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Name |
2-Bromoanisole |
EINECS | 209-425-8 |
CAS No. | 578-57-4 | Density | 1.443 g/cm3 |
PSA | 9.23000 | LogP | 2.45770 |
Solubility | soluble in ethanol and diethyl ether, insoluble in water | Melting Point |
2 °C(lit.) |
Formula | C7H7BrO | Boiling Point | 215.999 °C at 760 mmHg |
Molecular Weight | 187.036 | Flash Point | 96.667 °C |
Transport Information | UN 3082 9/PG 3 | Appearance | colourless liquid |
Safety | 61-24/25 | Risk Codes | 51/53 |
Molecular Structure | Hazard Symbols | N,Xi | |
Synonyms |
Anisole,o-bromo- (6CI,7CI,8CI);1-Bromo-2-methoxybenzene;2-Bromo-1-methoxybenzene;2-Bromomethoxybenzene;2-Methoxyphenylbromide;NSC 6977;o-Anisyl bromide;o-Bromoanisole;o-Bromomethoxybenzene;o-Bromophenyl methyl ether;o-Methoxyphenyl bromide;2-Bromoanisole; |
Article Data | 79 |
methoxybenzene
A
1-bromo-4-methoxy-benzene
B
2-bromoanisole
C
2,4-dibromoanisole
Conditions | Yield |
---|---|
With bromine; tetramethylammonium bromide In liquid sulphur dioxide at -23℃; Rate constant; Product distribution; Thermodynamic data; in H2O at 25 deg C, NaBr, HClO4; ΔH (excit), -ΔS (excit); | A 98.99% B 0.56% C 0.43% |
With (CH3)4Br In liquid sulphur dioxide at -23℃; Kinetics; Thermodynamic data; Product distribution; ΔH(excit.); ΔS(excit.); | A 98.99% B 0.56% C 0.43% |
With (CH3)4Br In liquid sulphur dioxide at -23℃; | A 98.99% B 0.56% C 0.43% |
Conditions | Yield |
---|---|
With tert.-butylnitrite; tetrabutylammomium bromide; copper(I) bromide; 10-camphorsulfonic acid In acetonitrile at 20℃; for 24h; Reagent/catalyst; Time; Solvent; | 98% |
Stage #1: 2-methoxy-phenylamine With tert.-butylnitrite In dichloromethane; water at 0℃; for 0.166667h; Stage #2: With carbon tetrabromide; dimethylglyoxal In dichloromethane; water at 15 - 35℃; for 16h; | 78% |
With tert.-butylnitrite; tetrabutylammomium bromide; toluene-4-sulfonic acid; copper(ll) bromide In acetonitrile at 20℃; for 23h; | 74% |
Conditions | Yield |
---|---|
With Oxone; potassium bromide In methanol at 20℃; for 1h; | A 97% B 2% |
With Oxone; potassium bromide In acetonitrile at 20℃; for 24h; | A 84% B 15% |
With PyHBrCl2 In methanol at 20℃; for 0.0833333h; | A 78% B 18% |
Conditions | Yield |
---|---|
With N-Bromosuccinimide In acetonitrile at 80℃; for 12h; | 97% |
With tetrabutylammomium bromide; copper(ll) bromide In water at 100℃; for 8h; Sealed tube; | 82% |
With 1,10-Phenanthroline; oxygen; potassium bromide; copper(ll) bromide In N,N-dimethyl-formamide at 130℃; for 20h; | 67% |
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; sodium methylate In methanol; water; acetonitrile at 23℃; | 94 % Chromat. |
Conditions | Yield |
---|---|
Stage #1: 2-hydroxybromobenzene With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 1.16667h; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran; mineral oil at 20℃; for 19h; Inert atmosphere; Reflux; | 97% |
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 2.5h; Inert atmosphere; | 96% |
With potassium hydroxide In CD2Cl2; hexane; acetonitrile | 89% |
Conditions | Yield |
---|---|
With potassium carbonate at 60℃; for 0.3h; Williamson synthesis; | 94% |
With sodium hydroxide | |
With potassium hydroxide | |
With sodium hydroxide for 3h; Heating; | |
