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103-71-9

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103-71-9 Usage

Chemical Description

Different sources of media describe the Chemical Description of 103-71-9 differently. You can refer to the following data:
1. Phenyl isocyanate is an organic compound with the formula C6H5NCO.
2. Phenyl isocyanate is an organic compound with the chemical formula C7H5NO.
3. Phenyl isocyanate is an organic compound with the formula C6H5NCO, used in the synthesis of various chemicals.
4. Phenyl isocyanate is a colorless liquid used in the production of urethane foams.

Chemical Properties

Different sources of media describe the Chemical Properties of 103-71-9 differently. You can refer to the following data:
1. colourless to light yellow liquid with an acrid odour
2. Phenyl isocyanate is a colorless liquid with an irritating odor.

Uses

Different sources of media describe the Uses of 103-71-9 differently. You can refer to the following data:
1. Phenyl Isocyanate is also used in the synthesis of cyanopyridine derivatives in the search for anticancer compounds. It is also used in the synthesis of aminobenzimidazole derivatives with phenylcyclohexyl acetic groups showing antiobesity-antidiabetic activity.
2. Phenyl isocyanate was used to prepare chemically modified cellulose paper. It was used in the synthesis of functionalized graphene oxide nanoplatelets.

Preparation

To a mixture of aniline hydrochloride (12.95 g, 0.1 mol) and dry dioxane (100 mL) was added diphosgene (6.3 mL, 10.4 g, 0.05 mol). The mixture was heated to 60 °C; after stirring for 1.5 h, it became a clear solution. Heating was stopped after 3.5 h and the solvent was removed under reduced pressure. The residue was distilled at 70–73.5 °C (36 mmHg) to give 10.6 g (89%) of phenyl isocyanate. It could be redistilled almost quantitatively, bp 75–77 °C(39 mmHg) or 55–57 °C(16 mmHg).

Definition

ChEBI: An isocyanate composed of a benzene ring bearing a single isocyanato substituent.

Synthesis Reference(s)

Journal of the American Chemical Society, 90, p. 3295, 1968 DOI: 10.1021/ja01014a089

General Description

A colorless liquid. About the same density as water. Very toxic by ingestion, inhalation or skin absorption. Very irritating to skin, eyes and mucous membranes. Flash point 132°F.

Air & Water Reactions

Flammable. Decomposes in water.

Reactivity Profile

Isocyanates and thioisocyanates, such as Phenyl isocyanate, are incompatible with many classes of compounds, reacting exothermically to release toxic gases. Reactions with amines, aldehydes, alcohols, alkali metals, ketones, mercaptans, strong oxidizers, hydrides, phenols, and peroxides can cause vigorous releases of heat. Acids and bases initiate polymerization reactions in these materials. Some isocyanates react with water to form amines and liberate carbon dioxide. Polyurethanes are formed by the condensation reaction of diisocyanates with, for example, ethyl glycol. Phenyl isocyanate, cobalt pentamine triazo perchlorate, and nitrosyl perchlorate mixture was stirred for 2-3 minutes. When the stirring was interrupted, the mixture exploded [Chem. Eng. News 46(8):39. 1968].

Health Hazard

TOXIC; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death. Bromoacetates and chloroacetates are extremely irritating/lachrymators. Reaction with water or moist air will release toxic, corrosive or flammable gases. Reaction with water may generate much heat that will increase the concentration of fumes in the air. Fire will produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.

Fire Hazard

HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapors may travel to source of ignition and flash back. Substance will react with water (some violently) releasing flammable, toxic or corrosive gases and runoff. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated or if contaminated with water.

Safety Profile

A poison. An irritant. Mutation data reported. Flammable liquid when exposed to heat or flame; can react vigorously with oxidizing materials. Has exploded when stirred with (cobalt pentammine triazoperchlorate + nitrosyl perchlorate). When heated to decomposition it emits toxic fumes of CNand NOx. See also CYANATES.

Potential Exposure

Phenyl isocyanate is used as a laboratory reagent and in organic synthesis

Shipping

UN2487 Phenyl isocyanate, Hazard class: 6.1; Labels: 6.1-Poisonous materials, 3-Flammable liquid

Purification Methods

Distil phenylisocyanate under reduced pressure from P2O5. [Beilstein 12 IV 864.]

Incompatibilities

May form explosive mixture with air. Isocyanates are highly flammable and reactive with many compounds, even with themselves. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Reaction with moist air, water or alcohols may form amines and insoluble polyureas and react exothermically, releasing toxic, corrosive or flammable gases, including carbon dioxide; and, at the same time, may generate a violent release of heat increasing the concentration of fumes in the air. Incompatible with amines, aldehydes, alkali metals, ammonia, carboxylic acids, caprolactum, alkaline materials, glycols, ketones, mercaptans, hydrides, organotin catalysts, phenols, strong acids, strong bases, strong reducing agents, urethanes, ureas. Elevated temperatures or contact with acids, bases, tertiary amines, and acyl-chlorides may cause explosive polymerization. Contact with metals may evolve flammable hydrogen gas. Attacks some plastics, rubber and coatings. Contact with metals may evolve flammable hydrogen gas. May accumulate static electrical charges, and may cause ignition of its vapors.

