2579-20-6

Basic information

• Product Name: 1,3-Cyclohexanebis(methylamine)
• Synonyms: 1,3-cyclohexanebis(methylamine), mixture of isomers;1,3-BIS(AMINOMETHYL)CYCLOHEXANE (CIS/TRANS MIXTURE);1,3-BIS(AMINOMETHY) CYCLOHEXANE;1,3-CYCLOHEXANEBIS(METHYLAMINE) 99% MIXTURE OF CIS AND TRANS;1,3-Bis(aminomethyl)cyclohexane (cis- and trans- mixture);1,3-Cyclohexanebismethanamine;1,3-Cyclohexanediylbis(methanamine);CBMA
• CAS NO: 2579-20-6
• Molecular Formula: C₈H₁₈N₂
• Molecular Weight: 142.24
• EINECS: 219-941-5
• Mol File: 2579-20-6.mol
• Article Data: 16

Chemical Properties

• Melting Point: -70 °C
• Boiling Point: 220 °C
• Flash Point: 223 °F
• Appearance: Clear colorless/Liquid
• Density: 0.945 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.116mmHg at 25°C
• Refractive Index: n20/D 1.493(lit.)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 10.57±0.29(Predicted)
• Water Solubility: Soluble
• CAS DataBase Reference: 1,3-Cyclohexanebis(methylamine)(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Cyclohexanebis(methylamine)(2579-20-6)
• EPA Substance Registry System: 1,3-Cyclohexanebis(methylamine)(2579-20-6)

Safety Data

• Hazard Codes: C
• Statements: 20/21/22-34-22-52/53-35-21/22
• Safety Statements: 26-27-28-36/37/39-45-25-61
• RIDADR: UN 2735 8/PG 2
• WGK Germany: 3
• RTECS: GU7000000
• HazardClass: 8
• PackingGroup: I
• Hazardous Substances Data: 2579-20-6(Hazardous Substances Data)

Usage

Chemical Properties

CLEAR COLORLESS LIQUID

Uses

Different sources of media describe the Uses of 2579-20-6 differently. You can refer to the following data:
1. 1,3-cyclohexanebis(methylamine) be used as organic intermediates and epoxy curing agents.
2. 1,3-Cyclohexanebis(methylamine), mixture of isomers (1,3-BAC), is used as a cross-linking agent that can be used in the formation of fiber-based membranes for the separation of CO2. It can also be used in the synthesis of open-framework bimetallic phosphites for potential usage in molecular sieves and ion exchangers.

General Description

This product has been enhanced for energy efficiency.

Safety Profile

Poison by skin contact andintraperitoneal routes. Moderately toxic by ingestion.When heated to decomposition it emits toxic fumes ofNOx.

InChI:InChI=1/C8H18N2/c9-5-7-2-1-3-8(4-7)6-10/h7-8H,1-6,9-10H2/p+2/t7-,8-/m0/s1

Synthetic route

1,3-di(aminomethyl)benzene (1477-55-0) → cis, trans-1,3-dimethylaminocyclohexane (2579-20-6)

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 → cis, trans-1,3-dimethylaminocyclohexane (2579-20-6)

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

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;

1,3-bis(salicylidiniminomethyl)cyclohexane → cis, trans-1,3-dimethylaminocyclohexane (2579-20-6) + salicylaldehyde (90-02-8)

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

benzene-1,3-dicarbonitrile (626-17-5) → m-xylylenediamine + cis, trans-1,3-dimethylaminocyclohexane (2579-20-6)

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

m-xylylenediamine → cis, trans-1,3-dimethylaminocyclohexane (2579-20-6)

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

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;

benzene-1,3-dicarbonitrile (626-17-5) → cis, trans-1,3-dimethylaminocyclohexane (2579-20-6)

Conditions	Yield
Hydrogenation;

cyclohexane-1,2-epoxide (286-20-4) → cis, trans-1,3-dimethylaminocyclohexane (2579-20-6)

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

1,3-dicyano-1-cyclohexanol (100377-18-2) → cis, trans-1,3-dimethylaminocyclohexane (2579-20-6)

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

3,4-dimethylbenzaldehyde (5973-71-7) + cis, trans-1,3-dimethylaminocyclohexane (2579-20-6) → C26H34N2 (1217526-73-2)

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

m-bromobenzoic aldehyde (3132-99-8) + cis, trans-1,3-dimethylaminocyclohexane (2579-20-6) → C22H24Br2N2 (1217527-02-0)

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

4-tert-Butylbenzaldehyde (939-97-9) + cis, trans-1,3-dimethylaminocyclohexane (2579-20-6) → C30H42N2 (1217526-91-4)

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

2,5-dimethylbenzaldehyde (5779-94-2) + cis, trans-1,3-dimethylaminocyclohexane (2579-20-6) → C26H34N2 (1217526-78-7)

