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66608-52-4 Usage

Uses

4-(Propylthio)-1,2-benzenediamine is a reactant used in the synthesis of the anthelmintic drug, albendazole. Albendazole Impurity 1.

Check Digit Verification of cas no

The CAS Registry Mumber 66608-52-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,6,6,0 and 8 respectively; the second part has 2 digits, 5 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 66608-52:
(7*6)+(6*6)+(5*6)+(4*0)+(3*8)+(2*5)+(1*2)=144
144 % 10 = 4
So 66608-52-4 is a valid CAS Registry Number.

66608-52-4SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-propylsulfanylbenzene-1,2-diamine

1.2 Other means of identification

Product number -
Other names 4-propylthio-o-phenylenediamine

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:66608-52-4 SDS

66608-52-4Synthetic route

1-amino-2-nitro-4-n-propylthiobenzene
54393-89-4

1-amino-2-nitro-4-n-propylthiobenzene

4-(propylthio)-1,2-phenylenediamine
66608-52-4

4-(propylthio)-1,2-phenylenediamine

Conditions
ConditionsYield
With sodium hydrogen sulfide In water at 30 - 60℃; for 5h;98.6%
With nickel-aluminum alloy; ammonium chloride In water at 80 - 90℃;96.7%
With Saccharomyces cerevisiae; methanol; sodium hydroxide In water59%
5-n-propylthio-2H-benzimidazole-2-spirocyclohexane
141421-20-7

5-n-propylthio-2H-benzimidazole-2-spirocyclohexane

4-(propylthio)-1,2-phenylenediamine
66608-52-4

4-(propylthio)-1,2-phenylenediamine

Conditions
ConditionsYield
With sodium dithionite In ethanol Heating;74%
With sodium dithionite In ethanol at 80℃; for 2h;74%
2-nitro-5-n-propylthioaniline
57780-75-3

2-nitro-5-n-propylthioaniline

4-(propylthio)-1,2-phenylenediamine
66608-52-4

4-(propylthio)-1,2-phenylenediamine

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethanol at 25℃;
With sodium dithionite In ethanol; water at 60℃;
With sodium sulfide In ethanol for 6h; Reflux;
5-chloro-2-nitroaniline
1635-61-6

5-chloro-2-nitroaniline

4-(propylthio)-1,2-phenylenediamine
66608-52-4

4-(propylthio)-1,2-phenylenediamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 98.5 percent / NaOH / ethane-1,2-diol; H2O / 5 h / Heating
2: H2 / Pd/C / ethanol / 25 °C
View Scheme
Multi-step reaction with 2 steps
1.1: potassium sulfide / ethanol; water / 70 - 78 °C
1.2: 2 h / Reflux
2.1: sodium sulfide / ethanol / 6 h / Reflux
View Scheme
5-chloro-2H-benzimidazole-2-spirocyclohexane
94526-10-0

5-chloro-2H-benzimidazole-2-spirocyclohexane

4-(propylthio)-1,2-phenylenediamine
66608-52-4

4-(propylthio)-1,2-phenylenediamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 60 percent / propan-1-ol / -10 - 0 °C
2: 74 percent / Na2S2O4 / aq. ethanol / Heating
View Scheme
spiro[2H-benzimidazole-2,1'-cyclohexane]
27429-80-7

spiro[2H-benzimidazole-2,1'-cyclohexane]

4-(propylthio)-1,2-phenylenediamine
66608-52-4

4-(propylthio)-1,2-phenylenediamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 60 percent / propan-1-ol / -10 - 0 °C
2: 74 percent / Na2S2O4 / aq. ethanol / Heating
View Scheme
2-nitro-aniline
88-74-4

