2-bromo-1-(4-methoxyphenyl)ethan-1-one

• ChemBase ID: 80781
• Molecular Formular: C9H9BrO2
• Molecular Mass: 229.07056
• Monoisotopic Mass: 227.97859153
• SMILES: O=C(c1ccc(cc1)OC)CBr
• Canonical SMILES: BrCC(=O)c1ccc(cc1)OC
• InChI: InChI=1S/C9H9BrO2/c1-12-8-4-2-7(3-5-8)9(11)6-10/h2-5H,6H2,1H3
• InChIKey: XQJAHBHCLXUGEP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-bromo-1-(4-methoxyphenyl)ethan-1-one
• IUPAC Traditional name: 2-bromo-1-(4-methoxyphenyl)ethanone
• Synonyms: ω-Bromo-4-methoxyacetophenone; 4-Methoxyphenacyl bromide; 2-Bromo-4′-methoxyacetophenone; 2-bromo-1-(4-methoxyphenyl)ethan-1-one; 2-Bromo-1-(4-methoxyphenyl)ethanone; 2-(4-Methoxyphenyl)-2-oxoethyl bromide; 2-Bromo-1-(4-methoxyphenyl)-1-ethanone; 2-Bromo-1-[4-(methyloxy)phenyl]ethanone; 2-Bromo-p-methoxyacetophenone; 4-Methoxy-2'-bromoacetophenone; 4'-Methoxyphenacyl Bromide; Bromomethyl 4-Methoxyphenyl Ketone; Bromomethyl p-Anisyl Ketone; Bromomethyl p-Methoxyphenyl Ketone; NSC 129010; p-Methoxyphenacyl Bromide; α-Bromo-4'-methoxyacetophenone; α-Bromo-p-methoxyacetophenone; ω-Bromo-4'-methoxyacetophenone; ω-Bromo-p-methoxyacetophenone; 2-Bromo-4'-methoxyacetophenone; 2-Bromo-4'-methoxyacetophenone; 2-Bromo-1-(4-methoxyphenyl)ethan-1-one; 4-(Bromoacetyl)anisole; 4-Methoxyphenacyl bromide; 2-bromo-1-(4-methoxyphenyl)ethanone; alpha-Bromo-4-methoxyacetophenone; 2-Bromo-4'-methoxyacetophenone; ω-溴-4-甲氧基苯乙酮; 4-甲氧基苯甲酰基甲基溴; 2-溴-4′-甲氧基苯乙酮; 2-溴-4'-甲氧基苯乙酮

Database IDs

• CAS Number: 2632-13-5
• EC Number: 220-118-8
• MDL Number: MFCD00000201
• Beilstein Number: 743112
• PubChem SID: 24847233; 162067901
• PubChem CID: 4965

CALCULATED PROPERTIES

• Log P: 2.0960612
• Molar Refractivity: 50.6607 cm^3
• Polarizability: 19.334612 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true
• Acid pKa: 15.682729
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 2.0960612
• LogD (pH = 7.4): 2.0960612

PROPERTIES

Physical Property

• Melting Point: 68-72°C; 69-71 °C(lit.); 69-71°C; 69-72 °C

Safety Information

• Storage Warning: Corrosive/Harmful/Lachrymatory/Light Sensitive/Keep Cold/ Store under Argon
• European Hazard Symbols: Corrosive (C)
• UN Number: 3261; UN3261
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2; II
• Risk Statements: 34; 34-36/37
• Safety Statements: 26-27-28-36/37/39-45; 26-36/37/39-45
• TSCA Listed: 否
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H314-H318; H314-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338-P310; P280-P305+P351+P338-P309-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3261 8/PG 2
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... PTPN6(5777)

Product Information

• Purity: ≥97.0% (GC); 95+%; 97%; 98%
• Grade: purum
• Linear Formula: CH3OC6H4COCH2Br

DETAILS

Sigma Aldrich - 115665

Packaging
5, 25, 100 g in glass bottle

Toronto Research Chemicals - B684720

2-Bromo-4'-methoxyacetophenone is a α-haloacetophenone derivatives tested for inhibition of protein tyrosine phosphatases SHP-1 and PTP1B.

REFERENCES

• Taylor, W., et al.: Bioorg. Med. Chem., 4, 1515 (1996)
• Elchelby, M., et al.: Science, 283, 1544 (1996)
• Shen, K., et al.: J. Biol. Chem., 276, 47311 (1996)
• Wang, P., et al.: Biochemistry, 41, 6202 (1996)
• Reagent for protection of carboxylic acids as 4-methoxyphenacyl esters, which may be prepared in the presence of KF as base: Synthesis, 897 (1981) andcan be cleaved photolytically: J. Org. Chem., 38, 3771 (1973). Peptide bonds are generally unaffected by irradiation but some cleavage of trityl protecting groups may occur. See also Appendix 6. For further discussion of this and other photo-removable protecting groups, see: Synthesis, 1 (1980); Org. Photochem., 9, 225 (1987).