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

Melting point:

51-53°C

Boiling point:

466.4±40.0 °C(Predicted)

Density 

1.11±0.1 g/cm3(Predicted)

Flash point:

113 °C

storage temp. 

Sealed in dry,Room Temperature

solubility 

almost transparency in Toluene

form 

powder to crystal

pka

12.55±0.50(Predicted)

color 

Light yellow to Yellow to Green

BRN 

2057483

InChI

InChI=1S/C17H18N2O2/c20-16-8-3-1-6-14(16)12-18-10-5-11-19-13-15-7-2-4-9-17(15)21/h1-4,6-9,12-13,20-21H,5,10-11H2

InChIKey

KLDZYURQCUYZBL-UHFFFAOYSA-N

SMILES

C(N=CC1=CC=CC=C1O)CCN=CC1=CC=CC=C1O

CAS DataBase Reference

120-70-7(CAS DataBase Reference)

EPA Substance Registry System

Phenol, 2,2'-[1,3-propanediylbis(nitrilomethylidyne)]bis- (120-70-7)

Safety

Risk Statements 

36/37/38

Safety Statements 

26-36-24/25-22

WGK Germany 

3

HS Code 

2925.29.9000

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

N,N'-Bis(salicylidene)-1,3-propanediamine Chemical Properties,Usage,Production

Chemical Properties

Light yellow to Yellow to Green powder to crystal

Uses

N,N′-Bis(salicylidene)-1,3-propanediamine has been used in the synthesis of:

• new trinuclear heterometallic Cu(II)-Mn(II) complexes
• mononuclear nickel complex, NiL (LH₂ = N,N′-bis(salicylidene)-1,3-diaminopropane)

Application

N, N'-bis(salicylidene)-1,3-propane diamine (SB-Salpr) could prepare a new Al3+ carbon paste ion selective electrode to quantify trace Aluminum. The bi-thioglycolate functionalized salpn linker could be further transformed into Cu-ICP nanoparticles. This linker could be synthesized through the functionalization of salpn (salpn = N, N'-Bis(salicylidene)-1,3-propanediamine) ligand with sodium thioglycolate[1–2].

General Description

N,N′-Bis(salicylidene)-1,3-propanediamine is a di-Schiff base ligand.

Synthesis

N,N'-Bis(salicylidene)-1,3-propanediamine is prepared by the reaction of 2-Hydroxybenzaldehyde and 1,3-diaminopropane. The specific synthesis steps are as follows:
General procedure: This Schiff base was prepared via a condensation reaction in EtOH under hydrothermal conditions using 2-hydroxy-benzaldehyde and 1,3-diaminopropane. 2-Hydroxy-benzaldehyde (0.02 mol, 2.44 g) was dissolved in 40 cm3 of warm EtOH, then 0.01 mol (0.74 g) of 1,3-diaminopropane was added to this solution and heated up to the boiling point. After cooling, yellow crystals were filtered and air-dried. Yield: 92-95%, mp 58 °C (determined by TG). Elemental Anal. Calc. for C17H18N2O2: C, 72.3; H, 6.43; N, 9.92. Found: C, 71.9; H, 6.45; N, 10.47%. λmax = 243 nm, ε = 7045 dm3 mol-1 cm-1 in DMSO, λmax = 242 nm, ε = 7865 dm3 mol-1 cm-1 in MeOH. IR (cm-1): νO-H 2627, νC-H(Ar) 3021-3019, νC-H(aliph) 2929-2862, νC=N 1629, νC=C(ring) 1608, νC-O(phenol) 1274-1151, δC-H(Ar) 762. 1H NMR in d6-DMSO: 13.51 (s) (O-H), 8.60 (s) (-CH=), 7.43 (d) (HAr), 7.32 (t) (HAr), 6.88 (t) (HAr), 3.68 (t) (N-CH2-), 2.01 (p) (-CH2-). 13C NMR in d6-DMSO: 166.6, 161.1, 132.7, 132.1, 119.1, 118.9 (CAr), 116.9 (-C=N), 58.5 (N-CH2-), 31.9 (-CH2-). m/z: 282 [M]+, 161 [HO-C6H4-CH=N-CH2-CH2-CH2]+, 148 [HO-C6H4-CH=N-CH2-CH2]+ (BP), 134 [HO-C6H4-CH=N-CH2]+, 120 [HO-C6H4-CH=N]+, 107 [HO-C6H4-CH2]+, 77 [C6H5]+.

References

[1] RAZIEH SANAVI KHOSHNOOD Toktam M C,  Setareh Akbari. Determination of Aluminium by Potentiometry Using Carbon Paste Ion Selective Electrode Based on N,N’-bis(salicylidene)-1,3-Propanediamine Ligand[J]. Journal of Analytical Chemistry, 2022, 77 8: 1057-1061. DOI:10.1134/S1061934822080111.
[2] M. MOHAMMADIKISH, Zohreh Z. Coordination-induced formation of nanometer-scale infinite coordination polymer at room temperature and conversion to CuO nanoparticles[J]. Materials Research Express, 2018. DOI:10.1088/2053-1591/aab7b7.