methyl (2S)-2-isocyanato-3-phenylpropanoate

• ChemBase ID: 145581
• Molecular Formular: C11H11NO3
• Molecular Mass: 205.20994
• Monoisotopic Mass: 205.07389322
• SMILES: COC(=O)[C@H](Cc1ccccc1)N=C=O
• Canonical SMILES: COC(=O)[C@H](Cc1ccccc1)N=C=O
• InChI: InChI=1S/C11H11NO3/c1-15-11(14)10(12-8-13)7-9-5-3-2-4-6-9/h2-6,10H,7H2,1H3/t10-/m0/s1
• InChIKey: JOTMMIYKEOOTNZ-JTQLQIEISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S)-2-isocyanato-3-phenylpropanoate
• IUPAC Traditional name: methyl (2S)-2-isocyanato-3-phenylpropanoate
• Synonyms: Methyl (S)-(-)-2-isocyanato-3-phenylpropionate; 甲基(S)-(-)-2-异氰酰基-3-苯基丙酸酯

Database IDs

• CAS Number: 40203-94-9
• MDL Number: MFCD00191535
• PubChem SID: 162239786; 24865670
• PubChem CID: 1514293

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 1.8063484
• LogD (pH = 7.4): 1.8063484
• Log P: 1.8063484
• Molar Refractivity: 53.3048 cm^3
• Polarizability: 20.816116 Å^3
• Polar Surface Area: 55.73 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 244 °C(lit.)
• Flash Point: 114.8 °F; 46 °C
• Density: 1.13 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.513(lit.)
• Optical Rotation: [α]20/D -80.0°, neat

Safety Information

• European Hazard Symbols: Harmful (Xn)
• UN Number: 2206
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 20/21/22-36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H226-H302-H312-H315-H319-H332-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2206 6.1/PG 3

Product Information

• Purity: 99%
• Linear Formula: C6H5CH2CH(NCO)CO2CH3

DETAILS

Sigma Aldrich - 409731

Packaging
1, 5 g in glass bottle
Application
This compound has been employed in the preparation of dipeptide analogs of angiotensinogen1 and Schiff base derivatives for the inhibition of thermolysin.2