4-Nitrobenzyl hydrogen malonate

Base Information

• Chemical Name: 4-Nitrobenzyl hydrogen malonate
• CAS No.: 77359-11-6
• Molecular Formula: C10H9NO6
• Molecular Weight: 239.185
• Hs Code.: 2918990090
• Mol file: 77359-11-6.mol

Synonyms:Propanedioicacid, mono[(4-nitrophenyl)methyl] ester (9CI);Malonic acid mono-p-nitrobenzylester;Mono-4-nitrobenzyl malonate;Mono-p-nitrobenzyl malonate;p-Nitrobenzylmalonate;

Chemical Property of 4-Nitrobenzyl hydrogen malonate

Chemical Property:

• Appearance/Colour: white to slight yellow powder
• Vapor Pressure: 4.22E-09mmHg at 25°C
• Melting Point: 109 °C
• Refractive Index: 1.579
• Boiling Point: 455.8 °C at 760 mmHg
• PKA: 2.49±0.32(Predicted)
• Flash Point: 229.5 °C
• PSA: 109.42000
• Density: 1.447 g/cm³
• LogP: 1.63590
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: soluble in Methanol

Purity/Quality:

99% ^*data from raw suppliers

3-[(4-Nitrobenzyl)oxy]-3-oxopropanoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 4-Nitrobenzyl hydrogen malonate is a reagent used in the synthesis of (±)-thienamycin, a β-Lactam antibiotics. Also, it is useful for chiral key intermediate of carbapenem syntheses.

Technology Process of 4-Nitrobenzyl hydrogen malonate

There total 8 articles about 4-Nitrobenzyl hydrogen malonate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

4-nitrobenzyl chloride (619-73-8) + malonic acid (141-82-2) → propanedioic acid mono[(4-nitrophenyl)methyl] ester (77359-11-6)

Guidance literature:

With toluene-4-sulfonic acid; In toluene; at 110 - 112 ℃; Large scale;

Reference yield: 83.0%

cycl-isopropylidene malonate (2033-24-1) + 4-nitrobenzyl chloride (619-73-8) → propanedioic acid mono[(4-nitrophenyl)methyl] ester (77359-11-6)

Guidance literature:

In acetonitrile; at 80 ℃; Inert atmosphere;

DOI:10.1016/j.bmcl.2015.04.099

Reference yield: 80.0%

Bis(p-nitrobenzyl) malonate (67245-85-6) → propanedioic acid mono[(4-nitrophenyl)methyl] ester (77359-11-6)

Guidance literature:

With malonic acid; p-toluenesulfonic acid monohydrate; In nitrobenzene;

upstream raw materials:

cycl-isopropylidene malonate

4-nitrobenzyl chloride

Bis(p-nitrobenzyl) malonate

tert-butylmethyl ether

Downstream raw materials:

p-Nitrobenzyl ester of N-Methyl-N-(benzyloxy)malonamide

17β-(3-benzyloxyoestra-1,3,5(10)-trienyl) p-nitrobenzyl malonate

Refernces

• 1、 -. "Preparation method and application of p-nitrobenzyl alcohol". Paragraph 0036-0037. . Retrieved 2019/01/05.
• 2、 Ryu, Youngha,Scott, A. Ian. "Self-condensation of activated malonic acid half esters: A model for the decarboxylative Claisen condensation in polyketide biosynthesis". . p. 7499 - 7502. Retrieved 2007/10/03.