54132-76-2

Basic information

• Product Name: 3,5-DIMETHOXYPHENYL ISOCYANATE
• Synonyms: 3,5-DIMETHOXYPHENYL ISOCYANATE;3,5-Dimethoxyphenyl isocyanate, tech;1-isocyanato-3,5-dimethoxybenzene(SALTDATA: FREE);1,3-Dimethoxy-5-isocyanatobenzene;3,5-Dimethoxyphenyl isocyanate 98%
• CAS NO: 54132-76-2
• Molecular Formula: C₉H₉NO₃
• Molecular Weight: 179.17
• Product Categories: Isocyanates;Nitrogen Compounds;Organic Building Blocks
• Mol File: 54132-76-2.mol

Chemical Properties

• Melting Point: 33-36 °C(lit.)
• Boiling Point: 279.5 °C at 760 mmHg
• Flash Point: >230 °F
• Appearance: /
• Density: 1.1 g/cm³
• Vapor Pressure: 0.004mmHg at 25°C
• Refractive Index: 1.501
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 3,5-DIMETHOXYPHENYL ISOCYANATE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-DIMETHOXYPHENYL ISOCYANATE(54132-76-2)
• EPA Substance Registry System: 3,5-DIMETHOXYPHENYL ISOCYANATE(54132-76-2)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38-42
• Safety Statements: 26-36
• RIDADR: UN 3335
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 54132-76-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3,5-Dimethoxyphenyl isocyanate is used as a key intermediate for the synthesis of pharmaceutical compounds. Its reactivity allows for the formation of various biologically active molecules, which can be further developed into potential drugs for treating different medical conditions.
Used in Chemical Synthesis:
In the field of organic chemistry, 3,5-Dimethoxyphenyl isocyanate serves as a versatile building block for the creation of a wide range of organic compounds. Its isocyanate group can react with various nucleophiles, enabling the formation of diverse chemical structures with potential applications in various industries.
Used in Polymer Industry:
3,5-Dimethoxyphenyl isocyanate is used as a monomer in the production of polyurethanes and other polymeric materials. The isocyanate group can react with alcohols, amines, and water to form urethane and urea linkages, which are the basis for many polymers with diverse properties and applications, such as coatings, adhesives, and elastomers.
Used in Agrochemical Industry:
3,5-Dimethoxyphenyl isocyanate can be employed as a starting material for the synthesis of agrochemicals, such as pesticides and herbicides. Its reactivity and structural diversity make it a valuable component in the development of new and effective compounds for agricultural applications.
Used in Dye and Pigment Industry:
The aromatic structure and functional groups of 3,5-Dimethoxyphenyl isocyanate make it a suitable candidate for the synthesis of dyes and pigments. Its ability to form various chemical structures can lead to the creation of compounds with unique color properties and stability, which can be used in the production of inks, paints, and other coloring agents.

InChI:InChI=1/C9H9NO3/c1-12-8-3-7(10-6-11)4-9(5-8)13-2/h3-5H,1-2H3

Upstream product

• 51707-38-1 3,5-dimethoxy-benzoic acid hydrazide 
• 75996-26-8 azido(3,5-dimethoxyphenyl)methanone 
• 17213-57-9 3,5-dimethoxybenzoyl chloride 
• 67333-75-9 1-(3,5-dimethoxy-benzoyl)-1H-imidazole 
• 710311-79-8 N-hydroxy-3,5-dimethoxybenzamide 
• 2150-37-0 methyl 3,5-dimethoxybenzoate 
• 2150-44-9 1-carbomethoxy-3,5-dihydroxybenzene 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 10272-07-8 3.5-dimethoxyaniline 
• 75-44-5 phosgene 
• 99-10-5 3,5-Dihydroxybenzoic acid 
• 17275-82-0 ethyl 3,5-dimethoxybenzoate 
• 1132-21-4 3,5-dimethoxybenzoic acid 
• 503-38-8 trichloromethyl chloroformate 

