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

Chemical Properties

Off white-grey green crystaline powder

Uses

Different sources of media describe the Uses of 70-11-1 differently. You can refer to the following data:
1. 2-Bromoacetophenone is a brominated acteophenone derivative. 2-Bromoacetophenone has been shown to completely and irreversibly inactivate human liver aldehyde dehydrogenase (EC 1.2.1.3) isoenzymes E1 and E2. 2-Bromoacetophenone and its derivatives display some inhibitory activity on neutral protein tyrosine.inhibitors
2. Preparation of crystalline esters from acids
3. It is used in preparation of crystalline esters from acids. 2-Bromoacetophenone is a complete and irreversible inactivator of human liver aldehyde dehydrogenase isoenzymes E1 and E2.

Definition

ChEBI: An alpha-bromoketone that is acetophenone substituted by a bromo group at position 2.

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

General Description

A crystalline solid or a liquid with a sharp odor. Toxic by inhalation, ingestion and skin absorption. A severe eye irritant (a lachrymator). Used to make other chemicals.

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

• 7402-45-1 α,α,α-tribromoacetophenone 
• 78-92-2 iso-butanol 
• 71-36-3 butan-1-ol 
• 1509-37-1 1,4-dibromo-3-hydroxy-3-phenyl-butan-2-one 
• 64-19-7 acetic acid 
• 67-56-1 methanol 
• 7553-56-2 iodine 
• 3360-54-1 3-bromo-2-phenylprop-1-ene 
• 100-41-4 ethylbenzene 
• 536-74-3 phenylacetylene 
• 98-81-7 1-bromovinylbenzene 
• 618-34-8 1-chlorostyrene 
• 876-27-7 4-chlorophenyl acetate 
• 2425-28-7 2-Bromo-1-phenylethanol 

Downstream Products

• 779-53-3 4-morpholinylacetophenone 
• 5653-11-2 α-(1,2,3,4-Tetrahydro-2-isochinolyl)-acetophenon 
• 5304-34-7 2-(3-thiazolium)-1-phenylethanone bromide 
• 24155-34-8 2-(1H-imidazol-1-yl)-1-phenylethanone 
• 109407-55-8 1-phenacyl-pyrimidinium; bromide 
• 6277-94-7 4-phenacyl-4-phenethyl-morpholinium; bromide 
• 855292-13-6 4-phenacylamino-benzoic acid 
• 19514-01-3 1-phenyl-2-(o-tolyloxy)ethanone 
• 101444-72-8 8-methyl-2-phenacylmercapto-3H-quinazolin-4-one 
• 108487-89-4 5-methyl-thiazole-2-carbaldehyde-(4-phenyl-thiazol-2-ylhydrazone) 
• 102468-20-2 pyrazine-2,3-dicarboxylic acid diphenacyl ester 
• 102028-42-2 2-methyl-4-(2-oxo-2-phenylethyl)isoquinoline-1,3(2H,4H)-dione 
• 102949-32-6 2-methyl-4,4-diphenacyl-4H-isoquinoline-1,3-dione 

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).

Flexible on-site halogenation paired with hydrogenation using halide electrolysis

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.

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.