N,N'-Bis(salicylidene)-1,3-propanediamine

Base Information

• Chemical Name: N,N'-Bis(salicylidene)-1,3-propanediamine
• CAS No.: 120-70-7
• Molecular Formula: C17H18 N2 O2
• Molecular Weight: 282.342
• Hs Code.: 2925290090
• European Community (EC) Number: 204-418-6
• NSC Number: 166332
• DSSTox Substance ID: DTXSID7059513
• Nikkaji Number: J151.235H
• Pharos Ligand ID: PRG1CSG2GLW5
• ChEMBL ID: CHEMBL593165
• Mol file: 120-70-7.mol

Synonyms:disalicylidene propandiamine

Chemical Property of N,N'-Bis(salicylidene)-1,3-propanediamine

Chemical Property:

• Melting Point: 51-53°C
• Boiling Point: 510.1°Cat760mmHg
• PKA: 12.55±0.50(Predicted)
• Flash Point: 191.7°C
• PSA: 65.18000
• Density: 1.288g/cm³
• LogP: 3.02590
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: almost transparency in Toluene
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 282.136827821
• Heavy Atom Count: 21
• Complexity: 312

Purity/Quality:

98%,99%, ^*data from raw suppliers

N,N''-Bis(Salicylidene)-1,3-propanediamine ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36-24/25-22

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Other Aromatics (Nitrogen)
• Canonical SMILES: C1=CC=C(C(=C1)C=NCCCN=CC2=CC=CC=C2O)O
• Uses: N,N′-Bis(salicylidene)-1,3-propanediamine has been used in the synthesis of:new trinuclear heterometallic Cu(II)-Mn(II) complexesmononuclear nickel complex, NiL (LH2 = N,N′-bis(salicylidene)-1,3-diaminopropane)

Technology Process of N,N'-Bis(salicylidene)-1,3-propanediamine

There total 6 articles about N,N'-Bis(salicylidene)-1,3-propanediamine 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: 100.0%

salicylaldehyde (90-02-8) + Trimethylenediamine (109-76-2,54018-94-9) → N,N'-propane-1,3-diylbis(salicylideneimine) (120-70-7)

Guidance literature:

In ethanol; at 20 ℃; for 4h; Reflux;

DOI:10.1080/10426507.2016.1192620

Reference yield: 90.0%

salicylic alcohol (90-01-7) + Trimethylenediamine (109-76-2,54018-94-9) → N,N'-propane-1,3-diylbis(salicylideneimine) (120-70-7)

Guidance literature:

salicylic alcohol; With dihydrogen peroxide; at 20 ℃; for 0.166667h; Green chemistry;

Trimethylenediamine; for 5.5h; Catalytic behavior; Green chemistry;

DOI:10.1016/j.molstruc.2019.03.008

Reference yield: 67.0%

o-hydroxyacetophenone (118-93-4,104809-67-8) + salicylaldehyde (90-02-8) + Trimethylenediamine (109-76-2,54018-94-9) → N-(2-hydroxyacetophenylidene)-N′-salicylidene-1,3-propanediamine + N,N'-propane-1,3-diylbis(salicylideneimine) (120-70-7)

Guidance literature:

o-hydroxyacetophenone; Trimethylenediamine; In acetonitrile; at -10 - 1 ℃; for 0.583333h;

salicylaldehyde; In acetonitrile; at -20 ℃; for 12.5h;

DOI:10.1016/j.ica.2014.07.020

upstream raw materials:

salicylaldehyde

Trimethylenediamine

2-methyl-benzyl alcohol

o-hydroxyacetophenone

Downstream raw materials:

C₂₉H₂₆B₂N₂O₃

diethyl (propane-1,3-diylbis(azanediyl))bis((2-hydroxyphenyl)methylene)bis(hydrogen phosphonate)

Refernces

• 1、 Sarac, Kamiran,Orek, Cahit,Cetin, Ahmet,Dastan, Taner,Koparir, Pelin,Dastan, Sevgi Durna,Koparir, Metin. "Synthesis and in vitro antioxidant evaluation of new bis(α-aminoalkyl)phosphinic acid derivatives". . p. 1284 - 1289. Retrieved 2016.
• 2、 You, Zhong-Lu,Lu, Yao,Zhang, Na,Ding, Bo-Wen,Sun, Hui,Hou, Peng,Wang, Che. "Preparation and structural characterization of hetero-dinuclear Schiff base copper(II)-zinc(II) complexes and their inhibition studies on Helicobacter pylori urease". . p. 2186 - 2194. Retrieved 2011.
• 3、 Seth, Piya,Figuerola, Albert,Jover, Jesús,Ruiz, Eliseo,Ghosh, Ashutosh. "Antiferro- to ferromagnetic crossover in diphenoxido bridged NiII2MnII complexes derived from N2O2 donor Schiff base ligands". . p. 57 - 63. Retrieved 2016.
• 4、 Ergun, Ece,Ergun, ümit,?leri, ?zgür,Kü?ükmüzevir, Muhammed Fatih. "An investigation of some Schiff base derivatives as chemosensors for Zn(II): The performance characteristics and potential applications". . p. 273 - 286. Retrieved 2018.
• 5、 Vafazadeh, Rasoul,Bagheri, Maryam. "Kinetics and mechanism of the ligand exchange reaction between tetradentate schiff base N,N'-ethylen-bis (salicylaldimine) and Ni(N,N'-propylen-bis(salicylaldimine))". . p. 21 - 26. Retrieved 2015.
• 6、 Ghosh, Soumavo,Aromí, Guillem,Gamez, Patrick,Ghosh, Ashutosh. "Structural and Magnetic Analysis of Retrosynthetically Designed Architectures Built from a Triply Bridged Heterometallic (CuL)2Co Node and Benzenedicarboxylates". . p. 3028 - 3037. Retrieved 2015.
• 7、 Acar, Nurcan,Atakol, Orhan,Sopac?, ?aziye Betül,Duman, Demet Cansaran,Svoboda, Ingrid,?z, Sevi. "The investigations of thermal behavior, kinetic analysis, and biological activity of trinuclear complexes prepared ONNO-type Schiff bases with nitrito and nitrato μ-bridges". . p. 1319 - 1337. Retrieved 2017.
• 8、 Nanda, Kausik K.,Dutta, Sujit K.,Baitalik, Sujoy,Venkatsubramanian, Krishnan,Nag, Kamalaksha. "Hydroxide-bridged Diiron(III) Complexes of Tetraaminodiphenol Macrocyclic Ligands: Structure and Properties". . p. 1239 - 1244. Retrieved 1995.
• 9、 Hazari, Alokesh,Das, Lakshmi Kanta,Bauzá, Antonio,Frontera, Antonio,Ghosh, Ashutosh. "Exploring the coordinative adaptation and molecular shapes of trinuclear Cu II 2 MII (M = Zn/Cd) complexes derived from salen type Schiff bases: Structural and theoretical studies". . p. 5730 - 5740. Retrieved 2016.
• 10、 Das, Lakshmi Kanta,Park, Sung-Woo,Cho, Seung Joo,Ghosh, Ashutosh. "An unprecedented "linear-bent" isomerism in tri-nuclear Cu 2IIZnII complexes with a salen type di-Schiff base ligand". . p. 11009 - 11017. Retrieved 2012.