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101-83-7

Basic Information
CAS No.: 101-83-7
Name: Cyclohexanamine,N-cyclohexyl-
Article Data: 258
Cas Database
Molecular Structure:
Molecular Structure of 101-83-7 (Cyclohexanamine,N-cyclohexyl-)
Formula: C12H23N
Molecular Weight: 181.321
Synonyms: Dodecahydrodiphenylamine;N,N-Dicyclohexylamine;N-Cyclohexylcyclohexanamine;NSC 3399;Dicyclohexylamine(8CI);Aminodicyclohexane;Bis(cyclohexyl)amine;D-CHA-T;
EINECS: 202-980-7
Density: 0.912 g/cm3
Melting Point: -2 °C
Boiling Point: 256.1 °C at 760 mmHg
Flash Point: 96.1 °C
Solubility: 1 g/L (20 °C) in water
Appearance: Colorless liquid
Hazard Symbols: CorrosiveC,DangerousN
Risk Codes: 22-34-50/53
Safety: 26-36/37/39-45-60-61
Transport Information: UN 2565 8/PG 3
PSA: 12.03000
LogP: 3.63230
Synthetic route
62-53-3

aniline

A

110-82-7

cyclohexane

B

108-91-8

cyclohexylamine

C

101-83-7

N-cyclohexyl-cyclohexanamine

D

110-83-8

cyclohexene

Conditions
ConditionsYield
With ammonia; hydrogen at 180 - 200℃;A n/a
B 98.4%
C 0.08%
D n/a
With hydrogen at 160 - 200℃; under 150015 Torr;A n/a
B 95.9%
C 0.45%
D n/a
62-53-3

aniline

A

108-91-8

cyclohexylamine

B

101-83-7

N-cyclohexyl-cyclohexanamine

Conditions
ConditionsYield
With lithium hydroxide; hydrogen; 5% ruthenium/lithium aluminate In water at 150℃; under 44718.8 Torr; for 2.08333h; Product distribution / selectivity; Neat (no solvent);A 97.1%
B 1%
With lithium hydroxide; hydrogen; 5% activated charcoal-supported ruthenium catalyst In water at 150℃; under 44718.8 Torr; for 1.21667h; Product distribution / selectivity; Neat (no solvent);A 91.8%
B 5.73%
With hydrogen; 5% ruthenium/lithium aluminate at 150℃; under 44718.8 Torr; for 1.28333 - 3h; Product distribution / selectivity; Neat (no solvent);A 89.2%
B 0.08%

dicyclohexyl-(3-methylbut-2-enyl)amine

101-83-7

N-cyclohexyl-cyclohexanamine

Conditions
ConditionsYield
Stage #1: dicyclohexyl-(3-methylbut-2-enyl)amine With 2,2'-azobis(isobutyronitrile); para-thiocresol In benzene Heating;
Stage #2: With hydrogenchloride
97%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane; water at 20℃; for 4h; chemoselective reaction;95%
39830-56-3

N,N-dicyclohexyl-p-toluenesulfonamide

101-83-7

N-cyclohexyl-cyclohexanamine

Conditions
ConditionsYield
With pyrrolidine; samarium diiodide; water In tetrahydrofuran at 20℃; Inert atmosphere;96%
With naphthalene; tetraethylammonium bromide In N,N-dimethyl-formamide at 0℃; Inert atmosphere; Electrolysis;96%
Stage #1: N,N-dicyclohexyl-p-toluenesulfonamide With Na/K absorbed into silica gel In tetrahydrofuran at 20℃; Inert atmosphere;
Stage #2: With water In tetrahydrofuran
83%
With diammonium hydrogenphosphate In tetrahydrofuran at 20℃; Product distribution / selectivity; Cooling with ice;80%
108-91-8

cyclohexylamine

101-83-7

N-cyclohexyl-cyclohexanamine

Conditions
ConditionsYield
With {[(PCy3)(CO)RuH]4(μ-O)(μ-OH)2}; 4-tert-Butylcatechol In chlorobenzene at 130℃; for 16h; Glovebox; Schlenk technique; Sealed tube; chemoselective reaction;95%
With tris(triphenylphosphine)ruthenium(II) chloride In tetrahydrofuran at 185℃; for 5h;92%
With NiCuFeO(x) In 5,5-dimethyl-1,3-cyclohexadiene for 24h; Inert atmosphere; Sealed tube; Reflux;82%

((E)-But-2-enyl)-dicyclohexyl-amine

101-83-7

N-cyclohexyl-cyclohexanamine

Conditions
ConditionsYield
Stage #1: ((E)-But-2-enyl)-dicyclohexyl-amine With 2,2'-azobis(isobutyronitrile); para-thiocresol In benzene Heating;
Stage #2: With hydrogenchloride
95%

