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1821-12-1

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1821-12-1 Usage

Chemical Properties

4-Phenylbutyric acid is white to slightly yellowish crystalline powder. It is slightly soluble in chloroform and methanol. Its solubility in water is 5.3 g/l (at 40 °C).

Uses

4-Phenylbutyric acid is used as a chemical chaperone involved in protein-folding disorders. It is involved in the synthesis of dyes and an active pharmaceutical ingredient intermediate.

Definition

4-Phenylbutyric acid is a monocarboxylic acid the structure of which is that of butyric acid substituted with a phenyl group at C-4. It is a histone deacetylase inhibitor that displays anticancer activity. It inhibits cell proliferation, invasion and migration and induces apopto is in glioma cells. It also inhibits protein isoprenylation, depletes plasma glutamine, increases production of foetal haemoglobin through transcriptional activation of the gamma-globin gene and affects hPPARgamma activation.

Preparation

4-phenylbutyric acid is obtained by the reaction of benzene with butyrolactone in the presence of aluminum chloride, followed by neutralization with base.Synthesis of 4-phenylbutyric acid

Application

4-Phenylbutyric acid (4-PBA) is used in the treatment of urea cycle disorders under the trade name Buphenyl. 4-PBA has been used as a selective inhibitor of endoplasmic reticulum stress (ERS).4-Phenylbutyric acid is used as organic intermediates. It can also be used as a reactant in the synthesis of:1-Tetralone using Lewis acid catalyst.4,N-diphenylbutyramide.

Synthesis Reference(s)

Tetrahedron Letters, 32, p. 3309, 1991 DOI: 10.1016/S0040-4039(00)92693-5

General Description

4-Phenylbutyric acid (4-PBA) is a small-molecular-weight fatty acid with a terminal aromatic group, and its sodium salt (sodium 4-phenyl butyrate) has been used for the treatment of urea cycle disorders. This molecule is also used for the treatment of sickle cell diseases and thalassemia owing to its ability to activate β-globin transcription. Moreover, 4-PBA is employed as an orally bioavailable agent for the treatment of spinal muscular atrophy (SMA) and tumors. Neuroprotective Effects of 4-phenylbutyric Acid and Its Derivatives: Possible Therapeutics for Neurodegenerative Diseases

Purification Methods

Crystallise the acid from pet ether (b 40-60o). [Beilstein 9 IV 1811.]

Check Digit Verification of cas no

The CAS Registry Mumber 1821-12-1 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,8,2 and 1 respectively; the second part has 2 digits, 1 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 1821-12:
(6*1)+(5*8)+(4*2)+(3*1)+(2*1)+(1*2)=61
61 % 10 = 1
So 1821-12-1 is a valid CAS Registry Number.
InChI:InChI=1/C10H12O2/c11-10(12)8-4-7-9-5-2-1-3-6-9/h1-3,5-6H,4,7-8H2,(H,11,12)

1821-12-1 Well-known Company Product Price

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  • Alfa Aesar

  • (A18115)  4-Phenylbutyric acid, 99%   

  • 1821-12-1

  • 25g

  • 475.0CNY

  • Detail
  • Alfa Aesar

  • (A18115)  4-Phenylbutyric acid, 99%   

  • 1821-12-1

  • 100g

  • 1723.0CNY

  • Detail
  • Alfa Aesar

  • (A18115)  4-Phenylbutyric acid, 99%   

  • 1821-12-1

  • 500g

  • 7133.0CNY

  • Detail

1821-12-1SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-phenylbutyric acid

1.2 Other means of identification

Product number -
Other names 4-Phenylbutanoic acid

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:1821-12-1 SDS

1821-12-1Synthetic route

(Z)-1-chloro-4-phenylbut-1-en-1-yl acetate
852919-31-4

(Z)-1-chloro-4-phenylbut-1-en-1-yl acetate

4-Phenylbutyric acid
1821-12-1

4-Phenylbutyric acid

Conditions
ConditionsYield
With lithium hydroxide In tetrahydrofuran; water at 20℃; for 3h;100%
trans-styrylacetic acid
2243-53-0, 59744-46-6, 1914-58-5

trans-styrylacetic acid

4-Phenylbutyric acid
1821-12-1

4-Phenylbutyric acid

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen at 20℃; for 18h; Sealed tube;99%
With formaldehyd; palladium dichloride In sodium hydroxide at 65℃; Hydrogenation;98%
With palladium on activated charcoal; hydrogen In methanol at 20℃;78%
With hydroxylamine; Na3[Fe(CN)5NH3]*3H2O In 1,4-dioxane-d8; water-d2 at 80℃; pH=8;
4,5-dihydro-5-phenyl-2(3H)-furanone
1008-76-0

4,5-dihydro-5-phenyl-2(3H)-furanone

4-Phenylbutyric acid
1821-12-1

4-Phenylbutyric acid

Conditions
ConditionsYield
With palladium on activated carbon; hydrogen In methanol at 20℃; under 760.051 Torr; for 1h; Schlenk technique;99%
With palladium 10% on activated carbon; W(OTf)6; hydrogen at 50℃; under 760.051 Torr; for 12h;95%
With palladium on activated carbon; W(OTf)6; hydrogen In acetic acid at 50℃; under 760.051 Torr; for 12h;95%
With potassium fluoride; palladium diacetate; chlorobenzene In tetrahydrofuran; water at 20℃; for 1h; Inert atmosphere; chemoselective reaction;68%
6-phenylhexane-1,2,3-triol
1400695-43-3

