benzyl 2,5-dihydro-1H-pyrrole-1-carboxylate

• ChemBase ID: 147647
• Molecular Formular: C12H13NO2
• Molecular Mass: 203.23712
• Monoisotopic Mass: 203.09462866
• SMILES: c1ccc(cc1)COC(=O)N1CC=CC1
• Canonical SMILES: O=C(N1CC=CC1)OCc1ccccc1
• InChI: InChI=1S/C12H13NO2/c14-12(13-8-4-5-9-13)15-10-11-6-2-1-3-7-11/h1-7H,8-10H2
• InChIKey: XSKKIFJNZPNVGO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl 2,5-dihydro-1H-pyrrole-1-carboxylate
• IUPAC Traditional name: benzyl 2,5-dihydropyrrole-1-carboxylate
• Synonyms: Benzyl 3-pyrroline-1-carboxylate; Benzyl 2,5-dihydro-1H-pyrrole-1-carboxylate; 3-吡咯烷-1-甲酸苄酯

Database IDs

• CAS Number: 31970-04-4
• MDL Number: MFCD01863559
• PubChem SID: 162241834; 24872878
• PubChem CID: 643471

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 2.1165187
• LogD (pH = 7.4): 2.1165187
• Log P: 2.1165187
• Molar Refractivity: 58.8451 cm^3
• Polarizability: 22.300976 Å^3
• Polar Surface Area: 29.54 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 133-137 °C/0.6 mmHg(lit.)
• Density: 1.132 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.544(lit.)

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: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter

Product Information

• Purity: 90%; 95+%
• Empirical Formula (Hill Notation): C12H13NO2

DETAILS

Sigma Aldrich - 494127

Application
Used in the preparation of bicyclo[3.3.0]octenes or -octanes via carbon ion mediated rearrangements of cyclooctadiene1 or cycloocteneepoxide.2
Used to prepare a pyridone sulfonate analog of Combrestatin A-4 showing good antimitotic activity.
Packaging
5 g in glass bottle