104-69-8

Basic information

• Product Name: N,N'-diphenylpropane-1,3-diamine
• Synonyms: N,N'-diphenylpropane-1,3-diamine;N,N'-Diphenyl-1,3-propanediamine
• CAS NO: 104-69-8
• Molecular Formula: C₁₅H₁₈N₂
• Molecular Weight: 226.31682
• EINECS: 203-228-0
• Mol File: 104-69-8.mol

Chemical Properties

• Boiling Point: 424.3°Cat760mmHg
• Flash Point: 274.2°C
• Appearance: /
• Density: 1.099g/cm³
• CAS DataBase Reference: N,N'-diphenylpropane-1,3-diamine(CAS DataBase Reference)
• NIST Chemistry Reference: N,N'-diphenylpropane-1,3-diamine(104-69-8)
• EPA Substance Registry System: N,N'-diphenylpropane-1,3-diamine(104-69-8)

Safety Data

• Hazardous Substances Data: 104-69-8(Hazardous Substances Data)

Usage

Uses

Used in Rubber Industry:
N,N'-diphenylpropane-1,3-diamine is used as an antioxidant for rubber products to inhibit the oxidation process, which is crucial for extending the lifespan and maintaining the integrity of rubber items. Its application ensures that rubber products remain functional and durable over time.
Used in Plastics Industry:
In the plastics industry, N,N'-diphenylpropane-1,3-diamine serves as a stabilizer to prevent the deterioration of plastic materials when exposed to heat and light. This role is vital for maintaining the quality and performance of plastic products, especially those used in environments with fluctuating temperatures or direct sunlight exposure.
While DPPD offers significant benefits in these applications, there is an ongoing need for research to better understand its potential health and environmental impacts, ensuring the responsible and safe use of this chemical compound in various industries.

Upstream product

• 7647-01-0 hydrogenchloride 
• 60-29-7 diethyl ether 
• 63378-86-9 1,2-diphenyl-pyrazolidine 
• 62-53-3 aniline 
• 109-64-8 1,3-dibromo-propane 
• 100-61-8 N-methylaniline 
• 504-63-2 trimethyleneglycol 
• 591-50-4 iodobenzene 
• 109-76-2 Trimethylenediamine 
• 108-86-1 bromobenzene 
• 100910-72-3 1,3-diazido-propane 
• 5469-66-9 propane-1,3-diol ditosylate 
• 56535-86-5 3-phenyl-1,3-oxazinan-2-one 
• 5799-03-1 N,N'-dinitroso-N,N'-diphenyl-propanediyldiamine 

Downstream Products

• 63114-21-6 1,2,3-triphenyl-hexahydro-pyrimidine 
• 854650-62-7 N,N'-dinitro-N,N'-dipicryl-propanediyldiamine 
• 63378-86-9 1,2-diphenyl-pyrazolidine 
• 1315303-62-8 C₁₉H₂₀Br₂N₂O₂ 
• 35385-98-9 N,N',N'',N'''-tetraphenyl-N,N''-propanediyl-di-urea 
• 80378-38-7 2-chloro-1,3-diphenyl-1,3,2-diazaphosphorinane 
• 78946-53-9 3,4-dihydro-2,6-diphenyl-1,2,6-thiadiazine S-oxide 
• 63114-22-7 N,N'-diacetyl-N,N'-diphenylpropanediamine 
• 5799-03-1 N,N'-dinitroso-N,N'-diphenyl-propanediyldiamine 
• 122215-87-6 N,N'-propanediyl-bis-benzanilide 
• 59282-07-4 1,3-diphenylhexahydropyrimidine 

Relevant articles and documents

Iridium-Catalyzed Direct Cyclization of Aromatic Amines with Diols

We developed an environmentally friendly iridium-catalyzed direct cyclization of aromatic amines with diols that generates the corresponding N-heterocyclic compounds with water as the sole by-product. Thus, under conditions of 165 °C for 18 hours, the direct cyclization of N -methylanilines with 1,3-propanediol by using an IrCl 3 catalyst with rac -BINAP as a ligand in mesitylene afforded the corresponding tetrahydroquinoline derivatives with yields ranging from 73 to 83%. Under similar reaction conditions, direct cyclization of anilines with 1,3-propanediol produced the corresponding tetrahydrobenzoquinolizine derivatives with yields ranging from 26 to 76%.

