42890-76-6

Basic information

• Product Name: (S)-1,2,4-Butanetriol
• Synonyms: (S)-Butane-1,2,4-triol;(S)-1,2,4-Butanetriol,95%,99% ee;(2S)-(-)-1,2,4-Trihydroxybutane;ASTM D6584 1,2,4-Butanetriol Solution ;(S)-(-)-1,2,4-BUTANETRIOL;(S)-1,2,4-BUTANETRIOL;(S)-(-)-1,2,4-TRIHYDROXYBUTANE;(2S)-BUTANE-1,2,4-TRIOL
• CAS NO: 42890-76-6
• Molecular Formula: C₄H₁₀O₃
• Molecular Weight: 106.12
• EINECS: -0
• Product Categories: Chiral Building Blocks;Simple Alcohols (Chiral);Synthetic Organic Chemistry;Chiral Building Blocks;Organic Building Blocks;Polyols
• Mol File: 42890-76-6.mol
• Article Data: 89

Chemical Properties

• Boiling Point: 150 °C0.04 mm Hg(lit.)
• Flash Point: >110°C
• Appearance: /
• Density: 1.19 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.475(lit.)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Sparingly), Water (Slightly)
• PKA: 14.02±0.20(Predicted)
• Water Solubility: soluble
• Sensitive: Hygroscopic
• BRN: 1719408
• CAS DataBase Reference: (S)-1,2,4-Butanetriol(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-1,2,4-Butanetriol(42890-76-6)
• EPA Substance Registry System: (S)-1,2,4-Butanetriol(42890-76-6)

Safety Data

• Hazard Codes: F,Xn
• Statements: 36/37/38-41-20/21/22-11
• Safety Statements: 23-24/25-39-26-16-36/37-28-33-29-9
• RIDADR: UN 3316 9/PG 2
• WGK Germany: 3
• F: 3-10-21
• Hazardous Substances Data: 42890-76-6(Hazardous Substances Data)

Usage

Description

(S)-1,2,4-Butanetriol, also known as (S)-(-)-1,2,4-Butanetriol, is a clear colorless viscous liquid that can be synthesized through the reduction of (S)-malic acid in the presence of borane-dimethyl sulfide. It serves as a crucial starting material in the enantioselective total syntheses of various organic compounds, including (+)-azimine and (+)-carpaine. Additionally, it is used to prepare organic building blocks such as (+)-3,4-epoxy-1-butanol, (2S,4S)-4-(hydroxymethyl)-2-ferrocenyl-1,3-dioxan, (S)-1,2,4-triacetoxybutane, and (S)-1,2,4-tris-(3,5-dinitrobenzoy1oxy)butane.

Uses

Used in Pharmaceutical Industry:
(S)-1,2,4-Butanetriol is used as a starting material for the enantioselective total syntheses of various pharmaceutical compounds, such as (+)-azimine and (+)-carpaine, due to its ability to facilitate the production of these compounds with specific stereochemistry.
Used in Chemical Synthesis:
(S)-1,2,4-Butanetriol is used as a building block for the preparation of various organic compounds, including (+)-3,4-epoxy-1-butanol, (2S,4S)-4-(hydroxymethyl)-2-ferrocenyl-1,3-dioxan, (S)-1,2,4-triacetoxybutane, and (S)-1,2,4-tris-(3,5-dinitrobenzoy1oxy)butane, which are essential in the development of new chemicals and materials.
Used in Research and Development:
(S)-1,2,4-Butanetriol is utilized as a research compound for studying its chemical properties and potential applications in various fields, including pharmaceuticals, materials science, and chemical engineering.
Used in Enzyme Regulation:

Upstream product

• 5055-09-4 (2S,2'RS) 2-O-(Tetrahydro-2'-pyranyl)-1,2,4-butanetriol 
• 636-61-3 D-Malic acid 
• 51267-44-8 (S)-3,4-dihydroxybutanoic acid 
• 3068-00-6 D,L-1,2,4-butanetriol 
• 51067-83-5 1,1-diphenyl-silolan-3-ol 
• 7724-28-9 (S)-hydroxy-succinaldehyde 
• 5469-16-9 4-Hydroxy-dihydro-furan-2-on 
• 108-88-3 toluene 
• 627-27-0 homoalylic alcohol 
• 66212-45-1 (2S)-2-hydroxy-butanedioic acid 1-mono methyl ester 
• 114818-97-2 (S)-1,4-dibenzyloxy-2-butanol 
• 97-67-6 (S)-Malic acid 
• 488-30-2 D-xylonic acid 
• 136264-10-3 ((R)-2-Isopropyl-[1,3]dioxan-4-yl)-methanol 

