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(4R,5S)-(+)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE

(4R,5S)-(+)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE Structure
CAS No.
77943-39-6
Chemical Name:
(4R,5S)-(+)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE
Synonyms
(4R,5S)-4-Methyl-5-phenyloxazolidin-2-one;(4S,5S)-4-Methyl-5-phenyloxazolidin-2-one;TB-2039;4-methyl-5-phenyl-2-oxazolidinone;5β-Phenyl-4β-methyloxazolidine-2-one;4α-Methyl-5α-phenyloxazolidine-2-one;4-Methyl-5-phenyl-1,3-oxazolidin-2-one;(4R-5S)-4-Methyl-5-Phenyl-2-Oxazocidin;(4R,5S)-4-Methyl-5-phenyl-2-oxazolidone;(4R,5S)-4-Methyl-4-phenyl-2-oxazolidone
CBNumber:
CB5321737
Molecular Formula:
C10H11NO2
Molecular Weight:
177.2
MOL File:
77943-39-6.mol
MSDS File:
SDS
Modify Date:
2023/5/25 10:25:51

(4R,5S)-(+)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE Properties

Melting point 121-123 °C(lit.)
Boiling point 309.12°C (rough estimate)
Density 1.1607 (rough estimate)
refractive index 1.5168 (estimate)
storage temp. Sealed in dry,Room Temperature
solubility Chloroform (Slightly), Ethyl Acetate (Slightly)
form Liquid
pka 12.35±0.60(Predicted)
color Clear colorless to yellow-brown, may darken in storage
optical activity [α]18/D +168°, c = 2 in chloroform
BRN 1211705
InChI InChI=1S/C10H11NO2/c1-7-9(13-10(12)11-7)8-5-3-2-4-6-8/h2-7,9H,1H3,(H,11,12)/t7-,9-/m1/s1
InChIKey PPIBJOQGAJBQDF-VXNVDRBHSA-N
SMILES O1[C@@H](C2=CC=CC=C2)[C@@H](C)NC1=O
CAS DataBase Reference 77943-39-6(CAS DataBase Reference)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H302-H315-H319-H335
Precautionary statements  P261-P305+P351+P338
Hazard Codes  N
Safety Statements  22-24/25
WGK Germany  3
HS Code  29349990

(4R,5S)-(+)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE price More Price(1)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) 298891 (4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinone 99% 77943-39-6 5G ₹16920 2022-06-14 Buy
Product number Packaging Price Buy
298891 5G ₹16920 Buy

(4R,5S)-(+)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE Chemical Properties,Uses,Production

Chemical Properties

white to light yellow crystal powde

Uses

(4R,5S)-4-Methyl-5-phenyloxazolidinone is used as effective chiral auxiliary for conjugate addition asymmetric synthesis of (-)-aplysillamide B.

Preparation

To a solution of (1S,2R)-norephedrine (40 g, 0.26 mol) in toluene (400 mL) was added diethyl carbonate (37 mL, 0.32 mol). The mixture was heated to reflux (under Ar) while 40 mL of solvent was removed through the use of a Dean–Stark apparatus. The mixture was allowed to cool for 20 min, and then sodium methoxide (1 g) was added. Upon reheating, an EtOH/toluene azeotropic mixture was removed at 75–77 °C. After 3 h, the reaction was complete and the temperature of the mixture had increased to 125 °C. The mixture was left to stand at room temperature for 16 h, whereupon (4R,5S)-4-methyl-5-phenyloxazolidin-2-one (40.6 g) crystallized and could be collected. The solvent was removed from the filtrate in vacuo and the residue was redissolved in EtOAc (250 mL). This solution was washed with brine (50 mL) and a precipitate was removed by filtration. The solvent was then removed in vacuo and toluene (50 mL) was added to the residue. Removal of the toluene by distillation yielded oily crystals of the oxazolidinone, which were washed with Et2O to afford 4.5 g (total 45 g, 97%).

(4R,5S)-(+)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE Preparation Products And Raw materials

Raw materials

Preparation Products

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(4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinone 99% 4-Methyl-5-phenyl-1,3-oxazolidin-2-one (4R,5S)-(-)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE (4R,5S)-(+)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE (4R,5S)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE (4R,5S)-4-Methyl-5-phenyl-2-oxazolidone (4R,5S)-(+)-4-METHYL-5-PHENYL-2-OXAZOLID -INONE, 99% (99% EE/GLC) (4R,5S)-4-METHYL-5-PHENYL-2-OXAZOLIDI DI NONE 2-Oxazolidinone, 4-methyl-5-phenyl-, (4R,5S)- 4-methyl-5-phenyl-2-oxazolidinone (4S)-4β-Methyl-5α-phenyloxazolidine-2-one 5β-Phenyl-4β-methyloxazolidine-2-one (4R)-4α-Methyl-5α-phenyloxazolidin-2-one 4α-Methyl-5α-phenyloxazolidine-2-one (4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinone,99% (4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidine (4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinone ,98% (4R,5S)-(+)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE USP/EP/BP (4R,5S)-4-Methyl-5-phenyl-1,3-oxazolidin-2-one (4S,5S)-4-Methyl-5-phenyloxazolidin-2-one (4R,5S)-4-Methyl-5-phenyloxazolidin-2-one TB-2039 (4R-5S)-4-Methyl-5-Phenyl-2-Oxazocidin (4R,5S)-4-Methyl-4-phenyl-2-oxazolidone 77943-39-6 Chiral Auxiliaries Asymmetric Synthesis Oxazolidinone Derivatives chiral Peptide