[ CAS No. 484-11-7 ] {[proInfo.proName]}

Name: 484-11-7|2,9-Dimethyl-1,10-phenanthroline|98%
Brand: Ambeed
SKU: A199979
Price: 10.0 USD
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Quality Control of [ 484-11-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 484-11-7 ]

Product Details of [ 484-11-7 ]

CAS No. :	484-11-7	MDL No. :	MFCD00004973
Formula :	C₁₄H₁₂N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	IYRGXJIJGHOCFS-UHFFFAOYSA-N
M.W :	208.26	Pubchem ID :	65237
Synonyms :

Calculated chemistry of [ 484-11-7 ]

Physicochemical Properties

Num. heavy atoms :	16
Num. arom. heavy atoms :	14
Fraction Csp3 :	0.14
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	66.98
TPSA :	25.78 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-5.26 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.22
Log Po/w (XLOGP3) :	3.26
Log Po/w (WLOGP) :	3.4
Log Po/w (MLOGP) :	2.4
Log Po/w (SILICOS-IT) :	3.91
Consensus Log Po/w :	3.04

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.83
Solubility :	0.0306 mg/ml ; 0.000147 mol/l
Class :	Soluble
Log S (Ali) :	-3.48
Solubility :	0.0697 mg/ml ; 0.000335 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-5.78
Solubility :	0.000342 mg/ml ; 0.00000164 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.6

Safety of [ 484-11-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P302+P352-P261-P304+P340-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 484-11-7 ]

* 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 [ 484-11-7 ]
Downstream synthetic route of [ 484-11-7 ]

[ 484-11-7 ] Synthesis Path-Upstream 1~6

1
[ 18978-78-4 ]
[ 75-07-0 ]
[ 109-92-2 ]
[ 484-11-7 ]

Reference： [1] Organic and Biomolecular Chemistry, 2011, vol. 9, # 2, p. 347 - 350

2
[ 942267-04-1 ]
[ 484-11-7 ]

Reference： [1] Tetrahedron Letters, 2007, vol. 48, # 19, p. 3359 - 3362

3
[ 18978-78-4 ]
[ 78267-54-6 ]
[ 484-11-7 ]

Reference： [1] Journal of the American Chemical Society, 1948, vol. 70, p. 3994

4
[ 66-71-7 ]
[ 917-54-4 ]
[ 3002-77-5 ]
[ 484-11-7 ]

Reference： [1] Journal of Heterocyclic Chemistry, 1995, vol. 32, # 3, p. 1081 - 1084
[2] European Journal of Medicinal Chemistry, 1984, vol. 19, # 5, p. 399 - 404

5
[ 21710-12-3 ]
[ 90030-13-0 ]
[ 484-11-7 ]
[ 88503-31-5 ]

Reference： [1] New Journal of Chemistry, 1988, vol. 12, p. 15 - 20

6
[ 484-11-7 ]
[ 57709-61-2 ]

Reference： [1] Journal of the American Chemical Society, 2007, vol. 129, # 7, p. 1856 - 1857
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1996, # 1, p. 75 - 82
[3] Journal of Heterocyclic Chemistry, 1994, vol. 31, # 1, p. 1 - 10
[4] Journal of Heterocyclic Chemistry, 1981, vol. 18, p. 599 - 602
[5] Journal of Heterocyclic Chemistry, 1981, vol. 18, p. 599 - 602
[6] Journal of Heterocyclic Chemistry, 1981, vol. 18, p. 599 - 602
[7] Organic and Biomolecular Chemistry, 2011, vol. 9, # 8, p. 2648 - 2653
[8] Chemical Communications, 2011, vol. 47, # 39, p. 11008 - 11010
[9] Inorganic Chemistry, 2014, vol. 53, # 3, p. 1712 - 1720
[10] Tetrahedron Letters, 2014, vol. 56, # 1, p. 182 - 186
[11] Catalysis Today, 2017, vol. 279, p. 77 - 83
[12] Dalton Transactions, 2016, vol. 45, # 29, p. 11624 - 11627
[13] Inorganic Chemistry, 2018, vol. 57, # 10, p. 5782 - 5790
[14] Synlett, 2018, vol. 29, # 10, p. 1362 - 1366
[15] Synlett, 2018, vol. 29, # 10, p. 1362 - 1366
[16] Inorganic Chemistry, 2018, vol. 57, # 24, p. 15270 - 15279

