31027-31-3

Basic information

• Product Name: 4-Isopropylphenyl isocyanate
• Synonyms: p-cumenylisocyanate;P-ISOPROPYL PHENYL ISOCYANATE;4-ISOPROPYLPHENYL ISOCYANATE;AKOS B028613;1-ISOCYANATO-4-ISOPROPYL-BENZENE;ART-CHEM-BB B028613;Benzene, 1-isocyanato-4-(1-methylethyl)- (9CI);p-Isopropylphenylisocyanat
• CAS NO: 31027-31-3
• Molecular Formula: C₁₀H₁₁NO
• Molecular Weight: 161.2
• EINECS: 250-439-9
• Product Categories: ISOPROPYL;Isocyanates;Nitrogen Compounds;Organic Building Blocks;organic chemical
• Mol File: 31027-31-3.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 85 °C4 mm Hg(lit.)
• Flash Point: 195 °F
• Appearance: clear colorless to yellow or orange liquid
• Density: 1.01 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.143mmHg at 25°C
• Refractive Index: n20/D 1.52(lit.)
• Water Solubility: decomposes
• Sensitive: Moisture Sensitive
• BRN: 2936403
• CAS DataBase Reference: 4-Isopropylphenyl isocyanate(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Isopropylphenyl isocyanate(31027-31-3)
• EPA Substance Registry System: 4-Isopropylphenyl isocyanate(31027-31-3)

Safety Data

• Hazard Codes: Xn,Xi,T+
• Statements: 20/21/22-36/37/38-42-34-26
• Safety Statements: 26-36-45-36/37/39-23
• RIDADR: UN 2206 6.1/PG 3
• WGK Germany: 1
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 31027-31-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H11NO/c1-8(2)9-3-5-10(6-4-9)11-7-12/h3-6,8H,1-2H3

Upstream product

• 98-82-8 Isopropylbenzene 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 5279-58-3 N-[4-(propan-2-yl)phenyl]formamide 
• 34123-59-6 N-(4-isopropylphenyl)-N',N'-dimethylurea 
• 99-88-7 4-Isopropylaniline 

Downstream Products

• 690636-76-1 1-(5-carboxypentyl)-3-(4-isopropylphenyl)-1-methylurea 
• 459412-95-4 butyl (4-isopropylphenyl)carbamate 
• 190726-95-5 N-(4-Isopropylphenyl)-N'-{4-[(6,7-dimethoxy-4-quinolinyl)oxy]phenyl}urea 
• 438047-41-7 S-4-[[4-(2-Propyl)phenylamino]carbonyl]oxybenzyl piperazine-1-thiocarboxylate hydrochloride 
• 449201-97-2 2-benzyloxy-3-(4-{2-[1-heptyl-3-(4-isopropyl-phenyl)-ureido]-ethyl}-phenyl)-propionic acid ethyl ester 
• 720708-48-5 4-{4-[3-(4-isopropyl-phenyl)-ureido]-phenyl}-1-(toluene-4-sulfonyl)-1H-pyrrole-2-carboxylic acid benzyl ester 
• 896210-41-6 C₁₇H₂₄N₂O₃ 

Relevant articles and documents

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.

Discovery of SP-96, the first non-ATP-competitive Aurora Kinase B inhibitor, for reduced myelosuppression

Aurora Kinase B is a serine-threonine kinase known to be overexpressed in several cancers, with no inhibitors approved for clinical use. Herein, we present the discovery and optimization of a series of novel quinazoline-based Aurora Kinase B inhibitors. The lead inhibitor SP-96 shows sub-nanomolar potency in Aurora B enzymatic assays (IC50 = 0.316 ± 0.031 nM). We identified the important pharmacophore features resulting in selectivity against receptor tyrosine kinases. Particularly, SP-96 shows >2000 fold selectivity against FLT3 and KIT which is important for normal hematopoiesis. This could diminish the adverse effect of neutropenia reported in the clinical trials of the Aurora B inhibitor Barasertib, which inhibits FLT3 and KIT in addition to Aurora B. Enzyme kinetics of SP-96 shows non-ATP-competitive inhibition which makes it a first-in-class inhibitor. Further, SP-96 shows selective growth inhibition in NCI60 screening, including inhibition of MDA-MD-468, a Triple Negative Breast Cancer cell line.

