(3S)-3-aminooxolan-2-one hydrobromide

• ChemBase ID: 151304
• Molecular Formular: C4H8BrNO2
• Molecular Mass: 182.01582
• Monoisotopic Mass: 180.9738405
• SMILES: C1COC(=O)[C@H]1N.Br
• Canonical SMILES: O=C1OCC[C@@H]1N.Br
• InChI: InChI=1S/C4H7NO2.BrH/c5-3-1-2-7-4(3)6;/h3H,1-2,5H2;1H/t3-;/m0./s1
• InChIKey: MKLNTBLOABOJFZ-DFWYDOINSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-3-aminooxolan-2-one hydrobromide
• IUPAC Traditional name: L-homoserine lactone hydrobromide
• Synonyms: L-Homoserine lactone hydrobromide; (S)-(-)-α-Amino-γ-butyrolactone hydrobromide; L-(-)-alpha-Amino-gamma-butyrolactone hydrobromide; L-高丝氨酸内酯 氢溴酸盐; (S)-(-)-α-氨基-γ-丁内酯 氢溴酸盐; L-(-)-α-氨基-γ-丁乙酮氢溴酸盐

Database IDs

• CAS Number: 15295-77-9
• MDL Number: MFCD00674493; MFCD00012723
• Beilstein Number: 3912375
• PubChem SID: 162245460; 24870732
• PubChem CID: 16213138

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -2.7108617
• LogD (pH = 7.4): -1.1681297
• Log P: -0.9011904
• Molar Refractivity: 23.4142 cm^3
• Polarizability: 9.7096 Å^3
• Polar Surface Area: 52.32 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 225 °C (dec.)(lit.); 258-260°C
• Optical Rotation: [α]20/D -21±2°, c = 1% in H2O; [α]20/D -21°, c = 1 in H2O; -21 (c=1 in water)

Safety Information

• Storage Warning: Hygroscopic
• German water hazard class: 3
• Safety Statements: 22-24/25
• TSCA Listed: 否
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (AT); 98%; 99%
• Grade: purum
• Salt Data: HBr
• Empirical Formula (Hill Notation): C4H7NO2 · HBr
• Classification: Genuine Natural Compounds

DETAILS

Sigma Aldrich - 471429

Packaging
1, 5 g in glass bottle
Application
Used to prepare pseudopeptide inhibitors for Ras farnesyl-protein transferase1 as well as selenomethionine.2

Sigma Aldrich - 07252

Other Notes
Chiral building block: synthesis of biologically active peptides1; Preparation of seleno- and telluro-analogues of methionine2,3; Addition of Grignard reagents to a tert-alcohol 4