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103-72-0

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103-72-0 Usage

Chemical Description

Different sources of media describe the Chemical Description of 103-72-0 differently. You can refer to the following data:
1. Phenyl isothiocyanate is a reagent used in one of the reactions to form a yellow-colored product.
2. Phenyl isothiocyanate is an organic compound that contains a phenyl group and an isothiocyanate group.

Chemical Properties

colourless to pale yellow liquid with a penetrating odour

Uses

Different sources of media describe the Uses of 103-72-0 differently. You can refer to the following data:
1. Phenyl isothiocyanate is the reagent of choice in automated Edman degradation systems. However, this reagent is highly toxic and for manual modification other reagents are preferred such as dimethy laminoazobenzene isothiocyanate (Chang, 1983; Wang et al, 2000) or trifluoroethyl isothiocyanate (Bartlet-Jones et al, 1994). This last reagent has the advantage of being volatile, so that the excess of reagent is easily removed by vacuum before MS analysis (Spengler, 1997). This compound was used successfully during seven successive cycles of manual cleavage coupled with MS analysis. Nevertheless, the high reactivity of such compounds seems to shows artefactual modification such as“acetylation' of the hydroxyl groups of the Ser and Thr. Allyl isothiocyanate shows better selectivity, but again this reagent is toxic and difficult to use in manual approaches (Gu & Preswich, 1997) .
2. Phenyl isothiocyanate acts as a derivatizing reagent for primary and secondary amines. It is used in sequencing peptides by Edman degradation and in amino acid analyses by HPLC. It is used for derivatizing N-terminal amino acids of proteins for automated sequential analysis. It is a synthon for dithiadiazafulvalenes.

Definition

ChEBI: Phenyl isothiocyanate is an isothiocyanate having a phenyl group attached to the nitrogen; used for amino acid sequencing in the Edman degradation. It has a role as an allergen and a reagent.

Preparation

Synthetic procedure for phenyl isothiocyanate in 1-mol scaleInto a 2-L jacketed flask, 91.2 g of CS2 (1.2 mol) was dropwise added to a mixture of aniline (93.0 g, 1.0 mol) and K2CO3 (276.0 g, 2.0 mol) in 700 mL of water at room temperature within a period of 2.5 h. After the addition was complete, the mixture was stirred another 2 h. Then, the mixture was cooled to 0 °C, and a solution of 92.3 g of TCT (0.5 mol) in 450 mL of CH2Cl2 was dropwise added within 4 h. After the addition was complete, the mixture was stirred another 1 h to complete the conversion. The resulting mixture was basified to pH >11 with 250 mL of 6 N NaOH and yielded a clear solution. The organic layer was separated and the aqueous layer was extracted with 150 mL of CH2Cl2. The combined organic layers were dried over anhydrous Na2SO4, filtered, and the solvent of filtrate was removed via distillation under atmospheric pressure with a 25-cm Vigreux column. The residue was vacuum distilled and the desired product fraction was collected at 72–74 °C/1 mmHg. Finally, 127.0 g of colorless liquid (94%) was obtained.

Biological Functions

Phenyl isothiocyanate (PITC) is a well-established reagent in protein chemistry since its introduction in Edman degradation. PITC reacts with primary and secondary amines under alkaline conditions within 20 min. The resulting phenylthiocarbamyl (PTC) derivatives of the amino acids are stable and do not interfere with reaction by-products during chromatography. The absorption maximum is around 245 nm with a detection limit of 1 pmol.Phenyl isothiocyanate may be employed as a derivatization reagent for high-performance liquid chromatographic (HPLC) analysis of various amphetamine derivatives in body fluids for forensic purposes.

Synthesis Reference(s)

Tetrahedron Letters, 38, p. 1597, 1997 DOI: 10.1016/S0040-4039(97)00121-4Synthesis, p. 300, 1989 DOI: 10.1055/s-1989-27231Tetrahedron Letters, 23, p. 447, 1982 DOI: 10.1016/S0040-4039(00)86856-2

General Description

Phenyl isothiocyanate is an aromatic isothiocyanate. It participates in dehydration reactions of alcohols. It is widely used for synthesis of various biologically important heterocyclic compounds.

Purification Methods

It is insoluble in H2O, but soluble in Et2O and EtOH. If impure (due to formation of thiourea), then steam distil it into a receiver containing 5-10mL of N H2SO4. Separate the oil, dry over CaCl2 and distil it under vacuum. [Dains et al. Org Synth Coll Vol I 447 1941, Beilstein 12 IV 867.]

Check Digit Verification of cas no

The CAS Registry Mumber 103-72-0 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 2 respectively.
Calculate Digit Verification of CAS Registry Number 103-72:
(5*1)+(4*0)+(3*3)+(2*7)+(1*2)=30
30 % 10 = 0
So 103-72-0 is a valid CAS Registry Number.
InChI:InChI=1/C7H5NS/c9-6-8-7-4-2-1-3-5-7/h1-5H

103-72-0 Well-known Company Product Price

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  • (Code)Product description
  • CAS number
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  • Detail
  • Alfa Aesar

  • (A11596)  Phenyl isothiocyanate, 97%   

  • 103-72-0

  • 5g

  • 191.0CNY

  • Detail
  • Alfa Aesar

  • (A11596)  Phenyl isothiocyanate, 97%   

  • 103-72-0

  • 100g

  • 393.0CNY

  • Detail
  • Alfa Aesar

  • (A11596)  Phenyl isothiocyanate, 97%   

  • 103-72-0

  • 500g

  • 1363.0CNY

  • Detail
  • Sigma

  • (P1034)  Phenylisothiocyanate  Sigma Grade, 8.36 M, suitable for solid phase protein sequencing analysis, ≥99% (GC), liquid

  • 103-72-0

  • P1034-1ML

  • 321.75CNY

  • Detail
  • Sigma

  • (P1034)  Phenylisothiocyanate  Sigma Grade, 8.36 M, suitable for solid phase protein sequencing analysis, ≥99% (GC), liquid

  • 103-72-0

  • P1034-10ML

  • 1,838.07CNY

  • Detail
  • Sigma

  • (P1034)  Phenylisothiocyanate  Sigma Grade, 8.36 M, suitable for solid phase protein sequencing analysis, ≥99% (GC), liquid

  • 103-72-0

  • P1034-10X1ML

  • 1,870.83CNY

  • Detail
  • Sigma-Aldrich

  • (78780)  Phenylisothiocyanate  for HPLC derivatization, the detection of alcohols and amines, ≥99.0%

  • 103-72-0

  • 78780-25ML

  • 579.15CNY

  • Detail
  • Sigma-Aldrich

  • (78780)  Phenylisothiocyanate  for HPLC derivatization, the detection of alcohols and amines, ≥99.0%

