3-(cyanomethylene)glutaric acid dimethyl ester

Base Information

• Chemical Name: 3-(cyanomethylene)glutaric acid dimethyl ester
• CAS No.: 1709-25-7
• Molecular Formula: C₉H₁₁NO₄
• Molecular Weight: 197.191
• Mol file: 1709-25-7.mol

Synonyms:Glutaricacid, 3-(cyanomethylene)-, dimethyl ester (7CI,8CI); Pentanedioic acid,3-(cyanomethylene)-, dimethyl ester (9CI); NSC 79877

Chemical Property of 3-(cyanomethylene)glutaric acid dimethyl ester

Chemical Property:

• Vapor Pressure: 0.000425mmHg at 25°C
• Boiling Point: 315.9°Cat760mmHg
• Flash Point: 137.2°C
• PSA: 76.39000
• Density: 1.154g/cm³
• LogP: 0.56258
• Storage Temp.: Refrigerator

Purity/Quality:

99%min ^*data from raw suppliers

Dimethyl3-(cyanomethlene)pentanedioate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Dimethyl 3-(cyanomethlene)pentanedioate (cas# 1709-25-7) is a compound useful in organic synthesis.

Technology Process of 3-(cyanomethylene)glutaric acid dimethyl ester

There total 2 articles about 3-(cyanomethylene)glutaric acid dimethyl ester 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: 90.0%

3-oxopentanedioic acid dimethyl ester (1830-54-2) + cyanoacetic acid (372-09-8) → dimethyl 3-(cyanomethylene)pentanedioate (1709-25-7)

Guidance literature:

With ammonium acetate; acetic acid; In benzene; for 24h; Reflux;

DOI:10.1002/chem.200903053

Reference yield:

→ dimethyl 3-(cyanomethylene)pentanedioate (1709-25-7)

Guidance literature:

Cyanessigsaeure, Acetondicarbonsaeuredimethylester, Bzl., Ammonacetat, Essigsaeure, Kochen;

Reference yield:

dimethyl 3-(cyanomethylene)pentanedioate (1709-25-7) → methyl 6-bromo-1,2-dihydro-2-oxo-1-(2-propynyl)-4-pyridineacetate (141807-55-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / NaOH / ethanol

2: 1.) PCl₅, 2.) HBr gas

3: 70 percent / NaH, LiBr / 1,2-dimethoxy-ethane

With sodium hydroxide; phosphorus pentachloride; hydrogen bromide; sodium hydride; lithium bromide; In 1,2-dimethoxyethane; ethanol;

DOI:10.1021/ja00040a060

upstream raw materials:

3-oxopentanedioic acid dimethyl ester

cyanoacetic acid

Downstream raw materials:

methyl 6-bromo-1,2-dihydro-2-oxo-1-(2-propynyl)-4-pyridineacetate

Refernces

• 1、 -. "PYRROLOPYRIMIDINE AND PYRROLOPYRIDINE DERIVATIVES SUBSTITUTED WITH A CYCLIC AMINO GROUP AS CRF ANTAGONISTS". Page/Page column 53-54. . Retrieved 2010/02/15.
• 2、 Curran, Dennis P.,Liu, Hui. "New 4 + 1 radical annulations. A formal total synthesis of (±)-camptothecin". . p. 5863 - 5864. Retrieved 2007/10/02.