ChemicalBook--->CAS DataBase List--->59-98-3

59-98-3

59-98-3 Structure

59-98-3 Structure
IdentificationMore
[Name]

Tolazoline
[CAS]

59-98-3
[Synonyms]

2-BENZYL-2-IMIDAZOLINE
LABOTEST-BB LT00772362
TIMTEC-BB SBB003964
TOLAZOLINE
2-benzyl-2-imidazolin
2-Benzyl-4,5-dihydro-1H-imidazole
2-Benzyl-4,5-imidazoline
2-Benzyl-4,5-imidazoline hydrochloride
2-Benzylimidazoline
2-Imidazoline, 2-benzyl-
4,5-dihydro-2-(phenylmethyl)-1h-imidazol
4,5-Dihydro-2-(phenylmethyl)-1H-imidazole
Artonil
Benzazoline
Benzidazol
Benzolin
Benzylimidazoline
CIBA 3259
ciba3259
Dilatol ASI
[EINECS(EC#)]

200-448-9
[Molecular Formula]

C10H12N2
[MDL Number]

MFCD00005182
[Molecular Weight]

160.22
[MOL File]

59-98-3.mol
Chemical PropertiesBack Directory
[Melting point ]

66-69 °C(lit.)
[Boiling point ]

188°C/20mmHg(lit.)
[density ]

1.0849 (rough estimate)
[refractive index ]

1.6392 (estimate)
[storage temp. ]

2-8°C
[solubility ]

alcohol: freely soluble
[form ]

Solid
[pka]

pKa 10.3(H2O t undefined I = 0.1) (Uncertain)
[color ]

Crystals from pet ether
[Merck ]

13,9583
[CAS DataBase Reference]

59-98-3(CAS DataBase Reference)
[NIST Chemistry Reference]

1H-Imidazole, 4,5-dihydro-2-(phenylmethyl)-(59-98-3)
[EPA Substance Registry System]

59-98-3(EPA Substance)
Safety DataBack Directory
[Hazard Codes ]

Xn
[Risk Statements ]

R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin .
[Safety Statements ]

S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S28:After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer) .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
[WGK Germany ]

3
[RTECS ]

NJ1925000
[HS Code ]

2933299090
[Toxicity]

cyt-ham:lng 62,500 mg/L GMCRDC 27,95,81
Hazard InformationBack Directory
[Originator]

Priscoline,Ciba,US,1948
[Uses]

Reactant for synthesis of imidazoline-containing drug
[Uses]

Tolazoline is used for treating stable forms of pulmonary hypertension in newborns, and in cases where systemic arterial oxygenation cannot be achieved in the usual manner under careful observation of professionals.
[Definition]

ChEBI: A member of the class of imidazoles that is 4,5-dihydro-1H-imidazole substituted by a benzyl group.
[Manufacturing Process]

The phenyl-acetiminoether hydrochloride of the formula from 12 parts of benzylcyanide and ethanol and HCl is mixed with 8 parts of ethylenediamine hydrate which has been diluted with little alcohol, whereby the crystals go into solution. The whole is then heated on the water-bath until the ammonia odor has disappeared, cooled, concentrated caustic potash solution added, and the separated oil extracted with ether. The solution is dried with potassium carbonate and potassium hydroxide. After evaporation a pale oil is left which distills at 147°C under a pressure of 9 mm and which solidifies in the condenser to a white crystalline mass. The yield amounts to 90% of the theory. The hydrochloride melts at 168° to 170°C.
[Therapeutic Function]

Vasodilator
[General Description]

2-Benzylimidazoline is an active vasodilator.
[Pharmacology]

Tolazoline is a weak, reversible α-adrenoblocker that lowers resistance of peripheral blood vessels and elevates venous capacity. However, it also exhibits β-adrenomimetic activity, which consists of the stimulation of cardiac work and is manifest as tachycardia, cholinergic activity, which consists of stimulation of the gastrointestinal tract, and histamine-like activity, which consists of stimulation of gastric secretion.
[Safety Profile]

Poison by ingestion,intraperitoneal, and intravenous routes. Mutation data reported. When heated to decomposition it emits toxicfumes of NOx.
[Synthesis]

Tolazoline, 2-benzyl-2-imidazoline (12.2.7), is synthesized by the heterocyclation of the ethyl ester of iminophenzylacetic acid with ethylendiamine (12.2.6), which forms the desired product (12.2.7) [32¨C35]. The structure of tolazoline is strikingly similar to |á-adrenergic agonists, which are antiedema sympathomimetics.

Synthesis_59-98-3

[storage]

Store at -20°C
Spectrum DetailBack Directory
[Spectrum Detail]

Tolazoline(59-98-3)1HNMR
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

59-98-3(sigmaaldrich)
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