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[(2S)-3-[4-(2-amino-2-oxoethyl)phenoxy]-2-hydroxypropyl]-propan-2-ylammonium
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Raw Material CAS 29122-68-7 Atenolol Powder Pharmaceutical Intermediate Atenolol High Purity API Atenolol
Cas No: 29122-68-7
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29122-68-7 Usage

Chemical Property

White powder. Melting point (146-148 ℃). Soluble in alcohol, slightly soluble in water, chloroform, Hardly soluble in ethyl ether, slightly smelly.

Brand name

Tenormin (AstraZeneca).

Pharmacological Affects

Atenolol ,also known as atenolol, Aten Yue Er, tamoxifen, downhill Ling blood pressure, Tenormin, blood pressure Ling, is a long-acting cardioselective β1-adrenergic blockers, without intrinsic sympathomimetic activity or membrane stability.The atenolol,s retardation for β1 adrenaline receptors is similar with metoprolol, propranolol and nadolol , which is 1/6 times for pindolol and timolol. But, it does not inhibit the effect of the isoproterenol bronchodilator.When administered in small doses, it does not like non-selective β-adrenergic blockers as aggravated hypoglycemia induced hypertensive crisis, peripheral circulatory impairment or patients with obstructive airways disease worsening airway function and so on. However, When administered in large doses, atenolol also can decrease asthma or chronic obstructive pulmonary disease, airway function. Atenolol, as a long-term treatment of hypertension, also were reported for affecting airway function. Thus, despite atenolol heart selection, chronic obstructive pulmonary disease patients can only use small doses, but also should be given a sufficient amount of β1-adrenergic receptor agonists.
Oral F is 46%~60%, Tmax about 2~4 h, Mainly unchanged since the urine excretion, T1/2 of 6~7 h. Hemodialysis can clear the goods. Rapidly absorbed from the gastrointestinal tract, but not exclusively.The rest of the body is excreted in the stool. Food can reduce the F, fasting and after meals AUC decreased by 20%. Distribution of the central nervous system is relatively few. The ratio of brain tissue to blood concentration was 0.1:1. Easy to achieve in the placenta and the maternal plasma concentrations of same. PPB is less than 5%, Vd is 50~75 L. Atenolol is not metabolized by the liver, most of the drug is excreted from the body in urine, renal insufficiency in patients with T1/2 was significantly prolonged. Patients with renal failure range of T1/2 was 10~28 h, or even up to 100 h. Results at 24 h after, the discharge from the urine of the drug can be reduced by 29%. The T1/2 of patients with hyperthyroidism was significantly shortened, 4.2h.
The above information is edited by the chemicalbook of Kui Ming.

Uses

β-blockers. Clinical application in the treatment of hypertension, angina and arrhythmia.

Biological Activity

Cardioselective β -adrenergic blocker. Antihypertensive, antianginal, antiarrhythmic.

Uses

Selective b1 adrenergic receptor agonist, anti-hypertensive, anti-anginal, anti-arrhythmic

Definition

ChEBI: An ethanolamine compound having a (4-carbamoylmethylphenoxy)methyl group at the 1-position and an N-isopropyl substituent.
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)/p+1/t12-/m0/s1

29122-68-7 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
Sigma (A7655)  Atenolol  ≥98% (TLC), powder 29122-68-7 A7655-5G 1,767.87CNY Detail
Sigma (A7655)  Atenolol  ≥98% (TLC), powder 29122-68-7 A7655-1G 795.60CNY Detail
Sigma-Aldrich (A1340000)  Atenolol  European Pharmacopoeia (EP) Reference Standard 29122-68-7 A1340000 1,880.19CNY Detail

29122-68-7SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name atenolol

1.2 Other means of identification

Product number -
Other names Altol

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:29122-68-7 SDS

29122-68-7Synthetic route

1--3-chloropropan-2-ol
115538-83-5

1--3-chloropropan-2-ol

isopropylamine
75-31-0

isopropylamine

(RS)-atenolol
29122-68-7

(RS)-atenolol

Conditions
ConditionsYield
In water at 10℃; for 12h;95%
1-(4'-cyanomethylphenoxy)-2-hydroxy-3-(isopropylamino)propane
29277-73-4

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

(RS)-atenolol
29122-68-7

(RS)-atenolol

Conditions
ConditionsYield
With bis(dimethylphosphinous acid-kP)dimethylphosphinyl-kP-hydridoplatinum(II) In ethanol; water for 72h; Reflux;93%
(S)-1-[p-(carbamoylmethyl)phenoxy]-2,3-epoxypropane
29122-69-8

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

isopropylamine
75-31-0

isopropylamine

(RS)-atenolol
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

sodium; 4-carbamoylmethyl-phenolate

(RS)-atenolol
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
(4-hydroxyphenyl)methanol
623-05-2