6-phenylhexane-1,2,3-triol

4-Phenylbutyric acid
1821-12-1

4-Phenylbutyric acid

Conditions
ConditionsYield
With 1‐methyl‐2‐azaadamantane‐N‐oxyl; [bis(acetoxy)iodo]benzene; tetrabutylammomium bromide In water; acetonitrile at 0 - 20℃; for 2h; Inert atmosphere;99%
With 1‐methyl‐2‐azaadamantane‐N‐oxyl; sodium hypochlorite; sodium chlorite In aq. phosphate buffer; acetonitrile at 20℃; for 3h; pH=6.8; Inert atmosphere;96%
but-3-enoic acid
625-38-7

but-3-enoic acid

phenylboronic acid
98-80-6

phenylboronic acid

4-Phenylbutyric acid
1821-12-1

4-Phenylbutyric acid

Conditions
ConditionsYield
With propan-1-ol; bis(1,5-cyclooctadiene)nickel (0); potassium tert-butylate; 4,4-dibenzyl-2-(pyridin-2-yl)-4,5-dihydrooxazole at 60℃; Sealed tube; regioselective reaction;99%
Trifluoro-acetic acid 1-cyano-4-phenyl-1-(pyridin-2-ylsulfanyl)-butyl ester
144499-11-6

Trifluoro-acetic acid 1-cyano-4-phenyl-1-(pyridin-2-ylsulfanyl)-butyl ester

4-Phenylbutyric acid
1821-12-1

4-Phenylbutyric acid

Conditions
ConditionsYield
With potassium carbonate In water for 2h;98%
With potassium carbonate In acetone at 25℃; for 12h; Yield given;
2-(3-phenylpropyl)-1,3-dioxolane
313058-67-2

2-(3-phenylpropyl)-1,3-dioxolane

4-Phenylbutyric acid
1821-12-1

4-Phenylbutyric acid

Conditions
ConditionsYield
With Oxone; water In tetrahydrofuran at 0 - 20℃; for 12h; Hydrolysis; oxidation;98%
1-(6H-Phenanthridin-5-yl)-4-phenyl-butan-1-one
80554-69-4

1-(6H-Phenanthridin-5-yl)-4-phenyl-butan-1-one

A

phenanthridine
229-87-8

phenanthridine

B

4-Phenylbutyric acid
1821-12-1

4-Phenylbutyric acid

Conditions
ConditionsYield
With ammonium cerium(IV) nitrate In water; acetonitrile for 0.25h; Product distribution; deprotection;A n/a
B 97%
4-phenylbutyronitrile
2046-18-6

4-phenylbutyronitrile

4-Phenylbutyric acid
1821-12-1

4-Phenylbutyric acid

Conditions
ConditionsYield
enzyme from Synechocystis sp. PCC 6803 In phosphate buffer at 30℃; for 12h; pH=7.2;97%
With potassium phosphate buffer at 30℃; for 24h; Rhodococcus sp. AJ270 cells;89.2%
With dipotassium hydrogenphosphate; phosphoric acid; water; nitrile aminohydrolase E.C. 3.5.5.1 at 25℃; pH=7.50; Thermodynamic data;
4-phenyl-N-(quinolin-8-yl)butanamide
1449300-08-6

4-phenyl-N-(quinolin-8-yl)butanamide

4-Phenylbutyric acid
1821-12-1

4-Phenylbutyric acid

Conditions
ConditionsYield
With sodium hydroxide In ethanol at 130℃; for 16h;97%
Stage #1: 4-phenyl-N-(quinolin-8-yl)butanamide With ozone In dichloromethane at -78℃;
Stage #2: With dimethylsulfide
Stage #3: With dihydrogen peroxide; lithium hydroxide In tetrahydrofuran; water
79%
succinylbenzene
2051-95-8

succinylbenzene

4-Phenylbutyric acid
1821-12-1

4-Phenylbutyric acid

Conditions
ConditionsYield
Stage #1: succinylbenzene With hydrazine hydrate In diethylene glycol at 25℃; for 0.5h; Wolff-Kishner Reduction;
Stage #2: With potassium hydroxide In diethylene glycol at 120 - 245℃; for 4.5h;
95%
With potassium hydroxide; hydrazine hydrate In diethylene glycol for 0.416667h; Wolff-Kishner reduction; Irradiation;90%
With hydrogenchloride; mercury dichloride; zinc In toluene for 30h; Heating;89%
4-phenyl-butan-1-ol
3360-41-6

4-phenyl-butan-1-ol

4-Phenylbutyric acid
1821-12-1

4-Phenylbutyric acid

Conditions
ConditionsYield
With air; potassium carbonate In water at 46.84℃; for 24h;95%
Stage #1: 4-phenyl-butan-1-ol With Oxone; sodium ortho-iodobenzenesulfonate In acetonitrile at 70℃; for 1h;
Stage #2: With water In acetonitrile for 5h;
94%
With potassium peroxymonosulfate; 2-Iodo-5-methylbenzenesulfonic acid In nitromethane at 70℃; for 8h;94%
methyl 3-(benzyl)propanoate
2046-17-5

methyl 3-(benzyl)propanoate

4-Phenylbutyric acid
1821-12-1

4-Phenylbutyric acid

Conditions
ConditionsYield
With ethanol; sodium hydroxide at 50 - 60℃; for 0.666667h; Reagent/catalyst; Green chemistry; Large scale;94.4%
With sodium hydroxide In ethanol at 50 - 60℃; for 0.666667h; Large scale;94.4%
With sodium hydroxide In acetone at 25℃; Kinetics; Thermodynamic data; other temp., ΔH excit., ΔS excit.;
4-butanolide
96-48-0

