70-11-1

Basic information

• Product Name: 2-Bromoacetophenone
• Synonyms: ω-Bromoacetophenone, Phenacyl bromide;1-(Bromoacetyl)benzene;Bromoacetylbenzene;roxylamine hydrochloride;w-Bromoacetophenone;2-Bromoacetophenone,ω-Bromoacetophenone, Phenacyl bromide;2-Bromoacetophenone ,99%;2-Bromoacetophenone, 2-Bromo-1-phenylethan-1-one
• CAS NO: 70-11-1
• Molecular Formula: C₈H₇BrO
• Molecular Weight: 199.04
• EINECS: 200-724-9
• Product Categories: HPLC Labeling Reagents;UV Detection (HPLC Labeling Reagents);Acetophenone series;ketone| alkyl bromide;Analytical Chemistry;Carboxyl Group Labeling Reagents for HPLC
• Mol File: 70-11-1.mol
• Article Data: 276

Chemical Properties

• Melting Point: 48-51 °C(lit.)
• Boiling Point: 135 °C18 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: White to dark green-brown/Crystals or Powder
• Density: 1.476
• Vapor Pressure: 0.0184mmHg at 25°C
• Refractive Index: 1.5700 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• Water Solubility: PRACTICALLY INSOLUBLE
• Stability: Stable. Incompatible with strong bases, strong oxidizing agents. Combustible.
• Merck: 14,1402
• BRN: 606474
• CAS DataBase Reference: 2-Bromoacetophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromoacetophenone(70-11-1)
• EPA Substance Registry System: 2-Bromoacetophenone(70-11-1)

Safety Data

• Hazard Codes: C
• Statements: 34-20/21/22
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 2645 6.1/PG 2
• WGK Germany: 3
• F: 8-19
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 70-11-1(Hazardous Substances Data)

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.]

InChI:InChI=1/C8H7BrO/c9-6-8(10)7-4-2-1-3-5-7/h1-5H,6H2

Upstream product

• 77-48-5 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione 
• 98-86-2 acetophenone 
• 98-81-7 1-bromovinylbenzene 
• 22118-09-8 2-bromoacetyl chloride 
• 71-43-2 benzene 
• 1145-25-1 methyl-phenacyl-phenyl sulfonium ; bromide 
• 40923-93-1 tetraethoxyethene 
• 136132-07-5 3-(bromomethyl)-3-phenyl-1,2-dioxetane 
• 2425-28-7 2-Bromo-1-phenylethanol 
• 108773-82-6 3-Bromomethyl-4,4-dimethyl-3-phenyl-[1,2]dioxetane 
• 66694-19-7 α-(4-methoxyphenoxy)styrene 
• 123577-99-1 3′,5′-difluoroacetophenone 
• 98-85-1 1-Phenylethanol 
• 100-41-4 ethylbenzene 

Downstream Products

• 779-53-3 4-morpholinylacetophenone 
• 110704-59-1 (4-phenylthiazol-2-yl)methyl benzoate 
• 16883-69-5 N-phenacylpyridinium bromide 
• 32896-98-3 2-methyl-1-(2-oxo-2-phenylethyl)pyridinium bromide 
• 7250-28-4 4-methyl-1-(2-oxo-2-phenylethyl)pyridinium bromide 
• 46721-77-1 1-phenyl-2-(pyridin-2-ylthio)ethan-1-one 
• 6273-90-1 N-phenacyl-2-chloropyridinium bromide 
• 7146-43-2 1-benzoylmethyl-2-bromopyridinium bromide 
• 107624-94-2 1-phenacyl-1H-pyridin-4-one 
• 6299-99-6 3-bromo-1-phenacylpyridinium bromide 
• 15764-47-3 2-phenylimidazo(1,2-a)pyrimidine 
• 100869-89-4 2-(4-methyl-pyridin-2-ylamino)-1-phenyl-ethanone 
• 33014-32-3 1-phenacylquinolinium bromide 
• 25131-60-6 2-phenacylisoquinolinium bromide 

Relevant articles and documents

Simultaneous multistep synthesis using polymeric reagents

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).

A General Method for the Dibromination of Vicinal sp3C-H Bonds Exploiting Weak Solvent-Substrate Noncovalent Interactions

A general procedure of 1,2-dibromination of vicinal sp3 C-H bonds of arylethanes using N-bromosuccinimide as the bromide reagent without an external initiator has been established. The modulation of the strength of the intermolecular noncovalent interactions between the solvent and arylethane ethanes, quantitatively evaluated via quantum chemical calculations, allows us to circumvent the fact that arylethane ethane cannot be dibrominated through traditional methods. The mechanism was explored by both experiments and quantum chemical calculations, revealing a radical chain with HAA process.

Solvent-free preparation of α,α-dichloroketones with sulfuryl chloride

An efficient and facile method is reported for the synthesis of a series of α,α-dichloroketones. The direct dichlorination of methyl ketones and 1,3-dicarbonyls using an excess amount of sulfuryl chloride affords the corresponding gem-dichloro compounds in moderate to excellent yields. Moreover, the protocol features high yields, broad substrate scope, and simple reaction conditions without using any catalysts and solvents.