  • 103-72-0

  • 78780-100ML

  • 1,835.73CNY

  • Detail
  • Sigma-Aldrich

  • (78780)  Phenylisothiocyanate  for HPLC derivatization, the detection of alcohols and amines, ≥99.0%

  • 103-72-0

  • 78780-500ML

  • 6,534.45CNY

  • Detail
  • Sigma

  • (317861)  Phenylisothiocyanate  99%, for protein sequencing

  • 103-72-0

  • 317861-1G

  • 372.06CNY

  • Detail
  • Sigma

  • (317861)  Phenylisothiocyanate  99%, for protein sequencing

  • 103-72-0

  • 317861-5G

  • 937.17CNY

  • Detail

103-72-0SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name phenyl isothiocyanate

1.2 Other means of identification

Product number -
Other names isothiocyanatobenzene

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
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:103-72-0 SDS

103-72-0Synthetic route

carbon disulfide
75-15-0

carbon disulfide

aniline
62-53-3

aniline

phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

Conditions
ConditionsYield
Stage #1: carbon disulfide; aniline With triethylamine In ethanol at 20℃;
Stage #2: With dmap; di-tert-butyl dicarbonate In ethanol at 20℃; for 0.25h; Further stages.;
100%
Stage #1: carbon disulfide; aniline With potassium carbonate In water at 20℃; for 3h; Inert atmosphere;
Stage #2: With 1,3,5-trichloro-2,4,6-triazine In dichloromethane; water at 0℃; for 0.5h; Inert atmosphere;
Stage #3: With sodium hydroxide In dichloromethane; water pH=11; Inert atmosphere;
98%
Stage #1: carbon disulfide; aniline With potassium carbonate In water at 20℃;
Stage #2: With 1,3,5-trichloro-2,4,6-triazine In dichloromethane; water at 0℃; for 0.5h;
98%
phenyl-dithiocarbamic acid; sodium salt
18418-42-3

phenyl-dithiocarbamic acid; sodium salt

N-phenyl-benzimidoyl chloride
4903-36-0

N-phenyl-benzimidoyl chloride

A

phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

B

N-Phenylbenzothioamide
636-04-4

N-Phenylbenzothioamide

Conditions
ConditionsYield
In diethyl ether 0 deg C to r.t.;A 91%
B 99%
benzohydroximoyl chloride
698-16-8

benzohydroximoyl chloride

phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

Conditions
ConditionsYield
With triethylamine; thiourea In tetrahydrofuran Ambient temperature;99%
With triethylamine; thiourea In tetrahydrofuran Product distribution; Ambient temperature; reactions of derivatives;99%
With OuadraPure Thiaurea resin; SIO2-pyridine In acetonitrile at 50℃; for 0.166667h; Flow reactor;91%
Stage #1: benzohydroximoyl chloride With triethylamine In dichloromethane for 2h;
Stage #2: With zinc(II) chloride In toluene for 24h; Heating; Further stages.;
84%
Multi-step reaction with 2 steps
1: triethylamine / dichloromethane-d2; methanol
2: dichloromethane-d2 / 3 h
View Scheme
N-(2-Benzothienocarbonyl)-N'-phenylthiourea
115957-60-3

N-(2-Benzothienocarbonyl)-N'-phenylthiourea

A

benzo[b]thiophene-2-carboxamide
6314-42-7

benzo[b]thiophene-2-carboxamide

B

phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

Conditions
ConditionsYield
In acetone for 1h; Irradiation;A 98%
B n/a
In acetone for 1h; Product distribution; Irradiation;A 98%
B n/a
potassium aniline dithiocarbamate
51034-34-5

potassium aniline dithiocarbamate

phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

Conditions
ConditionsYield
With 1,3,5-trichloro-2,4,6-triazine In dichloromethane at 0℃; for 0.5h;98%
With 1,3,5-trichloro-2,4,6-triazine In dichloromethane; water; N,N-dimethyl-formamide at 0℃;
With sodium persulfate; potassium carbonate In water at 20℃; for 1h; Green chemistry; chemoselective reaction;
aniline dithiocarbamate(1-)
22296-13-5

aniline dithiocarbamate(1-)

phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

Conditions
ConditionsYield
With iron(III) chloride; sodium acetate In acetone at 20℃; for 2h; Catalytic behavior; Reagent/catalyst; Solvent;98%
With bis(trichloromethyl) carbonate In dichloromethane at 20℃; for 4h;
phenyl isocyanate
1197040-29-1

phenyl isocyanate

dimethyl 2-(4-ethyl-3-oxo-6-thioxo-3H,4H-[1,2]dithiolo[3,4-b][1,4]thiazin-5(6H)-ylidene)-1,3-dithiole-4,5-dicarboxylate
461679-19-6

dimethyl 2-(4-ethyl-3-oxo-6-thioxo-3H,4H-[1,2]dithiolo[3,4-b][1,4]thiazin-5(6H)-ylidene)-1,3-dithiole-4,5-dicarboxylate

A

C21H16N2O5S5
1256095-52-9

C21H16N2O5S5

B

phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

Conditions
ConditionsYield
In tetrachloromethane for 6h; Reflux;A 71%
B 97%
Thiram
137-26-8

Thiram

aniline
62-53-3

aniline

phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

Conditions
ConditionsYield
With toluene-4-sulfonic acid In water at 60 - 85℃; for 4h; Autoclave;96.3%
In water at 90 - 100℃; for 4h; Large scale;74.38%
N-phenyldithiocarbamic acid
40231-24-1

N-phenyldithiocarbamic acid

phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

Conditions
ConditionsYield
With 1,1'-(ethane-1,2-diyl)dipyridinium bistribromide; triethylamine In acetonitrile Cooling with ice;96%
With lead(II) nitrate In ammonium hydroxide
With chloroformic acid ethyl ester In water at 20℃;
With cobalt(II) chloride hexahydrate; sodium hydrogencarbonate In ethyl acetate at 20℃; for 1h; Catalytic behavior; Solvent; Reagent/catalyst; Temperature;
phenyldithiocarbamic acid triethylamine salt
43009-16-1

phenyldithiocarbamic acid triethylamine salt

phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

Conditions
ConditionsYield
With [bis(acetoxy)iodo]benzene; triethylamine In acetonitrile Cooling with ice;96%
With iodine; triethylamine In acetonitrile at 5℃; Cooling with ice;96%
With iron(III) chloride; triethylamine In acetone at 20℃; for 2h; Solvent;95%
1,1'-Thiocarbonyldi-2(1H)-pyridone
102368-13-8