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

3,5-dimethylbenzaldehyde (5779-95-3) + cis, trans-1,3-dimethylaminocyclohexane (2579-20-6) → C26H34N2 (1217526-72-1)

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

cis, trans-1,3-dimethylaminocyclohexane (2579-20-6) + 4-n-propylbenzaldehyde (28785-06-0) → C28H38N2 (1217526-85-6)

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

cis, trans-1,3-dimethylaminocyclohexane (2579-20-6) + 4-(n-butyl)benzaldehyde (1200-14-2) → C30H42N2 (1217526-89-0)

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

cis, trans-1,3-dimethylaminocyclohexane (2579-20-6) + 4-methyl-benzaldehyde (104-87-0) → C24H30N2 (1217526-68-5)

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

cis, trans-1,3-dimethylaminocyclohexane (2579-20-6) + 4-fluorobenzaldehyde (459-57-4) → C22H24F2N2 (1217527-04-2)

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

cis, trans-1,3-dimethylaminocyclohexane (2579-20-6) + 4-chlorobenzaldehyde (104-88-1) → C22H24Cl2N2 (1217526-94-7)

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

cis, trans-1,3-dimethylaminocyclohexane (2579-20-6) + 2,6-dichlorobenzaldehyde (83-38-5) → C22H22Cl4N2 (1217526-98-1)

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

cis, trans-1,3-dimethylaminocyclohexane (2579-20-6) + 3-nitro-benzaldehyde (99-61-6) → C22H24N4O4 (1217527-06-4)

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

cis, trans-1,3-dimethylaminocyclohexane (2579-20-6) + benzaldehyde (100-52-7) → C22H26N2 (2539-69-7)

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

cis, trans-1,3-dimethylaminocyclohexane (2579-20-6) + 3-Chlorobenzaldehyde (587-04-2) → C22H24Cl2N2 (1217526-97-0)

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

cis, trans-1,3-dimethylaminocyclohexane (2579-20-6) + 4-bromo-benzaldehyde (1122-91-4) → C22H24Br2N2 (1217527-00-8)

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

cis, trans-1,3-dimethylaminocyclohexane (2579-20-6) + 2,4-dimethylbenzaldehyde (15764-16-6) → C26H34N2 (1217526-81-2)

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

cis, trans-1,3-dimethylaminocyclohexane (2579-20-6) + 2-methylphenyl aldehyde (529-20-4) → C24H30N2 (1217526-75-4)

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

cis, trans-1,3-dimethylaminocyclohexane (2579-20-6) + 4-ethylbenzylaldehyde (4748-78-1) → C26H34N2 (1217526-83-4)

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

cis, trans-1,3-dimethylaminocyclohexane (2579-20-6) + (4-isopropylbenzaldehyde) (122-03-2) → C28H38N2 (1217526-87-8)

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

cis, trans-1,3-dimethylaminocyclohexane (2579-20-6) + m-tolyl aldehyde (620-23-5) → C24H30N2 (1217526-70-9)

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

cis, trans-1,3-dimethylaminocyclohexane (2579-20-6) + 3-Fluorobenzaldehyde (456-48-4) → C22H24F2N2 (1217527-05-3)

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

cis, trans-1,3-dimethylaminocyclohexane (2579-20-6) + carbonic acid dimethyl ester (616-38-6) → 1,3-bis(methoxycarbonylaminomethyl)cyclohexane

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%

cis, trans-1,3-dimethylaminocyclohexane (2579-20-6) + epichlorohydrin (106-89-8) → N,N,N',N'tetraglycidyl-1,3-bis-(aminomethyl) cyclohexane (65992-66-7)

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%

phosgene (75-44-5) + cis, trans-1,3-dimethylaminocyclohexane (2579-20-6) → 1,3-bis(isocyanatomethyl)-cyclohexane (38661-72-2)

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;

cis, trans-1,3-dimethylaminocyclohexane (2579-20-6) + Diethyl carbonate (105-58-8) → 1,3-bis(ethoxycarbonylaminomethyl)cyclohexane

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%

cis, trans-1,3-dimethylaminocyclohexane (2579-20-6) + 2-hydroxynaphthalene-1-carbaldehyde (708-06-5) → α,α'-bis(2-hydroxy-1-naphthaliminomethyl)-1,3-cyclohexane

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

cycl-isopropylidene malonate (2033-24-1) + cis, trans-1,3-dimethylaminocyclohexane (2579-20-6) + trimethyl orthoformate (149-73-5) → C22H30N2O8

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

cis, trans-1,3-dimethylaminocyclohexane (2579-20-6) + salicylaldehyde (90-02-8) → α,α'-bis(salicyliminomethyl)-1,3-cyclohexane (183246-63-1)

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

phthalic anhydride (85-44-9) + cis, trans-1,3-dimethylaminocyclohexane (2579-20-6) → N,N'-cyclohexane-1,3-diyldimethyl-bis-phthalimide (942291-68-1)

