ChemicalBook Product Catalog Chemical Reagents Organic reagents Aromatic ketones 3'-Methoxyphenacyl bromide

3'-Methoxyphenacyl bromide

Product Name3'-Methoxyphenacyl bromide
CAS5000-65-7
MFC9H9BrO2
MW229.07
EINECS225-666-1
MOL File5000-65-7.mol

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
Storage Class	8A - Combustible corrosive hazardous materials
Hazard Classifications	Eye Dam. 1 Skin Corr. 1B STOT SE 3

MSDS

Provider	Language
ACROS	English
SigmaAldrich	English
ALFA	English

Usage And Synthesis

Chemical Properties

WHITE TO SLIGHTLY YELLOW-GREEN CRYST. POWDER

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.

Uses

Derivatizing reagent.

Preparation

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

Synthesis

586-37-8

5000-65-7

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

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

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