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34915-68-9

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34915-68-9 Usage

Originator

St resson,Boehringer Ingelheim,Boehringer Ingelheim,1976

Uses

Bunitrolol is a beta adrenoceptor antagonist that is used as an antihypertensive and antianginal agent.

Manufacturing Process

Epichlorohydrin and 2-cyanophenol are first reacted to give 1-(2- cyanophenoxy)-2,3-epoxypropane. 15 g (0.085 mol) of 1-(2-cyanophenoxy)-2,3-epoxy propane were dissolved in 100 ml of ethanol and 18.6 g (0.255 mol) of t-butylamine were added thereto. After standing for 1 hour at room temperature, the solution was heated at 60°-70°C for 2 hours after which the volatile constituents were distilled off in vacuo. The residue was digested with dilute HCl, and the insoluble constituents were vacuum filtered off. Then the filtrate was made alkaline with NaOH and the precipitating base was taken up in ether. After the ether solution had been dried over MgSO4, the ether was distilled off and the residue was dissolved in ethanol and by addition of ethereal HCl, the hydrochloride was precipitated there from in crystalline form which after recrystallization from ethanol with an addition of ether gave9.8 g of 1-(2- cyanophenoxy)-2-hydroxy-3-t-butylamino propane hydrochloride having a melting point of 163°-165°C.

Check Digit Verification of cas no

The CAS Registry Mumber 34915-68-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,4,9,1 and 5 respectively; the second part has 2 digits, 6 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 34915-68:
(7*3)+(6*4)+(5*9)+(4*1)+(3*5)+(2*6)+(1*8)=129
129 % 10 = 9
So 34915-68-9 is a valid CAS Registry Number.
InChI:InChI=1/C14H20N2O2/c1-14(2,3)16-9-12(17)10-18-13-7-5-4-6-11(13)8-15/h4-7,12,16-17H,9-10H2,1-3H3

34915-68-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-[3-(tert-butylamino)-2-hydroxypropoxy]benzonitrile

1.2 Other means of identification

Product number -
Other names Bunitrolol

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:34915-68-9 SDS

34915-68-9Relevant articles and documents

Efficient chemoenzymatic synthesis of (RS)-, (R)-, and (S)-bunitrolol

Banoth, Linga,Chandarrao, Bhukya,Pujala, Brahmam,Chakraborti, Asit K.,Banerjee

, p. 479 - 488 (2014/03/21)

A new chemical and the first chemoenzymatic synthesis of β-adrenergic receptor blocking agent bunitrolol is reported in racemic (RS) and enantioenriched forms (R and S). The intermediates (R)- and (S)-1-chloro-3-(2- cyanophenoxy)propan-2-ol intermediates were synthesized from the corresponding racemic alcohol through enzymatic kinetic resolution. The commercial available lipases PS-C and CCL exhibited complementary enantioselectivity during transesterification of the racemic alcohol with vinyl acetate affording the (R)-alcohol along with (S)-acetate and the (S)-alcohol along with (R)-acetate, respectively, and represent an example of enzymatic switch for reversal of enantioselectivity. The effects of various reaction parameters, such as temperature, time, substrate and enzyme concentration, and reaction medium, on the activity and enantioselectivity were optimized. The (R)- and (S)-alcohols were converted into (S)-and and (R)-bunitrolol, respectively, by treatment with tert-butylamine. The (R)- and (S)-acetates, obtained enzymatically were deacetylated to the corresponding alcohol by chemical hydrolysis and further converted into (S)-and and (R)-bunitrolol by chemical means. This is the first chemoenzymatic synthesis of both of the enantiomers of the drug. (RS)-, (R)-, and (S)-Bunitrolol were also synthesized following the 'all chemical' routes from (RS)-, (R)-, and (S)-epichlorohydrin via the corresponding (RS)-, (S)-, and (R)-2-cyanoglycidyl ether and the (RS)-, (R)-, and (S)-1-chloro-3-(2- cyanophenoxy)propan-2-ol intermediates with improved overall yields and better enantiomeric excesses compared to the reported processes.

ANTIHYPERTENSIVE THERAPY

-

, (2009/09/08)

A new use of darusentan is provided in preparation of a pharmaceutical composition for lowering blood pressure in a patient exhibiting resistance to a baseline antihypertensive therapy with one or more drugs. The composition comprises darusentan in an amount providing a therapeutically effective daily dose; wherein (a) the composition is orally deliverable and/or (b) the daily dose of darusentan is effective to provide a reduction of at least about 3 mmHg in one or more blood pressure parameters selected from trough sitting systolic, trough sitting diastolic, 24-hour ambulatory systolic, 24-hour ambulatory diastolic, maximum diurnal systolic and maximum diurnal diastolic blood pressures. Further provided is a new use of darusentan in preparation of a pharmaceutical composition for lowering blood pressure in a patient exhibiting resistance to a baseline antihypertensive therapy, wherein the composition is administered adjunctively with at least one diuretic and at least one antihypertensive drug selected from ACE inhibitors, angiotensin II receptor blockers, beta-adrenergic receptor blockers and calcium channel blockers.

Retard form of pharmaceuticals with insoluble porous diffusion coatings

-

, (2008/06/13)

A pharmaceutical dosage unit retard form having a constant, pH-independent release rate of active ingredient, consisting of a core comprising an active ingredient, and a semi-permeable diffusion coating over the core, were the coating consists of a water-insoluble film-former, a water-soluble polymer and eventually an acid-insoluble polymer incorporated therein.

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