20605-01-0

Basic information

• Product Name: Diethyl bis(hydroxymethyl)malonate
• Synonyms: TIMTEC-BB SBB007847;2,2-BIS(HYDROXYMETHYL)MALONIC ACID DIETHYL ESTER;MALONIC ACID, BIS [HYDROXYMETHYL] DIETHYL ESTER;DIETHYL BIS(HYDROXYMETHYL)MALONATE;bis(hydroxymethyl)-propanedioicacidiethylester;Diethyl 2,2-bis(hydroxymethyl)malonate;Propanedioic acid, bis(hydroxymethyl)-, diethyl ester;Ethyl Dimethylol Malonate
• CAS NO: 20605-01-0
• Molecular Formula: C₉H₁₆O₆
• Molecular Weight: 220.22
• EINECS: 243-916-8
• Product Categories: Pharmaceutical Intermediates;Small molecule;Alcohols;Monomers;Polymer Science
• Mol File: 20605-01-0.mol
• Article Data: 16

Chemical Properties

• Melting Point: 49-51 °C(lit.)
• Boiling Point: 281.15°C (rough estimate)
• Flash Point: >230 °F
• Appearance: White to almost white/Crystalline Solid
• Density: 1.2286 (rough estimate)
• Vapor Pressure: 2.45E-06mmHg at 25°C
• Refractive Index: 1.4390 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 12.59±0.10(Predicted)
• Water Solubility: Slightly soluble in water.
• BRN: 1788515
• CAS DataBase Reference: Diethyl bis(hydroxymethyl)malonate(CAS DataBase Reference)
• NIST Chemistry Reference: Diethyl bis(hydroxymethyl)malonate(20605-01-0)
• EPA Substance Registry System: Diethyl bis(hydroxymethyl)malonate(20605-01-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 23-24/25-36-26
• WGK Germany: 3
• TSCA: Yes
• HazardClass: IRRITANT
• Hazardous Substances Data: 20605-01-0(Hazardous Substances Data)

Usage

Uses

Diethyl bis(hydroxymethyl)malonate is used as a reagent for preparing 1,3-dioxanes from acetals, aldehydes and ketones. It is also used as an intermediate for the preparation of substituted malonic, acrylic and isobutyric esters, for conversion to the useful dienophiles, ?-bromomethylacrylic acid and its ethyl ester and to bis(bromomethyl)acetic acid and its methyl ester.

InChI:InChI=1/C9H16O6/c1-3-14-7(12)9(5-10,6-11)8(13)15-4-2/h10-11H,3-6H2,1-2H3

Upstream product

• 50-00-0 formaldehyd 
• 105-53-3 diethyl malonate 
• 51335-75-2 2,2-Dimethyl-1,3-dioxacyclohexane-5,5-dicarboxylic acid,diethyl ester 
• 56-23-5 tetrachloromethane 

Downstream Products

• 41459-42-1 3-bromo-2-(bromomethyl)propionic acid 
• 17435-77-7 ethyl 2-(chloromethyl)acrylate 
• 10029-04-6 ethyl 2-(hydroxymethyl)acrylate 
• 173783-71-6 bis-hydroxymethyl-malonic acid 
• 50-00-0 formaldehyd 
• 64-17-5 ethanol 
• 3377-20-6 diethyl methylenemalonate 
• 140-88-5 ethyl acrylate 
• 71348-41-9 diethyl 6-phenyl-[1,5]-dioxane-3,3-dicarboxylic acid diester 
• 174583-27-8 2-(1-Benzyl-4,5-diphenyl-1H-imidazol-2-yl)-[1,3]dioxane-5,5-dicarboxylic acid diethyl ester 
• 642411-11-8 3,3‐diethyl 1‐benzylazetidine‐3,3‐dicarboxylate 
• 135098-43-0 1-benzyl-2-<5,5-bis(ethoxycarbonyl)-1,3-dioxan-2-yl>-4,5-diphenylimidazole 
• 82962-54-7 2,2-dimethyl-5-ethoxycarbonyl-1,3-dioxane 
• 35113-48-5 2-isopropyl-5,5-bis(carboethoxy)-1,3-dioxane 

Relevant articles and documents

Synthesis, antiproliferative activity and DNA binding study of mixed ammine/cyclohexylamine platinum(II) complexes with 1-(substituted benzyl) azetidine-3, 3-dicarboxylates

A novel series of ammine/cyclohexylamine platinum(II) complexes with 1-(substituted benzyl) azetidine-3, 3-dicarboxylates as leaving groups have been synthesized and characterized. All complexes were characterized by elemental analysis, IR, 1H NMR, and ESI-MS spectra. The in vitro antiproliferative activities of the platinum-based compounds have been investigated against several human cancer cell lines, indicating that complexes 1 and 11 showed comparable cytotoxicity to those of cisplatin and oxaliplatin against four cell lines, superior to that of carboplatin. The results of drug safety evaluation (acute toxicity study) showed that complex 11 was much less toxic than cisplatin and oxaliplatin. Flow cytometry and agarose gel electrophoresis studies revealed that both complexes 1 and 11 induced apoptosis of tumor cells and demonstrated the binding affinity of complexes with pET22b plasmid DNA.

Novel intermediate and improved process for the preparation of iobitridol using thereof

The present invention relates to a novel method for producing iobitridol represented by chemical formula 1, 1-N,3-N-bis(2,3-dihydroxypropyl)-5-[3-hydroxy-2-(hydroxymethyl)propanamido]-2,4,6-triiodo-1-N,3-N-dimethylbenzene-1,3-dicarboxamide, which is a component for a contrast medium, and novel intermediates for the same. According to the present invention, desired entecavir can be produced economically and easily from the novel intermediates at a high yield.COPYRIGHT KIPO 2018

Synthesis of Panal Terpenoid Core

Panal is a natural bicyclic cadalane-type sesquiterpenoid with an unusual combination of stereocenters. It was isolated in 1988 as an alleged biosynthetic precursor of luciferin (a light-emitting molecule) in a bioluminescent fungus Panellus stipticus. Herein we present the first approach to the synthesis of the terpenoid skeleton of panal, which includes construction of five stereocenters, one of which is easily epimerizable. The key steps in the synthetic approach presented are high-pressure Diels-Alder reaction disobeying the ‘endo rule’, Barbier reductive allylation, and cyclization of trans-decalin ring via ring-closing metathesis.