6864-37-5

Basic information

• Product Name: Dimethyldicyane
• Synonyms: 3,3’-Dimethyl-4,4’-diaminodicyclohexylmethane;4,4’-methylenebis[2-methyl-cyclohexanamin;4,4’-methylenebis[2-methyl-Cyclohexanamine;BIS(4-AMINO-3-METHYLCYCLOHEXYL)METHANE;2,2'-DIMETHYL-4,4'-METHYLENEBIS(CYCLOHEXYLAMINE);4,4'-DIAMINO-3,3'-DIMETHYLDICYCLOHEXYLMETHANE;4,4'-METHYLENEBIS(1-AMINO-2-METHYLCYCLOHEXANE);4,4'-METHYLENEBIS(2-METHYLCYCLOHEXYLAMINE)
• CAS NO: 6864-37-5
• Molecular Formula: C₁₅H₃₀N₂
• Molecular Weight: 238.41
• EINECS: 229-962-1
• Product Categories: Nitrogen Compounds;Organic Building Blocks;Polyamines;ZX MACM
• Mol File: 6864-37-5.mol
• Article Data: 5

Chemical Properties

• Melting Point: -7°C
• Boiling Point: 93-100 °C(lit.)
• Flash Point: >230 °F
• Appearance: COLOURLESS TO YELLOW LIQUID
• Density: 0.94 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.08Pa at 20℃
• Refractive Index: n20/D 1.499(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: 3.6g/l
• PKA: 11.03±0.70(Predicted)
• Explosive Limit: 0.5-2.8%(V)
• Water Solubility: 2.01g/L at 20℃
• CAS DataBase Reference: Dimethyldicyane(CAS DataBase Reference)
• NIST Chemistry Reference: Dimethyldicyane(6864-37-5)
• EPA Substance Registry System: Dimethyldicyane(6864-37-5)

Safety Data

• Hazard Codes: T,C,N
• Statements: 22-23/24-35-51/53
• Safety Statements: 26-36/37/39-45-61
• RIDADR: UN 2927 6.1/PG 2
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 6864-37-5(Hazardous Substances Data)

Usage

Chemical Properties

Colorless transparent viscous liquid

Uses

Different sources of media describe the Uses of 6864-37-5 differently. You can refer to the following data:
1. 4,4′-Methylenebis(2-methylcyclohexylamine) (MMCA) may be used:in the synthesis of fully aliphatic polyimidesin the synthesis of fully aliphatic polyimide-siloxanes (APISiO)to prepare epoxy resin with trimethylolpropane triglycidyl ether, used for the characterization of the structural organization in dragline silk by transmission X-ray microscopy (STXM).
2. 4,4'-Methylenebis(2-methylcyclohexylamine) can be used as epoxy curing agents.

General Description

4,4′-Methylenebis(2-methylcyclohexylamine) is an alicyclic diamine.

Flammability and Explosibility

Nonflammable

Synthetic route

3,3'-dimethyl-4,4'-diaminodiphenylmethane (838-88-0) → bis-(4-amino-3-methylcyclohexyl)-methane (6864-37-5)

Conditions	Yield
With ruthenium on aluminium oxide; ammonium aluminium sulfate; hydrogen In tetrahydrofuran at 160℃; under 60006 Torr; for 4h; Acidic conditions; Large scale;	99.4%
With 1,4-dioxane; ruthenium(IV) oxide at 120 - 125℃; under 102971 - 154457 Torr; Hydrogenation;
With cobalt(III) oxide; sodium carbonate; calcium oxide at 200 - 220℃; under 110326 Torr; Hydrogenation;

3,3'-dimethyl-4,4'-diaminodiphenylmethane (838-88-0) → (4-amino-3-methylcyclohexyl)(4-amino-3-methylphenyl)methane (1201895-82-0) + bis-(4-amino-3-methylcyclohexyl)-methane (6864-37-5)

Conditions	Yield
With hydrogen; silica gel at 230℃; under 75007.5 - 202520 Torr; for 9h; Product distribution / selectivity; Autoclave; Inert atmosphere;

bis-(4-amino-3-methylcyclohexyl)-methane (6864-37-5) + 4-fluorobenzoyl chloride (403-43-0) → N,N'-bis(4-fluorobenzamide)-3,3'-dimethyldicyclohexyl methane

