[ CAS No. 21436-03-3 ] {[proInfo.proName]}

Name: 21436-03-3|(1S,2S)-Cyclohexane-1,2-diamine|96%
Brand: Ambeed
SKU: A360682
Price: 5.0 USD
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Quality Control of [ 21436-03-3 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 21436-03-3 ]

Product Details of [ 21436-03-3 ]

CAS No. :	21436-03-3	MDL No. :	MFCD00062986
Formula :	C₆H₁₄N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SSJXIUAHEKJCMH-WDSKDSINSA-N
M.W :	114.19	Pubchem ID :	479307
Synonyms :	(1S,2S)-(+)-1,2-Diaminocyclohexane

Calculated chemistry of [ 21436-03-3 ]

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	34.26
TPSA :	52.04 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.22 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.37
Log Po/w (XLOGP3) :	-0.32
Log Po/w (WLOGP) :	0.21
Log Po/w (MLOGP) :	0.21
Log Po/w (SILICOS-IT) :	0.15
Consensus Log Po/w :	0.33

Druglikeness

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

Water Solubility

Log S (ESOL) :	-0.35
Solubility :	51.4 mg/ml ; 0.45 mol/l
Class :	Very soluble
Log S (Ali) :	-0.31
Solubility :	55.7 mg/ml ; 0.488 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.31
Solubility :	55.8 mg/ml ; 0.489 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.81

Safety of [ 21436-03-3 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P210-P261-P264-P271-P280-P301+P330+P331-P303+P361+P353-P304+P340+P310-P305+P351+P338+P310-P312-P363-P370+P378-P403+P233-P403+P235-P405-P501	UN#:	2735
Hazard Statements:	H227-H303-H314-H335	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 21436-03-3 ]

* 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 [ 21436-03-3 ]
Downstream synthetic route of [ 21436-03-3 ]

[ 21436-03-3 ] Synthesis Path-Upstream 1~21

1
[ 329321-25-7 ]
[ 21436-03-3 ]

Reference： [1] Tetrahedron Letters, 2000, vol. 41, # 51, p. 10079 - 10083

2
[ 1121-22-8 ]
[ 20439-47-8 ]
[ 21436-03-3 ]

Reference： [1] Tetrahedron Asymmetry, 2003, vol. 14, # 18, p. 2763 - 2769
[2] Journal of the American Chemical Society, 2012, vol. 134, # 30, p. 12758 - 12773
[3] CrystEngComm, 2012, vol. 14, # 24, p. 8708 - 8713
[4] Tetrahedron Asymmetry, 2017, vol. 28, # 3, p. 454 - 459

3
[ 1121-22-8 ]
[ 108-59-8 ]
[ 20439-47-8 ]
[ 21436-03-3 ]
[ 186144-56-9 ]

Reference： [1] Organic Letters, 2005, vol. 7, # 18, p. 4045 - 4048

4
[ 1121-22-8 ]
[ 21436-03-3 ]

Reference： [1] Advanced Synthesis and Catalysis, 2014, vol. 356, # 4, p. 818 - 830
[2] Zeitschrift fuer Anorganische und Allgemeine Chemie, 1937, vol. 233, p. 97,98
[3] Proceedings of the Koninklijke Nederlandse Akademie van Wetenschappen, Series B: Physical Sciences, 1937, vol. 40, p. 12[4] Zeitschrift fuer Anorganische und Allgemeine Chemie, 1937, vol. 233, p. 97,99
[5] Gazzetta Chimica Italiana, 1972, vol. 102, p. 855 - 892
[6] Synlett, 2016, vol. 27, # 1, p. 126 - 130

5
[ 87-69-4 ]
[ 21436-03-3 ]

Reference： [1] Patent: US5399771, 1995, A,

6
[ 329321-23-5 ]
[ 21436-03-3 ]

Reference： [1] Tetrahedron Letters, 2000, vol. 41, # 51, p. 10079 - 10083

7
[ 329321-22-4 ]
[ 21436-03-3 ]

Reference： [1] Tetrahedron Letters, 2000, vol. 41, # 51, p. 10079 - 10083

8
[ 1121-22-8 ]
[ 108-59-8 ]
[ 21436-03-3 ]
[ 186144-56-9 ]

Reference： [1] Chemical Communications, 1996, # 21, p. 2471 - 2472

9
[ 1121-22-8 ]
[ 108-59-8 ]
[ 20439-47-8 ]
[ 21436-03-3 ]
[ 186144-56-9 ]

Reference： [1] Chemical Communications, 1996, # 21, p. 2471 - 2472

10
[ 694-83-7 ]
[ 20439-47-8 ]
[ 21436-03-3 ]

Reference： [1] Tetrahedron Asymmetry, 2003, vol. 14, # 21, p. 3297 - 3300

11
[ 492-99-9 ]
[ 21436-03-3 ]

Reference： [1] Zeitschrift fuer Anorganische und Allgemeine Chemie, 1937, vol. 233, p. 97,98
[2] Proceedings of the Koninklijke Nederlandse Akademie van Wetenschappen, Series B: Physical Sciences, 1937, vol. 40, p. 12[3] Zeitschrift fuer Anorganische und Allgemeine Chemie, 1937, vol. 233, p. 97,99

12
[ 694-83-7 ]
[ 21436-03-3 ]

Reference： [1] Acta Chemica Scandinavica, 1996, vol. 50, # 10, p. 918 - 921

13
[ 694-83-7 ]
[ 20439-47-8 ]
[ 1436-59-5 ]
[ 21436-03-3 ]

Reference： [1] Tetrahedron Asymmetry, 2008, vol. 19, # 13, p. 1600 - 1607

14
[ 21436-03-3 ]
[ 61798-24-1 ]

Reference： [1] Tetrahedron, 1996, vol. 52, # 44, p. 13837 - 13866
[2] Helvetica Chimica Acta, 1988, vol. 71, p. 1999 - 2021
[3] Journal of the American Chemical Society, 1984, vol. 106, # 19, p. 5754 - 5756

15
[ 37942-07-7 ]
[ 21436-03-3 ]
[ 135616-40-9 ]

Reference： [1] Patent: US6369223, 2002, B2, . Location in patent: Page column 56

16
[ 24424-99-5 ]
[ 21436-03-3 ]
[ 180683-64-1 ]

Reference： [1] European Journal of Organic Chemistry, 2018, vol. 2018, # 1, p. 99 - 103
[2] Journal of the American Chemical Society, 2011, vol. 133, # 37, p. 14704 - 14709
[3] Journal of the Chemical Society, Dalton Transactions, 2001, # 14, p. 2188 - 2198
[4] Letters in Organic Chemistry, 2010, vol. 7, # 1, p. 15 - 20
[5] Chemistry - A European Journal, 1997, vol. 3, # 6, p. 912 - 919
[6] European Journal of Organic Chemistry, 2015, vol. 2015, # 6, p. 1218 - 1225
[7] Tetrahedron Letters, 2000, vol. 41, # 49, p. 9607 - 9611

17
[ 24424-99-5 ]
[ 21436-03-3 ]
[ 180683-64-1 ]

Reference： [1] Letters in Drug Design and Discovery, 2014, vol. 11, # 6, p. 756 - 761

18
[ 21436-03-3 ]
[ 180683-64-1 ]

Reference： [1] Patent: EP1270557, 2003, A1,

19
[ 58632-95-4 ]
[ 21436-03-3 ]
[ 180683-64-1 ]

Reference： [1] Journal of Medicinal Chemistry, 2008, vol. 51, # 4, p. 721 - 724

20
[ 34619-03-9 ]
[ 21436-03-3 ]
[ 180683-64-1 ]

Reference： [1] Tetrahedron Asymmetry, 2014, vol. 25, # 15, p. 1091 - 1094

21
[ 21436-03-3 ]
[ 317595-54-3 ]

Reference： [1] Patent: US2005/20645, 2005, A1,

[ 21436-03-3 ] Synthesis Path-Downstream 1~88

1
[ 24424-99-5 ]
[ 21436-03-3 ]
[ 180683-64-1 ]

Yield	Reaction Conditions	Operation in experiment
34%	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 24h;Inert atmosphere;	General procedure: A mixture of piperazine (500mg, 5.8mmol, 1.0eq.), N,N-diisopropylethylamine (DIPEA) (1.5mL, 8.7mmol, 1.5eq.), and di-tert-butyl dicarbonate (Boc2O) (500mg, 2.3mmol, 0.4eq.) in dry dichloromethane (15mL) was stirred at room temperature for 24h under nitrogen atmosphere. The reaction mixture was diluted with dichloromethane and washed with saturated aqueous NaHCO3 and brine. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The titled compound (4a) as a colorless solid was afforded after purification by column chromatography on silica gel (chloroform/methanol=50/1). The same procedure was performed to obtain compounds 4b and 4c

Reference： [1]European Journal of Organic Chemistry,2018,vol. 2018,p. 99 - 103
[2]Journal of the American Chemical Society,2011,vol. 133,p. 14704 - 14709
[3]Journal of the American Chemical Society,2019,vol. 141,p. 6302 - 6309
[4]Journal of the Chemical Society, Dalton Transactions,2001,p. 2188 - 2198
[5]Letters in Organic Chemistry,2010,vol. 7,p. 15 - 20
[6]Chemistry - A European Journal,1997,vol. 3,p. 912 - 919
[7]European Journal of Organic Chemistry,2015,vol. 2015,p. 1218 - 1225
[8]Tetrahedron Letters,2000,vol. 41,p. 9607 - 9611
[9]Bioorganic and Medicinal Chemistry,2019,vol. 27,p. 383 - 393

2
[ 21436-03-3 ]
[ 1970-80-5 ]
[ 424829-08-3 ]

Reference： [1]Journal of the Chemical Society, Dalton Transactions,2002,p. 602 - 608

3
[ 35856-62-3 ]
[ 21436-03-3 ]
(1S,2S)-N-(piperidino-N-sulfonyl)-1,2-cyclohexanediamine [ No CAS ]

Reference： [1]Tetrahedron Asymmetry,2002,vol. 13,p. 2605 - 2608

4
[ 37942-07-7 ]
[ 21436-03-3 ]
[ 135616-36-3 ]

Reference： [1]Dalton Transactions,2020,vol. 49,p. 289 - 299
[2]Helvetica Chimica Acta,2002,vol. 85,p. 3301 - 3312

5
[ 7089-68-1 ]
[ 21436-03-3 ]
SS-N,N'-bis(phenanthrolin-2-yl)-1,2-cyclohexanediamine [ No CAS ]

Reference： [1]Chemistry Letters,2004,vol. 33,p. 684 - 685

6
[ 21436-03-3 ]
[ 10111-08-7 ]
(1S,2S)-N-[1-(1H-Imidazol-2-yl)-meth-(Z)-ylidene]-N'-[1-(1H-imidazol-2-yl)-meth-(E)-ylidene]-cyclohexane-1,2-diamine [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2005,p. 4995 - 5000

7
[ 960299-07-4 ]
[ 21436-03-3 ]
[ 19578-68-8 ]
(1S,2S)-N₁-(4-(benzyloxy)phenyl)cyclohexane-1,2-diamine [ No CAS ]
[ 960299-08-5 ]

Yield	Reaction Conditions	Operation in experiment
63%		To a mixture of 5-methyl-6-(phenylamino)pyrimidin- 4(3H)-one (0.025 g, 0.124 mmol) and l-(benzyloxy)-4-iodobenzene (0.046 g, 0.149 mmol) in dioxane (500 muL) and DMF (~ 4 drops) was added copper (I) iodide (0.005 g, 0.024 mmol), (lS,2S)-cyclohexane-l,2-diamine (0.006 ml, 0.050 mmol), and K3PO4 (0.053 g, 0.248 mmol). <n="117"/>111-03-PCT- P2338R1 - 02120.004WO1116The mixture was flushed with N2 and stirred at 110C for 5 hours, when LC-MS showed some formation of desired product as well as formation of (lS,2S)-Nl-(4- (benzyloxy)phenyl)cyclohexane-l,2-diamine from coupling of ligand to l-(benzyloxy)-4- iodobenzene. Because the reaction had stalled from ligand and l-(benzyloxy)-4-iodobenzene being depleted, the secondary ligand Nl,N2-dimethylethane-l,2-diamine (0.0132 ml, 0.124 mmol) and additional l-(benzyloxy)-4-iodobenzene (0.020 g, 0.065 mmol) were added. The reaction mixture was then stirred at 1100C for an additional 16 hours. The reaction mixture was partitioned between EtOAc and saturated aqueous NaCl. The phases were separated, and the aqueous phase was re-extracted with EtOAc (Ix). The combined organic layers were dried (Na2SO4), filtered and concentrated. The crude product was purified by silica gel flash column chromatography, eluting with 10:1 dichloromethane/EtOAc. The desired product (0.030 g, 63%) was obtained as a white foamy solid. 1H-NMR (400 MHz, DMSO-d6) delta 8.25 (s, IH), 8.11 (s, IH), 7.49-7.38 (m 6H), 7.37-7.25 (m, 5H), 7.11 (m, 2H), 7.01 (m, IH), 5.17 (s, 2H), 1.98 (s, 3H). LRMS (ESI pos) m/e 384 (M+l).

