(isocyanatomethyl)benzene

• ChemBase ID: 35898
• Molecular Formular: C8H7NO
• Molecular Mass: 133.14728
• Monoisotopic Mass: 133.05276385
• SMILES: C(=NCc1ccccc1)=O
• Canonical SMILES: O=C=NCc1ccccc1
• InChI: InChI=1S/C8H7NO/c10-7-9-6-8-4-2-1-3-5-8/h1-5H,6H2
• InChIKey: YDNLNVZZTACNJX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (isocyanatomethyl)benzene
• IUPAC Traditional name: (isocyanatomethyl)benzene
• Synonyms: (Isocyanatomethyl)benzene; Benzyl isocyanate 98%; (Isocyanatomethyl)benzene; Benzyl isocyanate; 异氰酸苄酯

Database IDs

• CAS Number: 3173-56-6
• EC Number: 221-640-9
• MDL Number: MFCD00009701
• Beilstein Number: 636508
• PubChem SID: 24853269; 160999205
• PubChem CID: 76639

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.6818535
• LogD (pH = 7.4): 1.6818535
• Log P: 1.6818535
• Molar Refractivity: 37.9508 cm^3
• Polarizability: 14.496511 Å^3
• Polar Surface Area: 29.43 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 101-104 °C/33 mmHg(lit.); 101-104°C/33mm; 53-54°C/0.8mm
• Flash Point: 113 °F; 43°C(109°F); 45 °C; 45°C
• Density: 1.070; 1.078; 1.078 g/mL at 25 °C(lit.)
• Refractive Index: 1.5250; 1.5261; n20/D 1.526(lit.)
• Hydrophobicity(logP): 0.899

Safety Information

• Storage Warning: Moisture Sensitive; TOXIC, FLAMMABLE; Toxic/Flammable/Irritant/Lachrymatory/Moisture Sensitive/Keep Cold/Store under Argon
• European Hazard Symbols: Toxic (T); Harmful (Xn)
• UN Number: 3080; UN3080
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2; II
• Risk Statements: 10-23/25-36/37/38-42; 10-36/37/38-42/43
• Safety Statements: 23-26-36/37; 23-26-36/37-45
• TSCA Listed: false; 否
• GHS Pictograms: GHS02; GHS06; GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H226-H315-H317-H319-H334-H335; H301-H330-H315-H319-H335-H334-H226
• GHS Precautionary statements: P210-P301+P310-P303+P361+P353-P304+P340-P305+P351+P338-P320-P330-P405-P501A; P261-P280-P305 + P351 + P338-P342 + P311
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3080 6.1/PG 2

Product Information

• Purity: 95%; 98%; 99%
• Linear Formula: C6H5CH2NCO

DETAILS

Sigma Aldrich - 227269

Application
Used in a multicomponent, stereospecific synthesis of 1,3-oxazinane-2,4-diones employing an Al-salph complex (674699).1
Packaging
5, 25 g in glass bottle

REFERENCES

• Protected ammonia equivalent in the stereoselective ring-opening of chiral 2,3-epoxy alcohols (from Sharpless asymmetric epoxidation). The key step in the sequence involves intramolecular cyclization of the carbamate intermediate: J. Org. Chem., 50, 3752 (1985):
  
• For general reactions of isocyanates, see Appendix 3.