70-11-1 Usage
Description
2-Bromoacetophenone is a brominated acetophenone derivative, characterized by the presence of a bromine atom attached to a benzene ring with an acetone functional group. It is known for its ability to completely and irreversibly inactivate human liver aldehyde dehydrogenase (EC 1.2.1.3) isoenzymes E1 and E2. Additionally, 2-Bromoacetophenone and its derivatives exhibit inhibitory activity against neutral protein tyrosine phosphatases.
Uses
Used in Pharmaceutical Industry:
2-Bromoacetophenone is used as a research chemical and pharmaceutical intermediate for the development of drugs targeting human liver aldehyde dehydrogenase isoenzymes E1 and E2. Its irreversible inactivation property makes it a valuable tool in studying enzyme function and potential therapeutic applications.
Used in Chemical Synthesis:
2-Bromoacetophenone is used in the preparation of crystalline esters from acids. Its reactivity and functional group make it a versatile building block for the synthesis of various organic compounds, particularly in the field of organic chemistry.
Used in Enzyme Inhibition Studies:
2-Bromoacetophenone is employed as an inhibitor of neutral protein tyrosine phosphatases, which are important enzymes involved in cellular signaling pathways. Its inhibitory activity is useful in understanding the role of these enzymes in various biological processes and may lead to the development of targeted therapies for related diseases.
Synthesis Reference(s)
Journal of the American Chemical Society, 76, p. 5796, 1954 DOI: 10.1021/ja01651a061Organic Syntheses, Coll. Vol. 2, p. 480, 1943Synthetic Communications, 22, p. 1923, 1992 DOI: 10.1080/00397919208021322
Air & Water Reactions
Reacts slowly with moisture in air to form hydrogen bromide.
Reactivity Profile
2-Bromoacetophenone reacts slowly with metals causing mild corrosion.
Health Hazard
TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.
Fire Hazard
Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.
Purification Methods
Crystallise the bromide from EtOH, MeOH or pet ether (b 80-100o). [Tanner J Org Chem 52 2142 1987, Beilstein 7 IV 649.]
Check Digit Verification of cas no
The CAS Registry Mumber 70-11-1 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 7 and 0 respectively; the second part has 2 digits, 1 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 70-11:
(4*7)+(3*0)+(2*1)+(1*1)=31
31 % 10 = 1
So 70-11-1 is a valid CAS Registry Number.
InChI:InChI=1/C8H7BrO/c9-6-8(10)7-4-2-1-3-5-7/h1-5H,6H2
70-11-1Relevant articles and documents
Simultaneous multistep synthesis using polymeric reagents
Parlow, John J.
, p. 1395 - 1396 (1995)
A synthesis was accomplished involving three transformations using three different polymeric reagents simultaneously in one reaction vessel to afford 2-[[4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl]oxy]-1-pheny lethanone (4).
Flexible on-site halogenation paired with hydrogenation using halide electrolysis
Shang, Xiao,Liu, Xuan,Sun, Yujie
supporting information, p. 2037 - 2043 (2021/03/26)
Direct electrochemical halogenation has appeared as an appealing approach in synthesizing organic halides in which inexpensive inorganic halide sources are employed and electrical power is the sole driving force. However, the intrinsic characteristics of direct electrochemical halogenation limit its reaction scope. Herein, we report an on-site halogenation strategy utilizing halogen gas produced from halide electrolysis while the halogenation reaction takes place in a reactor spatially isolated from the electrochemical cell. Such a flexible approach is able to successfully halogenate substrates bearing oxidatively labile functionalities, which are challenging for direct electrochemical halogenation. In addition, low-polar organic solvents, redox-active metal catalysts, and variable temperature conditions, inconvenient for direct electrochemical reactions, could be readily employed for our on-site halogenation. Hence, a wide range of substrates including arenes, heteroarenes, alkenes, alkynes, and ketones all exhibit excellent halogenation yields. Moreover, the simultaneously generated H2at the cathode during halide electrolysis can also be utilized for on-site hydrogenation. Such a strategy of paired halogenation/hydrogenation maximizes the atom economy and energy efficiency of halide electrolysis. Taking advantage of the on-site production of halogen and H2gases using portable halide electrolysis but not being suffered from electrolyte separation and restricted reaction conditions, our approach of flexible halogenation coupled with hydrogenation enables green and scalable synthesis of organic halides and value-added products.
METHOD FOR OXIDATIVE CLEAVAGE OF COMPOUNDS WITH UNSATURATED DOUBLE BOND
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Paragraph 0053-0059, (2021/03/19)
A method for oxidative cleavage of a compound with an unsaturated double bond is provided. The method comprises the following step: (A) providing a compound (I) with an unsaturated double bond, a reagent with trifluoromethyl, and a catalyst; wherein the catalyst is represented by the following formula (II): M(O)mL1yL2z (II); wherein, M, L1, L2, m, y, z, R1, R2 and R3 are defined in the specification; and (B) mixing the compound with an unsaturated double bond and the reagent with a trifluoromethyl to perform an oxidation of the compound with the unsaturated double bond by using the catalyst at air or an oxygen condition to get a compound presented as formula (III):
