Bathocuproine supplier | CasNO.4733-39-5

Name
Bathocuproine
EINECS 225-240-5
CAS No. 4733-39-5
Article Data3
CAS DataBase
Density 1.173 g/cm³
Solubility Soluble in methanol (36mg/100ml), ethanol, 2-propanol, bezene, and acetone. Partly miscible in water.
Melting Point 279-283 ºC
Formula C₂₆H₂₀N₂
Boiling Point 531.9 ºC at 760 mmHg
Molecular Weight 360.458
Flash Point 231 ºC
Transport Information
Appearance yellow powder
Safety 24/25-36-26
Risk Codes 36/37/38-20/21/22
Molecular Structure
Hazard Symbols Xn
Synonyms 2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline;4,7-Diphenyl-2,9-dimethyl-1,10-phenanthroline;BCP (dye);NSC 89195;
PSA 25.78000
LogP 6.73380

Synthetic route

: 2,9-dimethyl 4,7-dichloro-1,10-phenanthroline

: 98-80-6
phenylboronic acid

: 4733-39-5
Bathocuproine

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 24h; Suzuki-Miyaura Coupling; Reflux; Inert atmosphere;	98%

: 70205-01-5
2-methyl-8-nitro-4-phenyl-quinoline

: 4733-39-5
Bathocuproine

Conditions

Conditions	Yield
Hydrogenation.Erhitzen des erhaltenen Amins mit 1-Phenyl-but-2-en-1-on, sirupoese H3PO4 und H3AsO4;

: 495-41-0
1-phenylbut-2-en-1-one

: 4733-39-5
Bathocuproine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: arsenic acid; zinc-chloride; aqueous hydrochloric acid 2: Hydrogenation.Erhitzen des erhaltenen Amins mit 1-Phenyl-but-2-en-1-on, sirupoese H3PO4 und H3AsO4 View Scheme

: 88-74-4
2-nitro-aniline

: 4733-39-5
Bathocuproine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: arsenic acid; zinc-chloride; aqueous hydrochloric acid 2: Hydrogenation.Erhitzen des erhaltenen Amins mit 1-Phenyl-but-2-en-1-on, sirupoese H3PO4 und H3AsO4 View Scheme

: 95-54-5
1,2-diamino-benzene

: 4733-39-5
Bathocuproine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: 0.25 h / Reflux 1.2: 2 h / Reflux 2.1: diphenylether / 0.67 h / 240 - 260 °C 3.1: trichlorophosphate / 3.5 h / 90 °C / Inert atmosphere 4.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; tetrahydrofuran / 24 h / Reflux; Inert atmosphere View Scheme

: 1311162-31-8
5,5'-((1,2-phenylenebis(azanediyl))bis(ethan-1-yl-1-ylidene))bis(2,2-dimethyl-1,3-dioxane-4,6-dione)

: 4733-39-5
Bathocuproine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: diphenylether / 0.67 h / 240 - 260 °C 2: trichlorophosphate / 3.5 h / 90 °C / Inert atmosphere 3: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; tetrahydrofuran / 24 h / Reflux; Inert atmosphere View Scheme

: C37H25MnN6O4

A: 201230-82-2
carbon monoxide

B: 4733-39-5
Bathocuproine

C: 74815-22-8
4-(1H-1,2,3,4-tetrazol-5-yl)benzaldehyde

Conditions

Conditions	Yield
In dichloromethane UV-irradiation;

...Expand

: C36H25MnN6O3

A: 18039-42-4
5-Phenyl-1H-tetrazole

B: 201230-82-2
carbon monoxide

C: 4733-39-5
Bathocuproine

Conditions

Conditions	Yield
In dichloromethane UV-irradiation;

...Expand

: C35H24MnN7O3

A: 3250-74-6
3-(1H-tetrazol-5-yl)pyridine

B: 201230-82-2
carbon monoxide

C: 4733-39-5
Bathocuproine

Conditions

Conditions	Yield
In dichloromethane UV-irradiation;

...Expand

: C35H24MnN7O3

A: 14389-12-9
5-(4-pyridyl)tetrazole

B: 201230-82-2
carbon monoxide

C: 4733-39-5
Bathocuproine

Conditions

Conditions	Yield
In dichloromethane UV-irradiation;

...Expand

: C37H24MnN7O3

A: 14389-10-7
5-(4-cyanophenyl)tetrazole

B: 201230-82-2
carbon monoxide

C: 4733-39-5
Bathocuproine

Conditions

Conditions	Yield
In dichloromethane UV-irradiation;

