2,9-Dimethyl-1,10-phenanthroline

HCID 65237CAS 484-11-7
Substructure searchFind similar structures

Basic information

Standard SMILES
Cc1ccc2ccc3ccc(C)nc3c2n1
InChIKey
IYRGXJIJGHOCFS-UHFFFAOYSA-N
Molecular formula
C14H12N2
Average molar mass
208.26 g/mol
Monoisotopic mass
208.10004839

Names & identifiers

Preferred name
2,9-Dimethyl-1,10-phenanthroline
IUPAC
2,9-dimethyl-1,10-phenanthroline
English name
Neocuproine
Molecular formula
C14H12N2
Molecular weight
208.26

Names & synonyms

Neocuproine2,9-Dimethyl-1,10-phenanthroline484-11-7Neocuproin1,10-Phenanthroline, 2,9-dimethyl-2,9-DimethylphenanthrolineDMPHEN2,9-Dimethyl-o-phenanthroline8E7D2SH3BVDTXSID5060065NSC-4280VUF-7738
Show more names
Mephen2,9-dimethyl-10-phenanthrolineVUF 7738Cuproin,neo
CHEBI:912223,6-dimethyl-4,5-phenanthrolineRefChem:165152DTXCID1040619207-601-9neo-CuproinNSC4280MFCD00004973

Database identifiers

CAS
484-11-7、7296-20-0
PubChem CID
65237
DTXSID
DTXSID5060065
ChEMBL
CHEMBL375781
ChEBI
CHEBI:91222
UNII
8E7D2SH3BV
EC Number
207-601-9、230-732-8
Nikkaji
J5.993E

Properties

Computed structural properties

XLogP
3.3
Topological polar surface area
25.8 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
0
Heavy atoms
16

Experimental & physicochemical properties

Physical DescriptionBeige crystalline solid; [Sigma-Aldrich MSDS]

Physicochemical properties

Melting point
159 · 159-164 °C
Boiling point
337.46 °C · 337.46°C (rough estimate)
Density
1.1345 · 1.1345 (rough estimate)
bulk density
280 kg/m3 · 280kg/m3
refractive index
1.6152 · 1.6152 (estimate)
RTECS
8380000 · SF8380000

Safety & regulation

GHS classification

GHS Classification · 6 items

This chemical does not meet GHS hazard criteria for 2.1% (1 of 47) of reports.

Warning

H315 (97.9%): Causes skin irritation [Warning Skin corrosion/irritation]；H319 (93.6%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H335 (95.7%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 47 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Reported as not meeting GHS hazard criteria per 1 of 47 reports by companies.；There are 8 notifications provided by 46 of 47 reports by companies with hazard statement code(s).；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Regulatory Information · 2 items

Chemical: 1,10-Phenanthroline, 2,9-dimethyl-

1,10-Phenanthroline, 2,9-dimethyl-: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryA skin and strong eye irritant; [Sigma-Aldrich MSDS] See POLYCYCLIC AROMATIC HYDROCARBONS.
Hazard Classes and Categories · 2 items

Skin Irrit. 2 (100%)；Eye Irrit. 2 (100%)；STOT SE 3 (80%)

Skin Irrit. 2 (97.9%)；Eye Irrit. 2A (93.6%)；STOT SE 3 (95.7%)

Regulatory information

Regulatory Information · 2 items

Chemical: 1,10-Phenanthroline, 2,9-dimethyl-

1,10-Phenanthroline, 2,9-dimethyl-: Does not have an individual approval but may be used under an appropriate group standard

Safety data

wgk
3
tsca
TSCA listed
hs_code
29339990
risk_code
36/37/38-20/21/22-22
Signal word
Warning
Symbol(GHS)
GHS07

Chemistry & industry

Pharmacology

MeSH Pharmacological Classification · 2 items

Substances that inhibit or prevent the proliferation of NEOPLASMS.

Chemicals that bind to and remove ions from solutions. Many chelating agents function through the formation of COORDINATION COMPLEXES with METALS.

Uses & manufacturing

UsesUsed as a reagent in assays (blood glucose and spectrophotometric determination of copper); [Merck Index]
General Manufacturing Information1,10-Phenanthroline, 2,9-dimethyl-: ACTIVE
Applications · 2 items

UsesDue to the steric hindrance of the methyl groups attached to the carbon atoms adjacent to the nitrogen donor atoms of phenanthroline, the reagent does not give the low spin vivid red complex characteristic of phenanthroline derivatives with iron(II). However, in the presence of reducing agents it reacts with copper to give a copper(I) complex of composition MA2 and of tetrahedral symmetry. This chelate is insoluble in water and can be extracted by chloroform in which the absorption maximum of the complex appears at 457 nm. In this way the concentration of the complex can be measured. The method is suitable for the determination of copper in iron, manganese and vanadium ores even in the presence of aluminium, germanium, titanium and silicon. Neocuproine is today considered one of the most selective reagents. Unfortunately, it is rather expensive. 2,3-bis-(2-pyridyl)quinoxaline, prepared by Belcher et al. by condensation of o-diketone, 2,2'-dipyridyl and 0-phenylenediamine(44) contains the functional grouping characteristic of cuproine; it is quite suitable for the determination of copper and it is cheap. Starting with various substituted o-phenylene-diamines Belcher synthesized 25 different quinoxaline derivatives, of which 2,3-bis-[2-(-methyl)-pyridyl)]quinoxaline proved to be identical with neocuproine as regards analytical selectivity. Besides copper, titanium(III) is the only metal ion which gives a colour reaction with the reagent. However, the coloured titanium(III) complex is formed only at lower pH and hence it does not interfere with the determination of copper. The copper complex of the reagent can be extracted quantitatively with isopentyl alcohol usually as a perchlorate ion pair.

UsesNeocuproine is a phenanthroline based metal ion chelating agent.

Upstream & downstream products

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
河北凯诺新材料科技有限公司15932779957 or 18131036894 15932779957 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]
河北创海生物科技有限公司+86-86-13131129325 · [email protected]
上海如吉生物科技发展有限公司+86-21-65211385-8001 36031160 · [email protected]

Additional notes

DefinitionChEBI: A member of the class of phenanthrolines that is 1,10-phenanthroline bearing two methyl substituents at positions 2 and 9.

Related reactions

209 records
New reaction record

Linked notes

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