8.03779

N,N-Dimethylethylenediamine

for synthesis

• Synonyme(s) : N,N-Dimethylethylenediamine, 2-(Dimethylamino)ethylamine, 1-Amino-2-dimethylaminoethane
• Formule linéaire : NH₂C₂H₄N(CH₃)₂
• Numéro CAS: 108-00-9
• Poids moléculaire : 88.15
• UNSPSC Code: 12352116
• EC Index Number: 203-541-2
• NACRES: NA.22
• MDL number: MFCD00008175
• Assay: ≥98.0% (GC)

Propriétés

• vapor pressure: 29 hPa ( 20 °C)
• Quality Segment: 200
• assay: ≥98.0% (GC)
• autoignition temp.: 225 °C
• potency: 1135 mg/kg LD₅₀, oral (Rat)
• expl. lim.: 1.3-10.8 % (v/v)
• pH: 11.4 (20 °C, 10 g/L in H₂O)
• bp: 107-109 °C/1013 hPa
• mp: <-70 °C
• transition temp: flash point 12.5 °C
• density: 0.81 g/cm³ at 20 °C
• storage temp.: 2-30°C
• SMILES string: N(CCN)(C)C
• InChI: 1S/C4H12N2/c1-6(2)4-3-5/h3-5H2,1-2H3
• InChI key: DILRJUIACXKSQE-UHFFFAOYSA-N

Description

General description

N,N-Dimethylethylenediamine (DMEDA) is used as a bidentate ligand in coordination chemistry due to the presence of two nitrogen atoms, one with lone pairs that can coordinate to a metal center. It is used as a ligand and base in Suzuki-Miyaura and Sonogashira coupling reactions, enhancing palladium catalyst stability, and deprotonating alkynes. It acts as a nucleophile and a base, promoting reactions involving proton transfer or nucleophilic attack. It is commonly used in amination reactions to synthesize substituted amines and in epoxide ring openings to form amino alcohols. Additionally, DMEDA serves as a chelating agent, forming stable complexes with transition metals. It acts as a secondary amine in reductive amination to synthesize tertiary amines.

Application

• N, N′, N′′ versus N, N′, O imine-containing coordination motifs: ligand-directed synthesis of mononuclear and binuclear CuII compounds: This study explores ligand-directed synthesis involving N,N-dimethylethylenediamine in copper compounds (RE Ferraz de Paiva et al., 2017).



• Reversible interconversion between methanol-diamine and diamide for hydrogen storage based on manganese catalyzed (de)hydrogenation: Research on the dehydrogenative condensation of methanol and N,N-dimethylethylenediamine for hydrogen storage (Z Shao et al., 2020).



• Influence of water vapor and acid gases on CO2 adsorption using N,N-dimethylethylenediamine decorated Cu-BTC: This article investigates the effects of environmental factors on the adsorption efficiency of Cu-BTC decorated with N,N-dimethylethylenediamine (F Song et al., 2019).



• Triple chemical derivatization strategy assisted liquid chromatography-mass spectrometry for determination of retinoic acids in human serum: A study on the chemical derivatization involving N,N-dimethylethylenediamine for analyzing retinoic acids in serum (GG Gong et al., 2022).



• Silicoaluminophosphate molecular sieve DNL-6: Synthesis with a novel template, N, N′-dimethylethylenediamine, and its catalytic application: Discusses the synthesis and catalytic applications of a molecular sieve developed using N,N′-dimethylethylenediamine as a template (P Wu et al., 2018).

Analysis Note

Assay (GC, area%): ≥ 98.0 % (a/a)
Density (d 20 °C/ 4 °C): 0.806 - 0.809
Identity (IR): passes test

Informations sur la sécurité

• pictograms: GHS02,GHS05,GHS07
• signalword: Danger
• hcodes: H225 - H302 + H312 - H314
• pcodes: P210 - P233 - P280 - P301 + P312 - P303 + P361 + P353 - P305 + P351 + P338
• Hazard Classifications: Acute Tox. 4 Dermal - Acute Tox. 4 Oral - Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1A
• Classe de stockage: 3 - Flammable liquids
• wgk: WGK 1
• flash_point_f: 53.1 °F - closed cup
• flash_point_c: 11.7 °C - closed cup