 1-hydroxy-1H-1,2,3-benziodoxathiole 1,3,3-trioxide; Oxone; cetyltrimethylammonim bromide In water at 20℃; for 2h; Green chemistry; chemoselective reaction;95%
With pyridinium chlorochromate In dichloromethane at 20℃;
92190-49-3

(6-methoxynaphthalene-2-yl)methyl acetate

3453-33-6

6-methoxynaphthalene-2-carbaldehyde

Conditions
ConditionsYield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In water; acetic acid for 4h; Heating;95%

C13H13N3O2

3453-33-6

6-methoxynaphthalene-2-carbaldehyde

Conditions
ConditionsYield
With (Bu4N)2S2O8 In 1,2-dichloro-ethane at 80℃; for 0.6h; oxidative cleavage;94%
201230-82-2

carbon monoxide

5111-65-9

2-Bromo-6-methoxynaphthalene

3453-33-6

6-methoxynaphthalene-2-carbaldehyde

Conditions
ConditionsYield
With N,N,N,N,-tetramethylethylenediamine; hydrogen; palladium diacetate; propyl di-tert-butylphosphinite In toluene at 100℃; under 3750.38 Torr; for 20h; Inert atmosphere;93%
With N,N,N,N,-tetramethylethylenediamine; hydrogen; palladium diacetate; catacxium A In toluene at 120℃; under 9000.9 Torr; Flow reactor; Green chemistry;84%
With 4-methoxy-N'-tetramethylethylenediamine; hydrogen; catacxium A; palladium diacetate In toluene at 100℃; under 3750.3 Torr; for 16h;99 % Chromat.
With N,N,N,N,-tetramethylethylenediamine; hydrogen; catacxium A; palladium diacetate In toluene at 100℃; under 3750.38 Torr; for 16h;99 % Chromat.
26386-94-7

2-methyl-6-methoxynaphthalene

3453-33-6

6-methoxynaphthalene-2-carbaldehyde

Conditions
ConditionsYield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In water; acetic acid for 5h; Heating;90%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In water; acetic acid for 4h; Heating;90%
201230-82-2

carbon monoxide

C11H9FO4S

3453-33-6

6-methoxynaphthalene-2-carbaldehyde

Conditions
ConditionsYield
With pyridine; 1,3-bis-(diphenylphosphino)propane; hydrogen; palladium diacetate In dimethyl sulfoxide at 120℃; under 7500.75 Torr; for 2h; Flow reactor;90%
5111-65-9

2-Bromo-6-methoxynaphthalene

3453-33-6

6-methoxynaphthalene-2-carbaldehyde

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; N,N-dimethyl-formamide at -78 - 20℃; for 2h; Inert atmosphere;88.6%
With n-butyllithium In tetrahydrofuran; hexane; N,N-dimethyl-formamide
With magnesium; acetic acid In tetrahydrofuran; N,N-dimethyl-formamide

oxime of 6-methoxy-2-naphthyl aldehyde

3453-33-6

6-methoxynaphthalene-2-carbaldehyde

Conditions
ConditionsYield
With (Bu4N)2S2O8 In 1,2-dichloro-ethane for 1.5h; Heating;87.5%
50-00-0

formaldehyd

5111-65-9

2-Bromo-6-methoxynaphthalene

3453-33-6

6-methoxynaphthalene-2-carbaldehyde

Conditions
ConditionsYield
With triethylsilane; dichloro bis(acetonitrile) palladium(II); sodium carbonate; 1,4-di(diphenylphosphino)-butane In N,N-dimethyl-formamide at 20 - 100℃; under 15001.5 Torr; for 20h; Inert atmosphere; Autoclave;61%

6-Methoxy-2-Naphthaldehyde Specification

The 6-Methoxy-2-Naphthaldehyde is an organic compound with the formula C12H10O2. The IUPAC name of this chemical is 6-methoxynaphthalene-2-carbaldehyde. With the CAS registry number 3453-33-6 and EINECS 222-377-2, it is also named as 2-naphthalenecarboxaldehyde, 6-methoxy-. The product's categories are Aromatic Aldehydes & Derivatives (substituted); Aldehydes; C10 to C21; Carbonyl Compounds. It is slightly yellow crystalline powder which is stable under normal temperature and pressure. Additionally, this chemical should be sealed in the container and stored in the cool and dry place.

Physical properties about 6-Methoxy-2-Naphthaldehyde are: (1)ACD/LogP: 2.63; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.63; (4)ACD/LogD (pH 7.4): 2.63; (5)ACD/BCF (pH 5.5): 58.72 ; (6)ACD/BCF (pH 7.4): 58.72; (7)ACD/KOC (pH 5.5): 642.26; (8)ACD/KOC (pH 7.4): 642.26; (9)#H bond acceptors: 2; (10)#Freely Rotating Bonds: 2; (11)Index of Refraction: 1.642 ; (12)Molar Refractivity: 57.527 cm3; (13)Molar Volume: 159.218 cm3; (14)Polarizability: 22.805 10-24cm3; (15)Surface Tension: 45.2000007629395 dyne/cm; (16)Density: 1.17 g/cm3; (17)Flash Point: 162.74 °C; (18)Enthalpy of Vaporization: 58.375 kJ/mol; (19)Boiling Point: 340.216 °C at 760 mmHg

Preparation of 6-Methoxy-2-Naphthaldehyde: It can be obtained by methyl-(6-methyl-[2]naphthyl)-ether. This reaction needs reagent 2,3-dichloro-5,6-dicyano-1,4-benzoquinone and solvents acetic acid, H2O by heating. The reaction time is 4.0 hours. The yield is 90%.

Preparation of 6-Methoxy-2-Naphthaldehyde

Uses of 6-Methoxy-2-Naphthaldehyde: It is used as intermediate of Nabumetone. It is also used for fluorometric assays for isozymes of human alcohol dehydrogenase. What's more, it can react with malonic acid diethyl ester to get (6-methoxy-[2]naphthylmethylene)-malonic acid diethyl ester. This reaction needs reagent piperidine, benzoic acid and solvent benzene by heating. The reaction time is 16 hours. The yield is 81%.

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin, so people should avoid contact with skin and eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection.

People can use the following data to convert to the molecule structure.
1. SMILES:O=Cc1ccc2c(c1)ccc(OC)c2
2. InChI:InChI=1/C12H10O2/c1-14-12-5-4-10-6-9(8-13)2-3-11(10)7-12/h2-8H,1H3
3. InChIKey:VZBLASFLFFMMCM-UHFFFAOYAL

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