• Name

  1,3-Cyclohexanebis(methylamine)

• EINECS 219-941-5
• CAS No. 2579-20-6
• Article Data19
• CAS DataBase
• Density 0.912 g/cm³
• Solubility soluble in water
• Melting Point -70 °C
• Formula C₈H₁₈N₂
• Boiling Point 219.95 °C at 760 mmHg
• Molecular Weight 142.244
• Flash Point 106.111 °C
• Transport Information UN 2735 8/PG 2
• Appearance Clear colorless liquid
• Safety 26-27-28-36/37/39-45-25
• Risk Codes 20/21/22-34-22
• Molecular Structure
• Hazard Symbols C
• Synonyms 1,3-Cyclohexanebis(methylamine)(7CI,8CI);1,3-BAC;1,3-Bis(aminomethyl)cyclohexane;1,3-Bis(methylamine)cyclohexane;1,3-Di(aminomethyl)cyclohexane;[[3-(Aminomethyl)cyclohexyl]methyl]amine;m-Bis(aminomethyl)cyclohexane;
• PSA 52.04000
• LogP 2.11080

Synthetic route

1477-55-0

1,3-di(aminomethyl)benzene

2579-20-6

cis, trans-1,3-dimethylaminocyclohexane

Conditions

Conditions	Yield
With 5% active carbon-supported ruthenium; lithium nitrate; hydrogen In isopropyl alcohol at 120℃; under 40504.1 Torr; for 0.333333h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;	90.6%
With hydrogen; sodium hydroxide In 1,4-dioxane at 70℃; under 37503.8 - 45004.5 Torr; for 0.01h; Temperature;	90%
With hydrogen; ruthenium(IV) oxide In ethanol

C9H14N2O2

2579-20-6

cis, trans-1,3-dimethylaminocyclohexane

Conditions

Conditions	Yield
With hydrazine hydrate; sodium hydroxide In 1,4-dioxane at 120℃; for 18h; pH=10;	88%

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

1,3-bis(salicylidiniminomethyl)cyclohexane

A

2579-20-6

cis, trans-1,3-dimethylaminocyclohexane

B

90-02-8

salicylaldehyde

Conditions

Conditions	Yield
With water at 30℃; Rate constant; var. pH;

626-17-5

benzene-1,3-dicarbonitrile

A

m-xylylenediamine

B

2579-20-6

cis, trans-1,3-dimethylaminocyclohexane

Conditions

Conditions	Yield
With hydrogen; 2% ruthenium/alumina In 1,4-dioxane; ammonia at 120℃; under 112511 Torr;

m-xylylenediamine

2579-20-6

cis, trans-1,3-dimethylaminocyclohexane

Conditions

Conditions	Yield
With hydrogen; 5 wt% Ru/C In ammonia at 120℃; under 75007.5 Torr;

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

626-17-5

benzene-1,3-dicarbonitrile

2579-20-6

cis, trans-1,3-dimethylaminocyclohexane

Conditions

Conditions	Yield
Hydrogenation;

286-20-4

cyclohexane-1,2-epoxide

2579-20-6

cis, trans-1,3-dimethylaminocyclohexane

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrogen / 220 °C / 760.05 Torr 2: tetraethylammonium hydroxide / 1,4-dioxane / 8.75 h / 90 °C 3: hydrogen; nickel(II) chloride hexahydrate / 8 h / 70 °C / 30003 Torr View Scheme

100377-18-2

1,3-dicyano-1-cyclohexanol

2579-20-6

cis, trans-1,3-dimethylaminocyclohexane

Conditions

Conditions	Yield
With nickel(II) chloride hexahydrate; hydrogen at 70℃; under 30003 Torr; for 8h; Reagent/catalyst; Temperature; Pressure;

5973-71-7

3,4-dimethylbenzaldehyde

2579-20-6

cis, trans-1,3-dimethylaminocyclohexane

1217526-73-2

C26H34N2

Conditions

Conditions	Yield
In methanol at 20℃; Molecular sieve;	100%
In methanol at 20℃; Molecular sieve;

3132-99-8

m-bromobenzoic aldehyde

2579-20-6

cis, trans-1,3-dimethylaminocyclohexane

1217527-02-0

C22H24Br2N2

Conditions

Conditions	Yield
In methanol at 20℃; Molecular sieve;	100%
In methanol at 20℃; Molecular sieve;

939-97-9

4-tert-Butylbenzaldehyde

2579-20-6

cis, trans-1,3-dimethylaminocyclohexane

1217526-91-4

C30H42N2

Conditions

Conditions	Yield
In methanol at 20℃; Molecular sieve;	100%
In methanol at 20℃; Molecular sieve;