With potassium carbonate In acetone Inert atmosphere; |
Conditions | Yield |
---|---|
With potassium phosphate; tetrabuthylammonium tribromide In acetonitrile at 100℃; for 16h; Reagent/catalyst; | 90% |
Conditions | Yield |
---|---|
With sodium carbonate In N,N-dimethyl-formamide at 120℃; for 4h; | 90% |
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide for 0.0583333h; microwave irradiation; | 84% |
With leucine intercalated Mg-Al layered double hydorxide at 180℃; for 6h; Autoclave; Green chemistry; chemoselective reaction; | 87 %Chromat. |
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 25℃; for 3h; Inert atmosphere; Schlenk technique; | 84% |
The 2-Bromoanisole, with the CAS registry number 578-57-4, is also known as 2-Bromo-1-methoxybenzene. It belongs to the product categories of Aromatic Halides(substituted); Anisole; Miscellaneous; Anisoles, Alkyloxy Compounds & Phenylacetates; Bromine Compounds. Its EINECS number is 209-425-8. This chemical's molecular formula is C7H7BrO and molecular weight is 187.03. What's more, its systematic name is 1-Bromo-2-methoxybenzene. It is used in organic synthesis. This chemical should be sealed and stored in a cool and dry place. Moreover, it should be protected from oxides, light and moisture.
Physical properties of 2-Bromoanisole are: (1)ACD/LogP: 2.705; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.71 ; (4)ACD/LogD (pH 7.4): 2.71; (5)ACD/BCF (pH 5.5): 67.00; (6)ACD/BCF (pH 7.4): 67.00; (7)ACD/KOC (pH 5.5): 705.86; (8)ACD/KOC (pH 7.4): 705.86; (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: 1.539; (14)Molar Refractivity: 40.622 cm3; (15)Molar Volume: 129.621 cm3; (16)Polarizability: 16.104×10-24cm3; (17)Surface Tension: 34.6 dyne/cm; (18)Density: 1.443 g/cm3; (19)Flash Point: 96.667 °C; (20)Enthalpy of Vaporization: 43.392 kJ/mol; (21)Boiling Point: 215.999 °C at 760 mmHg; (22)Vapour Pressure: 0.2 mmHg at 25°C.
Preparation of 2-Bromoanisole: this chemical can be prepared by methoxybenzene at the temperature of 20 °C. This reaction will need reagents Oxone, potassium bromide and solvent methanol with the reaction time of 1 hour. The yield is about 97%.
Uses of 2-Bromoanisole: it can be used to produce (2-methoxy-phenyl)-acetone at the temperature of 100 °C. It will need regent tributyltin methoxide and solvent toluene with the reaction time of 5 hours. This reaction will also need catalyst dichlorobis(tri-o-tolylphosphine)palladium. The yield is about 90%.
When you are using this chemical, please be cautious about it as the following:
This chemical is toxic to aquatic organisms as it may cause long-term adverse effects in the aquatic environment. You should avoid releasing it to the environment, and you need to refer to special instructions/safety data sheet. When using it, you must avoid contact with skin and eyes.
You can still convert the following datas into molecular structure:
(1)SMILES: COc1ccccc1Br
(2)Std. InChI: InChI=1S/C7H7BrO/c1-9-7-5-3-2-4-6(7)8/h2-5H,1H3
(3)Std. InChIKey: HTDQSWDEWGSAMN-UHFFFAOYSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 1544mg/kg (1544mg/kg) | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 44(12), Pg. 19, 1979. | |
mouse | LD50 | oral | 2466mg/kg (2466mg/kg) | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 44(12), Pg. 19, 1979. |