Check Digit Verification of cas no

The CAS Registry Mumber 103-71-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 3 respectively; the second part has 2 digits, 7 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 103-71:
(5*1)+(4*0)+(3*3)+(2*7)+(1*1)=29
29 % 10 = 9
So 103-71-9 is a valid CAS Registry Number.
InChI:InChI=1/C7H5NO/c9-6-8-7-4-2-1-3-5-7/h1-5H

103-71-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name phenyl isocyanate

1.2 Other means of identification

Product number -
Other names Fenylisokyanat

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Intermediates
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:103-71-9 SDS

103-71-9Synthetic route

benzoyl azide
582-61-6

benzoyl azide

phenyl isocyanate
103-71-9

phenyl isocyanate

Conditions
ConditionsYield
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%
bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

aniline
62-53-3

aniline

phenyl isocyanate
103-71-9

phenyl isocyanate

Conditions
ConditionsYield
With triethylamine In dichloromethane100%
In ethyl acetate at 0 - 5℃; for 3h; Solvent; Cooling with ice; Reflux;89%
In chloroform at 20℃; for 1h; Cooling with ice;85%
N-carboethoxyaniline
101-99-5

N-carboethoxyaniline

phenyl isocyanate
103-71-9

phenyl isocyanate

Conditions
ConditionsYield
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
18100-80-6

2,3,5-triphenyl-4-thiazolone

dimethyl acetylenedicarboxylate
762-42-5

dimethyl acetylenedicarboxylate

A

dimethyl 2,5-diphenylthiophene-3,4-dicarboxylate
20851-13-2

dimethyl 2,5-diphenylthiophene-3,4-dicarboxylate

B

phenyl isocyanate
103-71-9

phenyl isocyanate

Conditions
ConditionsYield
In xylene Heating;A 99%
B n/a
phosgene
75-44-5

phosgene

aniline
62-53-3

aniline

phenyl isocyanate
103-71-9

phenyl isocyanate

Conditions
ConditionsYield
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
66702-57-6

2-dimethylamino-5-(4-nitro-phenyl)-4-oxo-3-phenyl-4,5-dihydro-thiazolium betaine

dimethyl acetylenedicarboxylate
762-42-5

dimethyl acetylenedicarboxylate

A

phenyl isocyanate
103-71-9

phenyl isocyanate

B

2-Dimethylamino-5-(4-nitro-phenyl)-thiophene-3,4-dicarboxylic acid dimethyl ester
85013-66-7

2-Dimethylamino-5-(4-nitro-phenyl)-thiophene-3,4-dicarboxylic acid dimethyl ester

Conditions
ConditionsYield
In xylene Heating;A n/a
B 98%
2-cyano-5-(4-nitro-phenyl)-4-oxo-3-phenyl-4,5-dihydro-thiazolium betaine
66702-60-1

2-cyano-5-(4-nitro-phenyl)-4-oxo-3-phenyl-4,5-dihydro-thiazolium betaine

dimethyl acetylenedicarboxylate
762-42-5

dimethyl acetylenedicarboxylate

A

phenyl isocyanate
103-71-9

phenyl isocyanate

B

2-Cyano-5-(4-nitro-phenyl)-thiophene-3,4-dicarboxylic acid dimethyl ester
85013-63-4

2-Cyano-5-(4-nitro-phenyl)-thiophene-3,4-dicarboxylic acid dimethyl ester

Conditions
ConditionsYield
In xylene Heating;A n/a
B 98%
5-(4-nitro-phenyl)-4-oxo-2,3-diphenyl-4,5-dihydro-thiazolium betaine
59208-07-0

5-(4-nitro-phenyl)-4-oxo-2,3-diphenyl-4,5-dihydro-thiazolium betaine

dimethyl acetylenedicarboxylate
762-42-5

dimethyl acetylenedicarboxylate

A

phenyl isocyanate
103-71-9

phenyl isocyanate

B

2-(4-Nitro-phenyl)-5-phenyl-thiophene-3,4-dicarboxylic acid dimethyl ester
59086-14-5

2-(4-Nitro-phenyl)-5-phenyl-thiophene-3,4-dicarboxylic acid dimethyl ester

Conditions
ConditionsYield
In xylene Heating;A n/a
B 97%
phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

phenyl isocyanate
103-71-9

phenyl isocyanate

Conditions
ConditionsYield
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
carbamic acid phenyl ester
622-46-8

carbamic acid phenyl ester

phenyl isocyanate
103-71-9

phenyl isocyanate

Conditions
ConditionsYield
In chlorobenzene at 160 - 240℃; under 11251.1 Torr; for 1h; Pressure; Solvent; Temperature; Inert atmosphere; Green chemistry;94.9%
5-(4-nitro-phenyl)-4-oxo-3-phenyl-2-phenylsulfanyl-4,5-dihydro-thiazolium betaine
66702-58-7

5-(4-nitro-phenyl)-4-oxo-3-phenyl-2-phenylsulfanyl-4,5-dihydro-thiazolium betaine

dimethyl acetylenedicarboxylate
762-42-5

dimethyl acetylenedicarboxylate

A

phenyl isocyanate
103-71-9

phenyl isocyanate

B

2-(4-Nitro-phenyl)-5-phenylsulfanyl-thiophene-3,4-dicarboxylic acid dimethyl ester
85013-62-3

2-(4-Nitro-phenyl)-5-phenylsulfanyl-thiophene-3,4-dicarboxylic acid dimethyl ester

Conditions
ConditionsYield
In xylene Heating;A n/a
B 94%
5-benzyl-3,4-dihydro-4-oxo-1,2,3-triphenylpyrimidin-1-ium-6-olate
56409-80-4

5-benzyl-3,4-dihydro-4-oxo-1,2,3-triphenylpyrimidin-1-ium-6-olate

4-methoxyphenyl cyanate
2983-74-6

4-methoxyphenyl cyanate

A

phenyl isocyanate
103-71-9

phenyl isocyanate

B

5-Benzyl-6-(4-methoxy-phenoxy)-2,3-diphenyl-3H-pyrimidin-4-one
85037-41-8

5-Benzyl-6-(4-methoxy-phenoxy)-2,3-diphenyl-3H-pyrimidin-4-one

C

2,4,6-tris(4-methoxyphenoxy)-1,3,5-triazine
25940-64-1

2,4,6-tris(4-methoxyphenoxy)-1,3,5-triazine

Conditions
ConditionsYield
In chlorobenzene for 29h; Heating;A n/a
B 93%
C n/a
3,3-Dimethyl-1-phenyl-2-azetidinone
27983-93-3

