54029-45-7

Basic information

• Product Name: 2-Nitro-4-thiocyanatoaniline
• Synonyms: 2-Nitro-4-thiocyanatoaniline;Einecs 258-931-5;4-Thiocyanato-2-nitroaniline.;4-amino-3-nitrophenyl thiocyanate;2-NITRO-4-THIOCYANATOANILINE 96;o-Nitro-p-thiocyanoaniline;Thiocyanicacid4-amino-3-nitrophenylester;Thiocyanicacid4-amino-3-nitrop
• CAS NO: 54029-45-7
• Molecular Formula: C₇H₅N₃O₂S
• Molecular Weight: 195.2
• EINECS: 258-931-5
• Product Categories: Organic Building Blocks;Sulfur Compounds;Thiocyanates/Isothiocyanates;Amines;Aromatics;Sulfur & Selenium Compounds
• Mol File: 54029-45-7.mol

Chemical Properties

• Melting Point: 113 °C(lit.)
• Boiling Point: 378.9 ºC at 760 mmHg
• Flash Point: 183 ºC
• Appearance: /
• Density: 1.5 g/cm³
• Vapor Pressure: 6.07E-06mmHg at 25°C
• Refractive Index: 1.679
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: -2.09±0.10(Predicted)
• CAS DataBase Reference: 2-Nitro-4-thiocyanatoaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Nitro-4-thiocyanatoaniline(54029-45-7)
• EPA Substance Registry System: 2-Nitro-4-thiocyanatoaniline(54029-45-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 54029-45-7(Hazardous Substances Data)

Usage

Chemical Properties

Yellow Solid

Uses

Albendazole Impurity 5

InChI:InChI=1/C7H5N3O2S/c8-4-13-5-1-2-6(9)7(3-5)10(11)12/h1-3H,9H2

Upstream product

• 3321-94-6 N-(4-thiocyanatophenyl)acetamide 
• 54029-46-8 acetic acid-(2-nitro-4-thiocyanato-anilide) 
• 333-20-0 potassium thioacyanate 
• 88-74-4 2-nitro-aniline 
• 1147550-11-5 ammonium thiocyanate 
• 7726-95-6 bromine 
• 64-19-7 acetic acid 
• 2987-46-4 4-thiocyanatoaniline 
• 540-72-7 sodium thiocyanide 
• 5961-98-8 thiocyanatochloride 

Downstream Products

• 16671-77-5 3-nitrophenyl thiocyanate 
• 89642-54-6 4-chloro-3-nitro-phenyl thiocyanate 
• 98436-70-5 nitro-p-phenylene-bis thiocyanate 
• 408328-22-3 4-bromo-3-nitro-phenyl thiocyanate 
• 54394-37-5 1-amino-4-carbamoylthio-2-nitrobenzene 
• 80825-28-1 bis(4-amino-3-nitrophenyl) disulfide 
• 54393-89-4 1-amino-2-nitro-4-n-propylthiobenzene 
• 127923-96-0 4-amino-3,4'-dinitrodiphenyl sulfide 
• 101-59-7 4-amino-4'-nitrodiphenyl sulfide 
• 1223-31-0 bis(4-nitrophenyl)sulfide 
• 80983-47-7 4-amino-3-nitrobenzenethiol 
• 78212-93-8 bis(3,4-diaminophenyl) disulfide 
• 655247-00-0 3,4-diaminobenzenethiol 
• 57925-51-6 2-Nitro-4-(3-chloropropylthio)aniline 

Relevant articles and documents

Synthesis of 3,4-diaminobenzenethiol and its application in gold nanoparticle-based colorimetric determination of copper ions

An improved synthetic method for the synthesis of 3,4-diaminobenzenethiol is presented. The practical application of this reagent as a new ligand for gold nanoparticles for the rapid detection of Cu2+ in water is demonstrated. The method is shown to have high sensitivity and selectivity. Well-defined peaks, proportional to the concentration of the corresponding Cu2+, were observed from 0.5 μM to 2 μM, and the recovery was in the range of 92-109%. This method provides a facile route for Cu2+ analysis.

Preparation method of fenbendazole intermediate 2-nitro-4-phenylthioaniline

The invention relates to the technical field of veterinary drugs, and in particular, relates to a preparation method of fenbendazole intermediate 2-nitro-4-phenylthioaniline. The preparation method comprises the following steps: by taking o-nitroaniline and ammonium thiocyanate as raw materials and an organic solvent as a solvent of a reaction system, uniformly stirring and mixing, introducing chlorine, and filtering after the reaction of the raw materials is finished, so as to obtain 4-thiocyano-2-nitroaniline; taking 4-thiocyano-2-nitroaniline, adding sodium hydroxide and a reaction solvent,stirring and mixing, and filtering after the reaction is finished to obtain a sodium 4-amino-3-nitrothiophenol solution; carrying out a reaction on the sodium 4-amino-3-nitrothiophenol solution withbromobenzene under an alkaline condition, and after the reaction is finished, extracting to obtain the 2-nitro-4-phenylthioaniline. The preparation method is simple in process, the production cost isreduced, the production potential safety hazard can be reduced, the product yield is relatively high, and the environmental pollution is reduced.

