26311-45-5

Basic information

• Product Name: 4-Pentylbenzoic acid
• Synonyms: 4-pentyl-benzoicaci;Benzoic acid, 4-pentyl-;Benzoic acid, p-pentyl-;p-Amylbenzoic acid;p-amylbenzoicacid;para-Pentylbenzoic acid;p-n-Amylbenzoic acid;p-pentyl-benzoicaci
• CAS NO: 26311-45-5
• Molecular Formula: C₁₂H₁₆O₂
• Molecular Weight: 192.25
• EINECS: 247-607-9
• Product Categories: Liquid Crystal intermediates;Drug Intermediates;Benzoic Acids (Building Blocks for Liquid Crystals);Building Blocks for Liquid Crystals;Functional Materials;Building block;Liquid Crystals;Organic Electronics and Photonics;Liqiud crystal intermediates
• Mol File: 26311-45-5.mol
• Article Data: 8

Chemical Properties

• Melting Point: 85-90 °C
• Boiling Point: 261 °C (746 mmHg)
• Flash Point: 149.7 °C
• Appearance: white to light yellow crystalline powder
• Density: 1.0430
• Vapor Pressure: 0.000198mmHg at 25°C
• Refractive Index: 1.5207 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 4.35±0.10(Predicted)
• Water Solubility: insoluble
• BRN: 2044798
• CAS DataBase Reference: 4-Pentylbenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Pentylbenzoic acid(26311-45-5)
• EPA Substance Registry System: 4-Pentylbenzoic acid(26311-45-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: DH6273000
• TSCA: Yes
• Hazardous Substances Data: 26311-45-5(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystalline powder

Uses

Intermediates of Liquid Crystals

Safety Profile

Poison by intravenous route. When heated to decomposition it emits acrid smoke and irritating fumes.

InChI:InChI=1/C12H22O2/c1-2-3-4-5-10-6-8-11(9-7-10)12(13)14/h10-11H,2-9H2,1H3,(H,13,14)/p-1

Synthetic route

4-Bromobenzoic acid (586-76-5) + n-pentylmagnesium bromide (693-25-4) → 4-pentylbenzoic acid (26311-45-5)

Conditions	Yield
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In tetrahydrofuran -78 deg C, 10 min, 20 deg C, 3.5 h;	87%

1-Heptene (592-76-7) + 2H-pyran-2-one-5-carboxylic acid (500-05-0) → 4-pentylbenzoic acid (26311-45-5)

Conditions	Yield
With palladium 10% on activated carbon In 1,3,5-trimethyl-benzene at 200℃; Diels-Alder reaction; regioselective reaction;	85%

carbon dioxide (124-38-9) + (4-pentylphenyl)boronic acid (121219-12-3) → 4-pentylbenzoic acid (26311-45-5)

Conditions	Yield
With chloro[1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene]copper(I); potassium methanolate In tetrahydrofuran at 70℃; for 24h; Schlenk technique; Sealed tube;	71%

oxalyl dichloride (79-37-8) + pentylbenzene (538-68-1) → 4-pentylbenzoic acid (26311-45-5)

Conditions	Yield
With carbon disulfide; aluminium trichloride

4-pentylbenzaldehyde (6853-57-2) → 4-pentylbenzoic acid (26311-45-5)

Conditions	Yield
With jones reagent In acetone for 0.5h; Ambient temperature;

1-<4-pentyl-phenyl>-ethanone-(1) → 4-pentylbenzoic acid (26311-45-5)

Conditions	Yield
With sodium hypobromide

amyl iodide (628-17-1) + 4-iodobenzoic acid (619-58-9) → 4-pentylbenzoic acid (26311-45-5)

Conditions	Yield
Multistep reaction.;	10 mg

pentylbenzene (538-68-1) → 4-pentylbenzoic acid (26311-45-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: trifluoroacetic acid / 80 °C 2: Jones reagent / acetone / 0.5 h / Ambient temperature View Scheme

