28556-81-2

Basic information

• Product Name: 2,6-Dimethylphenyl isocyanate
• Synonyms: 2,6-DIMETHYLPHENYL ISOCYANATE;ISOCYANIC ACID 2,6-DIMETHYLPHENYL ESTER;2-isocyanato-1,3-dimethyl-benzen;2-Isocyanato-1,3-dimethylbenzene;Benzene, 2-isocyanato-1,3-dimethyl-;2,6-DIMETHYLPHENYL ISOCYANATE 99%;2,6-Xylyl isocyanate;Isocyanic acid, 2,6-xylyl ester
• CAS NO: 28556-81-2
• Molecular Formula: C₉H₉NO
• Molecular Weight: 147.17
• Product Categories: Phosgene Derivatives;Isocyanates;Nitrogen Compounds;Organic Building Blocks
• Mol File: 28556-81-2.mol
• Article Data: 21

Chemical Properties

• Boiling Point: 87-89 °C (12 mmHg)
• Flash Point: 86 °C
• Appearance: /
• Density: 1.057 g/mL at 25 °C(lit.)
• Refractive Index: 1.5346-1.5366
• Storage Temp.: 0-6°C
• Sensitive: Moisture Sensitive
• BRN: 742593
• CAS DataBase Reference: 2,6-Dimethylphenyl isocyanate(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-Dimethylphenyl isocyanate(28556-81-2)
• EPA Substance Registry System: 2,6-Dimethylphenyl isocyanate(28556-81-2)

Safety Data

• Hazard Codes: Xn
• Statements: 42-36/37/38-20/21/22
• Safety Statements: 45-36/37/39-26-23-37/39-28-27
• RIDADR: 2206
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 28556-81-2(Hazardous Substances Data)

Usage

Description

2,6-Dimethylphenyl isocyanate is a light yellow liquid with unique chemical properties that make it suitable for various applications in different industries. It is an organic compound characterized by its isocyanate functional group, which is highly reactive and forms the basis for its diverse uses.

Uses

Used in Chemical Synthesis:
2,6-Dimethylphenyl isocyanate is used as a key intermediate in the synthesis of various organic compounds. Its reactivity allows it to be employed in the preparation of derivatized β-cyclodextrins, which are used as chiral stationary phases in normal-phase liquid chromatography. This application is crucial for the separation and analysis of enantiomers in pharmaceutical and chemical industries.
Used in Coordination Chemistry:
In the field of coordination chemistry, 2,6-Dimethylphenyl isocyanate is used to synthesize tris(2,6-dimethylphenylimido)methylrhenium(VII) complexes. These complexes exhibit unique electronic and structural properties, making them valuable for studying metal-ligand interactions and potential applications in homogeneous catalysis.
Used in Pharmaceutical Industry:
2,6-Dimethylphenyl isocyanate is also utilized in the synthesis of 1-(2-isopropylphenyl)-3-(2,6-dimethylphenyl)urea, a compound with potential pharmaceutical applications. 2,6-Dimethylphenyl isocyanate's structure and properties make it a candidate for further development and testing in the search for new therapeutic agents.
Overall, 2,6-Dimethylphenyl isocyanate is a versatile compound with a wide range of applications across various industries, including chemical synthesis, coordination chemistry, and the pharmaceutical sector. Its unique properties and reactivity make it an essential component in the development of new materials and compounds with potential benefits for society.