3,3-Dimethyl-1-phenyl-2-azetidinone

A

phenyl isocyanate
103-71-9

phenyl isocyanate

B

isobutene
115-11-7

isobutene

Conditions
ConditionsYield
at 750℃; under 0.002 Torr;A 93%
B n/a
benzaldehyde
100-52-7

benzaldehyde

phenyl isocyanate
103-71-9

phenyl isocyanate

Conditions
ConditionsYield
In chloroform at 60℃; for 18h;92%
5-benzyl-3,4-dihydro-4-oxo-1,2,3-triphenylpyrimidin-1-ium-6-olate
56409-80-4

5-benzyl-3,4-dihydro-4-oxo-1,2,3-triphenylpyrimidin-1-ium-6-olate

phenyl cyanate
1122-85-6

phenyl cyanate

A

2,4,6-triphenoxy-1,3,5-triazine
1919-48-8

2,4,6-triphenoxy-1,3,5-triazine

B

phenyl isocyanate
103-71-9

phenyl isocyanate

C

5-Benzyl-6-phenoxy-2,3-diphenyl-3H-pyrimidin-4-one
85037-39-4

5-Benzyl-6-phenoxy-2,3-diphenyl-3H-pyrimidin-4-one

Conditions
ConditionsYield
In chlorobenzene for 18h; Heating;A n/a
B n/a
C 92%
2-cyano-4-oxo-3,5-diphenyl-4,5-dihydro-thiazolium betaine
61522-23-4

2-cyano-4-oxo-3,5-diphenyl-4,5-dihydro-thiazolium betaine

dimethyl acetylenedicarboxylate
762-42-5

dimethyl acetylenedicarboxylate

A

phenyl isocyanate
103-71-9

phenyl isocyanate

B

2-Cyano-5-phenyl-thiophene-3,4-dicarboxylic acid dimethyl ester
85013-64-5

2-Cyano-5-phenyl-thiophene-3,4-dicarboxylic acid dimethyl ester

Conditions
ConditionsYield
In xylene Heating;A n/a
B 92%
4-Methyl-3,5-dioxo-2,6-diphenyl-2,6-diazabicyclo<2.2.2>oct-7-en-7-carbonsaeure-methylester

4-Methyl-3,5-dioxo-2,6-diphenyl-2,6-diazabicyclo<2.2.2>oct-7-en-7-carbonsaeure-methylester

A

phenyl isocyanate
103-71-9

phenyl isocyanate

B

1,2-Dihydro-3-methyl-2-oxo-1-phenyl-5-pyridincarbonsaeure-methylester

1,2-Dihydro-3-methyl-2-oxo-1-phenyl-5-pyridincarbonsaeure-methylester

Conditions
ConditionsYield
at 220℃; for 0.166667h;A n/a
B 92%
4-Benzyl-7,8-bis(diethylamino)-2,6-diphenyl-2,6-diazabicyclo<2.2.2>oct-7-en-3,5-dion

4-Benzyl-7,8-bis(diethylamino)-2,6-diphenyl-2,6-diazabicyclo<2.2.2>oct-7-en-3,5-dion

A

phenyl isocyanate
103-71-9

phenyl isocyanate

B

3-Benzyl-4,5-bis(diethylamino)-1-phenyl-2(1H)-pyridinon

3-Benzyl-4,5-bis(diethylamino)-1-phenyl-2(1H)-pyridinon

Conditions
ConditionsYield
at 150℃; for 0.166667h;A n/a
B 92%
N-phenyl methyl carbamate
2603-10-3

N-phenyl methyl carbamate

phenyl isocyanate
103-71-9

phenyl isocyanate

Conditions
ConditionsYield
With Phenyltrichlorosilane at 85 - 184℃; for 1h;90.8%
With phosphorus pentachloride at 120 - 140℃; for 3h;68%
With boron trichloride; triethylamine In benzene for 0.5h; Heating;93 % Chromat.
carbon monoxide
201230-82-2

carbon monoxide

nitrobenzene
98-95-3

nitrobenzene

phenyl isocyanate
103-71-9

phenyl isocyanate

Conditions
ConditionsYield
With pyridine; di(rhodium)tetracarbonyl dichloride; pyridine hydrochloride In chlorobenzene at 205℃; under 50 Torr; for 1h;90%
With di(rhodium)tetracarbonyl dichloride; pyridine hydrochloride In chlorobenzene at 190℃; under 38000 Torr; for 1h;80%
Stage #1: nitrobenzene at 120℃; under 75007.5 Torr; for 4h; Inert atmosphere; Autoclave;
Stage #2: carbon monoxide Catalytic behavior; Temperature; Reagent/catalyst; Inert atmosphere; Autoclave;
72.2%
C16H16N4OS2
109853-15-8

C16H16N4OS2

A

phenyl isocyanate
103-71-9

phenyl isocyanate

B

3-Mercapto-1-methyl-5-phenyl-1,2,4-triazol
13281-49-7

3-Mercapto-1-methyl-5-phenyl-1,2,4-triazol

Conditions
ConditionsYield
N-benzyl-N,N,N-triethylammonium chloride In sodium hydroxide; dichloromethane for 12h; Ambient temperature;A n/a
B 89%
bis(trimethylsilyl)benzohydroxamic acid
77219-88-6

bis(trimethylsilyl)benzohydroxamic acid

A

Hexamethyldisiloxane
107-46-0

Hexamethyldisiloxane

B

phenyl isocyanate
103-71-9

phenyl isocyanate

Conditions
ConditionsYield
at 120℃;A n/a
B 88%
N-(2,2-dimethyl-3-butynoyl)-N,N'-diphenylurea

N-(2,2-dimethyl-3-butynoyl)-N,N'-diphenylurea

A

phenyl isocyanate
103-71-9

phenyl isocyanate

B

2,2-dimethyl-N-phenyl-3-butynamide

2,2-dimethyl-N-phenyl-3-butynamide

Conditions
ConditionsYield
In benzene for 2h; Heating;A n/a
B 88%
1-phenylazetidin-2-one
5099-95-6

