ChemicalBook > CAS DataBase List > Methyl2-bromo-4-methoxybenzoate

Methyl2-bromo-4-methoxybenzoate

Product Name: Methyl2-bromo-4-methoxybenzoate
CAS No.: 17100-65-1
Chemical Name: Methyl2-bromo-4-methoxybenzoate
Synonyms: Methyl2-bromo-4-methoxybenzoate;2-Bromo-4-methoxy-benzoic acid methyl ester;Benzoic acid, 2-bromo-4-methoxy-, methyl ester
CBNumber: CB82490731
Molecular Formula: C9H9BrO3
Formula Weight: 245.07
MOL File: 17100-65-1.mol

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Methyl2-bromo-4-methoxybenzoate Property

Melting point:: 29 °C
Boiling point:: 292.9±20.0 °C(Predicted)
Density: 1.462±0.06 g/cm3(Predicted)
storage temp.: Sealed in dry,Room Temperature
form: solid
color: Colourless
InChI: InChI=1S/C9H9BrO3/c1-12-6-3-4-7(8(10)5-6)9(11)13-2/h3-5H,1-2H3
InChIKey: MGIYCRUAYQQSNL-UHFFFAOYSA-N
SMILES: C(OC)(=O)C1=CC=C(OC)C=C1Br

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Safety

HS Code: 2918999090

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H301Toxic if swalloed

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Apolloscientific

Product number: OR55591
Product name: Methyl2-bromo-4-methoxybenzoate
Packaging: 1g
Price: $41
Updated: 2021/12/16

Matrix Scientific

Product number: 101221
Product name: Methyl 2-bromo-4-methoxybenzoate
Packaging: 1g
Price: $79
Updated: 2021/12/16

Apolloscientific

Product number: OR55591
Product name: Methyl2-bromo-4-methoxybenzoate
Packaging: 5g
Price: $148
Updated: 2021/12/16

Matrix Scientific

Product number: 101221
Product name: Methyl 2-bromo-4-methoxybenzoate
Packaging: 5g
Price: $318
Updated: 2021/12/16

American Custom Chemicals Corporation

Product number: HCH0369154
Product name: METHYL-2-BROMO-4-METHOXYBENZOATE
Purity: 95.00%
Packaging: 5MG
Price: $495.97
Updated: 2021/12/16

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Methyl2-bromo-4-methoxybenzoate Chemical Properties,Usage,Production

Uses

Methyl 2-bromo-4-methoxybenzoate is an organic compound that can be used as a ligand in asymmetric hydrogenation.

Synthesis

101085-03-4

74-88-4

17100-65-1

Example 7 Synthesis of methyl 2-bromo-4-methoxybenzoate (Compound 11): methyl 2-bromo-4-hydroxybenzoate (Compound 10, 815 mg, 3.54 mmol) was dissolved in N,N-dimethylformamide (DMF, 20 mL). Potassium carbonate (K2CO3, 1.17 g, 8.50 mmol) was added to the solution and the reaction mixture was stirred at room temperature for 20 minutes. Subsequently, the reaction mixture was cooled to 0 °C and a solution of iodomethane (265 μL, 4.25 mmol) in DMF (1 mL) was slowly added dropwise. After the dropwise addition, the reaction mixture was returned to room temperature and stirring was continued for 2 hours. Upon completion of the reaction, the reaction was quenched by the addition of water (50 mL) and then extracted with ether (Et2O, 200 mL). The organic phase was washed sequentially with water (3 x 40 mL) and saturated saline (40 mL). The organic layer was collected, dried with anhydrous sodium sulfate (Na2SO4), filtered and concentrated. Finally, the target product methyl 2-bromo-4-methoxybenzoate (Compound 11, 849 mg, 95.9% yield) was purified by silica gel column chromatography (eluent: hexane solution of 15% ethyl acetate) as a brown liquid. The structure of the product was confirmed by 1H-NMR, 13C-NMR and mass spectrometry (ESI): 1H-NMR (CDCl3, 400 MHz) δ 7.87 (1H, d, J = 8.4 Hz, ArH), 7.19 (1H, s, ArH), 6.88 (1H, d, J = 8.4 Hz, ArH), 3.90 (3H, s, OCH3). 3.84 (3H, s, OCH3); 13C-NMR (CDCl3, 100 MHz) δ 165.8, 162.2, 133.1, 123.5, 123.3, 119.7, 113.0, 55.6, 52.1; MS (ESI) m/z Calculated value C9H9BrO3 (M+): 244.0, Measured value: 244.1 (M+).

References

[1] Organic Letters, 2013, vol. 15, # 13, p. 3234 - 3237
[2] Patent: US2014/256817, 2014, A1. Location in patent: Page/Page column

Methyl2-bromo-4-methoxybenzoate Preparation Products And Raw materials

Raw materials

Preparation Products

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