4-butanolide

benzene
71-43-2

benzene

4-Phenylbutyric acid
1821-12-1

4-Phenylbutyric acid

Conditions
ConditionsYield
Stage #1: 4-butanolide; benzene; aluminum (III) chloride In benzene at 50 - 60℃; for 1.5h;
Stage #2: With sodium hydroxide In water at 35℃; for 2h; pH=9 - 9.5;
Stage #3: With hydrogenchloride In water
93.7%
With aluminium trichloride Product distribution; degree of isomerization of the alkyl chain;100 % Chromat.
α-(trichloromethyl)benzenepropanol
82772-38-1

α-(trichloromethyl)benzenepropanol

4-Phenylbutyric acid
1821-12-1

4-Phenylbutyric acid

Conditions
ConditionsYield
Stage #1: α-(trichloromethyl)benzenepropanol With sodium hydroxide In tert-butyl alcohol at 30℃; for 0.166667h;
Stage #2: With sodium tetrahydroborate In tert-butyl alcohol
93%
With sodium tetrahydroborate; diphenylselenide; sodium hydroxide In ethanol at 0 - 40℃; Inert atmosphere;90%
2-(3-phenylpropylidene)-1,3-dithiane 1-oxide
1253039-07-4

2-(3-phenylpropylidene)-1,3-dithiane 1-oxide

4-Phenylbutyric acid
1821-12-1

4-Phenylbutyric acid

Conditions
ConditionsYield
With hydrogenchloride In water; acetonitrile at 55 - 65℃; for 6h;91%
Phosphoric acid 1-cyano-4-phenyl-1-(pyridin-2-ylsulfanyl)-butyl ester dimethyl ester
144499-12-7

Phosphoric acid 1-cyano-4-phenyl-1-(pyridin-2-ylsulfanyl)-butyl ester dimethyl ester

4-Phenylbutyric acid
1821-12-1

4-Phenylbutyric acid

Conditions
ConditionsYield
With potassium hydroxide90%
Trimethyl-(4-phenyl-butoxy)-silane
81631-80-3

Trimethyl-(4-phenyl-butoxy)-silane

4-Phenylbutyric acid
1821-12-1

4-Phenylbutyric acid

Conditions
ConditionsYield
With N-hydroxyphthalimide; oxygen; cobalt(II) benzoate In acetonitrile at 20℃; for 12h;90%
ethyl 2-(ethoxycarbonyl)-4-phenylbutanoate
6628-68-8

ethyl 2-(ethoxycarbonyl)-4-phenylbutanoate

4-Phenylbutyric acid
1821-12-1

4-Phenylbutyric acid

Conditions
ConditionsYield
With hydrogenchloride In water; acetic acid at 95 - 110℃; for 20h; Heating / reflux;90%
Multi-step reaction with 2 steps
1: KOH-solution
2: Erhitzen
View Scheme
Stage #1: ethyl 2-(ethoxycarbonyl)-4-phenylbutanoate With hydrogenchloride; water In acetic acid at 95 - 110℃; for 20h;
Stage #2: With sodium hydroxide In water
Stage #3: With hydrogenchloride In water pH=1; Product distribution / selectivity;
Acetic acid 1-cyano-4-phenyl-1-(pyridin-2-ylsulfanyl)-butyl ester
144499-13-8

Acetic acid 1-cyano-4-phenyl-1-(pyridin-2-ylsulfanyl)-butyl ester

4-Phenylbutyric acid
1821-12-1

4-Phenylbutyric acid

Conditions
ConditionsYield
With potassium carbonate In water89%
With potassium carbonate In acetone at 25℃; for 12h; Yield given;
1-iodo-butane
542-69-8

1-iodo-butane

2-(6-(2-methoxyethyl)pyridyl) 4-phenylbutanoate
78427-99-3

2-(6-(2-methoxyethyl)pyridyl) 4-phenylbutanoate

A

1-phenyloctan-4-one
78427-96-0

1-phenyloctan-4-one

B

4-Phenylbutyric acid
1821-12-1

4-Phenylbutyric acid

Conditions
ConditionsYield
With nickel dichloride; zinc In N,N-dimethyl-formamide at 50℃; for 5h;A 87%
B 10%
Phosphoric acid 1-benzenesulfonyl-4-phenyl-1-(pyridin-2-ylsulfanyl)-butyl ester dimethyl ester
135967-12-3

Phosphoric acid 1-benzenesulfonyl-4-phenyl-1-(pyridin-2-ylsulfanyl)-butyl ester dimethyl ester

4-Phenylbutyric acid
1821-12-1

4-Phenylbutyric acid

Conditions
ConditionsYield
With potassium hydroxide87%
With potassium hydroxide In methanol Yield given;
tert-butyldimethylsilyl 4-phenylbutyl ether
72064-43-8

tert-butyldimethylsilyl 4-phenylbutyl ether

4-Phenylbutyric acid
1821-12-1

4-Phenylbutyric acid

Conditions
ConditionsYield
With N-hydroxyphthalimide; oxygen; cobalt(II) benzoate In acetonitrile at 20℃; for 15h;86%
1-chloro 4-iodobutane
10297-05-9

