[ CAS No. 894493-95-9 ] {[proInfo.proName]}

Name: 894493-95-9|(1S,2S)-N1,N1-Dimethylcyclohexane-1,2-diamine|98%
Brand: Ambeed
SKU: A269028
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Quality Control of [ 894493-95-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 894493-95-9 ]

SDS Specification

Alternatived Products of [ 894493-95-9 ]

Product Details of [ 894493-95-9 ]

CAS No. :	894493-95-9	MDL No. :	MFCD09952017
Formula :	C₈H₁₈N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FRDZGSBXKJXGNR-YUMQZZPRSA-N
M.W :	142.24	Pubchem ID :	12188264
Synonyms :

Calculated chemistry of [ 894493-95-9 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	44.06
TPSA :	29.26 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.7 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.12
Log Po/w (XLOGP3) :	0.66
Log Po/w (WLOGP) :	0.82
Log Po/w (MLOGP) :	0.9
Log Po/w (SILICOS-IT) :	0.35
Consensus Log Po/w :	0.97

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.07
Solubility :	12.1 mg/ml ; 0.0848 mol/l
Class :	Very soluble
Log S (Ali) :	-0.85
Solubility :	20.1 mg/ml ; 0.141 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.81
Solubility :	21.9 mg/ml ; 0.154 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.94

Safety of [ 894493-95-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 894493-95-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 894493-95-9 ]
Downstream synthetic route of [ 894493-95-9 ]

[ 894493-95-9 ] Synthesis Path-Upstream 1~2

1
[ 620597-07-1 ]
[ 124-63-0 ]
[ 100-46-9 ]
[ 894493-95-9 ]

Yield	Reaction Conditions	Operation in experiment
65%	With sodium hydroxide; HClO₄; NaH; dimethyl amine In tetrahydrofuran; mineral oil	B. trans-N,N-Dimethyl-1,2-cyclohexanediamine STR62 A solution of trans-2-dimethylamiocyclohexanol (58 g.; 0.405 mole) in 80 ml. of THF was added during 10 minutes to a suspension of NaH (17.05 g.; 0.405 mole of 57percent dispersion in mineral oil) in 240 ml. of THF and the mixture was refluxed for 3 hours. It was cooled to 10°, and methanesulfonyl chloride (46.39 g.; 0.405 mole) was added dropwise during 30 minutes keeping the temperature below 15°. Benzylamine (86.79 g.; 0.81 mole) was then added during 5 minutes, the solvent was evaporated and heating continued at 90° for 16 hours. NaOH (500 ml. of 20percent solution) was added and the mixture heated at 95° for 1 hour, cooled and extracted with ether (5 * 100 ml.). The ether solution was extracted with 10percent HCl (6 * 100 ml.) and backwashed once with ether (discard). The acid extract was cooled, basified with 20percent NaOH and extracted well with ether. The ether solution was washed with H₂ O, saturated salt solution, dried (MgSO₄) and evaporated. Distillation at 0.4 mm gave 61 g. (65percent yield) of N,N-dimethyl-N'-benzyl-1,2-cyclohexanediamine, b.p. 112°. It was identical by tlc to the sample prepared by the reaction of benzylamine with trans-2-chloro-dimethyl-aminocyclohexane. A solution of the benzylamino compound was hydrogenated in two batches each containing 30.5 g. (0.131 mole), 175 ml. EtOH, 3.4 g Pd-C and 56.5 g. (0.394 mole) of 70percent HClO₄, at initial pressure of 51.5 p.s.i. for 19 hours. The two batches were combined, filtered through Celite and evaporated in vacuo at 45°. The residue was cooled in ice, basified with 40percent KOH to pH 11. The resulting thick suspension was extracted with ether (5 * 200 ml), the ether extract was dried (MgSO₄) and evaporated through a 9 inches Vigreux. The residue was distilled at 13 mm to give 32.5 g. (87percent yield), b.p. 77°-78.5°. Vpc 100percent at 3.8 mm. ir and nmr was identical to those of the sample prepared by the reaction of 7-azabicyclo[3.1.0]heptane with dimethylamine.

