18908-07-1

Basic information

• Product Name: 3-METHOXYPHENYL ISOCYANATE
• Synonyms: m-anisyl isocyanate;3-Anisyl isocyanate.;3-Methoxyphenyl isocyanate,99%;3-Methoxyphenyl isocyanate, 99% 25GR;3-Methoxyphenyl isocyanate, 99% 5GR;3-Isocyanatoanisole, 1-Isocyanato-3-methoxybenzene, 3-Isocyanatophenyl methyl ether;3-Methoxyphenyl isocyanate 99%;Benzene, 1-isocyanato-3-methoxy-
• CAS NO: 18908-07-1
• Molecular Formula: C₈H₇NO₂
• Molecular Weight: 149.15
• EINECS: 242-658-3
• Product Categories: Isocyanates;Nitrogen Compounds;Organic Building Blocks
• Mol File: 18908-07-1.mol

Chemical Properties

• Boiling Point: 94-95 °C10 mm Hg(lit.)
• Flash Point: 205 °F
• Appearance: Clear colorless to slightly pink/Liquid
• Density: 1.138 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.125mmHg at 25°C
• Refractive Index: n20/D 1.543(lit.)
• Storage Temp.: 0-10°C
• Sensitive: Moisture Sensitive
• BRN: 775986
• CAS DataBase Reference: 3-METHOXYPHENYL ISOCYANATE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-METHOXYPHENYL ISOCYANATE(18908-07-1)
• EPA Substance Registry System: 3-METHOXYPHENYL ISOCYANATE(18908-07-1)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38-42
• Safety Statements: 23-36/37/39-45
• RIDADR: UN 2206 6.1/PG 3
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 18908-07-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Methoxyphenyl isocyanate is used as a key intermediate for the synthesis of complex organic molecules, such as 1,3-bis(3-methoxyphenyl)-6-methyl-5-(trimethylsilyl)pyrimidine-2,4(1H,3H)-dione. 3-Methoxyphenyl isocyanate serves as a building block for the development of new pharmaceuticals, potentially contributing to the creation of novel drugs with improved therapeutic properties.
Used in Chemical Industry:
In the chemical industry, 3-Methoxyphenyl isocyanate is utilized as a reactive component in the production of various chemical products. Its reactivity and structural features make it a valuable asset in the synthesis of specialty chemicals, polymers, and other materials with specific applications in different sectors.
Overall, 3-Methoxyphenyl isocyanate is a crucial compound in the development of new pharmaceuticals and chemical products, showcasing its importance in both the pharmaceutical and chemical industries.

InChI:InChI=1/C8H7NO2/c1-11-8-4-2-3-7(5-8)9-6-10/h2-5H,1H3

Upstream product

• 3532-20-5 azido(3-methoxyphenyl)methanone 
• 75-44-5 phosgene 
• 536-90-3 m-Anisidine 
• 108716-30-9 benzyl (3-methoxyphenyl)carbamate 
• 141-43-5 ethanolamine 
• 51028-35-4 C₈H₈ClNO₂ 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 503-38-8 trichloromethyl chloroformate 
• 1711-05-3 m-anisoyl chloride 
• 586-38-9 3-Methoxybenzoic acid 
• 5813-86-5 m-methoxybenzamide 

Downstream Products

• 16460-28-9 N,N'-bis(3-methoxyphenyl)urea 
• 107771-96-0 (3-methoxy-phenyl)-carbamic acid-(2-diethylamino-ethyl ester) 
• 22541-10-2 C₁₀H₁₅N₃O₂ 
• 22546-34-5 C₉H₁₃N₃O₂ 
• 64393-01-7 1-Cyclopropyl-3-(3-methoxyphenyl)-harnstoff 
• 28386-47-2 (3-Methoxy-phenyl)-carbamic acid 5-chloro-2-(4-chloro-phenoxy)-phenyl ester 
• 28386-57-4 (3-Methoxy-phenyl)-carbamic acid 5-bromo-2-(4-chloro-phenoxy)-phenyl ester 
• 28395-96-2 (3-Methoxy-phenyl)-carbamic acid 5-chloro-2-(2,4-dichloro-phenoxy)-phenyl ester 
• 28386-67-6 (3-Methoxy-phenyl)-carbamic acid 4-bromo-5-chloro-2-(4-chloro-phenoxy)-phenyl ester 
• 28396-17-0 (3-Methoxy-phenyl)-carbamic acid 4-bromo-5-chloro-2-(2,4-dichloro-phenoxy)-phenyl ester 
• 23122-37-4 C₁₉H₁₈N₂O₅ 
• 34207-87-9 C₁₈H₁₉N₃O₅ 
• 34207-69-7 C₂₀H₂₃N₃O₅ 
• 34204-02-9 C₂₀H₂₃N₃O₅ 

