4013-94-9

Basic information

• Product Name: N,N'-Diisopropylethylenediamine
• Synonyms: 1,2-Ethanediamine, N,N'-bis(1-methylethyl)-;n,n’-bis(1-methylethyl)-2-ethanediamine;N,N'-Disopropylethylene diamine;1,2-BIS-(ISOPROPYLAMINO)-ETHANE;N,N'-Diisopropylethylendiamine;N,N'-Diisopropylethylenediamine,97%;N,N''-DIISOPYLETHYEND DIAMINE;N,N'-Diisopropylethylenediamine
• CAS NO: 4013-94-9
• Molecular Formula: C₈H₂₀N₂
• Molecular Weight: 144.26
• EINECS: 223-666-6
• Product Categories: Amine Monomers;Monomers;Secondary Amines
• Mol File: 4013-94-9.mol

Chemical Properties

• Melting Point: 52°C (estimate)
• Boiling Point: 169-171 °C(lit.)
• Flash Point: 125 °F
• Appearance: clear colorless liquid
• Density: 0.798 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.4289(lit.)
• PKA: 10.46±0.29(Predicted)
• Water Solubility: Miscible with water.
• Sensitive: Hygroscopic
• BRN: 1735571
• CAS DataBase Reference: N,N'-Diisopropylethylenediamine(CAS DataBase Reference)
• NIST Chemistry Reference: N,N'-Diisopropylethylenediamine(4013-94-9)
• EPA Substance Registry System: N,N'-Diisopropylethylenediamine(4013-94-9)

Safety Data

• Hazard Codes: C
• Statements: 10-34
• Safety Statements: 16-26-27-36/37/39-45-25
• RIDADR: UN 2733 3/PG 3
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 4013-94-9(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless liquid

Uses

N,N'-Diethylethylenediamine is used in the preparation of 2-imidazolidinecarboxaldehydes and 1,4,6,9-tetraalkyl-1,4,6,9-tetraaza-5,10-dioxaperhydroanthracenes by reacting with glyoxal. It acts as a ligand and form coordination complexes with copper(II), which shows thermochromic properties.

Upstream product

• 107-15-3 ethylenediamine 
• 67-64-1 acetone 
• 24764-90-7 N,N'-diisopropyl-1,4-diaza-1,3-butadiene 
• 75-31-0 isopropylamine 
• 106-93-4 ethylene dibromide 
• 226068-74-2 N,N'-dibenzyl-N,N'-diisopropylethylenediamine 
• 75-26-3 isopropyl bromide 
• 107-06-2 1,2-dichloro-ethane 

Downstream Products

• 54966-00-6 N,N'-diisopropyl N,N'-dimethyl-1,2-ethanediamine 
• 1441135-80-3 C₂₆H₃₃BN₂Si 
• 1441135-85-8 C₂₆H₃₃BN₂Sn 
• 1441135-90-5 C₂₆H₃₃BN₂Pb 
• 1335231-37-2 GeCl(2,6-iPr₂C₆H₃NC₇H₈P(C₂H₄N₂(iPr)2)) 
• 1550176-73-2 N-(5-((isopropyl(2-(isopropylamino)ethyl)amino)methyl)-2-methylphenyl)-4-((5-methyl-4-(4-(trifluoromethoxy)phenyl)pyrimidin-2-yl)amino)benzamide 
• 1439937-79-7 3-benzyl-3-(trifluoromethyl)-1,4-diisopropylpiperazin-2-one 
• 217455-53-3 [Cu(acetylacetonate)(N,N'-diisopropylethylenediamine)]BPh₄ 
• 129920-20-3 1,3-diisopropyl-2-methyl-1,3,2-diazaborolidine 
• 7550-35-8 lithium bromide 
• 554-68-7 triethylamine hydrochloride 
• 92527-11-2 2-chloro-1,3-diisopropyl-1,3,2-diazaborolidine 
• 116907-13-2 risotilide hydrochloride 

Relevant articles and documents

Experimental and Theoretical Study of an Intramolecular CF3-Group Shift in the Reactions of α-Bromoenones with 1,2-Diamines

The reactions of trifluoromethylated 2-bromoenones and N,N′-dialkyl-1,2-diamines have been studied. Depending on the structures of the starting compounds, the formation of 2-trifluoroacetylpiperazine or 3-trifluoromethylpiperazine-2-ones was observed. The mechanism of the reaction is discussed in terms of multistep processes involving sequential substitution of bromine in the starting α-bromoenones and intramolecular cyclization of the captodative aminoenones as key intermediates to form the target heterocycles. The results of theoretical calculations are in perfect agreement with the experimental data. The unique role of the trifluoromethyl group in this reaction is demonstrated.

