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327-78-6

Basic Information
CAS No.: 327-78-6
Name: Benzene,1-chloro-4-isocyanato-2-(trifluoromethyl)-
Molecular Structure:
Molecular Structure of 327-78-6 (Benzene,1-chloro-4-isocyanato-2-(trifluoromethyl)-)
Formula: C8H3ClF3NO
Molecular Weight: 221.56
Synonyms: 4-Chloro-a,a,a-trifluoro-m-tolyl isocyanate;4-Chloro-1-isocyanato-3-trifluoromethylbenzene;3-Trifluoromethyl-4-chlorophenyl isocyanate;Isocyanicacid, 4-chloro-a,a,a-trifluoro-m-tolyl ester (8CI);1-Chloro-4-isocyanato-2-(trifluoromethyl)benzene;
EINECS: -0
Density: 1.4 g/cm3
Melting Point: 40-42 °C(lit.)
Boiling Point: 201.7 °C at 760 mmHg
Flash Point: 84.9 °C
Solubility: Insoluble in water
Appearance: White solid or melt
Hazard Symbols: HarmfulXn
Risk Codes: 20/21/22-36/37-36/37/38-42-20/22
Safety: 7-26-27-37/39-36/37/39-45-23
Transport Information: UN 2206 6.1/PG 3
PSA: 29.43000
LogP: 3.32610
Synthetic route
32315-10-9

bis(trichloromethyl) carbonate

320-51-4

4-chloro-3-trifluoromethyl-aniline

327-78-6

4-chloro-3-(trifluoromethyl)phenyl isocyanate

Conditions
ConditionsYield
With triethylamine In dichloromethane100%
In ethyl acetate at 80℃; for 1h;99.2%
In ethyl acetate at -5 - 80℃; for 3h; Solvent;95%
75-44-5

phosgene

320-51-4

4-chloro-3-trifluoromethyl-aniline

327-78-6

4-chloro-3-(trifluoromethyl)phenyl isocyanate

320-51-4

4-chloro-3-trifluoromethyl-aniline

503-38-8

trichloromethyl chloroformate

327-78-6

4-chloro-3-(trifluoromethyl)phenyl isocyanate

Conditions
ConditionsYield
In benzene for 12h; Product distribution / selectivity; Reflux;
for 12h; Reflux;
In benzene for 12h; Reflux;
88-16-4

1-chloro-2-(trifluoromethyl)benzene

327-78-6

4-chloro-3-(trifluoromethyl)phenyl isocyanate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: acetic anhydride; nitric acid / 3 h / 10 - 12 °C
2: iron(III) chloride hexahydrate; hydrazine hydrate / ethanol / 3 h / Reflux
3: dmap / 1,2-dichloro-ethane / -5 - 5 °C / Reflux
View Scheme
Multi-step reaction with 3 steps
1: sulfuric acid; nitric acid / water / 18 h / 0 - 20 °C / Inert atmosphere; Schlenk technique
2: iron; ammonium chloride; hydrogenchloride / ethanol; water / 2 h / 80 °C / Inert atmosphere; Schlenk technique
3: N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 20 °C / Inert atmosphere; Schlenk technique
View Scheme
320-51-4

4-chloro-3-trifluoromethyl-aniline

530-62-1

1,1'-carbonyldiimidazole

327-78-6

4-chloro-3-(trifluoromethyl)phenyl isocyanate

Conditions
ConditionsYield
In dichloromethane at 50℃; for 16h;
777-37-7

4-chloro-3-(trifluoromethyl)nitrobenzene

327-78-6

4-chloro-3-(trifluoromethyl)phenyl isocyanate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: iron; ammonium chloride; hydrogenchloride / ethanol; water / 2 h / 80 °C / Inert atmosphere; Schlenk technique
2: N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 20 °C / Inert atmosphere; Schlenk technique
View Scheme
330796-23-1