Reference： [1]Patent: WO2007/146824,2007,A2 .Location in patent: Page/Page column 115; 116

8
[ 21436-03-3 ]
[ 34595-26-1 ]
(1S,2S)-N¹,N²-bis(2-(piperidin-1-yl)benzylidene)cyclohexane-1,2-diamine [ No CAS ]

Reference： [1]Tetrahedron Asymmetry,2007,vol. 18,p. 729 - 733

9
[ 14562-10-8 ]
[ 21436-03-3 ]
C₃₂H₃₀N₂O₂ [ No CAS ]

Reference： [1]Chemistry - A European Journal,2007,vol. 13,p. 8045 - 8050

10
[ 21436-03-3 ]
[ 7310-97-6 ]
(2S,3S,12S,13S,22S,23S)-1,4,11,14,21,24-hexaaza-(2,3:12,13:22,23)-tributano-7,8',17,18',27,28'-hexamethoxy-(6,9:16,19:26,29)-trietheno-2H,3H,12H,13H,22H,23H-hexahydro-⁽³⁰⁾-annulene [ No CAS ]

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,2007,vol. 50,p. 1215 - 1223

11
[ 21436-03-3 ]
[ 61798-24-1 ]

Reference： [1]Tetrahedron,1996,vol. 52,p. 13837 - 13866
[2]Helvetica Chimica Acta,1988,vol. 71,p. 1999 - 2021
[3]Journal of the American Chemical Society,1984,vol. 106,p. 5754 - 5756

12
[ 37942-07-7 ]
[ 21436-03-3 ]
[ 135616-40-9 ]

Reference： [1]Patent: US6369223,2002,B2 .Location in patent: Page column 56

13
[ 21436-03-3 ]
[ 107-13-1 ]
(1S,2S)-bis-[N-(2-cyanoethyl)-amino]-cyclohexane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	In ethanol; at 20℃; for 72h;	1,0 g (1S,2S)-(+)-Diaminocyclohexan (8.8 mmol) werden bei Raumtemperatur in 10 ml Ethanol gelost. Man fugt 1,24 ml Acrylnitril (1,0 g, 18,8 mmol) hinzu und ruhrt 72 h bei Raumtemperatur. Laut gaschromatographischer Analyse ist das Diaminocyclohexan vollstandig umgesetzt worden. Nach Destillation des Alkohols verbleibt ein farbloses Ol (1,8 g), welches laut gaschromatographischer Analyse ein einheitliches Produkt darstellt (Reinheit > 98 %).

Reference： [1]Patent: EP1391448,2004,A1 .Location in patent: Page 6

14
[ 21436-03-3 ]
[ 630-19-3 ]
N,N'-bis-(2,2-dimethylpropylidene)-cyclohexane-1,2-diamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With sodium sulfate; In dichloromethane; at 20℃; for 0.5h;	Example 2Diels-Alder reaction of 5-oxatricyclo1.2.1.03'71 dodeca-3,6-dien-12-one[Cu((S,SHm-Bu-box)]Cl2-CH2Cl2 (0.43 g, 0.83 mmol), silver hexafluoroantimonate (0.56 g, 1.63 mmol) and dichloromethane (DCM) (15 mL) were mixed under a nitrogen atmosphere and stirred for 4 h in the dark.Solid 5-oxatricyclo[7.2.1.03'7]dodeca-3,6-dien-12-one (Example 1) (2.91 g, 16.5 mmol) and 3-acryloyloxazolidin-2-one (4.66 g, 33.0 mmol) were charged to an oven-dried flask. The flask was degassed, put under a nitrogen atmosphere and then DCM (25 mL) was added and the stirred reaction mixture was cooled to -78 C. The green catalyst solution, prepared above, was then filtered through a 0.45 um filter into the reaction mixture over ~15 min, washing the filter through with DCM (5 mL). The resulting batch was then left to stir at -78 C for 20 h. The reaction was quenched by addition of cone. NH4OH (5 mL) and allowed to warm to ambient temperature. The resulting biphasic mixture was diluted with water (50 mL) and then extracted with DCM (3 x 50 mL). The combined organic layers were washed with saturated brine (50 mL), dried (Na2SC«4) and then concentrated in vacuo. The semi-solid residue obtained was taken up in EtOAc (50 mL), then heptane (100 mL) was slowly added to the resulting stirred slurry. After aging for 2 h at rt, the solid was collected by filtration and washed with 3:1 heptane-EtOAc (20 mL). After drying under vacuum, the Diels-Alder adduct IV (R1 = R2 = H, Z = O) was isolated as an off-white solid (4.74 g, 90%, >99% ee): .H NMR (250 MHz, CD2C12) 5 4.99 (d, /= 4.5 Hz, 1 H), 4.73 (d, /= 4.5 Hz, 1 H), 4.39 (t, /= 8.0 Hz, 2 H), 4.05 (app dt, /= 8.7,4.3 Hz, 1 H), 3.99-3.82 (m, 2 H), 2.60-2.39 (m, 2 H), 2.37-2.02 (m, 5 H), 1.95 (dddd, /= 11.1, 8.8, 4.5,1.0 Hz, 1 H), 1.83-1.60 (m, 4 H); 13C NMR (63 MHz, CD2C12) 5 222.4,171.3, 154.0,141.7,135.7, 85.1, 84.9, 62.9,45.6,45.5,45.4,43.3, 31.8, 30.2, 29.2, 26.9, 26.3.Alternative Procedure(+)-l,2-rraftS'-Diaminocyclohexane (250 mg, 2.18 mmol) in CH2C12 (20 mL) was treated with Na2SC«4 (923 mg, 6.50 mmol) and trimethylacetaldehyde (473 \|aL, 4.35 mmol). The mixture was stirred at ambient temperature under an atmosphere of N2 for 0.5 h then filtered. The filter was washed with CH2C12 (5 mL) and thecombined organics were evaporated to give N,N'-bis-(2,2-dimethylpropylidene)-cyclohexane-1,2-diamine (610 mg, 98%) as an off-white semi solid..H NMR (400 MHz, CD2C12) 5 7.45 (s, 2 H), 3.07 (m, 2 H), 1.74 (m, 2 H), 1.59 (m, 4 H), 1.37 (m, 2 H), 1.00 (s, 18 H): 13C NMR (100 MHz, CD2C12) 5 170.5, 73.7, 35.7, 33.2, 26.9, 24.5.N,N'-Bis-(2,2-dimethylpropylidene)-cyclohexane-l,2-diamine (78 mg, 0.312 mmol) and Cu(OTf)2 (103 mg, 0.284 mmol) were mixed at ambient temperature in anhydrous acetonitrile (1.5 mL) for 0.5 h under a nitrogen atmosphere. The resulting deep green solution was cooled to 0C and treated with a mixture of 5-oxatricyclo[7.2.1.03'7]dodeca-3,6-dien-12-one (500 mg, 2.84 mmol) and 3-acryloyloxazolidin-2-one (801 mg, 5.68 mmol) in acetonitrile (3 mL), added dropwise over 3 min. The resulting deep blue solution was aged at 0C for 2.5 h then treated with concentrated ammonium hydroxide and aged at 0C for 10 min. The mixture was diluted with CH2C12 (10 mL) and H20 (10 mL) and the layers were separated. The aqueous phase was extracted into CH2C12 (2x10 mL) and the combined organics were dried (Na2S04) and evaporated to dryness. LC analysis of the residue indicated an assay yield of 85%, endo:exo ratio of 20:1 and an endo ee of 86%. Isolation of the Diels-Alder adduct was then carried out as described previously.

Reference： [1]Patent: WO2006/18663,2006,A1 .Location in patent: Page/Page column 8-10

15
(S)-1-{(R)-2-(diphenylphosphino)ferrocenyl}ethyl acetate [ No CAS ]
[ 21436-03-3 ]
C₃₀H₃₅FeN₂P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With triethylamine; In water; isopropyl alcohol; toluene; at 50℃;	Ester S,R-10a (1.0 g; 2.19 mmol) was combined with S,S-1,2-diaminocyclohexane (500 mg; 4.38 mmol; 2 equiv) and triethylamine (0.92 mL; 6.57 mmol; 3 equiv) in 5 mL of isopropanol, 2 mL of water, and 1 mL of toluene. The reaction mixture was heated overnight at 50 C. to completely consume 10a according to tic analysis. The reaction mixture was diluted with ethyl acetate and 2 N sodium hydroxide (10 mL). The layers were separated and the aqueous layer was extracted twice with ethyl acetate. The combined organic solution was dried (magnesium sulfate) and concentrated to afford 1.58 g of crude product. This material was filtered through a pad of flash silica gel and eluted with 1:1 ethyl acetate:heptane to remove impurities, and then with 1:1 ethyl acetate:isopropanol with 5% added triethylamine to afford 0.84 g (75%) of S,S-11b. A portion of this phosphinodiamine (0.74 g; 1.45 mmol) was combined with ester S,R-10a (0.99 g; 2.17 mmol; 1.5 equiv) in 5 mL of isopropanol, 2 mL of water, and 1 mL of toluene. Triethylamine (0.40 mL; 2.9 mmol; 2.0 equiv) was added and the mixture was heated overnight at 50 C., at which point tlc analysis indicated no 11b residual according to tlc analysis. The reaction mixture was diluted with ethyl acetate and 1 N sodium hydroxide (20 mL). The layers were separated and the aqueous layer was extracted twice with ethyl acetate. The combined organic solution was dried (magnesium sulfate) and concentrated to afford 2.03 g of crude product. This material was filtered through a pad of flash silica gel and eluted with 1:4 ethyl acetate:heptane to remove impurities, and then with 1:1 ethyl acetate:heptane with 5% added triethylamine to afford 0.98 g (75%) of S,S-8b as a yellow foam. S,S-8b: 1H NMR (CDCl3) delta 7.6-7.1 (m, 20 H); 4.456 (br s, 2H); 4.228 (br s, 2H); 3.979 (s, 10H); 3.9 (m, 2H); 3.676 (br s, 2H); 1.69(br s, 2H); 1.6-0.4 (m, 14H).

Reference： [1]Patent: US2006/135804,2006,A1 .Location in patent: Page/Page column 7-8

16
[ 123-91-1 ]
[ 636-98-6 ]
[ 1003-56-1 ]
[ 21436-03-3 ]
(2R,4R)-4-Hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-[(4-chloro-phenyl)-amide]2-[(2'-hydroxy-biphenyl-4-yl)-amide] [ No CAS ]
[ 536748-56-8 ]

Yield	Reaction Conditions	Operation in experiment
36%	With potassium phosphate; CuI;	Step 1: 3-Methyl-1-(4-nitro-phenyl)-1H-pyridin-2-one (159-a) 1-Iodo-4-nitrobenzene (1.61 g, 6.45 mmol) was combined with 3-methyl-2-pyridone (0.845 g, 7.74 mmol), CuI (0.246 g, 1.29 mmol), and K3PO4 (2.74 g, 12.9 mmol). 1,4-Dioxane (6 mL) was added followed by trans-1,2-diaminocyclohexane (0.194 mL, 1.61 mmol). The mixture was heated to reflux for 19 h before cooling and diluting with EtOAc. The mixture was filtered through a plug of silica, eluding with EtOAc, and the filtrate concentrated under reduced pressure. Purification of the crude product by flash chromatography provided 159-a (0.528 g, 36%) as a brown solid. MS: APCI (AP+): 231.1 (M)+.

Reference： [1]Patent: US2003/162787,2003,A1

17
[ 21436-03-3 ]
[ 21286-54-4 ]
[ 609810-67-5 ]

Reference： [1]Patent: US2003/191345,2003,A1 .Location in patent: Page/Page column 4

18
[ 616-45-5 ]
[ 22445-41-6 ]
[ 21436-03-3 ]
1-(3,5-dimethylphenyl)-1H-pyrrolidin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With potassium phosphate; CuI; In 1,4-dioxane; dodecane;	Example 62 Preparation of N-(3,5-dimethylphenyl)-2-pyrrolidinone under air An oven-dried resealable Schlenk tube was charged with CuI (2.0 mg, 0.0105 mmol, 1.0 mol %) and K3PO4 (450 mg, 2.12 mmol) under air. trans-1,2-Cyclohexanediamine (13 muL, 0.108 mmol, 10 mol %), 5-iodo-m-xylene (150 muL, 1.04 mmol), 2-pyrrolidinone (94 muL, 1.24 mmol) and dioxane (1.0 mL) were added under air. The Schlenk tube was sealed and the reaction mixture was stirred magnetically at 110 C. for 23 h. The resulting brown suspension was cooled to room temperature, dodecane (235 muL, GC standard) was added, and the mixture was filtered through a Celite pad eluding with ethyl acetate. The GC analysis of the filtrate indicated a 95% yield of the product.

Reference： [1]Patent: US2003/65187,2003,A1

19
[ 1006-94-6 ]
[ 22445-41-6 ]
[ 21436-03-3 ]
[ 360045-08-5 ]

Yield	Reaction Conditions	Operation in experiment
100%	With potassium phosphate; CuI; In 1,4-dioxane;	Example 68 1-(3,5-Dimethylphenyl)-5-methoxyindole Using the general procedure outlined in Example 63, 5-methoxyindole (0.177 g, 1.20 mmol) was coupled with 5-iodo-m-xylene (144 muL, 1.00 mmol) using CuI (2.0 mg, 0.010 mmol, 1.0 mol %), K3PO4 (2.1 mmol), trans-1,2-cyclohexanediamine (12 muL, 0.10 mmol, 10 mol %) and dioxane (1.0 mL) to give the crude product. Column chromatography (2*15 cm, hexane:ethyl acetate 50:1) provided 0.250 g (100% yield) of the product as a white solid. 1H NMR (400 MHz, CDCl3): delta 7.66 (d, 1H, J=8.9 Hz), 7.43 (d, 1H, J=3.2 Hz), 7.32 (d, 1H, J=3.3 Hz,), 7.27 (bs, 2H), 7.12 (bs, 1H), 7.07 (dd, 1H, J=2.4 Hz and J=9.0 Hz), 6.75 (d, 1H, J=2.2 Hz,), 4.02 (s, 3H), 2.54 (s, 6H). 13C NMR (100 MHz, CDCl3): delta 154.33, 139.68, 139.20, 130.93, 129.71, 128.26, 127.78, 121.58, 112.20, 111.37, 102.80, 102.45, 55.58, 21.20.

Reference： [1]Patent: US2003/65187,2003,A1

20
[ 120-72-9 ]
[ 106-38-7 ]
[ 21436-03-3 ]
[ 167283-32-1 ]

Yield	Reaction Conditions	Operation in experiment
95%	With potassium phosphate; CuI; In 1,4-dioxane;	Example 65 1-(4-methylphenyl)-indole Using the general procedure outlined in Example 63, indole (0.117 g, 1.00 mmol) was coupled with 4-bromotoluene (185 muL, 1.50 mmol) using CuI (9.5 mg, 0.050 mmol, 5.0 mol %), K3PO4 (2.1 mmol), trans-1,2-cyclohexanediamine (24 muL, 0.20 mmol, 20 mol %) and dioxane (1.0 mL) to give the crude product. Column chromatography (2*15 cm, hexane:ethyl acetate 50:1) provided 0.197 g (95% yield) of the product as a white solid. This product was pure by 1H NMR when compared to the known spetra.