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Yield	Reaction Conditions	Operation in experiment
95%	With selenium(IV) dioxide In 1,4-dioxane for 1h; Heating;
94%	With selenium(IV) dioxide In 1,4-dioxane; lithium hydroxide monohydrate for 2h; Reflux;
94%	With selenium(IV) dioxide In tetrahydrofuran; lithium hydroxide monohydrate for 5h; Reflux;	1.1; 2.1; 3.1; 4.1; 5.1; 6.1 (1) Under stirring conditions, SeO2 (5.3g, 48mmol) was added to a composite solvent consisting of 120mL tetrahydrofuran and 10mL water, heated to reflux, and then added dropwise 2,9-dimethyl-1,10-o The tetrahydrofuran solution of phenanthroline [obtained from 2,9-dimethyl-1,10-phenanthroline (5.0g, 24mmol) dissolved in 150mL tetrahydrofuran], after the addition is complete, react for 5.0h, then take advantage of Hot filtration, the obtained filtrate is left to cool until a solid precipitates, and then the filtrate is filtered to obtain a reddish brown flocculent solid, namely 2,9-diformaldehyde-1,10-phenanthroline (5.0g, yield 94%)

93%	With selenium(IV) dioxide In 1,4-dioxane; lithium hydroxide monohydrate Reflux;
88%	With selenium(IV) dioxide In 1,4-dioxane; lithium hydroxide monohydrate for 2h; Reflux;
86%	With selenium(IV) dioxide In 1,4-dioxane; lithium hydroxide monohydrate for 0.5h; Reflux; Inert atmosphere; Schlenk technique;	Synthesis of 2,9-dicarbaldehyde-1,10-phenanthroline The ligand was synthesized from a modified literature procedure [52]: To a solution of selenium oxide (2.26 g, 20.41 mmol) in deionized water (5 mL) and 1,4-dioxane (70 mL), 2,9-dimethyl-1,10-phenanthroline (2.00 g, 9.60 mmol) in 1,4-dioxane (20 mL) was added in a dropwise manner. The reaction mixture was refluxed for 0.5 h, during which the color of the reaction mixture changed from yellow to reddish brown with black deposits. Upon cooling to room temperature, the brown solids were collected by suction filtration and washed with Et2O (10 mL × 3). These solids were further purified by recrystallization with warm CHCl3and allowed to cool and stand overnight. Yellowish orange solids were collected by suction filtration and washed with Et2O (10 mL × 3) to give 2,9-dicarbaldehyde-1,10-phenanthroline.1H-NMR signals are consistent with that of the literature reported [50]. Yield: 1.95 g, 86%.
85%	With selenium(IV) oxide In 1,4-dioxane for 0.166667h; Heating; microwave;
85%	With selenium(IV) dioxide In 1,4-dioxane for 2h; Reflux;
85%	With selenium(IV) dioxide In 1,4-dioxane; lithium hydroxide monohydrate for 0.5h; Reflux;
85%	With selenium(IV) dioxide In 1,4-dioxane at 60 - 100℃; for 14.5h;
85%	With selenium(IV) dioxide In 1,4-dioxane at 85℃; for 6h;
85%	With selenium(IV) dioxide In 1,4-dioxane; lithium hydroxide monohydrate at 20℃; for 0.333333h;	2.2. Procedure for synthesis of compound 2 Neocuproine (14.4 mmol, 1 equiv., 3 g) was dissolved in dioxane(50 mL) and water (2 mL), and the resulting solution was stirred for20 min. at room temperature. A suspension of selenium dioxide(64.8 mmol, 4.5 equiv., 7.19 g) in a mixture of dioxane (130 mL)and water (5.2 mL) was then added, and the color changed frombrown to white. The resulting suspension was refluxed for 24 h,and then the black colored precipitate (selenium metal) was filteredwhile hot. The resulting solution was cooled and the resultingprecipitate was filtered to give the desired compound whichwas purified by crystallization from acetone.
