206996-51-2

Basic information

• Product Name: TERT-BUTYL (R)-(+)-2-HYDROXYBUTYRATE
• Synonyms: TERT-BUTYL (R)-(+)-2-HYDROXYBUTYRATE;TERT-BUTYL (R)-2-HYDROXYBUTYRATE;TERT-BUTYL (R)-(+)-2-HYDROXYBUTYRATE, 98 % (98% EE/GLC);(R)-tert-Butyl 2-hydroxybutanoate
• CAS NO: 206996-51-2
• Molecular Formula: C₈H₁₆O₃
• Molecular Weight: 160.21
• Product Categories: Chiral Building Blocks;Esters;Organic Building Blocks
• Mol File: 206996-51-2.mol

Chemical Properties

• Melting Point: 52-54 °C(lit.)
• Boiling Point: 179.1 ºC at 760 mmHg
• Flash Point: 58.8 ºC
• Appearance: /
• Density: 0.988 g/cm³
• Vapor Pressure: 0.286mmHg at 25°C
• Refractive Index: 1.435
• Storage Temp.: 2-8°C
• PKA: 13.07±0.20(Predicted)
• BRN: 5728525
• CAS DataBase Reference: TERT-BUTYL (R)-(+)-2-HYDROXYBUTYRATE(CAS DataBase Reference)
• NIST Chemistry Reference: TERT-BUTYL (R)-(+)-2-HYDROXYBUTYRATE(206996-51-2)
• EPA Substance Registry System: TERT-BUTYL (R)-(+)-2-HYDROXYBUTYRATE(206996-51-2)

Safety Data

• Hazard Codes: Xi
• Statements: 41
• Safety Statements: 26-39
• WGK Germany: 3
• F: 3
• Hazardous Substances Data: 206996-51-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
TERT-BUTYL (R)-(+)-2-HYDROXYBUTYRATE is used as a chiral building block for the synthesis of various pharmaceuticals. Its unique stereochemistry allows for the creation of enantiomerically pure compounds, which is crucial for the development of drugs with specific therapeutic effects and reduced side effects.
Used in Agrochemical Industry:
In the agrochemical industry, TERT-BUTYL (R)-(+)-2-HYDROXYBUTYRATE is utilized as a chiral building block in the production of agrochemicals. Its ability to create enantiomerically pure compounds contributes to the development of more effective and targeted pesticides and other agricultural chemicals.
Used in Food Industry:
TERT-BUTYL (R)-(+)-2-HYDROXYBUTYRATE is used as a flavoring agent in the food industry. Its unique properties allow it to impart specific flavors and enhance the taste of various food products, contributing to a more enjoyable consumer experience.
Used in Organic Synthesis:
TERT-BUTYL (R)-(+)-2-HYDROXYBUTYRATE is employed as a reagent in organic synthesis, where it serves as a versatile building block for the creation of a wide range of organic compounds. Its use in this field is driven by its ability to participate in various chemical reactions, enabling the synthesis of complex molecules for various applications.

InChI:InChI=1/C8H16O3/c1-5-6(9)7(10)11-8(2,3)4/h6,9H,5H2,1-4H3/t6-/m1/s1

Upstream product

• 37472-51-8 tert-butyl 2-oxybutanoate 

Relevant articles and documents

Selective Reductions. 37. Asymmetric Reduction of Prochiral Ketones with B-(3-Pinanyl)-9-borabicyclononane

The chiral trialkylborane B-(3-pinanyl)-9-borabicyclononane, either with the neat reagents or concentrated solutions, 2 M, reduces a wide range of prochiral carbonyl compounds with good to excellent asymmetric induction.Reduction of simple dialkyl ketones, 2-butanone, 2-octanone, 3-methyl-2-butanone, and 3,3-dimethyl-2-butanone, yields the corresponding alcohols with 43percent, 48percent, 62percent, and 0.7percent asymmetric induction.Acetophenone is reduced to 1-phenylethanol in 85percent ee.The α,β-unsaturated ketones 3-buten-2-one, 1-acetyl-1-cyclohexene, 3-methyl-2-cyclohexenone, and trans-4-phenyl-3-buten-2-one are reduced to the corresponding allylic alcohols with 57percent, 64percent, 11percent, and 97percent asymmetric induction, respecticvely.The α,β-conjugated acetylenic ketones 3-butyn-2-one, 4-methyl-1-pentyn-3-one, and 4-phenyl-3-butyn-2-one underwent a rapid reduction to afford the corresponding propargylic alcohols with 79percent, 99percent, and 91percent enantiomeric purities.The α-haloalkyl aromatic ketones α-chloroacetophenone, α-bromoacetophenone, α-iodoacetophenone, α,p-dibromoacetophenone, α-bromo-p-cyanoacetophenone,α-bromo-2'-acetonaphthone,and α,α,α-trifluoroacetophenone afforded the corresponding halohydrins with 96percent,93percent,93percent,96percent,96percent,90percent,and35percent enantiomeric purities, respectively.The corresponding aliphatic analogue 1-bromo-3-methyl-butanone gave the halohydrin in 66percent ee.The other isomer of this ketone, 3-bromo-3-methyl-2-butanone, failed to undergo reduction.Both the aliphatic and aromatic α-keto esters underwent rapid reduction to give the corresponding α-hydroxy esters with excellentenantiomeric excesses.Thus, methyl, ethyl, isopropyl, and tert-butyl pyruvates afforded the corresponding lactates with 86percent,83percent,78percent, and 92percent ee at 25 deg C,respectively.Lowering the reaction temperature to 0 deg C gave the tert-butyl lactate in 100percent ee.Other aliphatic α-keto esters such as metyl and ethyl 2-oxopentanoates, methyl 3-methyl-2-oxobutanoate, and ethyl 4-methyl-2-oxopentanoate were reduced to the corresponding α-hydroxy esters with 96percent, 96percent, 11percent, and 82percent ee.The methyl, isopropyl, and tert-butyl benzoylformates were reduced to the corresponding mendelic esters with 90percent, 96percent and 100percent ee, respectively.The reduction of the β-keto esters, however, proceeded slowly and ethyl acetoacetate gave the corresponding alcohol with 55percent ee.