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Merck

8.03779

N,N-Dimethylethylenediamine

for synthesis

Synonym(s):

N,N-Dimethylethylenediamine, 2-(Dimethylamino)ethylamine, 1-Amino-2-dimethylaminoethane

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About This Item

Linear Formula:
NH2C2H4N(CH3)2
CAS Number:
108-00-9
Molecular Weight:
88.15
UNSPSC Code:
12352116
EC Index Number:
203-541-2
NACRES:
NA.22
MDL number:
MFCD00008175

Key Documents

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Product Name

N,N-Dimethylethylenediamine, for synthesis

SMILES string

N(CCN)(C)C

InChI

1S/C4H12N2/c1-6(2)4-3-5/h3-5H2,1-2H3

InChI key

DILRJUIACXKSQE-UHFFFAOYSA-N

vapor pressure

29 hPa ( 20 °C)

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

Quality Level

200

Analysis Note

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

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).



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.

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Danger

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Oral - Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1A

Storage Class

3 - Flammable liquids

wgk

WGK 1

flash_point_f

53.1 °F - closed cup

flash_point_c

11.7 °C - closed cup

Certificates of Analysis (COA)

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Global Trade Item Number

SKUGTIN
8.03779.010004022536383361

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