81%	With selenium(IV) dioxide In 1,4-dioxane; lithium hydroxide monohydrate for 2h; Reflux;
81.75%	With selenium(IV) dioxide In 1,4-dioxane for 12h;	2.2.1. Synthesis of 1,10-phenanthroline-2,9-dicarbaldehyde 1,10-Phenanthroline-2,9-dicarboxaldehyde was synthesized accordingto a previously reported method [36-40]. To a double-mouthedround bottom flask, 30 mL of a dioxane solution dissolved in seleniumdioxide (4.5 g, 40.55 mmol) was added and placed in a water bath. Witha constant-pressure drop funnel, 100 mL of dioxane solution dissolved inneocopper reagent (3 g, 14.40 mmol) was added drop by drop to thedouble-bottomed flask. After 12 h in the water bath reaction, while hotfilter out the tar and selenium collection filtrate, the filtrate was yellow.When the filtrate was cooled, a large number of yellow precipitates weregenerated, namely 1,10-phenanthroline-2,9-dicarboxaldehyde crudeproduct. After filtering out the crude product, it was collected and dissolvedin benzene, to which n-hexane was added for recrystallization.Finally, the resulting product was filtered and dried to obtain a goldenyellow needle-like solid. Golden yellow needle-like solid 3.1313 g, yield:81.75%. M.p.: 238-240 C. Anal. Calcd. for C14H8N2O2 (%): C, 71.18; H,3.41; N, 11.86. Found: C, 71.29; H, 3.25; N, 11.62. 1H NMR (500 MHz,DMSO) δ 10.36 (d, J = 0.8 Hz, 1H), 8.80 (dd, J = 8.2, 0.8 Hz, 1H), 8.32(d, J = 8.2 Hz, 1H), 8.29 (s, 1H).
80.56%	With selenium(IV) dioxide In 1,4-dioxane; lithium hydroxide monohydrate for 3h; Reflux;	2.1.1 2,9-Dicarboxylic acid-1,10-phenanthroline Selenium oxide (13.5 g, 0.12 mol) and 2,9-dimethyl-1,10-phenanthroline (5 g, 0.02 mol) were added into a mixture of1,4-dioxane (320 mL) and ultra-pure water (50 mL) in a500 mL of round-bottom flask. The reaction remained underreflux for 3 h and filtered while hot, then the filtrate was leftto cool. Golden product, 2,9-dicarbaldehyde-1,10-phenanthroline(4.62 g, 80.56%), was obtained after another filtration.Then, 2,9-dicarbaldehyde-1,10-phenanthroline (3 g,0.013 mol) was added into concentrated nitric acid (65%, 60 mL). After refluxing for 3 h, the solution was cooled bypoured onto the solid ice and the crude product was separatedout gradually. The crude product was filtered to get the solidproduct and dried before the next step
80%	With selenium(IV) dioxide In 1,4-dioxane; lithium hydroxide monohydrate for 2h; Reflux;
74%	With selenium(IV) dioxide In 1,4-dioxane Inert atmosphere;
73%	With selenium(IV) dioxide In 1,4-dioxane at 20℃; for 2h; Reflux;
72%	With selenium(IV) dioxide In 1,4-dioxane; lithium hydroxide monohydrate for 0.666667h; Reflux;
72%	With selenium(IV) dioxide In 1,4-dioxane for 0.666667h; Reflux;
72%	With selenium(IV) dioxide In 1,4-dioxane; lithium hydroxide monohydrate for 2h; Reflux;
70%	With selenium(IV) oxide In 1,4-dioxane; lithium hydroxide monohydrate for 2h; Heating;
70%	With selenium(IV) dioxide In 1,4-dioxane; lithium hydroxide monohydrate for 2h; Reflux;
70%	With selenium(IV) dioxide In 1,4-dioxane for 2h; Reflux;
70%	With selenium(IV) dioxide In 1,4-dioxane; lithium hydroxide monohydrate Reflux;