Reference： [1]Patent: US2003/65187,2003,A1

21
[ 112-62-9 ]
[ 21436-03-3 ]
trans-2-(Oleoylamino)cyclohexylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With sodium methylate; In ethyl acetate-water; benzene;	REFERENCE EXAMPLE 26 Preparation of trans-2-(Oleoylamino)cyclohexylamine Sodium methoxide (0.60 g) was added to a solution of 1.14 g of trans-1,2-diaminocyclohexane and 2.96 g of methyl oleate in 15 ml of benzene, and the mixture was heated under reflux for 20 hours. After completion of the reaction, the solvent was distilled off under reduced pressure and the residue was dissolved in ethyl acetate-water. The organic layer was washed with saturated saline, and dried over anhydrous sodium sulfate. After drying it over anhydrous sodium sulfate, the residue obtained was purified by silica gel column chromatography to obtain 2.54 g of the objective compound (yield: 68%). Property: Oily. Mass Spectrometric Analysis: Molecular formula: C24 H46 N2 O, Calculated: 378.3610, Found: 378.3611. NMR(delta, CDCl3): 0.88 (3H,t,J=7Hz), 1.12-1.48 (24H,m), 1.53-1.79 (4H,m), 1.91 (6H,m), 2.18-2.35 (2H,m), 2.52-2.95 (3H,m), 3.62-3.78 (1H,m), 5.28-5.40 (2H,m), 6.08-6.20 (1H,m).
68%	With sodium methylate; In ethyl acetate-water; benzene;	Reference Example 26 Preparation of trans-2-(Oleoylamino)cyclohexylamine Sodium methoxide (0.60 g) was added to a solution of 1.14 g of trans-1,2-diaminocyclohexane and 2.96 g of methyl oleate in 15 ml of benzene, and the mixture was heated under reflux for 20 hours. After completion of the reaction, the solvent was distilled off under reduced pressure and the residue was dissolved in ethyl acetate-water. The organic layer was washed with saturated saline, and dried over anhydrous sodium sulfate. After drying it over anhydrous sodium sulfate, the residue obtained was purified by silica gel column chromatography to obtain 2.54 g of the objective compound (yield: 68%). Property: Oily Mass Spectrometric Analysis: Molecular formula: C24H46N2O Calculated: 378.3610 Found: 378.3611 NMR(delta, CDCl3): 0.88 (3H,t,J=7Hz), 1.12-1.48 (24H,m), 1.53-1.79 (4H,m), 1.91 (6H,m), 2.18-2.35 (2H,m), 2.52-2.95 (3H,m), 3.62-3.78 (1H,m), 5.28-5.40 (2H,m), 6.08-6.20 (1H,m)
65%		REFERENCE EXAMPLE 27 Preparation of (S,S)-2-(Oleoylamino)cyclohexylamine (S,S)-1,2-Diaminocyclohexane (1.14 g) and 2.96 g of methyl oleate were reacted in the same manner as in Reference Example 26 to obtain 2.41 g of the objective compound (yield: 65%) Property: Oily. Mass Spectrometric Analysis: Molecular formula: C24 H46 N2 O, Calculated: 378.3610, Found: 378.3612. NMR(delta, CDCl3): 0.88 (3H,t,J=7Hz), 1.12-1.48 (24H,m), 1.53-1.79 (4H,m), 1.91 (6H,m), 2.18-2.35 (2H,m), 2.52-2.95 (3H,m), 3.62-3.78 (1H,m), 5.28-5.40 (2H,m), 6.08-6.20 (1H,m).

65%

Reference Example 27 Preparation of (S,S)-2-(Oleoylamino)cyclohexylamine (S,S)-1,2-Diaminocyclohexane (1.14 g) and 2.96 g of methyl oleate were reacted in the same manner as in Reference Example 26 to obtain 2.41 g of the objective compound (yield: 65%) Property: Oily Mass Spectrometric Analysis: Molecular formula: C24H46N2O Calculated: 378.3610 Found: 378.3612 NMR(delta, CDCl3): 0.88 (3H,t,J=7Hz), 1.12-1.48 (24H,m), 1.53-1.79 (4H,m), 1.91 (6H,m), 2.18-2.35 (2H,m), 2.52-2.95 (3H,m), 3.62-3.78 (1H,m), 5.28-5.40 (2H,m), 6.08-6.20 (1H,m)

Reference： [1]Patent: US5120738,1992,A
[2]Patent: EP421441,1991,A2
[3]Patent: US5120738,1992,A
[4]Patent: EP421441,1991,A2

22
[ 21436-03-3 ]
[ 180683-64-1 ]

Yield	Reaction Conditions	Operation in experiment
		[Referential Example 39] (+-)-trans-N-tert-Butoxycarbonyl-1,2-cyclohexanediamine: The title compound was obtained from (+-)-trans-1,2-cyclohexanediamine in a similar manner to Referential Example 34. mp 79-81C. 1H-NMR (CDCl3) delta: 1.05-1.34(4H,m), 1.45(9H,s), 1.68-1.75(2H,m), 1.92-2.02(2H,m), 2.32(1H,dt,J=10.3,3.9Hz), 3.08-3.20(1H,m), 4.50(1H,br.s). MS (FAB) m/z: 215(M+H)+.

Reference： [1]Patent: EP1270557,2003,A1

23
[ 37942-07-7 ]
[ 21436-03-3 ]
[ 151380-44-8 ]

Yield	Reaction Conditions	Operation in experiment
97%	In ethanol; for 2h;Reflux;	Added to the reaction vial (s, s)-cyclohexyl diamine 22.96g (0.2mol), anhydrous ethanol 1000 ml, stirring to dissolve. compound I 94.35g (0.4mol) is added to the reaction solution. The reaction is then heated to reflow the reaction liquid, the reaction time is about 2 hours. After the reaction, cooling to room temperature. Adding water to the reaction in the fluid drops 500 ml, stirring. Filtering, with a small amount of 95% ethanol 25 ml washing, filtering and drying. Get compound II 106g, yield 97% ;
	Heating / reflux;	Chiral ligands were prepared by refluxing 1 ,2-cyclohexyldiamines {R,R and S1S) with 2,4 di-.erf-butyl salicylaldehyde
	In ethanol; at 80℃; for 12h;	1.14g (S, S) -1,2 cyclohexanediamine was dissolved in 20mL ethanol to obtain (S, S) -1,2 cyclohexanediamine solution;4.7g of 3,5-di-tert-butyl salicylaldehyde was dissolved in 30mL of ethanol to give 3,5-di-tert-butyl salicylaldehyde solution, the 3,5-di-tert-butyl salicylaldehyde solution was slowly added dropwise to a solution of (S , S) -1,2 cyclohexanediamine solution, and the resulting mixed solution was refluxed at 80 C for 12 h to obtain a reaction mixture. The solvent in the reaction mixture was removed by filtration, and the resulting reaction product was recrystallized from ethanol to obtain a Schiff base ligand. Elemental analysis of the obtained Schiff base compound gives the content of each atom therein, with the following results: Elem. Anal. (%): Calcd. C 79.07, H 9.95, N 5.12; Found: C 78.71, H 9.85, N 4.77.

In ethanol; for 1h;Reflux; Inert atmosphere;

Derivative of Salisaldehyde (2 equiv.) as solid was added inportions to absolute ethanol solution of diamine derivative.The reaction mixture was heated to reflux for an hour undernitrogen atmosphere and then cooled to room temperature.17The yellow colored product was then collected by filtrationwashed with cold ethanol and dried under vacuum. 2.2a N,N-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanedi-amine: 1H NMR (500 MHz, CDCl3) delta 13.70 (s,2H), 8.29 (s, 2H), 7.30 (d, J = 2.5 Hz, 2H), 6.98 (d, J =2.5 Hz, 2H), 5.04-4.91 (m, 2H), 3.35-3.29 (m, 2H), 1.94 (d,J = 14.5 Hz, 2H), 1.90-1.84 (m, 2H), 1.73 (d, J = 11.0 Hz,2H), 1.50-1.45 (m, 2H), 1.41 (s, 18H), 1.23 (s, 18H).13CNMR(101 MHz, CDCl3) delta 166.0, 158.2, 140.0, 136.5, 126.9, 126.2,118.0, 72.6, 35.1, 34.2, 33.4, 31.6, 29.6, 24.5.

Reference： [1]Patent: CN105712889,2016,A .Location in patent: Paragraph 0059; 0060; 0061
[2]Patent: WO2007/93765,2007,A1 .Location in patent: Page/Page column 15
[3]Catalysis Letters,2010,vol. 140,p. 189 - 196
[4]Inorganic Chemistry Communications,2014,vol. 40,p. 47 - 50
[5]Organic Letters,2017,vol. 19,p. 448 - 451
[6]Patent: CN107417739,2017,A .Location in patent: Paragraph 0093-0095
[7]Journal of Chemical Sciences,2018,vol. 130
[8]Advanced Synthesis and Catalysis,2019,vol. 361,p. 1673 - 1677
[9]Organometallics,2020,vol. 39,p. 2642 - 2652

24
[ 21436-03-3 ]
[ 317595-54-3 ]

Yield	Reaction Conditions	Operation in experiment
		REFERENTIAL EXAMPLE 64 tert-Butyl (1R,2R)-2-aminocyclohexylcarbamate: The title compound was obtained from (+-)-trans-1,2-cyclohexanediamine in a similar manner to Referential Example 61. m.p.79-81. 1H-NMR (CDCl3) delta: 1.05-1.34(4H,m), 1.45(9H,s), 1.68-1.75(2H,m), 1.92-2.02(2H,m), 2.32(1H,dt,J=10.3, 3.9 Hz), 3.08-3.20(1H,m), 4.50(1H,br.s). MS (FAB) m/z: 215(M+H)+.

Reference： [1]Patent: US2005/20645,2005,A1

25
[ 58632-95-4 ]
[ 21436-03-3 ]
[ 180683-64-1 ]

Reference： [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 721 - 724

26
[ 110-52-1 ]
[ 21436-03-3 ]
[ 280566-45-2 ]
[ 939818-88-9 ]

Yield	Reaction Conditions	Operation in experiment
		Diisopropylethylamine and (1S,2S)-1,2-cyclohexandiamine were added to <strong>[280566-45-2]2-chloro-6-(trifluoromethyl)nicotinic acid</strong>, followed by stirring at 100C for 30 minutes and at 140C for 10 minutes using a microwave reaction device. The reaction liquid was dissolved in acetonitrile, potassium carbonate and 1,4-dibromobutane were added, followed by stirring at 50C for 8 hours. By dissolving the residue extracted with chloroform in methanol and THF, adding 1 M sodium hydroxide aqueous solution thereto and carrying out the reaction at 50C, 2-[(1S,2S)-2-pyrrolidin-1-ylcyclohexyl]amino}-6-(trifluoromethyl)nicotinic acid was obtained.

Reference： [1]Patent: EP1955697,2008,A1 .Location in patent: Page/Page column 19

27
[ 21436-03-3 ]
[ 280566-45-2 ]
C₁₃H₁₆F₃N₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; at 150℃; for 0.5h;microwave irradiation;	2-Chloro-6-(trifluoromethyl)nicotinic acid, (1S,2S)-1,2-cyclohexandiamine and diisopropylethylamine were mixed, followed by stirring at 150C for 30 minutes under microwave irradiation. After spontaneous cooling, the reaction liquid was concentrated under a reduced pressure, the residue was dissolved in methanol and sulfuric acid was added thereto. After 6 days of stirring under heat reflux, this was spontaneously cooled and concentrated under a reduced pressure. This was neutralized with saturated sodium bicarbonate aqueous solution and then extracted with chloroform. After concentration of the organic layer under a reduced pressure, the resulting residue was dissolved in THF, and sodium triacetoxyborohydride and a formaldehyde aqueous solution (36%) were added thereto in that order. By post-treating the reaction liquid, methyl 2-[(1S,2S)-2-(dimethylamino)cyclohexyl]amino}-6-(trifluoromethyl)nicotinate was obtained.

Reference： [1]Patent: EP1955697,2008,A1 .Location in patent: Page/Page column 21

28
[ 19715-19-6 ]
[ 21436-03-3 ]
N-[(1R,2R)-2-aminocyclohexane]-3,5-di-tert-butyl-2-hydroxybenzamide [ No CAS ]

Reference： [1]Tetrahedron Letters,2008,vol. 49,p. 4796 - 4798

29
[ 21436-03-3 ]
[ 123843-67-4 ]
[ 1073973-72-4 ]

Yield	Reaction Conditions	Operation in experiment
90%	With N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; at 80℃; for 16h;	4-Bromo-2,6-difluoro-benzonitrile (3 g, 13.8 mmol), (1S,2S)-2-hydroxycyclohexylamine (1.9 g, 16.5 mmol) and diisopropylethylamine base (3.56 g, 27.5 mmol) are dissolved in DMSO (10 mL) and heated to 80 C. for 16 h. The mixture is partitioned between EtOAc (100 mL) and 1 N HCl (50 mL). The organic layer is washed with brine (25 mL), dried over MgSO4, filtered and concentrated to a glass. The glass is dissolved in toluene, added to a column and purified via chromatography (silica, 20 to 70% EtOAc in hexanes) to give 4-bromo-2-fluoro-6-((1S,2S)-2-hydroxycyclohexylamino)benzonitrile (3.9 g, 90%) as a fluffy tan solid.

Reference： [1]Patent: US2008/269193,2008,A1 .Location in patent: Page/Page column 59

30
[ 14562-10-8 ]
[ 21436-03-3 ]
C₃₂H₃₀N₂O₂ [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2008,p. 3369 - 3376

31
[ 21436-03-3 ]
[ 191480-65-6 ]

Yield	Reaction Conditions	Operation in experiment
95%	With hydrogenchloride; In diethyl ether;	(S)- and (R)- 3,3'-diformyl-l,l '-bi-2-napthol, (IR,2R)- and (ISJS)- 2- (3 ,5 -di-tert-butyl-2-hydroxybenzylideneamino)cyclohexanammonium chloride, and bis(triphenyl-phosphine)iminium acetate ([PPN][OAc]) were prepared according to literature procedure.

