,3-Dicyanonaphthalene

,3-Dicyanonaphthalene - Names and Identifiers

Name	2,3-Dicyanonaphthalene
Synonyms	,3-Dicyanonaphthalene 2,3-DICYANONAHTHALENE 2,3-DICYANONAPHTHALENE 2,3-Dicyanonaphthalene 2,3-Naphthalenedicarbonitrile 2,3-NAPHTHALENEDICARBONITRILE naphthalene-2,3-dicarbonitrile NAPHTHALENE-2,3-DICARBONITRILE
CAS	22856-30-0
InChI	InChI=1/C12H6N2/c13-7-11-5-9-3-1-2-4-10(9)6-12(11)8-14/h1-6H

,3-Dicyanonaphthalene - Physico-chemical Properties

Molecular Formula	C12H6N2
Molar Mass	178.19
Density	1.2218 (rough estimate)
Melting Point	253-257 °C
Boling Point	300.41°C (rough estimate)
Flash Point	213.4°C
Vapor Presure	4.46E-07mmHg at 25°C
BRN	2574929
Storage Condition	Sealed in dry,Room Temperature
Refractive Index	1.5200 (estimate)
MDL	MFCD00059063

,3-Dicyanonaphthalene - Risk and Safety

Risk Codes	R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. R36/37/38 - Irritating to eyes, respiratory system and skin.
Safety Description	S36/37 - Wear suitable protective clothing and gloves. S37/39 - Wear suitable gloves and eye/face protection S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
UN IDs	3439
WGK Germany	3
Hazard Class	6.1
Packing Group	III

,3-Dicyanonaphthalene - Reference Information

Use

2,3-dicyanonaphthalene is a type of organic intermediate that can be used to prepare metal naphthalocyanine complexes. Metal naphthalocyanine complexes have strong absorption in the best transmission band of biological tissues, can be selectively retained in tumor tissues, and have obvious photodynamic killing effect on cancer cells. Compared with the current clinical photosensitizer hematoporphyrin derivatives, it has the characteristics of strong photosensitization and small phototoxic side effects, and is expected to become a promising photosensitizer for tumor photodynamic therapy.

preparation

2,3-dicyanonaphthalene The preparation method is as follows: step 1, synthesis of α,α,α',α'-tetrabromoo-xylene, 250ml of carbon tetrachloride and 6ml of o-xylene (49.8mmol) are measured in a 500ml three-neck bottle, and heated until reflux, dropping 11ml(199mmol) bromine,
at the same time with 500 watt ultraviolet high pressure mercury lamp irradiation, after several hours of dripping, continue to illuminate, investigate the effect of bromine dropping time, bromine dropping speed and ultraviolet lamp illumination time on the yield. After the reaction is completed, the excess
carbon tetrachloride is evaporated from the reaction solution, and the remaining small amount of the reaction solution is cooled, crystals are precipitated, filtered, and the refined product is recrystallized with chloroform to obtain white crystals. Step 2, 2,3-synthesis of dicyanonaphthalene 5g(11.9mmol)α,α,α',α'-tetrabromoo-xylene, 1.6g(0.02mol) fumaronitrile, 25g(0.17mol) of sodium iodide, 50ml of anhydrous DMF, the mixture was heated at 75 ℃
for several hours to investigate the effect of reaction time on yield. After the reaction is completed, the product is cooled, then 160ml of ice-water mixture is poured into a dark red suspension, and an appropriate amount is added to make it turn
into a light yellow suspension, filtered, precipitated, washed, dried, and recrystallized. The product is milky white needle-like crystals.

Last Update：2024-04-10 22:29:15