ChemicalBook CAS DataBase List 3-Bromopropionic acid

3-Bromopropionic acid synthesis

11synthesis methods

Product Name:3-Bromopropionic acid
CAS Number:590-92-1
Molecular formula:C3H5BrO2
Molecular Weight:152.97

3-Bromopropionic acid is prepared by reacting acrylonitrile with hydrogen bromide to obtain bromopropionitrile and then hydrolyzing it. Add acrylonitrile to boiling hydrobromic acid, reflux at 130°C for 6 hours, extract the solid obtained by filtration with ethanol, and obtain the crude product after recovering ethanol by distillation under reduced pressure. By heating 2-cyanoethanol and 40% hydrobromic acid to reflux for 2h, 3-bromopropionic acid can also be produced with a yield of over 80%.

598-72-1 Synthesis

598-72-1
347 suppliers
$15.00/25g

590-92-1
239 suppliers
$10.00/1g

Yield:590-92-1 79%

Reaction Conditions:

with tetrabutyl phosphonium bromide at 160; under 760.051 Torr; for 20 h;

Steps:

61 EXAMPLE 61 - 3-BrPA synthesis from 2-BrPA with [PBu4IBr molten salt catalyst
46.23 g of solid tetrabutylphosphonium bromide ([PBu4IBr; 133.5 mmol, 98%; Sigma-Aldrich Chemie GmbH, Taufkirchen, Germany; catalog 189138) were mixed with 20.68g of liquid 2-bromopropionic acid (2-BrPA; 133.5 mmol, 99%; Sigma-Aldrich Chemie GmbH, Taufkirchen, Germany; catalog B78300) in a 100 mL three-necked glass reactor in a molar ratio of 1:1 at room temperature and atmospheric conditions. The isomerization mixture was heated to 160°C under continuous stirring with a magnetic stirring bar at a speed of 450 rpm. Theisomerization mixture was batchwise refluxed and gaseous by-products were routed to the off-gas or collected in a hydrostatic colunm. After an overall process time of 20 h, the hot reaction mixture was allowed to cool down to room temperature and was analyzed via off-line ‘H NMR (JEOL ECX 400 MHz). ‘H qNMR analysis of the isomerization mixture gave a 3-bromopropionic acid (3- BrPA) yield of about 79 mol% and selectivity of more than about 90 mol%.

References:

THE PROCTER & GAMBLE COMPANY;ALBERT, Jakob;WASSERSCHEID, Peter;TACCARDI, Nicola;NAGENGAST, Jens;KEHRER, Matthias;KADAR, Julian;COLLIAS, Dimitris, Ioannis WO2018/22826, 2018, A1 Location in patent:Page/Page column 67

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802294-64-0 Synthesis