Neocuproine supplier | CasNO.484-11-7

Name
Neocuproine
EINECS 207-601-9
CAS No. 484-11-7
Article Data16
CAS DataBase
Density 1.178 g/cm³
Solubility slightly soluble in water
Melting Point 159-164 °C
Formula C₁₄H₁₂N₂
Boiling Point 367.4 °C at 760 mmHg
Molecular Weight 208.263
Flash Point 159.7 °C
Transport Information
Appearance off-white to very pale yellow crystalline powder
Safety 26-36/37/39-36-24/25
Risk Codes 36/37/38-20/21/22-22
Molecular Structure
Hazard Symbols Xi, Xn
Synonyms 2,9-Dimethyl-1,10-phenanthroline;2,9-Dimethyl-o-phenanthroline;2,9-Dimethylphenanthroline;2,9-Neocuproine;NSC 4280;Neocuproin;VUF 7738;1,10-Phenanthroline,2,9-dimethyl-;
PSA 25.78000
LogP 3.39980

Synthetic route

: 2,3-diaminobenzene-1,4-dicarbaldehyde

: 67-64-1
acetone

: 484-11-7
2.9-dimethyl-1,10-phenanthroline

Conditions

Conditions	Yield
With potassium hydroxide In ethanol at 80℃; for 8h; Schlenk technique;	79%

: 2,3-dinitrobenzene-1,4-dicarbaldehyde

: 67-64-1
acetone

: 484-11-7
2.9-dimethyl-1,10-phenanthroline

Conditions

Conditions	Yield
With potassium hydroxide In ethanol for 8h; Sealed tube; Reflux;	64%

: 942267-04-1
C14H12Br2N2

: 484-11-7
2.9-dimethyl-1,10-phenanthroline

Conditions

Conditions	Yield
With copper In 1-methyl-pyrrolidin-2-one for 30h; Ullmann coupling; Heating;	59%

: 18978-78-4
2-methyl-8-aminoquinoline

: 75-07-0
acetaldehyde

: 109-92-2
ethyl vinyl ether

: 484-11-7
2.9-dimethyl-1,10-phenanthroline

Conditions

Conditions	Yield
Stage #1: 2-methyl-8-aminoquinoline; acetaldehyde; ethyl vinyl ether In 2,2,2-trifluoroethanol at 30℃; Diels-Alder reaction; Stage #2: With hydrogenchloride; oxygen In water; acetonitrile under 760.051 Torr; for 16h;	42%

...Expand

: (E)-1,2-bis-(4-methyl-3-pyridyl)ethene

A: 484-11-7
2.9-dimethyl-1,10-phenanthroline

B: 2,9-dimethyl-3,8-diazaphenanthrene

C: 2,9-dimethyl-1,8-diazaphenanthrene

Conditions

Conditions	Yield
In cyclohexane for 48h; Irradiation;	A n/a B 30% C n/a

...Expand

: 18978-78-4
2-methyl-8-aminoquinoline

: 78267-54-6, 5860-35-5
1,1-diacetoxy-but-2-ene

: 484-11-7
2.9-dimethyl-1,10-phenanthroline

Conditions

Conditions	Yield
With arsenic(V) oxide; sulfuric acid

: 66-71-7
1,10-Phenanthroline

: 917-54-4
methyllithium

A: 3002-77-5
2-methyl-1,10-phenanthroline

B: 484-11-7
2.9-dimethyl-1,10-phenanthroline

Conditions

Conditions	Yield
With manganese(IV) oxide; water Multistep reaction. Title compound not separated from byproducts;
With potassium permanganate 1.) ether/THF, 2 h, 0-10 deg C, 2 eq. MeLi; 2.) acetone; Yield given. Multistep reaction. Yields of byproduct given;

...Expand

: 21710-12-3
bis(2,9-dimethyl-1,10-phenathroline) copper(I)

: 90030-13-0
((C2H4O)2C6H4)NC5H2C2H2C5H2N(C6H4(C2H4O)2)OC2H4O

A: 484-11-7
2.9-dimethyl-1,10-phenanthroline

B: 88503-31-5
Cu(C34H34N2O6)2(1+)

Conditions

Conditions	Yield
In not given large excess of Cu(dmp)2(1+), than the equilibrium is totally shifted to the right; visible spectra of reaction solution;

