n-Bromoacetamide

Base Information

• Chemical Name: n-Bromoacetamide
• CAS No.: 79-15-2
• Molecular Formula: C2H4BrNO
• Molecular Weight: 137.964
• Hs Code.: 29299090
• European Community (EC) Number: 201-181-0
• UN Number: 3261
• UNII: 0AQ6MWH7ZB
• DSSTox Substance ID: DTXSID5024633
• Nikkaji Number: J4.228E
• Wikidata: Q27236544
• ChEMBL ID: CHEMBL1256514
• Mol file: 79-15-2.mol

Synonyms:N-bromoacetamide

Chemical Property of n-Bromoacetamide

Chemical Property:

• Appearance/Colour: White to yellowish powder
• Melting Point: 102-105°C
• Refractive Index: 1.474
• Boiling Point: 127-130 °C(Press: 16 Torr)
• PKA: 9.41±0.46(Predicted)
• PSA: 29.10000
• Density: 1.71 g/cm³
• LogP: 0.82330
• Storage Temp.: −20°C
• Solubility.: very slightly in Chloroform
• Water Solubility.: Soluble in water.
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 136.94763
• Heavy Atom Count: 5
• Complexity: 44.9
• Transport DOT Label: Corrosive

Purity/Quality:

99% ^*data from raw suppliers

N-bromoacetamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)NBr
• General Description: N-Bromoacetamide (NBA) is a versatile reagent used in organic synthesis, particularly in the one-pot synthesis of 2-oxazolines from ethyl α-cyanocinnamate derivatives, where it acts as a brominating agent under mild conditions (room temperature, acetone) without requiring inert gas protection. It facilitates the formation of aminobrominated intermediates, leading to cyclization with high yields (up to 98%). Additionally, NBA is employed in the stereoselective synthesis of glucal epoxides via bromohydrin cyclization, demonstrating its utility in carbohydrate chemistry. Its reactivity can be modulated by reaction conditions, influencing diastereoselectivity and product outcomes.

Technology Process of n-Bromoacetamide

There total 9 articles about n-Bromoacetamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

acetamide (60-35-5) → N-bromoacetamide (79-15-2)

Guidance literature:

With sodium bromate; sulfuric acid; sodium bromide; In water; for 0.5h; Ambient temperature;

DOI:10.1246/bcsj.66.2426

Reference yield:

N,N-dibromoacetamide (598-93-6) + water (7732-18-5) → acetamide (60-35-5) + hypobromous acid (15656-19-6,13517-11-8) + N-bromoacetamide (79-15-2)

Guidance literature:

beim Kochen;

Reference yield:

sodium acetylamide (2620-30-6) → N-bromoacetamide (79-15-2)

Guidance literature:

With bromine; In water;

DOI:10.1016/0022-328X(87)80163-8

upstream raw materials:

acetamide

N,N-dibromoacetamide

sodium acetylamide

ent-13-Acetoxy-3-oxo-20-norgibberella-1⁽¹⁰⁾,16-diene-7,19-dioic acid 7,19-dimethyl ester

Downstream raw materials:

2-bromothiophene

2,5-dibromothiophen

1-phenyl-propan-1-one

N-Bromosuccinimide

Refernces

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

10.1002/jhet.1902

The research focuses on the development of an efficient one-pot synthesis method for 2-oxazoline derivatives from ethyl α-cyanocinnamate derivatives using N-bromoacetamide (NBA) and potassium phosphate (K3PO4) as the base. The study was conducted at room temperature in acetone without the need for inert gas protection. The reaction yields were good to excellent (up to 98%) and were completed within 4.5 hours. A total of 13 examples were investigated, and the substrates were varied to include electron-donating and electron-withdrawing groups to assess the reaction's scope and limitations. The analysis involved monitoring the reaction progress using thin-layer chromatography (TLC) and determining the structures of the products through nuclear magnetic resonance (NMR) spectroscopy and high-resolution mass spectrometry (HRMS). The reaction mechanism was proposed based on the observed intermediates and the regioselectivity of the reaction, involving an aminobrominated intermediate and a cyclization process. The research also included the preparation of single crystals for X-ray crystallographic analysis to confirm the regiospecifity of the 2-oxazoline products.

Stereoselective Glucal Epoxide Formation

10.1021/jo00066a032

The research focuses on the stereoselective formation of glucal epoxides, which are crucial intermediates in the synthesis of oligosaccharides and other carbohydrate derivatives. The study aimed to find an alternative approach to the existing method of dimethyldioxirane (DMD) oxidation, which has limitations such as the need for rigorous drying and difficulty in scaling up. The researchers explored the cyclization of bromohydrins as a route to glucal epoxide formation, using chemicals such as N-bromoacetamide (NBA), sodium hydride (NaH), potassium hydride (KH), 18-crown-6, sodium phenylthiolate, sodium azide, methoxide, and benzyloxide. They observed that the reaction conditions significantly affected the diastereoselectivity of the epoxide formation, leading to different ratios of a-manno and β-gluco products. The study concluded that the formation and cyclization of bromohydrins offer an alternative route for glucal epoxide synthesis, with potential applications to other carbohydrate substrates, and highlighted the importance of metal ions and solvents in modifying the relative reactivities of the anomeric alkoxides, which influence the stereoselectivity of the cyclization process.