100-36-7

Basic information

• Product Name: N,N-Diethylethylenediamine
• Synonyms: DEAEA;(DIETHYLAMINO)ETHYLAMINE;BETA-DIETHYLAMINOETHYLAMINE;1-AMINO-2-(DIETHYLAMINO)ETHANE;2-(DIETHYLAMINO)ETHYLAMINE;2-aminoethyldiethylamine;N,N-DIETHYLETHYLENEDIAMINE;N,N-DIETHYL-1,2-ETHANEDIAMINE
• CAS NO: 100-36-7
• Molecular Formula: C₆H₁₆N₂
• Molecular Weight: 116.2
• EINECS: 202-844-7
• Product Categories: synthetic organic intermediate
• Mol File: 100-36-7.mol

Chemical Properties

• Melting Point: <-70°C
• Boiling Point: 145-147 °C(lit.)
• Flash Point: 87 °F
• Appearance: Clear colorless to light yellow/Liquid
• Density: 0.827 g/mL at 25 °C(lit.)
• Vapor Pressure: 5.56mmHg at 25°C
• Refractive Index: n20/D 1.436(lit.)
• Storage Temp.: Flammables area
• PKA: pK1:7.70(+2);pK2:10.46(+1) (25°C)
• Explosive Limit: 0.7-8.4%(V)
• Water Solubility: MISCIBLE
• Sensitive: Air Sensitive
• BRN: 605299
• CAS DataBase Reference: N,N-Diethylethylenediamine(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-Diethylethylenediamine(100-36-7)
• EPA Substance Registry System: N,N-Diethylethylenediamine(100-36-7)

Safety Data

• Hazard Codes: C,Xi
• Statements: 10-20/21/22-35-21-36/37/38-34
• Safety Statements: 26-36/37/39-45-25-16-36-27
• RIDADR: UN 2685 8/PG 2
• WGK Germany: 1
• RTECS: KV3500000
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 100-36-7(Hazardous Substances Data)

Usage

Chemical Properties

CLEAR COLORLESS TO LIGHT YELLOW LIQUID

Uses

Different sources of media describe the Uses of 100-36-7 differently. You can refer to the following data:
1. N,N-Diethylethylenediamine is used in the syntheses of anti-malarials. In addition, it has been seem to induce apoptosis through a caspase-3 dependent pathway.
2. N,N-Diethylethylenediamine was used in the oxidative amidation of hydrogen phosphonate diesters in the synthesis of oligonucleotides. It is also used to develop melanin targeted PET and single-photon emission computed tomography (SPECT) imaging agents for melanoma.

Flammability and Explosibility

Flammable

Safety Profile

Poison by intraperitoneal route. Moderately toxic by ingestion and skin contact. A slun and severe eye irritant. Flammable liquid when exposed to heat or flame; can react with oxidzing materials. To fight fire, use alcohol foam, CO2, dry chemical. When heated to decomposition it emits toxic fumes of NOx. See also AMINES.

InChI:InChI=1/C6H16N2/c1-3-8(4-2)6-5-7/h3-7H2,1-2H3/p+2

Upstream product

• 574-98-1 2-(2-bromoethyl)isoindoline-1,3-dione 
• 109-89-7 diethylamine 
• 100-97-0 hexamethylenetetramine 
• 100-35-6 2-(diethylamino)ethyl chloride 
• 74-85-1 ethene 
• 107-15-3 ethylenediamine 
• 3010-02-4 diethylaminoacetonitrile 
• 150-77-6 N,N,N',N'-Tetraethylethylenediamine 
• 64-17-5 ethanol 
• 869-24-9 2-chloro-N,N-diethylethylamine hydrochloride 
• 151-56-4 ethyleneimine 
• 83742-04-5 β-Diethylaminopropionhydrazid 
• 5351-01-9 methyl 3-(N,N-diethylamino)propionate 
• 15855-37-5 N,N-diethyl-N'-benzylethylenediamine 

Downstream Products

• 24426-16-2 N,N-diethyldiethylenetriamine 
• 23826-73-5 N,N-diethyl-N'-[2]pyridyl-ethylenediamine 
• 91087-51-3 N-(2-Diethylamino-ethyl)-succinimid 
• 131203-41-3 2-(2-(N,N-diethylamino)ethyl)amino-1-phenylethanol 
• 6011-13-8 Isonicotinsaeure-(2-diethylamino-ethylamid) 
• 811868-36-7 N,N-diethyl-N'-(2,6-dimethyl-pyrimidin-4-yl)-ethylenediamine 
• 811868-32-3 N⁴-(2-diethylamino-ethyl)-2-methyl-pyrimidine-4,6-diyldiamine 
• 856972-91-3 6-chloro-N⁴-(2-(diethylamino)ethyl)pyrimidine-2,4-diamine 
• 859064-95-2 2,4-Diamino-6-(2-diethylamino-ethylamino)-pyrimidin 
• 6821-06-3 2-(2-diethylaminoethyl)-1H-isoindole-1,3(2H)-dione 
• 87864-14-0 2-chloro-quinoline-4-carboxylic acid-(2-diethylamino-ethylamide) 
• 110248-70-9 N,N-diethyl-N'-[8-(4-chloro-benzyl)-nortropane-3endo-yl]-ethylenediamine 
• 2716-99-6 N-[2-(diethylamino)ethyl]-2-ethoxyquinoline-4-carboxamide 
• 5470-29-1 (2-diethylamino-ethyl)-carbamic acid ethyl ester 

