79-15-2

Basic information

• Product Name: N-BROMOACETAMIDE
• Synonyms: ACETOBROMAMIDE;N-BROMOACETAMIDE (NBA);AcetaMide, N-broMo-;N-Bromoacetamide;N-BROMOACETAMIDE;NBAAcetobromamide;n-bromo-acetamid
• CAS NO: 79-15-2
• Molecular Formula: C₂H₄BrNO
• Molecular Weight: 137.96
• EINECS: 201-181-0
• Product Categories: Bromination;Halogenation;Synthetic Organic Chemistry
• Mol File: 79-15-2.mol
• Article Data: 11

Chemical Properties

• Melting Point: 102-105°C
• Boiling Point: 127-130 °C(Press: 16 Torr)
• Appearance: white to yellow/powder
• Density: 1.7000 (rough estimate)
• Refractive Index: 1.4740 (estimate)
• Storage Temp.: −20°C
• Solubility: very slightly in Chloroform
• PKA: 9.41±0.46(Predicted)
• Water Solubility: Soluble in water.
• Merck: 14,1398
• BRN: 969346
• CAS DataBase Reference: N-BROMOACETAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-BROMOACETAMIDE(79-15-2)
• EPA Substance Registry System: N-BROMOACETAMIDE(79-15-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: 3261
• WGK Germany: 3
• F: 8
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 79-15-2(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 79-15-2 differently. You can refer to the following data:
1. Abolishes the rapid inactivation of membrane sodium- and potassium-ion channels.
2. N-bromoacetamide annihilates the rapid inactivation of membrane sodium-ion channels. Also functions in the kinetics of cardiac sodium ion channels.

General Description

White powder.

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

Downstream Products

• 93-55-0 1-phenyl-propan-1-one 
• 145631-86-3 2-bromocyclohexyl acetate 
• 51-79-6 urethane 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 64341-49-7 1-bromo-3-buten-2-ol 
• 6607-46-1 (1,2-dibromovinyl)benzene 
• 123-11-5 4-methoxy-benzaldehyde 
• 1192-89-8 bromo(phenyl)mercury 
• 624-83-9 methyl isocyanate 
• 611-91-6 trans-2,3-dibromo-1,3-diphenylpropan-1-one 
• 6165-63-5 2,3-diphenyl-5-methyltetrazolium bromide 
• 594-34-3 1,2-dibromo-2-methyl-propane 
• 102921-26-6 (1,2-dibromoethyl)benzene 
• 2425-28-7 2-Bromo-1-phenylethanol 

Relevant articles and documents

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.

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.

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.