(S)-2-methylbutanal

Base Information

• Chemical Name: (S)-2-methylbutanal
• CAS No.: 1730-97-8
• Molecular Formula: C5H10 O
• Molecular Weight: 86.1338
• DSSTox Substance ID: DTXSID801346324
• Nikkaji Number: J51.972C
• Wikidata: Q27160271
• Metabolomics Workbench ID: 44927
• Mol file: 1730-97-8.mol

Synonyms:(S)-2-methylbutanal;(2S)-2-methylbutanal;(S)-2-methylbutyraldehyde;1730-97-8;S-2-METHYLBUTANAL;(2S)-2-methylbutyraldehyde;(s)-(+)-2-methylbutanal;(S)-2-methylbutyric aldehyde;(2S)-2-methylbutyric aldehyde;(S)-alpha-methylbutyric aldehyde;CHEBI:88414;BYGQBDHUGHBGMD-YFKPBYRVSA-N;DTXSID801346324;Q27160271

Chemical Property of (S)-2-methylbutanal

Chemical Property:

• Boiling Point: 90-92 °C
• PSA: 17.07000
• Density: 0.7988 g/cm3
• LogP: 1.23140
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 86.073164938
• Heavy Atom Count: 6
• Complexity: 41.2

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C)C=O
• Isomeric SMILES: CC[C@H](C)C=O
• General Description: (S)-2-Methylbutanal is a chiral aldehyde used in stereoselective reactions, particularly in studies involving diastereofacial selectivity. It serves as a reactant in carbonyl allylation processes, where its chirality influences the stereochemical outcome of the reaction. S-2-Methylbutanal is valuable in synthesizing stereochemically complex molecules, such as macrolide and polyether antibiotics, due to its ability to participate in highly selective transformations when paired with appropriate chiral reagents.

Technology Process of (S)-2-methylbutanal

There total 9 articles about (S)-2-methylbutanal which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 6.0%

(2S)-2-methyl-1-butanol (1565-80-6) → (S)-2-methylbutyraldehyde (1730-97-8) + butanone (78-93-3)

Guidance literature:

With potassium chromate; sulfuric acid; tetra(n-butyl)ammonium hydrogensulfate; In dichloromethane; at -15 ℃; for 1h; Yield given. Title compound not separated from byproducts;

Reference yield:

glycyl-glycyl-L-isoleucyl-L-proline → formaldehyd (50-00-0,30525-89-4,61233-19-0) + (S)-2-methylbutyraldehyde (1730-97-8) + 4-aminobutyraldehyde (4390-05-0) + carbon dioxide (124-38-9,18923-20-1)

Guidance literature:

With sodium acetate; manganese triacetate; In water; at 24.84 ℃; Further Variations:; Reagents; Temperatures; Kinetics;

DOI:10.1002/kin.20144

Reference yield:

(Z)-2-Butene (590-18-1) + carbon monoxide (201230-82-2) → pentanal (110-62-3) + (S)-2-methylbutyraldehyde (1730-97-8) + (R)-2-methylbutanal (33204-48-7)

Guidance literature:

With hydrogen; Rh(I)-(R,S)-BINAPHOS; at 60 ℃; for 2h; under 20520 Torr; Title compound not separated from byproducts;

DOI:10.1021/ja034447u

upstream raw materials:

(2S)-2-methyl-1-butanol

1-butylene

carbon monoxide

(Z)-2-Butene

Downstream raw materials:

L-isoleucine

D-alloisoleucine

(2S)-2-methyl-1-butanol

3-methyl-3-hexanol

Refernces

Charge Reversal of Electrophilic ?-Allylpalladium Intermediates: Carbonyl Allylation bu Allylic Acetates with Pd(PPh3)4-Zn

10.1021/jo00392a044

The research focuses on the synthesis and reaction of chiral aldehydes with specific reagents to study diastereofacial selectivity. The purpose is to explore the factors controlling aldehyde facial selectivity using crotyldiisopinocampheylboranes (13-16) with chiral aldehydes (17 and 18). The reactions were highly stereoselective, yielding products with high facial selectivities. The study concludes that the chirality of the reagent controls the overall diastereofacial selectivity in the reaction, allowing access to all possible stereoisomers in high optical purity by selecting the proper antipode of the reagents and aldehydes. This method could be a convenient route for synthesizing macrolide and polyether antibiotics. (S)-2-Methylbutanal and (S)-2-(benzyloxy)propanal are chiral aldehydes used as reactants to study diastereoselectivity.