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 4056 - 4060
Angew. Chem.,2017,vol. 129,p. 4115 - 4119,5
[2]Chemistry - A European Journal,2019,vol. 25,p. 1515 - 1524
[3]Patent: WO2009/26261,2009,A2 .Location in patent: Page/Page column 63; 64

32
[ 1005785-88-5 ]
[ 1801-10-1 ]
[ 21436-03-3 ]
[ 7681-65-4 ]
[ 1005785-89-6 ]

Yield	Reaction Conditions	Operation in experiment
42%	With potassium carbonate; In 1,4-dioxane; hexane;	Example 332 Production of N-[5-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-b]pyridazin-6-yl}oxy)pyridin-3-yl]-<strong>[1801-10-1]3-(trifluoromethyl)benzamide</strong> To a solution of N-{6-[(5-bromopyridin-3-yl)oxy]imidazo[1,2-b]pyridazin-2-yl}cyclopropanecarboxamide (200 mg, 0.53 mmol), <strong>[1801-10-1]3-(trifluoromethyl)benzamide</strong> (160 mg, 0.91 mmol), trans-1,2-diaminocyclohexane (15 mg, 0.13 mmol) and potassium carbonate (220 mg, 1.6 mmol) in 1,4-dioxane (3.0 mL) was added copper (I) iodide (25 mg, 0.13 mmol) under argon atmosphere, and the mixture was stirred at 110 C. for 60 hr. The reaction mixture was cooled, and diluted with 20% tetrahydrofuran/ethyl acetate. The mixture was washed with water, 5% aqueous sodium hydrogencarbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and filtrated. The solvent was evaporated under reduced pressure, and the residue was purified by NH silica gel column chromatography (ethyl acetate/hexane=60/40?100/0) and precipitated from ethyl acetate/hexane to give the title compound (110 mg, 42%) as a white powder. 1H-NMR (DMSO-d6, 300 MHz) delta 0.72-0.86 (4H, m), 1.84-1.98 (1H, m), 7.17 (1H, d, J=9.6 Hz), 7.81 (1H, t, J=7.8 Hz), 7.96-8.04 (2H, m), 8.10 (1H, d, J=9.6 Hz), 8.20 (1H, t, J=2.4 Hz), 8.23-8.35 (2H, m), 8.38 (1H, d, J=2.4 Hz), 8.85 (1H, d, J=2.4 Hz), 10.83 (1H, s), 11.10 (1H, s).

Reference： [1]Patent: US2009/137595,2009,A1

33
[ 3328-69-6 ]
[ 21436-03-3 ]
C₄₂H₄₈N₆O₃ [ No CAS ]

Reference： [1]Tetrahedron Letters,2010,vol. 51,p. 449 - 452

34
[ 21436-03-3 ]
[ 100-52-7 ]
(1S,2S)-N1,N2-dibenzylcyclohexane-1,2-diamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%		To a solution of (1 S,2S)-cyclohexane-1 ,2-diamine (1.14 g, 10.0 mmol) in dry methanol was added benzaldehyde (2.03 ml_, 20.0 mmol, 2 equiv). The solution was refluxed for 4 h and then cooled via an ice bath. Addition of NaBH4 (1.62 g, 43.0 mmol, 4.3 equiv) was performed slowly and in small portions to prevent boiling, and the reaction mixture was stirred for 12 h until completion. The solvent was evaporated in vacuo, and then saturated NaHC03 (50 mL), water (50 mL) and dichloromethane (200 mL) were added. The aqueous layer was extracted twice more with dichloromethane (100 mL). The combined organic layers were dried over MgS04, filtered, and concentrated in vacuo to afford a waxy, yellow solid. Product was purified by silica column chromatography to afford 7 as yellow oil. Yield 69%. 1H NMR (500 MHz, CDCI3 ):delta ppm 7.29-7.40 (m, 8H), 7.23-7.29 (m, 2H), 3.92 (d, J= 10.0 Hz, 2H), 3.69 (d, J= 10.0 Hz, 2H), 2.28-2.35 (m, 2H), 2.14-2.26 (m, 4H), 1.76 (m, 2H), 1.21-1.33 (m, 2H), 1.03-1.14 (m, 2H), 13C NMR (126 MHz, CDCI3): delta ppm 141.15, 128.40, 128.15, 126.84, 60.92, 50.92, 31.58, 25.18. ESIMS (m/z) 295 [M+H]+, 317 [M+Na]+, 293 [M-H]-
		Benzaldehyde (6.36 g, 60 mmol) was added dropwise over a period of 2 minutes to a solution of (S,S)-cyclohexane-1,2-diamine (3.42 g, 30 mmol) in 50 mL of anhydrous MeOH at refluxing temperature. After stirring for 30 min, the solution was allowed to cool to room temperature and NaBH3CN (2.4 g, 63 mmol) was added in portions. After the vigorous effervescence subsided down, the mixture was brought to refluxing and stirred for 20 min. The reaction was quenched by water and extracted with dichloromethane. The organic phase was dried and concentrated to give 8.5 g of crude product (yield 95%) which was used in the next step reaction without further purification.

Reference： [1]Patent: WO2018/48879,2018,A1 .Location in patent: Paragraph 0160
[2]Patent: US2010/216806,2010,A1 .Location in patent: Page/Page column 108-109
[3]Journal of Medicinal Chemistry,2012,vol. 55,p. 8903 - 8925,23
[4]Journal of the Chemical Society of Pakistan,2014,vol. 36,p. 85 - 90
[5]Bioconjugate Chemistry,2016,vol. 27,p. 2540 - 2548

35
[ 1342297-62-4 ]
[ 21436-03-3 ]
[ 1342297-63-5 ]

Yield	Reaction Conditions	Operation in experiment
90%	In tetrahydrofuran; at 20℃; for 3h;	A solution of dialdehyde 26 (2 mmol, 2 equiv) in THF (1.2 mL) was added to a solution of (1S,2S)-(+)-1,2-diaminocyclohexane27 (2 mmol, 2 equiv) in THF (0.8 mL) and the resulting mass was stirred for 3 h at room temperature (checked on TLC). After the completion of the reaction, the solvent was completely removed under reduced pressure on a rotary evaporator to give chiral macrocyclic salen ligand 28 in high yield, which was used as such for the preparation of the complex 1 without further purification.

Reference： [1]Tetrahedron,2011,vol. 67,p. 8300 - 8307
[2]Chirality,2012,vol. 24,p. 1063 - 1073

36
[ 21436-03-3 ]
[ 84501-28-0 ]
C₅₄H₇₂N₆O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	In methanol; acetonitrile; at 20℃; for 24h;	To a solution of (S,S)-(+)-1,2-diaminocyclohexane (0.39 g, 3.4 mmol) in CH3CN (160 ml) was added a solution of <strong>[84501-28-0]2,6-diformyl-4-tert-butylphenol</strong> (0.64 g, 3.1 mmol) in MeOH (60 ml). The mixture was stirred at room temperature for 24 h. The Schiff-base macrocycle separated as a yellow solid, was filtered, and recrystallized from CH2Cl2-CH3CN. (S,S,S,S,S,S)-1d: yellow prisms, mp >300 C. Yield 0.52 g (59%). [alpha]D = +193 (c 0.1, CH2Cl2). IR: 3255, 3182 cm-1 (OH), 1637 cm-1 (CN). 1H NMR (CDCl3) delta 13.92 (s, OH), 8.67 (s, HCN), 8.24 (s, HCN), 7.83 (s, Ar), 7.12 (s, Ar), 3.31-3.41 (m, N-CH), 1.46-1.83 (m, -CH2-), 1.19(s, t-Bu). 13C NMR (CDCl3) delta 24.4, 31.3, 33.2, 33.8, 73.0, 75.7, 118.5, 122.9, 126.2, 130.6, 140.1, 156.1, 159.6, 164.1. MS (ESI) m/z: 853.74[M+H]+, found 859.84[M+Li]+, calcd 859.58.

Reference： [1]Chemical Communications,2012,vol. 48,p. 2237 - 2239
[2]Tetrahedron Asymmetry,2012,vol. 23,p. 205 - 208

37
[ 3163-76-6 ]
[ 21436-03-3 ]
CC₃-S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With trifluoroacetic acid; In dichloromethane; at 20℃;	CC3-R (and CC3-S) were synthesised as reported previously.1 In a 250 mL round bottom flask, dichloromethane (DCM, 100 mL) was added slowly onto solid 1,3,5-triformylbenzene (5.0 g, 30.86 mmol) at room temperature without stirring to avoid mixing and hence to prevent rapid dissolution of the aldehyde. Trifluoroacetic acid (100 muL) was added directly to this solution as a catalyst for imine bond formation. Next, a solution of (R, R)-1,2-diaminocyclohexane (5.0 g, 44.64 mmol) in dichloromethane (100 mL) was slowly layered onto this solution, again being careful to avoid mixing. The unmixed reaction was then covered and left to stand at room temperature. The white, crystalline product was removed by filtration and washed with 95% ethanol/5% dichloromethane. Isolated yield: 6.5 g, 83%.

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 588 - 598
[2]Patent: US2017/128910,2017,A1 .Location in patent: Paragraph 0050
[3]Angewandte Chemie - International Edition,2018,vol. 57,p. 11228 - 11232
Angew. Chem.,2018,vol. 130,p. 11398 - 11402,5

38
[ 1333327-40-4 ]
[ 21436-03-3 ]
C₃₆H₅₂N₂O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	In methanol; at 0 - 20℃; for 12h;	In a single-necked 50 mL round-bottom flask bis-aldehyde c (0.72 g, 1.5 mmol) was taken in dry MeOH (10 mL) and was stirred at 0 C, and a solution of 1S,2S-(+)-1,2-diaminocyclohexane (0.18 g,1.6 mmol)/1S, 2S-(-)-1,2-diphenylethane-1,2-diamine (0.34 g,1.6 mmol) in dry MeOH (5 mL) was added drop wise to the above solution. After complete addition, the resulting solution was further stirred at room temperature. After an interval of 12 h, solvent was completely removed under reduced pressure, and the bright yellow solid was extracted with dichloromethane (50 mL). The organic layer was washed with water (3 × 50 mL) and with brine (3 × 50 mL) and finally dried over anhydrous Na2SO4. After removal of dichloromethane under reduced pressure, the chiral ligands 1' and 2' purified by silica gel column chromatography (100-200 mesh) in 20% (EtOAc: Hexane) resulted in yellowish solid monomeric macrocyclic ligands, 1' and 2'.1': Yield 85%. m.p. 104 C. 1H NMR (500 MHz, CDCl3): delta 1.44 (18 H, s), 1.73-1.91 (8H, m), 3.23-3.25 (2H, m), 3.31-3.33 (4H, m), 3.51-3.62 (8H, m), 4.19 (2H, d, J = 11), 4.43 (2H, d, J = 11), 6.72 (2H, s), 7.27 (2H, s), 8.07 (2H, s), 11.78 (2H, br) ppm. 13C NMR (125 MHz, CDCl3): 24.3, 29.4, 32.7, 34.8, 68.5, 69.2, 70.7, 72.3, 76.4, 118.3, 127.3, 129.8, 137.4, 160.0, 166.2 ppm. FT-IR (KBr): nu 3432, 2942, 2863, 2359, 1629, 1558, 1442, 1387, 1259, 1212, 1099, 970, 845, 768, 728, 668, 594 cm-1. (c = 0.052, CH2Cl2). Anal. Calcd. for C36H52N2O6: C, 71.02; H, 8.61; N, 4.60. Found C, 71.0; H, 8.58; N, 4.58. TOF-MS (ESI+): m/z Calcd. for [C36H52N2O6] 608.81, Found 610.2 [M+H].

Reference： [1]Journal of Catalysis,2012,vol. 286,p. 41 - 50

39
[ 1333327-40-4 ]
[ 21436-03-3 ]
C₇₂H₁₀₄N₄O₁₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	In tetrahydrofuran; at 20℃; for 2h;	Bis-aldehyde c (0.53 g,1.1 mmol) in dry THF (1.2 mL) was taken in a single-necked 50 mL round-bottom flask to which the solution of 1S,2S-(+)-1,2-diaminocyclohexane (0.14 g,1.2 mmol)/1S,2S-(-)-1,2-diphenylethane-1,2-diamine (0.27 g, 1.2 mmol) in dry THF (0.6 mL) was added slowly and the resultant solutions were stirred at room temperature. After completion of the reaction (2 h) checked on TLC, the solvent was removed completely under reduced pressure. The bright yellow solids were extracted with dichloromethane (50 mL), and the organic layer was washed with water (3 × 50 mL), brine (3 × 50 mL) and finally dried over anhydrous Na2SO4. After removal of dichloromethane under reduced pressure, the chiral dimeric macrocyclic ligands 3' and 4' were purified by silica gel chromatography (100-200 mesh) with a EtOAc-to-Hexane of 3:2.3': Yield 96%. m.p. 76 C. 1H NMR (500 MHz, CDCl3): delta 1.38 (36H, s),1.67-1.93 (16H, m), 3.32 (4H, m), 3.55 (8H, t, J = 5), 3.61 (16H, t, J = 7), 4.37 (8H, s), 6.97 (4H, s), 7.20 (4H, s), 8.26 (4H, s), 13.86 (4H, br) ppm. 13C NMR (125 MHz, CDCl3): 25.0, 31.0, 34.7, 70.7, 72.2, 74.0, 74.8, 79.0, 119.8, 128.7, 131.2, 138.8, 161.6, 167.0 ppm; FT-IR (KBr): nu 3424, 2934, 2863, 2361, 1628, 1537, 1446, 1384, 1317, 1239, 1098, 940, 868, 785, 671, 563, 420 cm-1. (c = 0.052, CH2Cl2). Anal. Calcd. for C72H104N4O12 C, 71.02; H, 8.61; N, 4.60. Found C, 71.05; H, 8.63; N, 4.62. MALDI-TOF: m/z Calcd. for [C72H104N4O12] 1217.62, Found 1218.19 [M+H].