Downstream Products

• 97678-48-3 (S)-1,4-bis-trityloxy-butan-2-ol 
• 93464-99-4 3,5-Dinitro-benzoic acid (S)-2-(1,4-dioxa-spiro[4.5]dec-2-yl)-ethyl ester 
• 103773-79-1 [(2S,4S)-2-phenyl-1,3-dioxan-4-yl]methanol 
• 157423-40-0 (S)-1-azido-2,4-O-benzylidenebutane 
• 99520-83-9 (-)-(S)-butane-1,2,4-triyl tris(p-toluenesulfonate) 
• 6414-28-4 (S)-1,2,4-butanetriol-1,2-cyclic carbonate 
• 151223-12-0 (S)-2,2-diisopropyl-4-(2-hydroxyethyl)dioxolane 
• 85418-23-1 (S)-1-O-benzyl-1,2,4-butanetriol 
• 114818-97-2 (S)-1,4-dibenzyloxy-2-butanol 
• 165450-03-3 (3S)-3,4-bis-benzyloxy-butan-1-ol 
• 223382-94-3 (2R,4S)-2-methyl-2-phenyl-1,3-dioxolan-4-ethanol 
• 223382-93-2 (2R,4S)-2-methyl-2-phenyl-1,3-dioxan-4-methanol 
• 223382-92-1 (2S,4S)-2-methyl-2-phenyl-1,3-dioxan-4-methanol 
• 187102-96-1 (2R,4S)-2-phenyl-1,3-dioxolan-4-ethanol 

Relevant articles and documents

Blasticidin A as an inhibitor of aflatoxin production by Aspergillus parasiticus

Blasticidin A, an antibiotic, showed strong inhibitory activity toward aflatoxin production by Aspergillus parasiticus. Its structure was characterized by NMR and chemical degradation experiments as 1, which is a tetramic acid derivative with a highly oxygenated long alkyl chain similar to aflastatin A (2). Absolute configurations of the eight chiral centers at C-4, 6, 31, 32, 33, 34, 35 and 37 of 1 were chemically determined. Blasticidin A almost completely inhibited aflatoxin production at 0.5 μm.

Development of an Efficient Process for the Decomposition of the Borate Complexes Formed during the Large-Scale Synthesis of (S)-1,2,4-Butanetriol

An improved multikilogram-scale process for the production of (S)-1,2,4-butanetriol has been developed. This process involves the efficient removal of residual boric acid and the decomposition of the borate complexes formed during the reduction of (-)-dimethyl malate with sodium borohydride by methanolysis using a circular distillation-coupled hydrolysis apparatus.

Optically active isonitrile ligand for palladium-catalyzed enantioselective bis-silylation of carbon-carbon double bonds

Intramolecular bis-silylation of homoallylic alcohols proceeded enantioselectively in the presence of a catalyst prepared from Pd(acac), and optically active isonitriles, derived from a common chiral source, (+)-ketopinic acid.

IMMUNOMODULATORY GLYCOSPHINGOLIPIDS AND METHODS OF USE THEREOF

Provided herein are a subset of alpha-galactosylceramide (alpha-GC) compounds having improved immunomodulatory activity, particularly with respect to NKT cell number and activity. Also provided herein are methods of use of such compounds, including in the modulation of NKT cells and/or activity in vivo. Further provided are combinatorial synthesis methods for generating alpha-GC compounds of specifically defined structure and thereby generating pure preparations thereof.

A S - (+) -3 - hydroxy tetrahydrofuran chemical synthesis method

The invention discloses a S - (+) - 3 - hydroxy tetrahydrofuran chemical synthesis method, includes the following operation steps: 1, compound 1 in the presence of thionyl chloride and methanol reaction to obtain compound 2; 2, in the solvent, compound 2 in the presence of a reducing agent and the reaction to obtain compound 3; 3, compound 3 in the presence of paratoluene sulfonic acid, reaction to obtain compound S - (+) - 3 - hydroxy tetrahydrofuran.