69%	With selenium(IV) dioxide In 1,4-dioxane; lithium hydroxide monohydrate Reflux;	2,9-dicarbaldehyde-1,10-phenanthroline. To a solution of 5.65 g (50.9 mmol) of selenium dioxide in 150 mL dioxane and 10 mL water was addeddropwise a solution of 5.0 g (24.0 mmol) 2,9-dimethyl-1,10-phenanthroline in 100 mL dioxane. Themixture was heated to reflux under magnetic stirring.The disappearance of 2,9-dimethyl-1,10-phenanthrolinewas followed by TLC with dichloromethane/methanol (8/2 v/v) as eluent. Thereaction was stopped when complete disappearance of the reactant was achieved (ca. 4 h).The mixture was filtrated on Celite while hot, the filtrate was allowed to cool and a brownsolid precipitated. It was collected by filtration, washed with dioxane and dried over vacuumto yield a brown solid (3.90 g, 69% yield). The product was engaged in the next step without further purification.
67.1%	With selenium(IV) dioxide In 1,4-dioxane; lithium hydroxide monohydrate for 1h; Reflux;
67.6%	With selenium(IV) dioxide In 1,4-dioxane at 110℃; for 2h;
63%	With selenium(IV) dioxide In dimethyl sulfoxide for 3h; Inert atmosphere; Reflux;
50%	With selenium(IV) oxide; lithium hydroxide monohydrate In 1,4-dioxane for 0.25h; Heating;
48%	With iodine; tert-Butyl iodide; trifluoroacetic acid In dimethyl sulfoxide at 148℃; for 2h;
47%	With selenium(IV) oxide In 1,4-dioxane; lithium hydroxide monohydrate for 2h; Heating;
46.93%	With selenium(IV) dioxide In 1,4-dioxane; lithium hydroxide monohydrate for 2h; Reflux;	2.2.1. 2,9-dicarbaldehyde-1,10-Phenanthroline This compound was prepared according to a literature method [34]with a slight modification. Selenium oxide (1.87 g, 0.05 mol) was addedinto a mixture of 1,4-dioxane (150 mL) and deionized water (10 mL) in a500 mL three necked-flask. After heating to refllux, a solution of 2,9-dimethly-1,10-phenanthroline (1.67 g, 0.024 mol) in 1,4-dioxane(100 mL) was added drop wise into the flask for over 10 min. The reactionwas allowed to run under reflluxf or 2 h then reaction was stoppedand the mixture was filtered while hot, the filtrate was allowed to cool atroom temperature. A yellow needle solid was obtained from filtrate afterfiltration. The solid was used directly for following reaction without anyfurther purification. Yield: 0.890 g, 46.93%. The structure wasconfirmed by 1H NMR.
45%	With selenium(IV) dioxide In 1,4-dioxane; lithium hydroxide monohydrate for 2h; Reflux;
43%	With selenium(IV) dioxide In 1,4-dioxane; lithium hydroxide monohydrate for 3h; Reflux;
34%	With selenium(IV) dioxide In 1,4-dioxane; lithium hydroxide monohydrate Reflux;
	With selenium(IV) oxide In 1,4-dioxane
	With selenium(IV) oxide In 1,4-dioxane for 3h; Heating;
	With selenium(IV) oxide In 1,4-dioxane for 2h; Heating;
	With selenium(IV) dioxide In 1,4-dioxane
	With selenium(IV) dioxide
	With selenium(IV) dioxide In 1,4-dioxane
	With selenium(IV) dioxide
	With selenium(IV) dioxide
	With selenium(IV) dioxide
	With selenium(IV) dioxide In 1,4-dioxane
	With selenium(IV) dioxide In 1,4-dioxane; lithium hydroxide monohydrate for 2.16667h; Reflux;
