3529-82-6

Basic information

• Product Name: 3-NITROPHENYL ISOTHIOCYANATE
• Synonyms: 1-isothiocyanato-3-nitro-benzen;1-isothiocyanato-3-nitrobenzene;isothiocyanicacid,m-nitrophenylester;3-NITROPHENYL ISOTHIOCYANATE;M-NITROPHENYL ISOTHIOCYANATE;3-Nitrophenyl isothiocyanate 98%;3-Nitrophenyl isothiocyate, 98%
• CAS NO: 3529-82-6
• Molecular Formula: C₇H₄N₂O₂S
• Molecular Weight: 180.18
• EINECS: -0
• Product Categories: Organic Building Blocks;Sulfur Compounds;Thiocyanates/Isothiocyanates
• Mol File: 3529-82-6.mol
• Article Data: 29

Chemical Properties

• Melting Point: 57-60 °C(lit.)
• Boiling Point: 277.5°C (rough estimate)
• Flash Point: 146°C
• Appearance: /
• Density: 1.4360 (rough estimate)
• Vapor Pressure: 0.000702mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• Storage Temp.: 2-8°C
• Water Solubility: 50.45mg/L(25 oC)
• Sensitive: Moisture Sensitive
• BRN: 2094061
• CAS DataBase Reference: 3-NITROPHENYL ISOTHIOCYANATE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-NITROPHENYL ISOTHIOCYANATE(3529-82-6)
• EPA Substance Registry System: 3-NITROPHENYL ISOTHIOCYANATE(3529-82-6)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 23-26-36/37/39-45
• RIDADR: UN 3261 8/PG 3
• WGK Germany: 3
• RTECS: NX9110000
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 3529-82-6(Hazardous Substances Data)

Usage

Description

3-Nitrophenyl isothiocyanate, also known as 1-isothiocyanato-3-nitrobenzene, is an organic building block that contains an isocyanate group. It has been evaluated for various physical properties, such as freezing point, boiling point, density, and refractive index. Its synthesis from 3-nitroaniline has been reported, and it is known for its enthalpy of vaporization at boiling point.

Uses

Used in Chemical Synthesis:
3-Nitrophenyl isothiocyanate is used as a synthetic building block for the creation of various chemical compounds. It plays a crucial role in the synthesis of different thiourea derivatives and other complex organic molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3-Nitrophenyl isothiocyanate is used as a key intermediate in the synthesis of potential therapeutic agents. It contributes to the development of novel drugs with diverse applications, including the treatment of various diseases and conditions.
Used in the Synthesis of Specific Compounds:
3-Nitrophenyl isothiocyanate is used as a reactant in the synthesis of the following thiourea derivatives:
N-[(3-chlorophenyl)methyl]-N′-(3-nitrophenyl)thiourea
N-[(5-chloro-2-methoxyphenyl)methyl]-N′-(3-nitrophenyl)thiourea
R/S-N-[6-chlorochroman-4-yl]-N′-(3-nitrophenyl)thiourea
These thiourea derivatives have potential applications in various fields, such as agriculture, pharmaceuticals, and materials science, due to their unique chemical properties and reactivity.
Used in the Synthesis of Complex Organic Molecules:
3-Nitrophenyl isothiocyanate is also used in the synthesis of complex organic molecules, such as 2-[(3-nitrophenyl)amino]naphtho[2,1-b]furo-5H-[3,2-d][1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one and 5-methyl-3-(3-nitrophenyl)-2-thiooxazolidin-4-one. These compounds may have potential applications in various industries, including pharmaceuticals, materials science, and chemical research.

InChI:InChI=1/C7H4N2O2S/c10-9(11)7-3-1-2-6(4-7)8-5-12/h1-4H

Upstream product

• 3320-87-4 isocyanic acid (3-nitro-phenyl) ester 
• 58655-17-7 m-nitrophenyldithiocarbamic acid triethylamine salt 
• 96989-50-3 di-2-pyridyl thionocarbonate 
• 99-09-2 3-nitro-aniline 
• 75-15-0 carbon disulfide 
• 280-57-9 1,4-diaza-bicyclo[2.2.2]octane 
• 1414781-31-9 C₇H₆N₂O₂S₂*C₆H₁₂N₂ 
• 86317-32-0 O-(4-methoxyphenyl) N-3-nitrophenylthioncarbamate 
• 13524-85-1 S-<3-Nitro-phenylcarbamoyl>-dithiophosphorsaeure-O,O'-diaethylester 
• 463-71-8 thiophosgene 
• 13140-66-4 1-(3-nitrophenyl)-3-phenylthiourea 
• 108-24-7 acetic anhydride 
• 13991-80-5 1,3-bis-(3-nitro-phenyl)-thiourea 
• 64-17-5 ethanol 

