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Atenolol

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Name

Atenolol

EINECS 249-451-7
CAS No. 29122-68-7 Density 1.125 g/cm3
PSA 84.58000 LogP 1.54330
Solubility 0.3 mg/mL in water Melting Point 154 °C
Formula C14H22N2O3 Boiling Point 508.049 °C at 760 mmHg
Molecular Weight 266.34 Flash Point 261.059 °C
Transport Information N/A Appearance white to off-white crystalline solid
Safety 22-24/25-36-26 Risk Codes 22-36/37/38-20/21/22
Molecular Structure Molecular Structure of 29122-68-7 (Atenolol) Hazard Symbols HarmfulXn
Synonyms

Acetamide,2-[p-[2-hydroxy-3-(isopropylamino)propoxy]phenyl]- (8CI);(RS)-Atenolol;Alinor;Altol;Anselol;Antipressan;Apo-Atenolol;AteHexal;Atecard;Atelol;Atenblock;Atendol;Atenet;Ateni;Ateno;Atenolol;Aterol;B-Vasc;Betacard;Tenormin;Tenormine;Tensimin;Tredol;Urosin;Vericordin;Xaten;1-p-Carbamoylmethylphenoxy-3-isopropylamino-2-propanol;Catenol;Catenolol;Corotenol;Farnormin;Hipres;ICI 66082;Internolol;Lo-ten;Lotenal;Normalol;Noten;Oraday;Prenormine;SelesBeta;Serten;Telol;Teno-basan;Tenolin;Tenoprin;

Article Data 14

Atenolol Synthetic route

115538-83-5

1--3-chloropropan-2-ol

75-31-0

isopropylamine

29122-68-7

(RS)-atenolol

Conditions
ConditionsYield
In water at 10℃; for 12h;95%
29277-73-4

1-(4'-cyanomethylphenoxy)-2-hydroxy-3-(isopropylamino)propane

29122-68-7

(RS)-atenolol

Conditions
ConditionsYield
With bis(dimethylphosphinous acid-kP)dimethylphosphinyl-kP-hydridoplatinum(II) In ethanol; water for 72h; Reflux;93%
29122-69-8

(S)-1-[p-(carbamoylmethyl)phenoxy]-2,3-epoxypropane

75-31-0

isopropylamine

29122-68-7

(RS)-atenolol

Conditions
ConditionsYield
With Sulfated tungstate at 70℃; for 0.333333h; Green chemistry;90%
Stage #1: (S)-1-[p-(carbamoylmethyl)phenoxy]-2,3-epoxypropane; isopropylamine In N,N-dimethyl-formamide at 60℃; for 12h; Sealed tube;
Stage #2: With water In N,N-dimethyl-formamide at 60℃; for 12h; Solvent; Temperature; Sealed tube; regioselective reaction;
82.5%
In methanol for 2h; Heating; Yield given;
In methanol at 20℃; for 20h;

sodium; 4-carbamoylmethyl-phenolate

29122-68-7

(RS)-atenolol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) Amberlite IRA-400 / 1.) H2O, 2.) MeOH, room temperature, 10 h
2: methanol / 2 h / Heating
View Scheme
623-05-2

(4-hydroxyphenyl)methanol

29122-68-7

(RS)-atenolol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: N,N-dimethyl-formamide
2: bis(dimethylphosphinous acid-kP)dimethylphosphinyl-kP-hydridoplatinum(II) / ethanol; water / 18 h / Reflux
3: piperidine / 6 h / 95 - 100 °C
4: methanol / 20 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1: N,N-dimethyl-formamide
2: piperidine / 6 h / 95 - 100 °C
3: methanol / 20 h / 20 °C / 760.05 Torr
4: bis(dimethylphosphinous acid-kP)dimethylphosphinyl-kP-hydridoplatinum(II) / ethanol; water / 72 h / Reflux
View Scheme
17194-82-0