Downstream Products

• 1101105-48-9 C₁₂H₁₁ClN₂O₃S 
• 118488-01-0 6-hydroxy-7-[(3,5-dimethoxyphenyl)ureylene]-4-methylthieno[3,2-c]pyridine 
• 118487-95-9 5-hydroxy-4-[(3,5-dimethoxyphenyl)ureylene]-7-methylthieno[2,3-c]pyridine 
• 1016261-68-9 3-(3,4,5-trimethoxyphenyl)prop-2-ynyl 3,5-dimethoxyphenylcarbamate 
• 1016989-03-9 N,N',N''(nitrilotri-2,1-ethanediyl)tris(N'-3,5-dimethoxyphenylurea) 
• 1086018-61-2 C₂₅H₂₉NO₅ 
• 1420471-39-1 allyl (3,5-dimethoxyphenyl)carbamate 

Relevant articles and documents

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The emergence of multidrug-resistant bacterial strains is particularly important in chronic pathologies such as cystic fibrosis (CF), in which persistent colonization and selection of resistant strains is favored by the frequent and repeated use of antibacterial agents. Staphylococcus aureus is a common pathogen in CF patients that has an associated increased multidrug resistance. In previous studies we demonstrated that the presence of a 4-alkylidene side chain directly linked to a β-lactam appeared to strengthen the potency against S. aureus, especially against methicillin-resistant S. aureus (MRSA) strains. In the present study, 21 new 4-alkylidene-β-lactams were synthesized and evaluated for antibacterial activity. We designed the new compounds to have aryl, benzyl, or phenethyl-carbamate groups on the C3 hydroxyethyl side chain. We found a correlation between biological activity and the nitrogen substituent of the carbamate group, and two phenethyl-carbamate β-lactams were shown to be valuable antibacterial agents against selected linezolid-resistant strains, with a minimum inhibitory concentrations of 2–4 mg L?1.

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An efficient, one-pot, N-methylimidazole (NMI) accelerated synthesis of aromatic and aliphatic carbamates via the Lossen rearrangement is reported. NMI is a catalyst for the conversion of isocyanate intermediates to the carbamates. Moreover, the utility of arylsulfonyl chloride in combination with NMI minimizes the formation of often-observed hydroxamate-isocyanate dimers during the sequence. Under the present conditions, lowering of temperatures is also possible, enabling a mild protocol.

Synthesis of novel azo-resveratrol, azo-oxyresveratrol and their derivatives as potent tyrosinase inhibitors

Ten azo compounds including azo-resveratrol (5) and azo-oxyresveratrol (9) were synthesized using a modified Curtius rearrangement and diazotization followed by coupling reactions with various phenolic analogs. All synthesized compounds were evaluated for their mushroom tyrosinase inhibitory activity. Compounds 4 and 5 exhibited high tyrosinase inhibitory activity (56.25% and 72.75% at 50 μM, respectively). The results of mushroom tyrosinase inhibition assays indicate that the 4-hydroxyphenyl moiety is essential for high inhibition and that 3,5-dihydroxyphenyl and 3,5-dimethoxyphenyl derivatives are better for tyrosinase inhibition than 2,5-dimethoxyphenyl derivatives. Particularly, introduction of hydroxyl or methoxy group into the 4-hydroxyphenyl moiety diminished or significantly reduced mushroom tryosinase inhibition. Among the synthesized azo compounds, azo-resveratrol (5) showed the most potent mushroom tyrosinase inhibition with an IC50 value of IC50 = 36.28 ± 0.72 μM, comparable to that of resveratrol, a well-known tyrosinase inhibitor.

Discovery of 3-(2,6-Dichloro-3,5-dimethoxy-phenyl)-1-{6-[4-(4-ethyl- piperazin-1-yl)-phenylamino]-pyrimidin-4-yl}-1-methyl-urea (NVP-BGJ398), A potent and selective inhibitor of the fibroblast growth factor receptor family of receptor tyrosine kinase

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Synthesis of 4-benzyliden-2-oxazolidinone derivatives via gold-catalyzed intramolecular hydroamination

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Piperidine-containing histamine H3 receptor antagonists of the carbamate series: The influence of the additional ether functionality

Recently novel leads for histamine H3 receptor antagonists of the non-imidazole type have been described. As a continuation of this research eleven new carbamate derivatives possessing an additional ether functionality were prepared. The compounds were evaluated in vitro for their antagonist activity on isolated organs of guinea-pig (GP) H3 as well as H2, H1, and M3 receptors, respectively. All compounds investigated possessed moderate antagonist affinities at guinea-pig histamine H3 receptors (pA2 6.11-6.76). An ether functionality introduced in different places of the lipophilic part of carbamates differently influenced activity and selectivity toward H3, M3, and other histamine receptors tested.