Relevant articles and documents

The synthesis of asymmetric ethylenediamine derivatives catalyzed by ion-exchange resins

The ring-opening reaction of aziridine with alkylamines over a series of ion-exchange resins was investigated. Among these catalysts, D001-CC exhibited excellent catalytic performance. The catalysts were characterized by SEM and N2 adsorption-desorption. The results indicated that the selectivity of N,N-diethylethylenediamine mainly depended on the acidity and S BET of the resins. Strong Br?nsted acid sites played an important role on the conversion of aziridine, and the distribution of acid sites on catalyst had a significant effect on the selectivity of N,N-diethylethylenediamine. The reaction parameters, such as reaction time, molar ratio, reaction temperature, and catalyst loading, were also optimized and N,N-diethylethylenediamine was obtained in an excellent yield of 97 %. Furthermore, D001-CC was efficiently recycled five times by simple treatment with large amounts of deionized water and mineral acid. Finally, a series of asymmetric ethylenediamine derivatives were successfully synthesized with this method. Therefore, a simple and versatile process for the synthesis of asymmetric ethylenediamine derivatives has been established over ion-exchange resins.

New pyrido[3,4-g]quinazoline derivatives as CLK1 and DYRK1A inhibitors: synthesis, biological evaluation and binding mode analysis

Cdc2-like kinase 1 (CLK1) and dual specificity tyrosine phosphorylation-regulated kinase 1A (DYRK1A) are involved in the regulation of alternative pre-mRNA splicing. Dysregulation of this process has been linked to cancer progression and neurodegenerative diseases, making CLK1 and DYRK1A important therapeutic targets. Here we describe the synthesis of new pyrido[3,4-g]quinazoline derivatives and the evaluation of the inhibitory potencies of these compounds toward CDK5, CK1, GSK3, CLK1 and DYRK1A. Introduction of aminoalkylamino groups at the 2-position resulted in several compounds with low nanomolar affinity and selective inhibition of CLK1 and/or DYRK1A. Their evaluation on several immortalized or cancerous cell lines showed varying degree of cell viability reduction. Co-crystal structures of CLK1 with two of the most potent compounds revealed two alternative binding modes of the pyrido[3,4-g]quinazoline scaffold that can be exploited for future inhibitor design.

Preparation method for high-yield N, N-diethylethylenediamine

The invention discloses a preparation method for high-yield N, N-diethylethylenediamine. The method comprises the following steps that 2-diethylaminoethylchloride hydrochloride and benzyl carbamate are added into a sodium hydroxide solution, a palladium-carbon catalyst is added, heating is carried out so as to reach 55-65 DEG C for reaction for 4-7 hours under a sealed condition, alkali is added into reaction liquid for cooling and alkali precipitation, lower-layer alkali liquor and the palladium-carbon catalyst are separated, an organic layer is subjected to rectification treatment, and a fraction of 142-148 DEG C is collected so as to obtain the N,N-diethylethylenediamine. The method has the advantages that the reaction conditions are mild, no harmful gas is adopted or generated in the reaction process, and meanwhile, the yield of the N,N-diethylethylenediamine is high.

Preparation method of N,N-diethylenediamine

The invention belongs to the technical field of chemical synthesis and relates to a preparation method of N,N-diethylenediamine. The preparation method of the N,N-diethylenediamine comprises the following steps: (1) preparing 2-diethylamine-based chloroethane hydrochloride: performing heat-preserving reaction on a chlorinating agent and diethylamine ethanol in a reaction solvent, concentrating a reaction solvent after the heat-preserving reaction, adding low molecular alcohol or ester after concentrating, performing recrystallization to obtain a 2-2-diethylamine-based chloroethane hydrochloride wet product and drying to obtain a 2-diethylamine-based chloroethane hydrochloride dry product; (2) preparing the N,N-diethylenediamine: performing heat-preserving and pressure-maintaining reactionon the 2-diethylamine-based chloroethane hydrochloride and excessive liquid ammonia for more than or equal to 4 hours under the conditions that the pressure is 0 to 10 MPa and the temperature is 10 to100 DEG C, recycling the residual ammonia gas after the reaction, adding alkali into the reaction liquid, performing cooling alkali analysis, separating out the lower layer of alkaline liquid, rectifying an organic layer and collecting the fraction with the temperature of 143 to 148 DEG C, to obtain the N,N-diethylenediamine. The N,N-diethylenediamine prepared according to the method provided bythe invention has the advantages of high yield, high content, simplicity in operation, low raw material cost and the like.