2-(4-hydroxyphenyl)acetamide

29122-68-7

(RS)-atenolol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: piperidine / 6 h / 95 - 100 °C
2: methanol / 20 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: tetrabutylammomium bromide; sodium hydroxide / water / 50 h / 4 °C
2: water / methanol / 20 °C
3: water / 12 h / 10 °C
View Scheme
Multi-step reaction with 2 steps
1.1: potassium carbonate / acetone / 24 h / Inert atmosphere; Reflux
2.1: N,N-dimethyl-formamide / 12 h / 60 °C / Sealed tube
2.2: 12 h / 60 °C / Sealed tube
View Scheme
14191-95-8

4-cyanomethylphenol

29122-68-7

(RS)-atenolol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: bis(dimethylphosphinous acid-kP)dimethylphosphinyl-kP-hydridoplatinum(II) / ethanol; water / 18 h / Reflux
2: piperidine / 6 h / 95 - 100 °C
3: methanol / 20 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: piperidine / 6 h / 95 - 100 °C
2: methanol / 20 h / 20 °C / 760.05 Torr
3: bis(dimethylphosphinous acid-kP)dimethylphosphinyl-kP-hydridoplatinum(II) / ethanol; water / 72 h / Reflux
View Scheme
35198-42-6

1-(4'-Cyanomethylphenoxy)-2,3-epoxypropane

29122-68-7

(RS)-atenolol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: methanol / 20 h / 20 °C / 760.05 Torr
2: bis(dimethylphosphinous acid-kP)dimethylphosphinyl-kP-hydridoplatinum(II) / ethanol; water / 72 h / Reflux
View Scheme
29122-69-8

(S)-1-[p-(carbamoylmethyl)phenoxy]-2,3-epoxypropane

29122-68-7

(RS)-atenolol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: water / methanol / 20 °C
2: water / 12 h / 10 °C
View Scheme
143925-21-7

1--2-acetoxy-3-chloropropane

29122-68-7

(RS)-atenolol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium carbonate; water / methanol / 2 h / 20 °C
2: water / 12 h / 10 °C
View Scheme

Atenolol Specification

The IUPAC name of Atenolol is 2-[4-[2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl]acetamide. With the CAS registry number 29122-68-7, it is also named as 1-p-Carbamoylmethylphenoxy-3-isopropylamino-2-propanol. The product's categories are Pharmaceutical; Intermediates & Fine Chemicals; Pharmaceuticals; API's; Adrenoceptor. Besides, it is white to off-white crystalline solid, which should be stored in tightly sealed container in a cool, dry place. And you should ensure that the workplaces have good ventilated or exhaust devices. In addition, its molecular formula is C14H22N2O3 and molecular weight is 266.34.

The other characteristics of this product can be summarized as: (1)EINECS: 249-451-7; (2)ACD/LogP: 0.34; (3)# of Rule of 5 Violations: 0; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 1; (7)ACD/KOC (pH 7.4): 1; (8)#H bond acceptors: 5; (9)#H bond donors: 4; (10)#Freely Rotating Bonds: 9; (11)Index of Refraction: 1.54; (12)Molar Refractivity: 74.257 cm3; (13)Molar Volume: 236.659 cm3; (14)Surface Tension: 45.019 dyne/cm; (15)Density: 1.125 g/cm3; (16)Flash Point: 261.059 °C; (17)Melting Point: 154 °C; (18)Enthalpy of Vaporization: 81.95 kJ/mol; (19)Boiling Point: 508.049 °C at 760 mmHg; (20)Solubility: H2O: 0.3 mg/mL; (21)Vapour Pressure: 0 mmHg at 25 °C.

Uses of Atenolol: this chemical is a selective β1 receptor antagonist, which is used primarily in cardiovascular diseases. It is also used for treatment of cardiovascular diseases and conditions such as hypertension, coronary heart disease, arrhythmias, angina (chest pain) and used to treat and reduce the risk of heart complications following myocardial infarction (heart attack). Additionally, it can be used for the treatment of symptoms of Graves Disease. Furthermore, it can be used to produce S(-)-Atenolol.