2-aminomethyl-3-(4-fluoro-phenyl)-3H-quinazolin-4-one

327-78-6

4-chloro-3-(trifluoromethyl)phenyl isocyanate

330796-24-2

1-(4-chloro-3-trifluoromethylphenyl)-3-[3-(4-fluorophenyl)-4-oxo-3,4-dihydroquinazolin-2-ylmethyl]urea

Conditions
ConditionsYield
In dichloromethane at 20℃;100%
In chloroform98%
327-78-6

4-chloro-3-(trifluoromethyl)phenyl isocyanate

210907-84-9

3-aminophenylboronic acid pinacolate

1258961-70-4

1-(4-chloro-3-trifluoromethyl-phenyl)-3-[3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-urea

Conditions
ConditionsYield
In dichloromethane100%
In dichloromethane for 0.333333h;
884339-72-4

4-(4-amino-3-(trifluoromethyl)phenoxy)-3-nitropyridin-2-amine

327-78-6

4-chloro-3-(trifluoromethyl)phenyl isocyanate

884340-04-9

1-(4-(2-amino-3-nitropyridin-4-yloxy)-2-(trifluoromethyl)phenyl)-3-(4-chloro-3-(trifluoromethyl)phenyl)urea

Conditions
ConditionsYield
at 20℃; for 20h; Inert atmosphere;99%

N-(4-amino-2-methylphenyl)-5-methylisoxazole-4-carboxamide

327-78-6

4-chloro-3-(trifluoromethyl)phenyl isocyanate

5-methylisoxazole-4-carboxylic acid {4-[3-(4-chloro-3-(trifluoromethyl)phenyl)ureido]-2-methylphenyl}amide

Conditions
ConditionsYield
In tetrahydrofuran at 20℃;99%
In tetrahydrofuran at 20℃;49%
288-32-4

1H-imidazole

327-78-6

4-chloro-3-(trifluoromethyl)phenyl isocyanate

1187086-96-9

N-[4-chloro-3-(trifluoromethyl)phenyl]-1H-imidazole-1-carboxamide

Conditions
ConditionsYield
In chloroform at 0 - 20℃; for 2h;98%
1160825-66-0

7-(4-amino-2-methoxyphenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one

327-78-6

4-chloro-3-(trifluoromethyl)phenyl isocyanate

1160825-37-5

1-(4-(2,3-dihydro-2-oxo-1H-imidazo[4,5-b]pyridin-7-yloxy)-3-methoxyphenyl)-3-(4-chloro-3-(trifluoromethyl)phenyl)urea

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 14h;98%

4-(4-aminophenoxy)-N-cyclopentylpyridine-2-carboxamide

327-78-6

4-chloro-3-(trifluoromethyl)phenyl isocyanate

4-[4-[[4-chloro-3-(trifluoromethyl)phenyl]carbamoylamino]phenoxy]-N-cyclopentylpyridine-2-carboxamide

Conditions
ConditionsYield
In dichloromethane at 20℃; for 16h; Inert atmosphere;98%
39959-54-1

3-bromobenzylamine hydrochloride

327-78-6

4-chloro-3-(trifluoromethyl)phenyl isocyanate

847606-86-4

1-(3-bromo-benzyl)-3-(4-chloro-3-trifluoromethyl-phenyl)-urea

Conditions
ConditionsYield
With triethylamine In acetonitrile at 0 - 20℃; for 3h;97.8%
26177-43-5

3-nitrobenzylamine hydrochloride

327-78-6

4-chloro-3-(trifluoromethyl)phenyl isocyanate

847606-82-0

1-(4-chloro-3-trifluoromethyl-phenyl)-3-(3-nitro-benzyl)-urea

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide; acetonitrile at 0 - 20℃; for 2h;97%
2634-33-5

1,2-benzisothiazolin-3-one

327-78-6

4-chloro-3-(trifluoromethyl)phenyl isocyanate

1437999-63-7

N-[4-chloro-3-(trifluoromethyl)phenyl]benzisothiazol-3-one-2-amide

Conditions
ConditionsYield
In tetrahydrofuran; dichloromethane for 0.5h; Reflux;97%

