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CAS No.: | 103-71-9 |
---|---|
Name: | Phenyl isocyanate |
Article Data: | 460 |
Molecular Structure: | |
Formula: | C7H5NO |
Molecular Weight: | 119.123 |
Synonyms: | Benzene, isocyanato-;Carbanil;Isocyanatobenzene;Mondur P;Phenyl carbonimide;Fenylisokyanat;Isocyanic acid, phenyl ester;Karbanil; |
EINECS: | 203-137-6 |
Density: | 1 g/cm3 |
Melting Point: | -31.3 °C |
Boiling Point: | 162-163 °C(lit.) |
Flash Point: | 132 °F |
Solubility: | Decomposes in water |
Appearance: | Colourless to light yellow liquid with an acrid odour |
Hazard Symbols: | T+ |
Risk Codes: | 22-26-36/37/38-42 |
Safety: | 26-28A-38-45 |
Transport Information: | UN 2487 6.1/PG 1 |
PSA: | 29.43000 |
LogP: | 1.65390 |
Conditions | Yield |
---|---|
In dichloromethane Irradiation; | 100% |
In acetonitrile for 16h; Inert atmosphere; Reflux; | 100% |
With water for 5h; Inert atmosphere; UV-irradiation; Sealed tube; chemoselective reaction; | 95% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane | 100% |
In ethyl acetate at 0 - 5℃; for 3h; Solvent; Cooling with ice; Reflux; | 89% |
In chloroform at 20℃; for 1h; Cooling with ice; | 85% |
Conditions | Yield |
---|---|
With Phenyltrichlorosilane at 100 - 180℃; for 1h; | 99% |
With phosphorus pentoxide | |
With phosphorus pentoxide at 170℃; under 100 Torr; man fraktioniert das ueberdestillierte Phenylisocyanat; |
2,3,5-triphenyl-4-thiazolone
dimethyl acetylenedicarboxylate
A
dimethyl 2,5-diphenylthiophene-3,4-dicarboxylate
B
phenyl isocyanate
Conditions | Yield |
---|---|
In xylene Heating; | A 99% B n/a |
Conditions | Yield |
---|---|
In toluene at -5 - 75℃; Solvent; | 98% |
Stage #1: phosgene; n-butyl isocyanide In chlorobenzene at 81℃; for 2.33333h; Stage #2: aniline In chlorobenzene at 81 - 88℃; for 1h; | 76% |
With 1-Chloronaphthalene at 230 - 240℃; unter Durchleiten durch ein Porzellanrohr; |
2-dimethylamino-5-(4-nitro-phenyl)-4-oxo-3-phenyl-4,5-dihydro-thiazolium betaine
dimethyl acetylenedicarboxylate
A
phenyl isocyanate
B
2-Dimethylamino-5-(4-nitro-phenyl)-thiophene-3,4-dicarboxylic acid dimethyl ester
Conditions | Yield |
---|---|
In xylene Heating; | A n/a B 98% |
2-cyano-5-(4-nitro-phenyl)-4-oxo-3-phenyl-4,5-dihydro-thiazolium betaine
dimethyl acetylenedicarboxylate
A
phenyl isocyanate
B
2-Cyano-5-(4-nitro-phenyl)-thiophene-3,4-dicarboxylic acid dimethyl ester
Conditions | Yield |
---|---|
In xylene Heating; | A n/a B 98% |
5-(4-nitro-phenyl)-4-oxo-2,3-diphenyl-4,5-dihydro-thiazolium betaine
dimethyl acetylenedicarboxylate
A
phenyl isocyanate
B
2-(4-Nitro-phenyl)-5-phenyl-thiophene-3,4-dicarboxylic acid dimethyl ester
Conditions | Yield |
---|---|
In xylene Heating; | A n/a B 97% |
Conditions | Yield |
---|---|
With air; palladium dichloride In 1,4-dioxane Heating; | 96% |
With mercury(II) oxide at 170℃; | |
Multi-step reaction with 3 steps 1: sodium hydride / 5,5-dimethyl-1,3-cyclohexadiene; mineral oil / 2 h / 20 °C / Inert atmosphere 2: chloroform / 1 h / 20 °C 3: acetonitrile / 25 °C View Scheme |
Conditions | Yield |
---|---|
In chlorobenzene at 160 - 240℃; under 11251.1 Torr; for 1h; Pressure; Solvent; Temperature; Inert atmosphere; Green chemistry; | 94.9% |
Reported in EPA TSCA Inventory.