1-phenylazetidin-2-one

A

ethene
74-85-1

ethene

B

phenyl isocyanate
103-71-9

phenyl isocyanate

Conditions
ConditionsYield
at 750℃; under 0.002 Torr; Mechanism; regioselectivity, other substituted 1-phenylazetidin-2-ones, var. temp.;A n/a
B 88%
at 750℃; under 0.002 Torr;A n/a
B 88%
di-tert-butyl tricarbonate
24424-95-1

di-tert-butyl tricarbonate

aniline
62-53-3

aniline

phenyl isocyanate
103-71-9

phenyl isocyanate

Conditions
ConditionsYield
In dichloromethane for 0.0833333h; Ambient temperature;87%
Benzohydroxamic acid
495-18-1

Benzohydroxamic acid

phenyl isocyanate
103-71-9

phenyl isocyanate

Conditions
ConditionsYield
With Phenyltrichlorosilane at 55 - 197℃; for 2h;86%
With Phenyltrichlorosilane at 55 - 197℃; for 2h; Product distribution; var. silanes, var. time, var. temp.;86%
With Phenyltrichlorosilane at 100 - 130℃; for 2h;81.9%
N-Benzoyl-N,O-bis(trimethylsilyl)hydroxylamine
67723-48-2

N-Benzoyl-N,O-bis(trimethylsilyl)hydroxylamine

A

N-phenyl-N'-benzoylurea
1821-33-6

N-phenyl-N'-benzoylurea

B

phenyl isocyanate
103-71-9

phenyl isocyanate

Conditions
ConditionsYield
In decalin at 160℃; for 0.0833333h;A 5.7%
B 86%
acid sodium salt of benzohydroxamic acid
22513-32-2

acid sodium salt of benzohydroxamic acid

phenyl isocyanate
103-71-9

phenyl isocyanate

Conditions
ConditionsYield
With Phenyltrichlorosilane at 130 - 140℃; for 2h;86%
With Phenyltrichlorosilane at 130 - 140℃; for 2h;85.8%
4-Methyl-3,5-dioxo-2,6-diphenyl-2,6-diazabicyclo<2.2.2>oct-7-en-7,8-dicarbonsaeure-dimethylester

4-Methyl-3,5-dioxo-2,6-diphenyl-2,6-diazabicyclo<2.2.2>oct-7-en-7,8-dicarbonsaeure-dimethylester

A

phenyl isocyanate
103-71-9

phenyl isocyanate

B

1,2-Dihydro-3-methyl-2-oxo-1-phenyl-4,5-pyridindicarbonsaeure-dimethylester

1,2-Dihydro-3-methyl-2-oxo-1-phenyl-4,5-pyridindicarbonsaeure-dimethylester

Conditions
ConditionsYield
at 220℃; for 0.166667h;A n/a
B 85%
morpholine
110-91-8

morpholine

phenyl isocyanate
103-71-9

phenyl isocyanate

N-phenylmorpholine-4-carboxamide
4559-92-6

N-phenylmorpholine-4-carboxamide

Conditions
ConditionsYield
at 0 - 20℃; for 48.3333h;100%
In diethyl ether at 20℃; for 18h;99.2%
In diethyl ether at 20℃; for 0.75h; Addition;97%
1H-imidazole
288-32-4

1H-imidazole

phenyl isocyanate
103-71-9

phenyl isocyanate

N-phenyl-1H-imidazole-1-carboxamide
33876-94-7

N-phenyl-1H-imidazole-1-carboxamide

Conditions
ConditionsYield
In dichloromethane at 20℃; for 1h;100%
In 1,4-dioxane at 0 - 20℃;87%
In diethyl ether for 3h; Heating;84%
tryptamine
61-54-1

tryptamine

phenyl isocyanate
103-71-9

phenyl isocyanate

N-[2-(1H-indol-3-yl)ethyl]-N'-phenylurea
32585-51-6

N-[2-(1H-indol-3-yl)ethyl]-N'-phenylurea

Conditions
ConditionsYield
Stage #1: tryptamine; phenyl isocyanate In dichloromethane at 60℃;
Stage #2: With isatoic anhydride-N-(CH2)3-C8F17 In dichloromethane at 60℃; for 2.5h;
100%
In dichloromethane at 60℃; for 5h; Inert atmosphere; Sealed reaction vessel;98%
1-(2-pyridyl)piperazine
34803-66-2

1-(2-pyridyl)piperazine

phenyl isocyanate
103-71-9

phenyl isocyanate

4-[2]pyridyl-piperazine-1-carboxylic acid anilide

4-[2]pyridyl-piperazine-1-carboxylic acid anilide

Conditions
ConditionsYield
Stage #1: 1-(2-pyridyl)piperazine; phenyl isocyanate In dichloromethane at 60℃;
Stage #2: With isatoic anhydride-N-(CH2)3-C8F17 In dichloromethane at 60℃; for 2.5h;
100%
methanol
67-56-1

methanol

phenyl isocyanate
103-71-9

phenyl isocyanate

N-phenyl methyl carbamate
2603-10-3

N-phenyl methyl carbamate

Conditions
ConditionsYield
With cerium(IV) oxide; carbon dioxide at 170℃; under 30003 Torr; for 12h; Inert atmosphere; Autoclave;100%
With dibutyltin dilaurate at 50℃; for 3h;100%
at 80℃; for 0.5h; Inert atmosphere;98%
phenyl isocyanate
103-71-9

phenyl isocyanate

3-methyl-2-buten-1-ol
556-82-1

3-methyl-2-buten-1-ol

3-methylbut-2-en-1-yl phenylcarbamate
105902-61-2

3-methylbut-2-en-1-yl phenylcarbamate

Conditions
ConditionsYield
In acetonitrile at 70℃; for 23h; Inert atmosphere;100%
With triethylamine In dichloromethane at 20℃; Inert atmosphere;88%
With triethylamine In dichloromethane at 20℃;88%
(-)-menthol
2216-51-5

