2549-93-1

Basic information

• Product Name: 1,4-Cyclohexanebis(methylamine)
• Synonyms: RARECHEM AL BW 2178;1,4-bis(aminomethyl)-cyclohexan;1,4-cyclohexanedimethanamine;bamch;HEXAHYDRO-P-XYLENEDIAMINE;HEXAHYDRO-P-XYLYLENEDIAMINE;1,4-BIS(AMINOMETHYL)CYCLOHEXANE;1,4-BIS(AMINOETHYL)CYCLOHEXANE
• CAS NO: 2549-93-1
• Molecular Formula: C₈H₁₈N₂
• Molecular Weight: 142.24
• EINECS: 219-840-6
• Mol File: 2549-93-1.mol
• Article Data: 15

Chemical Properties

• Melting Point: -9 °C
• Boiling Point: 240-245 °C
• Flash Point: 107 °C
• Appearance: /
• Density: 0.94
• Vapor Pressure: 0.0698mmHg at 25°C
• Refractive Index: 1.491-1.495
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 10.57±0.29(Predicted)
• Water Solubility: Soluble
• Sensitive: Air Sensitive
• BRN: 2071383
• CAS DataBase Reference: 1,4-Cyclohexanebis(methylamine)(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-Cyclohexanebis(methylamine)(2549-93-1)
• EPA Substance Registry System: 1,4-Cyclohexanebis(methylamine)(2549-93-1)

Safety Data

• Hazard Codes: C
• Statements: 34-21/22
• Safety Statements: 45-36/37/39-25
• RIDADR: 2811
• RTECS: GU7000010
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 2549-93-1(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to slightly yellow liquid

Safety Profile

Moderately toxic by ingestion andskin contact. A severe skin irritant. When heated todecomposition it emits toxic fumes of NOx.

InChI:InChI=1/C8H18N2/c9-5-7-1-2-8(6-10)4-3-7/h7-8H,1-6,9-10H2/p+2

Synthetic route

cyclohexane-1,4-dicarbonitrile (10534-13-1) → 1,4-bis-(aminomethyl)cyclohexane (2549-93-1)

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;

1,4-cyclohexanedicarboxaldehyde (33424-83-8) + cis/trans-1,3-cyclohexanedicarboxaldehyde (55309-54-1) → 3-azabicyclo<3.3.1>nonane (280-70-6) + 1,4-bis-(aminomethyl)cyclohexane (2549-93-1) + cis, trans-1,3-dimethylaminocyclohexane (2579-20-6)

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;

terephthalonitrile (623-26-7) → 1,4-bis-(aminomethyl)cyclohexane (2549-93-1)

Conditions	Yield
With ammonia; Hexadecane In 1,4-dioxane
In diethylamine
Hydrogenation;

1,4-cyclohexanedicarboxaldehyde (33424-83-8) + cis/trans-1,3-cyclohexanedicarboxaldehyde (55309-54-1) → 1,4-bis-(aminomethyl)cyclohexane (2549-93-1) + cis, trans-1,3-dimethylaminocyclohexane (2579-20-6)

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;

cyclohexylmethyl alcohol (100-49-2) → 4-(aminomethyl)-cyclohexanemethanol (1074-62-0) + 1,4-bis-(aminomethyl)cyclohexane (2549-93-1) + 3-azabicyclo[3,2,2]nonane (283-24-9)

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

bis-1,4-(hydroxymethyl)cyclohexane (105-08-8) → 4-(aminomethyl)-cyclohexanemethanol (1074-62-0) + 1,4-bis-(aminomethyl)cyclohexane (2549-93-1)

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;

N,N'-cyclohexane-1,4-diyldimethyl-bis-phthalimide (37830-06-1) → 1,4-bis-(aminomethyl)cyclohexane (2549-93-1)

Conditions	Yield
With hydrazine hydrate In ethanol for 4h; Reflux;

cyclohexane-1,4-dicarboxylic acid (619-81-8, 619-82-9, 1076-97-7) → 1,4-bis-(aminomethyl)cyclohexane (2549-93-1)

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

bis-1,4-(hydroxymethyl)cyclohexane (105-08-8) → 1,4-bis-(aminomethyl)cyclohexane (2549-93-1)

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

bis-1,4-(hydroxymethyl)cyclohexane (105-08-8) → 4-(aminomethyl)-cyclohexanemethanol (1074-62-0) + 1,4-bis-(aminomethyl)cyclohexane (2549-93-1) + 3-azabicyclo[3,2,2]nonane (283-24-9)

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 %;

transcyclohexane-1,4-dicarboxylic acid amide (20101-86-4) → 1,4-bis-(aminomethyl)cyclohexane (2549-93-1)