Reference： [1] Patent: US4098904, 1978, A,

2
[ 286-18-0 ]
[ 931-15-7 ]
[ 894493-95-9 ]

Yield	Reaction Conditions	Operation in experiment
46%	With chlorosulfonic acid; sodium hydroxide; dimethyl amine In chloroform-d1	C. trans-N,N-Dimethyl-1,2-cyclohexanediamine STR37 The starting 7-azabicyclo[4.1.0]heptane was best prepared according to the procedure of D. E. Paris and P. E. Fanta, JACS, 74, 3007 (1952) from trans-2-aminocyclohexanol with chlorosulfonic acid, followed by heating with aqueous sodium hydroxide. For the reaction with dimethylamine the procedure described in Bull. Soc. Chim., France, 382 (1956) was followed. A mixture of 7-azabicyclo[4.1.0]heptane (12 g.; 0.124 mole), 40 ml. of aqueous dimethylamine and 0.2 g. of ammonium chloride (NH₄ Cl) was stirred and heated on the steam bath for 18 hours and partly evaporated at room temperature in vacuo. Sodium hydroxide (NaOH) was added and the mixture extracted with ether. The extract was dried (MgSO₄) and evaporated. Distillation at 16 mm gave 8.1 g. (46percent yield) of the titled compound as a colorless oil. nmr in CDCl₃ (100 MHz) was in accord. Mass spectrum (M-8705) M⁺ 142.

Reference： [1] Patent: US4215114, 1980, A,

[ 894493-95-9 ] Synthesis Path-Downstream 1~88

1
(aR)-3-(2-isothiocyanato-phenyl)-4-methyl-thiazoline-2-thione [ No CAS ]
[ 894493-95-9 ]
(aR)-1-((1S,2S)-2-dimethylamino-cyclohexyl)-3-[2-(4-methyl-2-thioxo-thiazol-3-yl)-phenyl]-thiourea [ No CAS ]

Reference： [1]Tetrahedron Asymmetry,2006,vol. 17,p. 999 - 1006

2
[ 894493-95-9 ]
[ 1645-65-4 ]
C₁₆H₂₂F₃N₃S [ No CAS ]

Reference： [1]Tetrahedron,2007,vol. 63,p. 5123 - 5128

3
[ 894493-95-9 ]
[ 1544-68-9 ]
C₁₅H₂₂FN₃S [ No CAS ]

Reference： [1]Tetrahedron,2007,vol. 63,p. 5123 - 5128

4
[ 894493-95-9 ]
[ 23165-29-9 ]
1-[3,5-bis(trifluoromethyl)phenyl]-3-[(1S,2S)-2-(dimethylamino)cyclohexyl]thiourea [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2006,vol. 4,p. 2097 - 2099
[2]Organic and Biomolecular Chemistry,2015,vol. 13,p. 5591 - 5596
[3]Organic Letters,2014,vol. 16,p. 2184 - 2187
[4]Tetrahedron,2007,vol. 63,p. 5123 - 5128
[5]Chemistry - A European Journal,2010,vol. 16,p. 450 - 455

5
7-azabicyclo[3.1.0]heptane [ No CAS ]
trans-2-chloro-dimethyl-aminocyclohexane [ No CAS ]
[ 620597-07-1 ]
[ 124-63-0 ]
[ 100-46-9 ]
[ 894493-95-9 ]

Yield	Reaction Conditions	Operation in experiment
65%	With sodium hydroxide; HClO4; NaH; dimethyl amine;Pd-C; In tetrahydrofuran; mineral oil;	B. trans-N,N-Dimethyl-1,2-cyclohexanediamine STR62 A solution of trans-2-dimethylamiocyclohexanol (58 g.; 0.405 mole) in 80 ml. of THF was added during 10 minutes to a suspension of NaH (17.05 g.; 0.405 mole of 57% dispersion in mineral oil) in 240 ml. of THF and the mixture was refluxed for 3 hours. It was cooled to 10, and methanesulfonyl chloride (46.39 g.; 0.405 mole) was added dropwise during 30 minutes keeping the temperature below 15. Benzylamine (86.79 g.; 0.81 mole) was then added during 5 minutes, the solvent was evaporated and heating continued at 90 for 16 hours. NaOH (500 ml. of 20% solution) was added and the mixture heated at 95 for 1 hour, cooled and extracted with ether (5 * 100 ml.). The ether solution was extracted with 10% HCl (6 * 100 ml.) and backwashed once with ether (discard). The acid extract was cooled, basified with 20% NaOH and extracted well with ether. The ether solution was washed with H2 O, saturated salt solution, dried (MgSO4) and evaporated. Distillation at 0.4 mm gave 61 g. (65% yield) of N,N-dimethyl-N'-benzyl-1,2-cyclohexanediamine, b.p. 112. It was identical by tlc to the sample prepared by the reaction of benzylamine with trans-2-chloro-dimethyl-aminocyclohexane. A solution of the benzylamino compound was hydrogenated in two batches each containing 30.5 g. (0.131 mole), 175 ml. EtOH, 3.4 g Pd-C and 56.5 g. (0.394 mole) of 70% HClO4, at initial pressure of 51.5 p.s.i. for 19 hours. The two batches were combined, filtered through Celite and evaporated in vacuo at 45. The residue was cooled in ice, basified with 40% KOH to pH 11. The resulting thick suspension was extracted with ether (5 * 200 ml), the ether extract was dried (MgSO4) and evaporated through a 9 inches Vigreux. The residue was distilled at 13 mm to give 32.5 g. (87% yield), b.p. 77-78.5. Vpc 100% at 3.8 mm. ir and nmr was identical to those of the sample prepared by the reaction of 7-azabicyclo[3.1.0]heptane with dimethylamine.