(-)-menthol

phenyl isocyanate
103-71-9

phenyl isocyanate

phenylcarbamic acid (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl ester
637336-84-6

phenylcarbamic acid (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl ester

Conditions
ConditionsYield
With MoCl2O2(dmf)2 In dichloromethane at 20℃; for 0.333333h;100%
With MoCl2O2(dmf)2 In dichloromethane at 20℃; for 0.333333h; Reagent/catalyst; Inert atmosphere; Sealed tube;100%
phenyl isocyanate
103-71-9

phenyl isocyanate

propargyl alcohol
107-19-7

propargyl alcohol

2-propynyl phenylcarbamate
5416-67-1

2-propynyl phenylcarbamate

Conditions
ConditionsYield
With dmap; triethylamine In tetrahydrofuran at 20℃; for 90h;100%
With MoCl2O2(dmf)2 In dichloromethane at 20℃; for 0.333333h;100%
With MoCl2O2(dmf)2 In dichloromethane at 20℃; for 0.333333h; Inert atmosphere; Sealed tube;100%
phenyl isocyanate
103-71-9

phenyl isocyanate

N-butylamine
109-73-9

N-butylamine

N-butyl-N'-phenylurea
3083-88-3

N-butyl-N'-phenylurea

Conditions
ConditionsYield
Stage #1: phenyl isocyanate; N-butylamine In dichloromethane at 60℃;
Stage #2: With isatoic anhydride-N-(CH2)3-C8F17 In dichloromethane at 60℃; for 2.5h;
100%
at 20℃;98%
In hexane at 25℃; Cooling with ice;98%
phenyl isocyanate
103-71-9

phenyl isocyanate

aniline
62-53-3

aniline

bis(diphenyl)urea
102-07-8

bis(diphenyl)urea

Conditions
ConditionsYield
With triethylamine In dichloromethane100%
In acetic acid for 0.0833333h;98%
In hexane95%
phenyl isocyanate
103-71-9

phenyl isocyanate

4-Ethoxyaniline
156-43-4

4-Ethoxyaniline

1-(4-ethoxy-phenyl)-3-phenyl urea
4345-85-1

1-(4-ethoxy-phenyl)-3-phenyl urea

Conditions
ConditionsYield
In tetrahydrofuran for 0.166667h;100%
With diethyl ether
phenyl isocyanate
103-71-9

phenyl isocyanate

2-methyl-but-3-yn-2-ol
115-19-5

2-methyl-but-3-yn-2-ol

O-α,α-dimethylpropargyl N-phenylcarbamate
6289-19-6

O-α,α-dimethylpropargyl N-phenylcarbamate

Conditions
ConditionsYield
With MoCl2O2(dmf)2 In dichloromethane at 20℃; for 0.333333h;100%
With triethylamine In tetrahydrofuran at 70℃; for 12h; Inert atmosphere;94%
With dmap; triethylamine In tetrahydrofuran at 20℃; for 90h;88%
phenyl isocyanate
103-71-9

phenyl isocyanate

para-methylbenzylamine
104-84-7

para-methylbenzylamine

N-(4-methylbenzyl)-N’-phenylurea
35305-46-5

N-(4-methylbenzyl)-N’-phenylurea

Conditions
ConditionsYield
Stage #1: phenyl isocyanate; para-methylbenzylamine In dichloromethane at 60℃;
Stage #2: With isatoic anhydride-N-(CH2)3-C8F17 In dichloromethane at 60℃; for 2.5h;
100%
phenyl isocyanate
103-71-9

phenyl isocyanate

butan-1-ol
71-36-3

butan-1-ol

N-phenyl-carbamic acid butyl ester
1538-74-5

N-phenyl-carbamic acid butyl ester

Conditions
ConditionsYield
chlorodi-(n-butyl)tin acetate In chloroform for 0.833333h; Product distribution; Mechanism; Ambient temperature; catalytic activity, various tin(IV) catalysts;100%
chlorodi-(n-butyl)tin acetate In chloroform for 0.833333h; Ambient temperature;100%
With diallyltin(IV)di(2-ethyl hexanoate) In dichloromethane for 0.0833333h; Product distribution; Heating; other alcohols and isocyanates; var. temp. and time;93%
phenyl isocyanate
103-71-9

phenyl isocyanate

phenol
108-95-2

phenol

phenyl N-phenylcarbamate
4930-03-4

phenyl N-phenylcarbamate

Conditions
ConditionsYield
at 20℃; for 2h;100%
With cesium fluoride93.1%
With triethylamine In acetonitrile for 24.5h; Esterification;89%
phenyl isocyanate
103-71-9

phenyl isocyanate

triphenyl isocyanurate
1785-02-0

triphenyl isocyanurate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 70℃; under 6000480 Torr; for 20h;100%
With sodium nitrite for 0.166667h; Cyclization; microwave irradiation;99%
With 1,3-bis(2,6-diisopropylphenyl)dihydroimidazol-2-ylidene In tetrahydrofuran at 20℃; for 1h;99%
1-methyl-1-benzoylhydrazine
1483-24-5

