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HomeProduct name list2-Bromo-4'-hydroxyacetophenone

2-Bromo-4'-hydroxyacetophenone

Synonym(s):p-Hydroxyphenacyl bromide;2-Bromo-1-(4-hydroxyphenyl)ethanone;Protein Tyrosine Phosphatase Inhibitor I, α-Bromo-4-hydroxyacetophenone, 4-Hydroxyphenacyl Br, SHP1 Inhibitor II;PTP Inhibitor I - CAS 2491-38-5 - Calbiochem

  • CAS NO.:2491-38-5
  • Empirical Formula: C8H7BrO2
  • Molecular Weight: 215.04
  • MDL number: MFCD00072424
  • EINECS: 219-655-0
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-20 11:41:24
2-Bromo-4'-hydroxyacetophenone Structural

What is 2-Bromo-4'-hydroxyacetophenone?

Description

PTP Inhibitor I is a cell-permeable, protein tyrosine phosphatase (PTP) inhibitor that covalently blocks the catalytic domain of the Src homology region 2 domain-containing phosphatase (SHP-1(ΔSH2)) with a Ki value of 43 μM and PTP1B with a Ki value of 42 μM. SHP-1 and PTP1B both have known roles in regulating insulin signaling as well as myeloid and lymphoid cell differentiation, making inhibitors of these phosphatases of interest in diabetes, cancer, allergy, and inflammation research.

Chemical properties

Pale Beige Solid

The Uses of 2-Bromo-4'-hydroxyacetophenone

A covalent inhibitor of protein tyrosine phosphatases (PTPs)

What are the applications of Application

PTP Inhibitor I is a potent covalent inhibitor of protein tyrosine phosphatases SHP-1 and PTPIB

Preparation

Also obtained by reaction of pyridinium hydrobromide perbromide with 4-hydroxyacetophenone in THF at r.t. for 3 h.

in vitro

in previous study, the corresponding values of ptp inhibitor i against ptp1b were determined to be ki of 42 μm, kinact of 0.57 min-1, and kinact/ki of 1.4*104 m-1 min-1, respectively. this study also showed that α-bromoacetophenone such as ptp inhibitor i could provide an effective, neutral py mimetic inhibitor of ptps. while perturbation of the electronic properties of the phenyl ring did not significantly improve its potency against ptps, attachment of a proper peptidyl moiety to the para position could improve both the potency and the selectivity substantially. in addition, since the covalent ptp inhibitor complex could be cleaved to regenerate the ptp activity photolytically, ptp inhibitor i might provide a novel class of photolytic switch for controlling cellular signaling processes [1].

References

[1] arabaci g, yi t, fu h, porter me, beebe kd, pei d. alpha-bromoacetophenone derivatives as neutral protein tyrosine phosphatase inhibitors: structure-activity relationship. bioorg med chem lett. 2002 nov 4;12(21):3047-50.

Properties of 2-Bromo-4'-hydroxyacetophenone

Melting point: 123-126°C
Boiling point: 338.7±17.0 °C(Predicted)
Density  1.622±0.06 g/cm3(Predicted)
storage temp.  Inert atmosphere,2-8°C
solubility  Chloroform (Slightly), Methanol (Slightly)
form  White powder
pka 7.69±0.15(Predicted)
color  White to Light Beige
Sensitive  Lachrymatory
BRN  1865388
Stability: Hygroscopic
CAS DataBase Reference 2491-38-5(CAS DataBase Reference)
EPA Substance Registry System 2-Bromo-4-hydroxyacetophenone (2491-38-5)

Safety information for 2-Bromo-4'-hydroxyacetophenone

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H302:Acute toxicity,oral
H319:Serious eye damage/eye irritation
Precautionary Statement Codes P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P270:Do not eat, drink or smoke when using this product.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P337+P313:IF eye irritation persists: Get medical advice/attention.

Computed Descriptors for 2-Bromo-4'-hydroxyacetophenone

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