C11H14BrN5

327-78-6

4-chloro-3-(trifluoromethyl)phenyl isocyanate

C19H17BrClF3N6O

Conditions
ConditionsYield
In dichloromethane at 20℃; for 3h;96.5%
685533-75-9

3-(4-pyridinyloxy)benzylamine

327-78-6

4-chloro-3-(trifluoromethyl)phenyl isocyanate

685533-66-8

1-(4-chloro-3-trifluoromethylphenyl)-3-[3-(4-pyridinyloxy)benzyl]urea

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 2h;96%
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

327-78-6

4-chloro-3-(trifluoromethyl)phenyl isocyanate

284461-73-0

sorafenib

Conditions
ConditionsYield
With zirconia grinding balls In acetonitrile for 4h; Milling;96%
In ethyl acetate at 20 - 30℃; Large scale;94.2%
In dichloromethane93%
284462-37-9

4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide

104-15-4

toluene-4-sulfonic acid

327-78-6

4-chloro-3-(trifluoromethyl)phenyl isocyanate

sorafenib tosylate

Conditions
ConditionsYield
Stage #1: 4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide; 4-chloro-3-(trifluoromethyl)phenyl isocyanate In ethyl acetate at 40 - 71℃; for 0.5h;
Stage #2: toluene-4-sulfonic acid In water; ethyl acetate at 71℃; for 0.666667h; Product distribution / selectivity;
96%
Stage #1: 4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide; 4-chloro-3-(trifluoromethyl)phenyl isocyanate In butanone at 20 - 85℃;
Stage #2: toluene-4-sulfonic acid In butanone at 20℃;
88%
Stage #1: 4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide; 4-chloro-3-(trifluoromethyl)phenyl isocyanate In tetrahydrofuran at 25 - 64℃; for 0.5h;
Stage #2: toluene-4-sulfonic acid In tetrahydrofuran at 64℃; Product distribution / selectivity;
81.6%
327-78-6

4-chloro-3-(trifluoromethyl)phenyl isocyanate

502649-25-4

tert-butyl 4-(3-methoxy-4-(1H-pyrazol-4-yl)benzoyl)-3-phenylpiperazine-1-carboxylate

4-tert-butoxycarbonyl-1-[(4-chloro-3-trifluoromethylphenyl)-aminocarbonyl]-2-phenylpiperazine

Conditions
ConditionsYield
In dichloromethane at 20℃;96%
327-78-6

4-chloro-3-(trifluoromethyl)phenyl isocyanate

120737-59-9

3-methyl-piperazine-1-carboxylic acid tert-butyl ester

4-tert-Butoxycarbonyl-1-[(4-chloro-3-trifluoromethylphenyl)-aminocarbonyl]-2-methylpiperazine

Conditions
ConditionsYield
In dichloromethane at 20℃;96%
539-80-0

Tropone

327-78-6

4-chloro-3-(trifluoromethyl)phenyl isocyanate

1,3-bis(4-chloro-3-(trifluoromethyl)phenyl)-3,6-dihydrocyclohepta[d]imidazol-2(1H)-one

Conditions
ConditionsYield
In Triethylene glycol dimethyl ether at 180℃; for 1h;96%
In Triethylene glycol dimethyl ether at 180℃; for 1h;96%
In Triethylene glycol dimethyl ether at 20 - 180℃; for 1h; Sealed tube; Green chemistry;70%
100-01-6

4-nitro-aniline

327-78-6

4-chloro-3-(trifluoromethyl)phenyl isocyanate

370-52-5

1-(4-chloro-3-(trifluoromethyl)phenyl)-3-(4-nitrophenyl)urea

Conditions
ConditionsYield
In dichloromethane at 20℃; for 24h;96%
In dichloromethane at 20℃; for 48h;90%
In dichloromethane at 20℃; for 24h;73%
In tetrahydrofuran at 20℃; for 2h;
1189975-18-5

4-(4-aminophenoxy)-2-pyridine-(N-(methyl-d3))carboxamide

327-78-6

4-chloro-3-(trifluoromethyl)phenyl isocyanate

1130115-44-4

N-(4-chloro-3-(trifluoromethyl)phenyl)-N'-(4-(2-(N-(methyl-d3)aminoformyl)-4-pyridyloxy)phenyl)urea

