Product Name

  • Name

    Naphazoline

  • EINECS 212-641-5
  • CAS No. 835-31-4
  • Article Data17
  • CAS DataBase
  • Density 1.156 g/cm3
  • Solubility
  • 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
  • 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;
  • PSA 24.39000
  • LogP 2.14840

Synthetic route

naphth-1-yl acetic acid
86-87-3

naphth-1-yl acetic acid

ethylenediamine
107-15-3

ethylenediamine

naphazoline
835-31-4

naphazoline

Conditions
ConditionsYield
for 2h; Time; Reflux;85%
With iron oxide In water; benzene at 80℃; for 4h;30%
naphthalen-1-ylacetonitrile
132-75-2

naphthalen-1-ylacetonitrile

ethylene diamine mono-p-toluenesulfonic acid salt
14034-59-4

ethylene diamine mono-p-toluenesulfonic acid salt

naphazoline
835-31-4

naphazoline

naphth-1-yl acetic acid
86-87-3

naphth-1-yl acetic acid

1,2-ethanediamine monohydrate
6780-13-8

1,2-ethanediamine monohydrate

naphazoline
835-31-4

naphazoline

Conditions
ConditionsYield
With hydrogenchloride
N-[1]naphthylacetyl-glycine nitrile

N-[1]naphthylacetyl-glycine nitrile

naphazoline
835-31-4

naphazoline

Conditions
ConditionsYield
With ammonia; nickel; isopropyl alcohol at 70℃; under 73550.8 Torr; Hydrogenation.Erhitzen des Reaktionsprodukts unter vermindertem Druck;
naphthalen-1-ylacetonitrile
132-75-2

naphthalen-1-ylacetonitrile

ethanolamine
141-43-5

ethanolamine

naphazoline
835-31-4

naphazoline

Conditions
ConditionsYield
With ammonium chloride; zinc(II) chloride
ethyl-[1]naphthylethynyl ether
100621-70-3

ethyl-[1]naphthylethynyl ether

ethylenediamine
107-15-3

ethylenediamine

naphazoline
835-31-4

naphazoline

naphthalen-1-ylacetonitrile
132-75-2

naphthalen-1-ylacetonitrile

ethylenediamine-mono hydrochloride

ethylenediamine-mono hydrochloride

naphazoline
835-31-4

naphazoline

1-naphthyl tosylate
68211-49-4

1-naphthyl tosylate

naphazoline
835-31-4

naphazoline

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

naphthalen-1-ylacetonitrile

ethylenediamine
107-15-3

ethylenediamine

naphazoline
835-31-4

naphazoline

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

naphazoline

naphazoline hydrochloride
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
835-31-4

naphazoline

Naphazole
1019-21-2

Naphazole

Conditions
ConditionsYield
palladium on activated charcoal In toluene for 200h; Heating;83%
palladium on activated charcoal In toluene for 216h; Heating;83%
terephthalonitrile
623-26-7

terephthalonitrile

naphazoline
835-31-4

naphazoline

C21H17N3

C21H17N3

Conditions
ConditionsYield
With thiobenzoic acid; potassium phosphate In N,N-dimethyl acetamide at 20℃; for 6h; Irradiation;67%
naphazoline
835-31-4

naphazoline

acetic anhydride
108-24-7

acetic anhydride

1-acetyl-2-[1]naphthylmethyl-4,5-dihydro-1H-imidazole

1-acetyl-2-[1]naphthylmethyl-4,5-dihydro-1H-imidazole

Conditions
ConditionsYield
With pyridine
naphazoline
835-31-4

naphazoline

acetic anhydride
108-24-7

acetic anhydride

A

1-acetyl-2-[1]naphthylmethyl-4,5-dihydro-1H-imidazole

1-acetyl-2-[1]naphthylmethyl-4,5-dihydro-1H-imidazole

B

1-acetylamino-2-(2-[1]naphthyl-acetylamino)-ethane

1-acetylamino-2-(2-[1]naphthyl-acetylamino)-ethane

Conditions
ConditionsYield
With pyridine
...Expand
naphazoline
835-31-4

naphazoline

acetic anhydride
108-24-7

acetic anhydride

1,3-diacetyl-2-[1]naphthylmethylene-imidazolidine

1,3-diacetyl-2-[1]naphthylmethylene-imidazolidine

naphazoline
835-31-4

naphazoline

benzoyl chloride
98-88-4

benzoyl chloride

1,3-dibenzoyl-2-[1]naphthylmethylene-imidazolidine

1,3-dibenzoyl-2-[1]naphthylmethylene-imidazolidine

Conditions
ConditionsYield
With benzene
naphazoline
835-31-4

naphazoline

N-(1-naphthylacetyl)ethylenediamine
36321-43-4

N-(1-naphthylacetyl)ethylenediamine

Conditions
ConditionsYield
With sodium hydroxide
With water
2-Chloronicotinoyl chloride
49609-84-9

2-Chloronicotinoyl chloride

naphazoline
835-31-4

naphazoline

1-<(2-chloro-3-pyridinyl)carbonyl>-4,5-dihydro-2-(1-naphthalenyl)-1H-imidazole
124372-93-6

1-<(2-chloro-3-pyridinyl)carbonyl>-4,5-dihydro-2-(1-naphthalenyl)-1H-imidazole

Conditions
ConditionsYield
With triethylamine In dichloromethane
naphazoline
835-31-4

naphazoline

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

2-Naphthalen-1-ylmethyl-4,5-dihydro-imidazole-1-carboxylic acid tert-butyl ester
126232-60-8