(4-hydroxyphenyl)methanol

(RS)-atenolol
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
2-(4-hydroxyphenyl)acetamide
17194-82-0

2-(4-hydroxyphenyl)acetamide

(RS)-atenolol
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
4-cyanomethylphenol
14191-95-8

4-cyanomethylphenol

(RS)-atenolol
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
1-(4'-Cyanomethylphenoxy)-2,3-epoxypropane
35198-42-6

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

(RS)-atenolol
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
(S)-1-[p-(carbamoylmethyl)phenoxy]-2,3-epoxypropane
29122-69-8

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

(RS)-atenolol
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
1--2-acetoxy-3-chloropropane
143925-21-7

1--2-acetoxy-3-chloropropane

(RS)-atenolol
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
(RS)-atenolol
29122-68-7

(RS)-atenolol

1-(4'-cyanomethylphenoxy)-2-hydroxy-3-(isopropylamino)propane
29277-73-4

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

Conditions
ConditionsYield
With (dimethoxy)methylsilane; copper diacetate; 1,2-bis-(dicyclohexylphosphino)ethane In tetrahydrofuran at 20℃; for 12h; Sealed tube;96%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

(RS)-atenolol
29122-68-7

(RS)-atenolol

[3-(4-carbamoylmethyl-phenoxy)-2-hydroxy-propyl]isopropyl-carbamic acid tert-butyl ester
956017-06-4

[3-(4-carbamoylmethyl-phenoxy)-2-hydroxy-propyl]isopropyl-carbamic acid tert-butyl ester

Conditions
ConditionsYield
In water; tert-butyl alcohol at 20℃; for 3h;95%
(E)-3-phenylacrylic acid
140-10-3

(E)-3-phenylacrylic acid

(RS)-atenolol
29122-68-7

(RS)-atenolol

(E)-N-(3-(3-(2-amino-2-oxoethyl)phenoxy)-2-hydroxypropyl)-N-isopropylcinnamamide

(E)-N-(3-(3-(2-amino-2-oxoethyl)phenoxy)-2-hydroxypropyl)-N-isopropylcinnamamide

Conditions
ConditionsYield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In dichloromethane at 20℃; for 24h;92%
trifluoromethyl trifluoromethanesulfonate
3582-05-6

trifluoromethyl trifluoromethanesulfonate

(RS)-atenolol
29122-68-7

(RS)-atenolol

2-(4-((3-isopropyl-2-oxooxazolidin-5-yl)methoxy)phenyl)acetamide

2-(4-((3-isopropyl-2-oxooxazolidin-5-yl)methoxy)phenyl)acetamide

Conditions
ConditionsYield
In acetonitrile at 20℃; for 1h; Sealed tube;88%
ethanol
64-17-5

ethanol

(RS)-atenolol
29122-68-7

(RS)-atenolol

telmisatran
144701-48-4

telmisatran

telmisartan-atenolol-EtOH salt

telmisartan-atenolol-EtOH salt

Conditions
ConditionsYield
In ethanol at 20℃; for 15h; Concentration; Time;80%
3,4-dimethoxy-trans-cinnamic acid
14737-89-4

3,4-dimethoxy-trans-cinnamic acid

(RS)-atenolol
29122-68-7

(RS)-atenolol

(E)-N-(3-(3-(2-amino-2-oxoethyl)phenoxy)-2-hydroxypropyl)-3-(3,4-dimethoxyphenyl)-N-isopropylacrylamide

(E)-N-(3-(3-(2-amino-2-oxoethyl)phenoxy)-2-hydroxypropyl)-3-(3,4-dimethoxyphenyl)-N-isopropylacrylamide

Conditions
ConditionsYield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In dichloromethane at 20℃; for 24h;80%
(RS)-atenolol
29122-68-7

(RS)-atenolol

telmisatran
144701-48-4

telmisatran

telmisartan-atenolol salt

telmisartan-atenolol salt

Conditions
ConditionsYield
In acetonitrile at 20℃; for 6h;79%
(RS)-atenolol
29122-68-7

(RS)-atenolol

(E)-3-(3-phenoxyphenyl)acrylic acid
77124-20-0

(E)-3-(3-phenoxyphenyl)acrylic acid

(E)-N-(3-(3-(2-amino-2-oxoethyl)phenoxy)-2-hydroxypropyl)-N-isopropyl-3-(3-phenoxyphenyl)acrylamide

(E)-N-(3-(3-(2-amino-2-oxoethyl)phenoxy)-2-hydroxypropyl)-N-isopropyl-3-(3-phenoxyphenyl)acrylamide