1,1'-Thiocarbonyldi-2(1H)-pyridone

aniline
62-53-3

aniline

phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

Conditions
ConditionsYield
In dichloromethane for 0.2h; Ambient temperature;96%
tetraphenylarsine imide
33708-54-2

tetraphenylarsine imide

A

triphenyl arsine sulfide
3937-40-4

triphenyl arsine sulfide

B

phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

Conditions
ConditionsYield
With carbon disulfide In benzene at 40℃; for 48h;A 93.2%
B 80.9%
methyl N-phenyldithiocarbamate
701-73-5

methyl N-phenyldithiocarbamate

phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

Conditions
ConditionsYield
With sodium hydroxide In toluene for 1.5h; Heating;93%
Multi-step reaction with 2 steps
1: iodine; alcohol
2: 100 - 130 °C
View Scheme
With mercury(II) oxide In diethyl ether at 20℃; for 1h;
3'-phenyladamantane-2-spiro-5'-(1',4',2'-oxathiazoline)
95549-15-8

3'-phenyladamantane-2-spiro-5'-(1',4',2'-oxathiazoline)

A

2-Adamantanone
700-58-3

2-Adamantanone

B

phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

Conditions
ConditionsYield
at 185℃; under 30 Torr; for 0.5h;A 73%
B 93%
potassium cyanate
590-28-3

potassium cyanate

3-Phenyl-5-[2-(4-methylphenyl)-2-oxoethyl]-4-oxo-2-thioxo-1,3-thiazolidine

3-Phenyl-5-[2-(4-methylphenyl)-2-oxoethyl]-4-oxo-2-thioxo-1,3-thiazolidine

A

2,4-bis[2-(4-methylphenyl)-2-oxoethylidene]cyclobutane-1,3-dione
1075256-92-6

2,4-bis[2-(4-methylphenyl)-2-oxoethylidene]cyclobutane-1,3-dione

B

phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

Conditions
ConditionsYield
In 1,4-dioxane; methanol at 90℃; for 0.416667h;A n/a
B 93%
N1,N2-bis[N-phenylthiocarbamoyl]-1,2-diaminobenzene
50521-79-4

N1,N2-bis[N-phenylthiocarbamoyl]-1,2-diaminobenzene

A

(1H-benzoimidazol-2-yl)phenylamine
21578-58-5

(1H-benzoimidazol-2-yl)phenylamine

B

phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

Conditions
ConditionsYield
With [bis(acetoxy)iodo]benzene; triethylamineA 93%
B n/a
With 1,1'-(ethane-1,2-diyl)dipyridinium bistribromide; triethylamine In acetonitrile at 20℃;A 91%
B n/a
aniline
62-53-3

aniline

tetramethylammonium trifluoromethanethiolate

tetramethylammonium trifluoromethanethiolate

phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 0.166667h;93%
With triethylamine In dichloromethane at 20℃; for 0.166667h;92%
phenyl-dithiocarbamic acid; sodium salt
18418-42-3

phenyl-dithiocarbamic acid; sodium salt

N-o-Chlorphenylacetimidchlorid
73357-06-9

N-o-Chlorphenylacetimidchlorid

A

thioacetic acid-(2-chloro-anilide)
39184-83-3

thioacetic acid-(2-chloro-anilide)

B

phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

Conditions
ConditionsYield
In diethyl ether 0 deg C to r.t.;A 92%
B 90%
phenyl isocyanate
1197040-29-1

phenyl isocyanate

phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

Conditions
ConditionsYield
With selenium; sulfur; triethylamine In tetrahydrofuran for 2h; Heating;91%
With sulfur
N,N-diphenylthiourea
102-08-9

N,N-diphenylthiourea

phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

Conditions
ConditionsYield
With Phenyltrichlorosilane at 140 - 195℃; for 1h;90%
With phosphorus pentaoxide
With phosphoric acid
carbon disulfide
75-15-0

carbon disulfide

2,2,2-trifluoro-N-phenylacetamide
404-24-0

2,2,2-trifluoro-N-phenylacetamide

phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

Conditions
ConditionsYield
With potassium carbonate In 1,4-dioxane at 50 - 90℃; for 3.5h;90%
With sodium hydroxide; potassium carbonate In acetonitrile at 25℃; for 1h;71%
di-2-pyridyl thionocarbonate
96989-50-3

di-2-pyridyl thionocarbonate

aniline
62-53-3

aniline

phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

Conditions
ConditionsYield
In dichloromethane for 0.0833333h; Ambient temperature;90%
In dichloromethane at 20℃; for 2h;
In dichloromethane Inert atmosphere;
1-bromo-2-isothiocyanatobenzene
13037-60-0

1-bromo-2-isothiocyanatobenzene

phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

Conditions
ConditionsYield
Stage #1: 1-bromo-2-isothiocyanatobenzene With n-butyllithium In tetrahydrofuran; hexane at 0℃;
Stage #2: With methanol In tetrahydrofuran; hexane at 0℃; Temperature;
90%
Stage #1: 1-bromo-2-isothiocyanatobenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃;
Stage #2: With butyl isothiocyanate In tetrahydrofuran; hexane Cooling;
N-phenyl-O-phenylthiocarbamate
2423-29-2

N-phenyl-O-phenylthiocarbamate

phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

Conditions
ConditionsYield
With sodium hydroxide In dichloromethane at 20℃; for 1h;90%
Formanilid
103-70-8

Formanilid

phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

Conditions
ConditionsYield
With bis(trichloromethyl) carbonate; sulfur; triethylamine; selenium In dichloromethane for 6.5h; Heating;89%
phenyldithiocarbamic acid triethylamine salt
43009-16-1

phenyldithiocarbamic acid triethylamine salt

acrylic acid methyl ester
292638-85-8

acrylic acid methyl ester

A

methyl 3-((phenylcarbamothioyl)thio)propanoate
56624-42-1

methyl 3-((phenylcarbamothioyl)thio)propanoate

B

phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

Conditions
ConditionsYield
at 20℃; for 0.5h; pH=7 - 7.44; aq. phosphate buffer;A 88%
B 5%
at 20℃; for 0.5h; pH=10 - 10.18; aq. phosphate buffer;A 8%
B 82%
aniline
62-53-3

aniline

phenylcarbonochloridothioate
1005-56-7

phenylcarbonochloridothioate

phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

Conditions
ConditionsYield
With sodium hydroxide In dichloromethane at 0 - 20℃; for 10h; Reagent/catalyst; Solvent; Time; Concentration;88%
In toluene at 115℃; for 16h; Green chemistry;80%
With triethylamine In dichloromethane at 0 - 20℃; for 15h;35%
carbon disulfide
75-15-0

carbon disulfide

C18H15NPS(1-)*Na(1+)

C18H15NPS(1-)*Na(1+)

phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

Conditions
ConditionsYield
Ambient temperature;87%
As,As,As-tris(p-chlorophenyl)-N-phenylarsine imide
113827-42-2