...Expand

: bis(2,2'-dipyridyl)-2,9-dimethyl-o-phenantrolineruthenium(II) hexafluorophosphate

A: 366-18-7
[2,2]bipyridinyl

B: 484-11-7
2.9-dimethyl-1,10-phenanthroline

Conditions

Conditions	Yield
for 6h; Irradiation;

: 711-41-1
2,3-dinitro-p-xylene

: 484-11-7
2.9-dimethyl-1,10-phenanthroline

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: N,N-dimethyl-formamide / 140 °C / Inert atmosphere 2: sodium periodate / water; tetrahydrofuran / 24 h / 0 °C 3: iron; hydrogenchloride / ethanol; water; ethyl acetate / 3 h / Reflux 4: potassium hydroxide / ethanol / 8 h / 80 °C / Schlenk technique View Scheme

: 113397-69-6
(1E,1'E)-2,2'-(2,3-dinitro-1,4-phenylene)bis(N,N-dimethylethen-1-amine)

: 484-11-7
2.9-dimethyl-1,10-phenanthroline

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium periodate / water; tetrahydrofuran / 24 h / 0 °C 2: iron; hydrogenchloride / ethanol; water; ethyl acetate / 3 h / Reflux 3: potassium hydroxide / ethanol / 8 h / 80 °C / Schlenk technique View Scheme
Multi-step reaction with 2 steps 1: sodium periodate / tetrahydrofuran; water / 24 h / 0 °C 2: potassium hydroxide / ethanol / 8 h / Sealed tube; Reflux View Scheme

: 2,3-dinitrobenzene-1,4-dicarbaldehyde

: 484-11-7
2.9-dimethyl-1,10-phenanthroline

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: iron; hydrogenchloride / ethanol; water; ethyl acetate / 3 h / Reflux 2: potassium hydroxide / ethanol / 8 h / 80 °C / Schlenk technique View Scheme

: 484-11-7
2.9-dimethyl-1,10-phenanthroline

: 255047-70-2
2,9-dimethyl-1,10-phenanthroline N-oxide

Conditions

Conditions	Yield
With dihydrogen peroxide; acetic acid In water for 3.5h; Oxidation; Heating;	100%
With dihydrogen peroxide; acetic acid at 65℃; for 4.5h;	68%

: 484-11-7
2.9-dimethyl-1,10-phenanthroline

: 12146-37-1, 124717-04-0
(bicyclo[2.2.1]hepta-2,5-diene)tetracarbonylmolybdenum(0)

A: 23301-98-6
molybdenum(0) tetracarbonyl(2,9-dimethyl-1,10-phenanthroline)

B: 121-46-0
bicyclo[2.2.1]hepta-2,5-diene

Conditions

Conditions	Yield
In tetrahydrofuran reaction in a calorimeter under argon;	A 100% B n/a

...Expand

: 484-11-7
2.9-dimethyl-1,10-phenanthroline

: 50671-60-8
copper n-butyrate

: (neocuproine)2CuO2CCH2CH2CH3

Conditions

Conditions	Yield
In benzene inert atmosphere; stirring for 6 d (room temp.) (pptn.); filtering off, washing with Et2O, drying (vac.); elem. anal.;	99.7%

: 484-11-7
2.9-dimethyl-1,10-phenanthroline

: 78831-41-1
2,9-Bis(trichloromethyl)-1,10-phenanthroline

Conditions

Conditions	Yield
With N-chloro-succinimide; dibenzoyl peroxide In chloroform for 72h; Reflux;	99%
With N-chloro-succinimide; triphenylphosphine In tetrachloromethane at 80 - 85℃; for 7h;	95%
With N-chloro-succinimide In chloroform for 6h; Heating;	90%

: 484-11-7
2.9-dimethyl-1,10-phenanthroline

: [Ag(N3)(P(C6H5)3)2]2

: 385825-49-0
Ag(I)(N3)(PPh3)(2,9-dimethyl-1,10-phenanthroline) complex

Conditions

Conditions	Yield
In diethyl ether under N2; Schlenk techniques; soln./suspn. of 2,9-dimethyl-1,10-phenanthroline added to soln. of Ag(N3)(PPh3)2 at 273 K; stirred overnight at room temp.; ligand-to-metal molar ratio of 4:1; filtered off; ppt. washed with diethyl ether-ethanol (3:1); recrystd. from acetonitrile-diethyl ether (1:1); elem.anal.;	99%