Conditions
ConditionsYield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In dichloromethane at 20℃; for 24h;78%
(RS)-atenolol
29122-68-7

(RS)-atenolol

C8H11ClO8

C8H11ClO8

C22H32N2O11

C22H32N2O11

Conditions
ConditionsYield
In ethanol for 2h;76%
(RS)-atenolol
29122-68-7

(RS)-atenolol

(S)-Atenolol
93379-54-5

(S)-Atenolol

Conditions
ConditionsYield
With Rhizopus arrhizus In phosphate buffer; butan-1-ol for 144h; pH=7.0; Product distribution; Further Variations:; pH-values; Reagents; biodegradation;75%
Multi-step reaction with 2 steps
1: Pseudomonas cepacia lipase/diatomite / tetrahydrofuran / 10 h / 20 °C / Enzymatic reaction
2: K2CO3; MeOH
View Scheme
With lipoprotein burkholderia sp In tetrahydrofuran at 40℃; for 24h; Enzymatic reaction; enantioselective reaction;n/a
(RS)-atenolol
29122-68-7

(RS)-atenolol

N-methyl-N-phenyl-vinylsulfonamide
28792-97-4

N-methyl-N-phenyl-vinylsulfonamide

C23H33N3O5S

C23H33N3O5S

Conditions
ConditionsYield
With potassium hydroxide In tetrahydrofuran at 20℃;73%
formaldehyd
50-00-0

formaldehyd

(RS)-atenolol
29122-68-7

(RS)-atenolol

2-[4-(3-isopropyl-oxazolidin-5-ylmethoxy)-phenyl]-acetamide
29121-59-3

2-[4-(3-isopropyl-oxazolidin-5-ylmethoxy)-phenyl]-acetamide

Conditions
ConditionsYield
With potassium hydroxide; sodium sulfate In methanol for 8h; Heating;70.4%
cobalt(II) chloride dihydrate

cobalt(II) chloride dihydrate

(RS)-atenolol
29122-68-7

(RS)-atenolol

[Co(4-[2-hydroxy-3-[(1-methylethyl)amino]propoxy]benzeneacetamide(-1H))2(H2O)2]
796073-42-2

[Co(4-[2-hydroxy-3-[(1-methylethyl)amino]propoxy]benzeneacetamide(-1H))2(H2O)2]

Conditions
ConditionsYield
In water; acetonitrile to soln. of ligand in H2O/MeCN (1/5 v/v) soln. of metal salt in MeCN/H2O(5/1, v/v) added; mixt. stirred for 30 min at room temp.; ppt. filtered; washed (MeCN/H2O, 1:1 v/v); dried (vac., P4O10) for several ds; elem. anal.;65%
(RS)-atenolol
29122-68-7

(RS)-atenolol

copper(II) acetate monohydrate
6046-93-1

copper(II) acetate monohydrate

[Cu2(4-[2-hydroxy-3-[(1-methylethyl)amino]propoxy]benzeneacetamide(-1H))2(OAc)2]
796073-41-1

[Cu2(4-[2-hydroxy-3-[(1-methylethyl)amino]propoxy]benzeneacetamide(-1H))2(OAc)2]

Conditions
ConditionsYield
In methanol to soln. of ligand in MeOH added dropwise soln. of metal salt in MeOH; mixt. stirred for 20 min at room temp.; ppt. filtered; washed (MeOH/H2O, 1:1 v/v); dried (vac., P4O10) for several ds; elem. anal.;65%
formaldehyd
50-00-0

formaldehyd

(RS)-atenolol
29122-68-7

(RS)-atenolol

N-Hydroxymethyl-2-[4-(3-isopropyl-oxazolidin-5-ylmethoxy)-phenyl]-acetamide

N-Hydroxymethyl-2-[4-(3-isopropyl-oxazolidin-5-ylmethoxy)-phenyl]-acetamide

Conditions
ConditionsYield
In methanol for 8h; Heating;61%
(RS)-atenolol
29122-68-7

(RS)-atenolol

(+/-)-O-Demethylmetoprolol

(+/-)-O-Demethylmetoprolol

Conditions
ConditionsYield
With samarium diiodide; water; triethylamine In tetrahydrofuran at 23℃; for 18h; Inert atmosphere; chemoselective reaction;61%
(RS)-atenolol
29122-68-7

(RS)-atenolol

copper(II) acetate monohydrate
6046-93-1

copper(II) acetate monohydrate

[Cu(4-[2-hydroxy-3-[(1-methylethyl)amino]propoxy]benzeneacetamide)4][OAc]2

[Cu(4-[2-hydroxy-3-[(1-methylethyl)amino]propoxy]benzeneacetamide)4][OAc]2

Conditions
ConditionsYield
In methanol to soln. of ligand in MeOH added dropwise soln. of metal salt in MeOH; mixt. stirred for 48 h at 4°C; ppt. filtered; washed (MeOH/H2O, 1:1 v/v); dried (vac., P4O10) for several ds; elem. anal.;52%
(RS)-atenolol
29122-68-7