...Expand

: 64443-05-6
tetrakis(actonitrile)copper(I) hexafluorophosphate

: 4733-39-5
Bathocuproine

: 166330-10-5
bis[2-(diphenylphosphino)phenyl] ether

: 1421057-27-3
2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline bis[(2-diphenyl-phosphino)phenyl]ether copper(I) hexafluorophosphate

Conditions

Conditions	Yield
Stage #1: tetrakis(actonitrile)copper(I) hexafluorophosphate; bis[2-(diphenylphosphino)phenyl] ether In dichloromethane at 20℃; for 2h; Inert atmosphere; Stage #2: Bathocuproine In dichloromethane for 1h; Inert atmosphere;	99%
Stage #1: tetrakis(actonitrile)copper(I) hexafluorophosphate; bis[2-(diphenylphosphino)phenyl] ether In dichloromethane at 20℃; for 2h; Inert atmosphere; Stage #2: Bathocuproine In dichloromethane for 1h;	91%
Stage #1: tetrakis(actonitrile)copper(I) hexafluorophosphate; bis[2-(diphenylphosphino)phenyl] ether In dichloromethane Schlenk technique; Reflux; Stage #2: Bathocuproine In dichloromethane at 20℃; Schlenk technique; Reflux;	85%
Stage #1: tetrakis(actonitrile)copper(I) hexafluorophosphate; bis[2-(diphenylphosphino)phenyl] ether In dichloromethane at 20℃; for 2h; Stage #2: Bathocuproine In dichloromethane at 20℃; for 1h;	43.8%
Stage #1: tetrakis(actonitrile)copper(I) hexafluorophosphate; bis[2-(diphenylphosphino)phenyl] ether In dichloromethane at 20℃; Stage #2: Bathocuproine In dichloromethane at 20℃;

...Expand

: 64443-05-6
tetrakis(actonitrile)copper(I) hexafluorophosphate

: 4733-39-5
Bathocuproine

: nixantphos

: 1421057-56-8
[Cu(bathocuproine)(4,6-bis(diphenylphosphino)-10H-phenoxazine)]PF6

Conditions

Conditions	Yield
Stage #1: tetrakis(actonitrile)copper(I) hexafluorophosphate; nixantphos In dichloromethane Schlenk technique; Reflux; Stage #2: Bathocuproine In dichloromethane at 20℃; Schlenk technique; Reflux;	99%
Stage #1: tetrakis(actonitrile)copper(I) hexafluorophosphate; nixantphos In dichloromethane at 20℃; Stage #2: Bathocuproine In dichloromethane at 20℃;

...Expand

: 4733-39-5
Bathocuproine

: 3375-31-3
palladium diacetate

: 152506-88-2
(2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline)palladium(II) acetate

Conditions

Conditions	Yield
With air In dichloromethane at 20℃;	98%
In dichloromethane pptn. from diethyl ether;	96%
In dichloromethane at 30℃; for 3h; Inert atmosphere;	96%

: 120763-13-5
NiCl2(bathocuproine)

: 4733-39-5
Bathocuproine

: C52H40N4Ni(1+)*Cl(1-)

Conditions

Conditions	Yield
With cyclohexa-1,4-diene In acetonitrile Irradiation; Photolysis; Inert atmosphere; Glovebox;	98%

: [(η5-4,7-Me2C9H5)Mo(CO)2(NCMe)2][BF4]

: 4733-39-5
Bathocuproine

: [(η5-4,7-Me2C9H5)-Mo(CO)2(2,9-Me2-4,7-Ph2-phen)][BF4]

Conditions

Conditions	Yield
In dichloromethane at 20℃; Inert atmosphere; Schlenk technique;	98%

: ammonium hexafluorophosphate

: 14099-01-5
rhenium(I) pentacarbonyl chloride

: 119072-54-7, 2769-71-3
2,6-dimethylphenyl isonitrile

: 4733-39-5
Bathocuproine

: 850813-85-3
fac-[Re(CO)3(2,6-dimethylphenylisocyanide)(2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline)](PF6)

Conditions

Conditions	Yield
With AgCF3SO3 In ethanol byproducts: AgCl; addn. of Re(CO)5Cl to Me2Ph2-phen, addn. EtOH, reflux for 2 h; pptn., filtration at room temp., drying (vac.) for 3 h; addn. of AgCF3SO3 and EtOH, reflux for 4 h; cooling, pptn., filtration, addn. Me2C6H3NC/EtOH; reflux for 3 h; concn., addn. aq. NH4PF6; dilution with water, pptn., filtration, drying in vac. oven, elem. anal.;	97%