2-nitro-aniline

4-(propylthio)-1,2-phenylenediamine
66608-52-4

4-(propylthio)-1,2-phenylenediamine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: chlorine / methanol / 7 h / 10 °C / Industry scale
2.1: sodium hydroxide / water; propan-1-ol / 35 °C / Industry scale
3.1: water; propan-1-ol / 40 - 60 °C / Industry scale
3.2: 60 °C
4.1: sodium hydrogen sulfide / methanol / 50 - 70 °C / Industry scale
View Scheme
Multi-step reaction with 3 steps
1: chlorine / methanol / 7 h / 10 °C / Large scale
2: sodium hydroxide; water / propan-1-ol / 35 - 60 °C / Large scale
3: sodium hydrogensulfide / methanol / 50 - 70 °C / Large scale
View Scheme
2-nitro-4-thiocyanoaniline
54029-45-7

2-nitro-4-thiocyanoaniline

4-(propylthio)-1,2-phenylenediamine
66608-52-4

4-(propylthio)-1,2-phenylenediamine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium hydroxide / water; propan-1-ol / 35 °C / Industry scale
2.1: water; propan-1-ol / 40 - 60 °C / Industry scale
2.2: 60 °C
3.1: sodium hydrogen sulfide / methanol / 50 - 70 °C / Industry scale
View Scheme
Multi-step reaction with 2 steps
1: sodium hydroxide; water / propan-1-ol / 35 - 60 °C / Large scale
2: sodium hydrogensulfide / methanol / 50 - 70 °C / Large scale
View Scheme
Multi-step reaction with 2 steps
1.1: sodium hydroxide / water / 1 h / 30 - 40 °C / Inert atmosphere
1.2: 2.5 h / 50 - 60 °C / Inert atmosphere
2.1: sodium hydroxide; iron(III) chloride; pyrographite; hydrazine / methanol / 3.5 h / Reflux
View Scheme
Multi-step reaction with 3 steps
1: sodium hydroxide / 1.5 h
2: hydrogenchloride / propan-1-ol; water / 100 °C / 9000.9 Torr / pH 3 / Autoclave
3: sodium hydrogen sulfide / water / 5 h / 30 - 60 °C
View Scheme
sodium 4-amino-3-nitrobenzenethiolate

sodium 4-amino-3-nitrobenzenethiolate

4-(propylthio)-1,2-phenylenediamine
66608-52-4

4-(propylthio)-1,2-phenylenediamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: water; propan-1-ol / 40 - 60 °C / Industry scale
1.2: 60 °C
2.1: sodium hydrogen sulfide / methanol / 50 - 70 °C / Industry scale
View Scheme
4-amino-3-nitrobenzenethiol
80983-47-7

4-amino-3-nitrobenzenethiol

4-(propylthio)-1,2-phenylenediamine
66608-52-4

4-(propylthio)-1,2-phenylenediamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogenchloride / propan-1-ol; water / 100 °C / 9000.9 Torr / pH 3 / Autoclave
2: sodium hydrogen sulfide / water / 5 h / 30 - 60 °C
View Scheme
methyl-N-cyano carbamate
21729-98-6

methyl-N-cyano carbamate

4-(propylthio)-1,2-phenylenediamine
66608-52-4

4-(propylthio)-1,2-phenylenediamine

albendazole
54965-21-8

albendazole

Conditions
ConditionsYield
In methanol at 65℃; for 3h;98.32%
4-(propylthio)-1,2-phenylenediamine
66608-52-4

4-(propylthio)-1,2-phenylenediamine

cyanogen chloride
506-77-4

cyanogen chloride

6-(propylthio)-1H-benzo[d]imidazol-2-amine

6-(propylthio)-1H-benzo[d]imidazol-2-amine

Conditions
ConditionsYield
With sodium hydroxide In methanol at 3 - 45℃; for 2h; pH=4; pH-value; Temperature;95.21%
4-(propylthio)-1,2-phenylenediamine
66608-52-4

