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52240-25-2

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52240-25-2 Usage

General Description

4-CHLORO-BETA-METHYL-Y-OXO-BENZENEBUTANOIC ACID, also known as clofibric acid, is a chemical compound used as a lipid-lowering agent to reduce blood lipid levels. It is a derivative of fibric acid and functions as a peroxisome proliferator-activated receptor alpha (PPARα) agonist, which plays a role in regulating lipid metabolism. It works by increasing the breakdown of fatty acids and decreasing the production of triglycerides in the liver. Clofibric acid has been used in the past as a pharmaceutical drug to treat high cholesterol and triglyceride levels, but its use has declined due to safety concerns and the availability of more effective lipid-lowering medications. However, it is still used as a research tool in studying lipid metabolism and PPARα function.

Check Digit Verification of cas no

The CAS Registry Mumber 52240-25-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,2,2,4 and 0 respectively; the second part has 2 digits, 2 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 52240-25:
(7*5)+(6*2)+(5*2)+(4*4)+(3*0)+(2*2)+(1*5)=82
82 % 10 = 2
So 52240-25-2 is a valid CAS Registry Number.
InChI:InChI=1/C11H11ClO3/c1-7(6-10(13)14)11(15)8-2-4-9(12)5-3-8/h2-5,7H,6H2,1H3,(H,13,14)

52240-25-2SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-(4-Chlorophenyl)-3-methyl-4-oxobutanoic acid

1.2 Other means of identification

Product number -
Other names HMS1394L09

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:52240-25-2 SDS

52240-25-2Synthetic route

4-(4-chlorophenyl)-3-methyl-4-oxobutyronitrile
53012-96-7

4-(4-chlorophenyl)-3-methyl-4-oxobutyronitrile

4-(4-chlorophenyl)-3-methyl-4-oxobutanoic acid
52240-25-2

4-(4-chlorophenyl)-3-methyl-4-oxobutanoic acid

Conditions
ConditionsYield
With hydrogenchloride; water at 100℃; for 5h; Inert atmosphere;72%
With hydrogenchloride; water at 100℃; for 5h; Inert atmosphere;72%
With hydrogenchloride; water Heating;54.6%
With hydrogenchloride; water
4'-chloropropiophenone
6285-05-8

4'-chloropropiophenone

lithium-bromoacetate

lithium-bromoacetate

4-(4-chlorophenyl)-3-methyl-4-oxobutanoic acid
52240-25-2

4-(4-chlorophenyl)-3-methyl-4-oxobutanoic acid

Conditions
ConditionsYield
4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

4-(4-chlorophenyl)-3-methyl-4-oxobutanoic acid
52240-25-2

4-(4-chlorophenyl)-3-methyl-4-oxobutanoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium cyanide / dimethylformamide / 2 h / 40 °C
2: 54.6 percent / conc. HCl, water / Heating
View Scheme
Multi-step reaction with 2 steps
1: sodium cyanide / N,N-dimethyl-formamide; methanol
2: hydrogenchloride; water
View Scheme
Multi-step reaction with 2 steps
1.1: N,N-dimethyl-formamide / 2 h / 35 - 38 °C / Inert atmosphere
1.2: 3.5 h / 40 °C / Inert atmosphere
2.1: hydrogenchloride; water / 5 h / 100 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1.1: sodium cyanide / N,N-dimethyl-formamide / 2 h / 35 - 38 °C / Inert atmosphere
1.2: 40 °C / Inert atmosphere
2.1: hydrogenchloride; water / 5 h / 100 °C / Inert atmosphere
View Scheme
4-(4-chlorophenyl)-3-methyl-4-oxobutanoic acid
52240-25-2

4-(4-chlorophenyl)-3-methyl-4-oxobutanoic acid

3-methyl-4-oxo-4-(3'-nitro-4'-chloro-phenyl)-butyric acid
85633-96-1

3-methyl-4-oxo-4-(3'-nitro-4'-chloro-phenyl)-butyric acid

Conditions
ConditionsYield
With nitric acid at -15 - -10℃; for 0.5h;98%
With nitric acid at -15 - -10℃; Inert atmosphere;90%
With nitric acid at -15 - -10℃; Inert atmosphere;90%
With nitric acid In water
4-(4-chlorophenyl)-3-methyl-4-oxobutanoic acid
52240-25-2