5779-94-2

2,5-dimethylbenzaldehyde

2579-20-6

cis, trans-1,3-dimethylaminocyclohexane

1217526-78-7

C26H34N2

Conditions

Conditions	Yield
In methanol at 20℃; Molecular sieve;	100%
In methanol at 20℃; Molecular sieve;

5779-95-3

3,5-dimethylbenzaldehyde

2579-20-6

cis, trans-1,3-dimethylaminocyclohexane

1217526-72-1

C26H34N2

Conditions

Conditions	Yield
In methanol at 20℃; Molecular sieve;	100%
In methanol at 20℃; Molecular sieve;

2579-20-6

cis, trans-1,3-dimethylaminocyclohexane

28785-06-0

4-n-propylbenzaldehyde

1217526-85-6

C28H38N2

Conditions

Conditions	Yield
In methanol at 20℃; Molecular sieve;	100%
In methanol at 20℃; Molecular sieve;

2579-20-6

cis, trans-1,3-dimethylaminocyclohexane

1200-14-2

4-(n-butyl)benzaldehyde

1217526-89-0

C30H42N2

Conditions

Conditions	Yield
In methanol at 20℃; Molecular sieve;	100%
In methanol at 20℃; Molecular sieve;

2579-20-6

cis, trans-1,3-dimethylaminocyclohexane

104-87-0

4-methyl-benzaldehyde

1217526-68-5

C24H30N2

Conditions

Conditions	Yield
In methanol at 20℃; Molecular sieve;	100%
In methanol at 20℃; Molecular sieve;

2579-20-6

cis, trans-1,3-dimethylaminocyclohexane

459-57-4

4-fluorobenzaldehyde

1217527-04-2

C22H24F2N2

Conditions

Conditions	Yield
In methanol at 20℃; Molecular sieve;	100%
In methanol at 20℃; Molecular sieve;

2579-20-6

cis, trans-1,3-dimethylaminocyclohexane

104-88-1

4-chlorobenzaldehyde

1217526-94-7

C22H24Cl2N2

Conditions

Conditions	Yield
In methanol at 20℃; Molecular sieve;	100%
In methanol at 20℃; Molecular sieve;

2579-20-6

cis, trans-1,3-dimethylaminocyclohexane

83-38-5

2,6-dichlorobenzaldehyde

1217526-98-1

C22H22Cl4N2

Conditions

Conditions	Yield
In methanol at 20℃; Molecular sieve;	100%
In methanol at 20℃; Molecular sieve;

2579-20-6

cis, trans-1,3-dimethylaminocyclohexane

99-61-6

3-nitro-benzaldehyde

1217527-06-4

C22H24N4O4

Conditions

Conditions	Yield
In methanol at 20℃; Molecular sieve;	100%
In methanol at 20℃; Molecular sieve;

2579-20-6

cis, trans-1,3-dimethylaminocyclohexane

100-52-7

benzaldehyde

2539-69-7

C22H26N2

Conditions

Conditions	Yield
In methanol at 20℃; Molecular sieve;	100%
In methanol at 20℃; Molecular sieve;

2579-20-6

cis, trans-1,3-dimethylaminocyclohexane

587-04-2

3-Chlorobenzaldehyde

1217526-97-0

C22H24Cl2N2

Conditions

Conditions	Yield
In methanol at 20℃; Molecular sieve;	100%
In methanol at 20℃; Molecular sieve;

2579-20-6

cis, trans-1,3-dimethylaminocyclohexane

1122-91-4

4-bromo-benzaldehyde

1217527-00-8

C22H24Br2N2

Conditions

Conditions	Yield
In methanol at 20℃; Molecular sieve;	100%

2579-20-6

cis, trans-1,3-dimethylaminocyclohexane

15764-16-6

2,4-dimethylbenzaldehyde

1217526-81-2

C26H34N2

Conditions

Conditions	Yield
In methanol at 20℃; Molecular sieve;	100%
In methanol at 20℃; Molecular sieve;

2579-20-6

cis, trans-1,3-dimethylaminocyclohexane

529-20-4

2-methylphenyl aldehyde

1217526-75-4

C24H30N2

Conditions

Conditions	Yield
In methanol at 20℃; Molecular sieve;	100%
In methanol at 20℃; Molecular sieve;

2579-20-6

cis, trans-1,3-dimethylaminocyclohexane

4748-78-1

4-ethylbenzylaldehyde

1217526-83-4

C26H34N2

Conditions

Conditions	Yield
In methanol at 20℃; Molecular sieve;	100%
In methanol at 20℃; Molecular sieve;

2579-20-6

cis, trans-1,3-dimethylaminocyclohexane

122-03-2

(4-isopropylbenzaldehyde)

