5081-87-8

Basic information

• Product Name: 3-(2-CHLOROETHYL)-2,4(1H,3H)-QUINAZOLINEDIONE
• Synonyms: LABOTEST-BB LT00440822;3-(2-CHLOROETHYL)-1,2,3,4-TETRAHYDROQUINAZOLINE-2,4-DIONE;3-(2-CHLOROETHYL)-2,4(1H,3H)-QUINAZOLINEDIONE;TIMTEC-BB SBB003327;3-(2-chloroethyl)quinazoline-2,4(1H,3H)-dione;3-(2-chloroethyl)(1H,3H)quinazoline-2,4-dione;3-(2-CHLORO-ETHYL)-1H-QUINAZOLINE-2,4-DIONE;3-(2-CHLOROETHYL)-2,4(1H,3H)-QUINAZOLINE- DIONE 99%
• CAS NO: 5081-87-8
• Molecular Formula: C₁₀H₉ClN₂O₂
• Molecular Weight: 224.64
• EINECS: 225-795-3
• Product Categories: QuinazolinesHeterocyclic Building Blocks;Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Quinazolines
• Mol File: 5081-87-8.mol
• Article Data: 5

Chemical Properties

• Melting Point: 195-197 °C(lit.)
• Appearance: white to slightly grey crystalline powder
• Density: 1.358
• Vapor Pressure: 0-0Pa at 20-25℃
• Refractive Index: 1.5790 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 12?+-.0.20(Predicted)
• CAS DataBase Reference: 3-(2-CHLOROETHYL)-2,4(1H,3H)-QUINAZOLINEDIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(2-CHLOROETHYL)-2,4(1H,3H)-QUINAZOLINEDIONE(5081-87-8)
• EPA Substance Registry System: 3-(2-CHLOROETHYL)-2,4(1H,3H)-QUINAZOLINEDIONE(5081-87-8)

Safety Data

• Hazard Codes: T,Xn
• Statements: 45-23/24/25-22
• Safety Statements: 53-36/37/39-24/25-23
• WGK Germany: 3
• Hazardous Substances Data: 5081-87-8(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 5081-87-8 differently. You can refer to the following data:
1. 3-(2-Chloroethyl)quinazoline-2,4(1H,3H)-dione is used in preparation of Ketanserin.
2. 3-(2-Chloroethyl)-2,4(1H,3H)-quinazolinedione may be used in the synthesis of ketanserin .

General Description

3-(2-Chloroethyl)-2,4(1H,3H)-quinazolinedione is a quinazolinedione derivative. It has been synthesized by reacting ethyl-2-aminobenzoate with ethyl chloroformate and ethanol amine.

InChI:InChI=1/C10H9ClN2O2/c11-5-6-13-9(14)7-3-1-2-4-8(7)12-10(13)15/h1-4H,5-6H2,(H,12,15)

Upstream product

• 108890-73-9 ethyl 2-((ethoxycarbonyl)amino)benzoate 
• 87-25-2 2-ethoxycarbonylaniline 
• 1207-75-6 2,4-Dioxo-3-(2-hydroxyethyl)-1,2,3,4-tetrahydroquinazoline 
• 541-41-3 chloroformic acid ethyl ester 
• 141-43-5 ethanolamine 
• 134-20-3 2-carbomethoxyaniline 
• 118-92-3 anthranilic acid 
• 77093-94-8 2-(2-chloroethylamino)-4H-<3,1>benzoxazin-4-one hydrochloride 
• 28144-70-9 anthranilic acid amide 
• 1885-29-6 anthranilic acid nitrile 
• 52727-44-3 2,3-dihydro-5H-oxazolo<2,3-b>quinazolin-5-one 
• 28175-87-3 2-(2-chloroethyl ureido)benzamide 
• 13908-44-6 2-<3-(2-chloroethyl)ureido>benzoic acid 
• 83846-67-7 methyl 2-((ethoxycarbonyl)amino)benzoate 

Downstream Products

• 83846-83-7 ketanserin tartrate 
• 74050-98-9 ketanserine 

Relevant articles and documents

Ketoserin intermediate and preparation method of ketoserin

The invention discloses a preparation method of a ketoserin intermediate 2, 3-dihydro-5H-oxazolo[2, 3-B]quinazoline-5-ketone and a preparation method of ketoserin, and the reaction equation of the preparation method of the ketoserin intermediate 2, 3-dihydro-5H-oxazolo[2, 3-B]quinazoline-5-ketone is shown in the specification: in the reaction, sodium carbonate and acetonitrile are used, no catalyst is added, inorganic salt is removed through hot filtration after the reaction, filtrate is evaporated to dryness, acetonitrile is recycled, and an intermediate 04, namely the ketoserin intermediate2, 3-dihydro-5H-oxazolo[2, 3-B]quinazoline-5-ketone, is obtained. The method is simple and convenient to operate, lower in cost, better in product character and more beneficial to synthesis of a finalproduct.

Antimitotic antitumor agents: Synthesis, structure-activity relationships, and biological characterization of N-aryl-N′-(2-chloroethyl)ureas as new selective alkylating agents

A series of N-aryl-N′-(2-chloroethyl)ureas (CEUs) and derivatives were synthesized and evaluated for antiproliferative activity against a wide panel of tumor cell lines. Systematic structure-activity relationship (SAR) studies indicated that: (i) a branched alkyl chain or a halogen at the 4-position of the phenyl ring or a fluorenyl/indanyl group, (ii) an exocyclic urea function, and (iii) a N′-2-chloroethyl moiety were required to ensure significant cytotoxicity. Biological experiments, such as immunofluorescence microscopy, confirmed that these promising compounds alter the cytoskeleton by inducing microtubule depolymerization via selective alkylation of β-tubulin. Subsequent evaluations demonstrated that potent CEUs were weak alkylators, were non-DNA-damaging agents, and did not interact with the thiol function of either glutathione or glutathione reductase. Therefore, CEUs are part of a new class of antimitotic agents. Finally, among the series of CEUs evaluated, compounds 12, 15, 16, and 27 were selected for further in vivo trials.

Reactions of o-Aminonitriles with Isocyanates. 1. A Two-Step Synthesis of 2,6-Dihydroimidazoquinazolin-5-(3H)one

The reaction of anthranilonitrile with 2-chloroethyl isocyanate yields 2-benzonitrile (6) which, upon heating, or treatment with base, undergoes a double cyclization to form 2,6-dihydroimidazoquinazolin-5-(3H)one (8) in excellent yield.When heated with hydrochloric acid, 6 is converted initially into 2-(2-chloroethylamino)-4H-benzoxazin-4-one (18) and further into 3-(2-chloroethyl)-2,4-(1H,3H)quinazolinedione (15).The acid-catalyzed reaction of 2,3-dihydro-5H-oxazoloquinazolin-5-one (14) with nucleophilic reagents yields 3-substituted 2,4-(1H,3H)quinazolinediones.