C-N Coupling of nitrogen nucleophiles with aryl and heteroaryl bromides using aminoarenethiolato-copper(I) (pre-)catalyst

The activity of a library of 2-aminoarenethiolato-copper(I) (CuSAr) (pre-)catalyst was explored in the arylation reaction of amines and N-containing heterocycles with aryl and heteroaryl bromides, respectively. These CuSAr pre-catalysts are thermally stable, are soluble in common organic solvents and show good catalytic activities in these N-arylation reactions with catalyst loadings amounting to 2.5 mol %. The targeted C-N coupling products were obtained in moderate to good yields (40-97%) for a variety of substrates.

Palladium-catalyzed synthesis of aryl-substituted polyamine compounds from aryl halides

The reaction of polyamines having primary amino groups and 1,2-diaminoethane and/or 1,3-diaminopropane fragments with aryl bromides or iodides in the presence of sodium tert-butoxide and (dppf)PdCl2 (dppf = 1,1'-bis(diphenylphosphino)ferrocene) proceeds selectively leading to monoaryl-substituted derivatives of polyamine. This reaction provides a convenient method of arylation of di-, tri- and tetraamine compounds. The Pd-catalyzed reactions of 1,3-diaminopropane and 3,3'-diaminodipropylamine with more reactive 1-bromonaphthalene can be used for the preparation of sym-dinaphthyl derivatives of these amines.

Adding value to renewables: A one pot process combining microbial cells and hydrogen transfer catalysis to utilise waste glycerol from biodiesel production

Waste glycerol was converted to secondary amines in a one pot reaction, using Clostridium butyricum and catalytic hydrogen transfer-mediated amination. The Royal Society of Chemistry 2009.

Ullmann-type C-N coupling reaction catalyzed by CuI/metformin

A facile and efficient method for Ullmann-type C-N coupling reaction of amine and aryl halide catalyzed by CuI/metformin in EtOH is described. The advantages of this method are the use of an inexpensive and readily available catalyst and ligand, easy workup, shorter reaction time, improved yields, and the use of green solvent. Furthermore, this procedure is applied successfully for the modification of natural products, such as Vindoline and Tabersonin.

Heterogeneous bimetallic Pt-Sn/γ-Al2O3 catalyzed direct synthesis of diamines from N-alkylation of amines with diols through a borrowing hydrogen strategy

Direct synthesis of diamines has been efficiently realized from the N-alkylation of amines with diols by means of heterogeneous bimetallic Pt-Sn/γ-Al2O3 catalyst (0.5 wt % Pt, molar ratio Pt:Sn = 1:3) through a 'Borrowing Hydrogen' strategy under ligand-free conditions. The present methodology provides an environmentally benign route to diamines.

Palladium-catalyzed arylation of linear and cyclic polyamines

The palladium-catalyzed arylation of polyandries is investigated and it is shown that the C-N coupling reaction for a given substrate is strongly dependent on the nature and the concentration of the catalytic system, as well as the nature of the base employed. The arylation of the primary amino group is favored when both primary and secondary amines are present; selective arylation is then possible without using any protecting group. The reaction of dihalobenzenes with polyamines gives the monoamination products in good yields without any significant formation of diamino compounds or reduced derivatives, unlike what is observed when monoamines are used. The extent of polyarylation of polyamines as a function of the excess of aryl halide and the nature and the amount of catalyst is also studied. Finally, N-arylation of a macrocyclic tetraamine (cyclam) is performed by using an appropriate catalytic system. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.

