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

EC Number |

* 203-137-6

PubChem CID

* 7672

UNII |

* 196GO6BSOH N

UN number | 2487

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 pictograms |
GHS Signal word | Danger

GHS hazard statements

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

GHS precautionary statements

| P210, P233, P240, P241, P242, P243, P260, P261, P264, P264+265Script error: No such module "Preview warning".Category:GHS errors, P270, P271, P272, P273, P280, P284, P301+317Script error: No such module "Preview warning".Category:GHS errors, P301+330+331, P302+352, P302+361+354Script error: No such module "Preview warning".Category:GHS errors, P303+361+353, P304+340, P305+354+338Script error: No such module "Preview warning".Category:GHS errors, P316Script error: No such module "Preview warning".Category:GHS errors, P317Script error: No such module "Preview warning".Category:GHS errors

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

Tracking categories (test):

* SizeSet

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

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

1. ↑ "Phenyl isocyanate" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/7672#section=Safety-and-Hazards.
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

* Phenyl Isocyanate Data Sheet

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Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:Phenyl_isocyanate&oldid=4175241"
*[CID]: Compound ID
*[H226]: Flammable liquid and vapour
*[H302]: Harmful if swallowed
*[H314]: Causes severe skin burns and eye damage
*[H317]: May cause an allergic skin reaction
*[H330]: Fatal if inhaled
*[H334]: May cause allergy or asthma symptoms of breathing difficulties if inhaled
*[H335]: May cause respiratory irritation
*[H410]: Very toxic to aquatic life with long lasting effects
*[H411]: Toxic to aquatic life with long lasting effects
*[P210]: Keep away from heat/sparks/open flames/hot surfaces – No smoking
*[P233]: Keep container tightly closed
*[P240]: Ground/bond container and receiving equipment
*[P241]: Use explosion-proof electrical/ventilating/light/…/equipment
*[P242]: Use only non-sparking tools
*[P243]: Take precautionary measures against static discharge
*[P260]: Do not breathe dust/fume/gas/mist/vapours/spray
*[P261]: Avoid breathing dust/fume/gas/mist/vapours/spray
*[P264]: Wash … thoroughly after handling
*[P270]: Do not eat, drink or smoke when using this product
*[P271]: Use only outdoors or in a well-ventilated area
*[P272]: Contaminated work clothing should not be allowed out of the workplace
*[P273]: Avoid release to the environment
*[P280]: Wear protective gloves/protective clothing/eye protection/face protection
*[P284]: Wear respiratory protection
*[P301+330+331]: IF SWALLOWED: Rinse mouth. Do NOT induce vomiting
*[P302+352]: IF ON SKIN: Wash with soap and water
*[P303+361+353]: IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower
*[P304+340]: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing