4216-96-0

Basic information

• Product Name: tert-Butyl (R)-2-hydroxy-3-methylbutyrate
• Synonyms: tert-Butyl (R)-2-hydroxy-3-methylbutyrate;(R)-tert-butyl 2-hydroxy-3-Methylbutanoate;tert-butyl (2R)-2-hydroxy-3-methylbutanoate
• CAS NO: 4216-96-0
• Molecular Formula: C₉H₁₈O₃
• Molecular Weight: 174.24
• Mol File: 4216-96-0.mol
• Article Data: 3

Chemical Properties

• Melting Point: 28-30 °C(Solv: ligroine (8032-32-4))
• Boiling Point: 189.5°C at 760 mmHg
• Flash Point: 63°C
• Appearance: /
• Density: 0.974g/cm³
• Vapor Pressure: 0.155mmHg at 25°C
• Refractive Index: 1.437
• Storage Temp.: 2-8°C
• PKA: 12.94±0.20(Predicted)
• CAS DataBase Reference: tert-Butyl (R)-2-hydroxy-3-methylbutyrate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-Butyl (R)-2-hydroxy-3-methylbutyrate(4216-96-0)
• EPA Substance Registry System: tert-Butyl (R)-2-hydroxy-3-methylbutyrate(4216-96-0)

Safety Data

• Hazardous Substances Data: 4216-96-0(Hazardous Substances Data)

Usage

General Description

Tert-butyl (R)-2-hydroxy-3-methylbutyrate is a chemical compound with the molecular formula C9H18O3. It is a colorless liquid with a fruity odor, commonly used as a flavoring agent in food and beverages. This chemical is a derivative of butyric acid and is commonly found in nature as an ester in fruits and essential oils. Tert-butyl (R)-2-hydroxy-3-methylbutyrate is also used in the production of perfumes and cosmetics due to its pleasant aroma. Additionally, it is used as a solvent in various industrial applications.

InChI:InChI=1/C9H18O3/c1-6(2)7(10)8(11)12-9(3,4)5/h6-7,10H,1-5H3/t7-/m1/s1

Upstream product

• 110-78-1 Propyl isocyanate 
• 2528-17-8 α-hydroxy-isovaleric acid t-butyl ester 
• 640-68-6 D-Val-OH 
• 44976-78-5 (R)-2-acetoxy-3-methylbutanoic acid 
• 111505-47-6 (S)-2-Chloro-4-methyl-pentanoic acid tert-butyl ester 
• 111505-51-2 4-Nitro-benzoic acid (R)-1-tert-butoxycarbonyl-3-methyl-butyl ester 
• 3339-42-2 O-Benzyloxycarbonyl-D-α-hydroxy-isovaleriansaeure 
• 115-11-7 isobutene 
• 868740-08-3 D-α-Acetoxy-isovaleriansaeure-tert-butylester 

Downstream Products

• 2441-60-3 Z-L-Valyl-D-α-oxy-isovaleryl-N-methyl-L-valyl-D-α-oxy-isovaleryl-N-methyl-L-valyl-D-α-oxy-isovaleriansaeure-tert.-butylester 
• 2374-76-7 Z-L-Valyl-D-α-oxy-isovaleryl-L-valyl-D-α-oxy-isovaleryl-L-valyl-D-α-oxy-isovaleriansaeure-tert.-butylester 
• 95866-68-5 Z-N-Methyl-L-isoleucyl-D-α-hydroxy-isovaleriansaeure 
• 18671-27-7 N-Benzyloxycarbonyl-N-methyl-L-Val-D-α-hydroxy-isovaleryl-N-methyl-L-Val-D-α-hydroxy-isovaleryl-N-methyl-L-Val-D-α-hydroxy-isovaleriansaeure-tert.-butylester 
• 2752-05-8 Z-L-Valyl-D-α-oxy-isovaleryl-L-valyl-D-α-oxy-isovaleriansaeure-tert.-butylester 
• 2444-08-8 Z-L-Valyl-D-α-oxy-isovaleriansaeure 
• 18671-23-3 N-Benzyloxycarbonyl-N-methyl-D-Val-D-α-hydroxy-isovaleryl-N-methyl-D-Val-D-α-hydroxy-isovaleriansaeure-tert.-butylester 
• 18671-23-3 N-Benzyloxycarbonyl-N-methyl-L-Val-D-α-hydroxy-isovaleryl-N-methyl-L-Val-D-α-hydroxy-isovaleriansaeure-tert.-butylester 
• 18668-12-7 N-Benzyloxycarbonyl-N-methyl-L-Val-D-α-hydroxy-isovaleriansaeure 
• 18668-12-7 N-Benzyloxycarbonyl-N-methyl-D-Val-D-α-hydroxy-isovaleriansaeure 
• 4357-27-1 p-Nitro-benzyloxycarbonyl-N-methyl-L-leucin--ester 

Relevant articles and documents

Kinetic resolution of racemic α-tert-alkyl-α-hydroxy esters by enantiomer-selective carbamoylation

Kinetic resolution of sterically hindered racemic α-tert-alkyl- α-hydroxy esters is performed by enantiomer-selective carbamoylation with the t-Bu-Box-Cu(II) catalyst (Box = bis-(oxazoline)). The reaction with 0.5 equiv of n-C3H7NCO is carried out with a substrate-to-catalyst molar ratio of 500-5000 at -20 to 25 °C. The high enantiomer-discrimination ability of the catalyst achieves an excellent stereoselectivity factor (s = kfast/kslow) of 261 in the best case. A catalytic cycle for this reaction is proposed (Figure presented).

The structure of enniatins and related antibiotics.

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