	With selenium(IV) dioxide In 1,4-dioxane	Synthesis of 1,10-phenanthroline-2,9-dicarboxylic acid bis-[(2-methoxyphenyl)amide] (1) General procedure: The oxidation of 2,9-dimethyl-1,10-phenanthroline with SeO2 in dioxane yielded 1,10-phenanthroline-2,9-dicarboxaldehyde which was further oxidized to 1,10-phenanthroline-2,9-dicarboxylic acid using concentrated HNO3.29 1,10-Phenanthroline-2,9-dicarboxylic acid (0.500 g, 1.86 mmol) was refluxed for two hours in excess SOCl2 (12 ml, 0.168 mol) and a drop of DMF was added in catalytic amount. SOCl2 was then removed at a reduced pressure resulting in diacyl chloride as pale yellow residue to which was added K2CO3 (0.567 g, 4.11 mmol), 2-methoxy aniline (0.506 g,4.11 mmol) and TBAHSO4 in catalytic amount and 25 ml of freshly dry distilled acetonitrile. The contents were refluxed until TLC monitoring indicated completion of the reaction. The contents were filtered and the solvent was vacuum evaporated to yield crude yellow solid. Recrystallization of crude product from mixture of methanol and chloroform resulted in the formation of pure amide.
	With selenium(IV) dioxide In 1,4-dioxane for 4h; Reflux;
	With selenium(IV) oxide
	With selenium(IV) oxide In 1,4-dioxane; lithium hydroxide monohydrate
0.6%	With selenium(IV) dioxide In 1,4-dioxane Heating;
	With selenium(IV) dioxide In 1,4-dioxane for 1h; Heating;
	With selenium(IV) oxide In 1,4-dioxane for 0.5h; Reflux;
	With selenium(IV) dioxide In 1,4-dioxane Reflux;
	With selenium(IV) dioxide In 1,4-dioxane Reflux; Inert atmosphere;
	With selenium(IV) dioxide In 1,4-dioxane
	With selenium(IV) dioxide In 1,4-dioxane for 5h; Reflux;	First step A reaction mixture of 2,9-dimethyl-1,10-phenanthroline hemihydrate (10 mM)and selenium dioxide (10 mM) was placed in 100 mL of dioxane in a 250-mL round bottom(RB) flask. The mixture was manually stirred and allowed to reflux in a wax bath for 5 h. Thehot solution was filtered and a yellow-orange product separated from the filtrate.
	With selenium(IV) dioxide In 1,4-dioxane; lithium hydroxide monohydrate
	With selenium(IV) dioxide In 1,4-dioxane; lithium hydroxide monohydrate at 100℃; for 2h;
	With selenium(IV) dioxide; lithium hydroxide monohydrate In 1,4-dioxane at 80℃;	2.1. Synthesis General procedure: The V-shaped phenanthroline-based hexacatenars in which 1,10-phenanthroline was substituted on 2,9- positions with two cyanovinyl units were prepared according to Scheme 1. 1,10-phenanthroline-2,9-dicarbaldehyde 2[27] was synthesized by oxidationof 2,9-dimethyl-1,10-phenanthroline in the presence of SeO2 in 1,4-dioxane. 4-Hydroxybenzyl cyanide was etherified with benzylchlorides in the presence of K2CO3 in DMF to yield the key intermediate compounds 5/n.[22d,28] Compound 2 was reacted with 5/n under Knoevenagel reaction condition to yield the target compounds Phe/n. All the intermediate compounds and target compounds were purified by column chromatography, the chemical structures were determined by NMR spectra and element alanalysis. The detailed synthetic procedure and corresponding data were described in the ESI. Although some 3,8-disubstituted 1,10-phenanthroline-based polycatenar mesogens had been synthesized using Suzuki and Sonogashira coupling,[12] these Phe/n were the first examples of V-shaped hexacatenars which were synthesized by Knoevenagel reaction in high yields.
	With selenium(IV) dioxide In 1,4-dioxane; lithium hydroxide monohydrate Reflux;
	With selenium(IV) dioxide In 1,4-dioxane at 101.84℃;

