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1,2-Diaminocyclohexane

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Name

1,2-Diaminocyclohexane

EINECS 211-776-7
CAS No. 694-83-7 Density 0.939 g/cm3
PSA 52.04000 LogP 1.61560
Solubility miscible with water Melting Point 41-45 °C
Formula C6H14N2 Boiling Point 193.643 °C at 760 mmHg
Molecular Weight 114.22 Flash Point 75 °C
Transport Information UN 3259 8/PG 2 Appearance clear slightly yellow to yellow liquid
Safety 26-36/37/39-45 Risk Codes 34
Molecular Structure Molecular Structure of 694-83-7 (1,2-CYCLOHEXANEDIAMINE) Hazard Symbols CorrosiveC
Synonyms

1,2-Cyclohexanediamine;DHC 99;Dytek DCH 99;

 

1,2-Diaminocyclohexane Synthetic route

286-20-4

cyclohexane-1,2-epoxide

694-83-7

1,2-diaminocyclohexane

Conditions
ConditionsYield
With palladium on activated charcoal; ammonia; hydrogen In water at 110 - 250℃; under 18751.9 Torr; Pressure; Temperature; Solvent; Reagent/catalyst; Autoclave;95%
34126-95-9

2-aminocyclohexanecarboxamide

694-83-7

1,2-diaminocyclohexane

Conditions
ConditionsYield
With potassium hypobromite und Erwaermen des Reaktionsprodukts mit Salzsaeure; es liefert die freie Base mit KOH;
32003-11-5

cyclohexane-1,2-dicarboxylic acid dihydrazide

694-83-7

1,2-diaminocyclohexane

Conditions
ConditionsYield
beim Abbau nach Curtius; cis(?)-hexahydrophthalic acid dihydrazide;
26593-33-9

1,2-diazidocyclohexane

694-83-7

1,2-diaminocyclohexane

Conditions
ConditionsYield
With hydrogen; platinum(IV) oxide In methanol

N-(1-Ureido-ethyliden)-trans-2-chlor-cyclohexylamin

694-83-7

1,2-diaminocyclohexane

Conditions
ConditionsYield
With sodium hydroxide In ethylene glycol Heating;
110-83-8

cyclohexene

694-83-7

1,2-diaminocyclohexane

Conditions
ConditionsYield
With lithium aluminium tetrahydride; 2; nitrogen(II) oxide 1) THF, 0 deg C, 120 min; 2) THF, -70 deg C, room temperature (overnight), reflux (1 h); Yield given. Multistep reaction;

O-Ethyl-N-(2-nitro-cyclohexyl)-hydroxylamine

694-83-7

1,2-diaminocyclohexane

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethanol under 760 Torr; Ambient temperature; Yield given;
96058-39-8

2,3-diphenyl-4a,5,6,7,8,8a-hexahydroquinoxaline

mineral acid

mineral acid

A

694-83-7

1,2-diaminocyclohexane

B

134-81-6

benzil

2562-37-0

1-nitrocyclohexene

694-83-7

1,2-diaminocyclohexane

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NaHCO3 / tetrahydrofuran / Ambient temperature
2: H2 / 10percent Pd/C / ethanol / 760 Torr / Ambient temperature
View Scheme
64162-07-8

2-amino-cyclohexanecarboxylic acid ethyl ester

694-83-7

1,2-diaminocyclohexane

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 145 °C / im geschlossenen Rohr
2: potassium hypobromite / und Erwaermen des Reaktionsprodukts mit Salzsaeure; es liefert die freie Base mit KOH
View Scheme
110-83-8

cyclohexene

/PBNAI150--221/

/PBNAI150--221/

694-83-7

1,2-diaminocyclohexane

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NaN3, Fe2(SO4)3, FeSO4, aq. H2O2 / methanol
2: H2 / PtO2 / methanol
View Scheme
Multi-step reaction with 2 steps
1: (i) Cl2, (ii) /BRN= 906737/
2: aq. NaOH / ethane-1,2-diol / Heating
View Scheme
99-14-9

tricarallylic acid

platinum(II) chloride

694-83-7

1,2-diaminocyclohexane

Conditions
ConditionsYield
With silver nitrate In potassium hydroxide; water
95-54-5

1,2-diamino-benzene

694-83-7

1,2-diaminocyclohexane

Conditions
ConditionsYield
With sodium tetrahydroborate; ammonia; hydrogen; 5% Rh/C In water at 125℃; under 52476.2 - 104192 Torr; for 3h; Product distribution / selectivity; Autoclave;
With hydrogen In tetrahydrofuran at 110℃; under 75007.5 Torr; for 3h; Autoclave;
With hydrogen In tetrahydrofuran at 130℃; under 37503.8 Torr; for 24h; Autoclave; Green chemistry; chemoselective reaction;

