2-Bromo-4'-methoxyacetophenone

2-Bromo-4'-methoxyacetophenone Basic information
Product Name:2-Bromo-4'-methoxyacetophenone
Synonyms:1-(2-bromo-4-methoxyphenyl)ethanone;P-Methoxy-α-bromoacetophenone;ω-Bromo-4-methoxyacetophenone, 4-Methoxyphenacyl bromide;2-(4-Methoxyphenyl)-2-oxoethyl bromid;1-(4-Mehtoxyphenyl)-2-bromoethanone;1-(Bromoacetyl)-4-methoxybenzene;4'-Methoxy-α-bromoacetophenone;2-Bromo-4'-methoxyacetophenone,98%
CAS:2632-13-5
MF:C9H9BrO2
MW:229.07
EINECS:220-118-8
Product Categories:Protection & Derivatization Reagents (for Synthesis);Synthetic Organic Chemistry
Mol File:2632-13-5.mol
2-Bromo-4'-methoxyacetophenone Structure
2-Bromo-4'-methoxyacetophenone Chemical Properties
Melting point 69-71 °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 Chloroform (Slightly), Methanol (Slightly)
form Crystals or Crystalline Powder
color Off-white to light brown
Water Solubility It is soluble in DMSO, water (partly miscible), most organic solvents, and methanol.
BRN 743112
InChIInChI=1S/C9H9BrO2/c1-12-8-4-2-7(3-5-8)9(11)6-10/h2-5H,6H2,1H3
InChIKeyXQJAHBHCLXUGEP-UHFFFAOYSA-N
SMILESC(=O)(C1=CC=C(OC)C=C1)CBr
CAS DataBase Reference2632-13-5(CAS DataBase Reference)
NIST Chemistry ReferenceEthanone, 2-bromo-1-(4-methoxyphenyl)-(2632-13-5)
Safety Information
Hazard Codes C,Xi
Risk Statements 34-36/37-36/37/38
Safety Statements 26-27-28-36/37/39-45-37/39
RIDADR UN 3261 8/PG 2
WGK Germany 3
8-9-19-21
Hazard Note Corrosive
HazardClass 8
PackingGroup III
HS Code 29147090
MSDS Information
ProviderLanguage
2-Bromo-1-(4-methoxyphenyl)ethanone English
SigmaAldrich English
ACROS English
ALFA English
2-Bromo-4'-methoxyacetophenone Usage And Synthesis
Chemical Propertiesoff-white to light brown crystals or
Uses2-Bromo-4'-methoxyacetophenone, is used as a cell-permeable, covalent and potent protein tyrosine phosphatase inhibitor.
Uses2-Bromo-4'-methoxyacetophenone is a α-haloacetophenone derivatives tested for inhibition of protein tyrosine phosphatases SHP-1 and PTP1B.
PreparationObtained by reaction of N-bromosuccinimide (NBS) with 4-methoxyacetophenone in the presence of trimethylsilyl trifluoromethanesulfonate (TMS-OTf) in acetonitrile at r.t. for 24 h (87%).
Biological Activityki: 128 μmptp inhibitor ii is a protein tyrosine phosphatase (ptp) inhibitor.protein tyrosine phosphatases (ptps) are reported to be involved in the etiology of diabetes mellitus, neural diseases such as alzheimer and parkinson diseases, regulation of allergy and inflammation, or ptps are even regarded to be responsible for the pathogens.
in vitroin a previous study, it was found that all of the previously reported ptp inhibitors contained a negatively charged, nonhydrolyzable py mimetic as the core structure, such as malonates, aryl carboxylates, phosphonates, or cinnamates. the poor membrane permeability of these inhibitors might compromise their potential development. it was reported that several α-bromoacetophenone derivatives, such as ptp inhibitor ii, could act as fairly potent ptp inhibitors, by covalently alkylating the conserved catalytic cysteine in the ptp active site. since ptp inhibitor ii is neutral, it could readily diffuse into human b cells and inhibit the intracellular ptps. the sar study was performed with the catalytic domain of phosphatase shp-1, and ti was found that ptp inhibitor ii showed time-dependent inactivation of shp-1, consistent with the mechanism. furthermore, the potency of ptp inhibitor ii was described by an equilibrium constant ki, representing the dissociation constant of the noncovalent enzyme–inhibitor complex. ptp inhibitor ii bound with lower affinity than ptp inhibitor i with ki values of 128 μm [1].
references[1] p. heneberg. use of protein tyrosine phosphatase inhibitors as promising targeted therapeutic drugs. current medicinal chemistry 16(6), 706-733 (2009).
2-Bromo-4'-chloroacetophenone 4-BROMO-2-METHOXYACETOPHENONE Chalcone 4'-Methoxyacetophenone 2'-BROMO-5'-METHOXYACETOPHENONE 4-(TRIFLUOROMETHOXY)PHENACYL BROMIDE 3'-METHOXYPHENACYL BROMIDE Methoxy 4-(9-ANTHROYLOXY)PHENACYL BROMIDE Clidinium bromide 4-BROMO-3-METHOXYACETOPHENONE L-PICEIN 2-Bromoacetophenone 5-BROMO-2-METHOXYACETOPHENONE 3'-Bromo-4'-methoxyacetophenone 4-(DIFLUOROMETHOXY)PHENACYL BROMIDE 4'-Benzyloxy-2-bromopropiophenone 3',5'-Dimethoxyacetophenone

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