...Expand

: 29046-78-4
(1,2-dimethoxyethane)dichloronickel(II)

: 4733-39-5
Bathocuproine

: 120763-13-5
NiCl2(bathocuproine)

Conditions

Conditions	Yield
In tetrahydrofuran at 23℃; for 10h; Inert atmosphere; Glovebox;	96%

: 4733-39-5
Bathocuproine

: 3375-31-3
palladium diacetate

: (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline)-palladium(II) acetate

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 3h;	96%

: (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(dicyclohexylphosphane)

: 64443-05-6
tetrakis(actonitrile)copper(I) hexafluorophosphate

: 4733-39-5
Bathocuproine

: 1421057-52-4
[Cu(bathocuproine)((9,9-dimethyl-9H-xanthene-4,5-diyl)bis(dicyclohexylphosphine))]PF6

Conditions

Conditions	Yield
Stage #1: (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(dicyclohexylphosphane); tetrakis(actonitrile)copper(I) hexafluorophosphate In dichloromethane Schlenk technique; Reflux; Stage #2: Bathocuproine In dichloromethane at 20℃; Schlenk technique; Reflux;	95%

...Expand

: 4733-39-5
Bathocuproine

: 4,7-diphenyl-1,10-phenanthroline-2,9-dicarboxylic acid

Conditions

Conditions	Yield
Stage #1: Bathocuproine With selenium(IV) oxide In 1,4-dioxane; water for 3h; Reflux; Stage #2: With nitric acid for 3h; Reflux;	94%
With dihydrogen peroxide at 80℃; for 8h;	80%
Multi-step reaction with 2 steps 1: 76 percent / N-chlorosuccinimide, 3-chloroperbenzoic acid / CCl4; CHCl3 / 16 h / Heating 2: 89 percent / aq. formic acid / 24 h / Heating View Scheme
Multi-step reaction with 2 steps 1: N-chloro-succinimide; dibenzoyl peroxide / chloroform / 6 h / Reflux 2: sulfuric acid / 2 h / Microwave irradiation; Heating View Scheme

: 64443-05-6
tetrakis(actonitrile)copper(I) hexafluorophosphate

: 4733-39-5
Bathocuproine

: 47895-81-8
bis(2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline)copper(I) hexafluorophosphate

Conditions

Conditions	Yield
In acetonitrile Ar-atmosphere; addn. of 2 equiv. of phen derivative to Cu-complex soln.,stirring for 10 min; pptn. on Et2O addn., filtration, dissoln. in CH2Cl2, crystn. on layeringwith Et2O; elem. anal.;	94%
In methanol for 1h; Inert atmosphere;	82%
for 0.333333h; Inert atmosphere;

: 120763-13-5
NiCl2(bathocuproine)

: 4733-39-5
Bathocuproine

: 1508299-90-8
Ni(bathocuproine)2

Conditions

Conditions	Yield
With 2,6-dimethylpyridine In tetrahydrofuran Irradiation; Inert atmosphere; Glovebox;	94%

: 4733-39-5
Bathocuproine

: 2,9-bis(trichloromethyl)-4,7-diphenyl-1,10-phenanthroline

Conditions

Conditions	Yield
With N-chloro-succinimide; dibenzoyl peroxide In chloroform for 6h; Reflux;	93%
With N-chloro-succinimide; dibenzoyl peroxide In chloroform for 24h; Reflux;	80%
With N-chloro-succinimide; 3-chloro-benzenecarboperoxoic acid In tetrachloromethane; chloroform for 16h; Heating;	76%
With N-chloro-succinimide; dibenzoyl peroxide In tetrachloromethane; chloroform	6.1 g (97%)

: 4733-39-5
Bathocuproine

: 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline N-oxide

Conditions

Conditions	Yield
With water; fluorine; acetonitrile In chloroform at 0℃;	93%

: 64443-05-6
tetrakis(actonitrile)copper(I) hexafluorophosphate

: 4733-39-5
Bathocuproine

: 161265-03-8
4,5-bis(diphenylphosphino)-9,9-dimethylxanthene

: 1421057-42-2
[Cu(2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline)(4,5-bis(diphenylphosphino)-9,9-dimethylxanthene)](PF6)