As,As,As-tris(p-chlorophenyl)-N-phenylarsine imide

A

phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

B

tris(p-chlorophenyl)arsine sulfide

tris(p-chlorophenyl)arsine sulfide

Conditions
ConditionsYield
With carbon disulfide for 24h;A n/a
B 86%
1-(2-pyridyl)piperazine
34803-66-2

1-(2-pyridyl)piperazine

phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

N-phenyl-4-(pyridin-2-yl)piperazine-1-carbothioamide
330865-56-0

N-phenyl-4-(pyridin-2-yl)piperazine-1-carbothioamide

Conditions
ConditionsYield
Stage #1: 1-(2-pyridyl)piperazine; phenyl isothiocyanate In dichloromethane at 60℃;
Stage #2: With isatoic anhydride-N-(CH2)3-C8F17 In dichloromethane at 60℃; for 2.5h;
100%
phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

N1,N2-bis[N-phenylthiocarbamoyl]-1,2-diaminobenzene
50521-79-4

N1,N2-bis[N-phenylthiocarbamoyl]-1,2-diaminobenzene

Conditions
ConditionsYield
In methanol for 3h;100%
In methanol for 3h;99%
With ethanol
phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

(2,4-dinitro-phenyl)-hydrazine
119-26-6

(2,4-dinitro-phenyl)-hydrazine

2-(2',4'-dinitrophenyl)-N-phenyl-1-hydrazinecarbothioamide
105394-88-5

2-(2',4'-dinitrophenyl)-N-phenyl-1-hydrazinecarbothioamide

Conditions
ConditionsYield
at 20℃;100%
With ethanol
In ethanol Heating;
phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

1-amino-2-propene
107-11-9

1-amino-2-propene

1-allyl-3-phenyl-thiourea
7341-63-1

1-allyl-3-phenyl-thiourea

Conditions
ConditionsYield
In acetonitrile at 20℃; for 3h;100%
With diethyl ether
phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

N-methylaniline
100-61-8

N-methylaniline

1-methyl-1,3-diphenyl-thiourea
4949-93-3

1-methyl-1,3-diphenyl-thiourea

Conditions
ConditionsYield
In ethanol at 25 - 30℃; for 1h;100%
Wavelength; Reagent/catalyst; Darkness;97%
In ethanol for 0.166667h; Heating;60%
phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

benzylamine
100-46-9

benzylamine

1-benzyl-3-phenylthiourea
726-25-0

1-benzyl-3-phenylthiourea

Conditions
ConditionsYield
In acetonitrile at 20℃; for 3h;100%
In acetonitrile at 25℃; for 0.166667h; Milling;99%
With C64H52CaN6 In neat (no solvent) at 60℃; for 12h; Schlenk technique; Glovebox; Inert atmosphere;98%
phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

2-bromoaniline
615-36-1

2-bromoaniline

1-(2-bromophenyl)-3-phenylthiourea
25688-29-3

1-(2-bromophenyl)-3-phenylthiourea

Conditions
ConditionsYield
In ethanol at 20℃; for 2h;100%
In N,N-dimethyl-formamide Heating;99%
With C64H52CaN6 In neat (no solvent) at 60℃; for 12h; Schlenk technique; Glovebox; Inert atmosphere;85%
phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

monophenylthiourea
103-85-5

monophenylthiourea

Conditions
ConditionsYield
With ammonia at -30℃; under 300.024 Torr; Addition; solid-gas reaction;100%
With ammonium hydroxide In water; acetonitrile at 20℃; for 3h;100%
With ammonia In 1,2-dimethoxyethane99%
morpholine
110-91-8

morpholine

phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

N-phenyl-1-morpholinethiocarbamide
15093-54-6

N-phenyl-1-morpholinethiocarbamide

Conditions
ConditionsYield
In ethanol at 25 - 30℃; for 1h;100%
In acetonitrile at 25℃; for 0.166667h; Milling;99%
In acetonitrile at 20℃; Inert atmosphere;96%
1,2,3,4-tetrahydroisoquinoline
91-21-4

1,2,3,4-tetrahydroisoquinoline

phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

3,4-dihydro-1H-isoquinoline-2-carbothioic acid phenylamide
89652-23-3

3,4-dihydro-1H-isoquinoline-2-carbothioic acid phenylamide

Conditions
ConditionsYield
Stage #1: 1,2,3,4-tetrahydroisoquinoline; phenyl isothiocyanate In dichloromethane at 60℃;
Stage #2: With isatoic anhydride-N-(CH2)3-C8F17 In dichloromethane at 60℃; for 2.5h;
100%
In acetonitrile at 20℃; for 0.25h; Inert atmosphere;92%
With pyridine a) room temperature, 10 min, b) 50 deg C, 10 min;
In N,N-dimethyl-formamide 1.) RT, 10 min, 2.) 60 deg C, 10 min;
In tetrahydrofuran at 20℃;
1-Dimethylamino-1-methylmercapto-ethen
24854-14-6

1-Dimethylamino-1-methylmercapto-ethen

phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

(Z)-3-Dimethylamino-3-methylsulfanyl-N-phenyl-thioacrylamide
92486-88-9

(Z)-3-Dimethylamino-3-methylsulfanyl-N-phenyl-thioacrylamide

Conditions
ConditionsYield
In diethyl ether for 4h; Ambient temperature;100%
In diethyl ether Ambient temperature;
diphenylphosphinic acid hydrazide
6779-66-4

diphenylphosphinic acid hydrazide

phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

1-diphenylphosphinoyl-4-phenyl-thiosemicarbazide
30426-16-5

1-diphenylphosphinoyl-4-phenyl-thiosemicarbazide

Conditions
ConditionsYield
With 1-methyl-1H-imidazole In benzene at 25℃; Rate constant; var. conc. of diarylphosphinic hydrazide;100%
In benzene at 25℃; Rate constant;
isoquinoline In benzene at 25℃; Rate constant; catalytic activity of different substituted benzopyridines in the reaction, in various concentrations;
di-p-tolylphosphorohydrazide
51104-00-8

di-p-tolylphosphorohydrazide

phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

C21H22N3OPS

C21H22N3OPS

Conditions
ConditionsYield
With 1-methyl-1H-imidazole In benzene at 25℃; Rate constant; var. conc. of diarylphosphinic hydrazide;100%
In benzene at 25℃; Rate constant; Mechanism;
In benzene at 24.9 - 54.9℃; Rate constant; Thermodynamic data; Kinetics; Ea, ΔS(excit.), ΔH(excit.), ΔG(excit.);
Di-m-tolyl-phosphinsaeurehydrazid
51104-01-9