4-(propylthio)-1,2-phenylenediamine

trifluoroacetic acid
76-05-1

trifluoroacetic acid

6-Propylsulfanyl-2-trifluoromethyl-1H-benzoimidazole
130772-97-3

6-Propylsulfanyl-2-trifluoromethyl-1H-benzoimidazole

Conditions
ConditionsYield
With hydrogenchloride Heating;85%
With hydrogenchloride Heating;60%
cyclohexanone
108-94-1

cyclohexanone

4-(propylthio)-1,2-phenylenediamine
66608-52-4

4-(propylthio)-1,2-phenylenediamine

1,3-dihydro-5-n-propylthio-2H-benzimidazole-2-spirocyclohexane
141421-17-2

1,3-dihydro-5-n-propylthio-2H-benzimidazole-2-spirocyclohexane

Conditions
ConditionsYield
at 50 - 60℃; for 0.5h;82%
4-(propylthio)-1,2-phenylenediamine
66608-52-4

4-(propylthio)-1,2-phenylenediamine

N-cyanodiphenylcarbonimidate
79463-77-7

N-cyanodiphenylcarbonimidate

5-propylthio-2-cyanoaminobenzimidazole
110821-26-6

5-propylthio-2-cyanoaminobenzimidazole

Conditions
ConditionsYield
In methanol for 6h; Heating;75%
trichloromethylphosphonyl dichloride
21510-59-8

trichloromethylphosphonyl dichloride

4-(propylthio)-1,2-phenylenediamine
66608-52-4

4-(propylthio)-1,2-phenylenediamine

5-propylsulfanyl-2-trichloromethyl-1,3-dihydro-benzo[1,3,2]diazaphosphole 2-oxide

5-propylsulfanyl-2-trichloromethyl-1,3-dihydro-benzo[1,3,2]diazaphosphole 2-oxide

Conditions
ConditionsYield
With triethylamine In toluene at 60 - 70℃; Condensation;68%
2,6-dimethylphenyl dichlorophosphoric acid
18350-98-6

2,6-dimethylphenyl dichlorophosphoric acid

4-(propylthio)-1,2-phenylenediamine
66608-52-4

4-(propylthio)-1,2-phenylenediamine

2-(2',6'-dimethylphenoxy)-2,3-dihydro-5-propyl-thio-1H-1,3,2-benzodiaza-phosphole 2-oxide

2-(2',6'-dimethylphenoxy)-2,3-dihydro-5-propyl-thio-1H-1,3,2-benzodiaza-phosphole 2-oxide

Conditions
ConditionsYield
With triethylamine In toluene at 60 - 70℃; Condensation;66%
4-(propylthio)-1,2-phenylenediamine
66608-52-4

4-(propylthio)-1,2-phenylenediamine

O-methyl-N-(methoxycarbonyl)-isourea
40943-37-1

O-methyl-N-(methoxycarbonyl)-isourea

Albendazole
54965-21-8

Albendazole

Conditions
ConditionsYield
With ethylenediaminetetraacetic acid; acetic acid In methanol at 110℃; for 5h; Inert atmosphere; Reflux;65.1%
4-(propylthio)-1,2-phenylenediamine
66608-52-4

4-(propylthio)-1,2-phenylenediamine

4-chlorophenylphosphorodichloridate
772-79-2

4-chlorophenylphosphorodichloridate

2-(4-chloro-phenoxy)-5-propylsulfanyl-1,3-dihydro-benzo[1,3,2]diazaphosphole 2-oxide

2-(4-chloro-phenoxy)-5-propylsulfanyl-1,3-dihydro-benzo[1,3,2]diazaphosphole 2-oxide

Conditions
ConditionsYield
With triethylamine In toluene at 60 - 70℃; Condensation;65%
4-(propylthio)-1,2-phenylenediamine
66608-52-4

4-(propylthio)-1,2-phenylenediamine

2-chlorophenyl dichlorophosphate
15074-54-1

2-chlorophenyl dichlorophosphate

2-(2-chloro-phenoxy)-5-propylsulfanyl-1,3-dihydro-benzo[1,3,2]diazaphosphole 2-oxide

2-(2-chloro-phenoxy)-5-propylsulfanyl-1,3-dihydro-benzo[1,3,2]diazaphosphole 2-oxide