N,N'-bis(salicylidene)cyclohexane-1,2-diamine

A

90-02-8

salicylaldehyde

B

694-83-7

1,2-diaminocyclohexane

Conditions
ConditionsYield
In chloroform-d1 for 1h; UV-irradiation;

1-(2-azidocyclohexyl)-2-(4-methoxyphenyl)diazene

694-83-7

1,2-diaminocyclohexane

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; for 9h;69 mg
86119-84-8, 7664-38-2

phosphoric acid

557-34-6

zinc diacetate

694-83-7

1,2-diaminocyclohexane

Zn3(PO4)2(PO3OH)(H2-1,2-diaminocyclohexane)*2H2O

Conditions
ConditionsYield
In water hydrothermal conditions, 180°C;100%
10196-18-6

zinc(II) nitrate

86119-84-8, 7664-38-2

phosphoric acid

694-83-7

1,2-diaminocyclohexane

Zn3(PO4)2(PO3OH)(H2-1,2-diaminocyclohexane)*2H2O

Conditions
ConditionsYield
In water hydrothermal conditions, 180°C;100%

boron phosphate

557-34-6

zinc diacetate

694-83-7

1,2-diaminocyclohexane

Zn3(PO4)2(PO3OH)(H2-1,2-diaminocyclohexane)*2H2O

Conditions
ConditionsYield
In water hydrothermal conditions, molar ratio BPO4:Zn(OAc)2:diaminocyclohexane:water 2:1:2.5:117, , pH=8, 210°C; elem. anal.;100%
694-83-7

1,2-diaminocyclohexane

90-60-8

3,5-dichlorosalicyclaldehyde

413580-19-5

N,N'-bis(3,5-dichlorosalicylidene)-1,2-cyclohexanediamine

Conditions
ConditionsYield
In ethanol at 60℃;100%
In ethanol Reflux;

2-hydroxy-3-methyl-1-naphthaldehyde

694-83-7

1,2-diaminocyclohexane

C30H30N2O2

Conditions
ConditionsYield
In ethanol Reflux;100%

3-ethyl-2-hydroxy-1-naphthaldehyde

694-83-7

1,2-diaminocyclohexane

C32H34N2O2

Conditions
ConditionsYield
In ethanol Reflux;100%
147-71-7

D-tartaric acid

694-83-7

1,2-diaminocyclohexane

(R,R)-1,2-diaminocyclohexane tartrate

Conditions
ConditionsYield
With acetic acid In water99%
202289-10-9, 55669-28-8

trans-{RuCl2(1,3-bis(diphenylphosphino)propane)2}

694-83-7

1,2-diaminocyclohexane

1299494-45-3, 531498-67-6

trans-Cl2Ru(1,3-bis(diphenylphosphino)propane)(C6H10(NH2)2)

Conditions
ConditionsYield
In dichloromethane Ar; dropwise addn. of dichloromethane soln. of diamine to a stirred soln. of Ru complex in the same solvent within 5 min, stirring at room temp.for 10-30 min; filtration, concg. under reduced pressure, pptn. by addn. of diethyl ether, filtration, recrystn. of solid from dichloromethane-n-hexane; elem. anal.;99%
24424-99-5

di-tert-butyl dicarbonate

694-83-7

1,2-diaminocyclohexane

1350724-58-1

di-tert-butyl cyclohexane-1,2-diyldicarbamate

Conditions
ConditionsYield
With iron oxide In ethanol at 20℃; for 0.25h; Green chemistry; chemoselective reaction;99%
With 1,3-disulfonic acid imidazolium hydrogen sulfate In neat (no solvent) at 20℃; for 0.0166667h; Green chemistry; chemoselective reaction;92%
With N-sulfonic acid poly(4-vinyl)pyridinium chloride In neat (no solvent) at 20℃; for 0.0333333h;92%
694-83-7

