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Sigma-Aldrich

4,4′-Methylenebis(cyclohexylamine)

technical grade, 95%

Synonym(s):

4,4′-Diaminodicyclohexylmethane

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About This Item

Linear Formula:
CH2(C6H10NH2)2
CAS Number:
1761-71-3
Molecular Weight:
210.36
Beilstein:
2079179
EC Number:
217-168-8
MDL number:
MFCD00001496
UNSPSC Code:
12162002
PubChem Substance ID:
24862935
NACRES:
NA.23
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grade

technical grade

vapor pressure

<0.1 mmHg ( 38 °C)

Assay

95%

density

0.95 g/mL at 25 °C (lit.)

SMILES string

NC1CCC(CC1)CC2CCC(N)CC2

InChI

1S/C13H26N2/c14-12-5-1-10(2-6-12)9-11-3-7-13(15)8-4-11/h10-13H,1-9,14-15H2

InChI key

DZIHTWJGPDVSGE-UHFFFAOYSA-N

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General description

4,4′-Methylenebis(cyclohexylamine),also known as PACM (para-diaminodicyclohexylmethane), is an organic amine compoundcharacterized by the presence of two amine groups attached to adicyclohexylmethane backbone. It is primarily used as a hardener in epoxy resinformulations, where it plays a crucial role in cross-linking reactions,enhancing the mechanical properties and thermal resistance of the resultingmaterials. It has potential applications in the biomedical field, particularlyin the development of polymeric biomaterials. Its properties as a hardener inepoxy resin formulations allow for the creation of biocompatible materials thatcan be used in medical devices, implants, and tissue engineering scaffolds.

Application

4,4′-Methylenebis(cyclohexylamine) can be used as:
  • A curing agent for epoxy resins, facilitating the cross-linking process that leads to the formation of thermoset materials.
  • A key component in the synthesis of polyurethane elastomers, which have been investigated for their biocompatibility and mechanical properties, making them suitable for biomedical applications.
  • A monomer to synthesize porous organic polymers (POPs) via nucleophilic substitution reactions. These POPs are then tested for their ability to uptake iodine and for their fluorescence sensing performance related to dinitrophenol (DNP).

Signal Word

Danger

Hazard Statements

H302,H314,H317,H373,H411

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 2 - Skin Corr. 1B - Skin Sens. 1 - STOT RE 2 Oral

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

318.2 °F - closed cup

Flash Point(C)

159 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM6793
BCCK9888
BCCJ5738
BCCF1191
BCCD8853

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G L Kennedy
Journal of applied toxicology : JAT, 11(5), 367-371 (1991-10-11)
1,4-Bis(aminocyclohexyl)methane (PACM; CAS No. 1761-71-3) is a white solid considered for use in polymeric systems. PACM is moderately toxic systemically, with the acute oral lethal dose in rats between 670 and 1000 mg kg-1. PACM is a weak dermal sensitizer
Malin Frick et al.
Contact dermatitis, 48(6), 305-309 (2003-10-09)
From August 1999 to April 2001, there was an outbreak of severe eczema at a factory manufacturing medical equipment. A glue, mainly based on the isocyanate dicyclohexylmethane-4,4'-diisocyanate (DMDI), was suspected as being the cause of the problem. 16 workers with

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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