4-(4-chlorophenyl)-3-methyl-4-oxobutanoic acid

5-methyl-6-<2-(2-pyrrolyl)-5-benzimidazoyl>-2,3,4,5-tetrahydro-pyridazin-3-one

5-methyl-6-<2-(2-pyrrolyl)-5-benzimidazoyl>-2,3,4,5-tetrahydro-pyridazin-3-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 98 percent / nitric acid / 0.5 h / -15 - -10 °C
2: 98 percent / hydrazine hydrate / acetic acid / 2.5 h / 100 °C
3: 86 percent / butan-1-ol / 20 h / Heating
4: 88.6 percent / H2, 1N aq. HCL / 5percent Pd/C / methanol / 2 h
5: 32 percent / sodium bisulfite / dimethylformamide / 2 h / Heating
View Scheme
4-(4-chlorophenyl)-3-methyl-4-oxobutanoic acid
52240-25-2

4-(4-chlorophenyl)-3-methyl-4-oxobutanoic acid

5-methyl-6<2-(2-thiazolyl)-5-benzimidazoyl>-2,3,4,5-tetrahydro-pyridazin-3-one

5-methyl-6<2-(2-thiazolyl)-5-benzimidazoyl>-2,3,4,5-tetrahydro-pyridazin-3-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 98 percent / nitric acid / 0.5 h / -15 - -10 °C
2: 98 percent / hydrazine hydrate / acetic acid / 2.5 h / 100 °C
3: 86 percent / butan-1-ol / 20 h / Heating
4: 88.6 percent / H2, 1N aq. HCL / 5percent Pd/C / methanol / 2 h
5: 29 percent / sodium bisulfite / dimethylformamide / 2 h / Heating
View Scheme
4-(4-chlorophenyl)-3-methyl-4-oxobutanoic acid
52240-25-2

4-(4-chlorophenyl)-3-methyl-4-oxobutanoic acid

5-methyl-6-<2-(1,2,4-triazol-5-yl)-5-benzimidazoyl>-2,3,4,5-tetrahydro-pyridazin-3-one

5-methyl-6-<2-(1,2,4-triazol-5-yl)-5-benzimidazoyl>-2,3,4,5-tetrahydro-pyridazin-3-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 98 percent / nitric acid / 0.5 h / -15 - -10 °C
2: 98 percent / hydrazine hydrate / acetic acid / 2.5 h / 100 °C
3: 86 percent / butan-1-ol / 20 h / Heating
4: 88.6 percent / H2, 1N aq. HCL / 5percent Pd/C / methanol / 2 h
5: 25 percent / sodium bisulfite / dimethylformamide / 2 h / Heating
View Scheme
4-(4-chlorophenyl)-3-methyl-4-oxobutanoic acid
52240-25-2

4-(4-chlorophenyl)-3-methyl-4-oxobutanoic acid

5-methyl-6-<2-(5-<1-methyl>pyrazolyl)-5-benzimidazoyl>-2,3,4,5-tetrahydro-pyridazin-3-one

5-methyl-6-<2-(5-<1-methyl>pyrazolyl)-5-benzimidazoyl>-2,3,4,5-tetrahydro-pyridazin-3-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 98 percent / nitric acid / 0.5 h / -15 - -10 °C
2: 98 percent / hydrazine hydrate / acetic acid / 2.5 h / 100 °C
3: 86 percent / butan-1-ol / 20 h / Heating
4: 88.6 percent / H2, 1N aq. HCL / 5percent Pd/C / methanol / 2 h
5: 68 percent / sodium bisulfite / dimethylformamide / 2 h / Heating
View Scheme
4-(4-chlorophenyl)-3-methyl-4-oxobutanoic acid
52240-25-2

