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66770

Sigma-Aldrich

Methylenediamine dihydrochloride

≥98.0% (AT)

Synonym(s):

Diaminomethane dihydrochloride

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About This Item

Linear Formula:
CH2(NH2)2 · 2HCl
CAS Number:
57166-92-4
Molecular Weight:
118.99
Beilstein:
3664689
EC Number:
260-602-6
MDL number:
MFCD00040377
UNSPSC Code:
12352100
PubChem Substance ID:
57652063
NACRES:
NA.22
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Assay

≥98.0% (AT)

form

solid

functional group

amine

storage temp.

2-8°C

SMILES string

Cl.Cl.NCN

InChI

1S/CH6N2.2ClH/c2-1-3;;/h1-3H2;2*1H

InChI key

QCYJCJJCNRIMNG-UHFFFAOYSA-N

General description

Methylenediamine dihydrochloride, also known as Diaminomethane dihydrochloride is an organic compound that is often utilized as a reagent and slow ammonia-releasing agent during the synthesis of primary amides of peptides and amino acids from active esters. [1]

Application

Methylenediamine dihydrochloride can be used as a reactant to synthesize:
  • Poly(methylene biguanides) via polycondensation reaction with sodium dicyanamide in the presence of 1-butanol[2].
  • Didodecanoylamides by reacting with (2S)-2-methyldodecanoyl chloride via acylation in the presence of sodium bicarbonate[3].
It can also be used as a hydrogen source in catalytic hydrogenation reactions[4].

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000124744
0000124744
0000302447
0000302447
0000294706

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Nickel-catalyzed transfer semihydrogenation and hydroamination of aromatic alkynes using amines as hydrogen donors
Reyes S, et al.
Organometallics, 30, 3340-3345 (2011)
Takaaki Sumiyoshi et al.
Journal of the American Chemical Society, 125(40), 12137-12142 (2003-10-02)
A series of 10 didodecanoylamides of alpha,omega-alkylidenediamines bridged by a straight carbon chain varying in length from 0 to 9 carbons was examined as possible gelator molecules of organic liquids to gain information on the relationships between the spacial arrangement
G Galaverna et al.
International journal of peptide and protein research, 42(1), 53-57 (1993-07-01)
Amide formation from acids, N-protected amino acids and peptides was achieved in an easy and convenient way by treating "active esters" such as succinimidyl or 4-nitrophenyl esters or acyl chlorides with diaminomethane dihydrochloride in dioxane in the presence of Et3N.
Poly(alkylene biguanides) as proton conductors for high-temperature PEMFCs.
Jochen Britz et al.
Advanced materials (Deerfield Beach, Fla.), 22(8), E72-E76 (2010-03-11)
'Passe-partout effect' in positive patch test reactions: a novel pattern of edge effect.
Esen Ozkaya
Contact dermatitis, 61(4), 245-247 (2009-10-15)

Questions

1–3 of 3 Questions  

  1. 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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  2. 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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  3. I am curious about where HCl is located and how it is bonded in the molecule.

    1 answer

    1. Both of the amino groups of the Methylenediamine are protonated (that is, as -NH3+ groups), with a chloride (Cl-) counterion associated with each of them. That is, it is best to think of the HCl as being dissociated, with H+ on the amine and Cl- as the counterion.

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