“Phenyl isocyanate”的意思、由来-开放百科全书

词条

Phenyl isocyanate

释义

Structure
References
External links

| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 444049465
| ImageFile = Phenylisocyanate.svg
| ImageSize = 180px
| ImageAlt = Skeletal formula
| ImageFile1 = Phenyl-isocyanate-3D-balls.png
| ImageSize1 = 120
| ImageAlt1 = Ball-and-stick model
| PIN = Isocyanatobenzene
| OtherNames =
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 103-71-9
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = 196GO6BSOH
| PubChem = 7672
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 7389
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 53806
| SMILES = O=C=N/c1ccccc1
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI=1S/C7H5NO/c9-6-8-7-4-2-1-3-5-7/h1-5H
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = DGTNSSLYPYDJGL-UHFFFAOYSA-N
|Section2={{Chembox Properties
| C=7 | H=5 | N=1 | O=1
| Appearance = Colourless liquid
| Density = 1.09
| MeltingPt = -30 °C
| BoilingPt = 165 °C
| Solubility = Reacts with water
| MagSus = -72.7·10⁻⁶ cm³/mol
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}

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 is therefore handled with care.

Characteristic of other isocyanates, it reacts with amines to give ureas.^[1] 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 RCNO in the reaction, with CO₂ as one of the by products.^[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.^[3]

References

1. ^Emmanuil I. Troyansky "Phenyl Isocyanate" in Encyclopedia of Reagents for Organic Synthesis, 2001 John Wiley & Sons {{DOI|10.1002/047084289X.rp073}}
2. ^{{Cite journal | last1 = Mukaiyama | first1 = Teruaki | last2 = Hoshino | first2 = Toshio | title = The Reactions of Primary Nitroparaffins with Isocyanates | journal = Journal of the American Chemical Society | volume = 82 | pages = 5339 | year = 1960 | doi = 10.1021/ja01505a017}}
3. ^{{cite journal|title=Porphyrin Sponges: Conservative of Host Structure in over 200 Porphyrin-Based Lattice Clathrates|authors=Marianne P. Byrn, Carol J. Curtis, Yu Hsiou, Saeed I. Khan, Philip A. Sawin, S. Kathleen Tendick, Aris Terzis, Charles E. Strouse|journal=J. Am. Chem. Soc.|year=1993|volume= 115|pages=9480–9497|doi=10.1021/ja00074a013}}

External links

Phenyl Isocyanate Data Sheet

2 : Isocyanates|Phenyl compounds

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