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D157805

Sigma-Aldrich

N,N′-Dimethylethylenediamine

98%

Synonym(s):

DMEDA, 1,2-Bis(methylamino)ethane

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R$491.00
25 G
R$2,418.00
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R$9,220.00
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Estimated to ship onMarch 29, 2025


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5 G
R$491.00
25 G
R$2,418.00
100 G
R$9,220.00
500 G
R$19,639.00

About This Item

Linear Formula:
CH3NHCH2CH2NHCH3
CAS Number:
Molecular Weight:
88.15
Beilstein:
878142
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
form:
liquid
Assay:
98%

R$491.00


Estimated to ship onMarch 29, 2025


Request a Bulk Order

Quality Level

Assay

98%

form

liquid

refractive index

n20/D 1.431 (lit.)

bp

119 °C (lit.)

density

0.819 g/mL at 20 °C (lit.)

SMILES string

CNCCNC

InChI

1S/C4H12N2/c1-5-3-4-6-2/h5-6H,3-4H2,1-2H3

InChI key

KVKFRMCSXWQSNT-UHFFFAOYSA-N

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Application

N,N′-Dimethylethylenediamine can be used as a ligand in the following processes:
  • Copper-catalyzed cyanations of aryl bromides using potassium hexacyanoferrate(II) to form the corresponding benzonitriles.[1]
  • Copper-catalyzed tandem reaction of carbodiimide and isocyanoacetate to form benzoimidazo[1,5-α]imidazoles.[2]
  • Aminothiolation of 1,1-dibromoalkene to form N-fused heterocycles.[3]
  • In combination with ferrous chloride, for the N-arylation of NH-sulfoximines with aryl iodides to form N-arylsulfoximines.[4]
  • It can catalyze the direct C-H arylation of unactivated benzene in the presence of potassium tert-butoxide to form the corresponding biaryl.[5]

Pictograms

FlameCorrosion

Signal Word

Danger

Hazard Statements

Hazard Classifications

Eye Dam. 1 - Flam. Liq. 3 - Skin Corr. 1B

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

78.8 °F - closed cup

Flash Point(C)

26 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

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An environmentally benign procedure for the Cu-catalyzed cyanation of aryl bromides.
Schareina T, et al.
Tetrahedron Letters, 46(15), 2585-2588 (2005)
Iron?Catalyzed C N Cross?Coupling of Sulfoximines with Aryl Iodides.
Correa A, et al.
Advanced Synthesis & Catalysis, 350(3), 391-394 (2008)
Copper-catalyzed synthesis of N-fused heterocycles through regioselective 1, 2-aminothiolation of 1, 1-dibromoalkenes.
Xu H, et al.
Organic Letters, 12(16), 3704-3707 (2010)
Organocatalysis in cross-coupling: DMEDA-catalyzed direct C? H arylation of unactivated benzene.
Liu W, et al.
Journal of the American Chemical Society, 132(47), 16737-16740 (2010)
Generation of benzoimidazo [1, 5-a] imidazoles via a copper-catalyzed tandem reaction of carbodiimide and isocyanoacetate.
Qiu G, et al.
Chemical Communications (Cambridge, England), 48(48), 6046-6048 (2012)

Articles

Buchwald phosphine ligands for C-C, C-N, and C-O bond formation.

Buchwald phosphine ligands for C-C, C-N, and C-O bond formation.

Questions

1–2 of 2 Questions  
  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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