Yield	Reaction Conditions	Operation in experiment
50%	With sulfuric acid; nitric acid at 110℃; for 2h;	2 Preparation of 2,9-dimethyl-5-nitro-1,10-phenanthroline 200 mg (1.03 mmol) of 2,9-dimethyl-1,10-phenanthroline was dissolved in 5 ml of concentrated sulfuric acid. 2 ml of fuming nitric acid was slowly added at 110 ° C. and reacted for 2 hours. After the reaction was completed, the pH was adjusted to 10 with saturated sodium hydroxide solution, and the mixture was extracted three times with dichloromethane. The organic layer was washed with saturated sodium hydroxide solution, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressureThe target compound (130 mg, 50%) was obtained.
44%	With sulfuric acid; nitric acid at 120℃; for 1h;
34%	With sulfuric acid; nitric acid at 95℃; for 5h;

30%	With sulfuric acid; nitric acid at 115℃; for 3h;
29%	With sulfuric acid; nitric acid at 125℃; for 0.5h;
23%	With sulfuric acid; nitric acid for 5h; Heating;
18%	With oleum; nitric acid for 0.5h; Reflux;
	With sulfuric acid; sulfur trioxide; nitric acid at 168℃;
	With sulfuric acid; sulfur trioxide; nitric acid at 170℃; for 0.5h;
	With sodium hydroxide; sulfuric acid; nitric acid	Synthesis of FTC-PDA Synthesis of FTC-PDA An acid mixture composed of 5 mL nitric acid (GR (Guaranteed Reagent) grade undiluted solution from Wako Pure Chemical Industries Ltd.) and 10 mL sulfuric acid (GR grade undiluted solution from Wako Pure Chemical Industries Ltd.) was added to 0.5 g of 2,9-dimethyl-1,10-phenanthroline (Wako Pure Chemical Industries Ltd.) and the mixture was heated to 115° C. for 1 hour. To the resulting solution, 100 g of ice was added and the pH of the chilled solution was adjusted to 8.0 by the addition of sodium hydroxide. The resulting precipitate was separated by filtration and dried at 110° C. to give 5-nitro-2,9-dimethyl-1,10-phenanthroline as shown by the formula (B) in .
	With sulfuric acid; nitric acid at 115℃; for 1h;	[0019]Hereinafter, detailed explanation of the present invention through examples,the present invention is not limited thereto. Synthetic nitric acid (manufacturedby Wako Pure Chemical Industries, Ltd. special grade stock solution) 5mL andsulfuric acid (manufactured by Wako Pure Chemical Industries, Ltd. specialgrade stock) of the FTC-PDA mixed acid 10mL has been mixed, represented by theformula shown in FIG. 1 (A) is 2,9-dimethyl-1,10-phenanthroline (manufacturedby Wako Pure Chemical Industries, Ltd.) was added to 0.5 g, it was heated for 1hour at 115 ° C.. 100g of ice was added to the obtained solution, pH of thecooled solution was adjusted to 8.0 with sodium hydroxide. The resultingprecipitate is filtered, dried at 110 , 5-nitro-2,9-dimethyl-1,10-phenanthrolinerepresented by the formula shown in FIG. 1 (B) was obtained.
	In sulfuric acid; water monomer; nitric acid	2.1 (1) (1) Synthesis of 5-nitro-2,9-dimethyl-1,10-phenanthroline (i) 2,9-Dimethyl-1,10-phenanthroline (h) (20 g) was dissolved in a mixture of sulfuric acid (120 ml) and nitric acid (40 ml), and the mixture was heated at 100° C. for 12 hours with stirring. The resulting solution was poured into ice water (300 ml), and the formed precipitate was collected. The precipitate was dissolved in water (500 ml) and neutralized with sodium hydroxide. The resulting precipitate was collected and recrystallized from methanol (300 ml) to give the desired 5-nitro-2,9-dimethyl-1,10-phenanthroline (i) (yield=8.8 g).