Synthesis of unsymmetrical phenylurea derivatives via oxidative cross coupling of aryl formamides with amines under metal-free conditions

A new synthetic approach for phenylurea derivatives involving the cross coupling of N-aryl formamides with amines through the formation of isocyanate intermediates in the presence of hypervalent iodine reagents is described.

Metal free oxidative coupling of aryl formamides with alcohols for the synthesis of carbamates

A direct transformation of N-aryl formamides to the corresponding carbamates via the formation of isocyanate intermediates is achieved in good yields using hypervalent iodine as an oxidant. This journal is

One-pot and novel route for the synthesis of 4-substituted-1,2,4- triazolidine-3,5-diones

The efficient and one-pot synthesis of 4-substituted-1,2,4-triazolidin-3,5- dione derivatives (4-substituted urazoles) via combination of triphosgene, substituted anilines, and ethyl carbazate in the presence of cesium carbonate is presented.

A simple and efficient synthesis of diaryl ureas with reduction of the intermediate isocyanate by triethylamine

Thirty symmetrical diaryl urea derivatives were synthesised in moderate to excellent yields from arylamine and triphosgene with triethylamine as a reducing agent for the intermediate, isocyanate. It was significant that part of the products could be collected in almost quantitative yield without column chromatography. The procedure under mild reaction conditions was tolerant of a wide range of functional groups. The structures of the compounds were determined by NMR, MS and X-ray crystallographic analyses.

1-Aryl-3-(1-acylpiperidin-4-yl)urea inhibitors of human and murine soluble epoxide hydrolase: Structure-activity relationships, pharmacokinetics, and reduction of inflammatory pain

1,3-Disubstituted ureas possessing a piperidyl moiety have been synthesized to investigate their structure-activity relationships as inhibitors of the human and murine soluble epoxide hydrolase (sEH). Oral administration of 13 1-aryl-3-(1-acylpiperidin-4-yl)urea inhibitors in mice revealed substantial improvements in pharmacokinetic parameters over previously reported 1-adamantylurea based inhibitors. For example, 1-(1-(cyclopropanecarbonyl) piperidin-4-yl)-3-(4-(trifluoromethoxy)phenyl)urea (52) showed a 7-fold increase in potency, a 65-fold increase in Cmax, and a 3300-fold increase in AUC over its adamantane analogue 1-(1-adamantyl)-3-(1-propionylpiperidin-4-yl) urea (2). This novel sEH inhibitor showed a 1000-fold increase in potency when compared to morphine by reducing hyperalgesia as measured by mechanical withdrawal threshold using the in vivo carrageenan induced inflammatory pain model.

Diazenedicarboxamides as inhibitors of D-alanine: D-alanine ligase (Ddl)

This invention belongs to the field of pharmaceutical chemistry and relates to new diazenedicarboxamides as inhibitors of D-alanine:D-alanine ligaze (Ddl), to procedures for their preparation and pharmaceutical preparations containing the same. Compounds of general formula I: and the pharmaceutically acceptable salts are described. The appropriate substituents are clearly presented in the body of the text and in claims.

Kinetics and mechanism of hydrolysis of phenylureas

The hydrolysis of phenylureas has been found to be affected by temperature, pH and buffer concentration. Kinetic evidence suggests that the formation of phenylisocyanate, the initial product in the title reaction, occurs via an intermediate zwitterion. Depending on pH and buffer concentrations, the zwitterion can be produced through three parallel routes: at low pH, specific acid-general base catalysis, followed by slow deprotonation of a nitrogen atom by a general base; at high pH, specific basic-general acid catalysis, followed by slow protonation of a N atom by a general acid; at intermediate pH the reaction proceeds through a proton switch promoted by buffers. Bifunctional acid-base buffers such as HCO3-/CO32-, H2PO42- and CH3COOH/CH3COO- are very efficient catalysts. At high buffer concentration, as well as at pH 12, the breakdown of the zwitterion is rate-determining. The results are discussed in relation to recently published papers reporting different pathways.