4-(4-chlorophenyl)-3-methyl-4-oxobutanoic acid

5-methyl-6-<2-(3-<1-methyl>pyrazolyl)-5-benzimidazoyl>-2,3,4,5-tetrahydro-pyridazin-3-one

5-methyl-6-<2-(3-<1-methyl>pyrazolyl)-5-benzimidazoyl>-2,3,4,5-tetrahydro-pyridazin-3-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 98 percent / nitric acid / 0.5 h / -15 - -10 °C
2: 98 percent / hydrazine hydrate / acetic acid / 2.5 h / 100 °C
3: 86 percent / butan-1-ol / 20 h / Heating
4: 88.6 percent / H2, 1N aq. HCL / 5percent Pd/C / methanol / 2 h
5: 54 percent / sodium bisulfite / dimethylformamide / 2 h / Heating
View Scheme
4-(4-chlorophenyl)-3-methyl-4-oxobutanoic acid
52240-25-2

4-(4-chlorophenyl)-3-methyl-4-oxobutanoic acid

5-methyl-6-<2-(2-<5-chlorothienyl>)-5-benzimidazoyl>-2,3,4,5-tetrahydro-pyridazin-3-one

5-methyl-6-<2-(2-<5-chlorothienyl>)-5-benzimidazoyl>-2,3,4,5-tetrahydro-pyridazin-3-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 98 percent / nitric acid / 0.5 h / -15 - -10 °C
2: 98 percent / hydrazine hydrate / acetic acid / 2.5 h / 100 °C
3: 86 percent / butan-1-ol / 20 h / Heating
4: 88.6 percent / H2, 1N aq. HCL / 5percent Pd/C / methanol / 2 h
5: 35 percent / sodium bisulfite / dimethylformamide / 2 h / Heating
View Scheme
4-(4-chlorophenyl)-3-methyl-4-oxobutanoic acid
52240-25-2

4-(4-chlorophenyl)-3-methyl-4-oxobutanoic acid

6-(3,4-diaminophenyl)-5-methyl-2,3,4,5-tetrahydropyridazin-3-one
136609-85-3, 136609-86-4, 74150-02-0

6-(3,4-diaminophenyl)-5-methyl-2,3,4,5-tetrahydropyridazin-3-one

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 98 percent / nitric acid / 0.5 h / -15 - -10 °C
2: 98 percent / hydrazine hydrate / acetic acid / 2.5 h / 100 °C
3: 86 percent / butan-1-ol / 20 h / Heating
4: 88.6 percent / H2, 1N aq. HCL / 5percent Pd/C / methanol / 2 h
View Scheme
Multi-step reaction with 4 steps
1: nitric acid / water
2: hydrazine hydrate; acetic acid / water
3: butan-1-ol; water
4: hydrogenchloride; hydrogen / palladium on carbon / water; methanol
View Scheme
Multi-step reaction with 4 steps
1: nitric acid / -15 - -10 °C / Inert atmosphere
2: hydrazine hydrate; acetic acid / 30 - 100 °C / Inert atmosphere
3: L-proline; sodium carbonate; sodium azide; sodium L-ascorbate; copper(ll) sulfate pentahydrate / dimethyl sulfoxide; water / 24 h / 70 °C / Inert atmosphere
4: sodium hydrogensulfide / water; methanol / 6 h / 65 °C / Inert atmosphere
View Scheme
Multi-step reaction with 4 steps
1: nitric acid / -15 - -10 °C / Inert atmosphere
2: acetic acid; hydrazine hydrate / 4.5 h / 30 - 100 °C / Inert atmosphere
3: sodium carbonate; sodium azide; sodium L-ascorbate; L-proline; copper(ll) sulfate pentahydrate / dimethyl sulfoxide; water / 24 h / 70 °C / Inert atmosphere
4: sodium hydrogensulfide / water; methanol / 6 h / 65 °C / Inert atmosphere
View Scheme
4-(4-chlorophenyl)-3-methyl-4-oxobutanoic acid
52240-25-2

