3320-86-3

Basic information

• Product Name: 2-NITROPHENYL ISOCYANATE
• Synonyms: 1-isocyanato-2-nitro-benzen;1-Isocyanato-2-nitrobenzene;Benzene, 1-isocyanato-2-nitro-;Isocyanic acid, o-nitrophenyl ester;2-NITROPHENYL ISOCYANATE;TIMTEC-BB SBB006627;O-NITROPHENYL ISOCYANATE;2-Isocyanatonitrobenzene
• CAS NO: 3320-86-3
• Molecular Formula: C₇H₄N₂O₃
• Molecular Weight: 164.12
• EINECS: 222-024-2
• Product Categories: Isocyanates;Phenyls & Phenyl-Het;Phenyls & Phenyl-Het;Nitrogen Compounds;Organic Building Blocks
• Mol File: 3320-86-3.mol
• Article Data: 15

Chemical Properties

• Melting Point: 40-41 °C(lit.)
• Boiling Point: 135-137 °C17 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Yellow/Crystalline Solid
• Density: 1.5018 (rough estimate)
• Refractive Index: 1.5300 (estimate)
• Storage Temp.: Refrigerator (+4°C)
• CAS DataBase Reference: 2-NITROPHENYL ISOCYANATE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-NITROPHENYL ISOCYANATE(3320-86-3)
• EPA Substance Registry System: 2-NITROPHENYL ISOCYANATE(3320-86-3)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-27-36/37/39
• RIDADR: 2206
• WGK Germany: 3
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 3320-86-3(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
2-Nitrophenyl isocyanate is used as a reagent in the synthesis of various organic compounds. Its reactivity allows it to participate in a wide range of chemical reactions, making it a versatile building block in organic chemistry.
Used in the Synthesis of Symmetrical Bis-2-Nitrophenylcarbodiimide:
2-Nitrophenyl isocyanate is specifically used in the synthesis of symmetrical bis-2-nitrophenylcarbodiimide through a dimerization reaction. 2-NITROPHENYL ISOCYANATE has potential applications in various fields, such as pharmaceuticals and materials science, due to its unique properties and reactivity.

InChI:InChI=1S/C7H4N2O3/c10-5-8-6-3-1-2-4-7(6)9(11)12/h1-4H

Upstream product

• 63451-02-5 (2-nitro-phenyl)-carbamoyl chloride 
• 75-44-5 phosgene 
• 88-74-4 2-nitro-aniline 
• 33348-83-3 2-nitro-benzoic acid bromoamide 
• 587-85-9 diphenylmercury(II) 
• 503-38-8 trichloromethyl chloroformate 
• 1134-10-7 2-nitrobenzoyl azide 
• 29091-49-4 (2-nitro-phenyl)-carbamic acid-(4-nitro-phenyl ester) 
• 606-26-8 o-nitrobenzohydrazide 
• 606-27-9 methyl 2-nitrobenzoate 
• 13725-30-9 methyl N-(2-nitrophenyl)carbamate 
• 610-14-0 2-nitrobenzyl chloride 
• 552-16-9 ortho-nitrobenzoic acid 
• 32315-10-9 bis(trichloromethyl) carbonate 

Downstream Products

• 107155-32-8 N-(4-chloro-2-methyl-[6]quinolyl)-N'-(2-nitro-phenyl)-urea 
• 130672-07-0 N-(6-amino-2-methyl-[4]quinolyl)-N'-(2-nitro-phenyl)-urea 
• 130672-05-8 N-(4-amino-2-methyl-[6]quinolyl)-N'-(2-nitro-phenyl)-urea 
• 101722-41-2 N-(4-methoxy-2-methyl-[6]quinolyl)-N'-(2-nitro-phenyl)-urea 
• 13725-30-9 methyl N-(2-nitrophenyl)carbamate 
• 4836-78-6 (2-nitro-phenyl)-carbamic acid-(4-chloro-but-2-ynyl ester) 
• 92700-70-4 (2-nitro-phenyl)-carbamic acid octyl ester 
• 22074-87-9 2-Nitro-phenylthiocarbamidsaeure-O-ethylester 
• 2621-84-3 N-(ethoxycarbonyl)-2-nitroaniline 
• 490-70-0 (2-nitro-phenyl)-carbamic acid-(2-fluoro-ethyl ester) 
• 91558-46-2 (2-nitro-phenyl)-carbamic acid pentyl ester 
• 93733-82-5 (2-nitro-phenyl)-carbamic acid phenethyl ester 
• 100616-61-3 3,3-diethoxy-acrylic acid-(2-nitro-anilide) 
• 13201-86-0 N-(2-nitrophenyl)-N'-(2'-nitrophenyl)urea 

Relevant articles and documents

Discovery of N-phenyl-(2,4-dihydroxypyrimidine-5-sulfonamido) phenylurea-based thymidylate synthase (TS) inhibitor as a novel multi-effects antitumor drugs with minimal toxicity