Conditions
ConditionsYield
With triethylamine In toluene at 60 - 70℃; Condensation;63%
2,4-dichlorophenylphosphorodichloridate
19430-75-2

2,4-dichlorophenylphosphorodichloridate

4-(propylthio)-1,2-phenylenediamine
66608-52-4

4-(propylthio)-1,2-phenylenediamine

2-(2,4-dichloro-phenoxy)-5-propylsulfanyl-1,3-dihydro-benzo[1,3,2]diazaphosphole 2-oxide

2-(2,4-dichloro-phenoxy)-5-propylsulfanyl-1,3-dihydro-benzo[1,3,2]diazaphosphole 2-oxide

Conditions
ConditionsYield
With triethylamine In toluene at 60 - 70℃; Condensation;62%
4-(propylthio)-1,2-phenylenediamine
66608-52-4

4-(propylthio)-1,2-phenylenediamine

trifluoroacetic acid
76-05-1

trifluoroacetic acid

5-Propylsulfanyl-2-trifluoromethyl-1H-benzoimidazole

5-Propylsulfanyl-2-trifluoromethyl-1H-benzoimidazole

Conditions
ConditionsYield
With hydrogenchloride for 0.5h; Heating;60%
4-(propylthio)-1,2-phenylenediamine
66608-52-4

4-(propylthio)-1,2-phenylenediamine

O-phenyl phosphorodichloridate
770-12-7

O-phenyl phosphorodichloridate

2-phenoxy-5-propylsulfanyl-1,3-dihydro-benzo[1,3,2]diazaphosphole 2-oxide

2-phenoxy-5-propylsulfanyl-1,3-dihydro-benzo[1,3,2]diazaphosphole 2-oxide

Conditions
ConditionsYield
With triethylamine In toluene at 60 - 70℃; Condensation;60%
4-(propylthio)-1,2-phenylenediamine
66608-52-4

4-(propylthio)-1,2-phenylenediamine

4-methylphenyl phosphorodichloridate
878-17-1

4-methylphenyl phosphorodichloridate

5-propylsulfanyl-2-p-tolyloxy-1,3-dihydro-benzo[1,3,2]diazaphosphole 2-oxide

5-propylsulfanyl-2-p-tolyloxy-1,3-dihydro-benzo[1,3,2]diazaphosphole 2-oxide

Conditions
ConditionsYield
With triethylamine In toluene at 60 - 70℃; Condensation;59%
4-(propylthio)-1,2-phenylenediamine
66608-52-4

4-(propylthio)-1,2-phenylenediamine

2-methylphenyl phosphorodichloridate
6964-36-9

2-methylphenyl phosphorodichloridate

5-propylsulfanyl-2-o-tolyloxy-1,3-dihydro-benzo[1,3,2]diazaphosphole 2-oxide

5-propylsulfanyl-2-o-tolyloxy-1,3-dihydro-benzo[1,3,2]diazaphosphole 2-oxide

Conditions
ConditionsYield
With triethylamine In toluene at 60 - 70℃; Condensation;57%
4-(propylthio)-1,2-phenylenediamine
66608-52-4

4-(propylthio)-1,2-phenylenediamine

C8H9Cl2O2P
77014-57-4

C8H9Cl2O2P

2-(2,5-dimethyl-phenoxy)-5-propylsulfanyl-1,3-dihydro-benzo[1,3,2]diazaphosphole 2-oxide

2-(2,5-dimethyl-phenoxy)-5-propylsulfanyl-1,3-dihydro-benzo[1,3,2]diazaphosphole 2-oxide

Conditions
ConditionsYield
With triethylamine In toluene at 60 - 70℃; Condensation;55%
4-(propylthio)-1,2-phenylenediamine
66608-52-4