This reaction needs Rhizopus arrhizus, aq. Phosphate buffer and Butan-1-ol for 6 days. The yield is 75 %.

When you are using this chemical, please be cautious about it as the following: it is irritating to eyes, respiratory system and skin and harmful by inhalation, in contact with skin and if swallowed. In case of contact with eyes, please rinse immediately with plenty of water and seek medical advice. And you should wear suitable protective clothing to avoid contact with skin and eyes. Moreover, please do not breathe dust.

People can use the following data to convert to the molecule structure.
(1)SMILES: CC(C)NCC(COc1ccc(cc1)CC(=O)N)O
(2)InChI: InChI=1/C14H22N2O3/c1-10(2)16-8-12(17)9-19-13-5-3-11(4-6-13)7-14(15)18/h3-6,10,12,16-17H,7-9H2,1-2H3,(H2,15,18)
(3)InChIKey: METKIMKYRPQLGS-UHFFFAOYAT
(4)Std. InChI: InChI=1S/C14H22N2O3/c1-10(2)16-8-12(17)9-19-13-5-3-11(4-6-13)7-14(15)18/h3-6,10,12,16-17H,7-9H2,1-2H3,(H2,15,18)
(5)Std. InChIKey: METKIMKYRPQLGS-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man TDLo oral 10204ug/kg (10.204mg/kg) BEHAVIORAL: COMA

CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Anesthesiology. Vol. 83, Pg. 204, 1995.
man TDLo oral 49mg/kg/30D-I (49mg/kg) BEHAVIORAL: EXCITEMENT Journal of Clinical Pyschopharmacology. Vol. 6, Pg. 390, 1986.
man TDLo oral 86mg/kg/60D-I (86mg/kg) BLOOD: "CHANGES IN SERUM COMPOSITION (E.G., TP, BILIRUBIN, CHOLESTEROL)" American Journal of Medicine. Vol. 85, Pg. 586, 1988.
man TDLo oral 129mg/kg/26W- (129mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

LUNGS, THORAX, OR RESPIRATION: COUGH

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Annales de Medecine Interne. Vol. 148, Pg. 505, 1997.
mouse LD50 intraperitoneal 134mg/kg (134mg/kg)   Toksikologicheskii Vestnik. Vol. (4), Pg. 33, 1995.
mouse LD50 intravenous 57mg/kg (57mg/kg) PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE) Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 8, Pg. 4579, 1980.
mouse LD50 oral 2gm/kg (2000mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 8, Pg. 4579, 1980.
mouse LD50 subcutaneous > 400mg/kg (400mg/kg)   Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 8, Pg. 4579, 1980.
rabbit LD50 intravenous 50mg/kg (50mg/kg)   Drugs. International Journal of Current Therapeutics and Applied Pharmacology Reviews. Vol. 17, Pg. 425, 1979.
rat LD50 intravenous 77mg/kg (77mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 8, Pg. 4579, 1980.
rat LD50 oral > 2gm/kg (2000mg/kg)   Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 8, Pg. 4579, 1980.
rat LD50 subcutaneous > 600mg/kg (600mg/kg)   Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 8, Pg. 4579, 1980.
women TDLo oral 16mg/kg (16mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY OBSTRUCTION Annals of Emergency Medicine. Vol. 14, Pg. 161, 1985.
women TDLo oral 42mg/kg/3W-I (42mg/kg)   British Medical Journal. Vol. 294, Pg. 1324, 1987.
women TDLo oral 1080mg/kg/78W (1080mg/kg) BLOOD: LEUKOPENIA

MUSCULOSKELETAL: OTHER CHANGES

SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"
Journal of Rheumatology. Vol. 13, Pg. 446, 1986.

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