1217526-87-8

C28H38N2

Conditions

Conditions	Yield
In methanol at 20℃; Molecular sieve;	100%
In methanol at 20℃; Molecular sieve;

2579-20-6

cis, trans-1,3-dimethylaminocyclohexane

620-23-5

m-tolyl aldehyde

1217526-70-9

C24H30N2

Conditions

Conditions	Yield
In methanol at 20℃; Molecular sieve;	100%
In methanol at 20℃; Molecular sieve;

2579-20-6

cis, trans-1,3-dimethylaminocyclohexane

456-48-4

3-Fluorobenzaldehyde

1217527-05-3

C22H24F2N2

Conditions

Conditions	Yield
In methanol at 20℃; Molecular sieve;	100%
In methanol at 20℃; Molecular sieve;

2579-20-6

cis, trans-1,3-dimethylaminocyclohexane

616-38-6

carbonic acid dimethyl ester

1,3-bis(methoxycarbonylaminomethyl)cyclohexane

Conditions

Conditions	Yield
lipase from Candida antarctica In toluene at 70℃; for 48h; Product distribution / selectivity;	99%
With sodium methylate In methanol; water at 50℃; for 7h;	97%
With water; sodium methylate In methanol; acetone at 50℃; for 5.5h; Solvent;	95.5%

2579-20-6

cis, trans-1,3-dimethylaminocyclohexane

106-89-8

epichlorohydrin

65992-66-7

N,N,N',N'tetraglycidyl-1,3-bis-(aminomethyl) cyclohexane

Conditions

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In water; toluene at 90℃; for 1h; Product distribution / selectivity; Inert atmosphere;	97.2%

75-44-5

phosgene

2579-20-6

cis, trans-1,3-dimethylaminocyclohexane

38661-72-2

1,3-bis(isocyanatomethyl)-cyclohexane

Conditions

Conditions	Yield
Stage #1: cis, trans-1,3-dimethylaminocyclohexane With hydrogenchloride In chlorobenzene at 30 - 45℃; for 3.5h; Large scale; Stage #2: phosgene In chlorobenzene at 60℃; Large scale;	96.5%
Stage #1: cis, trans-1,3-dimethylaminocyclohexane With carbon dioxide In toluene at 25 - 30℃; for 1.33333h; Stage #2: phosgene In toluene at 25 - 90℃; for 23h;
Stage #1: cis, trans-1,3-dimethylaminocyclohexane With hydrogenchloride In water; toluene at 20℃; for 0.5h; Stage #2: phosgene With N,N-dimethyl-formamide In 5,5-dimethyl-1,3-cyclohexadiene at 140℃; for 5h; Solvent;
In 1,2-dichloro-benzene at 0 - 130℃; for 11h; Solvent; Temperature;

2579-20-6

cis, trans-1,3-dimethylaminocyclohexane

105-58-8

Diethyl carbonate

1,3-bis(ethoxycarbonylaminomethyl)cyclohexane

Conditions

Conditions	Yield
With sodium methylate In methanol at 50℃; for 6h;	95.9%
With water; sodium methylate In methanol at 50℃; for 6.5h;	95.9%

2579-20-6

cis, trans-1,3-dimethylaminocyclohexane

708-06-5

2-hydroxynaphthalene-1-carbaldehyde

α,α'-bis(2-hydroxy-1-naphthaliminomethyl)-1,3-cyclohexane

Conditions

Conditions	Yield
In methanol for 4h; Reflux;	95%

2033-24-1

cycl-isopropylidene malonate

2579-20-6

cis, trans-1,3-dimethylaminocyclohexane

149-73-5

trimethyl orthoformate

C22H30N2O8

Conditions

Conditions	Yield
Stage #1: cycl-isopropylidene malonate; trimethyl orthoformate for 1h; Reflux; Stage #2: cis, trans-1,3-dimethylaminocyclohexane for 2h; Reflux;	92%

...Expand

2579-20-6

cis, trans-1,3-dimethylaminocyclohexane

90-02-8

salicylaldehyde

183246-63-1

α,α'-bis(salicyliminomethyl)-1,3-cyclohexane

Conditions

Conditions	Yield
In methanol for 4h; Reflux;	91%

85-44-9

phthalic anhydride

2579-20-6

cis, trans-1,3-dimethylaminocyclohexane

942291-68-1

N,N'-cyclohexane-1,3-diyldimethyl-bis-phthalimide

Conditions

Conditions	Yield
With acetic acid Heating;	90%

1,3-Cyclohexanebis(methylamine) Chemical Properties

1,3-Cyclohexanebis(methylamine) Toxicity Data With Reference

1,3-Cyclohexanebis(methylamine) Consensus Reports

1,3-Cyclohexanebis(methylamine) Safety Profile