1,2-diaminocyclohexane

532-55-8

Benzoyl isothiocyanate

CH bis-BTU

Conditions
ConditionsYield
In dichloromethane at 5℃; Inert atmosphere;99%
In dichloromethane at 5 - 20℃; Inert atmosphere;99%
26775-76-8

tricyclo<4.3.1.1.3,8>undecan-4,5-dione

694-83-7

1,2-diaminocyclohexane

106913-34-2

C17H24N2

Conditions
ConditionsYield
In ethanol at 25℃; for 48h;98%
136398-79-3

phenyl (chloromethyl)(isothiocyanato)thiophosphinate

694-83-7

1,2-diaminocyclohexane

C14H20N3OPS2*ClH

Conditions
ConditionsYield
In chloroform at 20℃; for 24h;98%
89-51-0

Homophthalic acid

694-83-7

1,2-diaminocyclohexane

1225210-98-9

C15H16N2O

Conditions
ConditionsYield
for 0.0833333h; Neat (no solvent); Microwave irradiation;98%
108-24-7

acetic anhydride

694-83-7

1,2-diaminocyclohexane

trans-1,2-diacetyldiaminocyclohexane

Conditions
ConditionsYield
With triethylamine at 65 - 80℃; for 6.5h; Temperature; Reagent/catalyst;98%
In water at 65 - 80℃; for 3.5h; Solvent;89%
80-71-7

2-hydroxy-3-methylcyclopent-2-en-1-one

694-83-7

1,2-diaminocyclohexane

C12H18N2

Conditions
ConditionsYield
In ethanol at 80℃;98%
694-83-7

1,2-diaminocyclohexane

134-81-6

benzil

96058-39-8

2,3-diphenyl-4a,5,6,7,8,8a-hexahydroquinoxaline

Conditions
ConditionsYield
With alumina supported sulfuric acid In ethanol at 30℃; for 1h;97%
With potassium hydrogensulfate In ethanol at 20℃; for 0.25h;95%
With N,N,N’,N’-tetrabromobenzene-1,3-disulfonamide In ethanol; water at 20℃; for 0.166667h;95%
694-83-7

1,2-diaminocyclohexane

93-97-0

benzoic acid anhydride

N-(2-aminocyclohexyl)benzamide

Conditions
ConditionsYield
In dichloromethane at -78 - 20℃; for 20h; Inert atmosphere;97%
694-83-7

1,2-diaminocyclohexane

1226-42-2

1,2-bis(4-methoxyphenyl)-1,2-ethanedione

2,3-di-(p-metoxifenil)-4a,5,6,7,8,8a-hexahidroquinoxalina

Conditions
ConditionsYield
With N,N,N’,N’-tetrabromobenzene-1,3-disulfonamide In neat (no solvent) at 80℃; for 0.166667h;96%
In methanol for 1h; Condensation; Heating;
109011-62-3

trans-dichlorobis((2-methoxyethyl)diphenylphosphine-O,P)ruthenium(II)

694-83-7

1,2-diaminocyclohexane

620945-35-9, 620949-90-8

RuCl2((C6H5)2PCH2CH2OCH3)2(H2NC6H10NH2)

Conditions
ConditionsYield
In dichloromethane a soln. of the diamine ligand (10% excess) in CH2Cl2 was added dropwise under Ar to a stirred soln. of Ru-complex in CH2Cl2, the mixt. was stirred for approx. 45 min at room temp.; filtd., concd., Et2O was added, ppt. was filtd. off, dissolved in CH2Cl2, concd., n-hexane was added, ppt. was collected by filtn., washed with n-hexane and dried under vac.; elem. anal.;96%
673-22-3

2-Hydroxy-4-methoxybenzaldehyde

694-83-7

1,2-diaminocyclohexane

1222393-15-8

N,N'-bis(4-methoxysalicylidene)cyclohexane-1,2-diamine

Conditions
ConditionsYield
In methanol at 20℃; for 0.166667h;96%
84405-44-7

2,7-dibromo-phenanthrene-9,10-dione

694-83-7

1,2-diaminocyclohexane

1333212-91-1

2,7-dibromo-10,11,12,13-tetrahydrodibenzo[a,c]phenazine

Conditions
ConditionsYield
Stage #1: 2,7-dibromo-phenanthrene-9,10-dione; rac-diaminocyclohexane In toluene for 1h; Inert atmosphere; Reflux; Dean-Stark;
Stage #2: With manganese(IV) oxide In toluene at 84℃; Inert atmosphere;
96%
With toluene-4-sulfonic acid In ethanol Reflux;49%
19005-93-7

1H-indol-2-ylcarboxaldehyde

694-83-7

1,2-diaminocyclohexane

C24H24N4

Conditions
ConditionsYield
With toluene-4-sulfonic acid In ethanol at 20℃; for 3h;96%
5970-45-6

zinc(II) acetate dihydrate

148-53-8

3-methoxy-2-hydroxybenzaldehyde

694-83-7

1,2-diaminocyclohexane

[(R,R)-N,N’-bis(3-methoxysalicylidene)-1,2-cyclohexanediaminato]zinc(II)