1-methyl-1-benzoylhydrazine

phenyl isocyanate
103-71-9

phenyl isocyanate

1-Benzoyl-1-methyl-4-phenylsemicarbazid
13136-26-0

1-Benzoyl-1-methyl-4-phenylsemicarbazid

Conditions
ConditionsYield
In tetrahydrofuran Heating;100%
In diethyl ether
In ethanol
phenyl isocyanate
103-71-9

phenyl isocyanate

1-Ethynyl-1-cyclohexanol
78-27-3

1-Ethynyl-1-cyclohexanol

1-ethynylcyclohexyl phenylcarbamate
73623-16-2

1-ethynylcyclohexyl phenylcarbamate

Conditions
ConditionsYield
With dmap; triethylamine In tetrahydrofuran at 20℃; for 90h;100%
In 1,2-dichloro-ethane at 20℃; for 16h;82%
With 1-methyl-pyrrolidin-2-one
phenyl isocyanate
103-71-9

phenyl isocyanate

1-Ethynylcyclohexylamine
30389-18-5

1-Ethynylcyclohexylamine

1-(1-ethynylcyclohexyl)-3-phenylurea
42785-83-1

1-(1-ethynylcyclohexyl)-3-phenylurea

Conditions
ConditionsYield
In tetrahydrofuran at 20℃;100%
In diethyl ether
phenyl isocyanate
103-71-9

phenyl isocyanate

2,2'-iminobis[ethanol]
111-42-2

2,2'-iminobis[ethanol]

1,1-[Di-(2-hydroxyethyl)]-3-phenylurea
20074-78-6

1,1-[Di-(2-hydroxyethyl)]-3-phenylurea

Conditions
ConditionsYield
In dichloromethane100%
In benzene
In dichloromethane; toluene at 20℃;
In dichloromethane at 20℃; for 0.0166667h; Inert atmosphere;1.14 g
(+/-)-2-methyloxetane
2167-39-7

(+/-)-2-methyloxetane

phenyl isocyanate
103-71-9

phenyl isocyanate

6-methyl-3-phenyl-1,3-oxazinan-2-one
99855-05-7

6-methyl-3-phenyl-1,3-oxazinan-2-one

Conditions
ConditionsYield
With N,N,N,N,N,N-hexamethylphosphoric triamide; diphenyltin diiodide at 80℃; for 3h; sealed tube;100%
With tetraphenyl stibonium iodide In tetrahydrofuran at 60℃; for 23h;27%
ethyloxirane
106-88-7

ethyloxirane

phenyl isocyanate
103-71-9

phenyl isocyanate

4-ethyl-3-phenyl-1,3-oxazolidine-2-one
105873-71-0

4-ethyl-3-phenyl-1,3-oxazolidine-2-one

Conditions
ConditionsYield
With tetraphenyl stibonium iodide In dichloromethane at 40℃;100%
tetraphenyl stibonium iodide In dichloromethane at 45℃; for 1h;100%
tetraphenyl stibonium iodide In dichloromethane at 45℃; for 1h; Heating;84%
propan-1-ol
71-23-8

propan-1-ol

phenyl isocyanate
103-71-9

phenyl isocyanate

1-propyl (4-methylphenyl)carbamate
63379-16-8

1-propyl (4-methylphenyl)carbamate

Conditions
ConditionsYield
In pyridine; ethyl acetate100%
hycanthone
3105-97-3

hycanthone

phenyl isocyanate
103-71-9

phenyl isocyanate

hycanthone N-phenylcarbamate
3612-74-6

hycanthone N-phenylcarbamate

Conditions
ConditionsYield
In dichloromethane100%
1-methyl-6-methylsulfanyl-1,2,3,4-tetrahydro-pyridine
25355-53-7

1-methyl-6-methylsulfanyl-1,2,3,4-tetrahydro-pyridine

phenyl isocyanate
103-71-9

phenyl isocyanate

1-Methyl-2-methylsulfanyl-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid phenylamide
81197-49-1

1-Methyl-2-methylsulfanyl-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid phenylamide

Conditions
ConditionsYield
In diethyl ether Ambient temperature;100%
In diethyl ether for 4h; Ambient temperature; Yield given;
pentan-1-ol
71-41-0

pentan-1-ol

phenyl isocyanate
103-71-9

phenyl isocyanate

pentyl N-phenyl-carbamate
63075-06-9

pentyl N-phenyl-carbamate

Conditions
ConditionsYield
for 1h;100%
for 1h; Heating;100%
at 20℃;92%
2-(trimethylsilyloxy)ethanamine
5804-92-2

2-(trimethylsilyloxy)ethanamine

phenyl isocyanate
103-71-9

phenyl isocyanate

1-phenyl-3-<2-(trimethylsiloxy)ethyl>urea

1-phenyl-3-<2-(trimethylsiloxy)ethyl>urea

Conditions
ConditionsYield
100%
Methyl 3-mercaptopropionate
2935-90-2

Methyl 3-mercaptopropionate

phenyl isocyanate
103-71-9

phenyl isocyanate

3-(N-Phenylcarbamoylmercapto)-propionsaeuremethylester
77585-81-0

3-(N-Phenylcarbamoylmercapto)-propionsaeuremethylester

Conditions
ConditionsYield
With N-benzyl-trimethylammonium hydroxide In diethyl ether at 40℃; for 0.5h;100%
1-benzoyl-2-methylhydrazine
1660-24-8

1-benzoyl-2-methylhydrazine

phenyl isocyanate
103-71-9

phenyl isocyanate

1-Benzoyl-2-methyl-4-phenylsemicarbazid
77919-29-0

1-Benzoyl-2-methyl-4-phenylsemicarbazid

Conditions
ConditionsYield
In tetrahydrofuran Heating;100%

103-71-9Relevant articles and documents

-

Hoshino et al.

, p. 3097 (1952)

-

CARBONYLATION OF NITROBENZENE WITH RUTHENIUM CLUSTERS

Basu, Amitabha,Bhaduri, Sumit,Khwaja, Hanif

, p. C28 - C30 (1987)

Evidence is presented for the participation of cluster intermediates in the carbonylation of nitrobenzene.

-

Kurita,K. et al.