Di-m-tolyl-phosphinsaeurehydrazid

phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

C21H22N3OPS

C21H22N3OPS

Conditions
ConditionsYield
With 1-methyl-1H-imidazole In benzene at 25℃; Rate constant; var. conc. of diarylphosphinic hydrazide;100%
In benzene at 25℃; Rate constant; Mechanism;
With pyridine In benzene at 25℃; Rate constant;
Di-p-chlorophenyl-phosphinsaeurehydrazid
51104-02-0

Di-p-chlorophenyl-phosphinsaeurehydrazid

phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

C19H16Cl2N3OPS

C19H16Cl2N3OPS

Conditions
ConditionsYield
With 1-methyl-1H-imidazole In benzene at 25℃; Rate constant; var. conc. of diarylphosphinic hydrazide;100%
In benzene at 25℃; Rate constant; Mechanism;
In benzene at 24.9 - 54.9℃; Rate constant; Thermodynamic data; Kinetics; Ea, ΔS(excit.), ΔH(excit.), ΔG(excit.);
Di-p-bromophenyl-phosphinsaeurehydrazid
51104-03-1

Di-p-bromophenyl-phosphinsaeurehydrazid

phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

C19H16Br2N3OPS

C19H16Br2N3OPS

Conditions
ConditionsYield
With 1-methyl-1H-imidazole In benzene at 25℃; Rate constant; var. conc. of diarylphosphinic hydrazide;100%
In benzene at 25℃; Rate constant; Mechanism;
In benzene at 24.9 - 54.9℃; Rate constant; Thermodynamic data; Kinetics; Ea, ΔS(excit.), ΔH(excit.), ΔG(excit.);
Di-m-bromophenyl-phosphinsaeurehydrazid
51104-04-2

Di-m-bromophenyl-phosphinsaeurehydrazid

phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

C19H16Br2N3OPS

C19H16Br2N3OPS

Conditions
ConditionsYield
With 1-methyl-1H-imidazole In benzene at 25℃; Rate constant; var. conc. of diarylphosphinic hydrazide;100%
In benzene at 25℃; Rate constant; Mechanism;
In benzene at 24.9 - 54.9℃; Rate constant; Thermodynamic data; Kinetics; Ea, ΔS(excit.), ΔH(excit.), ΔG(excit.);
Di-p-methoxyphenyl-phosphinsaeurehydrazid
51103-99-2

Di-p-methoxyphenyl-phosphinsaeurehydrazid

phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

C21H22N3O3PS

C21H22N3O3PS

Conditions
ConditionsYield
With 1-methyl-1H-imidazole In benzene at 25℃; Rate constant; Mechanism; var. conc. of diarylphosphinic hydrazide;100%
In benzene at 25℃; Rate constant; Mechanism;
In benzene at 24.9 - 54.9℃; Rate constant; Thermodynamic data; Kinetics; Ea, ΔS(excit.), ΔH(excit.), ΔG(excit.);
2-(2-methoxyphenyl)iminothiazolidine hydrochloride
128398-33-4

2-(2-methoxyphenyl)iminothiazolidine hydrochloride

phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

N-(2-methoxyphenyl)-N'-phenyl-N-(2-thiazolin-2-yl)thiourea
128398-35-6

N-(2-methoxyphenyl)-N'-phenyl-N-(2-thiazolin-2-yl)thiourea

Conditions
ConditionsYield
With pyridine for 24h; Ambient temperature;100%
phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

proazaphosphatrane
120666-13-9

proazaphosphatrane

C16H26N5PS

C16H26N5PS

Conditions
ConditionsYield
In diethyl ether for 0.0833333h;100%
phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

proazaphosphatrane
120666-13-9

proazaphosphatrane

C16H26N5PS

C16H26N5PS

Conditions
ConditionsYield
In diethyl ether for 0.0833333h;100%
phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

[1-(2-aminoethyl)-3-aminopropyl]trimethoxysilane
1760-24-3

[1-(2-aminoethyl)-3-aminopropyl]trimethoxysilane

C22H32N4O3S2Si

C22H32N4O3S2Si

Conditions
ConditionsYield
In ethanol for 0.25h; Heating;100%
phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

3-(N-Phenylthiocarbamoyl)-8-methyl-2,3,3a,4,5,6-hexahydro-1H-pyrazino<3,2,1-j,k>carbazole
102269-32-9

3-(N-Phenylthiocarbamoyl)-8-methyl-2,3,3a,4,5,6-hexahydro-1H-pyrazino<3,2,1-j,k>carbazole

Conditions
ConditionsYield
In benzene for 0.5h; Heating;100%
phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

(1R,2R)-(+)-N,N'-dimethyl-1,2-diphenyl-ethylenediamine
118628-68-5

(1R,2R)-(+)-N,N'-dimethyl-1,2-diphenyl-ethylenediamine

((4R,5R)-1,3-Dimethyl-4,5-diphenyl-imidazolidin-2-ylidene)-phenyl-amine

((4R,5R)-1,3-Dimethyl-4,5-diphenyl-imidazolidin-2-ylidene)-phenyl-amine

Conditions
ConditionsYield
In dichloromethane Ambient temperature;100%
Dimethylallene
598-25-4

Dimethylallene

phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

C12H12NS(1-)*Li(1+)

C12H12NS(1-)*Li(1+)

Conditions
ConditionsYield
Stage #1: Dimethylallene With n-butyllithium In tetrahydrofuran; hexane at -60 - -30℃; for 0.833333h; Metallation;
Stage #2: phenyl isothiocyanate In tetrahydrofuran; hexane at -100 - -70℃; for 0.25h; Addition;
100%
(R,R)-1,2-diphenylethylenediamine
35132-20-8

(R,R)-1,2-diphenylethylenediamine

phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

1,1'-((1R,2R)-1,2-diphenylethane-1,2-diyl)bis(3-phenylthiourea)

1,1'-((1R,2R)-1,2-diphenylethane-1,2-diyl)bis(3-phenylthiourea)

Conditions
ConditionsYield
In dichloromethane at 20℃;100%
In dichloromethane at 20℃;
phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

4-benzylamino-2-phenyl-2-oxazoline
203444-38-6

4-benzylamino-2-phenyl-2-oxazoline

4-(1-benzyl-3-phenyl)thioureido-2-phenyl-2-oxazoline
586953-02-8

4-(1-benzyl-3-phenyl)thioureido-2-phenyl-2-oxazoline

Conditions
ConditionsYield
In diethyl ether at 20℃; for 1h;100%
In diethyl ether at 20℃; for 1h;92%
(1R,3R)-1-(3-hydroxyphenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid
869304-06-3

(1R,3R)-1-(3-hydroxyphenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid

phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

(5R,11aS)-5-(3-hydroxyphenyl)-2-phenyl-3-thioxo-6H-1,2,3,5,11,11a-hexahydro-imidazo[1,5-b]-β-carbolin-1-one

(5R,11aS)-5-(3-hydroxyphenyl)-2-phenyl-3-thioxo-6H-1,2,3,5,11,11a-hexahydro-imidazo[1,5-b]-β-carbolin-1-one

Conditions
ConditionsYield
In dimethyl sulfoxide; acetone Heating;100%

103-72-0Relevant articles and documents

A facile synthesis of aryl isothiocyanates from arylamines

Li, Zhibin,Qian, Xuhong,Liu, Zhi,Li, Zhong,Song, Gonghua

, p. 571 - 573 (2000)

-

Triphosgene: An efficient catalyst for synthesis of isothiocyanates

Chaskar,Yewale,Bhagat,Langi

, p. 1972 - 1975 (2008)

Isothiocyanates are bioactive molecules that show various biological activities such as antifungal and anathematic activities. They play a vital role in the synthesis of various heterocyclic compounds. Various isothiocyanates were prepared in good to high yield using triphosgene. Copyright Taylor & Francis Group, LLC.

