15118-60-2

Basic information

• Product Name: 4-(4-Aminophenyl)butyric acid
• Synonyms: 4-(4-Aminophenyl)butanoicacid;p-Aminophenylbutyricacid;AKOS BB-8810;4-(4-AMINOPHENYL)BUTYRIC ACID;4-Aminophenylbutyric Acid;4-Aminobenzenebutanoic acid;4-Amino-benzenebutanoic;4-(4-azanylphenyl)butanoic acid
• CAS NO: 15118-60-2
• Molecular Formula: C₁₀H₁₃NO₂
• Molecular Weight: 179.22
• EINECS: 1806241-263-5
• Product Categories: Others;Peptide Synthesis;Unnatural Amino Acid Derivatives
• Mol File: 15118-60-2.mol
• Article Data: 13

Chemical Properties

• Melting Point: 121-124 °C(lit.)
• Boiling Point: 363.7 °C at 760 mmHg
• Flash Point: 173.7 °C
• Appearance: /
• Density: 1.177 g/cm³
• Vapor Pressure: 6.3E-06mmHg at 25°C
• Refractive Index: 1.583
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 4.70±0.10(Predicted)
• CAS DataBase Reference: 4-(4-Aminophenyl)butyric acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(4-Aminophenyl)butyric acid(15118-60-2)
• EPA Substance Registry System: 4-(4-Aminophenyl)butyric acid(15118-60-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 15118-60-2(Hazardous Substances Data)

Usage

Uses

4-(4-Aminophenyl)butyric Acid is a degradation product of Chlorambucil (C325050); an alkylating agent that is used as an chemotherapy drug in the treatment of chronic lymphocytic leukemia. Chlorambucil is also used to treat non-Hodgkin''s lymphoma (NHL) and Hodgkin''s disease.

InChI:InChI=1/C10H13NO2/c11-9-6-4-8(5-7-9)2-1-3-10(12)13/h4-7H,1-3,11H2,(H,12,13)

Synthetic route

3-(4-propionylaminobenzoyl)propionic acid → 4-(4-aminophenyl)butyric Acid (15118-60-2)

Conditions	Yield
With hydrazine hydrate; potassium hydroxide In diethylene glycol at 120℃; for 1.5h;	98%

4-(4-nitrophenyl)butanoic acid (5600-62-4) → 4-(4-aminophenyl)butyric Acid (15118-60-2)

Conditions	Yield
With hydrogen; 10percent Pd/C In methanol under 2068.65 Torr; for 1h;	96%
With sodium methanoate; hydrogen; palladium on activated charcoal In methanol	90%
With hydrogen; palladium on activated charcoal In methanol at 20℃; for 6h; Reduction;	85%

4-(4-acetamidophenyl)-4-oxobutanoic acid (5473-15-4) → 4-(4-aminophenyl)butyric Acid (15118-60-2)

Conditions	Yield
With hydrazine hydrate; potassium hydroxide In diethylene glycol for 1.5h; Reflux;	95%
With hydrazine hydrate; potassium hydroxide In diethylene glycol for 8h; Wolff-Kishner Reduction; Reflux;

4-(4-amino-phenyl)-butyric acid ethyl ester (15116-32-2) → 4-(4-aminophenyl)butyric Acid (15118-60-2)

Conditions	Yield
With potassium hydroxide In ethanol Heating;

4-Phenylbutyric acid (1821-12-1) + γ-phenyl-γ-butyrolactone → 4-(4-aminophenyl)butyric Acid (15118-60-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 22 percent / HNO3 / 6 h / Ambient temperature 2: 90 percent / H2, sodium methanoate / Pd/C / methanol View Scheme

4-Phenylbutyric acid (1821-12-1) → 4-(4-aminophenyl)butyric Acid (15118-60-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: nitric acid / -30 - -20 °C 2: Raney nickel; ethanol / Hydrogenation View Scheme
Multi-step reaction with 2 steps 1: nitric acid / -30 - -20 °C 2: zinc; aqueous hydrochloric acid View Scheme
Multi-step reaction with 2 steps 1: acetic acid anhydride; aqueous nitric acid / 20 - 40 °C 2: palladium/CaCO3; methanol / Hydrogenation View Scheme

2,2-diethoxy-5-(4-nitro-phenyl)-2,3-dihydro-furan (14308-34-0) → 4-(4-aminophenyl)butyric Acid (15118-60-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: H2 / Pd-C / dioxane 2: KOH / ethanol / Heating View Scheme

aniline (62-53-3) → 4-(4-aminophenyl)butyric Acid (15118-60-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: water / 0.33 h / 45 °C 2: aluminum (III) chloride / dichloromethane / 20 °C / Cooling with ice 3: potassium hydroxide; hydrazine hydrate / diethylene glycol / 1.5 h / Reflux View Scheme

