3'-METHOXYPHENACYL BROMIDE Chemical Properties

Melting point:

60-62 °C(lit.)

Boiling point:

215.8°C (rough estimate)

Density 

1.4921 (rough estimate)

refractive index 

1.5500 (estimate)

storage temp. 

2-8°C

solubility 

soluble in Methanol

form 

Crystalline Powder

color 

White to slightly yellow-green

BRN 

510128

InChI

InChI=1S/C9H9BrO2/c1-12-8-4-2-3-7(5-8)9(11)6-10/h2-5H,6H2,1H3

InChIKey

IOOHBIFQNQQUFI-UHFFFAOYSA-N

SMILES

C(=O)(C1=CC=CC(OC)=C1)CBr

CAS DataBase Reference

5000-65-7(CAS DataBase Reference)

NIST Chemistry Reference

2-Bromo-3'-methoxyacetophenone(5000-65-7)

Safety Information

Hazard Codes 

C

Risk Statements 

34-36/37-22

Safety Statements 

26-27-28-36/37/39-45-34

RIDADR 

UN 3261 8/PG 2

WGK Germany 

3

HazardClass 

8

PackingGroup 

III

HS Code 

29147000

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

3'-METHOXYPHENACYL BROMIDE Usage And Synthesis

Chemical Properties

WHITE TO SLIGHTLY YELLOW-GREEN CRYST. POWDER

Uses

Derivatizing reagent.

Uses

2-bromo-3′-methoxyacetophenone, an alkylating agent, has been used to stabilize clopidogrel active metabolite (AM) in human plasma. It has also been used in the derivatisation of active metabolites in blood to ensure its stability during sample processing and storage.

Preparation

Obtained by reaction of bromine with 3-methoxyacetophenone in chloroform at 0° for 3 h (88%).

Synthesis

General procedure for the synthesis of 2-bromo-3'-methoxyacetophenone from 3-methoxyacetophenone: To a stirred yellow solution of clarified 1-(3-methoxyphenyl)acetophenone (20 mL, 139 mmol) in tetrahydrofuran (250 mL) was added in batches of tribromobenzyltrimethylammonium (54.7 g, 145 mmol) and stirring was continued for 1 h at room temperature. After completion of the reaction, the ammonium salt was removed by filtration and the filter cake was washed with ether. Subsequently, the filtrate was concentrated under reduced pressure to give the oily product 2-bromo-1-(3-methoxyphenyl)ethanone (32.6 g, 142 mmol) which could be used without further purification in quantitative yield.

References

[1] Patent: WO2015/16729, 2015, A1. Location in patent: Page/Page column 30
[2] Journal of Medicinal Chemistry, 2017, vol. 60, # 22, p. 9239 - 9250
[3] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 15, p. 5715 - 5723
[4] Journal of the Chemical Society of Pakistan, 2016, vol. 38, # 5, p. 859 - 863
[5] Journal of the American Chemical Society, 1984, vol. 106, # 11, p. 3354 - 3356

3'-METHOXYPHENACYL BROMIDE(5000-65-7)Related Product Information

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