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

Uses

3-Nitrophenyl isothiocyanate may be used in the synthesis of 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.It may be used in the synthesis of the following thiourea derivatives:N-[(3-chlorophenyl)methyl]-N′-(3-nitrophenyl)thioureaN-[(5-chloro-2-methoxyphenyl)methyl]-N′-(3-nitrophenyl)thioureaR/S-N-[6-chlorochroman-4-yl]-N′-(3-nitrophenyl)thiourea

General Description

3-Nitrophenyl isothiocyanate, also known as 1-isothiocyanato-3-nitrobenzene, is an organic building block containing an isocyanate group. Its enthalpy of vaporization at boiling point has been reported. Some of its physical properties like freezing point, boiling point, density and refractive index have been evaluated. Its synthesis from 3-nitroaniline has been reported.

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

Upstream product

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

Downstream Products

• 108272-32-8 4-(3-nitro-phenyl)-1-(1-oxy-nicotinoyl)-thiosemicarbazide 
• 53360-08-0 (3-nitro-phenyl)-thiocarbamic acid O-ethyl ester 
• 13991-80-5 1,3-bis-(3-nitro-phenyl)-thiourea 
• 23893-22-3 [3-cyclohexyl-5-(3-nitro-anilino)-2-phenyl-2,3-dihydro-thiazol-4-yl]-(4-nitro-phenyl)-methanone 
• 62133-89-5 C₁₅H₂₂N₄O₂S 
• 3549-67-5 <3-Nitro-phenylthiocarbamoyl>-malonsaeure-diaethylester 
• 93677-75-9 C₁₄H₁₀Cl₂N₄O₃S 
• 124-38-9 carbon dioxide 
• 7783-06-4 hydrogen sulfide 
• 851886-25-4 1-(mesityl)-3-(3-nitrophenyl)thiourea 
• 56913-94-1 1-(3-nitro-phenyl)-3-pyridin-2-ylmethyl-thiourea 
• 56913-89-4 1-(3-nitro-phenyl)-3-pyridin-3-ylmethyl-thiourea 
• 1033590-78-1 C₁₄H₁₃N₃O₃S 
• 51718-86-6 N-(3-nitrophenyl)cyanamide 

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, synthesis and biological evaluation of novel 2,4-disubstituted quinazoline derivatives targeting H1975 cells via EGFR-PI3K signaling pathway

In order to find new and highly effective anti-tumor drugs with targeted therapeutic effects, a series of novel 4-aminoquinazoline derivatives containing N-phenylacetamide structure were designed, synthesized and evaluated for antitumor activity against four human cancer cell lines (H1975, PC-3, MDA-MB-231 and MGC-803) using MTT assay. The results showed that the compound 19e had the most potent antiproliferative activity against H1975, PC-3, MDA-MB-231 and MGC-803 cell lines. At the same time, compound 19e could significantly inhibit the colony formation and migration of H1975 cells. Compound 19e also arrested the H1975 cell cycle in the G1 phase and mediated cell apoptosis, promoted the accumulation of ROS in H1975 cells. Furthermore, compound 19e exerted antitumor effect in vitro by reducing the expression of anti-apoptotic protein Bcl-2 and increasing the pro-apoptotic protein Bax and p53. Mechanistically, compound 19e could significantly decreased the phosphorylation of EGFR and its downstream protein PI3K in H1975 cells. Which indicated that compound 19e targeted H1975 cell via interfering with EGFR-PI3K signaling pathway. Molecular docking showed that compound 19e could bind into the active pocket of EGFR. Those work suggested that compound 19e would have remarkable implications for further design of anti-tumor agents.

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.