1-chloro 4-iodobutane

2-(6-(2-methoxyethyl)pyridyl) 4-phenylbutanoate
78427-99-3

2-(6-(2-methoxyethyl)pyridyl) 4-phenylbutanoate

A

8-Chloro-1-phenyl-octan-4-one
78429-24-0

8-Chloro-1-phenyl-octan-4-one

B

4-Phenylbutyric acid
1821-12-1

4-Phenylbutyric acid

Conditions
ConditionsYield
With nickel dichloride; zinc In N,N-dimethyl-formamide at 50℃; for 1h;A 85%
B 9%
4-phenyl-1-iodobutane
64283-87-0

4-phenyl-1-iodobutane

2-(6-(2-methoxyethyl)pyridyl) 4-phenylbutanoate
78427-99-3

2-(6-(2-methoxyethyl)pyridyl) 4-phenylbutanoate

A

1,8-diphenyloctan-4-one
78429-20-6

1,8-diphenyloctan-4-one

B

4-Phenylbutyric acid
1821-12-1

4-Phenylbutyric acid

Conditions
ConditionsYield
With nickel dichloride; zinc In N,N-dimethyl-formamide at 50℃; for 5h;A 85%
B 10%
4-phenyl-butyric acid 3-methyl-but-2-enyl ester

4-phenyl-butyric acid 3-methyl-but-2-enyl ester

4-Phenylbutyric acid
1821-12-1

4-Phenylbutyric acid

Conditions
ConditionsYield
With ytterbium(III) triflate In nitromethane for 9h; Ambient temperature;85%
4-iodobutyrophenone
65488-05-3

4-iodobutyrophenone

2-(6-(2-methoxyethyl)pyridyl) 4-phenylbutanoate
78427-99-3

2-(6-(2-methoxyethyl)pyridyl) 4-phenylbutanoate

A

1,8-Diphenyl-octane-1,5-dione
78429-23-9

1,8-Diphenyl-octane-1,5-dione

B

4-Phenylbutyric acid
1821-12-1

4-Phenylbutyric acid

Conditions
ConditionsYield
With nickel dichloride; zinc In N,N-dimethyl-formamide at 50℃; for 5h;A 84%
B 10%
2-iodooctane
36049-78-2, 557-36-8

2-iodooctane

2-(6-(2-methoxyethyl)pyridyl) 4-phenylbutanoate
78427-99-3

2-(6-(2-methoxyethyl)pyridyl) 4-phenylbutanoate

A

5-methyl-1-phenylundecan-4-one
78429-21-7

5-methyl-1-phenylundecan-4-one

B

4-Phenylbutyric acid
1821-12-1

4-Phenylbutyric acid

Conditions
ConditionsYield
With nickel dichloride; zinc In N,N-dimethyl-formamide at 50℃; for 5h;A 83%
B 9%
7-phenylheptane-2,4-dione
17424-49-6

7-phenylheptane-2,4-dione

4-Phenylbutyric acid
1821-12-1

4-Phenylbutyric acid

Conditions
ConditionsYield
With ammonium cerium(IV) nitrate In acetonitrile at 20℃; for 4h;83%
4-phenyl-butan-1-ol
3360-41-6

4-phenyl-butan-1-ol

A

3-benzyl propionaldehyde
18328-11-5

3-benzyl propionaldehyde

B

4-Phenylbutyric acid
1821-12-1

4-Phenylbutyric acid

Conditions
ConditionsYield
With tert.-butylnitrite; 2-azatricyclo[3.3.1.13,7]dec-2-yloxidanyl; oxygen; magnesium sulfate In acetonitrile at 50℃; for 2h; Reagent/catalyst; chemoselective reaction;A 83%
B 10%
tryptamine
61-54-1

tryptamine

4-Phenylbutyric acid
1821-12-1

4-Phenylbutyric acid

N-(2-(1H-indol-3-yl)ethyl)-4-phenylbutanamide
102181-30-6

N-(2-(1H-indol-3-yl)ethyl)-4-phenylbutanamide

Conditions
ConditionsYield
With Trimethyl borate In acetonitrile at 80℃; for 15h;100%
With tris(2,2,2-trifluoroethyl) borate In acetonitrile at 80℃; for 15h;70%
at 180℃;
ethanol
64-17-5

ethanol

4-Phenylbutyric acid
1821-12-1

4-Phenylbutyric acid

ethyl 4-phenylbutyrate
10031-93-3

ethyl 4-phenylbutyrate

Conditions
ConditionsYield
With thionyl chloride for 4h; Heating;100%
With sulfuric acid Reflux;96%
With sulfuric acid for 2h;93%
4-Phenylbutyric acid
1821-12-1

4-Phenylbutyric acid

phenylbutyric acid chloride
18496-54-3

phenylbutyric acid chloride

Conditions
ConditionsYield
With thionyl chloride; N,N-dimethyl-formamide In dichloromethane at 23℃;100%
With pyridine; thionyl chloride at 20 - 40℃; for 1.5h;98%
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere; Schlenk technique;98%
4-Phenylbutyric acid
1821-12-1