Reference： [1]Patent: US4098904,1978,A

6
[ 286-18-0 ]
aqueous dimethylamine [ No CAS ]
ammonium chloride (NH₄ Cl) [ No CAS ]
[ 931-15-7 ]
[ 894493-95-9 ]

Yield	Reaction Conditions	Operation in experiment
46%	With chlorosulfonic acid; sodium hydroxide; dimethyl amine; In chloroform-d1;	C. trans-N,N-Dimethyl-1,2-cyclohexanediamine STR37 The starting 7-azabicyclo[4.1.0]heptane was best prepared according to the procedure of D. E. Paris and P. E. Fanta, JACS, 74, 3007 (1952) from trans-2-aminocyclohexanol with chlorosulfonic acid, followed by heating with aqueous sodium hydroxide. For the reaction with dimethylamine the procedure described in Bull. Soc. Chim., France, 382 (1956) was followed. A mixture of 7-azabicyclo[4.1.0]heptane (12 g.; 0.124 mole), 40 ml. of aqueous dimethylamine and 0.2 g. of ammonium chloride (NH4 Cl) was stirred and heated on the steam bath for 18 hours and partly evaporated at room temperature in vacuo. Sodium hydroxide (NaOH) was added and the mixture extracted with ether. The extract was dried (MgSO4) and evaporated. Distillation at 16 mm gave 8.1 g. (46% yield) of the titled compound as a colorless oil. nmr in CDCl3 (100 MHz) was in accord. Mass spectrum (M-8705) M+ 142.

Reference： [1]Patent: US4215114,1980,A

7
[ 894493-95-9 ]
cis-N,N-dimethyl-1,2-cyclopentanediamine [ No CAS ]
[ 621-84-1 ]

Yield	Reaction Conditions	Operation in experiment
	Pd on carbon;	D. cis-N,N-dimethyl-1,2-cyclopentanediamine The benzyl carbamate obtained in the previous step C (7.9 g.,) was dissolved in 200 ml. ether, treated with 10% Pd on carbon (2.0 g.) and hydrogenated at Ca. 50 psi for 72 hours. The solution was filtered and the ether removed by distillation. The residue was distilled at reduced pressure to give 1.5 g., (7% overall yield) of the titled diamine, b.p. 90-100/30 mm. ir NH 3300; CH 2940, 2850; N-alkyl 2750; NH def 1590; CH 1460, 1440; CN/other 1350, 1265, 1200, 1140, 1105, 1070, 1040, 900; nmr (CDCl3) was in accord. Mass spectrum M+ 128.

Reference： [1]Patent: US4215114,1980,A

8
[ 894493-95-9 ]
[ 14152-97-7 ]
[ 1133834-54-4 ]

Reference： [1]Synlett,2008,p. 3242 - 3246

9
[ 894493-95-9 ]
[ 77489-36-2 ]
[ 1133834-55-5 ]

Reference： [1]Synlett,2008,p. 3242 - 3246

10
[ 894493-95-9 ]
[ 77489-36-2 ]
[ 1133834-56-6 ]

Reference： [1]Synlett,2008,p. 3242 - 3246

11
[ 894493-95-9 ]
[ 530-62-1 ]
[ 196929-78-9 ]
[ 1165796-67-7 ]

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 8754 - 8755

12
[ 894493-95-9 ]
[ 530-62-1 ]
[ 669091-08-1 ]
[ 1165796-68-8 ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: A suspension of potassium hydride (3 equiv) in THF (0.6 M) was cooled in an ice-water bath. A solution of sulfonamide, sulfonamide or aniline (1.0 equiv) in THF (0.20 M) was added dropwise, and the suspension was stirred for 15 min. 1,1'-Carbonyldiimidazole (1.0 equiv) was dissolved in 1:1 THF/dioxane (0.20 M) and added dropwise to the reaction mixture, resulting in the formation of a white precipitate. The ice-water bath was removed, and the reaction mixture was allowed to warm to ambient temperature and was stirred for 2 h. A solution of diamine S-1 (1.0 equiv) in THF (1.0 M) was added dropwise, and the suspension was stirred at room temperature for 20 h. The reaction was quenched with a solution of acetic acid (3 equiv) in THF (1.0 M). The crude product was concentrated in vacuo and purified by silica gel chromatography.

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 8754 - 8755
[2]Tetrahedron,2012,vol. 68,p. 2704 - 2712

13
1,1,1 -trifluoro-2-isothiocyanatoethane [ No CAS ]
[ 894493-95-9 ]
[ 1211566-71-0 ]