Phenyl isocyanate

Names
Preferred IUPAC name

Isocyanatobenzene

Identifiers

CAS Number

* 103-71-9 Y

3D model (JSmol)

* Interactive image

ChEBI |

* CHEBI:53806 Y

ChemSpider |

* 7389 Y

ECHA InfoCard | 100.002.852
EC Number |

* 203-137-6

PubChem CID

* 7672

UNII |

* 196GO6BSOH N

UN number | 2487

CompTox Dashboard (EPA)

* DTXSID5051521

InChI

* InChI=1S/C7H5NO/c9-6-8-7-4-2-1-3-5-7/h1-5H Y

Key: DGTNSSLYPYDJGL-UHFFFAOYSA-N Y

SMILES

* O=C=N/c1ccccc1

Properties

Chemical formula

| C7H5NO
Molar mass | 119.123 g·mol−1
Appearance  | Colourless liquid
Density | 1.09
Melting point | −30 °C (−22 °F; 243 K)
Boiling point | 165 °C (329 °F; 438 K)

Solubility in water

| Reacts with water

Magnetic susceptibility (χ)

| −72.7·10−6 cm3/mol
Hazards
GHS labelling:[1]

Pictograms

Signal word

| Danger

Hazard statements

| H226, H302, H314, H317, H330, H334, H335, H410, H411

Precautionary statements

| P210, P233, P240, P241, P242, P243, P260, P261, P264, P264+P265, P270, P271, P272, P273, P280, P284, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P317, P319, P320, P321, P330, P333+P317, P342+P316, P362+P364, P363, P370+P378, P391, P403, P403+P233, P403+P235, P405, P501

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

N verify (what is YN ?)

Infobox references

Chemical compound

Phenyl isocyanate is an organic compound typically abbreviated PhNCO. The molecule consists of a phenyl ring attached to the isocyanate functional group. It is a colourless liquid that reacts with water. Phenyl isocyanate has a strong odor and tearing vapours, therefore it has to be handled with care.

Characteristic of other isocyanates, it reacts with amines to give ureas.[2] Similarly, reacts with alcohols to form carbamates.

It is used in addition with triethylamine to activate nitro groups to undergo (C,O) 1,3-dipolar cycloaddition (as opposed to O,O). The nitro group (RCH2NO2) is converted to oxime-like dimers in the reaction:[3]

4 PhNCO \+ 2 RCH2NO2 → 2(PhNH)2CO \+ 2 CO2 \+ (RCNO)2

## Structure

[edit]

PhNCO is a planar molecule, according to X-ray crystallography. The N=C=O linkage is nearly linear. The C=N and C=O distances are respectively 1.195 and 1.173 Å.[4]

## References

[edit]

1. ^ "Phenyl isocyanate". pubchem.ncbi.nlm.nih.gov.
2. ^ Emmanuil I. Troyansky "Phenyl Isocyanate" in Encyclopedia of Reagents for Organic Synthesis, 2001 John Wiley & Sons doi:10.1002/047084289X.rp073
3. ^ Mukaiyama, Teruaki; Hoshino, Toshio (1960). "The Reactions of Primary Nitroparaffins with Isocyanates". Journal of the American Chemical Society. 82 (20): 5339–5342\. doi:10.1021/ja01505a017.
4. ^ Marianne P. Byrn; Carol J. Curtis; Yu Hsiou; Saeed I. Khan; Philip A. Sawin; S. Kathleen Tendick; Aris Terzis; Charles E. Strouse (1993). "Porphyrin Sponges: Conservative of Host Structure in over 200 Porphyrin-Based Lattice Clathrates". J. Am. Chem. Soc. 115 (21): 9480–9497\. doi:10.1021/ja00074a013.

## External links

[edit]

* Phenyl Isocyanate Data Sheet

*[CID]: Compound ID
*[EPA]: U.S. Environmental Protection Agency
*[H226]: H226: Flammable liquid and vapour
*[H302]: H302: Harmful if swallowed
*[H314]: H314: Causes severe skin burns and eye damage
*[H317]: H317: May cause an allergic skin reaction
*[H330]: H330: Fatal if inhaled
*[H334]: H334: May cause allergy or asthma symptoms of breathing difficulties if inhaled
*[H335]: H335: May cause respiratory irritation
*[H410]: H410: Very toxic to aquatic life with long lasting effects
*[H411]: H411: Toxic to aquatic life with long lasting effects
*[P210]: P210: Keep away from heat, hot surfaces, sparks, open flames and other ignition sources. No smoking.
*[P233]: P233: Keep container tightly closed.
*[P240]: P240: Ground and bond container and receiving equipment.
*[P241]: P241: Use explosion-proof electrical/ventilating/light/.../equipment.
*[P242]: P242: Use only non-sparking tools.
*[P243]: P243: Take precautionary measures to prevent static discharges.
*[P260]: P260: Do not breathe dust/fume/gas/mist/vapours/spray.
*[P261]: P261: Avoid breathing dust/fume/gas/mist/vapours/spray.
*[P264]: P264: Wash ... thoroughly after handling.
*[P264+P265]: P264+P265: Wash ... thoroughly after handling. Do not touch eyes.
*[P270]: P270: Do not eat, drink or smoke when using this product.
*[P271]: P271: Use only outdoors or in a well-ventilated area.
*[P272]: P272: Contaminated work clothing should not be allowed out of the workplace.
*[P273]: P273: Avoid release to the environment.
*[P280]: P280: Wear protective gloves/protective clothing/eye protection/face protection.
*[P284]: P284: Wear respiratory protection.
*[P301+P317]: P301+P317: IF SWALLOWED: IF SWALLOWED: Get medical help.
*[P301+P330+P331]: P301+P330+P331: IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
*[P302+P352]: P302+P352: IF ON SKIN: Wash with soap and water.
*[P302+P361+P354]: P302+P361+P354: IF ON SKIN: Take off Immediately all contaminated clothing. Immediately rinse with water for several minutes.
*[P303+P361+P353]: P303+P361+P353: IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water [or shower].
*[P304+P340]: P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing.
*[P305+P354+P338]: P305+P354+P338: IF IN EYES: Immediately rinse with water for several minutes. Remove contact lenses if present and easy to do. Continue rinsing.
*[P316]: P316: Get immediate emergency medical help.
*[P317]: P317: Get emergency medical help.
*[P319]: P319: Get medical help if you feel unwell.
*[P320]: P320: Specific treatment is urgent (see ... on this label).
*[P321]: P321: Specific treatment (see ... on this label).
*[P330]: P330: Rinse mouth.
*[P333+P317]: P333+P317: If skin irritation or rash occurs: Get medical help.
*[P342+P316]: P342+P316: If experiencing respiratory symptoms: Get emergence medical help immediately.
*[P362+P364]: P362+P364: Take off contaminated clothing and wash it before reuse.
*[P363]: P363: Wash contaminated clothing before reuse.
*[P370+P378]: P370+P378: In case of fire: Use ... to extinguish.
*[P391]: P391: Collect spillage.
*[P403]: P403: Store in a well ventilated place.
*[P403+P233]: P403+P233: Store in a well ventilated place. Keep container tightly closed.
*[P403+P235]: P403+P235: Store in a well ventilated place. Keep cool.
*[P405]: P405: Store locked up.
*[P501]: P501: Dispose of contents/container to ...