Nipradilol

Base Information

• Chemical Name: Nipradilol
• CAS No.: 81486-22-8
• Molecular Formula: C₁₅H₂₂N₂O₆
• Molecular Weight: 326.349
• UNII: FVM336I71Y
• DSSTox Substance ID: DTXSID30868615
• Wikipedia: Nipradilol
• Wikidata: Q15634005
• NCI Thesaurus Code: C76555
• ChEMBL ID: CHEMBL155622
• Mol file: 81486-22-8.mol

Synonyms:3,4-dihydro-8-(2-hydroxy-3--isopropylaminopropoxy)-3-nitroxy-2H-1-benzopyran;K 351;K-351;nipradilol

Chemical Property of Nipradilol

Chemical Property:

• Appearance/Colour: Colorless needle crystal
• Vapor Pressure: 8.12E-11mmHg at 25°C
• Melting Point: 110-122 °C
• Refractive Index: 1.561
• Boiling Point: 499.992 °C at 760 mmHg
• Flash Point: 256.186 °C
• PSA: 105.77000
• Density: 1.278 g/cm³
• LogP: 1.85020
• XLogP3: 2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 7
• Exact Mass: 326.14778643
• Heavy Atom Count: 23
• Complexity: 376

Purity/Quality:

97% ^*data from raw suppliers

Nipradolol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)NCC(COC1=CC=CC2=C1OCC(C2)O[N+](=O)[O-])O
• Recent NIPH Clinical Trials: Neuroprotective efficacy of topical unoprostone isopropyl or nipradilol in patients with retinitis pigmentosa
• Description: Nipradilol is a beta-blocker with vasodilatory activity. As an antihypertensive nipradilol decreases systemic/pulmonary arterial blood pressure, heart rate, cardiac output and left ventricular volume without causing tachycardia. Nipradilol is also reported to have antiangina activity in dogs.
• Uses: Nipradolol is a β-adrenoceptor blocking agent with antihypertensive properties.?Nipradolol is used as an?anti-glaucomatous agent.

Technology Process of Nipradilol

There total 13 articles about Nipradilol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

3,4-dihydro-8-hydroxy-3-nitroxy-2H-1-benzopyran (81486-20-6) → (2'R)-3,4-dihydro-8-<2-hydroxy-3-(isopropylamino)propoxy>-3-nitroxy-2H-1-benzopyran (81486-22-8,99257-23-5,99257-24-6,100570-65-8,100570-66-9,100570-67-0,100570-68-1)

Guidance literature:

Multi-step reaction with 2 steps

1: K₂CO₃ / acetone / 17 h / 70 °C

2: ethanol / 1 h / 90 °C

With potassium carbonate; In ethanol; acetone;

DOI:10.1248/cpb.35.3691

Reference yield:

3,4-dihydro-8-hydroxy-3-nitroxy-2H-1-benzopyran (81486-20-6) → (2'S)-3,4-dihydro-8-<2-hydroxy-3-(isopropylamino)propoxy>-3-nitroxy-2H-1-benzopyran (81486-22-8,99257-23-5,99257-24-6,100570-65-8,100570-66-9,100570-67-0,100570-68-1)

Guidance literature:

Multi-step reaction with 2 steps

1: K₂CO₃ / acetone / 17 h / 70 °C

2: ethanol / 1 h / 90 °C

With potassium carbonate; In ethanol; acetone;

DOI:10.1248/cpb.35.3691

Reference yield:

2-Allyl-6-methoxyphenyl acetate (2173-78-6) → nipradilol (81486-22-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 88.7 percent / 40 percent (w/v) peracetic acid, AcOK / CH₂Cl₂ / 48 h / Ambient temperature

2: 90.4 percent / 20 percent (w/v) HCl / diethyl ether / 12 h / Ambient temperature

3: 1.53 g / K₂CO₃ / dimethylformamide / 2 h / Ambient temperature

4: 52.1 percent / 1 N NaOH / methanol / 1 h / Ambient temperature

5: 88.9 percent / 47 percent HBr / 9 h / 90 °C

6: 1.) ethyl chloroformate, triethylamine; 2.) Ac₂O, fum. HNO₃; 3.) NaOH / 1.) THF, 0-5 deg C, 0.5 h; 2.) acetonitrile, -8 deg C, 1 h; 3.) MeOH, H₂O, RT, 0.5 h

7: 1 N NaOH / 2 h / 50 °C

8: methanol / 1 h / 70 °C

With hydrogenchloride; peracetic acid; sodium hydroxide; hydrogen bromide; nitric acid; potassium acetate; chloroformic acid ethyl ester; acetic anhydride; potassium carbonate; triethylamine; In methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1248/cpb.35.632

upstream raw materials:

3,4-dihydro-8-(2,3-epoxy)propoxy-3-nitroxy-2H-1-benzopyran

isopropylamine

2-Allyl-6-methoxyphenyl acetate

8-methoxy-3,4-dihydro-2H-1-benzopyran-3-yl acetate

Downstream raw materials:

3,4-dihydro-8-<3'-(N-isopropyl-N-L-menthoxyacetyl)amino-2'-L-menthoxyacetyl>propoxy-3-nitroxy-2H-1-benzopyran

3,4-dihydro-3(SR)-hydroxy-8-(2'(RS)-hydroxy-3'-isopropylamino)propoxy-2H-1-benzopyran

(S)-{2-[1-(4-Chloro-benzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-acetoxy}-phenyl-acetic acid; compound with (R)-1-isopropylamino-3-((R)-3-nitrooxy-chroman-8-yloxy)-propan-2-ol

(R)-{2-[1-(4-Chloro-benzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-acetoxy}-phenyl-acetic acid; compound with (S)-1-isopropylamino-3-((S)-3-nitrooxy-chroman-8-yloxy)-propan-2-ol

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