Conditions

Conditions	Yield
Stage #1: tetrakis(actonitrile)copper(I) hexafluorophosphate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In dichloromethane Schlenk technique; Reflux; Stage #2: Bathocuproine In dichloromethane at 20℃; Schlenk technique; Reflux;	93%
Stage #1: tetrakis(actonitrile)copper(I) hexafluorophosphate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In dichloromethane Inert atmosphere; Schlenk technique; Reflux; Stage #2: Bathocuproine In dichloromethane Inert atmosphere; Schlenk technique; Reflux;	93%
Stage #1: tetrakis(actonitrile)copper(I) hexafluorophosphate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In dichloromethane at 20℃; Stage #2: Bathocuproine In dichloromethane at 20℃;
Stage #1: tetrakis(actonitrile)copper(I) hexafluorophosphate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In dichloromethane Inert atmosphere; Reflux; Stage #2: Bathocuproine In dichloromethane for 3h; Inert atmosphere; Reflux;

...Expand

: 1295-35-8
bis(1,5-cyclooctadiene)nickel (0)

: 4733-39-5
Bathocuproine

: 1508299-90-8
Ni(bathocuproine)2

Conditions

Conditions	Yield
In tetrahydrofuran at 60℃; for 12h; Inert atmosphere; Glovebox;	93%

: 64443-05-6
tetrakis(actonitrile)copper(I) hexafluorophosphate

: 119072-54-7, 2769-71-3
2,6-dimethylphenyl isonitrile

: 4733-39-5
Bathocuproine

: [Cu(2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline)(2,6-dimethylphenylisocyanide)2]PF6

Conditions

Conditions	Yield
In dichloromethane for 1h;	93%

...Expand

: C34H36CuN4(1+)*F6P(1-)

: 4733-39-5
Bathocuproine

: (2,9-dimesityl-1,10-phenanthroline)(bathocuproine)copper(I) hexafluorophosphate

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 0.5h;	91%

: 4733-39-5
Bathocuproine

: 4-methyl-N-(2-(7-phenylindolo[1,2-a]quinazolin-9-yl)phenyl)benzenesulfonamide

: 7-phenyl-13-tosyl-13H-quinazolino[1',2':1,5]pyrrolo[2,3-b]carbazole

Conditions

Conditions	Yield
With sodium acetate; palladium diacetate In 1,3,5-trimethyl-benzene at 100℃; for 6h;	91%

: 64443-05-6
tetrakis(actonitrile)copper(I) hexafluorophosphate

: 2,2′-bis(diphenylphosphino)-1,1′-binaphthalene.

: 4733-39-5
Bathocuproine

: [Cu(bathocuproine)(binap)]PF6

Conditions

Conditions	Yield
Stage #1: tetrakis(actonitrile)copper(I) hexafluorophosphate; 2,2′-bis(diphenylphosphino)-1,1′-binaphthalene. In dichloromethane Schlenk technique; Reflux; Stage #2: Bathocuproine In dichloromethane at 20℃; Schlenk technique; Reflux;	90%

...Expand

: 4733-39-5
Bathocuproine

: 7787-70-4
copper(I) bromide

: (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline)CuBr

Conditions

Conditions	Yield
In acetonitrile at 20℃; Inert atmosphere;	90%

: 67969-82-8
tetrafluoroboric acid diethyl ether

: 4733-39-5
Bathocuproine

: [(Bathocuproine)H2](BF4)2

Conditions

Conditions	Yield
In acetone for 0.583333h;	90%

: nickel(II) bromide diethylene glycol dimethyl ether

: 4733-39-5
Bathocuproine

: 326822-02-0
(2,9-dimethyl-4,7-diphenyl-1,10-phenantroline)NiBr2

Conditions

Conditions	Yield
In tetrahydrofuran at 20℃; for 46h; Inert atmosphere; Sealed tube;	90%

: silver hexafluoroantimonate

: 4733-39-5
Bathocuproine

: C52H40AgN4(1+)*F6Sb(1-)

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 16h; Inert atmosphere; Glovebox; Schlenk technique;	90%

: copper(II) nitrate trihydrate

: 4733-39-5
Bathocuproine

: C52H40CuN4(2+)*2NO3(1-)

Conditions

Conditions	Yield
In dichloromethane; acetone	90%

: 59-48-3
2-oxoindole

: 4733-39-5
Bathocuproine

: 3-hydroxy-3-((9-methyl-4,7-diphenyl-1,10-phenanthrolin-2-yl)methyl)indolin-2-one