Dynamic Ureas with Fast and pH-Independent Hydrolytic Kinetics

Cai, Kaimin,Ying, Hanze,Cheng, Jianjun

, p. 7345 - 7348 (2018)

Low cost, high performance hydrolysable polymers are of great importance in biomedical applications and materials industries. While many applications require materials to have a degradation profile insensitive to external pH to achieve consistent release profiles under varying conditions, hydrolysable chemistry techniques developed so far have pH-dependent hydrolytic kinetics. This work reports the design and synthesis of a new type of hydrolysable polymer that has identical hydrolysis kinetics from pH 3 to 11. The unprecedented pH independent hydrolytic kinetics of the aryl ureas were shown to be related to the dynamic bond dissociation controlled hydrolysis mechanism; the resulting hindered poly(aryl urea) can be degraded with a hydrolysis half-life of 10 min in solution. More importantly, these fast degradable hindered aromatic polyureas can be easily prepared by addition polymerization from commercially available monomers and are resistant to hydrolysis in solid form for months under ambient storage conditions. The combined features of good stability in solid state and fast hydrolysis at various pH values is unprecedented in polyurea material, and will have implications for materials design and applications, such as sacrificial coatings and biomaterials.

A metal-free synthesis of 2-aminobenzothiazoles through aminyl radical addition to aryl isothiocyanates

He, Yimiao,Li, Jing,Luo, Shuang,Huang, Jinbo,Zhu, Qiang

, p. 8444 - 8447 (2016)

A convenient synthesis of 2-aminobenzothiazoles, starting from aryl isothiocyanates and formamides under metal-free conditions, is described. Various secondary and tertiary amine- and even α-amino acid-derived formamides can be used as amino sources in this process. Mechanistic studies suggest that the reaction is initiated by decarbonylative aminyl radical formation in the presence of n-Bu4NI and TBHP, followed by aminyl radical addition to isothiocyanates and cyclization via sulfur centred radical intermediates.

Synthesis of Multifunctional 2-Aminobenzimidazoles on DNA via Iodine-Promoted Cyclization

Fan, Jing,Feng, Jing,Franklin, G. Joseph,Lancia, David R.,Li, Jin,Liu, Guansai,O'connell, Jonathan,Peng, Ting,Su, Liqiang,Wan, Jinqiao

, (2020)

2-Aminobenzimidazole cores are among the most common structural components in medicinal chemistry and can be found in many biologically active molecules. Herein, we report a mild protocol for the synthesis of multifunctional 2-aminobenzimidazoles on-DNA with broad substrate scopes. The reaction conditions expand our ability to design and synthesize 2-aminobenzimidazole core-focused DNA-encoded libraries.

Synthesis of isothiocyanates by reaction of amides with carbon disulfide in the presence of solid potassium carbonate/sodium hydroxide mixture

Albanese,Penso

, p. 1001 - 1002 (1991)

Readily available N-monosubstituted trifluoroacetamides are transformed into isothiocyanates in good yield by reaction, at room temperature, with carbon disulfide in acetonitrile in the presence of anhydrous sodium hydroxide/potassium carbonate basic mixture.

-

Sakai et al.

, p. 2981 (1975)

-

A convenient synthesis of isothiocyanates from primary nitroalkanes

Kim,Song,Ryu

, p. 1101 - 1105 (1994)

The reaction of primary nitroalkanes with thiourea in the presence of 4-chlorophenyl isocyanate and a catalytic amount of triethylamine in benzene afforded isothiocyanates in moderate yields.

Design, synthesis and in vitro evaluation of novel ursolic acid derivatives as potential anticancer agents

Hua, Shi-Xian,Huang, Ri-Zhen,Ye, Man-Yi,Pan, Ying-Ming,Yao, Gui-Yang,Zhang, Ye,Wang, Heng-Shan

, p. 435 - 452 (2015)

A series of novel ursolic acid (UA) derivatives modified at the C-3 and the C-28 positions were designed and synthesized in an attempt to develop potential antitumor agents. The in vitro cytotoxicity were evaluated against five cancer cell lines (MGC-803, HCT-116, T24, HepG2 and A549 cell lines) and a normal cell (HL-7702) by MTT assay. The screening results indicated that some of these target compounds displayed moderate to high levels of antiproliferative activities compared with ursolic acid and 5-fluorouracil (5-FU), and exhibited much lower cytotoxicity than 5-FU, indicating that the targeted compounds had selective and significant effect on the cell lines. The induction of apoptosis and affects on the cell cycle distribution of compound 6r were investigated by acridine orange/ethidium bromide staining, Hoechst 33258 staining, JC-1 mitochondrial membrane potential staining and flow cytometry, which revealed that the antitumor activity of 6r was possibly achieved through the induction of cell apoptosis by G1 cell-cycle arrest. Western blot and qRT-PCR (quantitative real-time PCR) experiments demonstrated that compound 6r may induce apoptosis through both of intrinsic and extrinsic apoptosis pathway.

A catalyst-free method for the synthesis of 1,4,2-dithiazoles from isothiocyanates and hydroxylamine triflic acid salts

An, Zhenyu,Liu, Yafeng,Ren, Yi,Wang, Ting,Yan, Rulong

, p. 6206 - 6209 (2021)

A catalyst-free method for the preparation of 1,4,2-dithiazoles is developed by reactions of isothiocyanates with hydroxylamine triflic acid salts. This reaction achieves C-S, C-N, and S-N bond formation, and a range of products are obtained in moderate to good yields. The obvious feature is using shelf-stable hydroxylamine triflic acid salts as a N source to synthesize heterocycles under mild conditions.

High-performance liquid chromatography-based method to evaluate kinetics of glucosinolate hydrolysis by Sinapis alba myrosinase

Vastenhout, Kayla J.,Tornberg, Ruthellen H.,Johnson, Amanda L.,Amolins, Michael W.,Mays, Jared R.