(RS)-atenolol

1-{[(4-nitrophenoxy)carbonyl]oxy}ethyl acetate
101623-68-1

1-{[(4-nitrophenoxy)carbonyl]oxy}ethyl acetate

4-<2-hydroxy-3--N-isopropylamino>propoxy>benzeneacetamide
101623-75-0

4-<2-hydroxy-3--N-isopropylamino>propoxy>benzeneacetamide

Conditions
ConditionsYield
In N,N,N,N,N,N-hexamethylphosphoric triamide Ambient temperature;32%
(RS)-atenolol
29122-68-7

(RS)-atenolol

4-<2-hydroxy-3--N-isopropylamino>propoxy>benzeneacetamide
101623-75-0

4-<2-hydroxy-3--N-isopropylamino>propoxy>benzeneacetamide

Conditions
ConditionsYield
32%
3-Bromoindan-1-one
40774-41-2

3-Bromoindan-1-one

(RS)-atenolol
29122-68-7

(RS)-atenolol

2-(4-{2-hydroxy-3-[isopropyl-(3-oxoindan-1-yl)amino]propoxy}phenyl)acetamide

2-(4-{2-hydroxy-3-[isopropyl-(3-oxoindan-1-yl)amino]propoxy}phenyl)acetamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0℃;11.8%
(RS)-atenolol
29122-68-7

(RS)-atenolol

3-chlorophenyl-isothiocyanate
2392-68-9

3-chlorophenyl-isothiocyanate

2-(4-(3-(3-(3'-chlorophenyl)-1-isopropylthioureido)-2-hydroxypropoxy)phenyl)acetamide

2-(4-(3-(3-(3'-chlorophenyl)-1-isopropylthioureido)-2-hydroxypropoxy)phenyl)acetamide

Conditions
ConditionsYield
In acetonitrile at 80℃;0.98%
(RS)-atenolol
29122-68-7

(RS)-atenolol

phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

2-(4-(2-hydroxy-3-(1-isopropyl-3-phenylthioureido)propoxy)phenyl)acetamide

2-(4-(2-hydroxy-3-(1-isopropyl-3-phenylthioureido)propoxy)phenyl)acetamide

Conditions
ConditionsYield
In acetonitrile at 80℃;0.95%
2-chlorophenylisothiocyanate
2740-81-0

2-chlorophenylisothiocyanate

(RS)-atenolol
29122-68-7

(RS)-atenolol

2-(4-(3-(3-(2'-chlorophenyl)-1-isopropylthioureido)-2-hydroxypropoxy)phenyl)acetamide

2-(4-(3-(3-(2'-chlorophenyl)-1-isopropylthioureido)-2-hydroxypropoxy)phenyl)acetamide

Conditions
ConditionsYield
In acetonitrile at 80℃;0.95%
(RS)-atenolol
29122-68-7

(RS)-atenolol

2,4-difluorophenyl isothiocyanate
141106-52-7

2,4-difluorophenyl isothiocyanate

2-(4-(3-(3-(2',4'-difluorophenyl)-1-isopropylthioureido)-2-hydroxypropoxy)phenyl)acetamide

2-(4-(3-(3-(2',4'-difluorophenyl)-1-isopropylthioureido)-2-hydroxypropoxy)phenyl)acetamide

Conditions
ConditionsYield
In acetonitrile at 80℃;0.95%
(RS)-atenolol
29122-68-7

(RS)-atenolol

1-bromo-2-isothiocyanatobenzene
13037-60-0

1-bromo-2-isothiocyanatobenzene

2-(4-(3-(3-(2'-bromophenyl)-1-isopropylthioureido)-2-hydroxypropoxy)phenyl)acetamide

2-(4-(3-(3-(2'-bromophenyl)-1-isopropylthioureido)-2-hydroxypropoxy)phenyl)acetamide

Conditions
ConditionsYield
In acetonitrile at 80℃;0.94%
(RS)-atenolol
29122-68-7

(RS)-atenolol

1-ethoxy-4-isothiocyanatobenzene
3460-49-9

1-ethoxy-4-isothiocyanatobenzene

2-(4-(3-(3-(4'-ethoxyphenyl)-1-isopropylthioureido)-2-hydroxypropoxy)phenyl)acetamide

2-(4-(3-(3-(4'-ethoxyphenyl)-1-isopropylthioureido)-2-hydroxypropoxy)phenyl)acetamide

Conditions
ConditionsYield
In acetonitrile at 80℃;0.94%

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