Conditions
ConditionsYield
In ethanol at 20℃; for 24h;96%
124-38-9

carbon dioxide

694-83-7

1,2-diaminocyclohexane

1123-97-3, 7237-97-0, 139121-98-5

(R*,R*)-N,N’-cyclohexa-1,2-diylurea

Conditions
ConditionsYield
at 180℃; under 75007.5 Torr; for 24h; Autoclave;95.9%
With potassium hydroxide at 149.84℃; under 60006 Torr; for 10h; Autoclave;74.2%
824-42-0

2-methoxy-3-methylbenzaldehyde

694-83-7

1,2-diaminocyclohexane

6,6 '-((1E,1'E)-(cyclohexane-1,2- diylbis(azanylylidene))bis(methanylylidene))bis(2-methylphenol)

Conditions
ConditionsYield
In ethanol for 2h; Reflux;95.2%
574-17-4

1-acetyl-1H-indole-2,3-dione

694-83-7

1,2-diaminocyclohexane

81965-12-0

3-(2-Acetamidophenyl)-4a,5,6,7,8,8a-hexahydro-2(1H)-chinoxazolinon

Conditions
ConditionsYield
In ethanol for 2h; Heating;95%
126-81-8

dimedone

694-83-7

1,2-diaminocyclohexane

MC08a

Conditions
ConditionsYield
In toluene for 3h; Heating / reflux;95%
89-01-0

2,3-dicarboxypyrazine

694-83-7

1,2-diaminocyclohexane

1225211-01-7

C12H12N4O

Conditions
ConditionsYield
for 0.0666667h; Neat (no solvent); Microwave irradiation;95%
110-15-6

succinic acid

694-83-7

1,2-diaminocyclohexane

1259371-17-9

C10H14N2O

Conditions
ConditionsYield
for 0.0666667h; Neat (no solvent); Microwave irradiation;95%
694-83-7

1,2-diaminocyclohexane

1,2-diaminocyclohexane monohydrochloride

Conditions
ConditionsYield
With hydrogenchloride In diethyl ether for 2.33333h;95%

1,2-Diaminocyclohexane Specification

1,2-Diaminocyclohexan, with the CAS NO.694-83-7 and the Molecular Formula of C6H14N2, has the other names of trans-1,2-cyclohexanediamine; (+/-)-trans-cyclohexane-1,2-diamine; trans-cyclohexane-1,2-diamine; (+/-)-1,2-diaminocyclohexane; trans-1,2-diaminocyclohexane; trans-1,2-diamiocyclohexane; DACH.  This diamine is a building block for chiral ligands that are useful in asymmetric catalysis.

Physical properties about 1,2-Diaminocyclohexan are: (1)ACD/LogP: 0.171; (2)ACD/LogD (pH 5.5): -3.58; (3)ACD/LogD (pH 7.4): -2.77; (4)ACD/BCF (pH 5.5): 1.00; (5)ACD/BCF (pH 7.4): 1.00; (6)ACD/KOC (pH 5.5): 1.00; (7)ACD/KOC (pH 7.4): 1.00; (8)#H bond acceptors: 2; (9)#H bond donors: 4; (10)#Freely Rotating Bonds: 2; (11)Index of Refraction: 1.484; (12)Molar Refractivity: 34.776 cm3; (13)Molar Volume: 121.597 cm3; (14)Polarizability: 13.786 10-24cm3; (15)Surface Tension: 37.0369987487793 dyne/cm; (16)Density: 0.939 g/cm3; (17)Flash Point: 75 °C; (18)Enthalpy of Vaporization: 42.984 kJ/mol; (19)Boiling Point: 193.643 °C at 760 mmHg; (20)Vapour Pressure: 0.46000000834465 mmHg at 25°C

When you are using this chemical, please be cautious about it as the following:
1. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice;
2. Wear suitable protective clothing, gloves and eye/face protection;
3. In case of accident or if you feel unwell, seek medical advice immediately (show label where possible);

You can still convert the following datas into molecular structure:
(1)InChI=1S/C6H14N2/c7-5-3-1-2-4-6(5)8/h5-6H,1-4,7-8H2;
(2)InChIKey=SSJXIUAHEKJCMH-UHFFFAOYSA-N;
(3)SmilesC1[C@@H]([C@@H](CCC1)N)N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rat LCLo inhalation 3200mg/m3/4H (3200mg/m3)   Toxicologist. Vol. 12, Pg. 357, 1992.
rat LD50 oral 4556mg/kg (4556mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: TREMOR
National Technical Information Service. Vol. OTS0535386,

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