Conditions
ConditionsYield
In dichloromethane; dimethyl sulfoxide at 20℃; for 0.333333h; Inert atmosphere;95.4%
In dichloromethane; dimethyl sulfoxide at 20℃; for 0.333333h; Inert atmosphere;95.4%
In dichloromethane; dimethyl sulfoxide at 20℃; for 0.166667h; Inert atmosphere; Large scale;95.4%
1474012-29-7

C18H18N2O2S

327-78-6

4-chloro-3-(trifluoromethyl)phenyl isocyanate

1474012-34-4

N-[(+/-)-1-phenylethyl]-{6-[3-(4-chloro-3-(trifluoromethyl)phenyl)urea]naphthalen-2-yl}sulfonamide

Conditions
ConditionsYield
In tetrahydrofuran at 0 - 20℃; for 0.2h; Inert atmosphere;95.4%
757251-59-5

methyl 4‐(4‐aminophenoxy)picolinate

327-78-6

4-chloro-3-(trifluoromethyl)phenyl isocyanate

573673-43-5

methyl 4‐(4‐(3‐(4‐chloro‐3‐(trifluoromethyl)phenyl)ureido)phenoxy)picolinate

Conditions
ConditionsYield
In dichloromethane at 0 - 20℃; Inert atmosphere;95%
In dichloromethane at 0 - 20℃; for 22h;85%
In dichloromethane at 20℃; for 2h;76%
In dichloromethane at 0 - 20℃;5.9 g
123-30-8

4-amino-phenol

327-78-6

4-chloro-3-(trifluoromethyl)phenyl isocyanate

1129683-83-5

4-[ ({[4-chloro-3-(trifluoromethyl)phenyl]amino}carbonyl)amino]phenol

Conditions
ConditionsYield
In acetonitrile at 20℃; for 3h;95%
In acetonitrile95%
In dichloromethane at 20℃; for 16h;94%
757251-39-1

4-(4-amino-3-fluorophenoxy)pyridine-2-carboxylic acid methyl amide

327-78-6

4-chloro-3-(trifluoromethyl)phenyl isocyanate

755037-03-7

regorafenib

Conditions
ConditionsYield
In ethyl acetate at 20℃; for 1.5h;94.5%
In dichloromethane at 0 - 20℃; for 16h; Inert atmosphere;90%
In dichloromethane for 24h;87%

Boc-tryptophan

120-57-0

piperonal

327-78-6

4-chloro-3-(trifluoromethyl)phenyl isocyanate

C27H17ClN3O4F3

Conditions
ConditionsYield
Multistep reaction.;94%

C12H11FN2O

327-78-6

4-chloro-3-(trifluoromethyl)phenyl isocyanate

C20H14ClF4N3O2

Conditions
ConditionsYield
In dichloromethane at 20℃; for 1h;94%
884340-41-4

4-(4-amino-3-(methylthio)phenoxy)-3-nitropyridin-2-amine

327-78-6

4-chloro-3-(trifluoromethyl)phenyl isocyanate

884340-42-5

1-[4-(2-amino-3-nitropyridin-4-yloxy)-2-(methylthio)phenyl]-3-[4-chloro-3-(trifluoromethyl)phenyl]urea

Conditions
ConditionsYield
at 20℃; for 20h; Inert atmosphere;93%

4-(4-aminophenyl)-1H-thieno[3,4-b][1,4]diazepine-2(3H)-one

327-78-6

4-chloro-3-(trifluoromethyl)phenyl isocyanate

1-(4-chloro-3-(trifluoromethyl)phenyl)-3-(4-(2-oxo-2,3-dihydro-1H-thieno[3,4-b][1,4]diazepin-4-yl)-phenyl)urea

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 12h;93%
In tetrahydrofuran at 20℃;93%