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

tert-butyldicarbonate (34619-03-9) + 1,4-bis-(aminomethyl)cyclohexane (2549-93-1) → [4-(tert-butoxycarbonylamino-methyl)-cyclohexylmethyl]-carbamic acid tert-butyl ester (736054-16-3)

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

1,4-bis-(aminomethyl)cyclohexane (2549-93-1) + benzaldehyde (100-52-7) → 1,4-bis(benzylideneaminomethyl)cyclohexane (15332-44-2)

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

1,4-bis-(aminomethyl)cyclohexane (2549-93-1) + 4-nitrobenzaldehdye (555-16-8) → C22H24N4O4

Conditions	Yield
In ethanol at 60℃;	98%

cyclohexane-1,4-dicarbonitrile (10534-13-1)

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;

1,4-bis-(aminomethyl)cyclohexane (2549-93-1) + 3-Fluorobenzaldehyde

Conditions	Yield
In ethanol at 60℃;	96%

+ 1,4-bis-(aminomethyl)cyclohexane (2549-93-1) → N4-{[4-(aminomethyl)cyclohexyl]methyl}-N2-(2-bromobenzyl)-5-nitropyrimidine-2,4-diamine

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

1,4-bis-(aminomethyl)cyclohexane (2549-93-1) + 4-(2'-benzothienyl)-2-chloropyrimidine (124959-26-8) → [4(cis)-Aminomethylcyclohexylmethyl]-(4-benzo[b]thiophen-2-ylpyrimidin-2-yl)-amine

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

3-chloropyridazine (1120-95-2) + 1,4-bis-(aminomethyl)cyclohexane (2549-93-1) → N,N'-((1r,4r)-cyclohexane-1,4-diylbis(methylene))bis(pyridazin-3-amine) (1454914-58-9)

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

6-chloro-8-(2-chlorophenyl)-9-(4-chlorophenyl)-9H-purine (686344-50-3) + 1,4-bis-(aminomethyl)cyclohexane (2549-93-1) → N-{[4-(aminomethyl)cyclohexyl]methyl}-8-(2-chlorophenyl)-9-(4-chlorophenyl)-9H-purin-6-amine (1450979-82-4)

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

N1,N2-bis(tert-butoxycarbonyl)-N1-(methylcyclopropyl)-S-methylisothiourea (1029434-14-7) + 1,4-bis-(aminomethyl)cyclohexane (2549-93-1) → N-(cyclopropylmethyl)-N,N'-bis-(tert-butoxycarbonyl)-N''-[4-(aminomethyl)-cyclohexylmethyl]guanidine (1029434-19-2)

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

1,4-benzenedicarboxylic acid dimethyl ester (120-61-6) + 1,4-bis-(aminomethyl)cyclohexane (2549-93-1) → C26H30N2O6

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

+ salicylaldehyde → C22H26N2O2 (3353-15-9)

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

1,4-bis-(aminomethyl)cyclohexane (2549-93-1) + 6-chloro-(1,2,4,5-tetrazine) → N,N'-((1r,4r)-cyclohexane-1,4-diylbis(methylene))bis(1,2,4,5-tetrazin-3-amine) (1454914-64-7)

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

1,4-bis-(aminomethyl)cyclohexane (2549-93-1) + 4-dimethylamino-benzaldehyde (100-10-7) → C26H36N4 (3245-07-6)

Conditions	Yield
In ethanol at 60℃;	66%

Simazine (122-34-9) + 1,4-bis-(aminomethyl)cyclohexane (2549-93-1) → C15H29N7

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

(E)-3-(6,7,8-trimethoxy-2-naphthyl)-2-propenoic acid (203722-23-0) + 1,4-bis-(aminomethyl)cyclohexane (2549-93-1) → 1,4-bis[3-(6,7,8-trimethoxy-2-naphthyl)prop-(2E)-enoylaminomethyl]cyclohexane

Conditions	Yield
	60%

4-chloropyrimidine (17180-93-7) + 1,4-bis-(aminomethyl)cyclohexane (2549-93-1)

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

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

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

1,4-bis-(aminomethyl)cyclohexane + 5-chloro-(1,2,4-triazine) (1216085-30-1) → N,N'-((1r,4r)-cyclohexane-1,4-diylbis(methylene))bis(1,2,4-triazin-5-amine) (1454914-62-5)

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

1,4-bis-(aminomethyl)cyclohexane (2549-93-1) + Ethyl oxalyl chloride (4755-77-5) → 2,2'-((cyclohexane-1,4-diylbis(methylene))bis(azanediyl))bis(2-oxoacetic acid)

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%

2 chloro-3-methylpyridine (18368-76-8) + 1,4-bis-(aminomethyl)cyclohexane (2549-93-1) → N,N'-((1r,4r)-cyclohexane-1,4-diylbis(methylene))bis(3-methylpyridin-2-amine) (1454914-65-8)

