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Name	(S)-4-Benzyl-2-oxazolidinone	EINECS	618-632-6
CAS No.	90719-32-7	Density	1.176 g/cm³
PSA	38.33000	LogP	1.66630
Solubility	Insoluble in water.	Melting Point	86-88 °C(lit.)
Formula	C₁₀H₁₁NO₂	Boiling Point	398.8 °C at 760 mmHg
Molecular Weight	177.203	Flash Point	195 °C
Transport Information	N/A	Appearance	white to light yellow crystal powder
Safety	24/25-36-26	Risk Codes	36/37/38
Molecular Structure		Hazard Symbols	Xi
Synonyms	(4S)-4-benzyloxazolidin-2-one;S-4-benzyl-2-oxazolidinone;(S)-4-Benzyl-4-oxazolidinone;(S)-4-benzyl-2-oxazolidone;(S)-(-)-4-Benzyl-2-oxazolidincne;(S)-4-Benzyl-2-0xazolidinone;(S)-4-Benzyloxazolidin-2-one;(S)-(-)-4-benzyl-2-oxazolidinone;(S)-4-Benzyl-oxazolidin-2-one;S-(+)-4-Benzyl-2-oxazolidinone;S-4-Bhenyl-2-Oxazolidinone;(4S)-4-Benzyl-1,3-oxazolidin-2-one;(S)-4-(Benzyl)-2-Oxazolidinone;(S)-(+)-4-Benzyl-2-Oxazolidinone;(S)-4-benzyl-2-oxazolidenone;	Article Data	183

(S)-4-Benzyl-2-oxazolidinone Synthetic route

: 3182-95-4
L-Phenylalaninol

: 105-58-8
Diethyl carbonate

: 90719-32-7
(S)-4-Benzyl-2-oxazolidinone

Conditions

Conditions	Yield
With potassium carbonate In ethyl acetate at 120 - 130℃; for 3h;	100%
With potassium carbonate In ethanol at 130 - 135℃; for 1h;	88%
With potassium carbonate at 135 - 140℃; for 2h;	84%

: 717137-43-4
(4S,3'R)-3-[3'-(N,N-dibenzylamino)-3'-phenylpropanoyl]-4-benzyloxazolidin-2-one

A: 614-19-7, 3646-50-2, 13921-90-9, 40856-44-8
(R)-3-phenyl-3-aminopropionic acid

B: 90719-32-7
(S)-4-Benzyl-2-oxazolidinone

Conditions

Conditions	Yield
Stage #1: (4S,3'R)-3-[3'-(N,N-dibenzylamino)-3'-phenylpropanoyl]-4-benzyloxazolidin-2-one With dihydrogen peroxide; lithium hydroxide In tetrahydrofuran; water at 0 - 20℃; for 16h; Stage #2: With hydrogenchloride In water pH=1 - 2; Stage #3: With Pearlman's catalist; hydrogen In methanol at 20℃; for 24h;	A 43% B 100%

: 213385-64-9
(S)-3-((2S,4S)-2-Azido-4-methyl-hexanoyl)-4-benzyl-oxazolidin-2-one

A: 90719-32-7
(S)-4-Benzyl-2-oxazolidinone

B: 221292-86-0
(2S,4S)-2-Azido-4-methyl-hexanoic acid

Conditions

Conditions	Yield
Stage #1: (S)-3-((2S,4S)-2-Azido-4-methyl-hexanoyl)-4-benzyl-oxazolidin-2-one With lithium hydroxide In tetrahydrofuran; water at 0℃; for 1h; Stage #2: With hydrogenchloride In water pH=1 - 2;	A 99% B 96.7%

: 67-56-1
methanol

: 181431-20-9
(4S)- 4-benzyl-3-((2R)-2-methyl-3-phenylpropanoyl)-2-oxazolidinone

A: 29393-16-6
methyl (2R)-2-methyl-3-phenylpropanoate

B: 90719-32-7
(S)-4-Benzyl-2-oxazolidinone

Conditions

Conditions	Yield
With samarium diiodide In tetrahydrofuran at 20℃; for 72h;	A 98% B 99%

: 64-17-5
ethanol

: 198649-20-6
(4S)-3-(dodecanoyl)-4-benzyl-2-oxazolidinone

A: 106-33-2
ethyl laurate

B: 90719-32-7
(S)-4-Benzyl-2-oxazolidinone

Conditions

Conditions	Yield
With samarium diiodide In tetrahydrofuran at 20℃; for 168h;	A 99% B 99%

: 198649-20-6
(4S)-3-(dodecanoyl)-4-benzyl-2-oxazolidinone

: 100-51-6
benzyl alcohol

A: 140-25-0
benzyl dodecanoate

B: 90719-32-7
(S)-4-Benzyl-2-oxazolidinone

Conditions

Conditions	Yield
With samarium diiodide In tetrahydrofuran at 20℃; for 168h;	A 83% B 99%

