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1,4-Cyclohexanebis(methylamine)
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Name

1,4-Cyclohexanebis(methylamine)

 EINECS 219-840-6
CAS No. 2549-93-1 Density 0.94
PSA 52.04000 LogP 2.11080
Solubility SOLUBLE Melting Point -9 °C
Formula C8H18 N2 Boiling Point 240-245 ºC
Molecular Weight 142.244 Flash Point 107 ºC
Transport Information N/A Appearance clear colorless to slightly yellow liquid
Safety Moderately toxic by ingestion and skin contact. A severe skin irritant. When heated to decomposition it emits toxic fumes of NOx. Risk Codes R21/22;R34   
Molecular Structure Molecular Structure of 2549-93-1 (1,4-Cyclohexanebis(methylamine)) Hazard Symbols
Synonyms

1,4-Cyclohexanebis(methylamine)(6CI,7CI,8CI); 1,4-Bis(aminomethyl)cyclohexane; 1,4-Cyclohexanedimethylamine;1,4-Cyclohexylenebis(methylamine); 1,4-Di(aminomethyl)cyclohexane;Hexahydro-p-xylylenediamine; [[4-(Aminomethyl)cyclohexyl]methyl]amine;p-Bis(aminomethyl)cyclohexane

Article Data 19

1,4-Cyclohexanebis(methylamine) Synthetic route

10534-13-1

cyclohexane-1,4-dicarbonitrile

2549-93-1

1,4-bis-(aminomethyl)cyclohexane

Conditions
ConditionsYield
With ammonium hydroxide; hydrogen In methanol at 80℃; under 33753.4 Torr; for 4h;97%
With ammonium hydroxide; hydrogen In methanol at 80℃; under 33753.4 Torr;97%
With hydrogen In ethanol at 95℃; under 37503.8 Torr; for 0.5h; Temperature;90%
With hydrogen In ethanol at 95℃; under 37503.8 Torr; for 0.5h;
With hydrogen In ethanol at 95℃; under 37503.8 Torr; for 0.5h;
33424-83-8

1,4-cyclohexanedicarboxaldehyde

55309-54-1

cis/trans-1,3-cyclohexanedicarboxaldehyde

A

280-70-6

3-azabicyclo<3.3.1>nonane

B

2549-93-1

1,4-bis-(aminomethyl)cyclohexane

C

2579-20-6

cis, trans-1,3-dimethylaminocyclohexane

Conditions
ConditionsYield
Stage #1: 1,4-cyclohexanedicarboxaldehyde; cis/trans-1,3-cyclohexanedicarboxaldehyde With ammonia In methanol at 100℃; for 0.666667 - 0.75h;
Stage #2: With hydrogen; Ni catalyst supported on silica/alumina In methanol at 100℃; under 41372.9 Torr; for 5h; Product distribution / selectivity;		A 27%
B n/a
C n/a
With ammonia; hydrogen; Ni-5256W In methanol at 120℃; under 15514.9 - 51716.2 Torr; for 3h; Product distribution / selectivity;A 5%
B n/a
C n/a
With ammonia; hydrogen; Ni-5256W In methanol at 120 - 130℃; under 15514.9 - 51716.2 Torr; for 3 - 5h; Product distribution / selectivity;
Stage #1: 1,4-cyclohexanedicarboxaldehyde; cis/trans-1,3-cyclohexanedicarboxaldehyde With ammonia; Ni catalyst supported on silica/alumina In methanol at 20 - 100℃; for 0.666667 - 0.75h;
Stage #2: With hydrogen; Ni catalyst supported on silica/alumina In methanol at 100℃; under 41372.9 Torr; Product distribution / selectivity;
623-26-7

terephthalonitrile

2549-93-1

1,4-bis-(aminomethyl)cyclohexane

Conditions
ConditionsYield
With ammonia; Hexadecane In 1,4-dioxane
In diethylamine
Hydrogenation;
33424-83-8

1,4-cyclohexanedicarboxaldehyde

55309-54-1

cis/trans-1,3-cyclohexanedicarboxaldehyde

A

2549-93-1

1,4-bis-(aminomethyl)cyclohexane

B

2579-20-6

cis, trans-1,3-dimethylaminocyclohexane

Conditions
ConditionsYield
With ammonia; hydrogen; Ni-5256W In methanol at 130℃; under 15514.9 - 51716.2 Torr; for 5h; Product distribution / selectivity;
With ammonia; hydrogen; Ni-5256P In methanol at 120℃; under 65783 - 68368.8 Torr; for 6.21667h; Product distribution / selectivity;
With ammonia; hydrogen; Raney nickel Ni-5256 In methanol at 130℃; under 15514.9 - 51716.2 Torr; for 15 - 19.5h; Product distribution / selectivity;
100-49-2

cyclohexylmethyl alcohol

A

1074-62-0

4-(aminomethyl)-cyclohexanemethanol

B

2549-93-1

1,4-bis-(aminomethyl)cyclohexane

C

283-24-9

3-azabicyclo[3,2,2]nonane

Conditions
ConditionsYield
With ammonia; hydrogen; Cu#Ni#Cr at 180 - 210℃; under 130050 Torr; Product distribution / selectivity;
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