4-(4-chlorophenyl)-3-methyl-4-oxobutanoic acid

(+)-6-(3,4-diaminophenyl)-5-methyl-2,3,4,5-tetrahydro-pyridazin-3-one

(+)-6-(3,4-diaminophenyl)-5-methyl-2,3,4,5-tetrahydro-pyridazin-3-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 98 percent / nitric acid / 0.5 h / -15 - -10 °C
3: hydrazine hydrate / acetic acid / 2.5 h / 100 °C
4: butan-1-ol / 20 h / Heating
5: H2, 1N aq. HCL / 5percent Pd/C / methanol / 2 h
View Scheme
4-(4-chlorophenyl)-3-methyl-4-oxobutanoic acid
52240-25-2

4-(4-chlorophenyl)-3-methyl-4-oxobutanoic acid

(-)-6-(3,4-diaminophenyl)-5-methyl-2,3,4,5-tetrahydro-pyridazin-3-one

(-)-6-(3,4-diaminophenyl)-5-methyl-2,3,4,5-tetrahydro-pyridazin-3-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 98 percent / nitric acid / 0.5 h / -15 - -10 °C
3: hydrazine hydrate / acetic acid / 2.5 h / 100 °C
4: butan-1-ol / 20 h / Heating
5: H2, 1N aq. HCL / 5percent Pd/C / methanol / 2 h
View Scheme
4-(4-chlorophenyl)-3-methyl-4-oxobutanoic acid
52240-25-2

4-(4-chlorophenyl)-3-methyl-4-oxobutanoic acid

(+)-4-(4-chloro-3-nitrophenyl)-3-methyl-4-oxobutyric acid
151911-11-4

(+)-4-(4-chloro-3-nitrophenyl)-3-methyl-4-oxobutyric acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 98 percent / nitric acid / 0.5 h / -15 - -10 °C
View Scheme
4-(4-chlorophenyl)-3-methyl-4-oxobutanoic acid
52240-25-2

4-(4-chlorophenyl)-3-methyl-4-oxobutanoic acid

(-)-4-(4-chloro-3-nitrophenyl)-3-methyl-4-oxobutyric acid
136609-87-5

(-)-4-(4-chloro-3-nitrophenyl)-3-methyl-4-oxobutyric acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 98 percent / nitric acid / 0.5 h / -15 - -10 °C
View Scheme
4-(4-chlorophenyl)-3-methyl-4-oxobutanoic acid
52240-25-2

4-(4-chlorophenyl)-3-methyl-4-oxobutanoic acid

6-(4-chloro-3-nitrophenyl)-5-methyl-2,3,4,5-tetrahydropyridazin-3-one
117397-88-3, 136609-88-6, 151870-45-0

6-(4-chloro-3-nitrophenyl)-5-methyl-2,3,4,5-tetrahydropyridazin-3-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 98 percent / nitric acid / 0.5 h / -15 - -10 °C
2: 98 percent / hydrazine hydrate / acetic acid / 2.5 h / 100 °C
View Scheme
Multi-step reaction with 2 steps
1: nitric acid / water
2: hydrazine hydrate; acetic acid / water
View Scheme
Multi-step reaction with 2 steps
1: nitric acid / -15 - -10 °C / Inert atmosphere
2: hydrazine hydrate; acetic acid / 30 - 100 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: nitric acid / -15 - -10 °C / Inert atmosphere
2: acetic acid; hydrazine hydrate / 4.5 h / 30 - 100 °C / Inert atmosphere
View Scheme
4-(4-chlorophenyl)-3-methyl-4-oxobutanoic acid
52240-25-2

4-(4-chlorophenyl)-3-methyl-4-oxobutanoic acid

(+)-6-(4-chloro-3-nitrophenyl)-5-methyl-2,3,4,5-tetrahydropyridazin-3-one

(+)-6-(4-chloro-3-nitrophenyl)-5-methyl-2,3,4,5-tetrahydropyridazin-3-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 98 percent / nitric acid / 0.5 h / -15 - -10 °C
3: hydrazine hydrate / acetic acid / 2.5 h / 100 °C
View Scheme
4-(4-chlorophenyl)-3-methyl-4-oxobutanoic acid
52240-25-2