: 131685-53-5, 101711-78-8
(S)-4-benzyl-3-propionyl-2-oxazolidinone

: 90719-32-7
(S)-4-Benzyl-2-oxazolidinone

Conditions

Conditions	Yield
With methanol; C17H23BN2O at 25℃; under 760.051 Torr; for 1h; Inert atmosphere; chemoselective reaction;	98%
Multi-step reaction with 2 steps 1: 1.) di-n-butylboron triflate, N,N-diisopropylethylamine, 3.) aq. H2O2 / 1) CH2Cl2, 0 deg C, 30 min; 2) CH2Cl2, -78 deg C, 45 min, 0 deg C, 2 h; 3) methanol, 0 deg C, 1 h 2: 1.) trimethylaluminum / 1) CH2Cl2, toluene, rt, 1 h; 2) CH2Cl2, toluene, -20 deg C --> rt, rt, 1.5 h View Scheme
Multi-step reaction with 2 steps 1: 1.) dibutylboron trifluoromethanesulfonate, diisopropylethylamine / 1.) CH2Cl2, 0 deg C, 1 h, 2.) CH2Cl2, -78 deg C (1 h), room temp. (5 h) 2: 80 percent / LiBH4, H2O / tetrahydrofuran / 3 h / Ambient temperature View Scheme

: (S)-4-benzyl-3-((1'R,2'S,3'R,7a'R)-1'-phenyl-1',2',5',6',7',7a'-hexahydrospiro[indeno[1,2-b]quinoxaline-11,3'-pyrrolizine]-2'-ylcarbonyl)oxazolidin-2-one

: 616-38-6
carbonic acid dimethyl ester

A: methyl (1'R,2'S,7a'R,11R)-1'-phenyl-1',2',5',6',7',7a'-hexahydrospiro[indeno[1,2-b]quinoxaline-11,3'-pyrrolizine]-2'-carboxylate

B: 90719-32-7
(S)-4-Benzyl-2-oxazolidinone

Conditions

Conditions	Yield
With sodium methylate In dichloromethane at 20℃; for 4h;	A 98% B 96%

: 373363-70-3
N-(4-benzyl-2-oxo-oxazolidin-3-yl)-N-(5-chloro-1-propyl-pentyl)-benzamide

A: 373363-71-4
N-(5-chloro-1-propyl-pentyl)-benzamide

B: 90719-32-7
(S)-4-Benzyl-2-oxazolidinone

Conditions

Conditions	Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide; samarium diiodide In tetrahydrofuran for 0.166667h;	A 97% B n/a

: 1352791-77-5
tert-butyl (3R)-4-[(S)-4-benzyl-2-oxooxazolidin-3-yl]-3-[3-(benzyloxy)benzyl]-4-oxobutanoate

A: 1352791-75-3
(3R)-2-[3-(benzyloxy)benzyl]-4-tert-butoxy-4-oxobutanoic acid

B: 90719-32-7
(S)-4-Benzyl-2-oxazolidinone

Conditions

Conditions	Yield
With dihydrogen peroxide; lithium hydroxide In tetrahydrofuran; water for 3h;	A 97% B 89%

(S)-4-Benzyl-2-oxazolidinone Chemical Properties

IUPAC Name: (4S)-4-benzyl-1,3-oxazolidin-2-one
Synonyms of (S)-4-Benzyl-2-oxazolidinone (CAS NO.90719-32-7): (S)-(-)-4-Benzyl-2-oxazolidinone
CAS NO: 90719-32-7
Molecular formula: C₁₀H₁₁NO₂
Molecular Weight: 177.2
Molecular Structure:
H bond acceptors: 3
H bond donors: 1
Freely Rotating Bonds: 2
Polar Surface Area: 29.54 Å²
Index of Refraction: 1.551
Molar Refractivity: 48.08 cm³
Molar Volume: 150.5 cm³
Surface Tension: 43.2 dyne/cm
Density: 1.176 g/cm³
Flash Point: 195 °C
Enthalpy of Vaporization: 64.95 kJ/mol
Boiling Point: 398.8 °C at 760 mmHg
Vapour Pressure: 1.43E-06 mmHg at 25°C
Melting point: 86-88 °C(lit.)
Alpha: -62 ^o (C=1, CHCl₃)
Storage temp: 0-6°C
Sensitive: Hygroscopic
Appearance: white to light yellow crystal powder
Product Categories of (S)-4-Benzyl-2-oxazolidinone (CAS NO.90719-32-7): Oxazolidinone;Chiral Compounds;chiral;Aromatics Compounds;Asymmetric Synthesis;Chiral Building Blocks;Glycidyl Compounds, etc. (Chiral);Synthetic Organic Chemistry;Chiral chemicals;Peptide;Aromatics;Chiral Reagents;Heterocycles;Asymmetric Synthesis;Chiral Auxiliaries;Oxazolidinone Derivatives

(S)-4-Benzyl-2-oxazolidinone Uses

(S)-4-Benzyl-2-oxazolidinone (CAS NO.90719-32-7) is a kind of pharmaceutical intermediate.

(S)-4-Benzyl-2-oxazolidinone Safety Profile

Safety Information about (S)-4-Benzyl-2-oxazolidinone (CAS NO.90719-32-7):
Hazard Codes: Irritant Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 24/25-36-26
S24/25: Avoid contact with skin and eyes.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36: Wear suitable protective clothing.
WGK Germany: 3
F: 3-10
HS Code: 29349990

(S)-4-Benzyl-2-oxazolidinone Specification

General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media: Use water spray, dry chemical, carbon dioxide, or chemical foam.
Handling: Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes. Avoid ingestion and inhalation.
Storage: Store in a cool, dry place. Store in a tightly closed container.

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