Acetanilid (103-84-4) → 4-(4-aminophenyl)butyric Acid (15118-60-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: aluminum (III) chloride / dichloromethane / 20 °C / Cooling with ice 2: potassium hydroxide; hydrazine hydrate / diethylene glycol / 1.5 h / Reflux View Scheme
Multi-step reaction with 2 steps 1: aluminum (III) chloride / 8 h / 20 °C 2: potassium hydroxide; hydrazine hydrate / diethylene glycol / 8 h / Reflux View Scheme

4-(4-aminophenyl)butyric Acid (15118-60-2) → 4-(p-aminophenyl)butanol (91251-45-5)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 25℃; for 2h;	100%
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 25℃; for 2h;	96%
With lithium aluminium tetrahydride In tetrahydrofuran	95%

N-trifluoroacetoxy succinimide (5672-89-9) + 4-(4-aminophenyl)butyric Acid (15118-60-2) → C16H15F3N2O6

Conditions	Yield
In pyridine at 20℃;	99%

4-(4-aminophenyl)butyric Acid (15118-60-2) + (S)-2,5-dichloro-N-((tetrahydrofuran-2-yl)methyl)pyrimidin-4-amine → (S)-4-(4-(5-chloro-4-((tetrahydrofuran-2-yl)methylamino)pyrimidin-2-ylamino)phenyl)butanoic acid hydrochloride

Conditions	Yield
With hydrogenchloride In acetonitrile at 150℃; for 2h; Microwave irradiation;	99%

4-(4-aminophenyl)butyric Acid (15118-60-2) + N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → 4-[4'-(9H-fluoren-9-ylmethoxycarbonylamino)phenyl]butanoic acid (186320-14-9)

Conditions	Yield
Stage #1: 4-(4-aminophenyl)butyric Acid; N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide With sodium hydrogencarbonate In tetrahydrofuran at 20℃; Stage #2: With hydrogenchloride In tetrahydrofuran; water	98%
With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; for 16h; Inert atmosphere;	68%
With sodium carbonate In N,N-dimethyl-formamide

methanol (67-56-1) + 4-(4-aminophenyl)butyric Acid (15118-60-2) → methyl 4-(4-aminophenyl)butanoate (20637-09-6)

Conditions	Yield
With sulfuric acid for 1.5h; Reflux;	96%
With sulfuric acid at 20℃; for 12h; Inert atmosphere;	86%
With thionyl chloride In methanol at 0 - 80℃; for 16h;	70%
With sulfuric acid Reflux;	58%
With hydrogenchloride

methanol (67-56-1) + 4-(4-aminophenyl)butyric Acid (15118-60-2) → methyl 4-(p-aminophenyl)butyrate (205759-94-0)

Conditions	Yield
With thionyl chloride at 10 - 20℃; for 2h; Reflux;	96%

4-(4-aminophenyl)butyric Acid (15118-60-2) + 5,5-dichloro-meldrum’s acid → 4-(4-(2,2-dichloroacetamido)phenyl)butanoic acid

Conditions	Yield
In ethyl acetate at 20℃; for 16h; Sealed tube;	96%

di-tert-butyl dicarbonate (24424-99-5) + 4-(4-aminophenyl)butyric Acid (15118-60-2) → 4-(4-((tert-butoxycarbonyl)amino)phenyl)butanoic acid (105300-90-1)

Conditions	Yield
With triethylamine In 1,4-dioxane; water at 20℃; for 24h;	94%
Stage #1: di-tert-butyl dicarbonate; 4-(4-aminophenyl)butyric Acid With sodium hydroxide In tert-butyl alcohol at 0 - 20℃; for 9h; Stage #2: With potassium hydrogensulfate; water In diethyl ether pH=2 - 3;	94%

4-(4-aminophenyl)butyric Acid (15118-60-2) + acetic anhydride (108-24-7) → 4-(acetylamino)benzenebutanoic acid (31815-69-7)

Conditions	Yield
In water; acetonitrile for 4h; Ambient temperature;	93%

CH2Cl2/MeOH + 4-(4-aminophenyl)butyric Acid (15118-60-2) → methyl 4-(4-aminophenyl)butanoate (20637-09-6)

Conditions	Yield
With HCl conc.; sodium carbonate In methanol	91%

methanol (67-56-1) + 4-(4-aminophenyl)butyric Acid (15118-60-2) → 4-(4-aminophenyl)butanoic acid methyl ester hydrochloride