Relevant articles and documents

Synthesis and biological evaluation of novel 4-(4-formamidophenylamino)-N-methylpicolinamide derivatives as potential antitumor agents

A novel series of 4-(4-formamidophenylamino)-N-methylpicolinamide derivatives were synthesized and evaluated against different tumor cell lines. Experiments in vitro showed that these derivatives could inhibit the proliferation of two kinds of human cancer cell lines (HepG2, HCT116) at low micromolar concentrations and the most potent analog 5q possessed broad-spectrum antiproliferative activity. Experiments in vivo demonstrated that 5q could effectively prolong the longevity of colon carcinoma-burdened mice and slow down the progression of cancer cells by suppression of angiogenesis and the induction of apoptosis and necrosis.

Synthesis and structure-activity relationship study of pyrrolidine-oxadiazoles as anthelmintics against Haemonchus contortus

Parasitic roundworms (nematodes) are significant pathogens of humans and animals and cause substantive socioeconomic losses due to the diseases that they cause. The control of nematodes in livestock animals relies heavily on the use of anthelmintic drugs. However, their extensive use has led to a widespread problem of drug resistance in these worms. Thus, the discovery and development of novel chemical entities for the treatment of parasitic worms of humans and animals is needed. Herein, we describe our medicinal chemistry optimization efforts of a phenotypic hit against Haemonchus contortus based on a pyrrolidine-oxadiazole scaffold. This led to the identification of compounds with potent inhibitory activities (IC50 = 0.78–22.4 μM) on the motility and development of parasitic stages of H. contortus, and which were found to be highly selective in a mammalian cell counter-screen. These compounds could be used as suitable chemical tools for drug target identification or as lead compounds for further optimization.

With Caspase - 3 inhibitory activity of benzisothiazole - 3 - one - 2 - amide compounds

The invention relates to a benzisothiazole-3-ketone-2-amide compound with Caspase-3 inhibiting activity. The benzisothiazole-3-ketone-2-amide compound has the Caspase-3 inhibiting activity, can be used for treating diseases mediated by Caspase-3, belongs to the field of pharmaceutical chemistry, and has a structural formula (I) as shown in the specification.

With anti-tumor effect of a quinazoline-urea derivative and its application (by machine translation)

The present invention relates to a of the general formula (II) anti-tumor function of said quinazoline-urea derivative and its application. The definition of the substituent in the general formula (II) in the specification. This invention, in order to SUO draw non-Buddhist nun and Geftinat compounds as the precursor, retention of SUO draw non-Buddhist nun the pharmocology-carbamido; at the same time, such as in reserved [...] EGFR-TKIs Geftinat, synthesis, and obtain a series of quinazoline-urea derivatives, by the in vitro activity tests, some compounds exhibit excellent anti-tumor activity, such derivatives have high research and utility value. (II). (by machine translation)

Discovery of novel VEGFR-2 inhibitors. Part 5: Exploration of diverse hinge-binding fragments via core-refining approach

Pathological angiogenesis plays a critical role in numerous diseases including malignancy. VEGFR-2 is the central regulators in angiogenesis and has become a promising target for anticancer drug design. We have identified a novel biphenyl-aryl urea incorporated with salicyladoxime (BPS-7) as potent VEGFR-2 inhibitor. As a continuation to our previous research, various aromatic-heterocyclic were introduced as hinge-binding fragment via a core-refining approach. Interestingly, many compounds exhibited comparable VEGFR-2 inhibition to Sorafenib. In particular, 12e and 12o displayed excellent VEGFR-2 inhibitory activity with IC50 values of 0.50 nM and 0.79 nM, respectively. Several title compounds showed considerable antiproliferative activity against A549 and SMMC-7721 cells. In addition, molecular docking was performed to rationalize the efficiency of the better compounds. These results will be instructive for further inhibitor design and optimization.

