206358-12-5

Basic information

• Product Name: (R)-2-hydroxybutanamide
• Synonyms: (R)-2-hydroxybutanamide
• CAS NO: 206358-12-5
• Molecular Formula: C4H9NO2
• Molecular Weight: 103.11976
• Mol File: 206358-12-5.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (R)-2-hydroxybutanamide(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-hydroxybutanamide(206358-12-5)
• EPA Substance Registry System: (R)-2-hydroxybutanamide(206358-12-5)

Safety Data

• Hazardous Substances Data: 206358-12-5(Hazardous Substances Data)

Usage

Description

(R)-2-hydroxybutanamide, also known as 2-hydroxybutyramide, is an organic compound with the molecular formula C4H9NO2. It exists as a white, crystalline solid at room temperature and is recognized for its role as a chiral building block in organic chemistry. (R)-2-hydroxybutanamide is primarily utilized as an intermediate in the pharmaceutical industry for the production of various drugs and organic compounds, showcasing its versatility and usefulness in chemical and pharmaceutical processes.

Uses

Used in Pharmaceutical Industry:
(R)-2-hydroxybutanamide is used as an intermediate for the synthesis of pharmaceuticals, contributing to the development of new drugs and medications. Its unique structure and properties make it a valuable component in the creation of various medicinal compounds.
Used in Organic Chemistry:
(R)-2-hydroxybutanamide serves as a chiral building block in organic chemistry, playing a crucial role in the synthesis of other organic compounds. Its presence in chemical reactions can lead to the development of novel substances with potential applications in various industries.
Used in Drug Development:
(R)-2-hydroxybutanamide holds potential applications in the development of new drugs and pharmaceuticals, thanks to its structural characteristics and reactivity. Its use in drug development can lead to the creation of innovative treatments and therapies for various medical conditions.

Upstream product

• 80-58-0 2-Bromobutyric acid 
• 77287-34-4 formamide 
• 74-90-8 hydrogen cyanide 
• 123-38-6 propionaldehyde 
• 4476-02-2 2-hydroxybutanenitrile 
• 73349-08-3 methyl (S)-2-hydroxybutyrate 
• 625-37-6 crotonamide 

Relevant articles and documents

Highly stereoselective hydrocyanation of optically pure α- sulfinylaldehydes

Diastereoselective hydrocyanation of enantiomerically pure 2-p-tolyl- sulfinylacetaldehyde and 2-p-tolylsulfinylpropanal with Et2AlCN catalyzed by ZnBr2 is described. The sulfur configuration controls the stereochemical course of the reaction. Hydrolysis of the resulting cyanohydrins and further desulfurization yielded the corresponding α-hydroxyamides in high ees (90%).

Bis(allyl)-ruthenium(IV) complexes with phosphinous acid ligands as catalysts for nitrile hydration reactions

Several mononuclear ruthenium(iv) complexes with phosphinous acid ligands [RuCl2(η3:η3-C10H16)(PR2OH)] have been synthesized (78-86% yield) by treatment of the dimeric precursor [{RuCl(μ-Cl)(η3:η3-C10H16)}2] (C10H16 = 2,7-dimethylocta-2,6-diene-1,8-diyl) with 2 equivalents of different aromatic, heteroaromatic and aliphatic secondary phosphine oxides R2P(O)H. The compounds [RuCl2(η3:η3-C10H16)(PR2OH)] could also be prepared, in similar yields, by hydrolysis of the P-Cl bond in the corresponding chlorophosphine-Ru(iv) derivatives [RuCl2(η3:η3-C10H16)(PR2Cl)]. In addition to NMR and IR data, the X-ray crystal structures of representative examples are discussed. Moreover, the catalytic behaviour of complexes [RuCl2(η3:η3-C10H16)(PR2OH)] has been investigated for the selective hydration of organonitriles in water. The best results were achieved with the complex [RuCl2(η3:η3-C10H16)(PMe2OH)], which proved to be active under mild conditions (60 °C), with low metal loadings (1 mol%), and showing good functional group tolerance.

Synthesis of aliphatic (S)-α-hydroxycarboxylic amides using a one-pot bienzymatic cascade of immobilised oxynitrilase and nitrile hydratase

A one-pot bienzymatic cascade combining a hydroxynitrile lyase (Manihot esculenta, E.C. 4.1.2.10) and a nitrile hydratase (Nitriliruptor alkaliphilus, E.C. 4.2.1.84) for the synthesis of enantiopure aliphatic α- hydroxycarboxylic amides from aldehydes is described. Both enzymes were immobilised as cross-linked enzyme aggregates (CLEAs). Stability tests show that the nitrile hydratase CLEAs are sensitive to water-immiscible organic solvents as well as to aldehydes and hydrogen cyanide (HCN), but are remarkably stable and show useful activity in acidic aqueous environments of pH 4-5. The cascade reactions are consequently carried out by using a portionwise feed of HCN and moderate concentrations of aldehyde in acidic aqueous buffer to suppress the uncatalysed hydrocyanation background reaction. After optimisation, this method was used to synthesise five different kinds of aliphatic α- hydroxycarboxylic amides from the corresponding aldehydes with good yields and with enantiomeric purities comparable to those obtained for the α-hydroxynitriles in the microaqueous hydrocyanation using hydroxynitrile lyase and an excess of HCN.