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5111-65-9

Basic Information
CAS No.: 5111-65-9
Name: Naphthalene,2-bromo-6-methoxy-
Article Data: 42
Cas Database
Molecular Structure:
Molecular Structure of 5111-65-9 (Naphthalene,2-bromo-6-methoxy-)
Formula: C11H9BrO
Molecular Weight: 237.096
Synonyms: 2-Bromo-6-methoxynaphthaline;2-Methoxy-6-bromonaphthalene;6-Bromo-2-methoxynaphthalene;6-Methoxy-2-bromonaphthalene;NSC 3236;
EINECS: 225-837-0
Density: 1.447 g/cm3
Melting Point: 106-109 °C(lit.)
Boiling Point: 324.7 °C at 760 mmHg
Flash Point: 134.7 °C
Solubility: Soluble in DMSO. Insoluble in water.
Appearance: white to light beige powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36-37/39
Transport Information: N/A
PSA: 9.23000
LogP: 3.61090
Synthetic route
15231-91-1

6-bromo-naphthalen-2-ol

74-83-9

methyl bromide

5111-65-9

2-Bromo-6-methoxynaphthalene

Conditions
ConditionsYield
With potassium carbonate In acetonitrile for 3h; Reflux;99%
With potassium tert-butylate In dimethyl sulfoxide for 0.25h;
93-04-9

2-Methoxynaphthalene

5111-65-9

2-Bromo-6-methoxynaphthalene

Conditions
ConditionsYield
With hydrogen bromide; sodium bromide In chloroform; water at 0℃; Electrochemical reaction;98%
With bromine; acetic acid at 55 - 85℃; under 760.051 Torr; for 0.275h; Temperature;90.2%
With tin; bromine; acetic acid 2.) reflux; Multistep reaction;
15231-91-1

6-bromo-naphthalen-2-ol

74-88-4

methyl iodide

5111-65-9

2-Bromo-6-methoxynaphthalene

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 100℃;97%
With caesium carbonate In acetone at 0 - 26℃;97%
With potassium carbonate In N,N-dimethyl-formamide96%
15231-91-1

6-bromo-naphthalen-2-ol

616-38-6

carbonic acid dimethyl ester

5111-65-9

2-Bromo-6-methoxynaphthalene

Conditions
ConditionsYield
Stage #1: 6-bromo-naphthalen-2-ol With tetrabutyl-ammonium chloride; potassium carbonate at 135℃; Neat (no solvent);
Stage #2: carbonic acid dimethyl ester at 130 - 135℃; for 6h; Neat (no solvent);
95%
15231-91-1

6-bromo-naphthalen-2-ol

77-78-1

dimethyl sulfate

5111-65-9

2-Bromo-6-methoxynaphthalene

Conditions
ConditionsYield
With potassium carbonate In acetone for 12h; Reflux;92%
With caesium carbonate In acetone at 20℃; for 0.5h;91%
With aluminum oxide; potassium hydroxide for 6h; microwave irradiation;88%
15231-91-1

6-bromo-naphthalen-2-ol

75-57-0

tetramethlyammonium chloride

5111-65-9

2-Bromo-6-methoxynaphthalene

Conditions
ConditionsYield
With caesium carbonate In 1,2-dimethoxyethane at 145℃; for 1h; Microwave irradiation; Inert atmosphere; Sealed vessel;92%
15231-91-1

6-bromo-naphthalen-2-ol

methyl halide

methyl halide

5111-65-9

2-Bromo-6-methoxynaphthalene

Conditions
ConditionsYield
With potassium carbonate In acetonitrile for 24h; Reflux;81%
With potassium carbonate In N,N-dimethyl-formamide at 80℃;
15231-91-1

6-bromo-naphthalen-2-ol

55476-88-5

4-benzyl-4-methylmorpholinium chloride

A

5111-65-9

2-Bromo-6-methoxynaphthalene

B

2234-45-9

6-benzyloxy-2-bromonaphthalene

Conditions
ConditionsYield
With potassium carbonate at 150 - 160℃; for 2h;A n/a
B 72%

6-bromonaphthalen-2-yl 4-methylbenzenesulfonate

865-33-8

potassium methanolate

5111-65-9

2-Bromo-6-methoxynaphthalene

Conditions
ConditionsYield
In acetonitrile at 45℃; Schlenk technique; Inert atmosphere;70%
In acetonitrile at 45℃; for 18.5h;70%
34352-92-6

2-methoxy-6-(prop-1-en-2-yl)-naphthalene

A

5111-65-9

2-Bromo-6-methoxynaphthalene

B

182816-10-0

2-(2-Bromo-1-fluoro-1-methyl-ethyl)-6-methoxy-naphthalene

C

1-Bromo-6-(2-bromo-1-fluoro-1-methyl-ethyl)-2-methoxy-naphthalene

Conditions
ConditionsYield
With N-Bromosuccinimide; triethylamine tris(hydrogen fluoride) In dichloromethane for 14h; Ambient temperature;A 4%
B 29%
C 67%
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  • 2-Bromo-6-methoxynaphthalene     CAS: 5111-65-9

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    Product name: 2-Bromo-6-Methoxynaphthalene CAS No.:5111-65-9 Molecule Formula:C11H9BrO Molecule Weight:237.09 Purity: 99.0% Package: 25kg/drum Description:Yellowish to off-white powder Manufacture Standards:Enterprise Standard

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Specification

The IUPAC name of 6-Methoxy-2-bromonaphthalene is 2-bromo-6-methoxynaphthalene. With the CAS registry number 5111-65-9 and EINECS 225-837-0, it is also named as Naphthalene, 2-bromo-6-methoxy-. The product's categories are Naphthalene Derivatives; Ethers; Organic Building Blocks; Oxygen Compounds. It is white to light beige 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.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 4.14; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 4.14; (4)ACD/LogD (pH 7.4): 4.14; (5)ACD/BCF (pH 5.5): 819.24; (6)ACD/BCF (pH 7.4): 819.24; (7)ACD/KOC (pH 5.5): 4236.62; (8)ACD/KOC (pH 7.4): 4236.62; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 9.23 Å2; (13)Index of Refraction: 1.632; (14)Molar Refractivity: 58.46 cm3; (15)Molar Volume: 163.7 cm3; (16)Surface Tension: 42.5 dyne/cm; (17)Enthalpy of Vaporization: 54.42 kJ/mol; (18)Vapour Pressure: 0.000459 mmHg at 25°C; (19)Rotatable Bond Count: 1; (20)Exact Mass: 235.983678; (21)MonoIsotopic Mass: 235.983678; (22)Topological Polar Surface Area: 9.2; (23)Heavy Atom Count: 13; (24)Complexity: 172.

Preparation of 6-Methoxy-2-bromonaphthalene: It can be obtained by sulfuric acid dimethyl ester and 6-bromo-naphthalen-2-ol. This reaction needs reagents KOH and basic alumina by microwave irradiation. The reaction time is 6hours. The yield is 88%.

Uses of 6-Methoxy-2-bromonaphthalene: It is used as intermediate of Nabumetone. It also can react with 4-bromo-benzonitrile to get 2-(4'-cyanophenyl)-6-methoxynaphthalene. This reaction needs reagents Mg, ZnCl2*2Et2O, Pd(PPh3)4 and solvent tetrahydrofuran. The yield is 63%.

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin. 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:Brc2ccc1c(ccc(OC)c1)c2
2. InChI:InChI=1/C11H9BrO/c1-13-11-5-3-8-6-10(12)4-2-9(8)7-11/h2-7H,1H3
3. InChIKey:AYFJBMBVXWNYLT-UHFFFAOYAGd.