37505-02-5

Basic information

• Product Name: (R)-2-HYDROXY-2-METHYLBUTYRIC ACID
• Synonyms: (R)-2-HYDROXY-2-METHYLBUTYRIC ACID;(R)-2-Hydroxy-2-methylbutanoic acid;(R)-2-Methyl-2-hydroxybutanoic acid
• CAS NO: 37505-02-5
• Molecular Formula: C₅H₁₀O₃
• Molecular Weight: 118.13
• Mol File: 37505-02-5.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 237.6 °C at 760 mmHg
• Flash Point: 111.8 °C
• Appearance: /
• Density: 1.144 g/cm³
• CAS DataBase Reference: (R)-2-HYDROXY-2-METHYLBUTYRIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-HYDROXY-2-METHYLBUTYRIC ACID(37505-02-5)
• EPA Substance Registry System: (R)-2-HYDROXY-2-METHYLBUTYRIC ACID(37505-02-5)

Safety Data

• Hazardous Substances Data: 37505-02-5(Hazardous Substances Data)

Usage

Description

(R)-2-HYDROXY-2-METHYLBUTYRIC ACID, also known as (R)-(-)-2-Hydroxy-2-methylbutyric Acid, is an organic compound derived from (S)-(-)-1-(1-Naphthyl)ethylamine (N368460). It is characterized by its chiral structure and plays a significant role in various chemical reactions and applications due to its unique properties.

Uses

Used in Chiral/Asymmetric Synthesis:
(R)-2-HYDROXY-2-METHYLBUTYRIC ACID is used as a key intermediate in the asymmetric synthesis of α-cyanocarboxylates. Its chiral nature allows for the creation of enantiomerically pure compounds, which are essential in the development of pharmaceuticals and other specialty chemicals.
Used in Organometallic Catalysis:
In the field of organometallic catalysis, (R)-2-HYDROXY-2-METHYLBUTYRIC ACID is utilized in the synthesis of chiral imidazolin-2-ylidene ligands. These ligands are crucial for enhancing the selectivity and efficiency of catalytic reactions, leading to the production of high-quality enantiomerically pure compounds with potential applications in various industries, including pharmaceuticals, agrochemicals, and fine chemicals.

Upstream product

• 3739-30-8 2-hydroxy-2-methylbutyric acid 
• 63742-08-5 1-((E)-2-methyl-but-2-enoyl)-L-proline 
• 33212-19-0 (R)-2,2-dimethoxy-3-methyl-pentan-3-ol 
• 63742-11-0 (3S,8aS)-3-ethyl-3-methyl-1,4-dioxo-3,4,6,7,8,8a-hexahydro-1H-pyrrolo<2,1-c><1,4>oxazine 
• 107365-39-9 (R)-2-tert-Butoxy-N-((S)-1-methoxymethyl-2,2-dimethyl-propyl)-2,N-dimethyl-butyramide 
• 107365-49-1 (R)-2-(tert-Butyl-dimethyl-silanyloxy)-N-((S)-1-methoxymethyl-2-methyl-propyl)-2-methyl-butyramide 
• 81286-85-3 (2S,5R)-2-(tert-butyl)-5-ethyl-5-methyl-1,3-dioxolan-4-one 
• 74-90-8 hydrogen cyanide 
• 78-93-3 butanone 
• 256393-12-1 (1S,2S,5'R)-N,N-diisopropyl [2-spiro-2'-(5'-ethyl-5'-methyl-1',3'-dioxolane-4'-one)-7,7-dimethylbicyclo[2.2.1]hept-1-yl]methanesulfonamide 
• 63742-15-4 (3S,8aS)-3-<(R)-bromoethyl>-3-methyl-1,4-dioxo-3,4,6,7,8,8a-hexahydro-1H-pyrrolo<2,1-c><1,4>oxazine 
• 39939-14-5 (R)-3-methyl-1-pentyn-3-ol hydrogen phthalate 
• 4111-08-4 2-hydroxy-2-methyl-butyronitrile 

Downstream Products

• 129189-51-1 2-Hydroxy-N-[2-(2-hydroxy-2-methyl-butyrylamino)-phenyl]-2-methyl-butyramide 
• 98779-35-2 (R)-2-Methyl-1,1-diphenyl-butane-1,2-diol 
• 133562-45-5 (R)-2-benzyloxy-2-methylbutanoic acid 
• 1229447-56-6 R-2-(4-nitro-phenoxy)-2-methylbutanoic acid 

Relevant articles and documents

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Process for preparing optically active α-hydroxy acids and derivatives thereof

The present invention provides a process for preparing optically active α-hydroxy acids and derivatives thereof by subjecting the alkylated 1,3-dioxolanones of formula (IV) wherein R1and R2are the same or different and are each independently H or C1-6alkyl; R5is H, C1-16alkyl, or unsubstituted or substituted phenyl; and R6is C1-8alkyl, C2-7alkenyl or unsubstituted or substituted benzyl, to either alcoholysis or hydrolysis, in which the alkylated 1,3-dioxolanones are obtained by using 10-camphorsulfonamide as a chiral auxiliary.

Stereoelectronic Control of the Tertiary Ketol Rearrangement: Implications for the Mechanism of the Reaction Catalysed by the Enzymes of Branched-chain Amino Acid Metabolism, Reductoisomerase and Acetolactate Decarboxylase

The alkali-catalised rearrangement of (R)--3-hydroxy-3-methylpentan-2-one has been studied.Rearrangement via transition state having an anti arrangement of C-O bonds was preferred over that with a syn arrangement by a factor of 1.8:1.The result is of interest in relation to the mechanism of action of the enzymes reductoisomerase and acetolactate decarboxylase, both of which are involved in the metabolism of the branched-chain amino acids.The structure and relative configuration of the product 23 of bromolactonisation of N-methacryloyl L-proline 22 were determined by X-ray crystallographic analysis.