1,4-Cyclohexanebis(methylamine) supplier

Name
1,4-Cyclohexanebis(methylamine)
EINECS 219-840-6
CAS No. 2549-93-1
Article Data19
CAS DataBase
Density 0.94
Solubility SOLUBLE
Melting Point -9 °C
Formula C8H18 N2
Boiling Point 240-245 ºC
Molecular Weight 142.244
Flash Point 107 ºC
Transport Information
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 NO_x.
Risk Codes R21/22;R34
Molecular Structure
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
PSA 52.04000
LogP 2.11080

Synthetic route

: 10534-13-1
cyclohexane-1,4-dicarbonitrile

: 2549-93-1
1,4-bis-(aminomethyl)cyclohexane

Conditions

Conditions	Yield
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

Conditions	Yield
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;

...Expand

: 623-26-7
terephthalonitrile

: 2549-93-1
1,4-bis-(aminomethyl)cyclohexane

Conditions

Conditions	Yield
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

Conditions	Yield
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;

...Expand

: 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

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

...Expand

: 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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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 %;

...Expand

: 20101-86-4
transcyclohexane-1,4-dicarboxylic acid amide

: 2549-93-1
1,4-bis-(aminomethyl)cyclohexane

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 245 - 300 °C / 760.05 Torr 2: hydrogen / ethanol / 0.5 h / 95 °C / 37503.8 Torr View Scheme
Multi-step reaction with 2 steps 1: phosphorus pentoxide / 1 h / 300 °C 2: hydrogen / ethanol / 0.5 h / 95 °C / 37503.8 Torr View Scheme
Multi-step reaction with 2 steps 1: phosphorus pentoxide / 1 h / 300 °C / 15 - 37.5 Torr / Autoclave 2: hydrogen / ethanol / 0.5 h / 95 °C / 37503.8 Torr View Scheme

: 34619-03-9
tert-butyldicarbonate

: 2549-93-1
1,4-bis-(aminomethyl)cyclohexane

: 736054-16-3
[4-(tert-butoxycarbonylamino-methyl)-cyclohexylmethyl]-carbamic acid tert-butyl ester

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 16h;	99%

: 2549-93-1
1,4-bis-(aminomethyl)cyclohexane

: 100-52-7
benzaldehyde

: 15332-44-2
1,4-bis(benzylideneaminomethyl)cyclohexane

Conditions

Conditions	Yield
at 60℃; under 40 - 60 Torr; for 0.5h;	98%
In ethanol Ambient temperature;

: 2549-93-1
1,4-bis-(aminomethyl)cyclohexane

: 555-16-8
4-nitrobenzaldehdye

: C22H24N4O4

Conditions

Conditions	Yield
In ethanol at 60℃;	98%

: 10534-13-1
cyclohexane-1,4-dicarbonitrile

Conditions

Conditions	Yield
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;

: 2549-93-1
1,4-bis-(aminomethyl)cyclohexane

3-Fluorobenzaldehyde: 3-Fluorobenzaldehyde

Conditions

Conditions	Yield
In ethanol at 60℃;	96%

: 2549-93-1
1,4-bis-(aminomethyl)cyclohexane

: N4-{[4-(aminomethyl)cyclohexyl]methyl}-N2-(2-bromobenzyl)-5-nitropyrimidine-2,4-diamine

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 16h;	89%
In dichloromethane at 20℃; for 16h;	89%

: 2549-93-1
1,4-bis-(aminomethyl)cyclohexane

: 124959-26-8
4-(2'-benzothienyl)-2-chloropyrimidine

: [4(cis)-Aminomethylcyclohexylmethyl]-(4-benzo[b]thiophen-2-ylpyrimidin-2-yl)-amine

Conditions

Conditions	Yield
In isopropyl alcohol at 20 - 110℃; for 20h;	88%

: 1120-95-2
3-chloropyridazine

: 2549-93-1
1,4-bis-(aminomethyl)cyclohexane

: 1454914-58-9
N,N'-((1r,4r)-cyclohexane-1,4-diylbis(methylene))bis(pyridazin-3-amine)

Conditions

Conditions	Yield
With 5-chloro-1,3-benzenediamine In 1-methyl-pyrrolidin-2-one at 120℃;	85%

