isocyanatobenzene

• ChemBase ID: 76528
• Molecular Formular: C7H5NO
• Molecular Mass: 119.1207
• Monoisotopic Mass: 119.03711379
• SMILES: N(=C=O)c1ccccc1
• Canonical SMILES: O=C=Nc1ccccc1
• InChI: InChI=1S/C7H5NO/c9-6-8-7-4-2-1-3-5-7/h1-5H
• InChIKey: DGTNSSLYPYDJGL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: isocyanatobenzene
• IUPAC Traditional name: phenyl isocyanate
• Synonyms: isocyanatobenzene; Isocyanatobenzene; Phenyl isocyanate; Phenyl isocyanate; Phenylisocyanate; 异氰酸苯酯

Database IDs

• CAS Number: 103-71-9
• EC Number: 203-137-6
• MDL Number: MFCD00001994
• Beilstein Number: 471391
• Merck Index: 147296
• PubChem SID: 24887345; 162041432; 24850685; 24887343
• PubChem CID: 7672
• CHEBI ID: 53806
• Chemspider ID: 7389
• Wikipedia Title: Phenylisocyanate

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.8828014
• LogD (pH = 7.4): 1.8828014
• Log P: 1.8828014
• Molar Refractivity: 35.13 cm^3
• Polarizability: 12.632254 Å^3
• Polar Surface Area: 29.43 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Reacts with water
• Apperance: Colourless liquid
• Melting Point: -30 °C(lit.); -30°C; -33°C
• Boiling Point: 158°C; 162-163 °C(lit.); 162-164°C; 62-64°C/11mm
• Flash Point: 123.8 °F; 51 °C; 51°C; 51°C(123°F)
• Density: 1.09; 1.094; 1.096; 1.096 g/mL at 25 °C(lit.); 1.1 g/ml
• Refractive Index: 1.535; 1.5360; n20/D 1.535(lit.); n20/D 1.536
• Vapor Pressure: 1.4 mmHg ( 20 °C)

Safety Information

• Storage Warning: Moisture Sensitive; Very Toxic/Corrosive/Store under Argon/Moisture Sensitive/Keep Cold
• RTECS: DA3675000
• European Hazard Symbols: Highly toxic (T+); Harmful (Xn)
• UN Number: 2487; UN2487
• German water hazard class: 2
• Hazard Class: 6.1
• Packing Group: 1; I
• Risk Statements: 10-22-26-34-42/43; 10-22-26-34-42-52; R:22-36-42/43
• Safety Statements: 16-26-28-36/37/39-45; 23-26-28-36/37/39-45; S:23-24-36/37/39-45-51
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS05; GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H226-H302-H314-H317-H330-H334; H301-H330-H317-H334-H314-H318-H226
• GHS Precautionary statements: P210-P301+P310-P303+P361+P353-P304+P340-P305+P351+P338-P320-P330-P405-P501A; P260-P280-P284-P305 + P351 + P338-P310
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2487 6.1/PG 1
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98%; ≥98.0% (GC); ≥99.0% (GC); 98+%
• Grade: puriss. p.a.; technical
• Quality: for the detection of alcohols and amines
• Linear Formula: C6H5NCO

DETAILS

MP Biomedicals - 05217403

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 185353

Packaging
100, 500 g in Sure/Seal™
5 g in glass bottle

Sigma Aldrich - 78750

Other Notes
Reagent for the determination of alcohols and amines1

REFERENCES

• For general reactions of isocyanates, see Appendix 3.
• Can be used, in the presence of pyridine, to protect alcohols as N-phenylcarbamates: J. Am. Chem. Soc., 94, 3578 (1972), e.g. selective protection of primary OH groups in pyranosides; cleavage by reduction with LiAlH₄: Tetrahedron Lett., 28, 4165 (1987). The group can also be cleaved by refluxing with NaOMe: Acta Chem. Scand., 15, 87, 96 (1961). Amines may also be protected as N-phenylcarbamates: Tetrahedron Lett., 1935 (1977).
• Forms ureas by reaction with amines; e.g. Tris(2-aminoethyl)amine, B21789, gives a molecule containing three urea groups which was used in studies of spacers for phosphate receptors: Chem. Lett., 759 (1995). Reaction with 4-aminobenzimidazole derivatives has been used in the synthesis of 1-phenylxanthine derivatives: Synthesis, 855 (1995).
• In the presence of triethylamine, dehydrates nitroalkanes to nitrile oxides, which can undergo 1,3-dipolar cycloadditions: J. Am. Chem. Soc., 82, 5339 (1960); Synthesis, 757 (1980). Similarly, aldoximes are converted to nitriles: J. Org. Chem., 26, 782 (1961).
• Conversion to diphenylcarbodiimide can be catalyzed by 3-Methyl-1-phenyl-2-phospholene 1-oxide, A11792: Org. Synth. Coll., 5, 501 (1973).