Albendazole synthesis method

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.

Ratiometric SERS imaging and selective biosensing of nitric oxide in live cells based on trisoctahedral gold nanostructures

Herein, a ratiometric SERS probe was created for monitoring nitric oxide (NO) by designing a novel molecule, 3,4-diaminobenzene-thiol, and immobilizing this molecule onto trisoctahedral gold nanostructures with superior SERS capability. The established probe possessed good selectivity and biocompatibility, high sensitivity and accuracy, thus enabling imaging and biosensing of NO in live cells.

PROCESS FOR PREPARATION OF ALBENDAZOLE

The present invention discloses a novel, cost-effective process for preparation of a benzimidazole carbamates compound. Specifically, it relates to the process for the preparation of anti-parasite bulk drug albendazole. The process comprises a) thiocyanating 2-nitroaniline of formula VI with ammonium thiocyanated in presence of a halogen to obtain 2-nitro-4-thiocyanoaniline of formula V; b)propylating 2-nitro-4-thiocyanoaniline of formula V with propylbromide in presence of n-propanol and a base in absence of a phase transfer catalyst to obtain 4-propylthio-2-nitroaniline of formula III; C) reducing the nitro group of 4-propylthio-2-nitroaniline prepared in step b) by reacting an aqueous alkali metal sulphide or an alkaline metal sulphide to obtain 4-propylthio-o-phenylenediamine of formula II; and d)condensing 4-propylthio-o-phenylenediamine of formula II with alkali or alkaline earth metal salt of methylcyano carbamate in presence of an acid to form Albendazole of formula I.

A PROCESS FOR PREPARATION OF ALBENDAZOLE

The present invention discloses a novel, cost-effective process for preparation of a benzimidazole carbamates compound. Specifically, it relates to the process for the preparation of anti-parasite bulk drug albendazole. The process comprises a) thiocyanating 2-nitroaniline of formula VI with ammonium thiocyanated in presence of a halogen to obtain 2-nitro-4-thiocyanoaniline of formula V; b)propylating 2-nitro-4-thiocyanoaniline of formula V with propylbromide in presence of n-propanol and a base in absence of a phase transfer catalyst to obtain 4-propylthio-2-nitroaniline of formula III; C) reducing the nitro group of 4- propylthio-2-nitroaniline prepared in step b) by reacting an aqueous alkali metal sulphide or an alkaline metal sulphide to obtain 4-propylthio-o-phenylenediamine of formula II; and d)condensing 4-propylthio-o-phenylenediamine of formula II with alkali or alkaline earth metal salt of methylcyano carbamate in presence of an acid to form Albendazole of formula I.

Preparation of N-methoxycarbonyl-N'-[2-nitro-4(5)-propyl-thiophenyl]thiourea as prodrugs of albendazole

N-methoxycarbonyl-N'-(2-nitro-4-propylthiophenyl)thiourea and N-methoxycarbonyl-N'-(2-nitro-5-propylthiophenyl)thiourea, prodrugs of albendazole, have been synthesized. The biotransformation in rats, after oral administration of these prodrugs to albendazole and albendazole sulphoxide, is described.

Process for the preparation of 2-benzimidazole carbamates

A process for preparing 2-benzimidazole carbamate compounds by condensing an alkyl cyano carbamate with an o-phenylenediamine produced by reacting an ortho-nitro-aniline with thiocyanogen followed by replacement of the cyanide with an alkyl group and then converting the nitro group to the amine.

Certain thiazolidine and tetrahydrothiazine compounds

Benzene derivatives of the formula: STR1 wherein R1 is alkyl, R2 is a group --SR3, --SOR3, --SO2 R3 or --OR3, in which R3 is alkyl, cycloalkyl, alkenyl, alkynyl, aralkyl, aryl or cycloalkylalkyl, whose position on the benzene ring is either para to --NHCOAZ or para to the heterocyclo group, A is a C1-4 aliphatic hydrocarbon radical, B is a bivalent methylene or ethylene group, and Z is a primary, secondary or tertiary amino group, and acid addition salts and quaternary ammonium derivatives thereof, are new compounds useful as anthelmintics and antifungal agents.

Method of treating helminthiasis by parenteral administration of sulfoxide derivatives of benzimidazoles

A method is provided for treating or inhibiting helminthiasis by parenterally administering sulfoxide derivatives of benzimidazoles having the structure STR1 wherein R1 is lower alkyl or phenyl-lower alkyl, R2 and R3 may be the same or different and are hydrogen or lower alkyl, R4 is cycloalkyl, and m is 0 to 3, n is 0 to 3, m + n being ≤ 5. Pharmaceutical compositions for use in the above method are also provided.