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| CAS No.: | 484-11-7 |
|---|---|
| Name: | Neocuproine |
| Article Data: | 16 |
| Molecular Structure: | |
|
|
|
| Formula: | C14H12N2 |
| Molecular Weight: | 208.263 |
| 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-; |
| EINECS: | 207-601-9 |
| Density: | 1.178 g/cm3 |
| Melting Point: | 159-164 °C |
| Boiling Point: | 367.4 °C at 760 mmHg |
| Flash Point: | 159.7 °C |
| Solubility: | slightly soluble in water |
| Appearance: | off-white to very pale yellow crystalline powder |
| Hazard Symbols: |
 Xi,  Xn
|
| Risk Codes: | 36/37/38-20/21/22-22 |
| Safety: | 26-36/37/39-36-24/25 |
| PSA: | 25.78000 |
| LogP: | 3.39980 |
- 5156-58-1N-(1-Benzyl-4-pipperidinyl)-N-phenylpropanamide HCl
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- 50288-62-5threo-Phenyl-2-piperidyl acetamide
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| Conditions | Yield |
|---|---|
| With potassium hydroxide In ethanol at 80℃; for 8h; Schlenk technique; | 79% |
| 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 | 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 | 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% |
A
- 484-11-7
2.9-dimethyl-1,10-phenanthroline
| Conditions | Yield |
|---|---|
| In cyclohexane for 48h; Irradiation; | A n/a B 30% C n/a |
- 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 | 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 | 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; |
- 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 | 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; |
| Conditions | Yield |
|---|---|
| for 6h; Irradiation; |
| 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 |
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Chemistry
Molecular Structure of Neocuproine (CAS NO.484-11-7):
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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
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.
Safety Profile
Safety Information of Neocuproine (CAS NO.484-11-7):
Hazard Codes: 
Xi,
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
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- .