Isoflavone amide type derivative, preparation method and medical application thereof

The invention relates to the field of medicinal chemistry, and relates to an isoflavone amide type derivative, a preparation method and a medical application thereof, in particular to an isoflavone amide type derivative with the general formula (I), a preparation method thereof, medicine compositions including the isoflavone amide type derivative and a medical application thereof, especially an application of the isoflavone amide type derivative as a medicine for preventing or curing hyperlipemia, obesity or type II diabetes. The general formula (I) is shown in the description.

Synthesis and characterization of N-substitutional ethylenediamine derivatives

N-Substituted and N,N-disubstituted ethylenediamine derivatives were prepared rapidly in aqueous conditions from 30 to 76 % yields, respectively, on a multi-gram scale starting from inexpensive and commercially available starting materials. The steps involved Michael addition, hydrazinolysis and Curtius rearrangements. The highlight of this method lies on its convenience and economy in accessing these intermediates.

QUINAZOLINE DERIVATIVES AS A MULTIPLEX INHIBITOR AND METHOD FOR THE PREPARATION THEREOF

The present invention relates to a novel quinazoline derivative and a pharmaceutically acceptable salt thereof as a multiplex inhibitor, a method for the preparation thereof, and a pharmaceutical composition and a therapeutic composition comprising same as an active ingredient. The inventive quinazoline derivative as a multiplex inhibitor can selectively and effectively inhibit diseases caused by the overactivity of a tyrosine kinase.

METHOD FOR PRODUCING N-MONOALKYL-SUBSTITUTED ALKYLENE AMINE

PROBLEM TO BE SOLVED: To provide a method for producing an N-monoalkyl-substituted alkylene amine especially useful for uses such as medicine intermediates, agrochemical intermediates, urethane resin-foaming catalysts, surfactants and the like among alkyl-substituted alkylene amine compounds from an alcohol and an alkylene amine as raw materials. SOLUTION: This method for producing the N-monoalkyl-substituted alkylene amine is characterized by reacting the alkylene amine with a ≥2C alkyl alcohol in the presence of a copper-containing oxide catalyst system. The N-monoalkyl-substituted alkylenamine is produced in high conversion and in N-monoalkylation selectivity.

Pharmaceutically active pyrrolidine derivatives as bax inhibitors

The present invention is related to new substituted pyrrolidine derivatives of formula (I). Said compounds are preferably for use as pharmaceutically active compounds. Specifically, pyrrolidine derivatives of formula (I) are useful in the treatment and/or prevention of neurodegenerative disorders, diseases associated with polygultamine tracts, epilepsy, ischemia, infertility, cardiovascular disorders renal hypoxia, hepatitis and AIDS. Said pyrrolidine derivatives display a modulatory and most notably a down-regulating-up to an inhibitory-activity with respect to the cellular death agonist Bax and/or the activation pathways leading to Bax and allows therefore to block the release of cytochrome (c). The present invention is furthermore related to novel pharmaceutically activity substituted pyrrolidine derivatives as well as to methods of their preparation, wherein X is selected from the group consisting of O, S, CRR, NOR, NNRR; A is selected from the group consisting of —(C═O)—, —(C═O)—O—, —C(═NH)—, —(C═O)—NH—, —(C═S)—NH, —SO2-, —SO2NH—; —CH2-; B is either a group —(C═O)—NRR or represents a heterocyclic residue having the formula (II) wherein Q is NR, O or S; n is an integer selected of 0, 1 or 2; Y, Z and E form together with the 2 carbons to which they are attached a 5-6 membered aryl or heteroaryl ring.

Pharmaceutically active pyrrolidine derivatives

The present invention is related to pyrrolidine derivatives of formula (I). Said compounds are preferably for use as pharmaceutically active compounds. Specifically, pyrrolidine derivatives of formula (I) are useful in the treatment and/or prevention of premature labor, premature birth and dysmenorrhea. In particular, the present invention is related to pyrrolidine derivatives displaying a substantial modulatory, notably an antagonist activity of the oxytocin receptor. More preferably, said compounds are useful in the treatment and/or prevention of disease states mediated by oxytocin, including premature labor, premature birth and dysmenorrhea. The present invention is furthermore related to novel pyrrolidine derivatives as well as to methods of their preparation, wherein X is selected from the group consisting of CR6R7, NOR6, NNR6R7; A is selected from the group consisting of —(C═O)—, —(C═O)—O—, —C(═NH)—, —(C═O)—NH—, —(C═S)—NH, —SO22—, —SO2NH—, —CH2—,B is either a group —(C═O)—NR8R9 or represents a heterocyclic residue having the formula (a) wherein Q is NR10, O or S; n is an integer selected of 0, 1 or 2; Y, Z and E form together with the 2 carbons to which they are attached a 5-6 membered aryl or heteroaryl ring.