33401-74-0

Basic information

• Product Name: (-)-ETHYL (S)-3-HYDROXY-3-PHENYLPROPIONATE
• Synonyms: ETHYL (S)-3-HYDROXY-3-PHENYLPROPANOATE;(-)-ETHYL (S)-3-HYDROXY-3-PHENYLPROPIONATE;(S)-(-)-ETHYL-3-HYDROXY 3-PHENYLPROPIONATE;(-)-Ethyl (S)-3-hydroxy-3-phenylpropionate,98%;Ethyl (3S)-3-hydroxy-3-phenylpropanoate;(S)-Ethyl3-Hydroxy-3-phenylpropanoate
• CAS NO: 33401-74-0
• Molecular Formula: C₁₁H₁₄O₃
• Molecular Weight: 194.23
• EINECS: 222-269-5
• Product Categories: Chiral Building Blocks;Esters;Organic Building Blocks
• Mol File: 33401-74-0.mol
• Article Data: 177

Chemical Properties

• Boiling Point: 315.3 °C at 760 mmHg
• Flash Point: 132.6 °C
• Appearance: Clear colorless liquid
• Density: 1.119 g/cm³
• Vapor Pressure: 0.000186mmHg at 25°C
• Refractive Index: n20/D 1.510
• Storage Temp.: 2-8°C
• PKA: 13.57±0.20(Predicted)
• CAS DataBase Reference: (-)-ETHYL (S)-3-HYDROXY-3-PHENYLPROPIONATE(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-ETHYL (S)-3-HYDROXY-3-PHENYLPROPIONATE(33401-74-0)
• EPA Substance Registry System: (-)-ETHYL (S)-3-HYDROXY-3-PHENYLPROPIONATE(33401-74-0)

Safety Data

• Hazard Codes: Xi:Irritant
• Statements: R36/37/38:Irritating to eyes, respiratory system and skin.
• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 33401-74-0(Hazardous Substances Data)

Usage

Chemical Properties

Clear colorless liquid

InChI:InChI=1/C11H14O3/c1-2-14-11(13)8-10(12)9-6-4-3-5-7-9/h3-7,10,12H,2,8H2,1H3/t10-/m0/s1

Upstream product

• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 1117-96-0 Diazoethan 
• 25409-25-0 ethyl 3-acetoxy-3-phenylpropionate 
• 100-52-7 benzaldehyde 
• 623-48-3 ethyl iodoacetae 
• 36567-72-3 (S)-3-hydroxy-3-phenylpropanoic acid 
• 75-03-6 ethyl iodide 
• 95614-81-6 (S)-3-Hydroxy-N-methoxy-3-phenyl-propionimidic acid ethyl ester 
• 95614-77-0 (2S,3S)-3-Hydroxy-N-methoxy-3-phenyl-2-((R)-toluene-4-sulfinyl)-propionimidic acid ethyl ester 
• 146452-39-3 (2S,3R) ethyl 2-chloro-3-hydroxy-3-phenylpropionate 
• 146452-40-6 (2R,3R) ethyl 2-chloro-3-hydroxy-3-phenylpropionate 
• 105-36-2 ethyl bromoacetate 
• 18295-66-4 1-ethoxy-1-(trimethylsiloxy)ethene 
• 42201-84-3 1-ethoxy-1-(tert-butyldimethylsilyloxy)ethene 

Downstream Products

• 36615-45-9 methyl (S)-3-hydroxy-3-phenylpropionate 
• 96854-34-1 (S)-3-phenyl-1,3-propanediol 
• 112635-77-5 ethyl (S)-(-)-3-(tert-butyldimethylsilyloxy)-3-phenylpropanoate 
• 138098-75-6 (R)-(+)-ethyl-3-phenylsulfanyl-3-phenylpropionate 
• 76183-10-3 (S)-3-hydroxy-N-methyl-3-phenylpropanamide 
• 190083-66-0 ethyl (S)-(-)-3-phenyl-3-(trimethylsilyloxy)propanoate 
• 127675-72-3 (-)-(S)-Ethyl 3-hydroxy-3-phenylpropanoate Mosher ester 
• 114133-37-8 (S)-N-methyl-3-amino-1-phenyl-1-propanol 
• 54910-89-3 (R)-fluoxetine 
• 100568-02-3 (S)-fluoxetine 
• 114247-09-5 (R)-fluoxetine hydrochloride 
• 114247-06-2 (S)-fluoxetine hydrochloride 
• 114133-36-7 (S)-(-)-3-iodo-1-phenyl-1-propanol 
• 115290-77-2 (1S) 3-phenyl-3-hydroxypropyl methanesulfonate 

Relevant articles and documents

Asymmetric reduction of 3-aryl-3-keto esters using Rhizopus species

Ethyl 3-aryl-3-oxopropanoates (aryl: phenyl, 2-fluorophenyl, 3-nitrophenyl, and 4-nitrophenyl) were reduced enantioselectively to the corresponding (S)-alcohols by the fungus Rhizopus arrhizus and other Rhizopus sp. The best results were generally obtaine

Asymmetric synthesis XXVI: Catalytic enantioselective syntheses of β-hydroxy esters via double chiral induction in asymmetric Reformatsky reactions

Catalytic asymmetric Reformatsky reactions of benzaldehyde with optically active menthyl bromoacetates in the presence of Zn-Cu couple were performed using 0.25 equiv. of (1R,2S) or (1S,2R)-N,N-dimethyl-2-amino-1,2-diphenyl ethanol as chiral ligand to obt

Enantioselective synthesis of a key intermediate aldehyde toward the polyene macrolide filipin III, based on a chiral oxazaborolidinone-promoted asymmetric aldol reaction

A versatile preparation of an enantiopure aldehyde useful for the asymmetric total synthesis of filipin III was developed using a chiral oxazaborolidinone-promoted asymmetric aldol reaction with a dithiolane silyl nucleophile. The sign and magnitude of th

Immobilized microorganisms in the reduction of ethyl benzoylacetate

The enantioselective reduction of ethyl benzoylacetate (EBA) into ethyl (S)-3-hydroxy-3-phenylpropanoate (S-HPPE) by nine yeast strains and three filamentous fungi strains is described. The conversion obtained was in the range 0-89% and the enantiomeric excess was 100% in many cases. Conversion levels were higher when the reduction was performed with microorganisms immobilized in calcium alginate and enantioselectivity remained excellent. Some reaction's conditions of bioreduction by immobilized cells of Rhodotorula rubra were studied using a 25-2 fractional factorial design.

Structure-guided evolution of a ketoreductase for efficient and stereoselective bioreduction of bulky α-amino β-keto esters

Ketoreductases have shown considerable potential as biocatalysts in the asymmetric synthesis of chiral alcohols. However, compared to the widely studied ketoreductases for chiral alcohols, limited knowledge is available about ketoreductases for efficient

Chiral amino-pyridine-phosphine tridentate ligand, manganese complex, and preparation method and application thereof

The invention discloses a chiral amino-pyridine-phosphine tridentate ligand, a manganese complex, and a preparation method and application thereof. The chiral amino-pyridine-phosphine tridentate ligand is shown as a formula II, and the manganese complex of the chiral amino-pyridine-phosphine tridentate ligand can be used for efficiently catalyzing and hydrogenating ketone compounds to prepare chiral alcohol compounds in a high enantioselectivity mode. The chiral amino-pyridine-phosphine tridentate ligand and the manganese complex are simple in synthesis process, good in stability, high in catalytic activity and mild in reaction conditions.