102561-43-3

Basic information

• Product Name: 2-ISOPROPYL-6-METHYLPHENYL ISOCYANATE
• Synonyms: 2-ISOPROPYL-6-METHYLPHENYL ISOCYANATE;2-ISOPROPYL-6-METHYLPHENYL ISOCYANATE, 9 7%;Benzene, 2-isocyanato-1-methyl-3-(1-methylethyl)- (9CI);2-ISOPROPYL-6-METHYLPHENYL ISOCYANATE 97%;2-isocyanato-1-methyl-3-propan-2-ylbenzene;2-Isopropyl-6-methylphenyl isothiocyate, 95%
• CAS NO: 102561-43-3
• Molecular Formula: C11H13NO
• Molecular Weight: 175.23
• Product Categories: ISOPROPYL;ISOCYANATE;Isocyanates;Nitrogen Compounds;Organic Building Blocks
• Mol File: 102561-43-3.mol

Chemical Properties

• Boiling Point: 92 °C3 mm Hg(lit.)
• Flash Point: 218 °F
• Appearance: /
• Density: 1.008 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0326mmHg at 25°C
• Refractive Index: n20/D 1.526(lit.)
• Sensitive: Moisture Sensitive
• BRN: 6368845
• CAS DataBase Reference: 2-ISOPROPYL-6-METHYLPHENYL ISOCYANATE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-ISOPROPYL-6-METHYLPHENYL ISOCYANATE(102561-43-3)
• EPA Substance Registry System: 2-ISOPROPYL-6-METHYLPHENYL ISOCYANATE(102561-43-3)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38-42
• Safety Statements: 23-26-36
• RIDADR: UN 2206 6.1/PG 3
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 102561-43-3(Hazardous Substances Data)

Usage

Uses

Used in the Production of Polyurethane Foams and Coatings:
2-Isopropyl-6-methylphenyl isocyanate is used as a key ingredient in the production of polyurethane foams and coatings, contributing to their formation and performance characteristics.
Used in the Manufacturing of Adhesives, Sealants, and Elastomers:
In the adhesive, sealant, and elastomer industries, 2-Isopropyl-6-methylphenyl isocyanate is used as a critical component, enhancing the bonding and sealing properties of these materials.
Used as a Cross-linking Agent in Polyurethane Insulating Materials:
2-Isopropyl-6-methylphenyl isocyanate serves as an effective cross-linking agent in the production of polyurethane insulating materials, improving their thermal insulation properties and structural integrity.
It is crucial to handle 2-isopropyl-6-methylphenyl isocyanate with care, as it is a potent irritant to the skin, eyes, and respiratory system, and can cause allergic reactions in certain individuals. Adequate safety measures should be implemented during its handling and use to mitigate potential health risks.

InChI:InChI=1/C11H13NO/c1-8(2)10-6-4-5-9(3)11(10)12-7-13/h4-6,8H,1-3H3

Upstream product

• 32315-10-9 bis(trichloromethyl) carbonate 
• 5266-85-3 2-isopropyl-6-methylaniline 
• 75-44-5 phosgene 

Downstream Products

• 1209400-29-2 1-[3-cyano-7-(diethylamino)-2H-chromen-2-ylidene]-3-(2-isopropyl-6-methylphenyl)urea 

Relevant articles and documents

A Divergent Nickel-Catalyzed Synthesis of Quinazolinediones and Benzoxazinone Imines

During exploration of the nickel(0)-catalyzed reaction of isocyanates and isatoic anhydrides, it was found that changes in the substitution pattern of the isocyanate led to constitutionally isomeric quinazolinediones [quinazoline-2,4(1 H,3 H)-diones] or benzoxazinone imines [2-imino-1,2-dihydro-4 H -3,1-benzoxazin-4-ones]. Ligand and solvent screening experiments allowed for identification of conditions that could lead to each constitutional isomer in good to excellent levels of selectivity and yield. Comprehensive characterization of the previously poorly characterized benzoxazinone imines is also provided.

Structural optimization of a CXCR2-directed antagonist that indirectly inhibits γ-secretase and reduces Aβ

Amyloid β (Aβ), a key molecule in the pathogenesis of Alzheimer's disease (AD), is derived from the amyloid precursor protein (APP) by sequential proteolysis via β- and γ-secretases. Because of their role in generation of Aβ, these enzymes have emerged as important therapeutic targets for AD. In the case of γ-secretase, progress has been made towards designing potent inhibitors with suitable pharmacological profiles. Direct γ-secretase inhibitors are being evaluated in clinical trials and new strategies are being explored to block γ-secretase activity indirectly as well. In this regard, we have previously reported an indirect regulation of γ-secretase through antagonism of CXCR2, a G-protein coupled receptor (GPCR). We demonstrated that N-(2-hydroxy-4-nitrophenyl)-N′-(2-bromophenyl)urea (SB225002), a selective inhibitor of CXCR2 also plays a role in an indirect inhibition of γ-secretase. Furthermore, we reported a ～5-fold difference in the selective inhibition of APP versus Notch processing via γ-secretase following treatment with SB225002. Herein we describe the synthesis and optimization of SB225002. By determination of the structure-activity relationship (SAR), we derived small molecules that inhibit Aβ40 production with IC50 values in the sub-micromolar range in a cell-based assay and also validated the potential of CXCR2 as a new target for therapeutic intervention in AD.