88426-33-9

Basic information

• Product Name: Buparvaquone
• Synonyms: 2-((4-(1,1-dimethylethyl)cyclohexyl)methyl)-3-hydroxy-4-naphthalenedione;2-((4-tert-butylcyclohexyl)methyl)-3-hydroxy-1,4-naphthoquinone;butalex;2-[[4-(1,1-dimethylethyl)cyclohexyl]methyl]-3-hydroxy-1,4-naphthalenedione;BUPARVAQUONE;BW-720C;2-((4-tert-butylcyclohexyl)Methyl)-3-hydroxynaphthalene-1,4-dione;Buparvaquone-d4
• CAS NO: 88426-33-9
• Molecular Formula: C21H26O3
• Molecular Weight: 326.43
• EINECS: 2017-001-1
• Product Categories: Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;API
• Mol File: 88426-33-9.mol
• Article Data: 4

Chemical Properties

• Melting Point: 178-184°C
• Boiling Point: 460.687 °C at 760 mmHg
• Flash Point: 246.536 °C
• Appearance: Yellow crystalline solid
• Density: 1.158 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.574
• Storage Temp.: Refrigerator
• Solubility: DMSO: soluble
• PKA: 5.04±0.10(Predicted)
• CAS DataBase Reference: Buparvaquone(CAS DataBase Reference)
• NIST Chemistry Reference: Buparvaquone(88426-33-9)
• EPA Substance Registry System: Buparvaquone(88426-33-9)

Safety Data

• WGK Germany: 3
• RTECS: QJ5766600
• Hazardous Substances Data: 88426-33-9(Hazardous Substances Data)

Usage

Chemical Properties

Yellow Crystalline Solid

Uses

Analog of antimalarial hydroxynaphthoquinones; tert-butyl derivative of Parvaquone. Antiprotozoal (Theileria)

InChI:InChI=1/C21H26O3/c1-21(2,3)14-10-8-13(9-11-14)12-17-18(22)15-6-4-5-7-16(15)19(23)20(17)24/h4-7,13-14,24H,8-12H2,1-3H3

Upstream product

• 344563-43-5 2-(4-tert-Butyl-cyclohexylmethyl)-3-chloro-[1,4]naphthoquinone 
• 1010-60-2 2-chloro-1,4-naphthoquinone 
• 105906-07-8 1-trans-(4-t-butylcyclohexyl)-acetic acid 

Relevant articles and documents

Buparvaquone preparation method

The invention provides a buparvaquone preparation method, which comprises: carrying out condensation, hydrolysis and decarboxylation by using o-phthalic acid diester and 2-(4-tert-butylcyclohexylmethyl)succinic acid diester as a raw material to prepare 2-[(4-tert-butylcyclohexyl)methyl]-2,3-dihydro-1,4-naphthalenedione, carrying out a substitution reaction on the 2-[(4-tert-butylcyclohexyl)methyl]-2,3-dihydro-1,4-naphthalenedione and a halogenating reagent to obtain a dihalogenated compound mixture, removing halogen hydride through an elimination reaction to obtain 2-[(4-tert-butylcyclohexyl)methyl]-3-halo-1,4-naphthalenedione, and finally carrying out a hydrolysis reaction to obtain the buparvaquone (I). According to the invention, the method has advantages of cheap and easily available raw materials, safe and simple process operation, low cost, little wastewater generation, safety and environmental protection, easily achieved reaction conditions, stable reaction intermediate, high reaction activity, high selectivity and few side reactions, and the prepared buparvaquone is few in impurity and high in purity and yield.

Antiprotozoal agents

Novel combinations of an antiprotozoal naphthoquinone and a 4-pyridinol or an alkanoic ester thereof wherein the antiprotozoal activity of the combination is potentiated with respect to the corresponding activity of the components of the combination. The combinations are especially useful for the treatment or porphylaxis of malaria.