4-(4-chlorophenyl)-3-methyl-4-oxobutanoic acid

(-)-6-(4-chloro-3-nitrophenyl)-5-methyl-2,3,4,5-tetrahydropyridazin-3-one

(-)-6-(4-chloro-3-nitrophenyl)-5-methyl-2,3,4,5-tetrahydropyridazin-3-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 98 percent / nitric acid / 0.5 h / -15 - -10 °C
3: hydrazine hydrate / acetic acid / 2.5 h / 100 °C
View Scheme
4-(4-chlorophenyl)-3-methyl-4-oxobutanoic acid
52240-25-2

4-(4-chlorophenyl)-3-methyl-4-oxobutanoic acid

5-methyl-6-<2-(3-thienyl)-5-benzimidazoyl>-2,3,4,5-tetrahydro-pyridazin-3-one

5-methyl-6-<2-(3-thienyl)-5-benzimidazoyl>-2,3,4,5-tetrahydro-pyridazin-3-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 98 percent / nitric acid / 0.5 h / -15 - -10 °C
2: 98 percent / hydrazine hydrate / acetic acid / 2.5 h / 100 °C
3: 86 percent / butan-1-ol / 20 h / Heating
4: 88.6 percent / H2, 1N aq. HCL / 5percent Pd/C / methanol / 2 h
5: sodium bisulfite / dimethylformamide / 2 h / Heating
View Scheme
4-(4-chlorophenyl)-3-methyl-4-oxobutanoic acid
52240-25-2

4-(4-chlorophenyl)-3-methyl-4-oxobutanoic acid

5-methyl-6-<2-(2-furyl)-5-benzimidazoyl>-2,3,4,5-tetrahydro-pyridazin-3-one

5-methyl-6-<2-(2-furyl)-5-benzimidazoyl>-2,3,4,5-tetrahydro-pyridazin-3-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 98 percent / nitric acid / 0.5 h / -15 - -10 °C
2: 98 percent / hydrazine hydrate / acetic acid / 2.5 h / 100 °C
3: 86 percent / butan-1-ol / 20 h / Heating
4: 88.6 percent / H2, 1N aq. HCL / 5percent Pd/C / methanol / 2 h
5: sodium bisulfite / dimethylformamide / 2 h / Heating
View Scheme
4-(4-chlorophenyl)-3-methyl-4-oxobutanoic acid
52240-25-2

4-(4-chlorophenyl)-3-methyl-4-oxobutanoic acid

5-methyl-6-<2-(2-thienyl)-5-benzimidazoyl>-2,3,4,5-tetrahydro-pyridazin-3-one

5-methyl-6-<2-(2-thienyl)-5-benzimidazoyl>-2,3,4,5-tetrahydro-pyridazin-3-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 98 percent / nitric acid / 0.5 h / -15 - -10 °C
2: 98 percent / hydrazine hydrate / acetic acid / 2.5 h / 100 °C
3: 86 percent / butan-1-ol / 20 h / Heating
4: 88.6 percent / H2, 1N aq. HCL / 5percent Pd/C / methanol / 2 h
5: sodium bisulfite / dimethylformamide / 2 h / Heating
View Scheme
4-(4-chlorophenyl)-3-methyl-4-oxobutanoic acid
52240-25-2

4-(4-chlorophenyl)-3-methyl-4-oxobutanoic acid

5-methyl-6-<2-(4-thiazolyl)-5-benzimidazoyl>-2,3,4,5-tetrahydro-pyridazin-3-one

5-methyl-6-<2-(4-thiazolyl)-5-benzimidazoyl>-2,3,4,5-tetrahydro-pyridazin-3-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 98 percent / nitric acid / 0.5 h / -15 - -10 °C
2: 98 percent / hydrazine hydrate / acetic acid / 2.5 h / 100 °C
3: 86 percent / butan-1-ol / 20 h / Heating
4: 88.6 percent / H2, 1N aq. HCL / 5percent Pd/C / methanol / 2 h
5: sodium bisulfite / dimethylformamide / 2 h / Heating
View Scheme
4-(4-chlorophenyl)-3-methyl-4-oxobutanoic acid
52240-25-2