, p. 2070 - 2071 (1976)

-

Preferred Binding of Carboxylates by Chiral Urea Derivatives Containing α-Phenylethyl Group

Cortés-Hernández, Mayra,Rojas-Lima, Susana,Hernández-Rodríguez, Marcos,Cruz-Borbolla, Julián,López-Ruiz, Heraclio

, p. 416 - 424 (2016)

An efficient, simple protocol for the synthesis of a new family of chiral ureas 1 – 4 is described. The binding properties of 1 – 4 toward different anion (acetate, benzoate, fluoride, and chloride) have been studied by1H-NMR titration and have been observed in the case of 4 is a selective receptor for acetate. The theoretical calculation M06/6-311+G(d,p) helped us explain the binding properties observed. The most interesting observation is that this calculated structure is consistent with expected, based on the concept of allylic 1,3-strain (A1,3strain). When chiral caboxylates were studied, urea 1 was the best in discriminating between enantiomers.

SYNTHESIS OF ISOCYANATES BY THE CARBONYLATION OF AROMATIC NITRO COMPOUNDS, AZOBENZENE, AND AZOXYBENZENE ON PALLADIUM CATALYSTS CONTAINING MOLYBDENUM AND VANADIUM

Lapidus, A. L.,Manov-Yuvenskii, V. I.,Petrovskii, K. B.

, p. 2282 - 2284 (1981)

-

-

Manov-Yuvenskii,Nefedov

, (1979)

-

The curtius rearrangement of acyl azides revisited - Formation of cyanate (R-O-CN)

Wentrup, Curt,Bornemann, Holger

, p. 4521 - 4524 (2005)

The Curtius rearrangement is a synthesis of isocyanates (R-N=C=O) by thermal or photochemical rearrangement of acyl acides and/or acylnitrenes. The photochemical rearrangement of benzoyl azide is now shown for the first time to produce a small amount of phenyl cyanate (Ph-O-CN) together with phenyl isocyanate. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.

CATALYTIC CARBONYLATION OF NITRO COMPOUNDS IN THE PRESENCE OF CARBONYL IONIC COMPLEXES OF Rh(I), Ir(I), Pd(I), AND Pd(II)

Abakumov, G. A.,Knyazeva, I. L.,Vavilina, N. N.,Gorbunova, L. V.,Zhivtsova, S. V.

, p. 1242 - 1245 (1984)

-

EFFECT OF CATALYST COMPOSITION AND REACTION CONDITIONS ON SYNTHESIS OF PHENYL ISOCYANATE BY CARBONYLATION OF NITROBENZENE

Manov-Yuvenskii, V. I.,Nefedov, B. K.,Smetanin, A. V.

, p. 1817 - 1819 (1980)

-

Reactivity of Carbamoyl Radicals: the First General and Convenient Free-radical Synthesis of Isocyanates

Minisci, Francesco,Coppa, Fausta,Fontana, Francesca

, p. 679 - 680 (1994)

The first free-radical synthesis of isocyanates was performed by oxidation of oxalic acid monoamides by S2O82-, catalysed by silver(I) and copper(II) salts, in a two-phase system.

Synthesis and biological evaluation of novel 4-(4-formamidophenylamino)-N-methylpicolinamide derivatives as potential antitumor agents

Hu, Min,Meng, Nana,Xia, Yong,Xu, Youzhi,Yu, Luoting,Zeng, Xiuxiu,Zhou, Shuyan

, (2021)

A novel series of 4-(4-formamidophenylamino)-N-methylpicolinamide derivatives were synthesized and evaluated against different tumor cell lines. Experiments in vitro showed that these derivatives could inhibit the proliferation of two kinds of human cancer cell lines (HepG2, HCT116) at low micromolar concentrations and the most potent analog 5q possessed broad-spectrum antiproliferative activity. Experiments in vivo demonstrated that 5q could effectively prolong the longevity of colon carcinoma-burdened mice and slow down the progression of cancer cells by suppression of angiogenesis and the induction of apoptosis and necrosis.

-

Hofmann,A. W.

, p. 655 (1870)

-

Synthesis of new coumarin compounds and its hypoglycemic activity and structure-activity relationship

Qi, Gang,Zhang, Wenguo

, p. 9835 - 9839 (2013)

Novel coumarin compounds were designed and synthesized by combining the active moieties of hypoglycemic drugs. The coumarin compounds were made by sulfanilamide with isocynate, the intermediate sulfanilamide was formed from coumarin by chlorosulfonated and aminated. These targeted compounds were characterized by FT-IR, 1H NMR and MS spectra and their hypoglycemic activities were evaluated in mice. The preliminary results showed that some compounds exhibited evident hypoglycemic effect (P > 0.01, CMC-Na as negative control). The relationship between these compounds structure with their hypoglycemic activities were studied in order to design new antidiabetic agents.

-

Magee,Daniels

, p. 829 (1957)

-

-

Mukaiyama,T. et al.

, p. 4381 - 4384 (1961)

-

Preparation and photocatalytic property of hexagonal cylinder-like bipods ZnO microcrystal photocatalyst

Liu, Yumin,Hua, Lv,Li, Shuangqing,Xing, Xinyan,Xi, Guoxi

, p. 443 - 449 (2012)

Single crystalline ZnO with hexagonal cylinder-like bipods morphologies were successfully synthesized via a cationic surfactant-assisted hydrothermal microemulsion route. The structure, morphologies and properties of the as-prepared samples were determined using X-ray diffraction, scanning electron microscopy, photoluminescence spectrum and Ultraviolet and Visible absorption spectroscopy. The photocatalytic activities of the obtained products were evaluated by the degradation of Reactive Brilliant Red K-2BP in aqueous solution under a variety of conditions. Under the optimum condition, approximately 99.5% decolorization efficiency within 45 min and 65.3% TOC removal efficiency within 3 h were achieved, which were higher than that by the commercial ZnO. Moreover, the degradation products were analyzed by a gas chromatography coupled with mass spectrometry system and the probable pathways for the formation of the intermediates were proposed. The photocatalytic results indicated that the as-prepared ZnO showed good photocatalytic activity and it could be considered as a promising photocatalyst for dyes wastewater treatment.