: 686344-50-3
6-chloro-8-(2-chlorophenyl)-9-(4-chlorophenyl)-9H-purine

: 2549-93-1
1,4-bis-(aminomethyl)cyclohexane

: 1450979-82-4
N-{[4-(aminomethyl)cyclohexyl]methyl}-8-(2-chlorophenyl)-9-(4-chlorophenyl)-9H-purin-6-amine

Conditions

Conditions	Yield
In 1,4-dioxane at 80℃; for 16h;	76%

: 1029434-14-7
N1,N2-bis(tert-butoxycarbonyl)-N1-(methylcyclopropyl)-S-methylisothiourea

: 2549-93-1
1,4-bis-(aminomethyl)cyclohexane

: 1029434-19-2
N-(cyclopropylmethyl)-N,N'-bis-(tert-butoxycarbonyl)-N''-[4-(aminomethyl)-cyclohexylmethyl]guanidine

Conditions

Conditions	Yield
In tetrahydrofuran at 50℃; for 3h;	75%

: 120-61-6
1,4-benzenedicarboxylic acid dimethyl ester

: 2549-93-1
1,4-bis-(aminomethyl)cyclohexane

C26H30N2O6: C26H30N2O6

Conditions

Conditions	Yield
With lithium methanolate In methanol; toluene at 120℃; for 10h;	75%

salicylaldehyde: salicylaldehyde

: 3353-15-9
C22H26N2O2

Conditions

Conditions	Yield
With acetic acid In ethanol for 4h; Reflux;	72.8%

: 2549-93-1
1,4-bis-(aminomethyl)cyclohexane

: 6-chloro-(1,2,4,5-tetrazine)

: 1454914-64-7
N,N'-((1r,4r)-cyclohexane-1,4-diylbis(methylene))bis(1,2,4,5-tetrazin-3-amine)

Conditions

Conditions	Yield
With 5-chloro-1,3-benzenediamine at 110℃; for 24h;	70%

: 2549-93-1
1,4-bis-(aminomethyl)cyclohexane

: 100-10-7
4-dimethylamino-benzaldehyde

: 3245-07-6
C26H36N4

Conditions

Conditions	Yield
In ethanol at 60℃;	66%

: 122-34-9
Simazine

: 2549-93-1
1,4-bis-(aminomethyl)cyclohexane

: C15H29N7

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In 1,4-dioxane for 72h; Heating / reflux;	65%

: 203722-23-0
(E)-3-(6,7,8-trimethoxy-2-naphthyl)-2-propenoic acid

: 2549-93-1
1,4-bis-(aminomethyl)cyclohexane

: 1,4-bis[3-(6,7,8-trimethoxy-2-naphthyl)prop-(2E)-enoylaminomethyl]cyclohexane

Conditions

Conditions	Yield
	60%

: 17180-93-7
4-chloropyrimidine

: 2549-93-1
1,4-bis-(aminomethyl)cyclohexane

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 130℃; for 8h;	60%

: 2549-93-1
1,4-bis-(aminomethyl)cyclohexane

Conditions

Conditions	Yield
In tetrahydrofuran at 50℃; for 3h;	58%

1,4-bis-(aminomethyl)cyclohexane: 1,4-bis-(aminomethyl)cyclohexane

: 1216085-30-1
5-chloro-(1,2,4-triazine)

: 1454914-62-5
N,N'-((1r,4r)-cyclohexane-1,4-diylbis(methylene))bis(1,2,4-triazin-5-amine)

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide for 4h; Reflux;	57%

: 2549-93-1
1,4-bis-(aminomethyl)cyclohexane

: 4755-77-5
Ethyl oxalyl chloride

: 2,2'-((cyclohexane-1,4-diylbis(methylene))bis(azanediyl))bis(2-oxoacetic acid)

Conditions

Conditions	Yield
Stage #1: 1,4-bis-(aminomethyl)cyclohexane; Ethyl oxalyl chloride Stage #2: With water; lithium hydroxide In tetrahydrofuran at 20℃; for 12h;	52%

: 18368-76-8
2 chloro-3-methylpyridine

: 2549-93-1
1,4-bis-(aminomethyl)cyclohexane

: 1454914-65-8
N,N'-((1r,4r)-cyclohexane-1,4-diylbis(methylene))bis(3-methylpyridin-2-amine)