4-(4-chlorophenyl)-3-methyl-4-oxobutanoic acid

5-methyl-6-<2-(3-pyrazolyl)-5-benzimidazolyl>-2,3,4,5-tetrahydro-pyridazin-3-one

5-methyl-6-<2-(3-pyrazolyl)-5-benzimidazolyl>-2,3,4,5-tetrahydro-pyridazin-3-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 98 percent / nitric acid / 0.5 h / -15 - -10 °C
2: 98 percent / hydrazine hydrate / acetic acid / 2.5 h / 100 °C
3: 86 percent / butan-1-ol / 20 h / Heating
4: 88.6 percent / H2, 1N aq. HCL / 5percent Pd/C / methanol / 2 h
5: 84 percent / sodium bisulfite / dimethylformamide / 2 h / Heating
View Scheme
4-(4-chlorophenyl)-3-methyl-4-oxobutanoic acid
52240-25-2

4-(4-chlorophenyl)-3-methyl-4-oxobutanoic acid

(-)-5-methyl-6-<2-(3-pyrazolyl)-5-benzimidazoyl>-2,3,4,5-tetrahydro-pyridazin-3-one

(-)-5-methyl-6-<2-(3-pyrazolyl)-5-benzimidazoyl>-2,3,4,5-tetrahydro-pyridazin-3-one

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 98 percent / nitric acid / 0.5 h / -15 - -10 °C
3: hydrazine hydrate / acetic acid / 2.5 h / 100 °C
4: butan-1-ol / 20 h / Heating
5: H2, 1N aq. HCL / 5percent Pd/C / methanol / 2 h
6: sodium bisulfite / dimethylformamide / 2 h / Heating
View Scheme
4-(4-chlorophenyl)-3-methyl-4-oxobutanoic acid
52240-25-2

4-(4-chlorophenyl)-3-methyl-4-oxobutanoic acid

(+)-5-methyl-6-<2-(3-pyrazolyl)-5-benzimidazoyl>-2,3,4,5-tetrahydro-pyridazin-3-one

(+)-5-methyl-6-<2-(3-pyrazolyl)-5-benzimidazoyl>-2,3,4,5-tetrahydro-pyridazin-3-one

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 98 percent / nitric acid / 0.5 h / -15 - -10 °C
3: hydrazine hydrate / acetic acid / 2.5 h / 100 °C
4: butan-1-ol / 20 h / Heating
5: H2, 1N aq. HCL / 5percent Pd/C / methanol / 2 h
6: sodium bisulfite / dimethylformamide / 2 h / Heating
View Scheme
4-(4-chlorophenyl)-3-methyl-4-oxobutanoic acid
52240-25-2

4-(4-chlorophenyl)-3-methyl-4-oxobutanoic acid

5-methyl-6<2-(4-pyrazolyl)-5-benzimidazoyl>-2,3,4,5-tetrahydro-pyridazin-3-one

5-methyl-6<2-(4-pyrazolyl)-5-benzimidazoyl>-2,3,4,5-tetrahydro-pyridazin-3-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 98 percent / nitric acid / 0.5 h / -15 - -10 °C
2: 98 percent / hydrazine hydrate / acetic acid / 2.5 h / 100 °C
3: 86 percent / butan-1-ol / 20 h / Heating
4: 88.6 percent / H2, 1N aq. HCL / 5percent Pd/C / methanol / 2 h
5: sodium bisulfite / dimethylformamide / 2 h / Heating
View Scheme
4-(4-chlorophenyl)-3-methyl-4-oxobutanoic acid
52240-25-2