4-pentylbenzoic acid (26311-45-5) → 4-n-pentylbenzyl alcohol (81720-37-8)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 16h;	99%
With lithium aluminium tetrahydride In tetrahydrofuran	60%
With lithium aluminium tetrahydride

4-pentylbenzoic acid (26311-45-5) → 4-pentylphenylbenzylalcohol

Conditions	Yield
With sodium hydroxide In tetrahydrofuran; water	94%

4-pentylbenzoic acid (26311-45-5) + acetone (67-64-1) → 2-oxopropyl 4-pentylbenzoate

Conditions	Yield
With sodium chlorite; potassium iodide at 100℃; for 24h; Schlenk technique;	93%

methanol (67-56-1) + 4-pentylbenzoic acid (26311-45-5) → methyl 4-pentylbenzoate (26311-44-4)

Conditions	Yield
With acetyl chloride at 0 - 23℃; Inert atmosphere;	92%

4-pentylbenzoic acid (26311-45-5) → 4-trans-pentylcyclohexane-1-carboxylic acid (38289-29-1, 38792-89-1, 67589-84-8)

Conditions	Yield
Stage #1: 4-pentylbenzoic acid With sodium hydroxide; hydrogen In water at 140 - 150℃; under 22502.3 - 30003 Torr; for 1h; Stage #2: With sodium hydroxide In water at 260 - 280℃; under 22502.3 - 30003 Torr; for 2h; Further stages.;	88%
With hydrogen Multistep reaction;
In trans-4-butylcyclohexane carboxylic acid	80% (43 g)

8-amino quinoline (578-66-5) + 4-pentylbenzoic acid (26311-45-5) → 4-pentyl-N-(quinolin-8-yl)benzamide

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Inert atmosphere;	86%

4-pentylbenzoic acid (26311-45-5) + bis{1,9-(4-hydroxyphenyl)nonane} (115914-43-7) → nonane-1,9-diyl bis(4,1-phenylene) bis(4-pentylbenzoate)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane Steglich Esterification;	83%

5-[4-(4-heptylbenzoyl)-phenyl]-2-(4-hydroxyphenyl)-1,3,4-oxadiazole (881650-28-8) + 4-pentylbenzoic acid (26311-45-5) → 2-[4-(4-heptylbenzoyl)-phenyl]-5-[4-(5-pentylbenzoyl)-phenyl]-1,3,4-oxadiazole

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 20℃; for 48h;	80%

(3S,3αS,6R,8S,9βS)-6,8-dihydroxy-3,6,9-trimethyl-3α,4,5,6,6α,7,8,9β-octahydroazuleno[4,5-β]furan-2(3H)-one (1188382-13-9) + 4-pentylbenzoic acid (26311-45-5) → (3S,6R,8S)-6-hydroxy-3,6,9-trimethyl-2-oxo-2,3,3α,4,5,6,6α,7,8,9β-decahydroazuleno[4,5-β]furan-8-yl 4-pentylbenzoate

Conditions	Yield
Stage #1: (3S,3αS,6R,8S,9βS)-6,8-dihydroxy-3,6,9-trimethyl-3α,4,5,6,6α,7,8,9β-octahydroazuleno[4,5-β]furan-2(3H)-one; 4-pentylbenzoic acid With dmap In dichloromethane at 20℃; for 0.166667h; Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane	80%

5-[4-(4-dodecyloxybenzoyl)-phenyl]-2-(4-hydroxyphenyl)-1,3,4-oxadiazole (881649-30-5) + 4-pentylbenzoic acid (26311-45-5) → 2-[4-(4-dodecyloxybenzoyl)-phenyl]-5-[4-(4-pentylbenzoyl)-phenyl]-1,3,4-oxadiazole

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 20℃; for 48h;	79%

4-pentylbenzoic acid (26311-45-5) + thiosemicarbazide (79-19-6) → 5-(4-pentylphenyl)-1,3,4-thiadiazol-2-amine (114751-76-7)

