(5R)-5-benzyl-2,2,3-trimethylimidazolidin-4-one hydrochloride

• ChemBase ID: 140985
• Molecular Formular: C13H19ClN2O
• Molecular Mass: 254.75576
• Monoisotopic Mass: 254.11859092
• SMILES: CC1(N(C(=O)[C@H](N1)Cc1ccccc1)C)C.Cl
• Canonical SMILES: O=C1[C@@H](Cc2ccccc2)NC(N1C)(C)C.Cl
• InChI: InChI=1S/C13H18N2O.ClH/c1-13(2)14-11(12(16)15(13)3)9-10-7-5-4-6-8-10;/h4-8,11,14H,9H2,1-3H3;1H/t11-;/m1./s1
• InChIKey: YIYFEXGDFJLJGM-RFVHGSKJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5R)-5-benzyl-2,2,3-trimethylimidazolidin-4-one hydrochloride
• IUPAC Traditional name: (5R)-5-benzyl-2,2,3-trimethylimidazolidin-4-one hydrochloride
• Synonyms: (5R)-2,2,3-Trimethyl-5-phenylmethyl-4-imidazolidinone monohydrochloride; (5R)-(+)-2,2,3-Trimethyl-5-benzyl-4-imidazolidinone monohydrochloride; (5r)-(+)-2,2,3-trimethyl-5-benzyl-4-imidazolidinone monohydrochloride; (5R)-2,2,3-三甲基-5-苯甲基-4-咪唑啉酮 单盐酸盐; (5R)-(+)-2,2,3-三甲基-5-苄基-4-咪唑啉酮 单盐酸盐

Database IDs

• CAS Number: 323196-43-6
• MDL Number: MFCD08276839
• PubChem SID: 162235221; 24884181
• PubChem CID: 16217983

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 1.3394761
• LogD (pH = 7.4): 1.5630312
• Log P: 1.5667765
• Molar Refractivity: 64.2111 cm^3
• Polarizability: 25.229525 Å^3
• Polar Surface Area: 32.34 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 157-161 °C
• Optical Rotation: [α]20/D +67°, c = 1 in H2O

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 97%; 98%
• Empirical Formula (Hill Notation): C13H19ClN2O

DETAILS

Sigma Aldrich - 663069

Application
Used in first highly enantioselective organocatalytic Diels-Alder reaction1 and 1,3-dipolar addition.2
Packaging
2 g in glass bottle
500 mg in glass bottle
Legal Information
U.S. Pat. 6,369,243 and related patents apply. For research purposes only.
Protocols & Applications
Metal-free Asymmetric Catalysis using Macmillan Imidazolidinone Organocatalysts