Thymidylate synthase (TS) is a hot target for tumor chemotherapy, and its inhibitors are an essential direction for anti-tumor drug research. To our knowledge, currently, there are no reported thymidylate synthase inhibitors that could inhibit cancer cell migration. Therefore, for optimal therapeutic purposes, combines our previous reports and findings, we hope to obtain a multi-effects inhibitor. This study according to the principle of flattening we designed and synthesized 18 of N-phenyl-(2,4-dihydroxypyrimidine-5-sulfonamido)phenyl urea derivatives as multi-effects inhibitors. The biological evaluation results showed that target compounds could significantly inhibit the hTS enzyme, BRaf kinase and EGFR kinase activity in vitro, and most of the compounds had excellent anti-cell viability for six cancer cell lines. Notably, the candidate compound L14e (IC50 = 0.67 μM) had the superior anti-cell viability and safety to A549 and H460 cells compared with pemetrexed. Further studies had shown that L14e could cause G1/S phase arrest then induce intrinsic apoptosis. Transwell, western blot, and tube formation results proved that L14e could inhibit the activation of the EGFR signaling pathway, then ultimately achieve the purpose of inhibiting cancer cell migration and angiogenesis in cancer tissues. Furthermore, in vivo pharmacology evaluations of L14e showed significant antitumor activity in A549 cells xenografts with minimal toxicity. All of these results demonstrated that the L14e has the potential for drug discovery as a multi-effects inhibitor and provides a new reference for clinical treatment of non-small cell lung cancer.

Design, synthesis and evaluation of 1,2-benzisothiazol-3-one derivatives as potent caspase-3 inhibitors

A number of 1,2-benzisothiazol-3-one derivatives were prepared through structural modification of the original compound from high-throughput screening. Some analogues (e.g., 6b, 6r, 6s and 6w) were identified as novel and potent caspase inhibitors with IC50 of nanomolar. Structure-activity relationship (SAR) studies for caspase-3 inhibition were evaluated in vitro. Molecular modeling studies provided further insight into the interaction of this class of compounds with activated caspase-3. The present small molecule caspase-3 inhibitor with novel structures different from structures of known caspase inhibitors revealed a new direction for therapeutic strategies directed against diseases involving abnormally up-regulated apoptosis.

A simple and efficient synthesis of diaryl ureas with reduction of the intermediate isocyanate by triethylamine

Thirty symmetrical diaryl urea derivatives were synthesised in moderate to excellent yields from arylamine and triphosgene with triethylamine as a reducing agent for the intermediate, isocyanate. It was significant that part of the products could be collected in almost quantitative yield without column chromatography. The procedure under mild reaction conditions was tolerant of a wide range of functional groups. The structures of the compounds were determined by NMR, MS and X-ray crystallographic analyses.

Novel and efficient synthesis of 4-substituted-1,2,4-triazolidine-3,5- diones from anilines

A simple and efficient three-step synthetic procedure for the preparation of 4-substituted phenyl derivatives of 1,2,4-triazolidindiones (urazoles), starting from anilines, has been developed. In this method, aniline derivatives were reacted with 4-nitrophenyl chloroformate to provide corresponding carbamate derivatives. In the second step, semicarbazide derivatives were prepared from these carbamates by reaction with ethyl carbazate. The cyclization reaction of corresponding semicarbazides furnished 1,2,4-triazolidindiones in high yields. Copyright Taylor & Francis Group, LLC.

Synthesis and hypoxic-cytotoxic activity of some 3-amino-1,2,4-benzotriazine-1,4-dioxide derivatives

A series of 3-amino-1,2,4-benzotriazine-1,4-dioxide derivatives 1 have been synthesized and evaluated for their cytotoxic activity in vitro against human leukemia cell lines: Molt-4, K562, HL60, human liver cancer cell Hep-G2, human prostate cancer cell PC-3 in hypoxia. Most of the compounds showed more potent activity than TPZ. Compounds 1i and 1m displayed encouraging superior activity against Molt-4 and HL-60 cell lines. Three potential derivatives received the test of the activity in hypoxia and in normoxia against Molt-4 and HL-60 cell lines and showed obvious hypoxia selectivity. Further mechanism study revealed that the cytotoxic activities of compounds 1i and 1k in Molt-4 cells might be mediated by modulation of p53 protein expression and mitochondrial membrane potential (ΔΨm).

Dihydro-benzo[b][1,4]diazepin-2-one derivatives

This invention relates to dihydro-benzo[b][1,4]diazepin-2-one derivatives of the formula wherein R1, R2, X and Y are as defined in the specification and R3 is a six-membered aromatic heterocycle containing 1 to 3 nitrogen atoms or a pyridine-N-oxide as further defined in the specification. The invention further relates to medicaments containing these compounds, a process for their preparation as well as their use for preparation of medicaments for the treatment or prevention of acute and/or chronic neurological disorders.

Dihydro-benzo [b][1,4]diazepin-2-one derivatives

This invention is a dihydro-benzo[b][1,4]diazepin-2-one derivative of the formula wherein R1, R2, R3, X and Y are as defined in the specification. The invention includes pharmaceutical compositions containing these compounds, a process for their preparation, their use in preparation of pharmaceutical compositions and administration of an effective amount of the compounds for the treatment or prevention of acute and/or chronic neurological disorders to a patient in need of such treatment.

Dihydro-benzo [b] [1,4] diazepin-2-one derivatives

This invention is a dihydro-benzo [b] [1,4] diazepin-2-one derivative of the formula wherein R1, R2, R3 and Y are as defined in the specification. The invention includes pharmaceutical compositions containing these compounds, a process for their preparation and a method of treatment or prevention of acute and/or chronic neurological disorders by administering an effective amount of the compound of formula I or a pharmaceuticall acceptable salt thereof.

Antithrombotic agents

This application relates to a compound of formula (I), a pharmaceutically acceptable salt of the compound, or a prodrug thereof, as defined herein, pharmaceutical compositions thereof, and its use as an inhibitor of factor Xa, as well as a process for its preparation and intermediates therefor.

5-HT2A receptor inverse agonists

Disclosed herein is a new class of pyrazole compounds which act at the 5HT2A receptors.