Conditions	Yield
With sodium dodecyl-sulfate; sodium hydroxide In dichloromethane; water at 5 - 10℃; for 8h;	82.7%

bis-(4-amino-3-methylcyclohexyl)-methane (6864-37-5) + terephthalaldehyde, (623-27-8) → C31H38N2O2

Conditions	Yield
In tetrahydrofuran at 70℃; for 27h; Inert atmosphere; Schlenk technique;	70%

1-Bromonaphthalene (90-11-9) + bis-(4-amino-3-methylcyclohexyl)-methane (6864-37-5) → C35H42N2

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene for 1h; Inert atmosphere; Reflux;	50%

formaldehyd (50-00-0) + bis-(4-amino-3-methylcyclohexyl)-methane (6864-37-5) → bis-(4-dimethylamino-3-methyl-cyclohexyl)-methane (97423-00-2)

Conditions	Yield
With methanol; water; nickel at 100℃; under 44130.5 Torr; Hydrogenation;

undec-10-enoyl chloride (38460-95-6) + bis-(4-amino-3-methylcyclohexyl)-methane (6864-37-5) → Undec-10-enoic acid [2-methyl-4-(3-methyl-4-undec-10-enoylamino-cyclohexylmethyl)-cyclohexyl]-amide (61796-67-6)

Conditions	Yield
With triethylamine
With triethylamine In tetrahydrofuran

C33H17Cl2N6O12S3(3-)*3Na(1+) + bis-(4-amino-3-methylcyclohexyl)-methane (6864-37-5) → C81H62Cl2N14O24S6(6-)*6Na(1+)

Conditions	Yield
With sodium hydroxide In water at 50 - 60℃; for 2h; pH=5.7 - 6.3;

1-(2-aminoethyl)pyrrolidine (7154-73-6) + 1-(2-aminoethyl)piperidine (27578-60-5) + aminoethylpiperazine (140-31-8) + 4-(2-AMINOETHYL)MORPHOLINE (2038-03-1) + 3-(2-Methyl-piperidino)-propylamin (25560-00-3) + 4-(3-Aminopropyl)morpholine (123-00-2) + 3-(1H-imidazol-1-yl)propan-1-amine (5036-48-6) + 1-(3-aminopropyl)-2-pyrrolidone (7663-77-6) + 5-(4-chlorophenyl)-2-furaldehyde (34035-03-5) + 4,4'-diaminodicyclohexylmethane (1761-71-3) + bis-(4-amino-3-methylcyclohexyl)-methane (6864-37-5) + 1-Aminopiperidine (2213-43-6) + 1-aminopyrrolidine hydrochloride (63234-71-9) + 1-azepanylamine (5906-35-4) + (S)-1-amino-2-(methoxymethyl)pyrrolidine (59983-39-0) + N-(2-aminoethyl)benzeneamine (1664-40-0) + (3R)-quinuclidin-3-amine dihydrochloride (6530-09-2, 119904-90-4, 120538-52-5, 123536-14-1, 124577-62-4, 126358-22-3, 137661-30-4, 137661-31-5) + N,N-dimethylethylenediamine (108-00-9) + 1-amino-3-(dimethylamino)propane (109-55-7) + 2-(2-AMINOETHYL)-1-METHYLPYRROLIDINE (51387-90-7) + 3-dibutylaminopropylamine (102-83-0) → C15H19ClN2O (849908-66-3) + C15H17ClN2O + C16H21ClN2O (849908-70-9) + C17H18ClN3O (940358-24-7) + C16H19ClN2O + C19H19ClN2O + C18H23ClN2O (849908-71-0) + C17H21ClN2O2 + C17H21ClN2O (849908-67-4) + C17H21ClN2O + C17H21ClN2O2 (880815-24-7) + C17H22ClN3O + C18H21ClN2O + C18H23ClN2O (849908-65-2) + C18H21ClN2O2 (932172-19-5) + N-((5-(4-chlorophenyl)furan-2-yl)methyl)-3-morpholinopropan-1-amine (875001-79-9) + C20H27ClN2O (849908-68-5) + C22H33ClN2O (849908-69-6) + C24H33ClN2O (849908-81-2) + C26H37ClN2O (849908-75-4)

Conditions	Yield
With polymer-bound trimethyl ammonium cyanoborohydride; acetic acid In 1,2-dichloro-ethane at 20℃; for 24 - 36h; Polystyrene; Combinatorial reaction / High throughput screening (HTS);

