Isophorone diamine (2855-13-2)

The IUPAC name of Isophorondiamine is 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine. With the CAS registry number 2855-13-2, it is also named as Cyclohexanemethanamine, 5-amino-1,3,3-trimethyl-. The product's categorie is organics and the other registry numbers are 116723-72-9, 129050-51-7, 177646-11-6, 25495-81-2, 45981-71-3, 50858-71-4, 52004-55-4 and 52697-24-2. It is faintly yellow liquid miscible with water. When heated, vapors may form explosive mixtures with air. Isophorondiamine should be stored in the cool and dry place.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 1.68; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -2.42; (4)ACD/LogD (pH 7.4): -2.4; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 2; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 3; (12)Molar Refractivity: 53.38 cm³; (13)Molar Volume: 195.6 cm³; (14)Polarizability: 21.16×10^-24 cm³; (15)Surface Tension: 33.4 dyne/cm; (16)Enthalpy of Vaporization: 45.36 kJ/mol; (17)Vapour Pressure: 0.135 mmHg at 25°C; (18)Rotatable Bond Count: 1; (19)Exact Mass: 170.178299; (20)MonoIsotopic Mass: 170.178299; (21)Topological Polar Surface Area: 52; (22)Heavy Atom Count: 12; (23)Complexity: 165.

Preparation of Isophorondiamine: It is obtained by the reaction of 3-cyano-3,5,5-trimethyl cyclohexanone and ammonia in catalyst of cobalt and hydrogen at the pressure of 15.2MPa (150ATM) and temperature of 120 °C. Or using three molecules of acetone to condense isophorone, and further using HCN addition
the double bond of Isophorone nitrile (3- cyano-3,5,5-trimethyl cyclohexanone). Then we get the product by reduction and amination in presence of the H₂. The following is the reaction equation:

Uses of Isophorondiamine: It is mainly used as epoxy curing agents. And it also can react with di-p-tolyl-oxalodiimidoyl dichloride to get p-Tolyl-(7,9,9-trimethyl-4-p-tolylamino-2,5-diazabicyclo[5.3.1]undec-2-eb-3-yl)-amine. This reaction needs reagent Et₃N at ambient temperature. The yield is 85%.



 

When you are using this chemical, please be cautious about it as the following:
It is harmful by inhalation and in contact with skin. And it is also harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) Avoid release to the environment.

People can use the following data to convert to the molecule structure.
1. SMILES:NCC1(CC(CC(N)C1)(C)C)C
2. InChI:InChI=1/C10H22N2/c1-9(2)4-8(12)5-10(3,6-9)7-11/h8H,4-7,11-12H2,1-3H3