InChI:InChI=1/C9H9NO/c1-7-4-3-5-8(2)9(7)10-6-11/h3-5H,1-2H3

Upstream product

• 35601-96-8 ethyl 2,6-dimethylphenylcarbamate 
• 75-44-5 phosgene 
• 87-62-7 2,6-dimethylaniline 
• 21436-98-6 2,6-dimethylaniline hydrochloride 
• 51608-99-2 N-2,6-Dimethylphenyl-N'-t-Bu,N'-isopropylharnstoff 
• 51609-00-8 N-Dimethylphenyl-N'-t-butyl,N'-3-pentylharnstoff 
• 51608-96-9 N-2,6-Dimethylphenyl-N',N'-di-sec-butylharnstoff 
• 51609-02-0 N-2,6-Dimethylphenyl-N'-2,4,4-trimethyl-2-pentyl,N'-isopropylharnstoff 
• 51609-01-9 N-Dimethylphenyl-N'-t-butyl,N'-cyclohexylharnstoff 
• 51608-97-0 N-2,6-Dimethylphenyl-N'-Cyclohexyl,N'-3-pentylharnstoff 
• 51608-98-1 N-2,6-Dimethylphenyl-N',N'-dicyclohexylharnstoff 
• 201230-82-2 carbon monoxide 
• 81-20-9 2,6-dimethylnitrobenzene 
• 154592-67-3 O-cyclododecyl-N-(2,6-dimethylphenyl)selenocarbamate 

Downstream Products

• 93142-50-8 (2,6-dimethyl-phenyl)-carbamic acid-(2-piperidino-ethyl ester) 
• 114254-87-4 N-(2,6-dimethyl-phenyl)-N'-(3-piperidino-propyl)-urea 
• 92700-32-8 (2,6-dimethyl-phenyl)-carbamic acid 2-morpholin-4-yl-ethyl ester 
• 96459-73-3 1-(2,6-dimethyl-phenylcarbamoyloxy)-2-phenylcarbamoyloxy-3-piperidino-propane 
• 108235-93-4 N-(2-diethylamino-ethyl)-N'-(2,6-dimethyl-phenyl)-urea 
• 25348-08-7 N,N'-di (2,6-dimethylphenyl) urea 
• 132465-60-2 N-(3-diethylamino-propyl)-N'-(2,6-dimethyl-phenyl)-urea 
• 35601-96-8 ethyl 2,6-dimethylphenylcarbamate 
• 131252-76-1 (2,6-dimethyl-phenyl)-thiocarbamic acid S-(2-diethylamino-ethyl ester) 
• 100129-63-3 N-(2-chloroethoxycarbonyl)-2,6-dimethylaniline 
• 2990-03-6 1-(2,6-dimethylphenyl)urea 
• 29848-34-8 (2,6-dimethyl-phenyl)-carbamic acid 2-morpholin-4-yl-cyclohexyl ester 
• 51608-98-1 N-2,6-Dimethylphenyl-N',N'-dicyclohexylharnstoff 
• 32608-38-1 (2,6-Dimethyl-phenyl)-carbamic acid 1-methyl-prop-2-ynyl ester 

Relevant articles and documents

2,6-DIMETHYLPHENYLNITRENE IN LOW-TEMPERATURE MATRICES

Photolysis of 2,6-dimethylphenyl azide on N2 matrices at 12K gives 2,6-dimethylphenylnitrene; in presence of CO, the nitrene forms the corresponding isocyanate, while on shorter wavelength irradiation, it undergoes an inefficient rearrangement to an azacycloheptatetraene.

Discovery of novel anti-angiogenesis agents. Part 7: Multitarget inhibitors of VEGFR-2, TIE-2 and EphB4

Herein, we embarked on a structural optimization campaign aiming at the discovery of second generation anti-angiogenesis agents with our previously reported BPS-7 as lead compound. A library of 27 compounds has been afforded based on the highly conserved ATP-binding pocket of VEGFR-2, Tie-2, and EphB4. Several title compounds exhibited simultaneous inhibitory effects against three angiogenic RTKs. These compounds with a ‘triplet’ inhibition profile have been identified as novel anti-angiogenic and anticancer agents. The representative VDAU11 displayed prominent anti-angiogenic and anticancer potency and could be considered as a candidate for further optimization. These results indicate that N-(pyridin-2-yl)acrylamide could serve as a novel hinge-binding group of triple inhibitors.

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.