Reference： [1]Journal of Catalysis,2012,vol. 286,p. 41 - 50

40
[ 21436-03-3 ]
[ 100-52-7 ]
[ 207450-11-1 ]

Yield	Reaction Conditions	Operation in experiment
48%		Benzaldehyde (3.05 mL, 30.0 mmol) was added to a methanol (300 mL) solution of (lS,2S)-cyclohexane-l,2-diamine (3.43 g, 30.0 mmol) with stirring at room temperature, and the mixture was stirred overnight at the same temperature. The reaction mixture was cooled to 0C. Sodium borohydride (2.27 g, 60.0 mmol) was added thereto, and the mixture was stirred at 0C for 2 hours. To the reaction mixture, water (30 mL) was added, and the product was extracted twice with methylene chloride (50 mL). The organic layers were combined and dried over magnesium sulfate, and the solvent was then distilled off under reduced pressure. The obtained residue was purified by basic silica gel column chromatography (ethyl acetate/hexane) to obtain (lS,2S)-N-benzylcyclohexane-l,2-diamine (cas no. 207450-11-1) (2.95 g, yield: 48%) in a pale yellow oil form.
48%		Reference Example 36 Production of (4aS,8aS)-l-benzyldecahydroquinoxaline Benzaldehyde (3.05 mL, 30.0 mmol) was added to a methanol (300 mL) solution of (lS,2S)-cyclohexane-l,2-diamine (3.43 g, 30.0 mmol) with stirring at room temperature, and the mixture was stirred overnight at the same temperature. The reaction mixture was cooled to 0C. Sodium borohydride (2.27 g, 60.0 mmol) was added thereto, and the mixture was stirred at 0C for 2 hours. To the reaction mixture, water (30 mL) was added, and the product was extracted twice with methylene chloride (50 mL). The organic layers were combined and dried over magnesium sulfate, and the solvent was then distilled off under reduced pressure. The obtained residue was purified by basic silica gel column chromatography (ethyl acetate/hexane) to obtain (lS,2S)-N-benzylcyclohexane-l,2-diamine (cas no. 207450-11-1) (2.95 g, yield: 48%) in a pale yellow oil form.

Reference： [1]Patent: WO2012/36253,2012,A1 .Location in patent: Page/Page column 59
[2]Patent: WO2013/137479,2013,A1 .Location in patent: Paragraph 0231

41
[ 21436-03-3 ]
[ 1197-13-3 ]
C₂₀H₂₄N₄O₄ [ No CAS ]

Reference： [1]Journal of Fluorescence,2011,vol. 21,p. 701 - 705

42
[ 406928-04-9 ]
[ 21436-03-3 ]
C₅₁H₆₆N₆O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	In methanol; acetonitrile; at 20℃; for 24h;	To a solution of (S,S)-(+)-1,2-diaminocyclohexane (0.41 g, 3.6 mmol) in CH3CN (160 ml) was added a solution of 2,6-diformyl-4-isopropylphenol (0.64 g, 3.3 mmol) in MeOH (60 ml). The mixture was stirred at room temperature for 24 h. The Schiff-base macrocycle separated as a yellow solid, was filtered, and recrystallized from CH2Cl2-CH3CN. (S,S,S,S,S,S)-1c: yellow prisms, mp 228-232 C. Yield 0.75 g (84%). [alpha]D = +225 (c 0.1, CH2Cl2). IR: 3180 cm-1 (OH), 1637 cm-1 (CN). 1H NMR (CDCl3) delta 13.91 (s, OH), 8.67 (s, HCN), 8.24 (s, HCN), 7.65 (s, Ar), 6.99 (s, Ar), 3.30-3.42 (m, N-CH), 2.72-2.79 (m, CH), 1.46-1.83 (m, -CH2-), 1.11(d, J = 8 Hz, CH3). 13C NMR (CDCl3) delta 23.9, 24.1, 24.3, 24.4, 73.1, 75.5, 118.9, 123.1, 127.5, 131.1, 138.0, 156.3, 159.7, 163.7. MS (ESI) m/z: found 811.74[M+H]+, calcd 811.53.

Reference： [1]Tetrahedron Asymmetry,2012,vol. 23,p. 205 - 208

43
[ 109517-99-9 ]
[ 21436-03-3 ]
C₄₂H₄₅Br₃N₆O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	In methanol; acetonitrile; at 20℃; for 24h;	To a solution of (S,S)-(+)-1,2-diaminocyclohexane (0.38 g, 3.3 mmol) in CH3CN (160 ml) was added a solution of 2,6-diformyl-4-bromophenol (0.69 g, 3.0 mmol) in MeOH (60 ml). The mixture was stirred at room temperature for 24 h. The Schiff-base macrocycle separated as a yellow solid, was filtered, and recrystallized from CH2Cl2-CH3CN. (S,S,S,S,S,S)-1f: yellow prisms, mp 228-232 C. Yield 0.79 g (86%). [alpha]D = +192 (c 0.1, CH2Cl2). IR: 3411 cm-1 (OH), 1637 cm-1 (CN). 1H NMR (CDCl3) delta 14.14 (s, OH), 8.58 (s, HCN), 8.18 (s, HCN), 7.88 (s, Ar), 7.24 (s, Ar), 3.27-3.49 (m, N-CH), 1.46-2.01 (m, -CH2-), 1.11(d, J = 8 Hz, CH3). 13C NMR (CDCl3) delta 24.4, 31.1, 33.7, 73.0, 75.7, 118.5, 122.8, 126.1, 130.6, 140.1, 156.1, 159.3, 164.0. MS (ESI) m/z: found 923.33[M+H]+, calcd 923.11.

Reference： [1]Tetrahedron Asymmetry,2012,vol. 23,p. 205 - 208

44
[ 73289-61-9 ]
[ 21436-03-3 ]
C₄₅H₅₄N₆O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	In methanol; acetonitrile; at 20℃; for 24h;	To a solution of (S,S)-(+)-1,2-diaminocyclohexane (0.45 g, 3.9 mmol) in CH3CN (160 ml) was added a solution of 2,6-diformyl-4-methoxyphenol (0.64 g, 3.6 mmol) in MeOH (60 ml). The mixture was stirred at room temperature for 24 h. The Schiff-base macrocycle separated as a yellow solid, was filtered, and recrystallized from CH2Cl2-CH3CN. (S,S,S,S,S,S)-1e: yellow prisms, mp 228-232 C. Yield 0.85 g (91%). [alpha]D = +250 (c 0.1, CH2Cl2). IR: 3167 cm-1 (OH), 1637 cm-1 (CN). 1H NMR (CDCl3) delta 13.52 (s, OH), 8.65 (s, HCN), 8.19 (s, HCN), 7.40 (s, Ar), 6.70 (s, Ar), 3.69 (s, OMe), 3.32-3.69 (m, N-CH), 1.46-1.84 (m, -CH2-). 13C NMR (CDCl3) delta 24.4, 33.2, 33.5, 56.0, 73.6, 75.4, 114.9, 118.7, 119.2, 123.8, 151.2, 155.6, 163.5. MS (ESI) m/z: found 775.43[M+H]+, calcd 775.42.

Reference： [1]Tetrahedron Asymmetry,2012,vol. 23,p. 205 - 208

45
[ 21436-03-3 ]
[ 98-59-9 ]
[ 174291-96-4 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 2378 - 2381

46
[ 1259012-01-5 ]
[ 21436-03-3 ]
[ 1259277-58-1 ]

Yield	Reaction Conditions	Operation in experiment
79%	In tetrahydrofuran; at 140℃; for 0.333333h;Sealed tube;	Formation of (1S,2S)-N1-(2-(5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-yl)cyclohexane-1,2-diamine (15b) (1924) 5-Chloro-3-(5-fluoro-4-methylsulfinyl-pyrimidin-2-yl)-1-(p-tolylsulfonyl)pyrrolo[2,3-b]pyridine, 15a, (0.25 g, 0.53 mmol) and (1S,2S)-cyclohexane-1,2-diamine (0.12 g, 1.08 mmol) were dissolved in THF (3.0 mL), and heated to 140 C. for 20 minutes in a sealed vial. The solvent was evaporated in vacuo and the residue was purified by silica gel chromatography (0%-15% MeOH/CH2Cl2) to provide product, 15b, as a white foamy solid (220 mg, 79% yield). (1925) 1H NMR (300 MHz, CDCl3) delta 8.85 (d, J=2.4 Hz, 1H), 8.52 (s, 1H), 8.40 (d, J=2.4 Hz, 1H), 8.13-8.09 (m, 3H), 7.31-7.28 (m, 2H), 5.14 (d, J=6.6 Hz, 1H), 3.96-3.85 (m, 1H), 2.69 (td, J=10.2, 4.7 Hz, 1H), 2.40 (s, 3H), 2.33 (d, J=5.6 Hz, 1H), 2.12-2.06 (m, 1H), 1.88-1.84 (m, 2H) and 1.60-1.21 (m, 4H) ppm; LCMS RT=2.33 (M+1) 515.2.
79%	In tetrahydrofuran; at 140℃; for 0.333333h;Sealed tube;	5-Chloro-3-(5-fluoro-4-methylsulfinyl-pyrimidin-2-yl)-1-(p-tolylsulfonyl)pyrrolo[2,3-b]pyridine, 15a, (0.25 g, 0.53 mmol) and (1S,2S)-cyclohexane-1,2-diamine (0.12 g, 1.08 mmol) were dissolved in THF (3.0 mL), and heated to 140 C. for 20 minutes in a sealed vial. The solvent was evaporated in vacuo and the residue was purified by silica gel chromatography (0%-15% MeOH/CH2Cl2) to provide product, 15b, as a white foamy solid (220 mg, 79% yield).
	In tetrahydrofuran;	Formation of (1S,2S)-N1-(2-(5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-yl)cyclohexane-1,2-diamine (15b) 5-Chloro-3-(5-fluoro-4-methylsulfinyl-pyrimidin-2-yl)-1-(p-tolylsulfonyl)pyrrolo[2,3-b]pyridine, 15a, (0.25 g, 0.53 mmol) and (1S,2S)-cyclohexane-1,2-diamine (0.12 g, 1.08 mmol) were dissolved in THF (3.0 mL), and heated to 140 C. for 20 minutes in a sealed vial. The solvent was evaporated in vacuo and the residue was purified by silica gel chromatography (0%-15% MeOH/CH2Cl2) to provide product, 15b, as a white foamy solid (220 mg, 79% yield).

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 6668 - 6678
[2]Patent: US9345708,2016,B2 .Location in patent: Page/Page column 282
[3]Patent: JP2015/38146,2015,A .Location in patent: Paragraph 0747
[4]Patent: US2012/171245,2012,A1

47
[ 4199-89-7 ]
copper(II) choride dihydrate [ No CAS ]
[ 21436-03-3 ]
potassium perchlorate [ No CAS ]
[copper(II)((1S,2S)-diaminocyclohexane)(5-chloro-1,10-phenanthroline)](perchlorate)2*0.25H₂O [ No CAS ]

Reference： [1]Dalton Transactions,2013,vol. 42,p. 3196 - 3209

48
copper(II) choride dihydrate [ No CAS ]
[ 100125-12-0 ]
[ 21436-03-3 ]
potassium perchlorate [ No CAS ]
[copper(II)((1S,2S)-diaminocyclohexane)(3,8-dibromo-1,10-phenanthroline)](perchlorate) monohydrate [ No CAS ]

Reference： [1]Dalton Transactions,2013,vol. 42,p. 3196 - 3209

49
[ 21436-03-3 ]
[ 122039-27-4 ]
(1S,2S)-cyclohexane-1,2-diaminium N,N'-(1S,2S)-cyclohexane-1,2-diylbis(P-phenylphosphonamidodiselenoate) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	In tetrahydrofuran; at 20℃; for 4h;Inert atmosphere;	A mixture of trans-1,2-cyclohexanediamine (0.228g, 2.0mmol) and WR (0.54g, 1.0mmol) in tetrahydrofuran (50mL) was stirred at room temperature for 4h. The red suspension disappeared and a bright yellow suspension formed. Upon filtration to remove unreacted solid the filtrate was dried in vacuo to give a golden solid (0.705g, 93% yield), mp 160-162C. Selected IR (KBr, cm-1): 2930(w), 2858(w), 1434(s), 1260(m), 1184(s), 1091(s), 1062(s), 888(m), 747(m), 692(s), 545(vs, P-Se). 1H NMR (THF-d8, delta), 8.31-7.97 (m, 4H, ArH), 7.38-7.25 (m, 6H, ArH), 6.21 (m, 6H, NH3), 4.32 (d, J(P,H)=13.5Hz, 2H, NH), 4.24-4.15 (m, 2H, CH), 3.64-3.58 (m, 2H, CH), 3.17-2.85 (m, 8H, CH2), 1.79-1.73 (m, 8H, CH2)ppm. 13C NMR (THF-d8, delta), 141.7 (d, J(P,C)=127.1Hz), 130.7 (d, J(P,C)=12.5Hz), 130.3 (d, J(P,C)=3.1Hz), 127.3 (d, J(P,C)=13.5Hz), 62.4 (d, J(P,C)=8.3Hz), 54.4, 31.3 (d, J(P,C)=13.5Hz), 30.5, 24.7, 24.1ppm. 31P NMR (THF-d8, delta), 124.6 (s, J(P,Se)=799Hz)ppm. 77Se NMR (THF-d8, delta), -178.2 (d, J(P,Se)=799Hz)ppm. MS (ES- m/z), 323 [1/2M]-. Accurate mass measurement [ES-, m/z]: 322.8965 [1/2M]-, calculated mass for [C18H22N2P2Se4]: 322.8969.

Reference： [1]Tetrahedron,2013,vol. 69,p. 5299 - 5305

50
trans-[RuCl₂(H₂C=C(CH₂PPh₂)₂)₂] [ No CAS ]
[ 21436-03-3 ]
trans-[Ru^(II)(H₂C=C(CH₂PPh₂)₂)(1,2-diaminocyclohexane)Cl₂] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	In dichloromethane; at 20℃; for 0.5h;Inert atmosphere; Schlenk technique;	General procedure: The corresponding diamine (10% excess, 0.55mmol) was dissolved in 10mL of dichloromethane and then added dropwise to a stirred solution of (0.50g, 0.50mmol) trans-[RuCl2(dppme)2] in 10mL of dichloromethane within 5min at room temperature. The mixture was stirred for 30min at room temperature while the color changed from brown to yellow. After the removal of unreacted materials, the volume of the solution was concentrated to about 5ml under reduced pressure. The product was precipitated by adding 40mL of diethyl ether and recrystallized from dichloromethane/n-hexane.