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

2-chloropyrazin (14508-49-7) + 1,4-bis-(aminomethyl)cyclohexane (2549-93-1) → N,N'-((1r,4r)-cyclohexane-1,4-diylbis(methylene))bis(pyrazine-2-amine) (1454914-57-8)

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

1,4-bis-(aminomethyl)cyclohexane (2549-93-1) + N,N'-bis( tert-butoxycarbonyl)-1H-pyrazole-1-carboxamidine (152120-54-2, 862686-58-6, 1143572-00-2) → 1-(N,N'-diBoc)-guanidinomethyl-4-aminomethylcyclohexane (242452-33-1)

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

1,4-bis-(aminomethyl)cyclohexane (2549-93-1) + 1-[(tert-butyloxycarbonylamino)-(tert-butyloxycarbonylimino)-methyl]-1H-pyrazole → 1-(N,N'-di-boc)-guanidinomethyl-4-aminomethylcyclohexane (242452-33-1)

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

1,4-bis-(aminomethyl)cyclohexane (2549-93-1) + N,N'-bis( tert-butoxycarbonyl)-1H-pyrazole-1-carboxamidine (152120-54-2, 862686-58-6, 1143572-00-2) + 1-(N,N'-diBoc)-guanidinomethyl-4-aminomethylcyclohexane

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

+ 1,4-bis-(aminomethyl)cyclohexane + 2-Fluorobenzaldehyde (446-52-6) → 3,3'-(cyclohexane-1,4-diylbis(methylene))bis(2-(2-fluorophenyl)-2,3-dihydroquinazolin-4(1H)-one)

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

2,5-dimethyl-3-chloropyrazine (95-89-6) + 1,4-bis-(aminomethyl)cyclohexane (2549-93-1) → N,N'-((1r,4r)-cyclohexane-1,4-diylbis(methylene))bis(3,6-dimethylpyrazin-2-amine) (1454914-66-9)

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

2-fluoropyridine (372-48-5) + 1,4-bis-(aminomethyl)cyclohexane (2549-93-1) → N,N'-((1r,4r)-cyclohexane-1,4-diylbis(methylene))bis(pyridin-2-amine) (1454914-56-7)

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

1,4-bis-(aminomethyl)cyclohexane (2549-93-1) + (E,E)-5-(3,4,5-trimethoxyphenyl)-2,4-pentadienoic acid (28010-23-3) → N,N'-bis[5-(3,4,5-trimethoxyphenyl)penta-(2E,4E)-dienoyl]-1,4-bis(aminomethyl)cyclohexane

Conditions	Yield
	18%

Upstream product

• 20101-86-4 transcyclohexane-1,4-dicarboxylic acid amide 
• 105-08-8 bis-1,4-(hydroxymethyl)cyclohexane 
• 623-26-7 terephthalonitrile 
• 10534-13-1 cyclohexane-1,4-dicarbonitrile 
• 619-81-8 cyclohexane-1,4-dicarboxylic acid 
• 100-49-2 cyclohexylmethyl alcohol 
• 33424-83-8 1,4-cyclohexanedicarboxaldehyde 
• 55309-54-1 cis/trans-1,3-cyclohexanedicarboxaldehyde 
• 37830-06-1 N,N'-cyclohexane-1,4-diyldimethyl-bis-phthalimide 

Downstream Products

• 736054-16-3 [4-(tert-butoxycarbonylamino-methyl)-cyclohexylmethyl]-carbamic acid tert-butyl ester 
• 1142-36-5 N_.N'-Diacetyl-cyclohexan-cis-trans-1.4-bis-methylamin 
• 58980-88-4 N,N'-(1,4-Cyclohexylen-bis-methyl)-bis--dicarbanilat 
• 3353-15-9 C₂₂H₂₆N₂O₂ 
• 55778-72-8 N,N'-(1,4-cyclohexylenebismethyl)-bis[2-hydroxyoctylamine] 
• 15332-44-2 1,4-bis(benzylideneaminomethyl)cyclohexane 
• 55778-77-3 N,N'-(1,4-cyclohexylenebismethyl)-bis[2-hydroxydodecylamine] 
• 55778-73-9 N,N'-(1,4-cyclohexylenebismethyl)-bis[2-hydroxydecylamine] 
• 55778-76-2 N,N'-(1,4-cyclohexylenebismethyl)bis[N-methyl-2-hydroxydecylamine] 
• 15332-46-4 1,4-Cyclohexan-N,N,N',N'-tetrakis-(2-hydroxyethyl)-bis-(methylamin) 
• 10029-09-1 cis-cyclohexane-1,4-diyldimethanamine 
• 10029-07-9 trans-1,4-cyclohexane-bis(methylamine) 

Relevant articles and documents

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