[ CAS No. 484-11-7 ] {[proInfo.proName]}

Quality Control of [ 484-11-7 ]

Related Doc. of [ 484-11-7 ]

Product Details of [ 484-11-7 ]

Calculated chemistry of [ 484-11-7 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 484-11-7 ]

Application In Synthesis of [ 484-11-7 ]

[ 484-11-7 ] Synthesis Path-Upstream 1~6

[ 484-11-7 ] Synthesis Path-Downstream 1~87

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

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Inquiry

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: HNO₃, H₂SO₄ 2: 81 percent / NCS, benzoic acid / CCl₄ / 24 h / Heating 3: 85 percent / 98percent H₂SO₄ / 6 h / 80 - 90 °C
	Multi-step reaction with 3 steps 1: nitric acid; sulfuric acid / 1 h / 115 °C 2: selenium(IV) dioxide / 1,4-dioxane; water monomer / 3 h / Reflux 3: nitric acid / 3 h / Reflux
	Multi-step reaction with 3 steps 1: nitric acid; sulfuric acid / 1 h / 120 °C 2: selenium(IV) dioxide / 1,4-dioxane; water monomer / 3 h / Reflux 3: nitric acid; water monomer / 6 h / Reflux

Yield	Reaction Conditions	Operation in experiment
61%	In chloroform; at 20℃; for 0.5h;	In an Erlenmeyer flask equipped with a Teflon-coated magnetic stir bar, <strong>[15709-74-7]tris(triphenylphosphine)copper(I) bromide</strong> (2.61 g, 2.73 mmol) was added to chloroform (50 mL). After complete dissolution, neocuproine (2,9-dimethyl-1,10-phenanthroline (575 mg, 2.76 mmol) was then added. The colorless solution immediately turned yellow-orange. The contents of the flask were allowed to stir for 30 minutes at room temperature. Afterwards the solvent was removed in vacuo to afford a yellow solid. Recrystallization was achieved by layering 80 mL of diethyl ether onto a solution of the solid dissolved in 40 mL of dichloromethane (1.02 g, 61% yield). m.p.: 286-288 C. The cell constants, contents and the space group are identical to that of the already reported structure of Cu(neocup)(PPh3)Br.
61%	In chloroform; at 20℃; for 0.5h;	F. [Cu(neocup)(PPh3)Br]: In an Erlenmeyer flask equipped with a Teflon-coated magnetic stir bar, <strong>[15709-74-7]tris(triphenylphosphine)copper(I) bromide</strong> (2.61 g, 2.73 mmol) was added to chloroform (50 mL). After complete dissolution, neocuproine (2,9-dimethyl-1,10-phenanthroline (575 mg, 2.76 mmol) was then added. The colorless solution immediately turned yellow-orange. The contents of the flask were allowed to stir for 30 minutes at room temperature. Afterwards the solvent was removed in vacuo to afford a yellow solid. Recrystallization was achieved by layering 80 mL of diethyl ether onto a solution of the solid dissolved in 40 mL of dichloromethane (1.02 g, 61% yield). m.p.: 286-288 C. The cell constants, contents and the space group are identical to that of the already reported structure of Cu(neocup)(PPh3)Br.

Yield	Reaction Conditions	Operation in experiment
98%	Stage #1: tetrakis(acetonitrile)copper(I)tetrafluoroborate; bis[2-(diphenylphosphino)phenyl] ether In dichloromethane at 20℃; for 1h; Stage #2: 2.9-dimethyl-1,10-phenanthroline In dichloromethane at 20℃; for 1h;
88%	Stage #1: tetrakis(acetonitrile)copper(I)tetrafluoroborate; bis[2-(diphenylphosphino)phenyl] ether In dichloromethane at 20℃; for 2h; Inert atmosphere; Schlenk technique; Stage #2: 2.9-dimethyl-1,10-phenanthroline In dichloromethane at 20℃; for 2h; Inert atmosphere; Schlenk technique;
82%	Stage #1: tetrakis(acetonitrile)copper(I)tetrafluoroborate; bis[2-(diphenylphosphino)phenyl] ether In dichloromethane at 20℃; for 3h; Stage #2: 2.9-dimethyl-1,10-phenanthroline In dichloromethane for 2h;	A1.1.1. [Cu(phen)(DPEphos)]BF4 (1) General procedure: A mixture of Tetrakis(acetonitrile)copper(I) tetrafluoroborate ([Cu(NCCH3)4]BF4, 3.11 g, 33.0 mmol) and Bis[(2-diphenylphosphino)phenyl]ether (O[C6H4P(C6H5)2]2, DPEphos, 5.33 g, 33.0 mmol) in 300 ml of CH2Cl2 was stirred at room temperature for 3 h. Upon addition of 1,10-Phenanthroline (C12H8N2, phen, 1.78 g, 33.0 mmol) the clear solution turned bright yellow, remained clear, and was stirred for an additional 2 h. Approximately 900 ml of diethyl ether ((CH3CH2)2O) was added to the solution to precipitate a bright yellow solid. The solution containing the newly precipitated solid was then left in the refrigerator for one day. It was vacuum filtered using a medium frit, washed with diethyl ether and dried under vacuum. A bright yellow powder was isolated (yield: 8.00 g, 93 %).

70%	Stage #1: tetrakis(acetonitrile)copper(I)tetrafluoroborate; bis[2-(diphenylphosphino)phenyl] ether In dichloromethane; acetonitrile for 0.5h; Inert atmosphere; Stage #2: 2.9-dimethyl-1,10-phenanthroline In dichloromethane; acetonitrile for 1h; Inert atmosphere;
	In dichloromethane adding C12H6N2(CH3)2 to a soln. of Cu complex and O(C6H4P(C6H5)2)2; pptn. with Et2O;

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