79-15-2

Usage

Uses

Used in Pharmaceutical Industry:
N-BROMOACETAMIDE is used as a chemical agent for abolishing the rapid inactivation of membrane sodiumand potassium-ion channels. This property makes it useful in the development of drugs targeting ion channels, which are involved in various physiological processes and diseases.
Used in Cardiology:
In the field of cardiology, N-BROMOACETAMIDE is used to study and modulate the kinetics of cardiac sodium ion channels. This can help in understanding the mechanisms of cardiac arrhythmias and developing potential therapeutic agents for their treatment.

Air & Water Reactions

Soluble in water.

Reactivity Profile

N-BROMOACETAMIDE is sensitive to light, moisture, and heat. . N-BROMOACETAMIDE decomposes rapidly at elevated temperatures, in the presence of moisture and light.

Fire Hazard

Flash point data are not available for N-BROMOACETAMIDE, but N-BROMOACETAMIDE is probably combustible.

Purification Methods

A possible contaminant is CH3CONBr2. Recrystallise it from CHCl3/hexane (1:1, seed if necessary) or water and dry over CaCl2. It is a brominating agent. [Oliveto & Gerold Org Synth Coll Vol IV 104 1963.] Alternatively, dissolve it in the minimum volume of warm H2O (60o), then cool in an ice bath, collect the crystals and dry them in an anhydrous atmosphere, dissolve in Et2O, chill and evaporate till crystallisation. Dry the crystals in vacuo at 25o, then at 45o (m 108o). Crystallise from CHCl3 (m 103o). Estimate the available Br iodometrically [Buckles et al. J Org Chem 23 483 1958]. [Beilstein 2 H 181, 2 I 82, 2 II 180, 2 III 406, 2 IV 417.]

InChI:InChI=1/C2H4BrNO/c1-2(5)4-3/h1H3,(H,4,5)

Upstream product

• 60-35-5 acetamide 
• 598-93-6 N,N-dibromoacetamide 
• 2620-30-6 sodium acetylamide 
• 7726-95-6 bromine 
• 7732-18-5 water 
• 188434-13-1 ent-13-Acetoxy-3-oxo-20-norgibberella-1⁽¹⁰⁾,16-diene-7,19-dioic acid 7,19-dimethyl ester 

Downstream Products

• 1003-09-4 2-bromothiophene 
• 3141-27-3 2,5-dibromothiophen 
• 93-55-0 1-phenyl-propan-1-one 
• 128-08-5 N-Bromosuccinimide 
• 21770-48-9 rac-(R,S)-methyl 2,3-dibromo-3-phenylpropanoate 
• 911-40-0 7-ketodeoxycholic acid 
• 145631-86-3 2-bromocyclohexyl acetate 
• 51-79-6 urethane 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 103128-71-8 20-bromo-3-oxo-23,24-dinor-20ξH-chol-4-en-21-al 
• 64341-49-7 1-bromo-3-buten-2-ol 
• 6607-46-1 (1,2-dibromovinyl)benzene 
• 60-35-5 acetamide 
• 147-82-0 2,4,6-tribromoaniline 

Relevant academic research and scientific papers

One-pot synthesis of 2-oxazolines from ethyl α-cyanocinnamate derivatives with n-bromoacetamide

An efficient method for the one-pot synthesis of 2-oxazolines from ethyl α-cyanocinnamate derivatives with N-bromoacetamide in the presence of K3PO4 has been developed. The reaction performed smoothly and cleanly to give 2-oxazolines in good to excellent yields (up to 98%) within 4.5 h in acetone at room temperature without protection of inert gases. A total of 13 examples have been investigated. A possible nucleophilic addition reaction mechanism is proposed.

A peptide bromoiodinane approach for asymmetric bromolactonization

A series of 37 peptides containing an iodo-aryl amide active site were generated by means of both solid phase and conventional synthesis. These peptides were screened for asymmetric induction in the bromolactonization of 4-phenyl-4-pentenoic acid based on the generation of chiral bromoiodinane bromenium sources. The study culminated in the discovery of a tri-peptide iodo-aryl amide that effected the desired bromolactonization in quantitative conversion with 24% ee. The experiments disclosed herein provided valuable insight that ultimately facilitated the development of more synthetically useful enantioselective halocyclization methodology.

K3PO4-catalyzed regiospecific aminobromination of βnitrostyrene derivatives with N-Bromoacetamide as aminobtominating agent

"Chemical Equation Presented" A very simple, efficient, and regiospecific protocol for aminobromination of a wide scope of β-nitrostyrene derivatives with N-bromoacetamide (NBA) as nitrogen/ bromine sources has been developed by using K3PO4 as catalyst. The reaction proceeded smoothly and cleanly to give the bromoamines in good to excellent yields (78-99%) within 24 h in CH2Cl2 at room temperature without protection of inert gases. A possible mechanism involving a nucleophilic conjugate addition was proposed.