DOT Classification: 6.1; Label: Poison; DOT Class: 6.1; Label: Poison, Flammable Liquid; DOT Class: 3; Label: Flammable Liquid, Poison
The Phenyl isocyanate with CAS registry number of 103-71-9 is also known as Benzene, isocyanato-. The IUPAC name is Isocyanatobenzene. It belongs to product categories of Organics; Derivatization Reagents; Derivatization Reagents HPLC; UV-VIS; Isocyanates; Nitrogen Compounds; Organic Building Blocks. Its EINECS registry number is 203-137-6. In addition, the formula is C7H5NO and the molecular weight is 119.13. This chemical is a colourless to light yellow liquid with an acrid odour that soluble in benzene, toluene, chloroform but decomposed in water and alcohol. It at low levels can cause damage to health that may destroy living tissue on contact and it should be sealed in ventilate, cool, dry place away from fire, heat.
Physical properties about Phenyl isocyanate are: (1)ACD/LogP: 2.58; (2)ACD/LogD (pH 5.5): 2.58; (3)ACD/LogD (pH 7.4): 2.58; (4)ACD/BCF (pH 5.5): 54.01; (5)ACD/BCF (pH 7.4): 54.01; (6)ACD/KOC (pH 5.5): 604.92; (7)ACD/KOC (pH 7.4): 604.92; (8)#H bond acceptors: 2; (9)#Freely Rotating Bonds: 1; (10)Index of Refraction: 1.522; (11)Molar Refractivity: 36.15 cm3; (12)Molar Volume: 118.4 cm3; (13)Surface Tension: 38.6 dyne/cm; (14)Density: 1 g/cm3; (15)Flash Point: 55.6 °C; (16)Enthalpy of Vaporization: 39.95 kJ/mol; (17)Boiling Point: 163 °C at 760 mmHg; (18)Vapour Pressure: 2.11 mmHg at 25 °C.
Preparation of Phenyl isocyanate: it is prepared by reaction of nitrobenzene with carbon monoxide. The reaction needs reagents Py, PyHCl and solvent chlorobenzene at the temperature of 205 °C for 1 hour. The yield is about 90%.
Uses of Phenyl isocyanate: it is used to produce 1-anilino-5,6-dihydro-6,6-dimethyl-3-phenylimino-4-cyano-8H-pyrano[3,4-c]pyran by reaction with (2,2-dimethyl-tetrahydro-pyran-4-ylidene)-malononitrile. The reaction occurs with reagent triethylamine and solvent dimethylformamide at 60 °C for 48 hours. The yield is about 35%.
When you are using this chemical, please be cautious about it. As a chemical, it is irritating to eyes, respiratory system and skin. Furthermore, it is harmful if swallowed, very toxic by inhalation and even may cause sensitisation by inhalation. It is harmful to aquatic organisms and it is flammable that may cause burns. During using it, wear suitable protective clothing, gloves and eye/face protection. Keep away from sources of ignition. After contact with skin, wash immediately. If contact with eyes accidently, rinse immediately with plenty of water and seek medical advice. In case of accident or if you feel unwell seek medical advice immediately. Because of insufficient ventilation wear suitable respiratory equipment.
You can still convert the following datas into molecular structure:
1. Canonical SMILES: C1=CC=C(C=C1)N=C=O
2. InChI: InChI=1S/C7H5NO/c9-6-8-7-4-2-1-3-5-7/h1-5H
3. InChIKey: DGTNSSLYPYDJGL-UHFFFAOYSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 50mg/kg (50mg/kg) | SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: CYANOSIS | National Technical Information Service. Vol. OTS0528337, |
mouse | LD50 | oral | 196mg/kg (196mg/kg) | Ecotoxicology and Environmental Safety. Vol. 17, Pg. 258, 1989. | |
mouse | LD50 | subcutaneous | 1400mg/kg (1400mg/kg) | Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 9, Pg. 759, 1967. | |
rabbit | LD50 | skin | 7130mg/kg (7130mg/kg) | Toxicology and Applied Pharmacology. Vol. 42, Pg. 417, 1977. | |
rat | LC50 | inhalation | 22mg/m3/4H (22mg/m3) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA LUNGS, THORAX, OR RESPIRATION: CYANOSIS | National Technical Information Service. Vol. OTS0530489, |
rat | LD50 | intraperitoneal | 100mg/kg (100mg/kg) | SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: TREMOR | National Technical Information Service. Vol. OTS0528337, |
rat | LD50 | oral | 800mg/kg (800mg/kg) | SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) | National Technical Information Service. Vol. OTS0528337, |
rat | LD50 | skin | 5mL/kg (5mL/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: AGGRESSION LUNGS, THORAX, OR RESPIRATION: DYSPNEA | National Technical Information Service. Vol. OTS0528430, |