Downstream Products

• 53360-08-0 (3-nitro-phenyl)-thiocarbamic acid O-ethyl ester 
• 13991-80-5 1,3-bis-(3-nitro-phenyl)-thiourea 
• 7669-51-4 3-(2-methylphenyl)-1-(3-nitrophenyl)thiourea 
• 10324-48-8 α,α-Bis-(benzolsulfonyl)-thioessigsaeure-m-nitro-anilid 
• 99-09-2 3-nitro-aniline 
• 106740-63-0 4-methoxy-benzaldehyde-[4-(3-nitro-phenyl)-thiosemicarbazone] 
• 56913-89-4 1-(3-nitro-phenyl)-3-pyridin-3-ylmethyl-thiourea 
• 51718-86-6 N-(3-nitrophenyl)cyanamide 
• 1350545-09-3 8-(3-nitrophenylamino)-9-cyclopentyl-2-(4-(4-methylpiperazin-1-yl)phenylamino)-9H-purine 

Relevant articles and documents

4-PHENYL-N-(PHENYL)THIAZOL-2-AMINE DERIVATIVES AND RELATED COMPOUNDS AS ARYL HYDROCARBON RECEPTOR (AHR) AGONISTS FOR THE TREATMENT OF E.G. ANGIOGENESIS IMPLICATED OR INFLAMMATORY DISORDERS

4-phenyl-N-(phenyl)thiazol-2-amine and 4-(pyridin-3-yl)-N-( phenyl) thiazol-2-amine derivatives and the corresponding thiadiazole, thiophene, oxazole, oxadiazole, imidazole and triazole derivatives and related compounds as aryl hydrocarbon receptor (AHR) agonists for the treatment of angiogenesis implicated disorders, such as e.g. retinopathy, psoriasis, rheumatoid arthritis, obesity and cancer, or inflammatory disorders.

Design and synthesis of novel N-[3-(benzimidazol-2-ylamino)phenyl]amine and N-[3-(benzoxazol-2-ylamino)phenyl]amine derivatives as potential anticancer agents

In this contribution, we report the design, synthesis and cytotoxicity studies of a series of N-[3-(benzimidazol-2-yl-amino)phenyl]amine and N-[3-(benzoxazol-2-ylamino)phenyl]amine derivatives. In vitro cytotoxicity assay of 26 selected compounds was carried out at National Cancer Institute (NCI), USA. Out of them, compounds 10e (NSC D-762842/1) and 11s (NSC D-764942/1) have shown remarkable cytotoxicity with GI50 values ranging between “0.589–14.3?μM” and “0.276–12.3?μM,” respectively, in the representative nine subpanels of human tumor cell lines. Further, flow cytometry analysis demonstrated that compound 10e exerted cell cycle arrest at G2/M phase and showed dose-dependent enhancement in apoptosis in K-562 leukemia cancer cells.

Discovery and optimization of 4-oxo-2-thioxo-thiazolidinones as NOD-like receptor (NLR) family, pyrin domain-containing protein 3 (NLRP3) inhibitors

Aberrant activation of NLRP3 inflammasome is present in a subset of acute and chronic inflammatory diseases. The NLRP3 inflammasome has been recognized as an attractive therapeutic target for developing novel and specific anti-inflammatory inhibitors. Cellular structure-activity relationship-guided optimization resulted in the identification of 4-oxo-2-thioxo-thiazolidinone derivative 9 as a selective and direct small-molecule inhibitor of NLRP3 with IC50 of 2.4 μM, possessing favorable ex vivo and in vivo pharmacokinetic properties. Compound 9 may represent a lead for the development of anti-inflammatory therapeutics for treating NLRP3-driven diseases.