SATURATED N-HETEROCYCLIC CARBENE-LIGAND METAL COMPLEX DERIVATIVES, PREPARING METHOD THEREOF, AND PREPARING METHOD OF SILANE COMPOUND BY HYDROSILYLATION REACTION USING THE SAME AS CATALYST

Provided are a saturated N-heterocyclic carbene-ligand metal complex derivative, a method for preparing the same, and a method for preparing a silane compound by hydrosilylation using the same as a catalyst. To describe in more detail, the metal complex derivative has a saturated N-heterocyclic carbene derivative and an olefin ligand at the same time. A silane compound is prepared by hydrosilylation in the presence of the metal complex derivative as a catalyst. The provided metal complex derivative of the present invention has superior stability during hydrosilylation reaction and is capable of effectively performing the hydrosilylation reaction at low temperature even with small quantity. Further, a product with superior regioselectivity may be obtained. In addition, after the hydrosilylation reaction is completed, the metal complex derivative may be recovered and recycled.

SATURATED N-HETEROCYCLIC CARBENE-LIGAND METAL COMPLEX DERIVATIVES, PREPARING METHOD THEREOF, AND PREPARING METHOD OF SILANE COMPOUND BY HYDROSILYLATION REACTION USING THE SAME AS CATALYST

Provided are a saturated N-heterocyclic carbene-ligand metal complex derivative, a method for preparing the same, and a method for preparing a silane compound by hydrosilylation using the same as a catalyst. To describe in more detail, the metal complex derivative has a saturated N-heterocyclic carbene derivative and an olefin ligand at the same time. A silane compound is prepared by hydrosilylation in the presence of the metal complex derivative as a catalyst. The provided metal complex derivative of the present invention has superior stability during hydrosilylation reaction and is capable of effectively performing the hydrosilylation reaction at low temperature even with small quantity. Further, a product with superior regioselectivity may be obtained. In addition, after the hydrosilylation reaction is completed, the metal complex derivative may be recovered and recycled.

Reaction of 1,2-dibromoethane with primary amines: Formation of N,N′-disubstituted ethylenediamines RNH-CH2CH2-NHR and homologous polyamines RNH-[CH2CH2NR]n-H

The reaction of primary amines RNH2 (R: Me, Et, iPr, tBu and Ph) with 1,2-dibromoethane gave N,N′-disubstituted ethylenediamines R-NH-CH2CH2-NH-R (1) in yields ranging from 10% (1a; R=Me) to 70% (1d, R=tBu; 1e, R=Ph). Pipe

Design and synthesis of imidazoline derivatives active on glucose homeostasis in a rat model of type ii diabetes. 2. Syntheses and biological activities of 1,4-dialkyl-, 1,4-dibenzyl, and 1-benzyl-4-alkyl-2-(4',5'- dihydro-1'H-imidazol-2'-yl)piperazines and isosteric analogues of imidazoline

Piperazine derivatives have been identified as new antidiabetic compounds. Structure-activity relationship studies in a series of 1-benzyl- 4-alkyl-2-(4',5'-dihydro-1'H-imidazol-2'-yl)piperazines resulted in the identification of 1-methyl-4-(2',4'-dichlorobenzyl)-2-(4',5'-dihydro-1'H- imidazol-2'-yl)piperazine, PMS 812 (S-21663), as a highly potent antidiabetic agent on a rat model of diabetes, mediated by an important increase of insulin secretion independently of α2 adrenoceptor blockage. These studies were extended to find additional compounds in these series with improved properties. In such a way, substitution of both piperazine N atoms was first optimized by using various alkyl, branched or not, and benzyl groups. Second, some modifications of the imidazoline ring and its replacement by isosteric heterocycles were carried out, proceeding from PMS 812, to evaluate their influence on the antidiabetic activity. The importance of the distance between the imidazoline ring and the piperazine skeleton was studied third. Finally, the influence of the N-benzyl moiety was also analyzed compared to a direct N-phenyl substitution. The pharmacological evaluation was performed in vivo using glucose tolerance tests on a rat model of type II diabetes. The most active compounds were 1,4-diisopropyl-2-(4',5'-dihydro-1'H-imidazol-2'- yl)piperazine (41a), PMS 847 (S-22068), and 1,4-diisobutyl-2-(4',5'-dihydro- 1'H-imidazol-2'-yl)piperazine (41b), PMS 889 (S-22575), which strongly improved glucose tolerance without any side event or hypoglycemic effect. More particularly, PMS 847 proved to be as potent after po (100 μmol/kg) as after ip administration and appears as a good candidate for clinical investigations.