, p. 105 - 113 (2014)

Isothiocyanates (ITCs) are one of several hydrolysis products of glucosinolates, plant secondary metabolites that are substrates for the thioglucohydrolase myrosinase. Recent pursuits toward the development of synthetic non-natural ITCs have consequently led to an exploration of generating these compounds from non-natural glucosinolate precursors. Evaluation of the myrosinase-dependent conversion of select non-natural glucosinolates to non-natural ITCs cannot be accomplished using established ultraviolet-visible (UV-Vis) spectroscopic methods. To overcome this limitation, an alternative high-performance liquid chromatography (HPLC)-based analytical approach was developed where initial reaction velocities were generated from nonlinear reaction progress curves. Validation of this HPLC method was accomplished through parallel evaluation of three glucosinolates with UV-Vis methodology. The results of this study demonstrate that kinetic data are consistent between both analytical methods and that the tested glucosinolates respond similarly to both Michaelis-Menten and specific activity analyses. Consequently, this work resulted in the complete kinetic characterization of three glucosinolates with Sinapis alba myrosinase, with results that were consistent with previous reports.

Reactions of arenediazonium tetrafluoroborates with 1,4-bis(acryloyloxy)butane in the presence of thiocyanate ion

Gorbovoi,Baranovskii,Koval'skii,Grishchuk

, p. 1230 - 1232 (2002)

The first thiocyanatoarylation reaction with an unsaturated compound containing two isolated multiple bonds, 1,4-bis(acryloyloxy)butane, was effected. The reactions of 1,4-bis(acryloyloxy)butane with arenediazonium tetrafluoroborates occur in aqueous acet

Thiazolyl-thiadiazines as Beta Site Amyloid Precursor Protein Cleaving Enzyme-1 (BACE-1) Inhibitors and Anti-inflammatory Agents: Multitarget-Directed Ligands for the Efficient Management of Alzheimer's Disease

Sagar, Sneha R.,Singh, Devendra Pratap,Panchal, Nirupa B.,Das, Rajesh D.,Pandya, Dhaivat H.,Sudarsanam, Vasudevan,Nivsarkar, Manish,Vasu, Kamala K.

, p. 1663 - 1679 (2018)

Alzheimer's disease (AD) is associated with multiple neuropathological events including β-site amyloid precursor protein cleaving enzyme-1 (BACE-1) inhibition and neuronal inflammation, ensuing degeneracy, and death to neuronal cells. Targeting such a complex disease via a single target directed treatment was found to be inefficacious. Hence, with an intention to incorporate multiple therapeutic effects within a single molecule, multitarget-directed ligands (MTDLs) have been evolved. Herein, for the first time, we report the discovery of novel thiazolyl-thiadiazines that can serve as MTDLs as evident from the in vitro and in vivo studies. These MTDLs exhibited BACE-1 inhibition down to micromolar range, and results from the in vivo studies demonstrated efficient anti-inflammatory activity with inherent gastrointestinal safety. Moreover, compound 6d unveiled noteworthy antioxidant, antiamyloid, neuroprotective, and antiamnesic properties. Overall, results of the present study manifest the potential outcome of thiazolyl-thiadiazines for AD treatment.

A general synthesis of isothiocyanates from dithiocarbamates using claycop

Mesheram, Harashadas M.,Dale, Srinivas,Yadav

, p. 8743 - 8744 (1997)

A Convenient and simple synthesis of alkyl, aryl and amino acid isothiocyanates is described by the decomposition of ammonium dithiocarbamates using Claycop in mild conditions.

Discovery of boronic acid-based potent activators of tumor pyruvate kinase M2 and development of gastroretentive nanoformulation for oral dosing

Patle, Rajkumar,Shinde, Shital,Patel, Sagarkumar,Maheshwari, Rahul,Jariyal, Heena,Srivastava, Akshay,Chauhan, Neelam,Globisch, Christoph,Jain, Alok,Tekade, Rakesh K.,Shard, Amit

, (2021)

Several studies have established that cancer cells explicitly over-express the less active isoform of pyruvate kinase M2 (PKM2) is critical for tumorigenesis. The activation of PKM2 towards tetramer formation may increase affinity towards phosphoenolpyruvate (PEP) and avoidance of the Warburg effect. Herein, we describe the design, synthesis, and development of boronic acid-based molecules as activators of PKM2. The designed molecules were inspired by existing anticancer scaffolds and several fragments were assembled in the derivatives. 6a-6d were synthesized using a multi-step synthetic strategy in 55–70% yields, starting from cheap and readily available materials. The compounds were selectively cytotoxic to kill the cancerous cells at 80 nM, while they were non-toxic to the normal cells. The kinetic studies established the compounds as novel activators of PKM2 and (E/Z)-(4-(3-(2-((4-chlorophenyl)amino)-4-(dimethylamino)thiazol-5-yl)-2-(ethoxycarbonyl)-3-oxoprop-1-en-1-yl) phenyl)boronic acid (6c) emerged as the most potent derivative. 6c was further evaluated using various in silico tools to understand the molecular mechanism of tetramer formation. Docking studies revealed that 6c binds to the PKM2 dimer at the dimeric interface. Further to ascertain the binding site and mechanism of action, rigorous MD (molecular dynamics) simulations were undertaken, which led to the conclusion that 6c stabilizes the center of the dimeric interface that possibly promotes tetramer formation. We further planned to make a tablet of the developed molecule for oral delivery, but it was seriously impeded owing to poor aqueous solubility of 6c. To improve aqueous solubility and retain 6c at the lower gastrointestinal tract, thiolated chitosan-based nanoparticles (TCNPs) were prepared and further developed as tablet dosage form to retain anticancer potency in the excised goat colon. Our findings may provide a valuable pharmacological mechanism for understanding metabolic underpinnings that may aid in the clinical development of new anticancer agents targeting PKM2.

p-Aromatic Isothiocyanates: Synthesis and Anti Plant Pathogen Activity

Tang,Niu,Wang,Huo,Li,Luo,Cao

, p. 1252 - 1257 (2018)

In this study, a series of p-aromatic isothiocyanates are prepared by reacting p-aromatic amines with carbon disulphide and further treating with molecular iodine to yield corresponding isothiocyanate derivatives. The structures of newly synthesized compounds are confirmed by IR, NMR, and MS data. Activity of the products against plant pathogenic fungi and bacteria is tested and the structure-activity relationship is approached. p-Nitrophenyl isothiocyanate most efficiently inhibits Rhizoctonia solani and Erwinia carotovora. The order of seven aromatic isothiocyanates antifungicidal activity is following: p-nitrophenyl > p-methoxyphenyl > p-chlorophenyl > p-methylphenyl > p-ethylphenyl > phenyl > p-fluorophenyl. For antibacterial activity, the order was p-nitrophenyl > p-chlorophenyl > p-methylphenyl > p-ethylphenyl > p-fluorophenyl > phenyl > p-methoxyphenyl. The present study indicates that some of the compounds exhibit promising antimicrobial activity and can be used as an alternative to the traditional synthetic fungicides for controlling R. solani and E. carotovora.