4-(propylthio)-1,2-phenylenediamine

m-Tolyl dichlorophosphate
940-18-1

m-Tolyl dichlorophosphate

5-propylsulfanyl-2-m-tolyloxy-1,3-dihydro-benzo[1,3,2]diazaphosphole 2-oxide

5-propylsulfanyl-2-m-tolyloxy-1,3-dihydro-benzo[1,3,2]diazaphosphole 2-oxide

Conditions
ConditionsYield
With triethylamine In toluene at 60 - 70℃; Condensation;52%
4-(propylthio)-1,2-phenylenediamine
66608-52-4

4-(propylthio)-1,2-phenylenediamine

1,3-bis(methoxycarbonyl)-S-methyl-isothiourea

1,3-bis(methoxycarbonyl)-S-methyl-isothiourea

albendazole
54965-21-8

albendazole

Conditions
ConditionsYield
In methanol Heating;44%
1,3-Dicarbomethoxy-S-methylisothiourea
34840-23-8

1,3-Dicarbomethoxy-S-methylisothiourea

4-(propylthio)-1,2-phenylenediamine
66608-52-4

4-(propylthio)-1,2-phenylenediamine

Albendazole
54965-21-8

Albendazole

Conditions
ConditionsYield
In methanol; water for 3h; Heating;44%
CYANAMID
420-04-2

CYANAMID

4-(propylthio)-1,2-phenylenediamine
66608-52-4

4-(propylthio)-1,2-phenylenediamine

methyl chloroformate
79-22-1

methyl chloroformate

albendazole
54965-21-8

albendazole

Conditions
ConditionsYield
In water; acetone Heating; pH 5-8.5;30%
CYANAMID
420-04-2

CYANAMID

4-(propylthio)-1,2-phenylenediamine
66608-52-4

4-(propylthio)-1,2-phenylenediamine

methyl chloroformate
79-22-1

methyl chloroformate

Albendazole
54965-21-8

Albendazole

Conditions
ConditionsYield
With sodium hydroxide In hydrogenchloride; water; acetone at 93℃;30%
diethyl phosphorisothiocyanatidate
6374-26-1

diethyl phosphorisothiocyanatidate

4-(propylthio)-1,2-phenylenediamine
66608-52-4

4-(propylthio)-1,2-phenylenediamine

4-Propylthio-N,N'-bis-(N-diethoxyphosphoryl-thiocarbamoyl)-1,2-phenylendiamin
66608-38-6

4-Propylthio-N,N'-bis-(N-diethoxyphosphoryl-thiocarbamoyl)-1,2-phenylendiamin

Conditions
ConditionsYield
In toluene
In chloroform
4-(propylthio)-1,2-phenylenediamine
66608-52-4

4-(propylthio)-1,2-phenylenediamine

6-(propane-1-sulfinyl)-2-trifluoromethyl-1H-benzoimidazole

6-(propane-1-sulfinyl)-2-trifluoromethyl-1H-benzoimidazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 85 percent / aq. HCl / Heating
2: 86 percent / m-CPBA / CHCl3 / 0.5 h / 5 °C
View Scheme
4-(propylthio)-1,2-phenylenediamine
66608-52-4

4-(propylthio)-1,2-phenylenediamine

5-n-propylthio-2H-benzimidazole-2-spirocyclohexane
141421-20-7

5-n-propylthio-2H-benzimidazole-2-spirocyclohexane

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 82 percent / 0.5 h / 50 - 60 °C
2: 82 percent / KMnO4, Bu4NBr / CH2Cl2; H2O
View Scheme
4-(propylthio)-1,2-phenylenediamine
66608-52-4

4-(propylthio)-1,2-phenylenediamine

5,6-dipropylthio-2H-benzimidazole-2-spirocyclohexane
141421-26-3

5,6-dipropylthio-2H-benzimidazole-2-spirocyclohexane

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 82 percent / 0.5 h / 50 - 60 °C
2: 82 percent / KMnO4, Bu4NBr / CH2Cl2; H2O
3: 22 percent / propan-1-ol / 24 h / Ambient temperature
View Scheme
Multi-step reaction with 3 steps
1: 82 percent / 0.5 h / 50 - 60 °C
2: 82 percent / KMnO4, Bu4NBr / CH2Cl2; H2O
3: 7 percent / propan-1-ol / 12 h / Ambient temperature
View Scheme
4-(propylthio)-1,2-phenylenediamine
66608-52-4