EFFECT OF SOLVENT AND TRANSITION-METAL OXIDE AND CHLORIDE ON CATALYST ACTIVITY IN PHENYL ISOCYANATE SYNTHESIS BY NITROBENZENE CARBOXYLATION

Manov-Yuvenskii, V. I.,Nefedov, B. K.

, p. 816 - 819 (1981)

-

-

Bamberger,Destraz

, p. 1885 (1902)

-

Thermal Decomposition of Benzoyl Azide and Diazoacetone in the Gas Phase

Prokudin, V. G.,Sipyagin, A. M.,Kartsev, V. G.,Vozchikova, S. A.

, p. 1541 - 1544 (1988)

-

Coleman et al.

, p. 4534,4535 (1954)

Design, synthesis and structure-activity relationships of novel diaryl urea derivatives as potential EGFR inhibitors

Jiang, Nan,Bu, Yanxin,Wang, Yu,Nie, Minhua,Zhang, Dajun,Zhai, Xin

, (2016)

Two novel series of diaryl urea derivatives 5a-i and 13a-l were synthesized and evaluated for their cytotoxicity against H-460, HT-29, A549, and MDA-MB-231 cancer cell lines in vitro. Therein, 4-aminoquinazolinyl-diaryl urea derivatives 5a-i demonstrated significant activity, and seven of them are more active than sorafenib, with IC50 values ranging from 0.089 to 5.46 μM. Especially, compound 5a exhibited the most active potency both in cellular (IC50 = 0.15, 0.089, 0.36, and 0.75 μM, respectively) and enzymatic assay (IC50 = 56 nM against EGFR), representing a promising lead for further optimization.

Synthesis and Crystal Structure of , a Ruthenium Cluster with a Phenyl Isocyanate Ligand

Bhaduri, Sumit,Khwaja, Hanif,Jones, Peter G.

, p. 194 - 195 (1988)

The ruthenium cluster = (Ph3P)2N> has been synthesised by intramolecular nucleophilic attack on CO and characterised by X-ray structure determination.

Aminolysis of phenyl N-phenylcarbamate via an isocyanate intermediate: Theory and experiment

Ilieva, Sonia,Nalbantova, Didi,Hadjieva, Boriana,Galabov, Boris

, p. 6440 - 6449 (2013)

A comprehensive examination of the mechanism of the uncatalyzed and base-catalyzed aminolysis of phenyl N-phenylcarbamate by theoretical quantum mechanical methods at M06-2X/6-311+G(2d,2p) and B3LYP-D3/6-31G(d,p) levels, combined with an IR spectroscopic study of the reaction, was carried out. Three alternative reaction channels were theoretically characterized: concerted, stepwise via a tetrahedral intermediate, and stepwise involving an isocyanate intermediate. In contrast to dominating views, the theoretical results revealed that the reaction pathway through the isocyanate intermediate (E1cB) is energetically favored. These conclusions were supported by an IR spectroscopic investigation of the interactions of phenyl N-phenylcarbamate with several amines possessing varying basicities and nucleophilicities: n-butylamine, diethylamine, triethylamine, N-methylpyrrolidine, and trimethylamine. The reactivity of substituted phenyl N-phenylcarbamates in the aminolysis reaction was rationalized using theoretical and experimental reactivity indexes: electrostatic potential at nuclei (EPN), Hirshfeld and NBO atomic charges, and Hammett constants. The obtained quantitative relationships between these property descriptors and experimental kinetic constants reported in the literature emphasize the usefulness of theoretical parameters (EPN, atomic charges) in characterizing chemical reactivity.

Discovery of Potent EGFR Inhibitors With 6-Arylureido-4-anilinoquinazoline Derivatives

Li, Meng,Xue, Na,Liu, Xingang,Wang, Qiaoyun,Yan, Hongyi,Liu, Yifan,Wang, Lei,Shi, Xiaowei,Cao, Deying,Zhang, Kai,Zhang, Yang

, (2021/06/14)

According to the classical pharmacophore fusion strategy, a series of 6-arylureido-4-anilinoquinazoline derivatives (Compounds 7a–t) were designed, synthesized, and biologically evaluated by the standard CCK-8 method and enzyme inhibition assay. Among the title compounds, Compounds 7a, 7c, 7d, 7f, 7i, 7o, 7p, and 7q exhibited promising anti-proliferative bioactivities, especially Compound 7i, which had excellent antitumor activity against the A549, HT-29, and MCF-7 cell lines (IC50 = 2.25, 1.72, and 2.81?μM, respectively) compared with gefitinib, erlotinib, and sorafenib. In addition, the enzyme activity inhibition assay indicated that the synthesized compounds had sub-micromolar inhibitory levels (IC50, 11.66–867.1?nM), which was consistent with the results of the tumor cell line growth inhibition tests. By comparing the binding mechanisms of Compound 7i (17.32?nM), gefitinib (25.42?nM), and erlotinib (33.25?nM) to the EGFR, it was found that Compound 7i could extend into the effective region with a similar action conformation to that of gefitinib and interact with residues L85, D86, and R127, increasing the binding affinity of Compound 7i to the EGFR. Based on the molecular hybridization strategy, 14 compounds with EGFR inhibitory activity were designed and synthesized, and the action mechanism was explored through computational approaches, providing valuable clues for the research of antitumor agents based on EGFR inhibitors.

Hypervalent Iodine Reagent-Promoted Hofmann-Type Rearrangement/Carboxylation of Primary Amides

Wang, Xia,Yang, Peng,Hu, Bo,Zhang, Qian,Li, Dong

supporting information, p. 2820 - 2826 (2021/02/01)

A novel transformation of primary amides to secondary amides promoted by hypervalent iodine reagents was developed. The hypervalent iodine reagent-mediated Hofmann-type rearrangement generated an isocyanate intermediate, which was subsequently trapped by an in situ generated carboxylic acid from the hypervalent iodine reagent to provide the corresponding secondary amides. This method provided a facile and efficient route for the synthesis of secondary amides from primary amides and also revealed novel reactivities of hypervalent iodine reagents.