Conditions	Yield
With trichlorophosphate at 0 - 70℃; for 4.5h;	78%
With trichlorophosphate at 0℃; for 4.5h; Reflux;

4-pentylbenzoic acid (26311-45-5) + 3-fluoro-4'-hydroxy-1,1'-biphenyl-4-carbonitrile (123843-58-3) → 4-cyano-3-fluorobiphenyl-4'-yl 4-pentylbenzoate

Conditions	Yield
With 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide In dichloromethane Ambient temperature;	77%

4-pentylbenzoic acid (26311-45-5) + (3αS,6R,8S,9βS)-8-hydroxy-6,9-dimethyl-3-methylene-2-oxo-2,3,3α,4,5,6,6α,7,8,9β-decahydroazuleno[4,5-b]furan-6-yl acetate → (3αS,6R,8S,9βS)-6-acetoxy-6,9-dimethyl-3-methylene-2-oxo-2,3,3α,4,5,6,6α,7,8,9β-decahydroazuleno[4,5-β]furan-8-yl 4-pentylbenzoate

Conditions	Yield
Stage #1: 4-pentylbenzoic acid; (3αS,6R,8S,9βS)-8-hydroxy-6,9-dimethyl-3-methylene-2-oxo-2,3,3α,4,5,6,6α,7,8,9β-decahydroazuleno[4,5-b]furan-6-yl acetate With dmap In dichloromethane at 20℃; for 0.166667h; Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	77%

4-pentylbenzoic acid (26311-45-5) + (4-(9-(4-hydroxyphenyl)nonyl)phenyl 4-cyanobenzoate) → 4-(9-(4-((4-cyanobenzoyl)oxy)phenyl)nonyl)phenyl 4-pentylbenzoate

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 2h; Inert atmosphere;	76%

4-pentylbenzoic acid (26311-45-5) + 4,5,6,7-tetrahydro-1H-imidazo<4,5-c>pyridine (6882-74-2) + oxalic acid (144-62-7) → 4-pentylphenyl-(1,4,6,7-tetrahydroimidazo[4,5-c]pyridin-5-yl)methanone oxalate

Conditions	Yield
Stage #1: 4-pentylbenzoic acid With 1,1'-carbonyldiimidazole In DMF (N,N-dimethyl-formamide) at 20℃; for 2h; Stage #2: 4,5,6,7-tetrahydro-1H-imidazo<4,5-c>pyridine With triethylamine In DMF (N,N-dimethyl-formamide) at 20℃; Stage #3: oxalic acid In ethyl acetate at 20℃;	73%

4-pentylbenzoic acid (26311-45-5) + (S)-4-(2-hydroxyethyl)-3-methylenedihydrofuran-2(3H)-one → C19H24O4

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 2h;	72.4%

2-methoxy-6-methyl-4(3H)-pyrimidinone (55996-28-6) + 4-pentylbenzoic acid (26311-45-5) → 4-Pentyl-benzoic acid 2-methoxy-6-methyl-pyrimidin-4-yl ester

Conditions	Yield
With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In tetrahydrofuran 1.) reflux, 2 h; 2.) RT, 18 h;	71%

4-pentylbenzoic acid (26311-45-5) + 4-[3-(4-hydroxyphenyl)-1,2,4-oxadiazol-5-yl]phenyl 4-hexyl-benzoate (1342883-62-8) → 4-{3-[4-(4-n-pentylbenzoyloxy)phenyl]-1,2,4-oxadiazol-5-yl}phenyl 4-hexylbenzoate (1342883-87-7)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 12h; Inert atmosphere;	71%
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 10h;

3-bromo-1,1,1-trifluoroacetone (431-35-6) + 4-pentylbenzoic acid (26311-45-5) → C15H15F3O2

Conditions	Yield
With dipotassium hydrogenphosphate; bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; silver(I) acetate In 2,2,2-trifluoroethanol at 140℃; for 24h;	71%