Novel VEGFR-2 kinase inhibitors identified by the back-to-front approach

We report a novel VEGFR-2 inhibitor, developed by the back-to-front approach. Docking experiments indicated that the 3-chloromethylphenylurea motif of the lead compound occupied the back pocket of VEGFR-2 kinase. An attempt was made to enhance the binding affinity of 1 by expanding the structure to access the front pocket using a triazole linker. A library of 1,4-(disubstituted)-1H-1, 2,3-triazoles were screened in silico, and one compound (VH02) was identified with an IC50 against VEGFR-2 of 0.56 μM. VH02 showed antiangiogenic effects, inhibiting tube formation in HUVEC cells (EA.hy926) at 0.3 μM, 13 times lower than its cytotoxic dose. These enzymatic and cellular activities suggest that VH02 has potential as a lead for further optimization.

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.

Structure-activity relationship studies of pyrazolo[3,4-d]pyrimidine derivatives leading to the discovery of a novel multikinase inhibitor that potently inhibits FLT3 and VEGFR2 and evaluation of its activity against acute myeloid leukemia in vitro and in vivo

We describe the structural optimization of a hit compound, 1-(4-(1H-pyrazolo[3,4-d]pyrimidin-4-ylamino)phenyl)-3-(3-methoxyphenyl)urea (1), which exhibits inhibitory activity but low potency against FLT3 and VEGFR2. A series of pyrazolo[3,4-d]pyrimidine derivatives were synthesized, and structure-activity relationship analysis using cell- and transgenic-zebrafish- based assays led to the discovery of a number of compounds that exhibited both high potency against FLT3-driven human acute myeloid leukemia (AML) MV4-11 cells and a considerable antiangiogenic effect in transgenic-zebrafish-based assays. The compound 1-(4-(1H-pyrazolo[3,4-d]pyrimidin -4-yloxy)phenyl)-3-(4-chloro-3- (trifluoromethyl)phenyl)urea (33), which exhibited the highest activity in preliminary in vivo anti-AML assays, was chosen for further anti-AML studies. The results demonstrated that compound 33 is a multikinase inhibitor that potently inhibits FLT3 and VEGFR2. In an MV4-11 xenograft mouse model, a once-daily dose of compound 33 at 10 mg/kg for 18 days led to complete tumor regression without obvious toxicity. Western blot and immunohistochemical analyses were performed to determine the mechanism of action of compound 33.

Novel leucine ureido derivatives as inhibitors of aminopeptidase N (APN)

Aminopeptidase N (APN/CD13) over expressed on tumor cells, plays a critical role in tumor invasion, metastasis, and tumor angiogenesis. Here we described the design, synthesis and preliminary activity studies of novel leucine ureido derivatives as aminopeptidase N (APN/CD13) inhibitors. The results showed that compound 8c had the most potent inhibitory activity against APN with the IC 50 value to 0.06 ± 0.041 μM, which could be used for further anticancer agent research.

(Tosylimino)phenyl-λ3-iodane as a reagent for the synthesis of methyl carbamates via hofmann rearrangement of aromatic and aliphatic carboxamides

A new, mild procedure for the Hofmann rearrangement of aromatic and aliphatic carboxamides using (tosylimino)phenyl-λ3-iodane, PhINTs, as a reagent is reported. Because of the mild reaction conditions, this method is particularly useful for the Hofmann rearrangement of substituted benzamides, which usually afford complex reaction mixtures with other hypervalent iodine oxidants. The mild reaction conditions and high selectivity in the reaction of carboxamides with PhINTs allow the isolation of the initially formed labile isocyanates or their subsequent conversion to stable carbamates by treatment with alcohols.