N,N-dicyclohexylbenzylamine

101-83-7

N-cyclohexyl-cyclohexanamine

Conditions
ConditionsYield
With formic acid; potassium hydroxide In ethanol at 70℃; for 1h;93%
With Pd(OH)2/C In methanol for 8h; Reflux;62%
108-91-8

cyclohexylamine

108-93-0

cyclohexanol

101-83-7

N-cyclohexyl-cyclohexanamine

Conditions
ConditionsYield
With NiCuFeO(x) In 5,5-dimethyl-1,3-cyclohexadiene for 24h; Inert atmosphere; Sealed tube; Reflux;92%
With lithium hydroxide In neat (no solvent) at 140℃; for 48h; Inert atmosphere;74%
With nickel at 180 - 190℃; im Ruehrautoklaven;
With thorium dioxide at 290 - 320℃;
108-93-0

cyclohexanol

101-83-7

N-cyclohexyl-cyclohexanamine

Conditions
ConditionsYield
With urea In 1,3,5-trimethyl-benzene at 141℃; under 760.051 Torr; for 16h; Inert atmosphere;92%
With ammonium tetrafluroborate; sodium hydrogencarbonate; bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] at 140℃; for 17h;86%
With [Cp*Ir(NH3)3]I2; ammonia In water at 140℃; for 24h; Autoclave; Inert atmosphere;85%

N,N-dicyclohexyltrimethylmethanesulfonamide

101-83-7

N-cyclohexyl-cyclohexanamine

Conditions
ConditionsYield
With trifluorormethanesulfonic acid; methoxybenzene In dichloromethane at 0℃; desulfonation;92%
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Consensus Reports

IARC Cancer Review: Group 3 IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 (1987),p. 178.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Inadequate Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 22 (1980),p. 55.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . Reported in EPA TSCA Inventory.

Standards and Recommendations

DOT Classification:  8; Label: Corrosive

Specification

The N,N-Dicyclohexylamine, with the CAS registry number 101-83-7, is also known as Dodecahydrodiphenylamine. It belongs to the product categories of Pharmaceutical Intermediates; Amines; C11 to C38; Nitrogen Compounds; Aliphatics Volatiles/ Semivolatiles; Alpha Sort; Chemical Class; D; DAlphabetic; DIA - DIC; Analytical Reagents for General Use; C-D, Puriss p.a.; Puriss p.a.. Its EINECS registry number is 202-980-7. This chemical's molecular formula is C12H23N and molecular weight is 181.31772. Its IUPAC name is called N-cyclohexylcyclohexanamine. This chemical's classification codes are Enzyme inhibitors; Mutation Data; Skin / Eye Irritant; Tumor Data.

Physical properties of N,N-Dicyclohexylamine: (1)ACD/LogP: 3.69; (2)ACD/LogD (pH 5.5): 0.59; (3)ACD/LogD (pH 7.4): 0.64; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 1.92; (7)ACD/KOC (pH 7.4): 2.15; (8)#H bond acceptors: 1; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 2; (11)Index of Refraction: 1.487; (12)Molar Refractivity: 57.12 cm3; (13)Molar Volume: 198.2 cm3; (14)Surface Tension: 33.1 dyne/cm; (15)Density: 0.91 g/cm3; (16)Flash Point: 96.1 °C; (17)Enthalpy of Vaporization: 49.36 kJ/mol; (18)Boiling Point: 256.1 °C at 760 mmHg; (19)Vapour Pressure: 0.0157 mmHg at 25°C.

Preparation of N,N-Dicyclohexylamine: this chemical can be prepared by aniline. This reaction will need reagent nickel catalyst.

N,N-Dicyclohexylamine can be prepared by aniline

Uses of N,N-Dicyclohexylamine: it can be used to produce chloro-acetic acid dicyclohexylamide at temperature of 25 °C. This reaction will need reagent CH2Cl2 with reaction time of 12 hours. The yield is about 61%.

N,N-Dicyclohexylamine can be used to produce chloro-acetic acid dicyclohexylamide

When you are using this chemical, please be cautious about it as the following:
This chemical may destroy living tissue on contact and may cause burns. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective clothing, gloves and eye/face protection.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: C1CCC(CC1)NC2CCCCC2
(2)InChI: InChI=1S/C12H23N/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h11-13H,1-10H2
(3)InChIKey: XBPCUCUWBYBCDP-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 oral 500mg/kg (500mg/kg)   "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 468, 1986.
mouse LD50 subcutaneous 135mg/kg (135mg/kg)   Voprosy Onkologii. Problems of Oncology. For English translation, see PONCAU. Vol. 4, Pg. 659, 1958.
rabbit LDLo subcutaneous 500mg/kg (500mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Industrial and Engineering Chemistry. Vol. 29, Pg. 1247, 1937.
rat LD50 oral 373mg/kg (373mg/kg)   "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 468, 1986.

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