2-Naphthalen-1-ylmethyl-4,5-dihydro-imidazole-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
In tetrahydrofuran Ambient temperature; Yield given;
naphazoline
835-31-4

naphazoline

chloranil
118-75-2

chloranil

2-Naphthalen-1-ylmethyl-4,5-dihydro-1H-imidazole; compound with 2,3,5,6-tetrachloro-[1,4]benzoquinone

2-Naphthalen-1-ylmethyl-4,5-dihydro-1H-imidazole; compound with 2,3,5,6-tetrachloro-[1,4]benzoquinone

Conditions
ConditionsYield
In chloroform at 40℃; for 0.4h; Thermodynamic data; ΔG0;
In chloroform at 40℃; for 0.4h;
naphazoline
835-31-4

naphazoline

Naphazolin-Iod-Komplex

Naphazolin-Iod-Komplex

Conditions
ConditionsYield
With iodine In chloroform for 0.5h; Ambient temperature;
naphazoline
835-31-4

naphazoline

2-(naphthalen-4-yl)methyl-4,5-dihydro-1H-imidazole radical

2-(naphthalen-4-yl)methyl-4,5-dihydro-1H-imidazole radical

Conditions
ConditionsYield
With SO4-. radical In phosphate buffer at 22℃; pH=7.4; Kinetics; hydrogen abstraction;
With potassium peroxydiphosphate In water at 25℃; pH=7.1; Kinetics; Reagent/catalyst; Solvent; pH-value; Concentration; Inert atmosphere; Irradiation; aq. phosphate buffer;
2-(3-bromopropylamino)ethanol

2-(3-bromopropylamino)ethanol

naphazoline
835-31-4

naphazoline

2-[3-(2-naphthalen-1-ylmethyl-4,5-dihydro-imidazol-1-yl)-propylamino]-ethanol

2-[3-(2-naphthalen-1-ylmethyl-4,5-dihydro-imidazol-1-yl)-propylamino]-ethanol

Conditions
ConditionsYield
With triethylamine for 5h; Heating;
naphazoline
835-31-4

naphazoline

2-bromopropanol
598-18-5

2-bromopropanol

1-(2-naphthalen-1-ylmethyl-4,5-dihydro-imidazol-1-yl)-propan-2-ol

1-(2-naphthalen-1-ylmethyl-4,5-dihydro-imidazol-1-yl)-propan-2-ol

Conditions
ConditionsYield
With triethylamine for 5h; Heating;
naphazoline
835-31-4

naphazoline

2-bromoethanol
540-51-2

2-bromoethanol

2-(2-naphthalen-1-ylmethyl-4,5-dihydro-imidazol-1-yl)-ethanol

2-(2-naphthalen-1-ylmethyl-4,5-dihydro-imidazol-1-yl)-ethanol

Conditions
ConditionsYield
With triethylamine for 5h; Heating;
naphazoline
835-31-4

naphazoline

N-(2-bromoethyl)-2-[(1-naphthyl)methyl]-2-imidazoline

N-(2-bromoethyl)-2-[(1-naphthyl)methyl]-2-imidazoline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / 5 h / Heating
2: HBr; CH3COOH / tetrahydrofuran / 1 h / Heating
View Scheme
naphazoline
835-31-4

naphazoline

1-(2-bromopropyl)-2-[(1-naphthyl)methyl]-2-imidazoline

1-(2-bromopropyl)-2-[(1-naphthyl)methyl]-2-imidazoline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / 5 h / Heating
2: HBr; CH3COOH / tetrahydrofuran / 1 h / Heating
View Scheme
naphazoline
835-31-4

naphazoline

1-[N-(2-bromoethyl)-3-aminopropyl]-2-[1-naphthylmethyl]-2-imidazoline

1-[N-(2-bromoethyl)-3-aminopropyl]-2-[1-naphthylmethyl]-2-imidazoline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / 5 h / Heating
2: HBr; CH3COOH / tetrahydrofuran / 1 h / Heating
View Scheme
naphazoline
835-31-4

naphazoline

3-(4,5-Dihydro-1H-imidazol-2-yl)-3-naphthalen-1-yl-propionic acid
126232-64-2

3-(4,5-Dihydro-1H-imidazol-2-yl)-3-naphthalen-1-yl-propionic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: tetrahydrofuran / Ambient temperature
2: 1.) BuLi / 1.) THF, -78 deg C, 1 h, 2.) -78 deg C -> 20 deg C, 1 h, 20 deg C, 1 h
3: aq. HCl / acetic acid / 3 h / 40 °C
View Scheme
naphazoline
835-31-4

naphazoline

2-(2-tert-Butoxycarbonyl-1-naphthalen-1-yl-ethyl)-4,5-dihydro-imidazole-1-carboxylic acid tert-butyl ester
126262-55-3

2-(2-tert-Butoxycarbonyl-1-naphthalen-1-yl-ethyl)-4,5-dihydro-imidazole-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: tetrahydrofuran / Ambient temperature
2: 1.) BuLi / 1.) THF, -78 deg C, 1 h, 2.) -78 deg C -> 20 deg C, 1 h, 20 deg C, 1 h
View Scheme

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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