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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

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.

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.
  • Didodecanoylamides by reacting with (2S)-2-methyldodecanoyl chloride via acylation in the presence of sodium bicarbonate.
It can also be used as a hydrogen source in catalytic hydrogenation reactions.

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
BGBC4980V
BGBC3775V
BCBK2111V
1427332V
1427332

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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.
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
'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)

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