Catalog Number
ACM101779-1
Product Name
4,4'-Diaminodiphenylmethane
Category
Monomers; Polymers
Description
4,4'-diaminodiphenylmethane appears as a tan flake or lump solid with a faint fishlike odor. May be toxic by inhalation or ingestion, and may be irritating to skin. Insoluble in water.;DryPowder; Liquid; OtherSolid; OtherSolid, Liquid;Solid;COLOURLESS-TO-PALE-YELLOW FLAKES WITH CHARACTERISTIC ODOUR. TURNS DARK ON EXPOSURE TO AIR.;Pale-brown, crystalline solid with a faint, amine-like odor.;Pale-brown, crystalline solid with a faint, amine-like odor.
IUPAC Name
4-[(4-aminophenyl)methyl]aniline
Molecular Weight
198.26g/mol
Molecular Formula
C13H14N2;NH2C6H4CH2C6H4NH2;C13H14N2
Canonical SMILES
C1=CC(=CC=C1CC2=CC=C(C=C2)N)N
InChI
InChI=1S/C13H14N2/c14-12-5-1-10(2-6-12)9-11-3-7-13(15)8-4-11/h1-8H,9,14-15H2
InChI Key
YBRVSVVVWCFQMG-UHFFFAOYSA-N
Boiling Point
748 to 750 °F at 768 mm Hg (NTP, 1992);398.0 °C;398 °C;at 102kPa: 398-399 °C;748°F;748°F
Melting Point
197 to 198 °F (NTP, 1992);92.5 °C;92.5 °C;92.5°C;91.5-92 °C;198°F;198°F
Flash Point
430 °F (NTP, 1992);428 °F (220 °C) (closed cup);220 °C c.c.;430°F;374°F
Density
1.15 at 77 °F (NTP, 1992);1.070 g/mL at 103 °C;0.5 g/cm³;1.15;1.06 (Liquid at 212°F)
Solubility
less than 1 mg/mL at 66° F (NTP, 1992);0.01 M;Slightly sol in cold water. Very sol in alcohol, benzene, ether;Solubility (g/100mL solvent at 25 °C): 273.0 in acetone; 9.0 in benzene; 0.7 in carbon tetrachloride; 9.5 in ethyl ether; 143.0 in methanol; 0.1 in water;In water, 1.00X10+3 mg/L at 25 °C;1 mg/mL at 25 °C;Solubility in water: poor;0.1%
Application
4,4'-Diaminodiphenylmethane serves primarily as a chemical intermediate in industrial applications, notably in the production of isocyanates and polyisocyanates, which are essential for manufacturing polyurethane foams used for insulation and various other coatings. It acts as a cross-linking agent for epoxy resins and is involved in producing azo dyes. Additionally, this compound finds applications as a curing agent for both epoxy resins and urethane elastomers and serves critical roles in the rubber industry, such as a curative for neoprene, a rubber additive, and an anti-frosting agent in footwear. Beyond its uses in chemicals and polymers, 4,4'-Diaminodiphenylmethane is incorporated in products like adhesives, laminates, paints, and spandex, alongside roles in preventing corrosion and in the creation of poly(amide-imide) resins for magnet wire enamels. It is also employed in the manufacture of diverse items, including eyeglass frames, plastic jewelry, electric encapsulators, and shoe soles. Despite its utility, it's important to handle 4,4'-Diaminodiphenylmethane with care, due to its potential health risks, including skin and eye irritation, liver damage, and its classification as a probable human carcinogen.
Color/Form
Crystals from water or benzene;Tan flakes, lumps, or pearly leaflets from benzene;Plates or needles (water); plates (benzene);Light-brown crystals;Light tan to white crystalline solid
Covalently-Bonded Unit Count
1
Exact Mass
198.115698g/mol
Heat of Vaporization
95.4 kJ/mol
Log P
1.59 (LogP);log Kow = 1.59;1.59;1.6
MeSH Entry Terms
4,4'-diaminodiphenylmethane;4,4'-diaminodiphenylmethane dihydrochloride;4,4'-diaminodiphenylmethane, sodium chloride (3:1);4,4'-MDA;4,4'-methylene dianiline;4,4'-methylenebisaniline;4,4'-methylenedianiline;di(4-aminophenyl)methane;p,p'-diaminodiphenylmethane;Tonox
Monoisotopic Mass
198.115698g/mol
Odor
Faint, amine-like odor
Other Experimental
Molar heat capacity: 270.9 J/mol-K;BP: 257 °C at 18 mm Hg; 249-253 °C at 15 mm Hg; 232 °C at 9 mm Hg;Reacts similarly to other aromatic amines. Heat of fusion: 19.6 kJ/mol. Specific heat: 2.1 J/g-deg C;Henry's Law constant = 5.3X10-11 atm-cu m/mol at 25 °C (est);Hydroxyl radical reaction rate constant = 3.00X10-11 cu cm/molec-sec at 25 °C
Stability
OXIDIZES IN AIR; PALE YELLOW CRYSTALS TURN DARK COLOR WHEN EXPOSED TO AIR.
UN Number
2651;2651;2651;2651
Vapor Density
6.8 (NTP, 1992) (Relative to Air);6.8 (Air = 1);6.8
Vapor Pressure
1e-07 mm Hg at 77 °F (calculated) (NTP, 1992);2.03X10-7 mm Hg at 25 °C;Vapor pressure, Pa at 197 °C: 133;0.0000002 mmHg at 77°F;(77°F): 0.0000002 mmHg
Viscosity
8.3 cP at 100 °C