Conditions	Yield
With acetic acid Heating;	90%

Upstream product

• 626-17-5 benzene-1,3-dicarbonitrile 
• 100377-18-2 1,3-dicyano-1-cyclohexanol 
• 286-20-4 cyclohexane-1,2-epoxide 
• 33424-83-8 1,4-cyclohexanedicarboxaldehyde 
• 55309-54-1 cis/trans-1,3-cyclohexanedicarboxaldehyde 
• 1477-55-0 1,3-di(aminomethyl)benzene 

Downstream Products

• 743460-78-8 5-[(R)-2-[(3-Aminomethylcyclohexylmethyl)amino]-1-(tert-butyldimethylsilanyloxy)ethyl]-8-benzyloxy-1H-quinolin-2-one 
• 242452-34-2 1-(N,N'-diBoc)-guanidinomethyl-3-aminomethylcyclohexane 
• 942291-68-1 N,N'-cyclohexane-1,3-diyldimethyl-bis-phthalimide 
• 4425-82-5 9-methylene-fluorene 
• 106-47-8 4-chloro-aniline 
• 108559-85-9 1-N-(4'-hydroxy)butanoylaminomethyl-3-aminomethylcyclohexane 
• 38661-72-2 1,3-bis(isocyanatomethyl)-cyclohexane 

Relevant articles and documents

Preparation process of 1, 3-cyclohexanediamine

The invention discloses a preparation process of 1, 3-cyclohexane dimethylamine, and the process comprises the following steps: 1) isomerization dehydrogenation of cyclohexene oxide: converting cyclohexene oxide into cyclohexenone under the action of an isomerization dehydrogenation catalyst; 2) addition of cyclohexenone and hydrocyanic acid: reacting cyclohexenone under the action of hydrocyanicacid and an alkaline addition catalyst to generate 1, 3-dicyano-1-cyclohexanol; 3) dehydration and hydrogenation of 1, 3-dicyano-1-cyclohexanol: carrying out dehydration and hydrogenation on the obtained 1, 3-dicyano-1-cyclohexanol in the presence of hydrogen and a hydrogenation catalyst to generate 1, 3-cyclohexanediamine. Compared with the prior art, the invention has the beneficial effects thatthe raw materials are cheap and easy to obtain; the reaction yield is high, and the total yield is greater than or equal to 90%; the reaction conditions are mild and suitable for industrialization.

Ru/g-C3N4as an efficient catalyst for selective hydrogenation of aromatic diamines to alicyclic diamines

A series of Ru/g-C3N4materials with highly dispersed Ru were firstly prepared by an ultrasonic impregnation method using carbon nitride as a support. The catalysts were characterized by various techniques including BET and elemental analysis, ICP-AES, XPS, XRD, CO2-TPD and TEM. The results demonstrated that Ru/g-C3N4materials with a mesoporous structure and highly dispersed Ru were successfully prepared. The chemo-selective hydrogenation ofp-phenylenediamine (PPDA) to 1,4-cyclohexanediamine (CHDA) over Ru/g-C3N4as a model reaction was investigated in detail. PPDA conversion of 100% with a CHDA selectivity of more than 86% could be achieved under mild conditions. It can be inferred that the carbon nitride support possessed abundant basic sites and the Ru/g-C3N4-Tcatalysts provided suitable basicity for the aromatic ring hydrogenation. Compared to the N-free Ru/C catalyst, the involvement of nitrogen species in Ru/g-C3N4remarkably improved the catalytic performance. In addition, the recyclability of the catalyst demonstrated that the aggregation of Ru nanoparticles was responsible for the decrease of the catalytic activity. Furthermore, this strategy also could be expanded to the selective hydrogenation of other aromatic diamines to alicyclic diamines.

A process for preparing 1, 3 - cyclohexyl dimethylamine method

The invention relates to a process for preparing 1, 3 - cyclohexyl dimethylamine method, in the same solvent under a two-stage hydrogenation, 1st stage hydrogenation to Raney nickel as catalyst, methanol, methylamine or 1, 4 - dioxane in one or several kinds of solvent, organic amine, liquid ammonia, water or sodium hydroxide as adjuvant, the reaction temperature is 40 - 80 °C, the reaction pressure is 5 - 8 mpa lower, isophthalonitrile and hydrogen to carry out the reaction, the reaction time is 1 - 5 h, xylylene amine reaction solution obtained, 2nd section carries the ruthenium hydrogenation by load of the active carbon as catalyst, when the reaction temperature is 80 - 130 °C, reaction pressure is 5 - 8 mpa lower, a xylylene amine reaction liquid and hydrogen to continue to carry out the reaction, the reaction time is 1 - 6 h, preparation of the 1, 3 - cyclohexyl dimethylamine. The total yield of the present invention can be up to 90%. The technological process is simple, high yield, easy to rectification, can be directly in the prior MXDA production process is improved on, easy industrialization.