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50-60-2

Basic Information
CAS No.: 50-60-2
Name: Phenol, 3-[[(4,5-dihydro-1H-imidazol-2-yl)methyl](4-methylphenyl)amino]-
Article Data: 5
Cas Database
Molecular Structure:
Molecular Structure of 50-60-2 (Phenol, 3-[[(4,5-dihydro-1H-imidazol-2-yl)methyl](4-methylphenyl)amino]-)
Formula: C17H19N3O
Molecular Weight: 281.357
Synonyms: Phenol,m-[N-(2-imidazolin-2-ylmethyl)-p-toluidino]- (8CI);2-(N'-p-Tolyl-N'-m-hydroxyphenylaminomethyl)-2-imidazoline;2-(m-Hydroxy-N-p-tolylanilinomethyl)-2-imidazoline;2-[[N-(m-Hydroxyphenyl)-p-toluidino]methyl]-2-imidazoline;C 7337;C 7337 Ciba;Dibasin;Fentolamine;Phentolamine;Regitin;Regitine;
EINECS: 200-053-1
Density: 1.185 g/cm3
Melting Point: 177 - 178oC
Boiling Point: 550.984 °C at 760 mmHg
Flash Point: 287.025 °C
Solubility: N/A
Appearance: white crystalline powder
Hazard Symbols: N/A
Risk Codes: N/A
Safety:
Transport Information: N/A
PSA: 47.86000
LogP: 2.60480
Synthetic route
61537-49-3

4-methyl-3'-hydroxydiphenylamine

13338-49-3

2-(chloromethyl)-2-imidazoline hydrochloride

50-60-2

phentolamine

Conditions
ConditionsYield
With triethyl phosphite In toluene for 6h; Heating;49%
With 1,2-dichloro-benzene
With 1,2-dichloro-benzene
107-15-3

ethylenediamine

N-<3-acetoxy-phenyl>-N-p-tolyl-glycine nitrile

N-<3-acetoxy-phenyl>-N-p-tolyl-glycine nitrile

50-60-2

phentolamine

Conditions
ConditionsYield
With carbon disulfide
With hydrogen sulfide
554-84-7

meta-nitrophenol

50-60-2

phentolamine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: zinc; ammonium chloride
2: triethyl phosphite / toluene / 0.75 h / 20 °C
3: triethyl phosphite / toluene / 6 h / Heating
View Scheme
50342-08-0

2-(chloromethyl)-imidazoline

61537-49-3

4-methyl-3'-hydroxydiphenylamine

50-60-2

phentolamine

Conditions
ConditionsYield
In toluene Reflux;
589-92-4

1-methylcyclohexan-4-one

50-60-2

phentolamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: styrene; 10 wt% Pd(OH)2 on carbon / toluene / 24 h / 140 °C / 3750.38 Torr / Flow reactor
2: toluene / Reflux
View Scheme
106-44-5

p-cresol

50-60-2

phentolamine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydrogen; palladium on activated charcoal / toluene / 140 °C / 1500.15 Torr / Flow reactor
2: styrene; 10 wt% Pd(OH)2 on carbon / toluene / 24 h / 140 °C / 3750.38 Torr / Flow reactor
3: toluene / Reflux
View Scheme
75-75-2

methanesulfonic acid

50-60-2

phentolamine

65-28-1

phentolamine mesylate

Conditions
ConditionsYield
In ethanol pH=5 - 6;99%
50-60-2

phentolamine

74-88-4

methyl iodide

3-[N-(1-methyl-4,5-dihydro-1H-imidazol-2-ylmethyl)-p-toluidino]-phenol; hydriodide

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Specification

The Phentolamine, with the CAS registry number 50-60-2, is also known as 2-[[N-(m-Hydroxyphenyl)-p-toluidino]methyl]-2-imidazoline. Its EINECS number is 200-053-1. This chemical's molecular formula is C17H19N3O and molecular weight is 281.36. What's more, its systematic name is 3-[(4,5-Dihydro-1H-imidazol-2-ylmethyl)(4-methylphenyl)amino]phenol. Its classification codes are: (1)Adrenergic Agents; (2)Adrenergic alpha-antagonists; (3)Adrenergic Antagonists; (4)Antihypertensive agents; (5)Cardiovascular Agents; (6)Drug / Therapeutic Agent; (7)Neurotransmitter Agents; (8)Reproductive Effect. This chemical is a nonselective alpha-adrenergic antagonist. It is used in the treatment of hypertension and hypertensive emergencies, pheochromocytoma and frostbite, clonidine withdrawal syndrome, impotence, and peripheral vascular disease. 

Physical properties of Phentolamine are: (1)ACD/LogP: 4.078; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.08; (4)ACD/LogD (pH 7.4): 2.13; (5)ACD/BCF (pH 5.5): 7.41; (6)ACD/BCF (pH 7.4): 8.34; (7)ACD/KOC (pH 5.5): 39.45; (8)ACD/KOC (pH 7.4): 44.39; (9)#H bond acceptors: 4; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 47.86 Å2; (13)Index of Refraction: 1.626; (14)Molar Refractivity: 83.976 cm3; (15)Molar Volume: 237.368 cm3; (16)Polarizability: 33.291×10-24cm3; (17)Surface Tension: 46.0 dyne/cm; (18)Density: 1.185 g/cm3; (19)Flash Point: 287.025 °C; (20)Enthalpy of Vaporization: 86.225 kJ/mol; (21)Boiling Point: 550.984 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: Oc3cc(N(c1ccc(cc1)C)CC/2=N/CCN\2)ccc3
(2)Std. InChI: InChI=1S/C17H19N3O/c1-13-5-7-14(8-6-13)20(12-17-18-9-10-19-17)15-3-2-4-16(21)11-15/h2-8,11,21H,9-10,12H2,1H3,(H,18,19)
(3)Std. InChIKey: MRBDMNSDAVCSSF-UHFFFAOYSA-N

The toxicity data is as follows:  

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 200mg/kg (200mg/kg) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

BEHAVIORAL: TREMOR

BEHAVIORAL: ATAXIA
Arzneimittel-Forschung. Drug Research. Vol. 21, Pg. 1727, 1971.
mouse LD50 intravenous 35mg/kg (35mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 105, Pg. 317, 1956.
mouse LD50 oral 1gm/kg (1000mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 112, Pg. 319, 1957.
rabbit LD50 intravenous 28mg/kg (28mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

LUNGS, THORAX, OR RESPIRATION: CYANOSIS

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 174, Pg. 243, 1968.
rabbit LD50 oral 2gm/kg (2000mg/kg)   Compilation of LD50 Values of New Drugs.
rabbit LDLo subcutaneous 200mg/kg (200mg/kg) PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Schweizerische Medizinische Wochenschrift. Vol. 81, Pg. 352, 1951.