A

1074-62-0

4-(aminomethyl)-cyclohexanemethanol

B

2549-93-1

1,4-bis-(aminomethyl)cyclohexane

Conditions
ConditionsYield
With ammonia; chlorocarbonylhydrido[4,5-bis(dicyclohexylphosphinomethyl)acridine]ruthenium(II) In tetrahydrofuran at 155℃; under 34128.4 Torr; for 12h; Autoclave; Inert atmosphere;
37830-06-1

N,N'-cyclohexane-1,4-diyldimethyl-bis-phthalimide

2549-93-1

1,4-bis-(aminomethyl)cyclohexane

Conditions
ConditionsYield
With hydrazine hydrate In ethanol for 4h; Reflux;
619-81-8, 619-82-9, 1076-97-7

cyclohexane-1,4-dicarboxylic acid

2549-93-1

1,4-bis-(aminomethyl)cyclohexane

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: ammonia; ammonium bicarbonate / water / 190 - 230 °C
2: 245 - 300 °C / 760.05 Torr
3: hydrogen / ethanol / 0.5 h / 95 °C / 37503.8 Torr
View Scheme
Multi-step reaction with 3 steps
1: ammonia / 0.5 h / 180 °C
2: phosphorus pentoxide / 1 h / 300 °C
3: hydrogen / ethanol / 0.5 h / 95 °C / 37503.8 Torr
View Scheme
Multi-step reaction with 3 steps
1: ammonia / 0.5 h / Heating
2: phosphorus pentoxide / 1 h / 300 °C / 15 - 37.5 Torr / Autoclave
3: hydrogen / ethanol / 0.5 h / 95 °C / 37503.8 Torr
View Scheme
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

2549-93-1

1,4-bis-(aminomethyl)cyclohexane

Conditions
ConditionsYield
With chlorocarbonylhydrido[4,5-bis(dicyclohexylphosphinomethyl)acridine]ruthenium(II); ammonia In tetrahydrofuran at 155℃; under 34128.4 Torr; for 12h;
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

A

1074-62-0

4-(aminomethyl)-cyclohexanemethanol

B

2549-93-1

1,4-bis-(aminomethyl)cyclohexane

C

283-24-9

3-azabicyclo[3,2,2]nonane

Conditions
ConditionsYield
With ammonia; hydrogen In water at 190℃; under 150015 Torr; Overall yield = 87.4 %;
With ammonia; hydrogen In water at 190℃; under 150015 Torr; Temperature; Concentration; Overall yield = 67.0 %;

1,4-Cyclohexanebis(methylamine) Chemical Properties

IUPAC  Name: [4-(Aminomethyl)cyclohexyl]methanamine    
Molecular Formula: C8H18N2
Molecular Weight: 142.28
Freely Rotating Bonds: 4
Polar Surface Area: 6.48 Å2
Index of Refraction: 1.477
Molar Refractivity: 44.12 cm3
Molar Volume: 155.9 cm3
Polarizability: 17.49 ×10-24 cm3
Surface Tension: 37.9 dyne/cm
Density: 0.912 g/cm3
Flash Point: 119.7 °C
Enthalpy of Vaporization: 46.6 kJ/mol
Boiling Point: 229.4 °C at 760 mmHg
Vapour Pressure: 0.0698 mmHg at 25°C 
The Cas Register Number of  1,4-Bis(aminomethyl)cyclohexane is 2549-93-1.The chemical synonyms of  1,4-Bis(aminomethyl)cyclohexane (CAS NO.2549-93-1) are 1,4-Cyclohexanedimethanamine, cis- ; Bamch  and  Hexahydro-p-xylylenediamine. The molecular structure of  1,4-Bis(aminomethyl)cyclohexane (CAS NO.2549-93-1) is  .

1,4-Cyclohexanebis(methylamine) Uses

 1,4-Bis(aminomethyl)cyclohexane (CAS NO.2549-93-1) is used in organic synthesis .

1,4-Cyclohexanebis(methylamine) Toxicity Data With Reference

1.    

skn-rbt 500 mg SEV

     SUNCO*    Sun Company Material Safety Data Sheets. (1608 Walnut St., Philadelphia, PA 19103) 10/78 .
2.    

orl-rat LD50:530 mg/kg

     SUNCO*    Sun Company Material Safety Data Sheets. (1608 Walnut St., Philadelphia, PA 19103) 10/78 .
3.    

skn-rbt LD50:420 mg/kg

     SUNCO*    Sun Company Material Safety Data Sheets. (1608 Walnut St., Philadelphia, PA 19103) 10/78 .

1,4-Cyclohexanebis(methylamine) Consensus Reports

Reported in EPA TSCA Inventory.

1,4-Cyclohexanebis(methylamine) Safety Profile

Moderately toxic by ingestion and skin contact. A severe skin irritant. When heated to decomposition it emits toxic fumes of NOx.
Hazard Codes: CorrosiveC
Risk Statements: 34-21/22 
R34: Causes burns. 
R21/22: Harmful in contact with skin and if swallowed.
Safety Statements: 45-36/37/39-25 
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection. 
S25: Avoid contact with eyes.
RIDADR: 2811
RTECS: GU7000010
HazardClass: 8
PackingGroup: II

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