Conditions

Conditions	Yield
With iron(II) acetate In N,N-dimethyl-formamide at 80℃; for 5h; Green chemistry;	90%

: 17084-13-8
potassium hexafluorophosphate

: cis-bis-(2,2′-bipyridine) dichlororuthenium(II) dihydrate

: 4733-39-5
Bathocuproine

: [Ru(bpy)2(2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline)](PF6)2

Conditions

Conditions	Yield
Stage #1: cis-bis-(2,2′-bipyridine) dichlororuthenium(II) dihydrate; Bathocuproine In 1,2-dimethoxyethane at 260℃; for 6h; Stage #2: potassium hexafluorophosphate In water	89%

...Expand

: 4733-39-5
Bathocuproine

: 2,9-dicarboxaldehyde-4,7-diphenyl-1,10-phenanthroline

Conditions

Conditions	Yield
With selenium(IV) oxide In 1,4-dioxane; water at 110℃; for 2h;	88%
With selenium(IV) oxide In 1,4-dioxane at 80℃; for 2h; Inert atmosphere; Sealed tube;	85%

: tetrakis(acetonitrile)copper(I)tetrafluoroborate

: 4733-39-5
Bathocuproine

: 5112-95-8
bis(diphenylphosphino)acetylene

: [Cu2(2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline)2(μ-bis(diphenylphosphino)acetylene)2](BF4)2

Conditions

Conditions	Yield
Stage #1: tetrakis(acetonitrile)copper(I)tetrafluoroborate; bis(diphenylphosphino)acetylene In dichloromethane; acetonitrile for 0.5h; Inert atmosphere; Stage #2: Bathocuproine In dichloromethane; acetonitrile for 1h; Inert atmosphere;	88%

...Expand

Bathocuproine Specification

The Bathocuproine, with the CAS registry number 4733-39-5, is also known as 4,7-Diphenyl-2,9-dimethyl-1,10-phenanthroline. It belongs to the classification codes of Antioxidants; Free Radical Scavengers; Indicators and Reagents. Its EINECS registry number is 225-240-5. This chemical's molecular formula is C₂₆H₂₀N₂ and molecular weight is 360.45. What's more, both its IUPAC name and systematic name are the same which is called 2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline. It should be kept in a ventilated and dry place and it is a derivative of phenanthroline.

Physical properties about Bathocuproine are: (1)ACD/LogP: 6.22; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 5.61; (4)ACD/LogD (pH 7.4): 6.2; (5)ACD/BCF (pH 5.5): 7684.69; (6)ACD/BCF (pH 7.4): 29980.94; (7)ACD/KOC (pH 5.5): 14131.75; (8)ACD/KOC (pH 7.4): 55133.37; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 2; (12) Polar Surface Area: 25.78 Å²; (13)Index of Refraction: 1.686; (14) MolarRefractivity: 116.95 cm³; (15)Molar Volume: 307.2 cm³; (16)Surface Tension: 52 dyne/cm; (17)Density: 1.173 g/cm³; (18)Flash Point: 231 °C; (19)Enthalpy of Vaporization: 77.71 kJ/mol; (20)Boiling Point: 531.9 °C at 760 mmHg; (21)Vapour Pressure: 7.38E-11 mmHg at 25 °C.

Uses of Bathocuproine: it is used to produce other chemicals. For example, it can produce 4,7-Diphenyl-2,9-bis-trichloromethyl-[1,10]phenanthroline. This reaction needs reagents N-chlorosuccinimide, 3-chloroperbenzoic acid, solvents CCl₄, CHCl₃ and other condition of heating for 16 hours. The yield is 76 %.

When you are dealing with this chemical, you should be very careful. This chemical is inflammation to the skin, eyes and respiratory system and may cause damage to health by inhalation, in contacting with skin and if swallowed. Therefore, you should wear suitable protective clothing and avoid contacting with skin, eyes. And in case of contacting with eyes, you should rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1) SMILES: n2c4c(c(c1ccccc1)cc2C)ccc3c(cc(nc34)C)c5ccccc5
(2) InChI: InChI=1S/C26H20N2/c1-17-15-23(19-9-5-3-6-10-19)21-13-14-22-24(20-11-7-4-8-12-20)16-18(2)28-26(22)25(21)27-17/h3-16H,1-2H3
(3) InChIKey: STTGYIUESPWXOW-UHFFFAOYSA-N

Product Name

Bathocuproine

Synthetic route

Bathocuproine Specification

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