Chelate-controlled synthesis of racemic ansa-zirconocenes

The reaction of Zr{PhN(CH2)3NPh}Cl 2(THF)2 (5) with lithium ansa-bis-indenyl reagents Li 2[XBI]-(Et2O) (XBI = (1-indenyl)2SiMe 2 (SBI, 7a), (2-methyl-1-indenyl)2SiMe2 (MSBI, 7b), (2-methyl-4,5-benz-1-indenyl)2SiMe2 (MBSBI, 7c), (2-methyl-4-phenyl-1-indenyl)2SiMe2 (MPSBI, 7d), and 1,2-(1-indenyl)2ethane (EBI, 7e)) affords rac-(XBI)Zr{PhN(CH 2)3NPh} (8a-e) in high yield. The meso isomers were not detected by 1H NMR. X-ray crystallographic studies show that the Zr{PhN(CH2)3NPh} rings in 5, 8a, 8c, and (C 5H5)2-Zr{PhN(CH2)3NPh} (10) adopt twist conformations that position the N-Ph groups on opposite sides of the N-Zr-N plane. This conformation complements the metallocene structures of rac-8a-e but would destabilize the corresponding meso isomers. It is proposed that the Zr{PhN(CH2)3NPh} ring adopts a similar twist conformation in the stereodetermining transition state for addition of the second indenyl ring in these reactions, which leads to a preference for rac products. The results of metallocene syntheses from other Zr amide precursors support this proposal. 8a-e are converted to the corresponding rac-(XBI)ZrCl2 complexes (9a-e) by reaction with HCl.

2-Propanol derivatives as corrosion inhibitors

New composition comprises a functional fluid in contact with ferrous metal and a corrosion inhibiting amount of at least one compound of formula (I) STR1 or a derivative thereof in which R1, R2 and R3 are, independently, hydrogen, a C1 -C15 straight or branched chain alkyl residue, a C5 -C12 cycloalkyl residue, a C6 -C15 aryl residue or C7 -C12 alkaryl residue, and R4 and R5 are, independently, hydrogen, 2-hydroxyethyl or 2-hydroxypropyl with the provisos that (a) R4 and R5 are not simultaneously hydrogen, (b) when R4 and R5 are each --CH2 --CH2 --OH, R1 and R2 are not simultaneously hydrogen and R3 is not a pentyl residue and (c) that polyalkylene and phenol or polycarboxylic ester co-additives are absent; as well as salts thereof. Some of the compounds of formula I are new.

Corrosion inhibiting composition

A composition, in contact with a corrodable metal surface, which composition comprises: (a) an aqueous-based or oil-based system; and (b) as inhibitor for protecting the metal surface against corrosion, at least one compound having the formula I: STR1 as well as salts or partial esters thereof wherein: n is 0 or an integer ranging from 1 to 20, R is a straight or branched chain C4 -C30 alkyl group, optionally interrupted by one, two or three oxygen atoms or substituted by one, two or three hydroxy groups, a C5 -C12 cycloalkyl group, a C6 -C10 aryl group optionally substituted by one, two or three C1 -C12 alkyl groups, or a C7 -C13 aralkyl group which is optionally substituted by a hydroxyl group; R1 is H or a straight- or branched chain C1 -C4 alkyl group; R2 is H, a straight or branched chain C1 -C4 alkyl group or CO2 H; R3 is H, a straight or branched chain C1 -C4 alkyl group, --CH2 CO2 H or --CH2 CH2 CO2 H; R4 is H, a straight or branched chain C1 -C4 alkyl group or CO2 H; R5 is H, a straight or branched chain C1 -C4 alkyl group, CH2 CO2 H or CH2 CH2 CO2 H; provided that at least one group R4 must be CO2 H, with the provisio, that compositions comprising an oil-based system and a compound having the formula STR2 wherein R, R1 and R2 are hydrogen or alkyl radicals, having a total from 10 to 38 C-atoms, are excluded.