4-(propylthio)-1,2-phenylenediamine

4,6-dipropylthio-2H-benzimidazole-2-spirocyclohexane
141421-32-1

4,6-dipropylthio-2H-benzimidazole-2-spirocyclohexane

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 82 percent / 0.5 h / 50 - 60 °C
2: 82 percent / KMnO4, Bu4NBr / CH2Cl2; H2O
3: 11 percent / propan-1-ol / 24 h / Ambient temperature
View Scheme

66608-52-4Relevant articles and documents

Albendazole synthesis method

-

, (2019/03/25)

The invention discloses an albendazole synthesis method. The albendazole synthesis method includes reacting ammonium thiocyanate with chlorine gas in a lower alcohol solvent to obtain chlorothiocyanate, reacting ortho-nitroaniline with the chlorothiocyanate in the lower alcohol solvent to obtain 4-thiocyano-2-nitroaniline, reacting the 4-thiocyano-2-nitroaniline with a sodium hydroxide solution toobtain 4-sodium sulfonate-2-nitroaniline, performing hydrochloric acid acidification to obtain 4-mercapto-2-nitroaniline, subjecting the 4-mercapto-2-nitroaniline and propylene to Markovnikov addition reaction to obtain 4-propylthio-2-nitroaniline, and reacting 4-propylthio-o-phenylenediamine with methylcyanocarbamate to obtain albendazole. The albendazole synthesis method has the advantages thata novel synthetic route is applied to prepare the albendazole, the defects of high impurity quantity and low yield in the current production process are overcome, the chlorothiocyanate is prepared toserve as an intermediate and then reacts with the ortho-nitroaniline, and impurities can be avoided effectively; the propylene is introduced for the addition reaction, raw materials are clean and free from pollution, introduction of highly toxic sodium cyanide is avoided, the total yield is high, and the albendazole synthesis method has a good industrialization prospect.

4 - c sulfur preparation process of the manufacture of phenylenediamine

-

Paragraph 0017; 0021; 0022; 0023; 0024; 0025; 0026-0028, (2017/08/19)

The invention relates to a process for preparing 4-propylthio-o-phenylenediamine. According to the process provided by the invention, 4-propylthio-o-phenylenediamine is prepared from 2-nitro-4-propylthio phenylamine through being reduced by nickel aluminum alloy and an aqueous solution of ammonium chloride under the condition of heating. The process is high in yield, simple in operation and simple and convenient in after-treatment and has a relatively good application prospect.

Catalytic hydrogenation of sulfur-containing nitrobenzene over Pd/C catalysts: In situ sulfidation of Pd/C for the preparation of PdxSy catalysts

Zhang, Qunfeng,Xu, Wei,Li, Xiaonian,Jiang, Dahao,Xiang, Yizhi,Wang, Jianguo,Cen, Jie,Romano, Stephen,Ni, Jun

, p. 17 - 21 (2015/09/28)

The preparation of supported palladium sulfides catalysts has attracted much attention due to their good sulfur-resistant properties in the hydrogenation of sulfur-containing compounds. In this work, we unambiguously demonstrated that Pd/C catalyst could be in situ sulfided by organic sulfur-containing reactant molecules and the sulfidation was highly dependent on temperature. The in situ sulfidation of Pd/C catalyst was composed of a reaction of Pd with the sulfur derived from the cleavage of C-S bond of sulfur-containing reactant molecules, followed by a transformation to PdxSy at high temperatures (around 120 °C). The sulfided Pd/C catalyst could be used for at least 18 recycles without a significant loss in its activity during the hydrogenation of sulfur-containing nitrobenzene at 180 °C with 3 MPa H2, which could be attributed to the stable presence of Pd4S and Pd16S7.

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