Method and apparatus for sunless tanning

Apparatus for simulating skin tanning comprises a receptacle containing a fluid comprising dihydroxyacetone, a receptacle containing a fluid comprising a secondary polyamine, and dispensing means for simultaneously or sequentially providing desired amounts of dihydroxyacetone and polyamine.

Carbanion-Accelerated Claisen Rearrangements. 8. Phosphonamide Anion-Stabilizing Groups

The utility of various phosphonamide groups has been examined in the context of the carbanion-accelerated Claisen rearrangement (CACR).An extensive survey has identified the N,N'-dibenzyl-1,3,2-diazaphospholidine group 11 to be optimal in the ease of construction of the CACR precursors and the facility and stereoselectivity of the rearrangement.Using n-butyllithium as the base, the phosphonamides rearranged readily at -20 deg C with complete regioselectivity and in good yield (74-79percent).The phosphonates also showed a high level of diastereoselectivity (>95percent de) but the yield from the (Z)-2-butenyl precursor (anti product) was only 45percent.A chiral N,N'-dibenzyl-1,3,2-diazaphospholidine 12 derived from trans-1,2-cyclohexanediamine was examined.Although the CACR proceeded very cleanly (71-85percent) and with high internal selectivity (94percent de), the relative asymmetric induction was poor (16-20percent de).This was also the case for a chiral N,N'-dibenzyl-1,3,2-diazaphosphorinane 15 derived from (R,R)-1,3-diphenyl-1,3-propanediamine and N,N'-dibenzyl-1,3,2-diazaphosphepine 16 derived from 6,6'-dimethyl-2,2'-diaminobiphenyl.The characteristic features of the CACR were compared with the aryl sulfone and phosphonate versions.

Glyoxal as Synthone, III. - A Simple Synthesis of Aminopyrroles and of Dihydropyrrolopyrroles

The alcoholysis of diazasilacyclopentenes 2, easily obtained from glyoxaldiimines 1 with alkali metal and dichlorosilanes, gives either 3-amino-substituted pyrroles 4 or, with only small amounts of alcohol, N-substituted dihydropyrrolopyrroles 5.Reduction of 1 with hydrogen in ethanol in the presence of small amounts of a Pd/C catalyst also gives 4 and 5, together with smaller quantities of a 3,4-diaminopyrrole 7.With more of the catalyst the formation of the 1,2-diaminoethanes 6 predominates.A single-crystal X-ray diffraction study was performed for the N,N'-di-tert-butyl derivative 5a, which confirms the expected centrosymmetric structure. - Keywords: Aminopyrroles / Diaminopyrroles / 1,4-Diaza-1,3-dienes / Glyoxal / Pyrrolopyrroles

BORANE-TETRAHYDROFURAN AS A USEFUL REAGENT IN THE N-MONOALKYLATION OF AMINES AND AMINOALCOHOLS BY CARBONYL COMPOUNDS.

A new procedure for the high-yield N-monoalkylation of primary aromatic and aliphatic amines is described.

Urea diisocyanate compositions

The present invention relates to stable solutions of urea diisocyanates in diisocyanates which are free from urea groups which solutions are prepared by a process which comprises reacting in the absence of a solvent at a temperature from about -20°C to about 80°C an organic diisocyanate with a bis-secondary diamine such that the NCO/NH-ratio is from 2.5 : 1 to 20 : 1. The solutions of the invention are well-suited for use as isocyanate component for the preparation of polyurethane resins by the isocyanate polyaddition process.