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Naphazoline

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Name

Naphazoline

EINECS 212-641-5
CAS No. 835-31-4 Density 1.156 g/cm3
PSA 24.39000 LogP 2.14840
Solubility N/A Melting Point 254 °C
Formula C14H15ClN2 Boiling Point 440.466 °C at 760 mmHg
Molecular Weight 210.279 Flash Point 220.186 °C
Transport Information UN 2811 6.1/PG 2 Appearance N/A
Safety 45 Risk Codes 25
Molecular Structure Molecular Structure of 835-31-4 (Naphazoline) Hazard Symbols ToxicT
Synonyms

2-Imidazoline,2-(1-naphthylmethyl)- (7CI,8CI);Naphazoline (6CI);2-(1-Naphthalenylmethyl)-2-imidazoline;2-(1-Naphthylmethyl)-2-imidazoline;Antan;Antigaimorit;Colirio Alfa;Euboral Oftalmico;Imidin;Naphthazoline;Naphthizine;Rhinazine;

Article Data 17

Naphazoline Synthetic route

86-87-3

naphth-1-yl acetic acid

107-15-3

ethylenediamine

835-31-4

naphazoline

Conditions
ConditionsYield
for 2h; Time; Reflux;85%
With iron oxide In water; benzene at 80℃; for 4h;30%
132-75-2

naphthalen-1-ylacetonitrile

14034-59-4

ethylene diamine mono-p-toluenesulfonic acid salt

835-31-4

naphazoline

86-87-3

naphth-1-yl acetic acid

6780-13-8

1,2-ethanediamine monohydrate

835-31-4

naphazoline

Conditions
ConditionsYield
With hydrogenchloride

N-[1]naphthylacetyl-glycine nitrile

835-31-4

naphazoline

Conditions
ConditionsYield
With ammonia; nickel; isopropyl alcohol at 70℃; under 73550.8 Torr; Hydrogenation.Erhitzen des Reaktionsprodukts unter vermindertem Druck;
132-75-2

naphthalen-1-ylacetonitrile

141-43-5

ethanolamine

835-31-4

naphazoline

Conditions
ConditionsYield
With ammonium chloride; zinc(II) chloride
100621-70-3

ethyl-[1]naphthylethynyl ether

107-15-3

ethylenediamine

835-31-4

naphazoline

132-75-2

naphthalen-1-ylacetonitrile

ethylenediamine-mono hydrochloride

ethylenediamine-mono hydrochloride

835-31-4

naphazoline

68211-49-4

1-naphthyl tosylate

835-31-4

naphazoline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: diethyl ether
View Scheme
132-75-2

naphthalen-1-ylacetonitrile

107-15-3

ethylenediamine

835-31-4

naphazoline

Conditions
ConditionsYield
With carbon disulfide at 110℃; for 2h; Reagent/catalyst; Temperature;
835-31-4

naphazoline

550-99-2

naphazoline hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In acetonitrile at 20℃; Solvent; Large scale;92.33%
With hydrogenchloride In acetone at 5℃; for 0.5h; pH=1; Temperature; Reflux;

Naphazoline Specification

The Naphazoline, with the CAS registry number 835-31-4, is also known as 1H-Imidazole, 4,5-dihydro-2-(1-naphthalenylmethyl)-. It belongs to the product category of API. Its EINECS registry number is 212-641-5. This chemical's molecular formula is C14H15ClN2 and molecular weight is 246.74. What's more, its IUPAC name is called 2-(Naphthalen-1-ylmethyl)-4,5-dihydro-1H-imidazole. Naphazoline is a sympathomimetic agent with marked alpha adrenergic activity. It is a vasoconstrictor with a rapid action in reducing swelling when applied to mucous membrane. This chemical acts on alpha-receptors in the arterioles of the conjunctiva to produce constriction, resulting in decreased congestion.

Physical properties about Naphazoline are: (1)ACD/LogP: 2.988; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.99; (4)ACD/LogD (pH 7.4): 1.04; (5)ACD/BCF (pH 5.5): 1.10; (6)ACD/BCF (pH 7.4): 1.25; (7)ACD/KOC (pH 5.5): 10.07; (8)ACD/KOC (pH 7.4): 11.40; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 24.39 Å2; (13)Index of Refraction: 1.64; (14)Molar Refractivity: 65.526 cm3; (15)Molar Volume: 181.848 cm3; (16)Polarizability: 25.976×10-24 cm3; (17)Surface Tension: 44.63 dyne/cm; (18)Density: 1.156 g/cm3; (19)Flash Point: 220.186 °C; (20)Enthalpy of Vaporization: 67.071 kJ/mol; (21)Boiling Point: 440.466 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25 °C.

Uses of Naphazoline: it is used to produce other chemicals. For example, it can produce 2-(1-naphthylmethyl)imidazole. The reaction occurs with solvent toluene and other condition of heating for 200 hours. The yield is 83 %.

Naphazoline can produce 2-(1-naphthylmethyl)imidazole.

When you are dealing with this chemical, you should be very careful. This chemical may cause damage to health at low levels. It is toxic if swallowed. In case of accident or if you feel unwell you should seek medical advice immediately.

You can still convert the following datas into molecular structure:
(1) SMILES: N\1=C(\NCC/1)Cc2cccc3c2cccc3
(2) InChI: InChI=1S/C14H14N2/c1-2-7-13-11(4-1)5-3-6-12(13)10-14-15-8-9-16-14/h1-7H,8-10H2,(H,15,16)
(3) InChIKey: CNIIGCLFLJGOGP-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mammal (species unspecified) LDLo intravenous 10mg/kg (10mg/kg)   Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 192, Pg. 141, 1939.
mouse LD50 intraperitoneal 62mg/kg (62mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 29, Pg. 729, 1979.
mouse LD50 intravenous 170mg/kg (170mg/kg)   Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 9, Pg. 280, 1950.
mouse LD50 oral 270mg/kg (270mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 29, Pg. 729, 1979.
mouse LD50 subcutaneous 514mg/kg (514mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Russian Pharmacology and Toxicology Vol. 37, Pg. 198, 1974.
rabbit LD50 intravenous 800ug/kg (.8mg/kg)   Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 9, Pg. 280, 1950.
rabbit LD50 subcutaneous 950ug/kg (.95mg/kg)   Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 9, Pg. 280, 1950.
rat LD50 subcutaneous 385mg/kg (385mg/kg)   Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 9, Pg. 280, 1950.

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