Reference： [1]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2014,vol. 117,p. 250 - 258

51
[ 21436-03-3 ]
[ 68282-47-3 ]
(1S,2S)-N,N'-bis[(2-phenyl-1H-imidazol-4-yl)methylidene]cyclohexane-1,2-diamine [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,2014,vol. 51,p. 695 - 701

52
[ 24424-99-5 ]
[ 21436-03-3 ]
bis-BOC-(S, S)-cyclohexane diamine [ No CAS ]
[ 180683-64-1 ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane; at 20℃; for 12h;Inert atmosphere;	To an ice cold solutionof (1S, 2S)-diaminocylohexane (570 mg, 5 mmol) in 3 ml ofdichloromethane was added a solution of di-t-butyldicarbonate (362.29 mg, 1.66 mmol) in dichloromethane over a period of 30 min. After complete addition of BOC anhydride, the reaction was allowed to stir for 12h at room temperature. The resultant precipitate was dissolved in 12 ml of water/ dichloromethane (1:1), after separation of two phases, the dichloromethane phase was concentrated under reduced pressure and the residue was dissolved in 12 ml of ether/water (1:1). The mixture was acidified to pH 5 using 4M hydrochloric acid solutions, and the bis-protected diamine was extracted with ether (3 X 50 ml). The combined ether extracts were washed thoroughly with water (2 X 100 ml) to take care of possible monoprotected diamine. Theether layer was then dried over anhydrous sodium sulphate and was concentrated under reduced pressure to yield bisprotected diamine. The aqueous phase was adjusted to pH 10 using 2M sodium hydroxide solution and was extracted with ethyl acetate (3 X 100 ml) and the combined organic extracts were driedover anhydrous sodium sulphate, then concentrated under reduced pressure to yield monoprotected diamine.

Reference： [1]Letters in drug design and discovery,2014,vol. 11,p. 756 - 761

53
[ 34619-03-9 ]
[ 21436-03-3 ]
[ 180683-64-1 ]

Reference： [1]Tetrahedron Asymmetry,2014,vol. 25,p. 1091 - 1094

54
(1S,2S)-cyclohexane-1,2-diamine (2S,4S)-xylaric acid salt [ No CAS ]
[ 21436-03-3 ]

Yield	Reaction Conditions	Operation in experiment
92.2%	With sodium hydroxide; In water;pH 9.0;	General procedure: (1R,2R)-Cyclohexane-1,2-diamine-(2R,4R)-xylaric acid salt (2) as obtained above wasneutralised to pH 9 with 2 M aqueous NaOH. Then the mixture wasextracted with CH2Cl2 (4 × 50 mL) and the combined organic layerswere dried over anhydrous Na2SO4 and concentrated in vacuo to givethe desired diamine 6, yield 92.9%, as white needle crystals

Reference： [1]Journal of Chemical Research,2014,vol. 38,p. 490 - 492

55
[ 67-56-1 ]
[ 16405-35-9 ]
[ 21436-03-3 ]
[PtCl(η¹-CH₂-CH₂OCH₃)(S,S-diaminocyclohexane)] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%		General procedure: KOH (104.5mg, 1.86mmol) was dissolved in 4mL of MeOH, at room temperature. Then the Zeise's salt (103.5mg, 0.28mmol) was dissolved, lowering the temperature to 0C (ice bath). A white precipitate of KCl immediately formed and the color of the solution changed from bright to pale yellow. After a couple of minutes R,R-chxn (114.19mg, 0.28mmol), previously dissolved in 0.5mL of methanol, was added in the reaction vessel. The reaction mixture was stirred for about 3h and then filtered, to eliminate KCl. The white product 2RRb was precipitated, from the mother liquor, by addition of about 25ml of diethyl-ether at 0C (yield 68mg, 60%).

Reference： [1]Journal of Organometallic Chemistry,2014,vol. 771,p. 40 - 46

56
[ 21436-03-3 ]
[ 66863-43-2 ]
(3S,3'S)-di-tert-butyl 3,3'-(((1S,2S)-cyclohexane-1,2-diylbis(azanediyl))bis(carbonyl))bis(3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%		EDCI (66.3 mg, 0.346 mmol) was added dropwise to a solution of compound 2 (100 mg, 0.311 mmol), triethylamine (0.345 mmol) and HOBT (46.7 mg, 0.345 mmol) in anhydrous CH2Cl2 (10 mL) at 0 C, and this reaction mixture was stirred for 30 min. (1S,2S)-(+)-1,2-cyclohexanediamine was then added to the reaction mixture in 0 C, and the reaction mixture was allowed to warm to room temperature overnight. The reaction was then quenched with saturated aqueous NaHCO3 solution and its pH was adjusted to 7-8. The organic phase was then washed with brine, dried over Na2SO4, and filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by column chromatography on silica gel (ethyl acetate/petroleum ether=1:1) to give 3 as a pale solid (yield:72%). [alpha]D25=+111.1 (c 10.0, CH2Cl2). 1H NMR (600 MHz, CDCl3) delta 8.34-7.71 (m, 1H), 7.51 (s, 1H), 7.22 (s, 1H), 7.09 (2H), 6.40 (1H), 4.84 (2H), 4.42 (s, 1H), 3.55 (s, 1H), 2.96 (s, 1H), 1.92 (s, 1H), 1.69 (2H), 1.50 (m, 8H), 1.21 (s, 2H). HRMS (ESI-TOF) Calcd for C40H50N6O6 [M+Na]+: 733.3687, Found: 733.3688.

Reference： [1]Tetrahedron,2014,vol. 70,p. 9077 - 9083

57
[ 36404-89-4 ]
[ 21436-03-3 ]
3,3'-[(1S,2S)-cyclohexane-1,2-diylbis(azanylylidene)bis(methanylylidene)]bis(1H-pyridin-2-one) [ No CAS ]

Reference： [1]Polyhedron,2015,vol. 102,p. 293 - 296

58
[ 21436-03-3 ]
3-bromo-9,9-dimethyl-9,10-dihydroacridine [ No CAS ]
9,9-dimethyl-3-(1H-pyrazol-1-yl)-9,10-dihydroacridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With NH-pyrazole; nitrogen; potassium carbonate; In hexane; ethyl acetate; toluene;	Synthesis of 9,9-dimethyl-3-(1H-pyrazol-1-yl)-9,10-dihydroacridine 5 3-bromo-9,9-dimethyl-9,10-dihydroacridine 4 (1.60 g, 5.0 mmol, 1.0 eq), pyrazole (340 mg, 5.0 mmol, 1.0 eq), CuI (48 mg, 0.25 mmol, 0.05 eq), K2CO3 (1.45 g, 10.5 mmol, 2.1 eq) and trans-1,2-cyclohexanediamine (142 mg, 1.0 mmol, 0.2 eq) were added to a dry pressure tube equipped with a magnetic stir bar. Then the tube was taken into a glove box and solvent toluene (5 mL) was added. The mixture was bubbled with nitrogen for 5 minutes and then the tube was sealed. The tube was taken out of the glove box and the mixture was stirred in an oil bath at 105-115 C. for 6 days. Then the mixture was cooled down to ambient temperature. The solvent was removed and the residue was purified through column chromatography on silica gel using hexane and ethyl acetate (10:1-5:1) as eluent to obtain the pure desired product as a yellow solid 1.16 g in 76% yield. 1H NMR (DMSO-d6, 400 MHz): delta 1.51 (s, 6H), 6.51 (t, J=2.0 Hz, 1H), 6.78 (d, J=8.0 Hz, 1H), 6.82 (td, J=8.0, 1.6 Hz, 1H), 7.07 (dd, J=7.6, 1.6 Hz, 1H), 7.19 (dd, J=8.0, 2.0 Hz, 1H), 7.26 (d, J=2.8 Hz, 1H), 7.36 (d, J=7.6 Hz, 1H), 7.43 (d, J=8.4 Hz, 1H), 7.71 (d, J=1.6 Hz, 1H), 8.35 (d, J=2.4 Hz, 1H), 9.06 (s, 1H).

Reference： [1]Patent: US2015/349279,2015,A1

59
[ 201230-82-2 ]
[ 21436-03-3 ]
[ 89976-15-8 ]
N,N'-((1S,2S)-cyclohexane-1,2-diyl)bis(1H-indole-7-carboxamide) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
16%	With palladium diacetate; In N,N-dimethyl-formamide; at 100℃; under 7500.75 Torr; for 24h;Autoclave;	General procedure: In a typical experiment, Pd(OAc)2 (5.6 mg, 0.025 mmol), triphenylphosphine (13.1mg, 0.05mmol), 7-iodoindole (224 mg, 0.9 mmol), the desired diamine nucleophile (0.45mmol) were placed in a stainless steel autoclave. After degassing the autoclave, triethylamine (0.5ml) and DMF (9mL) were added via cannula. The autoclave was then pressurized with 10 bar CO and the reaction was conducted for 24 h at 100C. The mixture was then concentrated and evaporated to dryness, with the crude being analysed by 1H NMR spectroscopy. The residue was dissolved in chloroform (20ml) and washed with water (3×20mL) and BRINE (3×20mL). The organic phase was dried over Na2SO4, filtered and the solvent was evaporated. All compounds were subjected to column chromatography (Silicagel 60 (Merck), 0.063-0.200mm) using EtOAc/CHCl3 (the exact ratios are specified in Section Characterization (3.5) for each compound).

Reference： [1]Tetrahedron,2016,vol. 72,p. 247 - 256

60
[ 34374-88-4 ]
[ 21436-03-3 ]
C₃₆H₄₂N₆O₆ [ No CAS ]

Reference： [1]Organic Letters,2016,vol. 18,p. 12 - 15

61
[ 81-86-7 ]
[ 21436-03-3 ]
C₃₀H₂₀Br₂N₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51.6%	In ethanol; at 78℃; for 24h;	396 g (2 mol) of A was added sequentially to a 2000 mL round bottom flask.115 g (1 mol) (1S, 2S)-1,2-cyclohexanediamine and 1500 mL of ethanol,Heating (heating temperature 78 C) reflux for 24 hours,After the reaction system is cooled to room temperature, 1000 mL of ethanol is distilled off.Then the remaining reaction system is placed in a 4 C environment for low temperature recrystallization,Filtration gave a crude product which was purified by column chromatography to afford 326 g of white solid.The white crystal was Compound B1 in a yield of 51.6%.
25.8%	In ethanol; for 24h;Reflux;	General procedure: A mixture of(-)-(R,R)-1,2-diaminocyclohexane or (+)-<strong>[21436-03-3](S,S)-1,2-diaminocyclohexane</strong>(1.15 g, 10 mmol) and 4-bromo-1,8-naphthalic anhydride(3.96 g, 20 mmol) in ethanol (200 mL) was refluxed for 24 h. The precipitatewas filtered after the solution cooling to room temperature. Thecrude product was purified by column chromatography to give compound(-)-(R,R)-CAI-Br and (+)-(S,S)-CAI-Br as white solids [30].

Reference： [1]Patent: CN109400587,2019,A .Location in patent: Paragraph 0059-0065
[2]Chemistry - A European Journal,2016,vol. 22,p. 9519 - 9522
[3]Organic electronics,2019,vol. 70,p. 71 - 77

62
[ 21436-03-3 ]
[ 18942-49-9 ]
C₃₄H₄₈N₄O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With dicyclohexyl-carbodiimide; In dichloromethane; at 20℃; for 10h;Cooling; Inert atmosphere;	For example 4a: A solution of N, N¢-dicyclohexylcarbodiimide (2.06 g, 10 mmol) in dried CH2Cl2 (15 mL) was dropwise added to a mixture of (1S,2S)-(+)-1,2-diaminocyclohexane (0.57 g, 5 mmol) and N-Boc-protected D-phenylalanine (2.65 g, 10 mmol) in dried CH2Cl2 (15 mL) at ice-salt bath under a nitrogen atmosphere. The mixture was stirred over 10 hours and filtered. The filtered cake was washed with CH2Cl2 for three times (5 mL × 3). The combined organic phase was dried over anhydrous Na2SO4. The solvent was removed under a vacuum and the residue was purified by column chromatography on silica gel to afford the pure 4a in 70% isolated yield as white solid.

Reference： [1]Tetrahedron Letters,2015,vol. 56,p. 6742 - 6746
[2]Journal of Organic Chemistry,2018,vol. 83,p. 13874 - 13887

63
[ 21436-03-3 ]
[ 33125-05-2 ]
C₃₂H₄₄N₄O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With dicyclohexyl-carbodiimide; In dichloromethane; at 20℃; for 10h;Cooling; Inert atmosphere;	General procedure: For example 4a: A solution of N, N¢-dicyclohexylcarbodiimide (2.06 g, 10 mmol) in dried CH2Cl2 (15 mL) was dropwise added to a mixture of (1S,2S)-(+)-1,2-diaminocyclohexane (0.57 g, 5 mmol) and N-Boc-protected D-phenylalanine (2.65 g, 10 mmol) in dried CH2Cl2 (15 mL) at ice-salt bath under a nitrogen atmosphere. The mixture was stirred over 10 hours and filtered. The filtered cake was washed with CH2Cl2 for three times (5 mL × 3). The combined organic phase was dried over anhydrous Na2SO4. The solvent was removed under a vacuum and the residue was purified by column chromatography on silica gel to afford the pure 4a in 70% isolated yield as white solid.

