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104-12-1

Basic Information
CAS No.: 104-12-1
Name: 4-Chlorophenyl isocyanate
Article Data: 116
Molecular Structure:
Molecular Structure of 104-12-1 (4-Chlorophenyl isocyanate)
Formula: C7H4ClNO
Molecular Weight: 153.568
Synonyms: Chlorophenyl isocyanate;Isocyanic acid, p-chlorophenyl ester;1-Chloro-4-isocyanatobenzene;4-Chloroisocyanatobenzene;4-Chlorophenyl isocyanate;HSDB 1331;NSC 76589;PCPI;p-Chlorfenylisokyanat;p-Chlorfenylisokyanat;para-Chlorophenyl isocyanate;
EINECS: 203-176-9
Density: 1.26 g/cm3
Melting Point: 26-29 °C(lit.)
Boiling Point: 204.2 °C at 760 mmHg
Flash Point: 76 °C
Solubility: decomposes in water
Appearance: colorless to light yellow liquid or crystal
Hazard Symbols: VeryT+,ToxicT,CorrosiveC
Risk Codes: 25-26-37/38-41-42-52/53
Safety: 23-26-28-36/37/39-45-61-38-37/39-28A-22
Transport Information: UN 2811 6.1/PG 2
PSA: 29.43000
LogP: 2.30730
Synthetic route
124-38-9

carbon dioxide

31641-65-3

N-p-chlorophenyltriphenylphosphinimine

104-12-1

p-chlorphenylisocyanate

Conditions
ConditionsYield
In benzene for 2h; Heating;97%
32315-10-9

bis(trichloromethyl) carbonate

106-47-8

4-chloro-aniline

104-12-1

p-chlorphenylisocyanate

Conditions
ConditionsYield
In ethyl acetate at 0 - 5℃; for 3h; Solvent; Cooling with ice; Reflux;92%
In 1,2-dichloro-ethane at 70 - 83℃;89.4%
Stage #1: bis(trichloromethyl) carbonate; 4-chloro-aniline In dichloromethane at 20℃; for 0.5h;
Stage #2: With triethylamine In dichloromethane at -35 - 20℃; for 2h;
84%
2417-72-3

Methyl 4-(bromomethyl)benzoate

N-(4-chlorophenyl)thiomorpholine-4-carboxamide 1,1-dioxide

104-12-1

p-chlorphenylisocyanate

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 3h;77.1%

(2S,3S)-1-(4-Chloro-phenyl)-3-methyl-4-oxo-azetidine-2-carbaldehyde

A

104-12-1

p-chlorphenylisocyanate

B

[(Z)-4-Chloro-phenylimino]-acetaldehyde

Conditions
ConditionsYield
at 550℃; under 0.002 Torr;A 8%
B 77%
21368-28-5

4-chlorobenzoyl azide

104-12-1

p-chlorphenylisocyanate

Conditions
ConditionsYield
In toluene for 1.5h; Heating;75%
In toluene at 100℃; for 1h; Reflux;
Curtius Rearrangement;
17574-84-4

1-methoxy-2-methylprop-1-ene

36176-95-1

4-chloro-N-(dimethyl-λ4-sulfanylidene)benzamide

A

54573-19-2

4,4-dimethyl-5-methoxy-2-(4-chlorophenyl)-2-oxazoline

B

104-12-1

p-chlorphenylisocyanate

C

619-56-7

4-chlorobenzamide

Conditions
ConditionsYield
In benzene at 35℃; for 1h; Mechanism; Product distribution; Irradiation; other temperatures, other solvents, other concentration of reactant;A 49%
B n/a
C n/a
201230-82-2

carbon monoxide

100-00-5

4-chlorobenzonitrile

104-12-1

p-chlorphenylisocyanate

Conditions
ConditionsYield
With di(rhodium)tetracarbonyl dichloride; pyridine hydrochloride In chlorobenzene at 185℃; under 38000 Torr; for 1h;49%
bis(tetrahydrofurane)oxovanadium(IV) dichloride; (Bu4N) In 1,2-dichloro-benzene at 120℃; under 750.06 Torr;18%
bis(tetrahydrofurane)oxovanadium(IV) dichloride; (Bu4N) In 1,2-dichloro-benzene at 120℃; under 750.06 Torr; Rate constant;18%
With pyridine; di(rhodium)tetracarbonyl dichloride; pyridine hydrochloride In chlorobenzene at 205℃; under 50 Torr; for 0.666667h; Yield given;
17738-71-5

2-((4-chlorophenyl)-amino)-2-oxoacetic acid

104-12-1

p-chlorphenylisocyanate

Conditions
ConditionsYield
With ammonium peroxydisulfate; silver nitrate; copper(II) sulfate In dichloromethane; water at 40℃; for 3h;46%
With ammonium peroxydisulfate; copper diacetate; silver nitrate In dichloromethane; water at 40℃; for 3h;46%
17574-84-4

