(4S,5R)-(-)-cis-4,5-Diphenyl-2-oxazolidinone

HCID 9859564

Notes Reactions

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Basic information

CAS: 23204-70-8
Standard SMILES: O=C1N[C@@H](c2ccccc2)[C@@H](c2ccccc2)O1
InChIKey: LTENIVFVXMCOQI-UONOGXRCSA-N
Molecular formula: C15H13NO2
Average molar mass: 239.27 g/mol
Monoisotopic mass: 239.09462866

Names & identifiers

Preferred name: (4S,5R)-(-)-cis-4,5-Diphenyl-2-oxazolidinone
IUPAC: (4S,5R)-4,5-diphenyl-1,3-oxazolidin-2-one
English name: (4S,5R)-(-)-cis-4,5-Diphenyl-2-oxazolidinone
Molecular formula: C15H13NO2
Molecular weight: 239.27

Names & synonyms

(4S,5R)-(-)-cis-4,5-Diphenyl-2-oxazolidinoneRefChem:403480623-654-423204-70-8(4S,5R)-4,5-Diphenyl-1,3-oxazolidin-2-one(4S,5R)-4,5-diphenyloxazolidin-2-one(4S,5R)-4,5-diphenyl-2-oxazolidinoneMFCD00799526(4S,5R)-cis-4,5-Diphenyloxazolidin-2-onecis-4,5-Diphenyl-2-Oxazolidinone(4S,5R)-(-)-cis-Diphenyl-2-oxazolidinone(4S-cis)-4,5-Diphenyl-2-oxazolidinone; (-)-cis-4,5-Diphenyl-2-oxazolidinone; (4S,5R)-4,5-Diphenyloxazolidin-2-one;

Show more names

(4S,5R)-45-diphenyloxazolidin-2-one(-)-cis-4,5-Diphenyl-2-oxazolidinone(4S-cis)-4,5-Diphenyl-2-oxazolidinone(4S,5R)-(-)-CIS-4,5-DIPHENYL-2-OXAZOLIDI2-Oxazolidinone, 4,5-diphenyl-, (4S,5R)-(4S,5R)-4,5-Diphenyl-2-oxazolidinone,99%e.e.

19202-66-5rel-(4R*,5S*)-4,5-Diphenyloxazolidine-2-oneSCHEMBL1443275DTXSID70431963LTENIVFVXMCOQI-UONOGXRCSA-N4,5-cis-Diphenyl-2-oxooxazolidineAKOS016842848AS-43482

Database identifiers

CAS: 23204-70-8
PubChem CID: 9859564
DTXSID: DTXSID70431963
EC Number: 623-654-4
Nikkaji: J411.758A

Properties

Computed structural properties

XLogP: 2.8
Topological polar surface area: 38.3 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 2
Rotatable bonds: 2
Heavy atoms: 18
Formal charge: 0
Complexity: 293

Physicochemical properties

Melting point: 227 · 227-232 °C(lit.)
Boiling point: 466.6 · 466.6±45.0 °C(Predicted)
Density: 1.192 · 1.192±0.06 g/cm3(Predicted)
storage temp.: Refrigerator
solubility: Chloroform (Slightly)
pka: 11.56 · 11.56±0.60(Predicted)
form: Solid
color: White to Off-White
optical activity: 23 · [α]23/D 57±4°, c = 2 in chloroform (or methanol)
InChI: 1S/C15H13NO2/c17-15-16-13(11-7-3-1-4-8-11)14(18-15)12-9-5-2-6-10-12/h1-10,13-14H,(H,16,17)/t13-,14+/m0/s1
InChIKey: LTENIVFVXMCOQI-UONOGXRCSA-N
SMILES: O=C1N[C@H]([C@H](O1)c2ccccc2)c3ccccc3
UNSPSC Code: 12352005 · 12352005
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H319-H335
Precautionary statements: 261 · P261-P305+P351+P338
target organs: Respiratory system
PPE: 95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes: Xi
Risk Statements: 36 · 36/37/38
Safety Statements: 26 · 26-36
WGK Germany: 3 · 3
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 2 Skin · Eye Irrit. 2Skin Irrit. 2STOT SE 3

Safety & regulation

GHS classification

GHS Classification · 5 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]；H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Hazard Classes and CategoriesSkin Irrit. 2 (100%)；Eye Irrit. 2 (100%)；STOT SE 3 (100%)

Safety data

PPE: dust mask type N95 (US), Eyeshields, Gloves
wgk: 3
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
safety_code: 26-36
Storage Class: 11 - Combustible Solids
target organs: Respiratory system
Hazard statements: H315-H319-H335
Hazard Classifications: Eye Irrit. 2Skin Irrit. 2STOT SE 3
Precautionary statements: P261-P305+P351+P338

Chemistry & industry

Applications

Uses(4S,5R)-(-)-cis-Diphenyl-2-oxazolidinone is used as a catalyst in the enantioselective synthesis of chiral phthalides.

UsesVersatile chiral auxiliary used in a variety of highly diastereoselective reactions such as Michael additions, Diels-Alder reactions, cyclopropanations, and allylations.