Triethylenetetramine

Base Information

• Chemical Name: Triethylenetetramine
• CAS No.: 112-24-3
• Deprecated CAS: 105093-20-7,110670-33-2,14175-14-5,39421-77-7,71124-11-3,193487-08-0,801997-18-2,150139-02-9,1309612-46-1,1404190-34-6,1821166-92-0,2245055-56-3,442681-17-6,110670-33-2,1309612-46-1,1404190-34-6,14175-14-5,1821166-92-0,193487-08-0,39421-77-7,71124-11-3,801997-18-2
• Molecular Formula: C6H18N4
• Molecular Weight: 146.236
• Hs Code.: 29212900
• European Community (EC) Number: 203-950-6
• ICSC Number: 1123
• NSC Number: 443
• UN Number: 2259
• UNII: SJ76Y07H5F
• DSSTox Substance ID: DTXSID9023702
• Nikkaji Number: J5.120I
• Wikipedia: Triethylenetetramine
• Wikidata: Q418386
• NCI Thesaurus Code: C66633
• RXCUI: 10798
• Metabolomics Workbench ID: 52233
• ChEMBL ID: CHEMBL609
• Mol file: 112-24-3.mol

Synonyms:Syprine;Trien;Trientine;Trientine Dihydrochloride;Trientine Hydrochloride;Triethylenetetramine

Chemical Property of Triethylenetetramine

Chemical Property:

• Appearance/Colour: colourless to light yellow or amber viscous liquid
• Vapor Pressure: <0.01 mm Hg ( 20 °C)
• Melting Point: 12 °C(lit.)
• Refractive Index: 1.4971
• Boiling Point: 266.499 °C at 760 mmHg
• PKA: pK1:3.32(+4);pK2:6.67(+3);pK3:9.20(+2);pK4:9.92(+1) (20°C)
• Flash Point: 149 °C
• PSA: 76.10000
• Density: 0.9817 g/mL at 25 °C(lit.)
• LogP: 0.26540
• Storage Temp.: Store below +30°C.
• Sensitive.: Moisture Sensitive
• Solubility.: alcohol: soluble
• Water Solubility.: SOLUBLE
• XLogP3: -2.5
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 146.153146591
• Heavy Atom Count: 10
• Complexity: 49.7
• Transport DOT Label: Corrosive

Purity/Quality:

98% ^*data from raw suppliers

Triethylenetetramine(TechnicalGrade) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 21-34-43-52/53
• Safety Statements: 26-36/37/39-45-61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Amines, Aliphatic
• Drug Classes: Chelating Agents
• Canonical SMILES: C(CNCCNCCN)N
• Recent ClinicalTrials: The Efficacy and Mechanism of Trientine in Patients With Hypertrophic Cardiomyopathy
• Recent EU Clinical Trials: A randomised, double-blind, placebo-controlled, phase 2 evaluation of the efficacy and mechanism of trientine in patients with hypertrophic cardiomyopathy.
• Inhalation Risk: No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
• Effects of Short Term Exposure: The substance is corrosive to the eyes, skin and respiratory tract. Corrosive on ingestion. Inhalation may cause lung oedema, but only after initial corrosive effects on eyes and/or airways have become manifest.
• Effects of Long Term Exposure: Repeated or prolonged contact may cause skin sensitization. Repeated or prolonged inhalation may cause asthma.
• Description: Cross sensitivity is possible with diethylenetriamine and diethylenediamine.
• Uses: Triethylenetetramine is used as an amine hardener in epoxy resin of the bisphenol A type. Triethylenetetramine is used in synthesis of detergents, softeners, and dyestuffs; manufacture of pharmaceuticals; vulcanization accelerator of rubber; thermo setting resin; epoxy curing agent; lubricating-oil additive; analytical reagent for Cu, Ni; chelating agent; treatment of Wilson's disease. Triethylenetetramine is a selective CuII-chelator; crosslinking agent. Triethylenetetramine is undergoing trials for the treatment of heart failure in patients with diabetes.

Technology Process of Triethylenetetramine

There total 61 articles about Triethylenetetramine 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: 66.0%

→ triethylentetramine (112-24-3) + 1,4,7,10-tetraazacyclododecan (294-90-6)

Guidance literature:

Reference yield: 58.0%

C5H4NCH2(1-)*Cr(3+)*2(CH2NHCH2CH2NH2)2*2HCl=[C5H4NCH2Cr((CH2NHCH2CH2NH2)2HCl)2](2+) → 1,2-di-(3-pyridyl)-ethane (4916-58-9) + 3-Methylpyridine (108-99-6) + chromium(III) hexahydrate cation (14873-01-9) + triethylentetramine (112-24-3)

Guidance literature:

In perchloric acid; (N2); decompn. of Cr complex in 1 M HClO4 depending on temp. under anaerobic conditions; not isolated, monitored by UV; Kinetics;

Reference yield:

ethyleneimine (151-56-4,9002-98-6) + 3-azapentane-1,5-diamine (111-40-0,98824-35-2) → 2,2',2''-triaminotriethylamine (4097-89-6) + triethylentetramine (112-24-3)

Guidance literature:

With hydrogenchloride; In water; at 30 ℃; Kinetics; Thermodynamic data; acid-catalyzed ring opening reactions at various temperature, E_a, ΔH are given;

upstream raw materials:

ethanol

ethylenediamine

ethylene dibromide

1,2-ethanediamine monohydrate

Downstream raw materials:

1,3-bis-(2-benzylidenamino-ethyl)-2-phenyl-imidazolidine

triethylenetetramine-N,N,N',N'',N''',N'''-hexaacetic acid

1,1,4,7,10,10-hexamethyltriethylenetetramine

N-{2-[2-(2-amino-ethylamino)-ethylamino]-ethyl}-oleamide

Refernces

• 1、 Jonassen,Strickland. "-". . p. 312. Retrieved 1958.
• 2、 Abel, Anton S.,Averin, Alexei D.,Cheprakov, Andrey V.,Roznyatovsky, Vitaly A.,Denat, Franck,Bessmertnykh-Lemeune, Alla,Beletskaya, Irina P.. "6-Polyamino-substituted quinolines: Synthesis and multiple metal (CuII, HgII and ZnII) monitoring in aqueous media". . p. 4243 - 4260. Retrieved 2019.
• 3、 -. "PROCESS FOR PREPARING CYCLIC ALKYLENE UREAS". Page/Page column 14; 16-17. . Retrieved 2019/02/25.