4-Phenylbutyric acid

3,4-dihydronaphthalene-1(2H)-one
529-34-0

3,4-dihydronaphthalene-1(2H)-one

Conditions
ConditionsYield
With tetrachlorosilane; 4-(trifluoromethyl)benzoic anhydride; silver perchlorate In dichloromethane for 24h; Ambient temperature;100%
With tetrachlorosilane; 4-(trifluoromethyl)benzoic anhydride; silver perchlorate In dichloromethane for 24h; Ambient temperature;100%
With trifluorormethanesulfonic acid at 5 - 20℃; for 2h; Cyclization; acylation;98%
rac-methylbenzylamine
618-36-0

rac-methylbenzylamine

4-Phenylbutyric acid
1821-12-1

4-Phenylbutyric acid

A

N-Octyl-4-phenyl-butyramide
78172-93-7

N-Octyl-4-phenyl-butyramide

B

N-benzyl-N-methyl-4-phenylbutanamide
78172-94-8

N-benzyl-N-methyl-4-phenylbutanamide

C

4-phenyl-N-(1-phenylethyl)butanamide
75056-45-0

4-phenyl-N-(1-phenylethyl)butanamide

Conditions
ConditionsYield
With potassium hydroxide; bis(o-nitrophenyl)phenylphosphonate; tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate other amines; multistep reaction;A 88%
B 95%
C 100%
4-Phenylbutyric acid
1821-12-1

4-Phenylbutyric acid

<γ,γ-D2>Benzolbutansaeure
51086-46-5

<γ,γ-D2>Benzolbutansaeure

Conditions
ConditionsYield
With hydrogen; water-d2; palladium on activated charcoal at 50℃; for 24h;100%
With palladium 10% on activated carbon; hydrogen; water-d2 at 50℃; under 760.051 Torr; for 12h;84%
With water-d2; sodium carbonate; Raney Co-Al at 90℃; for 2h;
With palladium 10% on activated carbon; hydrogen; water-d2 at 50℃; under 760.051 Torr; for 12h; Inert atmosphere;
With palladium 10% on activated carbon; hydrogen; water-d2 at 50℃; for 24h; Schlenk technique;
4-Phenylbutyric acid
1821-12-1

4-Phenylbutyric acid

benzyl alcohol
100-51-6

benzyl alcohol

benzyl 4-phenylbutanoate
77100-93-7

benzyl 4-phenylbutanoate

Conditions
ConditionsYield
With [Cl(C6F13C2H4)2SnOSn(C2H4C6F13)2Cl]2 In various solvent(s) at 150℃; for 10h;100%
tetrachlorobis(tetrahydrofuran)hafnium(IV) In toluene for 18h; Heating;99%
With Iron(III) isopropoxide; N-butylpyridinium bis(trifluoromethanesulfonyl)imide; zirconium(IV) tetraisopropoxide In n-heptane for 8h; Kinetics; Product distribution; Further Variations:; Reagents; Solvents; Catalysts; Heating;99%
4-Phenylbutyric acid
1821-12-1

4-Phenylbutyric acid

cyclohexanol
108-93-0

cyclohexanol

cyclohexyl 4-phenylbutyrate

cyclohexyl 4-phenylbutyrate

Conditions
ConditionsYield
With silica gel-immobilized perchloric acid at 80℃; for 5h; Fischer esterification; Inert atmosphere; Neat (no solvent);100%
tetrachlorobis(tetrahydrofuran)hafnium(IV) In toluene for 5h; Heating;94%
With molecualar sevies 4A; tetrachlorobis(tetrahydrofuran)hafnium(IV) In toluene at 120℃; for 5h;94%
4-Phenylbutyric acid
1821-12-1

4-Phenylbutyric acid

4-(cyclohexa-1,4-dien-1-yl)butanoic acid
663914-93-0

4-(cyclohexa-1,4-dien-1-yl)butanoic acid

Conditions
ConditionsYield
With ammonia; lithium In tert-butyl alcohol at -78℃; for 5h; Inert atmosphere;100%
With ammonia; lithium; tert-butyl alcohol at -78℃; for 5h;100%
With ethanol; sodium In diethyl ether; ammonia at -78℃;86%
4-Phenylbutyric acid
1821-12-1

4-Phenylbutyric acid

1-[(R)-1-(tert-butyldimethylsilyloxy)-4-(6-aminoindol-1-yl)-2-butyl]imidazole-4-carboxamide
294862-31-0

1-[(R)-1-(tert-butyldimethylsilyloxy)-4-(6-aminoindol-1-yl)-2-butyl]imidazole-4-carboxamide

1-[(R)-1-(tert-butyldimethylsilyloxy)-4-(6-(4-phenylbutyrylamino)indol-1-yl)-2-butyl]imidazole-4-carboxamide
294862-36-5

1-[(R)-1-(tert-butyldimethylsilyloxy)-4-(6-(4-phenylbutyrylamino)indol-1-yl)-2-butyl]imidazole-4-carboxamide

Conditions
ConditionsYield
Stage #1: 4-Phenylbutyric acid With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 20℃; for 0.666667h;
Stage #2: 1-[(R)-1-(tert-butyldimethylsilyloxy)-4-(6-aminoindol-1-yl)-2-butyl]imidazole-4-carboxamide In dichloromethane at 20℃; for 4h;
100%
4-Phenylbutyric acid
1821-12-1

