Cas no 875444-08-9 ((4S,5R)-5-[3,5-Bis(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one)

(4S,5R)-5-[3,5-Bis(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one is a chiral oxazolidinone derivative widely utilized as an auxiliary in asymmetric synthesis. Its rigid structure and electron-withdrawing trifluoromethyl groups enhance reactivity and stereocontrol in key transformations such as aldol, alkylation, and Diels-Alder reactions. The (4S,5R) configuration ensures high diastereoselectivity, making it valuable for constructing complex stereocenters in pharmaceutical and fine chemical synthesis. The compound’s stability under a range of reaction conditions and ease of removal post-synthesis further contribute to its utility. Its well-defined stereochemistry and consistent performance make it a preferred choice for enantioselective methodologies in academic and industrial research.
(4S,5R)-5-[3,5-Bis(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one structure
875444-08-9 structure
Product Name:(4S,5R)-5-[3,5-Bis(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one
CAS No:875444-08-9
MF:C12H9F6NO2
MW:313.195784330368
MDL:MFCD16294904
CID:655237
Update Time:2025-06-30

(4S,5R)-5-[3,5-Bis(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one Chemical and Physical Properties

Names and Identifiers

    • (4S,5R)-5-(3,5-Bis(trifluoromethyl)phenyl)-4-methyloxazolidin-2-one
    • (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one
    • 2-Oxazolidinone, 5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-, (4S,5R)-
    • Anacetrapib intermediate-4
    • (4S,5R)-5-(3,5-bis(trifluoromethyl)phenyl)-4-methylox
    • (4S,5R)-5-[3,5-bis(triflu...
    • (4S,5R)-5-(3,5-Bis-trifluoromethyl-phenyl)-4-methyl-oxazolidin-2-one
    • C12H9F6NO2
    • (4S,5R)-5-[3,5-Bis(trifluoromethyl)phenyl]-4-methyloxazolidin-2-one
    • AK145429
    • OHIDCVTXTYVGRO-CDUCUWFYSA-N
    • BCP9000112
    • DS-8
    • (4S,5R)-5-[3,5-Bis(trifluoromethyl)phenyl]-4-methyl-2-oxazolidinone (ACI)
    • (4S,5R)-5-[3,5-Bis(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one
    • MDL： MFCD16294904
    • Inchi： 1S/C12H9F6NO2/c1-5-9(21-10(20)19-5)6-2-7(11(13,14)15)4-8(3-6)12(16,17)18/h2-5,9H,1H3,(H,19,20)/t5-,9-/m0/s1
    • InChI Key： OHIDCVTXTYVGRO-CDUCUWFYSA-N
    • SMILES： C[C@@H]1NC(=O)O[C@@H]1C1C=C(C(F)(F)F)C=C(C(F)(F)F)C=1

Computed Properties

  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 8
  • Heavy Atom Count: 21
  • Rotatable Bond Count: 1
  • Complexity: 386
  • Topological Polar Surface Area: 38.3

Experimental Properties

  • Density: 1.401

(4S,5R)-5-[3,5-Bis(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one Security Information

  • Signal Word：Warning
  • Hazard Statement： H317
  • Warning Statement： P261-P280
  • Storage Condition：Sealed in dry,2-8°C(BD162716)

(4S,5R)-5-[3,5-Bis(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one Pricemore >>

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SHANG HAI BI DE YI YAO KE JI GU FEN Co., Ltd.
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(4S,5R)-5-[3,5-Bis(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: Aluminum isopropoxide Solvents: Isopropanol ,  Toluene ;  overnight, 50 °C
1.2 Reagents: Potassium hydroxide ;  25 °C; 2 h, 25 °C
Reference
Synthesis and crystal structure of (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one
Cui, Hong; et al, Asian Journal of Chemistry, 2013, 25(14), 8043-8046

Production Method 2

Reaction Conditions
1.1 Reagents: Aluminum isopropoxide Solvents: Isopropanol ,  Toluene ;  12 h, 50 °C; 50 °C → rt
1.2 Reagents: Potassium hydroxide Solvents: Water ;  3 h, 20 °C
1.3 Reagents: Sodium chloride Solvents: Water
Reference
Can We Make Small Molecules Lean? Optimization of a Highly Lipophilic TarO Inhibitor
Mandal, Mihirbaran ; et al, Journal of Medicinal Chemistry, 2017, 60(9), 3851-3865

Production Method 3

Reaction Conditions
1.1 Reagents: 1,10-Phenanthroline ,  Potassium tert-butoxide ,  Cuprous chloride Solvents: Dimethylformamide ;  1 h, rt
1.2 1 h, rt
1.3 Solvents: Dimethylformamide ;  rt; 18 h, 50 °C
Reference
Self-Assembling Neodymium/Sodium Heterobimetallic Asymmetric Catalyst Confined in a Carbon Nanotube Network
Ogawa, Takanori; et al, Angewandte Chemie, 2013, 52(24), 6196-6201

(4S,5R)-5-[3,5-Bis(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one Raw materials

(4S,5R)-5-[3,5-Bis(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one Preparation Products

(4S,5R)-5-[3,5-Bis(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one Suppliers

Amadis Chemical Company Limited
Gold Member
Audited Supplier Audited Supplier
(CAS:875444-08-9)(4S,5R)-5-[3,5-Bis(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one
Order Number:A850068
Stock Status:in Stock
Quantity:100g
Purity:99%
Pricing Information Last Updated:Friday, 30 August 2024 07:28
Price ($):507.0

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875444-08-9 ((4S,5R)-5-[3,5-Bis(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one) Related Products

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Amadis Chemical Company Limited
(CAS:875444-08-9)(4S,5R)-5-[3,5-Bis(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one
A850068
Purity:99%
Quantity:100g
Price ($):507.0
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