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2-Bromo-4'-methoxyacetophenone

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2-Bromo-4'-methoxyacetophenone Basic information

Product Name:
2-Bromo-4'-methoxyacetophenone
Synonyms:
  • ALPHA-BROMO-4'-METHOXYACETOPHENONE
  • ALPHA-BROMO-4-METHOXYACETOPHENONE
  • AKOS BBS-00000817
  • Bromomethyl 4-methoxyphenyl ketone
  • 4-(BROMOACETYL)ANISOLE
  • 4-methoxy phenecyl bromide
  • 4-METHOXYPHENACYL BR
  • 4'-METHOXYPHENACYL BROMIDE
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
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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
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
SMILES
C(=O)(C1=CC=C(OC)C=C1)CBr
CAS DataBase Reference
2632-13-5(CAS DataBase Reference)
NIST Chemistry Reference
Ethanone, 2-bromo-1-(4-methoxyphenyl)-(2632-13-5)
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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

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2-Bromo-4'-methoxyacetophenone Usage And Synthesis

Chemical Properties

off-white to light brown crystals or

Uses

2-Bromo-4'-methoxyacetophenone, is used as a cell-permeable, covalent and potent protein tyrosine phosphatase inhibitor.

Uses

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

Preparation

Obtained 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 Activity

ki: 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 vitro

in 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).

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