...Expand

bis-(4-amino-3-methylcyclohexyl)-methane (6864-37-5) + dianhydride of benzophenone-3,4,3',4'-tetracarboxy acid (2421-28-5) → Reaxys ID: 18804844

Conditions	Yield
In ISOPROPYLAMIDE at 150℃; for 2h;

bis-(4-amino-3-methylcyclohexyl)-methane (6864-37-5) + terephthalaldehyde, (623-27-8) → C43H48N4

Conditions	Yield
Multi-step reaction with 2 steps 1: tetrahydrofuran / 27 h / 70 °C / Inert atmosphere; Schlenk technique 2: 9 h / 70 °C / Schlenk technique; Inert atmosphere View Scheme

bis-(4-amino-3-methylcyclohexyl)-methane (6864-37-5) + but-2-enedioic acid diethyl ester (1520-50-9) → C31H54N2O8

Conditions	Yield
With oxygen at 25 - 50℃; for 12h; Reagent/catalyst; Temperature; Inert atmosphere;

Upstream product

• 838-88-0 3,3'-dimethyl-4,4'-diaminodiphenylmethane 

Downstream Products

• 97423-00-2 bis-(4-dimethylamino-3-methyl-cyclohexyl)-methane 
• 849908-66-3 C₁₅H₁₉ClN₂O 
• 849908-70-9 C₁₆H₂₁ClN₂O 
• 940358-24-7 C₁₇H₁₈ClN₃O 
• 849908-71-0 C₁₈H₂₃ClN₂O 
• 849908-67-4 C₁₇H₂₁ClN₂O 
• 880815-24-7 C₁₇H₂₁ClN₂O₂ 
• 849908-65-2 C₁₈H₂₃ClN₂O 
• 932172-19-5 C₁₈H₂₁ClN₂O₂ 
• 875001-79-9 N-((5-(4-chlorophenyl)furan-2-yl)methyl)-3-morpholinopropan-1-amine 
• 849908-68-5 C₂₀H₂₇ClN₂O 
• 849908-69-6 C₂₂H₃₃ClN₂O 
• 849908-81-2 C₂₄H₃₃ClN₂O 
• 849908-75-4 C₂₆H₃₇ClN₂O 

Relevant articles and documents

Method for preparing aliphatic amine through reduction of aromatic amine compound

The invention provides a method for preparing aliphatic amine through reduction of an aromatic amine compound. According to the method, the aromatic amine compound is taken as a reaction substrate, and is subjected to hydrogenation reaction with a supported ruthenium catalyst and a deamination retardant in a solvent, so that an aliphatic amine compound is obtained; the deamination retardant adoptsaluminum-containing inorganic salt. The method has the advantages that through the addition of the deamination retardant during catalytic hydrogenation reduction of aromatic amine, the frequency of deamination side reaction produced by target products is reduced, so that the yield of the target products is improved, and the production cost of the specific yield of the target products is reduced.By taking the preparation of PACM as an example, the yield of the target product PACM can reach greater than 98 percent, and the preparation method has an important application value for practical mass production in the industry.

METHOD OF CONVEYING LIQUIDS

The present invention relates to a method of continuously conveying a liquid which is used as starting material in a chemical reaction by means of a displacement pump having physically separate forward-transport valves and a liquid-filled bidirectional flow line between displacement pump and forward-transport valves, wherein an auxiliary liquid which is a product or a starting material of the chemical reaction and has a melting point which is below the melting point or below the saturation temperature of the liquid to be conveyed is present in the bidirectional flow line. The present invention additionally provides for the use of a product formed by hydrogenation of an aromatic compound as auxiliary liquid for conveying an aromatic compound and also the use of an alcohol or an ester derived from alcohol and carboxylic acid as auxiliary liquid for conveying carboxylic acids or carboxylic acid derivatives.

PROCESS FOR PREPARING CYCLOALIPHATIC AMINES

A process for preparing cycloaliphatic amines by hydrogenating the corresponding aromatic compounds with hydrogen-comprising gas at a temperature of from 30 to 280° C. and a pressure of 50-350 bar, in the presence of ruthenium catalysts. The hydrogenation is performed in the presence of from 1% by weight to 500% by weight, based on the catalyst calculated as elemental ruthenium (Ru), of suspended inorganic additives, and to the use of the cycloaliphatic amines as a synthesis unit.