Diethyl 2,2'-(2,5-dihydroxy-1,4-phenylene)bis(cyanoacetate)

Base Information

• Chemical Name: Diethyl 2,2'-(2,5-dihydroxy-1,4-phenylene)bis(cyanoacetate)
• CAS No.: 57271-90-6
• Molecular Formula: C16H16 N2 O6
• Molecular Weight: 332.313
• NSC Number: 78843
• DSSTox Substance ID: DTXSID60291876
• Mol file: 57271-90-6.mol

Synonyms:57271-90-6;diethyl 2,2'-(2,5-dihydroxy-1,4-phenylene)bis(cyanoacetate);ethyl 2-cyano-2-[4-(1-cyano-2-ethoxy-2-oxoethyl)-2,5-dihydroxyphenyl]acetate;NSC 78843;2-cyano-2-[4-(1-cyano-2-ethoxy-2-oxoethyl)-2,5-dihydroxyphenyl]acetic acid ethyl ester;DIETHYL 2,2'-(2,5-DIHYDROXY-1,4-PHENYLENE)BIS(2-CYANOACETATE);NSC78843;DTXSID60291876;NSC-78843;STK955433;AKOS024406047;F89261;A831365;diethyl 2,2'-(2,5-dihydroxybenzene-1,4-diyl)bis(cyanoacetate);ethyl 2-cyano-2-[4-(1-cyano-2-ethoxy-2-oxidanylidene-ethyl)-2,5-bis(oxidanyl)phenyl]ethanoate

Chemical Property of Diethyl 2,2'-(2,5-dihydroxy-1,4-phenylene)bis(cyanoacetate)

Chemical Property:

• Boiling Point: 581.2ºC at 760 mmHg
• Flash Point: 305.3ºC
• PSA: 140.64000
• Density: 1.349g/cm3
• LogP: 1.43836
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 8
• Exact Mass: 332.10083623
• Heavy Atom Count: 24
• Complexity: 509

Purity/Quality:

99% ^*data from raw suppliers

DIETHYL 2,2'-(2,5-DIHYDROXY-1,4-PHENYLENE)BIS(2-CYANOACETATE) 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(C#N)C1=CC(=C(C=C1O)C(C#N)C(=O)OCC)O

Technology Process of Diethyl 2,2'-(2,5-dihydroxy-1,4-phenylene)bis(cyanoacetate)

There total 2 articles about Diethyl 2,2'-(2,5-dihydroxy-1,4-phenylene)bis(cyanoacetate) 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: 25.0%

ethyl 2-cyanoacetate (105-56-6) + p-benzoquinone (106-51-4) → 2,2'-dicyano-2,2'-(2,5-dihydroxy-p-phenylene)-di-acetic acid diethyl ester (57271-90-6)

Guidance literature:

With ammonium hydroxide; In ethanol;

DOI:10.1039/c6tc03876j

Reference yield:

ammonia (7664-41-7) + ethyl 2-cyanoacetate (105-56-6) + p-benzoquinone (106-51-4) → 2,2'-dicyano-2,2'-(2,5-dihydroxy-p-phenylene)-di-acetic acid diethyl ester (57271-90-6)

Guidance literature:

DOI:10.1021/ja01237a038

Reference yield: 59.0%

2,2'-dicyano-2,2'-(2,5-dihydroxy-p-phenylene)-di-acetic acid diethyl ester (57271-90-6) → 2,2′-(2,5-dihydroxy-1,4-phenylene)diacetic acid (5488-16-4)

Guidance literature:

With hydrogenchloride; water; at 110 ℃;

DOI:10.1039/d0tc03347b

upstream raw materials:

ammonia

ethyl 2-cyanoacetate

p-benzoquinone

Downstream raw materials:

2,2′-(2,5-dihydroxy-1,4-phenylene)diacetic acid

1,4-bis(2-bromoethyl)-2,5-dimethoxybenzene

2-[4-(2-hydroxyethyl)-2,5-dimethoxyphenyl]ethanol

methyl 2-[2,5-dimethoxy-4-(2-methoxy-2-oxoethyl)phenyl]acetate

Refernces

• 1、 Alsufyani, Maryam,Bristow, Helen,Chen, Hu,Chen, Xingxing,Fabiano, Simone,Hallani, Rawad K.,Ji, Xudong,McCulloch, Iain,Paulsen, Bryan D.,Rivnay, Jonathan,Sirringhaus, Henning,Wang, Suhao,Xiao, Mingfei,Xu, Kai. "The effect of aromatic ring size in electron deficient semiconducting polymers for n-type organic thermoelectrics". supporting information. p. 15150 - 15157. Retrieved 2020/11/23.
• 2、 Singla, Priya,Van Steerteghem, Nick,Kaur, Navdeep,Ashar,Kaur, Paramjit,Clays, Koen,Narayan,Singh, Kamaljit. "Multifunctional geometrical isomers of ferrocene-benzo[1,2-b:4,5-b′]difuran-2,6-(3H,7H)-dione adducts: second-order nonlinear optical behaviour and charge transport in thin film OFET devices". . p. 697 - 708. Retrieved 2017/01/28.