4-(4-chlorophenyl)-3-methyl-4-oxobutanoic acid

5-methyl-6-<2-(2-<4-bromothienyl>)-5-benzimidazoyl>-2,3,4,5-tetrahydro-pyridazin-3-one

5-methyl-6-<2-(2-<4-bromothienyl>)-5-benzimidazoyl>-2,3,4,5-tetrahydro-pyridazin-3-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 98 percent / nitric acid / 0.5 h / -15 - -10 °C
2: 98 percent / hydrazine hydrate / acetic acid / 2.5 h / 100 °C
3: 86 percent / butan-1-ol / 20 h / Heating
4: 88.6 percent / H2, 1N aq. HCL / 5percent Pd/C / methanol / 2 h
5: sodium bisulfite / dimethylformamide / 2 h / Heating
View Scheme
4-(4-chlorophenyl)-3-methyl-4-oxobutanoic acid
52240-25-2

4-(4-chlorophenyl)-3-methyl-4-oxobutanoic acid

5-methyl-6-<2-(2-<5-bromothienyl>)-5-benzimidazoyl>-2,3,4,5-tetrahydro-pyridazin-3-one

5-methyl-6-<2-(2-<5-bromothienyl>)-5-benzimidazoyl>-2,3,4,5-tetrahydro-pyridazin-3-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 98 percent / nitric acid / 0.5 h / -15 - -10 °C
2: 98 percent / hydrazine hydrate / acetic acid / 2.5 h / 100 °C
3: 86 percent / butan-1-ol / 20 h / Heating
4: 88.6 percent / H2, 1N aq. HCL / 5percent Pd/C / methanol / 2 h
5: sodium bisulfite / dimethylformamide / 2 h / Heating
View Scheme
4-(4-chlorophenyl)-3-methyl-4-oxobutanoic acid
52240-25-2

4-(4-chlorophenyl)-3-methyl-4-oxobutanoic acid

5-methyl-6-<2-(3-<1,5-dimethyl>-pyrazolyl)-5-benzimidazoyl>-2,3,4,5-tetrahydro-pyridazin-3-one

5-methyl-6-<2-(3-<1,5-dimethyl>-pyrazolyl)-5-benzimidazoyl>-2,3,4,5-tetrahydro-pyridazin-3-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 98 percent / nitric acid / 0.5 h / -15 - -10 °C
2: 98 percent / hydrazine hydrate / acetic acid / 2.5 h / 100 °C
3: 86 percent / butan-1-ol / 20 h / Heating
4: 88.6 percent / H2, 1N aq. HCL / 5percent Pd/C / methanol / 2 h
5: sodium bisulfite / dimethylformamide / 2 h / Heating
View Scheme
4-(4-chlorophenyl)-3-methyl-4-oxobutanoic acid
52240-25-2

4-(4-chlorophenyl)-3-methyl-4-oxobutanoic acid

5-methyl-6-[3'-nitro-4'-benzylamino-phenyl]-4,5-dihydro-3(2H)-pyridazinone
77469-62-6, 136609-89-7, 151870-46-1

5-methyl-6-[3'-nitro-4'-benzylamino-phenyl]-4,5-dihydro-3(2H)-pyridazinone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 98 percent / nitric acid / 0.5 h / -15 - -10 °C
2: 98 percent / hydrazine hydrate / acetic acid / 2.5 h / 100 °C
3: 86 percent / butan-1-ol / 20 h / Heating
View Scheme
Multi-step reaction with 3 steps
1: nitric acid / water
2: hydrazine hydrate; acetic acid / water
3: butan-1-ol; water
View Scheme
Multi-step reaction with 4 steps
1.1: nitric acid / -15 - -10 °C / Inert atmosphere
2.1: hydrazine hydrate; acetic acid / 30 - 100 °C / Inert atmosphere
3.1: L-proline; sodium carbonate; sodium azide; sodium L-ascorbate; copper(ll) sulfate pentahydrate / dimethyl sulfoxide; water / 24 h / 70 °C / Inert atmosphere
4.1: acetic acid / 0.25 h / Inert atmosphere
4.2: 15.5 h / 10 - 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: nitric acid / -15 - -10 °C / Inert atmosphere
2.1: acetic acid; hydrazine hydrate / 4.5 h / 30 - 100 °C / Inert atmosphere
3.1: sodium carbonate; sodium azide; sodium L-ascorbate; L-proline; copper(ll) sulfate pentahydrate / dimethyl sulfoxide; water / 24 h / 70 °C / Inert atmosphere
4.1: acetic acid / 0.25 h / Inert atmosphere
4.2: 20 h / 10 °C / Inert atmosphere
View Scheme

