33106-32-0

Basic information

• Product Name: (S)-2-(Benzyloxy)propanoic acid
• Synonyms: (S)-2-(Benzyloxy)propanoic acid;(S)-2-(Benzyloxy)propionic acid;[S,(-)]-2-(Benzyloxy)propionic acid;(S)-(-)-O-Benzyllactic acid;O-Benzyl(S)-lactic acid;O-Benzyl-L-lactic acid;Propanoic acid, 2-(phenylMethoxy)-, (2S)-
• CAS NO: 33106-32-0
• Molecular Formula: C₁₀H₁₂O₃
• Molecular Weight: 180.20048
• Mol File: 33106-32-0.mol
• Article Data: 34

Chemical Properties

• Boiling Point: 328℃
• Flash Point: 130℃
• Appearance: /
• Density: 1.150
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (S)-2-(Benzyloxy)propanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-(Benzyloxy)propanoic acid(33106-32-0)
• EPA Substance Registry System: (S)-2-(Benzyloxy)propanoic acid(33106-32-0)

Safety Data

• Hazardous Substances Data: 33106-32-0(Hazardous Substances Data)

Usage

General Description

(S)-2-(Benzyloxy)propanoic acid is a chemical compound with the molecular formula C11H12O3. It is a carboxylic acid and is commonly used in organic synthesis as a chiral building block. The compound has a chiral center and exists as a pair of enantiomers, with the (S)-enantiomer being the one with the benzyloxy group on the left side of the carbon chain. (S)-2-(Benzyloxy)propanoic acid has applications in the pharmaceutical industry, where it is used as an intermediate in the synthesis of various pharmaceuticals, as well as in the research and development of new drugs. Overall, (S)-2-(Benzyloxy)propanoic acid is an important organic compound with various applications in both industry and research.

Upstream product

• 56-41-7 L-alanin 
• 100-51-6 benzyl alcohol 
• 338-69-2 D-Alanine 
• 74-83-9 methyl bromide 
• 30379-55-6 benzyloxyacetic acid 
• 33106-32-0 2-(benzyloxy)propanoic acid 
• 100-39-0 benzyl bromide 
• 77287-11-7 methyl (S)-2-(benzyloxy)propanoate 
• 100423-74-3 ethyl (2R)-2-(benzyloxy)propanoate 
• 100-44-7 benzyl chloride 
• 87604-49-7 (2R,3S)-3-O-benzyl-1,2-O-isopropylidenebutane-1,2,3-triol 
• 87604-55-5 (2R,3S)-3-O-benzylbutane-1,2,3-triol 
• 85726-34-7 6-O-Benzyl-7-desoxy-1,2:3,4-di-O-isopropyliden-L-glycero-α-D-galacto-heptopyranose 
• 85726-39-2 O-Benzyl-7-desoxy-L-glycero-D-galactoheptit 

Downstream Products

• 406940-46-3 (-)-(S)-2-(benzyloxy)-N-methoxy-N-methylpropanamide 
• 1239425-90-1 (S)-benzyl 2-((S)-2-(benzyloxy)propanamido)-3-methylbutanoate 
• 170985-85-0 N’-[(1S,2S)-2-(benzyloxy)-1-ethylpropyl]formic hydrazide 
• 184177-83-1 2-[(1S,2S)-1-ethyl-2-benzyloxypropyl]-2,4-dihydro-4-[4-[4-(4-hydroxyphenyl)piperazin-1-yl]phenyl]-3H-1,2,4-triazol-3-one 
• 170985-86-1 4-(4-(4-(4-(((3R,5R)-5-((1H-1,2,4-triazol-1-yl)methyl)-5-(2,4-difluorophenyl)tetrahydrofuran-3-yl)methoxy)phenyl)piperazin-1-yl)phenyl)-1-((2S,3S)-2-(benzyloxy)pentan-3-yl)-1H-1,2,4-triazol-5(4H)-one 
• 77287-11-7 methyl (S)-2-(benzyloxy)propanoate 
• 81445-44-5 (S)-2-(benzyloxy)propanal 
• 170985-84-9 (S)-N'-(2-(benzyloxy)propylidene)formylhydrazide 
• 34097-57-9 (±)-2-(benzyloxy)propanenitrile 
• 100836-85-9 (R)-2-benzyloxypropionic acid 

Relevant articles and documents

HPLC separation of 2-aryloxycarboxylic acid enantiomers on chiral stationary phases

The possibility for separating enantiomers of a number of practically significant 2-aryloxycarboxylic acids was studied by normal- and reversed-phase HPLC on popular chiral stationary phases. The best separation parameters were achieved on the chiral phases with the polysaccharide base Chiralcel OD-H and Chiralpack AD under the normal-phase HPLC conditions. The (S)- and (R)-enantiomers of 2-(1-naphthyloxy)- and 2-(2-iodophenoxy)propionic acids with enantiomeric excess ee >99% were isolated using preparative chiral HPLC.

Stereodivergence in the Ireland-Claisen Rearrangement of α-Alkoxy Esters

A systematic investigation into the Ireland-Claisen rearrangement of α-alkoxy esters is reported. In all cases, the use of KN(SiMe3)2 in toluene gave rearrangement products corresponding to a Z-enolate intermediate with excellent diastereoselectivity, presumably because of chelation control. On the other hand, chelation-controlled enolate formation could be overcome for most substrates through the use of lithium diisopropylamide (LDA) in tetrahydrofuran (THF).

Acyclic 1,4-Stereocontrol via the Allylic Diazene Rearrangement: Development, Applications, and the Essential Role of Kinetic e Stereoselectivity in Tosylhydrazone Formation

We report full details of a method for 1,3-reductive transposition of α-alkoxy-α,β-unsaturated hydrazones to provide E-alkenes with high 1,4-stereocontrol between the two respective allylic stereocenters. The process couples a chelation-controlled reduction of the hydrazone with an in situ allylic strain controlled retro-ene reaction of an allyl diazene, i.e., an allylic diazene rearrangement. Such stereotriads are frequently observed motifs in natural products. We observed a fortuitous kinetic preference for the E-hydrazone geometry during the hydrazonation reaction, as only the E-isomers could undergo chelation-controlled reduction.