Ethylenediamine Ethylenediamine
Structural formula
| Business number | 02UT |
|---|---|
| Molecular formula | C2H8N2 |
| Molecular weight | 60.12 |
| label |
1,2-Ethylenediamine, 1,2-diaminoethane, Diaminoethane, 1,2-ethylenediamine, Ethylenediamine, 1,2-Diaminoethane, 1,2-Ethanediamine, DAE, EDA |
Numbering system
CAS number:107-15-3
MDL number:MFCD00008204
EINECS number:203-468-6
RTECS number:KH8575000
BRN number:605263
PubChem number:24894420
Physical property data
1. Characteristics: Colorless or slightly yellow viscous liquid with an ammonia-like odor. [10]
2. pH value: 11.9 (25% solution, 25℃) [11]
3. Melting point (℃): 8.5[12]
4. Boiling point (℃): 116~117.2[13]
5. Relative density (water=1): 0.90 (20℃)[14]
6. Relative vapor density (air=1): 2.07[15]
7. Saturated vapor pressure (kPa): 1.43 (20℃) [16]
8. Heat of combustion (kJ/mol ): -1891.9[17]
9. Critical pressure (MPa): 6.48[18]
10. Alcohol/water partition coefficient: -2.04~-1.2[19]
11. Flash point (℃): 33.9 (OC); 43.3 (CC)[20 ]
12. Ignition temperature (℃): 385[21]
13. Explosion upper limit (%): 16.6[22]
14. Lower explosion limit (%): 2.7[23]
15. Solubility: soluble in water, Ethanol, insoluble in benzene, slightly soluble in ether. [24]
16. Viscosity (mPa·s, 15ºC): 1.722
17. Viscosity (mPa·s, 25ºC): 1.54
18. Viscosity (mPa·s, 30ºC): 1.226
19. Flash point (ºC, closed): 43.3
20. Flash point (ºC, open ): 33.9
21. Heat of evaporation (KJ/mol, 20ºC): 46.89
22. Heat of fusion (KJ/mol): 19.34
23. Heat of formation (KJ/mol): -26.63
24. Specific heat capacity (KJ/(kg·K), 30ºC, constant pressure): 2.95
25. Heat of solution (J/ mol,15ºC): 1.82
Toxicological data
1. Acute toxicity[25]
LD50: 1298mg/kg (rat oral); 730mg/kg (rabbit dermal )
LC50: 300mg/m3 (mouse inhalation)
2. Irritation [26]
Rabbit transdermal: 450mg, moderate stimulation (open stimulation test).
Rabbit eye: 675μg, severe irritation.
3. Subacute and chronic toxicity[27] Rats were repeatedly infected with this product at 1188mg/m3 Toxic, hair loss and lung, kidney, and liver damage were seen in animals; no damage was found after continuous exposure to 307 mg/m3 for 37 hours.
Ecological data
1. Ecotoxicity[28]<�Have the same reactivity. The iodination of phenol, aniline, tyrosine, pyrrole and hydroxybenzoic acid can occur in the DAE solution of KI3. The lithium and DAE system is a strong reducing system that can reduce alkenes, aromatic hydrocarbons, phenols and alcohols, etc.
Isomerization The lithium salt of DAE (LiNHCH2CH2NH2) is a very strong Base, commonly used in the dehydrogenation and aromatization of vinylcyclohexene derivatives. Terminal olefins can be quickly and quantitatively isomerized into internal olefins, and the triple bond can also migrate to the chain end position (Formula 1)[2]. In DAE, sodium amide causes a similar migration of triple bonds. 
DAE can react with electrophiles to form single or double derivatives. DAE can be used as a symmetrical building block to form 1,2-diamino, 1,2-diamino, 1,2-diamidino, diimide or dimethylene to connect molecular fragments (Formula 2) [3].
In a two-atom heterocyclic system DAE is a very good reagent in the synthesis of . A similar reaction with 1-halogenated alkynes can produce 2-alkylene imidazoline or 2-alkylimidazoline. DAE reacts with R(W)C=CX2 type compounds to form substituted 2-methylene imidazoline (Formula 3)[4]. DAE reacts with acid, ester, amide, dithioester, imino, nitrile, 2-arylazoline or 2-phenylthiazolium salt to generate 2-substituted imidazoline (formula 4)[5].
DAE and CS2 The reaction can generate imidazoline-2-thiol. The three-step reaction between DAE and acetic acid can generate 2-methylimidazole. DAE reacts with O-alkylthiocarbamates or N-alkyldithiocarbamates to form cyclic guanidines. These compounds can also be prepared by reacting imino halides or dialkylthioacetals of isothiocyanates with DAE (Formula 5)[6].
DAE and dialdehydes and diketones , dicarboxylic acid and its derivatives react to form a cyclic compound (Formula 6) including (N-C-C-N) fragments[7]. 1,2-Dicarbonyl compounds (α-diketone, o-quinone, alkyl oxalate) will generate dihydropyrazine, and then epoxidation reaction will generate pyrazine.
A molecule with two reaction points Reacts with DAE to form bicyclic products (Formula 7, Formula 8)[8,9]. Heterocycles prepared by this method include pyrrole [1,2-a]imidazole, imidazole [3,4-a]imidazole, imidazole [1,2-b]quinoline, imidazole [1,2-c]pyrimidine, etc.
6. Used for organic synthesis and Preparation of pesticides, reactive dyes, medicines, epoxy resin curing agents, etc. [36]