New syntheses of aryl isothiocyanates from N-arylimino-1,2,3-dithiazoles

Besson, Thierry,Guillard, Jerome,Rees, Charles W.,Therisod, Michel

, p. 881 - 882 (1997)

Treatment of N-arylimino-1,2,3-dithiazoles 2 with ethylmagnesium bromide (2 equiv.) gives the corresponding aryl isothiocyanates 13, providing a very mild two-step conversion of ArNH2 into ArNCS avoiding hazardous reagents; alternatively the iminodithiazoles 2 can be converted into cyanothioformanilides 11 which rapidly give the same isothiocyanates with 1 equiv. of the Grignard reagent.

Synthesis of isothiocyanates using DMT/NMM/TsO? as a new desulfurization reagent

Janczewski, ?ukasz,Kolesińska, Beata,Kr?giel, Dorota

, (2021)

Thirty-three alkyl and aryl isothiocyanates, as well as isothiocyanate derivatives from esters of coded amino acids and from esters of unnatural amino acids (6-aminocaproic, 4-(aminomethyl)benzoic, and tranexamic acids), were synthesized with satisfactory or very good yields (25–97%). Synthesis was performed in a “one-pot”, two-step procedure, in the presence of organic base (Et3 N, DBU or NMM), and carbon disulfide via dithiocarbamates, with 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium toluene-4-sulfonate (DMT/NMM/TsO? ) as a desulfurization reagent. For the synthesis of aliphatic and aromatic isothiocyanates, reactions were carried out in a microwave reactor, and selected alkyl isothiocyanates were also synthesized in aqueous medium with high yields (72–96%). Isothiocyanate derivatives of L-and D-amino acid methyl esters were synthesized, under conditions without microwave radiation assistance, with low racemization (er 99 > 1), and their absolute configuration was confirmed by circular dichroism. Isothiocyanate derivatives of natural and unnatural amino acids were evaluated for antibacterial activity on E. coli and S. aureus bacterial strains, where the most active was ITC 9e.

-

Bullpitt,M.L.,Kitching,W.

, p. 321 - 328 (1972)

-

Synthesis and nematicidal activities of 1,2,3-benzotriazin-4-one derivatives containing thiourea and acylthiourea against Meloidogyne incognita

Chang, Yaning,Zhang, Jingwei,Chen, Xiulei,Li, Zhong,Xu, Xiaoyong

, p. 2641 - 2644 (2017)

Two series of novel 1,2,3-benzotriazin-4-one derivatives containing thiourea and acylthiourea were designed and synthesized. The bioassay results showed that most of the test compounds showed good nematicidal activity against M. incognita at the concentration of 10.0?mg?L?1 in vivo. The compounds A13, A17 and B3 showed excellent nematicidal activity on the second stage juveniles of the root-knot nematode with the inhibition rate of 51.3%, 58.3% and 51.3% at the concentration of 1.0?mg?L?1 respectively. It suggested that the structure of 1,2,3-benzotriazin-4-one derivatives containing thiourea and acylthiourea could be optimized further.

The Improved Phosphoramidate Route to Isothiocyanates

Olejniczak, Bogdan,Zwierzak, Andrzej

, p. 300 - 301 (1989)

Moderate yields of isothiocyanates prepared by the Wadsworth-Emmons approach can be essentially improved when the reaction is carried out in the presence of catalytic amounts of tetrabutylammonium bromide.

Efficient preparation of isothiocyanates from dithiocarbamates using bromineless brominating reagent

Yella, Ramesh,Ghosh, Harisadhan,Murru, Siva,Sahoo, Santosh K.,Patel, Bhisma K.

, p. 2083 - 2096 (2010)

For the first time, the crystal structure of a ditribromide reagent 1,1'-(ethane-1,2-diyl)dipyridinium bistribromide (EDPBT) has been determined. Utilizing this thiophilic bromineless brominating agent EDPBT, highly useful synthetic intermediates (alkyl and aryl isothiocyanates) have been achieved directly from dithiocarbamates. EDPBT can be easily prepared from readily available reagents. It has been used as a thiophilic reagent, and its thiophilicity dominates over its brominating ability for substrates amenable to bromination. This is a sustainable process for the preparation of isothiocyantes because the spent reagent can be recovered, regenerated, and reused. Copyright Taylor & Francis Group, LLC.

-

Sakai et al.

, p. 425,427 (1977)

-

A facile one-pot preparation of isothiocyanates from aldoximes

Kim, Jae Nyoung,Jung, Keum Shin,Lee, Hong Jung,Son, Ji Suk

, p. 1597 - 1598 (1997)

Isothiocyanates 2a-l were prepared in excellent yields in a one-pot reaction from aldoxime derivatives 1a-l by successive treatment of aldoxime with N-chlorosuccinimide (NCS), thiourea, and triethylamine. The use of HCl/DMF/Oxone system in the reaction instead of NCS was equally effective.

Diaryl-substituted thiosemicarbazone: A potent scaffold for the development of New Delhi metallo-β-lactamase-1 inhibitors

Li, Jia-Qi,Sun, Le-Yun,Jiang, Zhihui,Chen, Cheng,Gao, Han,Chigan, Jia-Zhu,Ding, Huan-Huan,Yang, Ke-Wu

, (2020/12/30)

The superbug infection caused by New Delhi metallo-β-lactamase (NDM-1) has become an emerging public health threat. Inhibition of NDM-1 has proven challenging due to its shuttling between pathogenic bacteria. A potent scaffold, diaryl-substituted thiosemicarbazone, was constructed and assayed with metallo-β-lactamases (MβLs). The obtained twenty-six molecules specifically inhibited NDM-1 with IC50 0.038–34.7 μM range (except 1e, 2e, and 3d), and 1c is the most potent inhibitor (IC50 = 0.038 μM). The structure-activity relationship of synthetic thiosemicarbazones revealed that the diaryl-substitutes, specifically 2-pyridine and 2-hydroxylbenzene improved inhibitory activities of the inhibitors. The thiosemicarbazones exhibited synergistic antimycobacterial actions against E. coli-NDM-1, resulted a 2–512-fold reduction in MIC of meropenem, while 1c restored 16–256-, 16-, and 2-fold activity of the antibiotic on clinical isolates ECs, K. pneumonia and P. aeruginosa harboring NDM-1, respectively. Also, mice experiments showed that 1c had a synergistic antibacterial ability with meropenem, reduced the bacterial load clinical isolate EC08 in the spleen and liver. This work provided a highly promising scaffold for the development of NDM-1 inhibitors.

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