1-methoxy-2-methylprop-1-ene

132401-91-3

3-(4-chlorophenyl)-1,4,2-dioxazol-5-one

A

54573-19-2

4,4-dimethyl-5-methoxy-2-(4-chlorophenyl)-2-oxazoline

B

104-12-1

p-chlorphenylisocyanate

Conditions
ConditionsYield
In dichloromethane Irradiation;A 9%
B 42%
132401-91-3

3-(4-chlorophenyl)-1,4,2-dioxazol-5-one

A

54573-19-2

4,4-dimethyl-5-methoxy-2-(4-chlorophenyl)-2-oxazoline

B

104-12-1

p-chlorphenylisocyanate

Conditions
ConditionsYield
With 1-methoxy-2-methylprop-1-ene In dichloromethane Irradiation;A 9%
B 42%
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Specification

The IUPAC name of 4-Chlorophenyl isocyanate is 1-chloro-4-isocyanatobenzene. With the CAS registry number 104-12-1, it is also named as Isocyanic acid, p-chlorophenyl ester. The classification codes are Human Data; Skin / Eye Irritant. It is colorless to light yellow liquid or crystal which decomposes in water and is soluble in toluene, xylene and other organic solvents. Additionally, this chemical should be sealed in the container and stored in the cool and dry place.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 3.42; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.42; (4)ACD/LogD (pH 7.4): 3.42; (5)ACD/BCF (pH 5.5): 234.5; (6)ACD/BCF (pH 7.4): 234.5; (7)ACD/KOC (pH 5.5): 1730.42; (8)ACD/KOC (pH 7.4): 1730.42; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1; (12)Index of Refraction: 1.55; (13)Molar Refractivity: 40.75 cm3; (14)Molar Volume: 127.8 cm3; (15)Polarizability: 16.15×10-24 cm3; (16)Surface Tension: 41.3 dyne/cm; (17)Enthalpy of Vaporization: 44.05 kJ/mol; (18)Vapour Pressure: 0.266 mmHg at 25°C; (19)Rotatable Bond Count: 1; (20)Exact Mass: 152.998141; (21)MonoIsotopic Mass: 152.998141; (22)Topological Polar Surface Area: 29.4; (23)Heavy Atom Count: 10; (24)Complexity: 146.

Preparation of 4-Chlorophenyl isocyanate: Adding chloroaniline and toluene in the reactor, and stirring to the chloroaniline dissolve. And then passing phosgene at the low-temperature. After passing a certain amount of phosgene, transfer the material into the thermal reactor, and heating to about 105 °C. The materials become transparent, then refluxing a certain time, passing nitrogen gas to remove phosgene. Finally, we can get the product by cooling.

Uses of 4-Chlorophenyl isocyanate: It is used as an intermediate in pesticide and pharmaceutical manufacture. And it also can react with 1-methyl-5-methylsulfanyl-2,3-dihydro-pyrrole to get 1,3-bis-(4-chloro-phenyl)-7-methyl-1,5,6,7-tetrahydro-pyrrolo[2,3-d]pyrimidine-2,4-dione. This reaction needs solvent toluene by heating. The reaction time is 15 hours. The yield is 36%.

When you are using this chemical, please be cautious about it as the following:
It is toxic if swallowed and irritating to respiratory system and skin, so peole should not breathe dust. And it is also harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. After contact with skin, wash immediately with plenty of soap-suds. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 

People can use the following data to convert to the molecule structure.
1. SMILES:Clc1ccc(\N=C=O)cc1
2. InChI:InChI=1/C7H4ClNO/c8-6-1-3-7(4-2-6)9-5-10/h1-4H

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mammal (species unspecified) LC50 inhalation 53mg/m3 (53mg/m3)   Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 11(4), Pg. 23, 1967.
man TCLo inhalation 800ug/m3/1M (0.8mg/m3) SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Hygiene and Sanitation Vol. 31(7-9), Pg. 481, 1966.
mouse LC50 inhalation 53mg/m3 (53mg/m3) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: EXCITEMENT

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 31(9), Pg. 108, 1966.
mouse LD50 oral 450mg/kg (450mg/kg)   "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 38, 1982.
rabbit LDLo skin 6gm/kg (6000mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: MUSCLE WEAKNESS
National Technical Information Service. Vol. OTS0528442,
rat LC50 inhalation 113mg/m3/4H (113mg/m3) SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

GASTROINTESTINAL: OTHER CHANGES
National Technical Information Service. Vol. OTS0555462,
rat LD skin > 1gm/kg (1000mg/kg)   National Technical Information Service. Vol. OTS0538092,
rat LD50 oral 138mg/kg (138mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

GASTROINTESTINAL: GASTRITIS
National Technical Information Service. Vol. OTS0528437,
rat LDLo intraperitoneal 62500ug/kg (62.5mg/kg)   National Technical Information Service. Vol. OTS0538092,