: copper(II) nitrate trihydrate

: 484-11-7
2.9-dimethyl-1,10-phenanthroline

: 1934-75-4
sodium dicyanamide

: 758716-17-5
[Cu2(2,9-dimethyl-1,10-phenanthroline)2(dicyanamide)4]

Conditions

Conditions	Yield
In water addn. of aq. soln. of NaN(CN)2 to aq. soln. of Cu(NO3)2*3H2O and 2,9-dimethyl-1,10-phenanthroline; crystn., elem. anal.;	99%

...Expand

: tetrakis(acetonitrile)copper(I)tetrafluoroborate

: 484-11-7
2.9-dimethyl-1,10-phenanthroline

: 733-60-8
tetramethylammonium picrate

: 87045-32-7
bis(2,9-dimethyl-1,10-phenanthroline)copper(I) picrate

Conditions

Conditions	Yield
In water; acetonitrile Cu complex and stoich. amt. of ligand dissolved in MeCN-H2O; picrate (10% excess) added; refluxed for 2 h; crystd. by slow evapn.;	99%

...Expand

Neocuproine Chemical Properties

Molecular Structure of Neocuproine (CAS NO.484-11-7):

IUPAC Name: 2,9-Dimethyl-1,10-phenanthroline
Canonical SMILES: CC1=NC2=C(C=C1)C=CC3=C2N=C(C=C3)C
InChI: InChI=1S/C14H12N2/c1-9-3-5-11-7-8-12-6-4-10(2)16-14(12)13(11)15-9/h3-8H,1-2H3
InChIKey: IYRGXJIJGHOCFS-UHFFFAOYSA-N
Molecular Weight: 208.25848 [g/mol]
Molecular Formula: C₁₄H₁₂N₂
XLogP3-AA: 3.3
H-Bond Donor: 0
H-Bond Acceptor: 2
EINECS: 207-601-9
Index of Refraction: 1.693
Molar Refractivity: 67.77 cm³
Molar Volume: 176.6 cm³
Surface Tension: 53.8 dyne/cm
Density: 1.178 g/cm³
Flash Point: 159.7 °C
Enthalpy of Vaporization: 58.98 kJ/mol
Boiling Point: 367.4 °C at 760 mmHg
Vapour Pressure: 2.89E-05 mmHg at 25 °C
Appearance: Pale Yellow-Off White Crystals
Melting Point: 159-164 °C
solubility: methanol: 0.1 g/mL, clear
Water Solubility: slightly soluble
Classification Code: Antineoplastic agents; Chelating agents
Product Categories: Analytical Chemistry; Chelating Reagents; Phenanthrolines

Neocuproine Uses

In the early 1930s, phenanthroline derivatives became known for their use in colorimetric indicators for many transition metals. Neocuproine (CAS NO.484-11-7) proved to be highly selective for chelation to copper(I). The resulting complex, Cu(neocuproine)2+ has a deep orange-red color. In addition to direct mixture of neocuproine to copper solutions, effects of neocuproine on biochemical systems dependent on copper(I) have been commonly conducted.

Neocuproine Safety Profile

Safety Information of Neocuproine (CAS NO.484-11-7):
Hazard Codes: Irritant Xi, Harmful Xn
Risk Statements: 36/37/38-20/21/22-22
R36/37/38:Irritating to eyes, respiratory system and skin.
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
R22:Harmful if swallowed.
Safety Statements: 26-36/37/39-36-24/25
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
S36:Wear suitable protective clothing.
S24/25:Avoid contact with skin and eyes.
WGK Germany: 3

Neocuproine Specification

Neocuproine (CAS NO.484-11-7), its Synonyms are 2,9-Dimethyl-1,10-phenanthroline ; 2,9-Dimethylphenanthroline ; Neocuproin ; 1,10-Phenanthroline, 2,9-dimethyl- .

Product Name

Neocuproine

Synthetic route

Neocuproine Chemical Properties

Neocuproine Uses

Neocuproine Safety Profile

Neocuproine Specification

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