4-Phenylbutyric acid

3-hydroxy-2-methyl-1-propene
513-42-8

3-hydroxy-2-methyl-1-propene

2-methyl-2-propen-1-yl 4-phenylbutyrate

2-methyl-2-propen-1-yl 4-phenylbutyrate

Conditions
ConditionsYield
With dimesitylammonium pentafluorobenzenesulfonate In n-heptane at 80℃; for 3h;100%
With Iron(III) isopropoxide; zirconium(IV) tetraisopropoxide In n-heptane for 15h;99%
dimesitylammonium pentafluorobenzenesulfonate In n-heptane at 80℃; for 3h; Product distribution / selectivity;99%
4-Phenylbutyric acid
1821-12-1

4-Phenylbutyric acid

(2R,3S,4R,5R)-2-[(E)-3-aminoprop-1-enyl]-5-(6-amino-9H-purin-9-yl)tetrahydrofuran-3,4-diol
390381-60-9

(2R,3S,4R,5R)-2-[(E)-3-aminoprop-1-enyl]-5-(6-amino-9H-purin-9-yl)tetrahydrofuran-3,4-diol

N-{(E)-3-[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]prop-2-enyl}-2-(1H-indol-3-yl)-4-phenylbutyramide

N-{(E)-3-[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]prop-2-enyl}-2-(1H-indol-3-yl)-4-phenylbutyramide

Conditions
ConditionsYield
Stage #1: 4-Phenylbutyric acid With dmap; N-ethyl-N,N-diisopropylamine; diisopropyl-carbodiimide In tetrahydrofuran at 20℃; for 24h;
Stage #2: With N-ethyl-N,N-diisopropylamine; cyanomethyl bromide In 1-methyl-pyrrolidin-2-one
Stage #3: (2R,3S,4R,5R)-2-[(E)-3-aminoprop-1-enyl]-5-(6-amino-9H-purin-9-yl)tetrahydrofuran-3,4-diol In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 20℃;
100%
4-Phenylbutyric acid
1821-12-1

4-Phenylbutyric acid

methyl iodide
74-88-4

methyl iodide

methyl 3-(benzyl)propanoate
2046-17-5

methyl 3-(benzyl)propanoate

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile for 8h; Heating;100%
5-(3-piperidin-1-yl-propoxy)-2,3-dihydro-1H-indole dihydrochloride

5-(3-piperidin-1-yl-propoxy)-2,3-dihydro-1H-indole dihydrochloride

4-Phenylbutyric acid
1821-12-1

4-Phenylbutyric acid

4-phenyl-1-[5-(3-piperidin-1-yl-propoxy)-2,3-dihydro-indol-1-yl]-butan-1-one
676255-48-4

4-phenyl-1-[5-(3-piperidin-1-yl-propoxy)-2,3-dihydro-indol-1-yl]-butan-1-one

Conditions
ConditionsYield
Stage #1: 5-(3-piperidin-1-yl-propoxy)-2,3-dihydro-1H-indole dihydrochloride; 4-Phenylbutyric acid With N-cyclohexylcarbodiimide-N'-methyl polystyrene HL; benzotriazol-1-ol; triethylamine In chloroform; acetonitrile; tert-butyl alcohol at 20℃;
Stage #2: With Silicycle triamine-3 In chloroform; acetonitrile; tert-butyl alcohol for 0.5 - 1h;
100%
morpholine
110-91-8

morpholine

4-Phenylbutyric acid
1821-12-1

4-Phenylbutyric acid

1-morpholino-4-phenylbutan-1-one
61123-44-2

1-morpholino-4-phenylbutan-1-one

Conditions
ConditionsYield
2-[(N,N-diisopropylamino)methyl]phenylboronic acid In toluene for 20h; Product distribution / selectivity; aza-Baeyer-Villiger Reaction; Heating / reflux;100%
With carbon disulfide; dmap; aluminum oxide In acetonitrile at 200℃; under 37503.8 Torr; for 0.45h; Flow reactor; Green chemistry;97%
methyl (L)-leucinate hydrochloride
7517-19-3

methyl (L)-leucinate hydrochloride

4-Phenylbutyric acid
1821-12-1

4-Phenylbutyric acid

(S)-methyl 4-methyl-2-(4-phenylbutanamido)pentanoate
1170728-22-9

(S)-methyl 4-methyl-2-(4-phenylbutanamido)pentanoate

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In tetrahydrofuran at 20℃; for 5h; Cooling with ice;100%
Acetanilid
103-84-4

Acetanilid

4-Phenylbutyric acid
1821-12-1

4-Phenylbutyric acid

N-acetyl-N-4-diphenylbutanamide

N-acetyl-N-4-diphenylbutanamide

Conditions
ConditionsYield
With 2,6-dimethylpyridine; dmap; di-tert-butyl dicarbonate In acetonitrile at 20 - 28℃; for 24h; Inert atmosphere;100%
C20-O-trityl-prostratin-ol
1262389-74-1