2-(2,4-difluorophenyl)-1-[4-(2-fluoro-4-amino-phenyl)-piperazin-1-yl]-3-(1H-1,2,4-triazol-1-yl)-propan-2-ol (950821-44-0) + 4-pentylbenzoic acid (26311-45-5) → C2H2N3CH2COHC6H3F2CH2N(CH2)4NC6H3FNHCOC6H4(CH2)4CH3

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	68.5%

4-pentylbenzoic acid (26311-45-5) + 4'-(4-menthyloxy-4-oxobutanoyloxy)-4-hydroxybiphenyl → C38H46O6

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In chloroform at 20℃; for 48h;	63%

4-pentylbenzoic acid (26311-45-5) + 4-cyano-3,5-difluoro-4'-hydroxybiphenyl (123843-59-4) → 4-cyano-3,5-difluorobiphenyl-4'-yl 4-pentylbenzoate

Conditions	Yield
With 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide In dichloromethane Ambient temperature;	61%

4-pentylbenzoic acid (26311-45-5) + (Z)-N′-hydroxy-1H-benzo[d]imidazole-5-carboximidamide → 3-(1H-benzo[d]imidazol-6-yl)-5-(4-pentylphenyl)-1,2,4-oxadiazole

Conditions	Yield
With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 110℃;	57.2%

4-pentylbenzoic acid (26311-45-5) + N-deacetylcolchicine trifluoroacetate (1415695-51-0) → 4-(n-pentyl)-N-{(7S)-1,2,3,10-tetramethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl}benzamide

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 3h; Inert atmosphere;	53%

(1S,3R,4R,5R,6R,7R,8R,9S)-(9-hydroxymethylhexaspiro[2.0.0.0.0.0.2.1.1.1.1.1]pentadec-1-yl)methanol (837430-97-4) + 4-pentylbenzoic acid (26311-45-5) → (1S,3R,4R,5R,6R,7R,8R,9S)-{9-[(4-n-pentylbenzoyl)oxymethyl]hexaspiro[2.0.0.0.0.0.2.1.1.1.1.1]pentadec-1-yl}methyl 4-n-pentylbenzoate

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 12h;	52%

4-pentylbenzoic acid (26311-45-5) + 4-hydroxybenzoic acid 4-cyanophenyl ester (70568-47-7) → 4-cyanophenyl 4'-[4''-(pentyl)benzoyloxy]benzoate

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h;	50%

Upstream product

• 79-37-8 oxalyl dichloride 
• 538-68-1 pentylbenzene 
• 6853-57-2 4-pentylbenzaldehyde 
• 586-76-5 4-Bromobenzoic acid 
• 693-25-4 n-pentylmagnesium bromide 
• 124-38-9 carbon dioxide 
• 121219-12-3 (4-pentylphenyl)boronic acid 
• 592-76-7 1-Heptene 
• 500-05-0 2H-pyran-2-one-5-carboxylic acid 
• 628-17-1 amyl iodide 
• 619-58-9 4-iodobenzoic acid 

Downstream Products

• 136101-39-8 4-Pentyl-benzoic acid 4-(2,2,2-trifluoro-acetyl)-phenyl ester 
• 84219-03-4 (trans-4-pentylcyclohexyl)acetic acid 
• 54887-92-2 4'-Cyanophenyl-4-n-butoxybenzoate 
• 49763-64-6 p-cyanophenyl p-pentylbenzoate 
• 135446-54-7 4-(4-pentylbenzoyloxy)-benzoic acid 
• 67589-90-6 trans-4-pentylcyclohexane-1-carboxylic acid chloride 
• 67679-85-0 trans-4-pentylcyclohexane carboxylic acid chloride 
• 488702-75-6 N-Methoxy-N-methyl-4-pentylbenzamide 
• 1296210-98-4 C₉H₉ClO₃*C₁₂H₁₆O₂ 
• 1291073-93-2 C₄₅H₄₁NO₈ 

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