Conditions

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In N,N-dimethyl acetamide at 90℃; for 18h;	45%

: 14508-49-7
2-chloropyrazin

: 2549-93-1
1,4-bis-(aminomethyl)cyclohexane

: 1454914-57-8
N,N'-((1r,4r)-cyclohexane-1,4-diylbis(methylene))bis(pyrazine-2-amine)

Conditions

Conditions	Yield
With sodium carbonate In N,N-dimethyl-formamide at 100℃; for 8h;	45%

: 2549-93-1
1,4-bis-(aminomethyl)cyclohexane

: 152120-54-2, 862686-58-6, 1143572-00-2
N,N'-bis( tert-butoxycarbonyl)-1H-pyrazole-1-carboxamidine

: 242452-33-1
1-(N,N'-diBoc)-guanidinomethyl-4-aminomethylcyclohexane

Conditions

Conditions	Yield
In tetrahydrofuran; dichloromethane; ethyl acetate	43%
In tetrahydrofuran at 20℃; for 0.5 - 3h;	42%

: 2549-93-1
1,4-bis-(aminomethyl)cyclohexane

: 1-[(tert-butyloxycarbonylamino)-(tert-butyloxycarbonylimino)-methyl]-1H-pyrazole

: 242452-33-1
1-(N,N'-di-boc)-guanidinomethyl-4-aminomethylcyclohexane

Conditions

Conditions	Yield
In tetrahydrofuran at 20℃; for 0.5 - 3h; Product distribution / selectivity;	42%

: 2549-93-1
1,4-bis-(aminomethyl)cyclohexane

: 152120-54-2, 862686-58-6, 1143572-00-2
N,N'-bis( tert-butoxycarbonyl)-1H-pyrazole-1-carboxamidine

A

B 1-(N,N'-diBoc)-guanidinomethyl-4-aminomethylcyclohexane: 1-(N,N'-diBoc)-guanidinomethyl-4-aminomethylcyclohexane

Conditions

Conditions	Yield
In tetrahydrofuran; ethyl acetate	A n/a B 42%

...Expand

1,4-bis-(aminomethyl)cyclohexane: 1,4-bis-(aminomethyl)cyclohexane

: 446-52-6
2-Fluorobenzaldehyde

: 3,3'-(cyclohexane-1,4-diylbis(methylene))bis(2-(2-fluorophenyl)-2,3-dihydroquinazolin-4(1H)-one)

Conditions

Conditions	Yield
With acetic acid for 4h; Reflux;	40%

...Expand

: 95-89-6
2,5-dimethyl-3-chloropyrazine

: 2549-93-1
1,4-bis-(aminomethyl)cyclohexane

: 1454914-66-9
N,N'-((1r,4r)-cyclohexane-1,4-diylbis(methylene))bis(3,6-dimethylpyrazin-2-amine)

Conditions

Conditions	Yield
With caesium carbonate; lithium fluoride In N,N-dimethyl-formamide at 135℃; for 16h;	35%

: 372-48-5
2-fluoropyridine

: 2549-93-1
1,4-bis-(aminomethyl)cyclohexane

: 1454914-56-7
N,N'-((1r,4r)-cyclohexane-1,4-diylbis(methylene))bis(pyridin-2-amine)

Conditions

Conditions	Yield
at 100 - 150℃; for 10h;	30%

: 2549-93-1
1,4-bis-(aminomethyl)cyclohexane

: 28010-23-3
(E,E)-5-(3,4,5-trimethoxyphenyl)-2,4-pentadienoic acid

: N,N'-bis[5-(3,4,5-trimethoxyphenyl)penta-(2E,4E)-dienoyl]-1,4-bis(aminomethyl)cyclohexane

Conditions

Conditions	Yield
	18%

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^-24cm³
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 NO_x.
Hazard Codes: Corrosive C
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

Product Name

1,4-Cyclohexanebis(methylamine)

Synthetic route

1,4-Cyclohexanebis(methylamine) Chemical Properties

1,4-Cyclohexanebis(methylamine) Uses

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

1,4-Cyclohexanebis(methylamine) Consensus Reports

1,4-Cyclohexanebis(methylamine) Safety Profile

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