C20-O-trityl-prostratin-ol

4-Phenylbutyric acid
1821-12-1

4-Phenylbutyric acid

C49H52O6

C49H52O6

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 25℃; for 2h;99.41%
aniline
62-53-3

aniline

4-Phenylbutyric acid
1821-12-1

4-Phenylbutyric acid

N-phenyl-4-phenylbutanamide
3056-71-1

N-phenyl-4-phenylbutanamide

Conditions
ConditionsYield
With 3,4,5-trifluorophenylboronic acid In 1,3,5-trimethyl-benzene for 4h; Heating;99%
With carbon disulfide; dmap; aluminum oxide In acetonitrile at 200℃; under 37503.8 Torr; for 0.45h; Flow reactor; Green chemistry;96%
With boric acid In toluene for 15h; Dean-Stark; Reflux; Green chemistry; chemoselective reaction;92%
octanol
111-87-5

octanol

4-Phenylbutyric acid
1821-12-1

4-Phenylbutyric acid

n-octyl 4-phenylbutyrate
101873-65-8

n-octyl 4-phenylbutyrate

Conditions
ConditionsYield
With dimesitylammonium pentafluorobenzenesulfonate In n-heptane at 80℃; for 1h;99%
dimesitylammonium pentafluorobenzenesulfonate In n-heptane at 80℃; for 1h; Product distribution / selectivity;99%
iminodibenzyl pentafluorobenzenesulfonate In n-heptane at 115℃; for 1h; Product distribution / selectivity;98%
4-Phenylbutyric acid
1821-12-1

4-Phenylbutyric acid

4-phenyl-butan-1-ol
3360-41-6

4-phenyl-butan-1-ol

Conditions
ConditionsYield
Stage #1: 4-Phenylbutyric acid With sodium tetrahydroborate In tetrahydrofuran at 60℃; for 0.25h;
Stage #2: With iodine In tetrahydrofuran for 5h; Reagent/catalyst;
99%
Stage #1: 4-Phenylbutyric acid With sodium tetrahydroborate In tetrahydrofuran at 60℃; for 0.25h;
Stage #2: With iodine In tetrahydrofuran for 5h;
98.4%
With C25H42N6Rh(1+)*CF3O3S(1-); phenylsilane In tetrahydrofuran at 30℃; for 20h; Inert atmosphere;96%
dibutylamine
111-92-2

dibutylamine

4-Phenylbutyric acid
1821-12-1

4-Phenylbutyric acid

N,N-Dibutyl-4-phenyl-butyramide
61123-41-9

N,N-Dibutyl-4-phenyl-butyramide

Conditions
ConditionsYield
With 3,4,5-trifluorophenylboronic acid In 1,3,5-trimethyl-benzene for 14.5h; Heating; other solvent;99%
With bis(methylcyclopentadienyl) tin 1.) p-xylene, r.t.; 2.) p-xylene, 9 h, reflux; Yield given. Multistep reaction;
methanol
67-56-1

methanol

4-Phenylbutyric acid
1821-12-1

4-Phenylbutyric acid

methyl 3-(benzyl)propanoate
2046-17-5

methyl 3-(benzyl)propanoate

Conditions
ConditionsYield
tetrachlorobis(tetrahydrofuran)hafnium(IV) at 20℃; for 11h;99%
With molecular sevies 4A; tetrachlorobis(tetrahydrofuran)hafnium(IV) at 20℃; for 11h;99%
With sulfuric acid Reflux;97%
3,5-dimethylpiperidine
35794-11-7

3,5-dimethylpiperidine

4-Phenylbutyric acid
1821-12-1

4-Phenylbutyric acid

1-(3,5-Dimethyl-piperidin-1-yl)-4-phenyl-butan-1-one

1-(3,5-Dimethyl-piperidin-1-yl)-4-phenyl-butan-1-one

Conditions
ConditionsYield
With 3,4,5-trifluorophenylboronic acid In toluene for 16h; Heating; other reagents;99%
With 3,5-di-C10F21-C6H3-B(OH)2; 4 A molecular sieve In toluene for 15h; Heating;95%
With boric acid In toluene for 15h; Dean-Stark; Reflux; Green chemistry; chemoselective reaction;95%
With triethoxyantimony In toluene Acylation; Heating;44%
4-Phenylbutyric acid
1821-12-1

4-Phenylbutyric acid

benzylamine
100-46-9

benzylamine

N-benzyl-4-phenylbutanamide

N-benzyl-4-phenylbutanamide

Conditions
ConditionsYield
With 3,5-di-C10F21-C6H3-B(OH)2; 4 A molecular sieve In toluene for 4h; Heating;99%
With 4-(dihydroxyboranyl)-1-methylpyridin-1-ium iodide; 1-ethyl-3-methylimidazolium triflate In toluene for 5h; Heating;99%
With boric acid In n-heptane for 15h; Solvent; Dean-Stark; Reflux; Green chemistry; chemoselective reaction;99%
3-Hydroxypropionitrile
109-78-4

3-Hydroxypropionitrile

4-Phenylbutyric acid
1821-12-1

4-Phenylbutyric acid

2-cyanoethyl 4-phenylbutyrate

2-cyanoethyl 4-phenylbutyrate

Conditions
ConditionsYield
With Iron(III) isopropoxide; zirconium(IV) tetraisopropoxide In n-heptane for 23h;99%
tetrachlorobis(tetrahydrofuran)hafnium(IV) In toluene for 24h; Heating;94%
zirconium(IV) oxychloride In n-heptane for 5h; Heating;
1,1,1-tri(hydroxymethyl)propane
77-99-6

