473-86-9

Basic information

• Product Name: 3-hydroxy-2-methyl-Butanoic acid
• Synonyms: 2-Methyl-3-hydroxybutyric acid;3-hydroxy-2-methyl-Butanoic acid;3-Hydroxy-2-methylbutyric acid;2,3-Dimethyl-3-hydroxypropionic acid;Nilic acid
• CAS NO: 473-86-9
• Molecular Formula: C₅H₁₀O₃
• Molecular Weight: 118.13
• Product Categories: Aliphatics
• Mol File: 473-86-9.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 237.6 °C at 760 mmHg
• Flash Point: 111.8 °C
• Appearance: /
• Density: 1.136 g/cm³
• Vapor Pressure: 0.00567mmHg at 25°C
• Refractive Index: 1.455
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• PKA: pK1:4.648 (18°C)
• CAS DataBase Reference: 3-hydroxy-2-methyl-Butanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-hydroxy-2-methyl-Butanoic acid(473-86-9)
• EPA Substance Registry System: 3-hydroxy-2-methyl-Butanoic acid(473-86-9)

Safety Data

• Hazardous Substances Data: 473-86-9(Hazardous Substances Data)

Usage

Chemical Properties

Pale orange Oil

Uses

3-Hydroxy-2-methylbutanoic Acid (cas# 473-86-9) is a compound useful in organic synthesis.

Definition

ChEBI: A 3-hydroxy monocarboxylic acid that is butyric acid which is substituted by a methyl group and a hydroxy group at positions 2 and 3, respectively.

InChI:InChI=1/C5H10O3/c1-3(4(2)6)5(7)8/h3-4,6H,1-2H3,(H,7,8)

Upstream product

• 609-14-3 2-acetylpropanoic acid ethyl ester 
• 684-84-4 2-methyl-1,3-butanediol 
• 124-38-9 carbon dioxide 
• 7732-18-5 water 
• 80-59-1 Tiglic acid 
• 90033-09-3 N-(2-t-butyldimethylsiloxyethyl)-2-methylacetoacetamide 
• 75-07-0 acetaldehyde 
• 27372-03-8 ethyl 3-hydroxy-2-methylbutyrate 
• 535-11-5 Ethyl 2-bromopropionate 
• 17094-21-2 2-methyl-acetoacetic acid methyl ester 
• 34293-67-9 methyl 3-(R)-hydroxy-2-(S)-methylbutanoate 

Downstream Products

• 80-59-1 Tiglic acid 
• 7732-18-5 water 

Relevant articles and documents

Glycolipid ester-type heterodimers from Ipomoea tyrianthina and their pharmacological activity

Tyrianthins A (1) and B (2), two new partially acylated glycolipid ester-type heterodimers were isolated from Ipomoea tyrianthina. Scammonic acid A was determined as the glycosidic acid in both monomeric units. Tyrianthin A (1) (IC50 0.24 ± 0.0

Methods for preparing antiviral calanolide compounds

The present invention relates to methods for preparing 2,2-dimethyl-5-acyloxy-10-propyl-2H,8H-benzo[1,2-b:3,4-b′]dipyran-8-one (5) and 2,2-dimethyl-5-hydroxy-10-propyl-2H,8H-benzo[1,2-b:3,4-b′]dipyran-8-one (6) and their use as intermediates for the synthesis of antiviral calanolide compounds. For example, Fries rearrangement on compound 5 or Friedel-Crafts reaction on 6, yields intermediate 2,2-dimethyl-5-hydroxy-6-propionyl-10-propyl-2H,8H-benzo[1,2-b:3,4-b′]dipyran-8-one (4), which, in turn, can be converted to (+)-calanolide A and (?)-calanolide B. The coupling of compound 6 with the appropriate chiral molecule under Mitsunobu or nucleophilic displacement leads to the asymmetric synthesis of antiviral calanolide compounds.

CHIRAL PROPIONATE ENOLATE EQUIVALENTS FOR THE STEREOSELECTIVE SYNTHESIS OF THREO- OR ERYTHRO-α-METHYL-β-HYDROXY ACIDS.

The aluminium and copper enolates derived from (n5-C5H5)Fe(CO)(PPh3)COCH2CH3 are chiral propionate enolate equivalents which on reaction with aldehydes (RCHO, R=Me, Et, iPr, tBu) provide stereoselective sytheses of threo-