52240-25-2Relevant articles and documents

Bio-based crotonic acid from polyhydroxybutyrate: synthesis and photocatalyzed hydroacylation

Fagnoni, Maurizio,Galletti, Paola,Jorea, Alexandra,Parodi, Adriano,Ravelli, Davide,Samorì, Chiara,Torri, Cristian

supporting information, p. 3420 - 3427 (2021/05/21)

A novel thermolytic distillation process was developed to depolymerize polyhydroxybutyrate (PHB) for the selective production of crotonic acid. The conditions adopted (170 °C, 150 mbar) were applied to pure PHB and PHB-enriched bacteria containing 60 and 30% of PHB, giving a recovery of crotonic acid of 92, 78 and 58%, respectively. The high efficiency of the developed process poses the basis for a drop-in production of bio-based crotonic acid, whose versatility as a platform chemical has been investigated through a photochemical approach. The photocatalytic addition (promoted by tetrabutylammonium decatungstate - TBADT) of aliphatic and aromatic aldehydes to crotonic acid took place under solar-simulated light irradiation. TBADT triggered thein situformation of valuable acyl radicals from the corresponding aldehydes, thus inducing the desired hydroacylationviaradical conjugate addition. Notably, the functionalization took place in a satisfactory yield quite independently of the adopted sample of crotonic acid (whether commercial or bio-based).

Synthesis of novel Pyridazinonylbenzotriazoles

Shashidhar Reddy,George Vineel,Venkataiah,Naidu,Dubey

, p. 3633 - 3638 (2015/12/30)

4-Chlorobenzaldehyde (1) was reacted with crotononitrile (2) in the presence of sodium cyanide yielding 4-(4-chlorophenyl)-3-methyl-4-oxobutyronitrile (3) which on refluxing with concentrated HCl gave 4-(4-chlorophenyl)-3-methyl-4-oxobutyric acid (4). The latter, on treatment with fuming nitric acid, yielded 4-(4-chloro-3-nitrophenyl)-3-methyl-4-oxobutyric acid (5), which on treatment with hydrazine hydrate gave 6-(4-chloro-3-nitrophenyl)-5-methyl-4,5-dihydro-2H-pyridazine-3-one (6). Azidation and reduction of 6 with sodium azide gave the amino derivative 7 which on reductive alkylation gave 10(a-i) followed by reduction with commercially available sodium hydrogen sulphide solution gave the substituted diamine derivative 11(a-i). The compound 7 directly undergoes reduction with sodium hydrogen sulphide yielding (8). Finally, 8 and 11(a-i) was converted into the target compounds by diazotized-cyclization with sodium nitrite giving pyridazinonylbenzotriazoles 9 and 12(a-i).

Synthesis and biological activities of meribendan and related heterocyclic benzimidazolo-pyridazinones

Jonas, R,Klockow, M,Lues, I,Pruecher, H,Schliep, H J,Wurziger, H

, p. 129 - 140 (2007/10/02)

The synthesis of a new heterocyclic benzimidazolo-pyridazinones is described.The new compounds were evaluated as inotropic agents with 'calcium-sensitizing' effects. 5-Methyl-6--2,3,4,5-tetrahydro-pyridazin-3-one hydrochloride (meribendan) turned out to be the most interesting compound and was chosen for development as a positive inotrope. benzimidazole / calcium sensivity / cardiotonics / inotropes / phosphodiesterase / papillary muscle / pyridazinone

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