Unusual reactions of methylsulfonyl esters: Syntheses of 3α-methyl and 3β-methyl gibberellin A20

Gibberellin A3 has been converted to 3α-methylGA20 8 in 33% yield via catalytic hydrogenation of the 3-exo-methylene derivative 14. In an attempt to prepare 3β-methylGA20 9, the 3α-methanesulfonate 25 has been treated with lithium dimethylcuprate; only the β-keto sultones 26 and 27 have been isolated (84% yield). In contrast, under similar conditions the 3α-methanesulfonate 35 gave the 2-oxopropylsulfonyloxy derivatives 36 and 37. Synthesis of 3β-methylGA20 has been achieved via reaction of the 3α-trifluoromethane-sulfonate 38 with lithium dimethylcuprate. 3α-MethylGA20 and 3β-methylGA20 show similar activity to GA20 (and significantly less activity than GA3) in the stimulation of stem elongation of dwarf rice seedlings.

Organic Synthesis Using Sodium Bromate. II. A Facile Synthesis of N-Bromo Imides and Amides Using Sodium Bromate and Hydrobromic Acid (or Sodium Bromide) in the Presence of Sulfuric Acid

The reaction of imides and amides in water (or aqueous acetic acid) with sodium bromate and hydrobromic acid (or sodium bromide) in the presence of sulfuric acid under mild conditions gave the corresponding N-bromides in high yields.

Kinetics and mechanism of in situ bromohydrination of cinnamic acids by N-bromoacetamide

Bromohydrination of cinnamic acid (CA) and substituted CAs by N-bromoacetamide (NBA) has been studied in aqueous methanol medium, in the presence of mercuric acetate and acetamide (AA).The influence of substituents on the decomposition rate constant (k) of the adduct has been investigated.The thermodynamic parameters for the hydrolysis of NBA and adduct formation steps have been evaluated.The activation parameters for the first order decomposition of the adduct have also been calculated.The corresponding bromohydrins have been identified as the reaction products.

Solvent effects on kinetics of oxidation of dimethyl sulphoxide by N-bromoacetamide: An example of inner sphere oxygen atom transfer reaction

Rates of oxidation of DMSO by N-bromoacetamide (NBA) in neutral aqueous solution have been measured in the presence of acetamide (AA).The order in is one at -3, fractional when is between 0.01 and 0.5 mol dm-3 and zero when >0.5 mol dm-3.Different rate laws are operative under these three conditions though HOBr is the effective oxidising species in all the cases.The influence of the variation of solvent composition on the reaction rate has been studied by employing methanol-water binaries of various compositions.Thermodynamic parameters for the hydrolysis of NBA and adduct formation between HOBr and DMSO have been evaluated.The activation parameters for the first order decomposition of the adduct have also been calculated for various solvent compositions ranging from 0 to 80percent MeOH (v/v).The free energies of activation increase upon increasing the methanol content of the medium, whereas the enthalpies and entropies of activation show a more complex, but partially compensating behaviour.

Stereoselective process for preparing optically active alpha, beta-disubstituted carbonyl compounds

A stereoselective process is described for preparing optically active alpha,beta-disubstituted carbonyl campounds, comprising forming an acetal between an alpha,beta-unsaturated aldehyde or ketone and tartaric acid or a derivative thereof, halogenating the product thus obtained, and restoring the carbonyl compound.

HOMOLYTIC DISPLACEMENT AT CARBON CENTRES. XII. REGIOSPECIFIC FORMATION OF N-ALLYL AND N-CYCLOPROPYLCARBINYL SULPHONAMIDES AND OF ALLYL AND CYCLOPROPYL HALIDES IN THE REACTION OF N-HALOGENO COMPOUNDS WITH ORGANOCOBALOXIMES

Several but-3-enyl and allylcobaloximes react regiospecifically with N-chloro-N-methyl sulphonamides to give N-cyclopropylcarbinyl- or rearranged N-allyl-N-methyl sulphonamides, by a process which is believed to take place by the attack of an N-centred radical at the terminal unsaturated carbon of the organic ligand, with displacement of cobaloxime(II).In contrast, N-bromoacetamide and several other N-halogenoimides react regiospecifically to the cyclopropylcarbinyl halide or the rearranged allyl halide by a process in which a halogen-containing free radical species attacks the terminal unsaturated carbon of the organocobaloxime.

Kinetics and Mechanism of Oxidation of Formic Acid and Oxalic Acid by N-Bromoacetamide in Perchloric Acid Medium

The title reactions are first order each in N-bromoacetamide (NBA) and the substrates.The rate decreases linearly with an increase in and this is attributed to the formation of kinetically inactive hypobromous acidium ion, (H2OBr(+)).The reaction is retarded by added acetamide.Hypobromous acid has been postulated as the active oxidising species.Kinetic isotope effect is not present.In the mechanism proposed the rate-determining step involves formation of formyl or oxalyl hypobromite which then decomposes in a fast step to give the products, mostly CO2.