Reference： [1]Tetrahedron Letters,2015,vol. 56,p. 6742 - 6746

64
[ 3550-21-8 ]
[ 21436-03-3 ]
C₂₀H₂₅N₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	In dichloromethane; at 20℃; for 4h;	Benzhydryl isothiocyanate (1.97 g, 8.75 mmol) was added over a period of 1 h to a stirred solution of <strong>[21436-03-3](S,S)-1,2-diaminocyclohexane</strong> (1 g, 8.75 mmol) in anhyd CH2Cl2 (17 mL). The reaction mixture was stirred for a further 3 h at r.t. The solvent was removed under reduced pressure and the residue was purified by flash chromatography on silica gel eluting with hexane-EtOAc mixtures of increasing polarity. Catalyst IV was isolated as a white foam; yield: 2.3 g (6.83 mmol, 78%). The spectroscopic characterization of IV matched the literature data. 1H NMR (400 MHz, DMSO-d6): delta = 8.20 (br, 1 H, NHCS), 7.42 (br d, J =6.0 Hz, 1 H, NHCS), 7.40-7.20 (m, 10 H, CH Ar), 6.68 (s, 1 H, CHPh2), 3.75 (br, 1 H, CHNH), 2.43 (m, 1 H, CHNH2), 2.00 (m, 1 H, CH Cy), 1.78 (m, 1 H, CH Cy), 1.58 (m, 2 H, CH Cy), 1.25-0.95 (m, 4 H, CH Cy). 13C NMR (100 MHz, DMSO-d6): delta = 182.1 (C=S), 142.7 (C Ar), 128.4 (CH Ar), 127.2 (CH Ar), 126.9 (CH Ar), 60.4 (CHNH), 59.8 (CHPh2), 54.3 (CHNH2), 34.7 (CH2 Cy), 31.4 (CH2 Cy), 24.5 (CH2 Cy), 24.3 (CH2 Cy).

Reference： [1]Synthesis,2017,vol. 49,p. 319 - 325

65
[ 21436-03-3 ]
[ 65-22-5 ]
[5-hydroxymethyl-4-[2-(5-hydroxymethyl-2-methylpyridin-3-hydroxy-4-ylethylene)amino]cyclohexylimino}methyl-2-methylpyridin-3-ol] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%		Pyridoxal hydrochloride (0.406 g, 2 mmol) was dissolved inabsolute ethanol (15 ml) in the presence of KOH (0.112 g, 2 mmol)with stirring. After 1 h of stirring, the separated white solid (KCl)wasfiltered and the obtained clear solution was added to a solutionof 1,2-diaminocyclohexane (0.114 g, 1 mmol) in ethanol (15 ml)with stirring and the resulting reaction mixture was refluxed for4 h. The completeness of the condensation reaction was checked byperforming thin layer chromatography. The solution was evapo-rated by rotary evaporator and sticky mass obtained was washedby cold ether and dried under vacuum. (Yield: 0.359 g, 87%; Melting point: >250 C). 1H NMR (300 MHz, DMSO-d6): d ppm: 8.85(s, 2Ha), 7.81(s, 2Hc), 4.60-4.48 (m, 4He), 3.59 (s, 2Hd), 2.30 (s, 6Hb),1.93-1.45 (m, 8Hg). Anal.calcd. for C22H28N4O4: C, 64.06; H, 6.84; N,13.58. Found: C, 63.89; H, 6.53; N, 13.25%.TOF MS ES+, m/z = 413.47calc. for C22H29N4O4 = 413.22.

Reference： [1]Journal of Photochemistry and Photobiology A: Chemistry,2017,vol. 334,p. 86 - 100

66
[ 21436-03-3 ]
C₂₀H₂₉ClO₂ [ No CAS ]
N,N'-bis(ent-16-carbonylkaurane-19-acyl)-(1S,2S)-1,2-cyclohexanediamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55.4%	With potassium carbonate; In dichloromethane; at 20℃;	(1S,2S) -1,2-cyclohexanediamine (0.124 g, 0.1 mmol) was dissolved in 5 ml of anhydrous dichloromethane and added dropwise to a solution containing the compound (VI (0.94 g, 2.8 mmol) and potassium carbonate (0. 4 g, 2.9 mmol) in 10 mlIn anhydrous methylene chloride. After 20 minutes, the reaction mixture was transferred to room temperature for 1.5-3 h. After completion of the reaction, the filtrate was filtered and the solid was washed with dichloromethane. The filtrate and the washing solution were combined to give the organic layer. And the mixture was washed with an eluent of petroleum ether: acetone volume ratio = 8: 1, and the resulting eluent was evaporated to give a white solid, 0. 431 g, yield 55. 4%.

Reference： [1]Patent: CN105399644,2016,A .Location in patent: Paragraph 0036; 0037

67
[ 21436-03-3 ]
5-chloro-N1-(2-chloro-9-isopropyl-9H-purin-6-yl)benzene-1,3-diamine [ No CAS ]
N6-(3-amino-5-chlorophenyl)-N2-((1S,2S)-2-aminocyclohexyl)-9-isopropyl-9H-purine-2,6-diamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With triethylamine; In 1-methyl-pyrrolidin-2-one; at 160℃; for 16h;	General procedure: To a solution of 2-chloro-N-(3-chlorophenyl)-9-ethyl-9H-purin-6-amine (0.360 g, 1.17 mmol) in 6.0 mL of NMP were added TEA (0.33 mL, 2.3 mmol), and cis-cyclohexane-1,2-diamine (0.400 g, 3.50 mmol) at rt. The reaction mixture was stirred at 160 C for 16 h, allowed to cool to rt, then partitioned between water and dichloromethane. The organic layer was washed with brine, dried (MgSO4), and concentrated, and finally purified by automated flash column chromatography (dichloromethane-methanol with 10% NH4OH: 0-10% gradient) to give 1 (0.244 g, 54%) as a brownish solid.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 406 - 412

68
[ 21436-03-3 ]
[ 190654-77-4 ]
N2-((1S,2S)-2-aminocyclohexyl)-N6-(3-chlorophenyl)-9-ethyl-9H-purine-2,6-diamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%	With triethylamine; In 1-methyl-pyrrolidin-2-one; at 160℃; for 16h;	General procedure: To a solution of 2-chloro-N-(3-chlorophenyl)-9-ethyl-9H-purin-6-amine (0.360 g, 1.17 mmol) in 6.0 mL of NMP were added TEA (0.33 mL, 2.3 mmol), and cis-cyclohexane-1,2-diamine (0.400 g, 3.50 mmol) at rt. The reaction mixture was stirred at 160 C for 16 h, allowed to cool to rt, then partitioned between water and dichloromethane. The organic layer was washed with brine, dried (MgSO4), and concentrated, and finally purified by automated flash column chromatography (dichloromethane-methanol with 10% NH4OH: 0-10% gradient) to give 1 (0.244 g, 54%) as a brownish solid.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 406 - 412

69
[ 21436-03-3 ]
[ 190654-78-5 ]
N2-((1S,2S)-2-aminocyclohexyl)-N6-(3-chlorophenyl)-9-isopropyl-9H-purine-2,6-diamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	With triethylamine; In 1-methyl-pyrrolidin-2-one; at 160℃; for 16h;	General procedure: To a solution of 2-chloro-N-(3-chlorophenyl)-9-ethyl-9H-purin-6-amine (0.360 g, 1.17 mmol) in 6.0 mL of NMP were added TEA (0.33 mL, 2.3 mmol), and cis-cyclohexane-1,2-diamine (0.400 g, 3.50 mmol) at rt. The reaction mixture was stirred at 160 C for 16 h, allowed to cool to rt, then partitioned between water and dichloromethane. The organic layer was washed with brine, dried (MgSO4), and concentrated, and finally purified by automated flash column chromatography (dichloromethane-methanol with 10% NH4OH: 0-10% gradient) to give 1 (0.244 g, 54%) as a brownish solid.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 406 - 412

70
[ 21436-03-3 ]
C₂₇H₃₉NO₅ [ No CAS ]
C₃₂H₄₉N₃O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	In dichloromethane; at 20℃;	General procedure: The mono-squaramide 5 (0.46 g, 1 mmol) was added to a stirred solution of (S,S)- or (R,R)-cyclohexane-1,2-diamine 6 (0.11 g, 1 mmol) in anhyd CH2Cl2 (25 mL). The reaction mixture was stirred at r.t. overnight. TLC indicated that the reaction was complete. The solvent was removed under reduced pressure and the crude product was purified by column chromatography (silica gel, MeOH/CH2Cl2 = 1:10). Catalyst 2a White solid; yield: 0.44 g (82%); mp 174.3-175.1 C; [alpha]D20 -255.6 (c 1.0, CHCl3). IR (KBr): 974, 1029, 1096, 1128, 1150, 1181, 1223, 1375, 1467, 1529, 1585, 1669, 1722, 1794, 2849, 2937, 3255 cm-1. 1H NMR (400 MHz, CDCl3/TMS): delta = 0.71 (s, 3 H), 0.84-0.90 (m, 1 H), 0.94 (s, 3 H), 0.97-1.05 (m, 3 H), 1.09 (d, J = 11.2 Hz, 1 H), 1.16 (s, 3 H), 1.24 (t, J = 6.8 Hz, 4 H), 1.28-1.44 (m, 8 H), 1.54-2.01 (m, 13 H), 2.05 (d, J = 11.2 Hz, 1 H), 2.63 (s, 1 H), 2.81 (s, 3 H), 3.62 (s, 1 H), 4.00-4.13(m, 2 H), 4.28 (s, 1 H). 13C NMR (100 MHz, CDCl3/TMS): delta = 13.4, 14.2, 18.9, 20.4, 21.7, 24.6, 28.9, 34.0, 38.0, 39.9, 41.3, 42.3, 43.7, 55.6, 56.9, 60.0, 62.8, 177.5,182.1. HRMS: m/z [M+ H]+ calcd for C32H50N3O4: 540.3801; found: 540.3801.

Reference： [1]Synthesis,2017,vol. 49,p. 1307 - 1314

71
[ 21436-03-3 ]
[ 100-39-0 ]
[ 207450-11-1 ]

Yield	Reaction Conditions	Operation in experiment
96%	In acetonitrile; at 20℃; for 2h;Inert atmosphere;	To the solution (1S,2S)-cyclohexane-1,2-diamine ( 11.41 g, 100.0 mmol) in dry MeCN (130.0 mL) was added dropwise benzyl bromide (1.46 mL,10 mmol, 0.1 equiv) in MeCN (20.0 mL) at room temperature over 2 h. The resultant white, heterogeneous solution was concentrated to dryness and extracted via EtOAc and saturated NaHCO3. The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel column chromatography. Yield 96%. 1H NMR (500 MHz, MeOD): delta ppm 7.22-7.38 (m, 5H), 4.58 (br s, 3H), 3.89 (d, J = 13.0 Hz, 1H), 3.65 (d, J = 13.0 Hz, 1H), 2.35-2.40 (m, 1H), 2.11-2.15 (m, 2H), 1.87-1.89 (m, 1H), 1.66-1.74 (m, 2H), 1.01-1.37 (m, 4H). 13C NMR (126 MHz, CD3OD): delta ppm 144.39, 132.11, 130.66, 66.31, 58.21, 54.36, 38.46, 34.37, 28.95, 28.91. ESIMS (m/z) 205 [M+H]+, 227 [M+Na]+, 203 [M-H]-.

Reference： [1]Tetrahedron Letters,2017,vol. 58,p. 1441 - 1444

72
[ 21436-03-3 ]
C₂₅H₃₅NO₅ [ No CAS ]
C₃₀H₄₅N₃O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	In dichloromethane; at 20℃;	The mono-squaramide S3 (0.46 g, 1 mmol) was added to a stirred solution of (S,S)- or (R,R)- cyclohexane-1,2-diamine S4a or S4b (0.11 g, 1 mmol) in dry dichloromethane (25 mL). The reaction mixture was stirred at room temperature overnight. TLC indicated that the reaction was complete. The solvent was removed under reduced pressure and the crude product was purified by column chromatography (silica gel, methanol / dichloromethane = 1/10). Squaramide 1a: White solid; 0.44 g, 82% yield; mp: 174.3-175.1 oC; [alpha]D20 = -255.6 (c 1.0, CHCl3).IR (KBr, cm-1): nu 974, 1029, 1096, 1128, 1150, 1181, 1223, 1375, 1467, 1529, 1585, 1669, 1722, 1794, 2849, 2937, 3255.1H NMR (400 MHz, CDCl3, TMS): delta 0.71 (s, 3H), 0.84-0.90 (m, 1H), 0.94 (s, 3H), 0.97-1.05 (m, 3H), 1.09 (d, J = 11.2 Hz, 1H), 1.16 (s, 3H), 1.24 (t, J = 6.8 Hz, 4H), 1.28-1.44 (m, 8H), 1.54-2.01 (m, 13H), 2.05 (d, J = 11.2 Hz, 1H), 2.63 (s, 1H), 2.81 (s, 3H), 3.62 (s, 1H), 4.00-4.13 (m, 2H), 4.28 (s, 1H).13C NMR (100 MHz, CHCl3): delta 13.4, 14.2, 18.9, 20.4, 21.7, 24.6, 28.9, 34.0, 38.0, 39.9, 41.3, 42.3, 43.7, 55.6, 56.9, 60.0, 62.8, 177.5, 182.1.HR-MS (m/z): calcd. for C32H50N3O4 [M+H]+ 540.3801, found 540.3801.

Reference： [1]Tetrahedron Letters,2017,vol. 58,p. 4487 - 4490

73
[ 18959-30-3 ]
[ 21436-03-3 ]
C₂₂H₁₄F₄N₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With acetic acid; at 120℃; for 4h;	In a 2000-mL round-bottomed flask, 200 g (1.1 mol) of A, 57 g (0.5 mol) of (1S,2S)-1,2-cyclohexanediamine and 1000 mL of glacial acetic acid were successively added and the mixture was heated (heated at 120 C.) for 4 hours under reflux. ,After the reaction system was cooled to room temperature, 500 mL of glacial acetic acid was distilled off, and the remaining reaction system was recrystallized at a low temperature in a 4 C. environment, and the crude product was filtered and recrystallized with a small amount of glacial acetic acid to obtain 167 g of white needle crystals. The white crystals were compound B1 with a yield of 75%.

Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 2889 - 2893
Angew. Chem.,2018,vol. 130,p. 2939 - 2943,5
[2]Patent: CN108117506,2018,A .Location in patent: Paragraph 0054; 0056; 0058

74
[ 21436-03-3 ]
5-chloro-N-(2,4-dimethoxybenzyl)-2,4-difluoro-N-(thiazol-2-yl)benzene sulfonamide [ No CAS ]
4-(((1S,2S)-2-aminocyclohexyl)amino)-5-chloro-N-(2,4-dimethoxybenzyl)-2-fluoro-N-(thiazol-2-yl)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With triethylamine; In N,N-dimethyl-formamide; at 20℃; for 2h;	A mixture of 5-chloro-N-[(2,4-dimethoxyphenyl) methyl]-2,4-difluoro-N-thiazol-2-yl-benzenesulfonamide (8.60 g, 18.7 mmol), (1 S,2S)-cyclohexane-1 ,2-diamine (4.26 g, 37.3 mmol), and triethylamine (13.0 mE, 93.3 mmol) was stirred in N,N-dimethylformamide (93 mE) at room temperature for 2 h. 100 mE of aqueous NaHCO3 were added and the aqueous phase was extracted with dichloromethane. The organic phase was dried with MgSO4, filtered and concentrated on silica gel. Purification by silica gel chromatography (0-10% MeOH/DCM gradient) to afford the title compound (8.70 g, 84%) as a white solid. ECMS (ESI) mlz: 556.1 [M+H]+. ?H NMR (400 MHz, Chloroform-d) oe 7.72 (d, J=7.1 Hz, 1H), 7.38 (d, J=3.6 Hz, 1H), 7.21 (dt, J=8.4, 1.0 Hz, 1H), 6.95 (d, J=3.6 Hz, 1H),6.45 (d, J=12.7 Hz, 1H), 6.36 (d, J=7.4 Hz, 2H), 5.19 (s, 2H),4.90-4.79 (m, 1H), 3.75 (s, 3H), 3.75 (s, 3H), 3.01-2.92 (m, 1H), 2.75-2.61 (m, 1H), 2.11-1.93 (m, 2H), 1.86-1.67 (m, 2H), 1.39-1.05 (m, 4H).

Reference： [1]Patent: US2018/105504,2018,A1 .Location in patent: Paragraph 0431; 0432

75
[ 779-90-8 ]
[ 21436-03-3 ]
C₈₄H₁₀₈N₁₂ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 11228 - 11232
Angew. Chem.,2018,vol. 130,p. 11398 - 11402,5

76
[ 21436-03-3 ]
[ 81502-74-1 ]
C₇₂H₈₄N₁₂O₄ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 11228 - 11232
Angew. Chem.,2018,vol. 130,p. 11398 - 11402,5

77
[ 366-18-7 ]
copper(II) perchlorate hexahydrate [ No CAS ]
[ 21436-03-3 ]
[Cu(S,S-trans-1,2-diaminocyclohexane)(2,2'-bipyridine)](ClO₄)₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%		General procedure: Equimolar quantity of Cu(ClO4)26H2O (0.42 g, 1.14 mmol) and (±trans)-1,2-diaminocyclohexane(0.13 g, 1.14 mmol) were dissolved in minimum amount of methanol. Themixture was stirred for 5 min, followed by addition of 2,2'-bipyridine (0.18 g,1.14 mmol). This was stirred for 2 h and the reaction mixture was filtered and the complexwas dried under reduced pressure to give 0.54 g (95%) of 1a. Crystals suitable forsingle crystal XRD were obtained from acetonitrile solution of 1a by slow evaporation.

Reference： [1]Journal of Coordination Chemistry,2018,vol. 71,p. 3615 - 3638

78
[ 66-71-7 ]
copper(II) perchlorate hexahydrate [ No CAS ]
[ 21436-03-3 ]
[Cu(S,S-trans-1,2-diaminocyclohexane)(1,10-phenanthroline)](ClO₄)₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%		General procedure: Equimolar quantity of Cu(ClO4)2*6H2O (0.395 g, 1.06 mmol) and (±trans)-1,2-diaminocyclohexane(0.12 g, 1.06 mmol) were dissolved in minimum amount of methanol. Themixture was stirred for 5 min, followed by addition of 1,10-phenanthroline (0.21 g,1.06 mmol). This was stirred for 2 h and the reaction mixture was filtered and the complexwas dried under reduced pressure to give 0.58 g (94%) of 2a. Crystals suitable forsingle crystal XRD were obtained from acetonitrile solution of 2a by slow evaporation.

Reference： [1]Journal of Coordination Chemistry,2018,vol. 71,p. 3615 - 3638

79
[ 51300-90-4 ]
[ 21436-03-3 ]
[ 180683-64-1 ]

Reference： [1]European Journal of Organic Chemistry,2019,vol. 2019,p. 2115 - 2128

80
[ 180683-64-1 ]
[ 21436-03-3 ]

Reference： [1]European Journal of Organic Chemistry,2019,vol. 2019,p. 2115 - 2128

81
[ 553-26-4 ]
[ 42865-19-0 ]
[ 21436-03-3 ]
C₂₂H₃₀N₆O₂⁽²⁺⁾*2Br^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%		(1) Weigh 1.14 g (1S, 2S)-1,2-cyclohexanediamine into 150 mL of acetonitrile.The mixture was stirred in an ice bath, and 3.0 g of ethyl 2-bromoisocyanate was added dropwise to the above solution.A white solid precipitated, and after 4 hours of reaction, it was centrifuged.After washing with 100 mL of dichloromethane and drying in vacuo, the intermediate product of the chiral resolving agent was 3.98 g, the yield was 96%;(2) Weigh 2.07g of the product prepared in step 1 and dissolve it in 100mL of ethanol, add 0.78g of 4,4'-bipyridyl, stir it magnetically, and heat at 80oC. After 36h of reaction, the solvent is distilled off under reduced pressure, and 100mL of acetic acid is used. The ester was washed and vacuum dried to obtain 2.65 g of a chiral resolving agent (molecular structure as shown in Fig. 1) of the patent, and the yield was 93%.

Reference： [1]Patent: CN110256261,2019,A .Location in patent: Paragraph 0014

82
[ 3541-37-5 ]
[ 21436-03-3 ]
cis‑1S,2S‑N1,N2‑bis{(benzo[b]thiophen‑2‑yl)methylene}diaminocyclohexane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	In ethanol; at 20℃; for 5h;Schlenk technique; Inert atmosphere;	A solution of benzo[b]thiophene-2-carboxaldehyde(2.76 g, 16.98 mmol) in ethanol (25 ml) is added to a solution of cis-1,2-diaminocyclohexane (0.97 g, 8.49 mmol) in ethanol (25 ml). After stirring for 1 h, at room temperature, a yellow precipitate was formed. Stirring was continued for 4 h, and then the product was filtered, washed with copious amounts of ethanol (30 ml), diethyl ether (30 ml)and dried under vacuum. Recrystallization from CH2Cl2/Et2O (1:1) afforded yellow crystals. Yield: (79%). Color (yellow); Anal. Calcd. for C24H22N2S2(1): C, 71.60; H, 5.51; N, 6.96; S, 15.93 %. Found: C, 71.77; H, 5.54; N, 7.08; S, 15.77%; 1H-NMR (ppm, CDCl3): delta: 8.39 (s, 2H, N=CH), 7.81-7.71 (m, 4H, Harom.), 7.42-7.28 (m, 6H, Harom.), 3.76 (m, 2H, N-CH cyclohex.), 2.06 (m, 4H, N-C-CH2-cyclohex.), 1.74 (m, 2H, cyclohex.), and 1.59 (m, 2H, cyclohex.); 13C NMR (CDCl3): delta : 153.8, 143.9, 140.6, 139.6, 127.0, 125.8, 124.5, 122.7, 69.6, 30.4, 23.1; FT-IR (nu/cm-1): nu(C=N) 1632(s).

Reference： [1]Transition Metal Chemistry,2020,vol. 45,p. 41 - 46

83
[ 21436-03-3 ]
dichloro 2-(2,5-dimethoxyphenyl)-1H,3aH,11bH-imidazo[4,5-f][1,10]phenanthroline platinum (II) [ No CAS ]
C₂₇H₃₀N₆O₂Pt⁽²⁺⁾*2Cl^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
Ca. 92%		Dissolve 0.5mmol (H-MPP) PtCl2 in 40mL anhydrous methanol.A yellow solid suspension was obtained after heating magnetic stirring at 65 C for 20 min.Then add 8 times (1S, 2S)-(+)-1,2-cyclohexanediamine (S-DACH) (0.6mL),Heating at 65 C and continuing reflux to make the suspension completely dissolved,And filtered while hot to remove insoluble solids,Wait for the filtrate to evaporate slowly at room temperature to precipitate a red precipitate.The solid was recrystallized from anhydrous ethanol and distilled water at a volume ratio of 3: 1. After most of the ethanol and distilled water were evaporated, a large amount of acetone was added to precipitate a red solid, and a more pure MPP-Pt-S complex product was obtained by filtration. . The obtained product was recrystallized three times with anhydrous ethanol and distilled water to obtain a red complex without going through a column. The yield is about 92%, and its structural formula is shown in Fig. 1

Reference： [1]Patent: CN110256501,2019,A .Location in patent: Paragraph 0043; 0049; 0050; 0051; 0057; 0058; 0059; 0065

84
[ 4097-89-6 ]
[ 3163-76-6 ]
[ 21436-03-3 ]
C₅₁H₆₀N₁₀ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2019,vol. 58,p. 16275 - 16281
Angew. Chem.,2019,vol. 131,p. 16421 - 16427,7

85
[ 21436-03-3 ]
[ 67753-41-7 ]
C₆₀H₆₀N₆P₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%		(1) At 298K, 7.5 g of 4-[bis(4-formylphenyl)phosphanyl]benzaldehyde(CHO-PPh3) was dissolved in 2.5 L of ethyl acetate solvent and sonicated for 10 minutes to fully dissolve.On the other side, 3.7 g of cyclohexane-1,2-diamine (M1) was dissolved in 500 mL of ethyl acetate.Sonicate for 10 minutes to fully dissolve. then,The above amine solution was slowly added dropwise to the tris (tetrabenzaldehyde) phosphorus solution, in which the dropping process was not agitated, and the dropping rate was about 1 drop / second. After the dropping was completed, the reaction solution was left to stand at room temperature for 3 days to react. .After the reaction was completed, the mixture was filtered and the filtrate was concentrated.5 mL of dichloromethane was added to the concentrated filtrate and 50 mL of methanol was slowly added for recrystallization.Filter to obtain a light yellow solid porous organic cage,The yield was 83%.
	With acetic acid; In tetrahydrofuran; at 44.84℃; for 60h;Inert atmosphere;	Under 318K and inert gas atmosphere, 4.29 grams of aldehyde group functionalized PPh3monomer (Figure 3, L1) was dissolved in 500.0 ml of tetrahydrofuran solvent, and 1 was added at the same time .2 cyclohexanediamine comonomer 2.12g (L55 in Figure 3), and adding 1ml of acetic acid as a catalyst, the mixed solution is still under the reaction conditions for 60h to obtaina crude productcontaining PPh3porous organic cage ligand.

Reference： [1]Patent: CN110357925,2019,A .Location in patent: Paragraph 0081-0082; 0084
[2]Patent: CN110835343,2020,A .Location in patent: Paragraph 0030; 0042; 0044

86
[ 1010100-26-1 ]
[ 21436-03-3 ]
3-(5-(((1S,2S)-2-aminocyclohexyl)amino)-1-oxoisoindolin-2-yl)piperidine-2,6-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	With copper(l) iodide; caesium carbonate; In N,N-dimethyl-formamide; at 70℃;Inert atmosphere;	3-(5-bromo-1-oxoisoindolin-2-yl)piperidine-2,6-dione (2-3, 2000 mg, 6.19 mmol), CuI (354 mg, 1.86 mmol), Cs2CO3 (4.03 g, 12.4 mmol) and (1S,2S)-cyclohexane-1,2-diamine (5-1, 1.41 g, 12.4 mmol) were combined under nitrogen atmosphere and DMF (25 mL) was added. The resulting mixture was stirred at 70 C. overnight, and then filtered through a pad of Celite and concentrated to dryness. The crude material was purified via silica gel chromatography eluting with 0 to 100% EtOH (with 1% Et3N as a modifier) in DCM to afford I-7 (1273 mg, 3.45 mmol, 56% yield) as a light green solid. MS [M+H]+=357.1.

Reference： [1]Patent: US2020/16143,2020,A1 .Location in patent: Paragraph 1327; 1328

87
[ 32608-29-0 ]
[ 21436-03-3 ]
(1S,2S)-N₁,N₂-bis(4-chloro-8-methoxyquinolin-2-yl)cyclohexane-1,2-diamine [ No CAS ]

Reference： [1]Chemical Communications,2019,vol. 55,p. 14351 - 14354

88
[ 64-18-6 ]
[ 1010100-26-1 ]
[ 21436-03-3 ]
3-(5-(((1S,2S)-2-aminocyclohexyl)amino)-1-oxoisoindolin-2-yl)piperidine-2,6-dione formic acid salt [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35%		To 3-(5-bromo-1-oxoisoindolin-2-yl)piperidine-2,6-dione (2-3, 100 mg, 0.309 mmol), CuI (17.7 mg, 0.093 mmol), Cs2CO3 (202 mg, 0.619 mmol) and (1S,2S)-cyclohexane-1,2-diamine (5-1, 70.7 mg, 0.619 mmol) under an atmosphere of nitrogen was added DMF (2 mL) and the resulting reaction mixture was stirred for 24 h at 70 C. The reaction mixture was diluted with MeCN and formic acid (0.05 mL) was added. The reaction mixture was then filtered and concentrated to dryness. The obtained crude material was purified by reverse phase HPLC (eluting with MeCN/H2O with 0.1% formic acid). The fractions containing the desired product were combined and lyophilized to afford the for mate salt of I-7 (43.1 mg, 0.107 mmol, 35% yield) as a white solid. MS [M+H]+=357.2. 1H NMR (400 MHz, Deuterium Oxide) 6 8.36 (s, 1H), 7.51 (d, J=8.5 Hz, 1H), 6.89-6.70 (m, 2H), 4.99 (dd, J=13.3, 5.2 Hz, 1H), 4.40 (d, J=17.4 Hz, 1H), 4.30 (d, J=17.1 Hz, 1H), 3.53-3.35 (m, 1H), 3.02 (td, J=11.1, 3.8 Hz, 1H), 2.91-2.70 (m, 2H), 2.40 (qd, J=12.9, 5.2 Hz, 1H), 2.19-1.99 (m, 3H), 1.82-1.62 (m, 2H), 1.52-1.37 (m, 1H), 1.35-1.25 (m, 2H), 1.23-1.08 (m, 1H).

Reference： [1]Patent: US2020/16143,2020,A1 .Location in patent: Paragraph 1319; 1320

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