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A18236 (S)-(-)-4-Benzyl-2-oxazolidinone, 99%

CAS Number
90719-32-7
Synonyms

Stock No. Size Price ($) Quantity Availability
A18236-03 1g 30.00
A18236-06 5g 93.20
A18236-14 25g 292.00
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(S)-(-)-4-Benzyl-2-oxazolidinone, 99%

MDL
MFCD00064496

Chemical Properties

Formula
C10H11NO2
Formula Weight
177.20
Melting point
87-89°
Storage & Sensitivity
Hygroscopic. Ambient temperatures.
Solubility
Insoluble in water.

Applications

(S)-(-)-4-Benzyl-2-oxazolidinone is used in chiral auxiliary asymmetric alkylation. It has been used in the synthesis of (S)-equol. Preparation and functionalization of chiral, stabilized ylides. It was used for asymmetric synthesis of (3R)- and (3S)-piperazic acid.

Notes

Hygroscopic. Incompatible with oxidizing agents.

Literature References

David J.Madar; Hana Kopecka; Daisy Pireh; Jonathan Pease; Marina Pliushchev; Richard J.Sciotti; Paul E.Wiedeman; Stevan W.Djuric. Synthesis of N-arylated oxazolidinones via a palladium catalyzed cross coupling reaction. Application to the synthesis of the antibacterial agent Dup-721. Tetrahedron Letters. 2001, 42,(22), 3681-3684.

 

Ralf-Siegbert Hauck; Heinz Nau. The enantiomers of the valproic acid analogue 2-n-propyl-4-pentynoic acid (4-yn-VPA): Asymmetric synthesis and highly stereoselective teratogenicity in mice. Pharmaceutical Research. 1992, 9,(7), 850-855.

Evans chiral auxiliary; compare (4S)-(-)-Isopropyl-2-oxazolidinone, A14029.

For details of use in enantioselective aldol condensation, see: Org. Synth. Coll., 8, 339 (1993):

A simplified method of acylation of the oxazolidinone, avoiding the need for rigorously anhydrous conditions, has been reported using acyl chlorides, anhydrides or pivaloyl mixed anhydrides as the acylating agents catalyzed by DMAP: Synthesis, 1283 (1996).

See also (4S)-(-)-Isopropyl-2-oxazolidinone, A14029.

GHS Hazard and Precautionary Statements

Hazard Statements: H302-H315-H320-H335-H373

Harmful if swallowed. Causes skin irritation. Causes eye irritation. May cause respiratory irritation. May cause damage to organs through prolonged or repeated exposure.

Precautionary Statements: P261-P262-P264b-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P314-P330-P332+P313-P337+P313-P362-P501c

Avoid breathing dust/fume/gas/mist/vapours/spray. Do not get in eyes, on skin, or on clothing. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Get medical advice/attention if you feel unwell. Rinse mouth. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Take off contaminated clothing and wash before reuse. Dispose of contents/ container to an approved waste disposal plant

Other References

Beilstein
3649667
Harmonized Tariff Code
2934.99
TSCA
No

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