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)

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

F 

8-9-19-21

Hazard Note 

Corrosive

HazardClass 

8

PackingGroup 

III

HS Code 

29147090

MSDS

• Language:English Provider:2-Bromo-1-(4-methoxyphenyl)ethanone
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

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).

2-Bromo-4'-methoxyacetophenone(2632-13-5)Related Product Information

• 3,4-Dimethoxyacetophenone
• Acetophenone
• Ethidium bromide
• 4'-Bromoacetophenone
• 3-Nitroacetophenone
• Chalcone
• Sodium bromate
• 3'-Bromoacetophenone
• Clidinium bromide
• L-PICEIN
• 4'-Methylacetophenone
• 3',5'-Dimethoxyacetophenone
• 2-Methoxyethanol
• 3-Bromoanisole
• 4'-Methoxyacetophenone
• 2'-Methoxyacetophenone
• 4-Nitroacetophenone
• 4'-Hydroxyacetophenone