1,1,1-tri(hydroxymethyl)propane

4-Phenylbutyric acid
1821-12-1

4-Phenylbutyric acid

1,1,1-tri(4-phenylbutyroxymethyl)propane

1,1,1-tri(4-phenylbutyroxymethyl)propane

Conditions
ConditionsYield
tetrachlorobis(tetrahydrofuran)hafnium(IV) In toluene for 24h; Heating;99%
With molecualar sevies 4A; tetrachlorobis(tetrahydrofuran)hafnium(IV) In toluene at 120℃; for 24h;99%
decylthiol
143-10-2

decylthiol

4-Phenylbutyric acid
1821-12-1

4-Phenylbutyric acid

S-decyl 4-phenylbutanethioate

S-decyl 4-phenylbutanethioate

Conditions
ConditionsYield
tetrachlorobis(tetrahydrofuran)hafnium(IV) In toluene for 17h; Heating;99%
With molecular sevies 4A; tetrachlorobis(tetrahydrofuran)hafnium(IV) In toluene at 120℃; for 17h;99%

1821-12-1Relevant articles and documents

Schwenk,Papa,Ginsberg

, p. 576 (1943)

A Core–Shell-Structured Silver Nanowire/Nitrogen-Doped Carbon Catalyst for Enhanced and Multifunctional Electrofixation of CO2

Yang, Heng-Pan,Zhang, Han-Wen,Wu, Yu,Fan, Liang-Dong,Chai, Xiao-Yan,Zhang, Qian-Ling,Liu, Jian-Hong,He, Chuan-Xin

, p. 3905 - 3910 (2018)

Numerous catalysts have been successfully introduced for CO2 fixation in aqueous or organic systems. However, a single catalyst showing activity in both solvent types is still rare, to the best of our knowledge. We developed a core–shell-structured AgNW/NC700 composite using a Ag nanowire (NW) core encapsulated by a N-doped carbon (NC) shell at 700 °C. Through control experiments and density functional theory calculations, it was confirmed that Ag nanowires acted as the active sites for CO2 fixation and the uniformly coating of N-doped carbon created a CO2-rich environment around the Ag nanowires, which could significantly improve the catalytic activity of Ag nanowires for electrochemical CO2 fixation. Under mild conditions, up to 96 % faradaic efficiency of CO, 95 % yield of Ibuprofen and 92 % yield of propylene carbonate could be obtained in the electrochemical CO2 direct reduction, carboxylation and cycloaddition, respectively, using the same AgNWs/NC700 catalyst. These results might provide an alternative strategy for efficient electrochemical fixation of CO2.

-

Adametz et al.

, p. 1453 (1962)

-

The marked difference in conformational behavior of the two diastereomers of 7-substituted-1,1-dichloro-7b-((Z)-8-chloro-6,7-dihydro-5H-benzo[7]annulen-9- yl)-1a,2,3,7b-tetrahydro-1H-cyclopropa[a]naphthalene, single crystal X-ray, 1H NMR and AM1 studies

Roshan, Hamid,Rashidi-Ranjbar, Parviz

, p. 59 - 65 (2010)

The 7-substituted of 1 and 2 were synthesized and conformational analysis carried out. While 7-substituted of 2 show two conformers in solution, 7-substituted of 1 show only one form in solution. AM1 semi-empirical molecular orbital calculations show that the conformation of cycloheptadiene ring in 1 and 2 is a twist boat form. In this conformation, the C-7 substituents can be oriented in pseudo equatorial (exo) and pseudo axial (endo) positions. The 3J calculation with Haasnoot equation on optimized structure of 2 reproduces the observed 3J coupling constants in exo and endo forms. Ring inversion of cycloheptadiene moiety in substituted 2 interconvert the e′-a′ (exo-endo) positions. The 3J calculation on optimized structure of 1 shows that 7-substitution is in pseudo equatorial (exo) direction, as found in the crystal structure of 1a by single crystal X-ray crystallography. The barrier to ring inversion in 2a is determined by dynamic 1H NMR spectroscopy to be ΔG≠(335K) = 68.0 ± 0.5 kJ/mol.

Pd-Catalyzed Regioselective Branched Hydrocarboxylation of Terminal Olefins with Formic Acid

Chu, Jianxiao,Guo, Jianqiong,Ren, Wenlong,Shi, Yian,Shi, Yuan,Wang, Mingzhou,Zhou, Jintao

supporting information, p. 886 - 891 (2022/02/07)

A regioselective Pd-catalyzed hydrocarboxylation of terminal olefins with HCOOH is described. A wide variety of branched carboxylic acids can readily be obtained with high regioselectivities under mild reaction conditions. The reaction is operationally simple and requires no handling of toxic CO. The ligand and LiCl are important factors for reaction reactivity and selectivity.

Palladium-Catalyzed Direct C-H Arylation of 3-Butenoic Acid Derivatives

Yang, Shan,Liu, Lingling,Zhou, Zheng,Huang, Zhibin,Zhao, Yingsheng

supporting information, p. 296 - 299 (2021/01/13)

We report herein a direct method to synthesize 4-aryl-3-butenoic acid through a carboxylic-acid-directed oxidative Heck reaction. The various 4-aryl-3-butenoic acids are easily prepared in moderate to good yields. In view of the promising bioactivity of 4-phenyl-3-butenoic acid previously reported, its derivatives reported here may be bioactive.

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