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

Chemical Properties

light yellow liquid

Uses

2,6-Dimethylphenyl isocyanate has been used in the preparation of:derivatized β-cyclodextrins, used as chiral stationary phase in normal-phase liquid chromatographytris( 2,6-dimethylphenylimido)methylrhenium (VII)1-(2-isopropylphenyl)-3-(2,6-dimethylphenyl)urea

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 
• 87-62-7 2,6-dimethylaniline 
• 71395-14-7 tocainide hydrochloride 
• 2564-83-2 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical 
• 75-03-6 ethyl iodide 
• 591-50-4 iodobenzene 
• 75-30-9 2-iodo-propane 
• 26334-20-3 2,6-dimethylphenylazide 
• 75-44-5 phosgene 
• 124-38-9 carbon dioxide 
• 24424-99-5 di-tert-butyl dicarbonate 
• 154592-73-1 N-(2,6-dimethylphenyl)selenocarbamate of cholestanol 
• 154592-67-3 O-cyclododecyl-N-(2,6-dimethylphenyl)selenocarbamate 
• 201230-82-2 carbon monoxide 

Downstream Products

• 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 
• 25348-08-7 N,N'-di (2,6-dimethylphenyl) urea 
• 132465-60-2 N-(3-diethylamino-propyl)-N'-(2,6-dimethyl-phenyl)-urea 
• 51608-98-1 N-2,6-Dimethylphenyl-N',N'-dicyclohexylharnstoff 
• 97627-19-5 N-(2,6-dimethylphenyl)-N'-(3-pyridyl)-urea 
• 97627-20-8 N-(2,6-dimethylphenyl)-N′-(4-pyridinyl)urea 
• 124421-03-0 N-(2,6-dimethylphenyl)-N'-(2-pyridyl)urea 
• 130533-67-4 (2,6-Dimethyl-phenyl)-carbamic acid 2-piperidin-1-ylmethyl-phenyl ester 
• 55831-94-2 1-(2',6'-dimethylphenyl)-3-amidinourea 
• 221038-07-9 1-(chloromethyl)-2-isocyanato-3-methylbenzene 
• 857029-84-6 1-(4-chlorobenzoyl)-4-(2,6-dimethylphenyl)semicarbazide 

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.