N‐(2‐(tritylthio)ethyl)‐4‐(4‐aminophenoxy)picolinamide

327-78-6

4-chloro-3-(trifluoromethyl)phenyl isocyanate

N‐(2‐(tritylthio)ethyl)‐4‐(4‐(3‐(4‐chloro‐3‐(trifluoromethyl)phenyl)ureido)phenoxy)picolinamide

Conditions
ConditionsYield
In dichloromethane at 20℃; for 2h;93%

C37H31N3O2S

327-78-6

4-chloro-3-(trifluoromethyl)phenyl isocyanate

N‐(2‐(tritylthio)ethyl)‐4‐(4‐(3‐(4‐chloro‐3‐(trifluoromethyl)phenyl)ureido)phenoxy)picolinamide

Conditions
ConditionsYield
In dichloromethane at 20℃; for 2h; Cooling with ice;93%
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Chemistry

IUPAC Name: 1-Chloro-4-isocyanato-2-(trifluoromethyl)benzene 
Following is the structure of 4-Chloro-3-(trifluoromethyl)phenyl isocyanate (CAS NO.327-78-6):
                           
Empirical Formula: C8H3ClF3NO
Molecular Weight: 221.5637 
Index of Refraction: 1.487
Molar Refractivity: 45.51 cm3
Molar Volume: 158.2 cm3  
Density: 1.4 g/cm3
Flash Point: 84.9 °C
Melting point: 40-42 °C(lit.)
Sensitive: Moisture Sensitive
Surface Tension: 32.5 dyne/cm
Enthalpy of Vaporization: 43.79 kJ/mol
Boiling Point: 201.7 °C at 760 mmHg
Vapour Pressure: 0.304 mmHg at 25°C 
Product Categories of 4-Chloro-3-(trifluoromethyl)phenyl isocyanate (CAS NO.327-78-6): Phenyl isocyanate & Phenyl isothiocyanate; Isocyanates; Nitrogen Compounds; Organic Building Blocks
Appearance of 4-Chloro-3-(trifluoromethyl)phenyl isocyanate (CAS NO.327-78-6): White solid or melt
Canonical SMILES: C1=CC(=C(C=C1N=C=O)C(F)(F)F)Cl
InChI: InChI=1S/C8H3ClF3NO/c9-7-2-1-5(13-4-14)3-6(7)8(10,11)12/h1-3H
InChIKey: NBJZEUQTGLSUOB-UHFFFAOYSA-N

Toxicity Data With Reference

 4-Chloro-3-(trifluoromethyl)phenyl isocyanate (CAS NO.327-78-6) hasn't been listed as a carcinogen by ACGIH, IARC, NTP, or CA Prop 65. And the toxicological properties have not been fully investigated.

Safety Profile

Hazard Codes: HarmfulXn
Risk Statements: 20/21/22-36/37-36/37/38-42-20/22 
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed. 
R36/37:Irritating to eyes and respiratory system. 
R36/37/38:Irritating to eyes, respiratory system and skin. 
R42:May cause sensitization by inhalation. 
R20/22:Harmful by inhalation and if swallowed.
Safety Statements: 7-26-27-37/39-36/37/39-45-23 
S7:Keep container tightly closed. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S27:Take off immediately all contaminated clothing. 
S37/39:Wear suitable gloves and eye/face protection. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S23:Do not breathe vapour.
RIDADR: UN 2206 6.1/PG 3
WGK Germany: 3
Hazard Note: Harmful/Moisture Sensitive
HazardClass: 6.1
PackingGroup: III

Specification

 4-Chloro-3-(trifluoromethyl)phenyl isocyanate , its cas register number is 327-78-6. It also can be called Benzene, 1-chloro-4-isocyanato-2-(trifluoromethyl)- .
 4-Chloro-3-(trifluoromethyl)phenyl isocyanate (CAS NO.327-78-6) should avoid the condition like incompatible materials,  exposure to moist air or water. It is not compatible with strong oxidizing agents. And also prevent it to broken down into hazardous decomposition products: hydrogen chloride, nitrogen oxides, carbon monoxide, carbon dioxide, hydrogen fluoride gas. However, its hazardous polymerization has not been reported.