Conditions	Yield
With thionyl chloride at 0 - 20℃;	89.2%

3-heptadecylbenzene-1,2-diol (hydrolaccol) (5862-27-1) + 4-(4-aminophenyl)butyric Acid (15118-60-2) → 3-hepta-1,2-phenylene bis(4-aminophenyl)butanoate

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane	89%

4-(4-aminophenyl)butyric Acid (15118-60-2) + 4-Nitrophenyl isocyanate (100-28-7) → 4-(4-(3-(4-nitrophenyl)ureido)phenyl)butanoic acid (80258-90-8)

Conditions	Yield
With 1-methyl-pyrrolidin-2-one In benzene at 50℃; for 0.166667h;	88%
In N,N-dimethyl-formamide at 20℃; for 1h;	80%

phthalic anhydride (85-44-9) + 4-(4-aminophenyl)butyric Acid (15118-60-2) → 4-(4-(1,3-dioxoisoindolin-2-yl)phenyl)butanoic acid (209961-84-2)

Conditions	Yield
With triethylamine In toluene for 12h; Heating;	87%
In acetic acid for 5h; Inert atmosphere; Reflux;	81%

4-(4-aminophenyl)butyric Acid (15118-60-2) + phenol (108-95-2) → 4-(4-((4-hydroxyphenyl)diazenyl)phenyl)butanoic acid (887764-00-3)

Conditions	Yield
Stage #1: 4-(4-aminophenyl)butyric Acid With hydrogenchloride; ammonium sulphamate; sodium nitrite In water at 5℃; Stage #2: phenol With sodium hydroxide In water at 5℃; for 0.333333h; Stage #3: With hydrogenchloride In water pH=3;	86.7%
Stage #1: 4-(4-aminophenyl)butyric Acid With hydrogenchloride; sodium nitrite at 5℃; Stage #2: phenol With ammonium sulfamate; sodium hydroxide Stage #3: With hydrogenchloride In water pH=3;	61%

cyclobutanone (1191-95-3) + trimethylsilyl cyanide (7677-24-9) + 4-(4-aminophenyl)butyric Acid (15118-60-2) → 4-[4-(1-cyanocyclobutylamino)phenyl]butanoic acid (915086-92-9)

Conditions	Yield
With sodium sulfate In 1,4-dioxane for 15h; Product distribution / selectivity;	86%
With sodium sulfate In 1,4-dioxane for 15h;	86%
With sodium sulfate In 1,4-dioxane for 15h; Strecker reaction; Inert atmosphere;	86%
at 80℃; for 13h; Product distribution / selectivity;	74%

4-(4-aminophenyl)butyric Acid (15118-60-2) + 2,5-hexanedione (110-13-4) → 4-(4-(2,5-dimethyl-1H-pyrrol-1-yl)phenyl)butanoic acid

Conditions	Yield
Stage #1: 4-(4-aminophenyl)butyric Acid; 2,5-hexanedione With montmorillonite K10 Clay In dichloromethane at 20℃; for 0.25h; Stage #2: at 90℃; for 0.5h; Microwave irradiation;	85%

4-(4-aminophenyl)butyric Acid (15118-60-2) → 4-(4-nitrophenyl)butanoic acid (5600-62-4)

Conditions	Yield
With Oxone; sodium hydroxide In water; acetone at 8℃; buffer (NaHCO3);	84%

4-(4-aminophenyl)butyric Acid (15118-60-2) + (1R,2R,6S,7S)-4-oxa-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione (2746-19-2) → C19H19NO4 (1365657-66-4)

Conditions	Yield
With acetic acid In 1-methyl-pyrrolidin-2-one at 100℃; for 12h; Inert atmosphere;	83%

4-(4-aminophenyl)butyric Acid (15118-60-2) → methyl 4-(4-aminophenyl)butanoate (20637-09-6)

Conditions	Yield
With sulfuric acid; sodium carbonate In methanol	82%

4-(4-aminophenyl)butyric Acid (15118-60-2) + (R)-2,5-dichloro-N-((tetrahydrofuran-2-yl)methyl)pyrimidin-4-amine → (R)-4-(4-(5-chloro-4-((tetrahydrofuran-2-yl)methylamino)pyrimidin-2-ylamino)phenyl)butanoic acid hydrochloride

Conditions	Yield
With hydrogenchloride In acetonitrile at 150℃; for 2h; Microwave irradiation;	80%

4-(4-aminophenyl)butyric Acid (15118-60-2) + N,N-dimethyl-aniline (121-69-7) → C18H21N3O2

Conditions	Yield
Stage #1: 4-(4-aminophenyl)butyric Acid With nitrosonium tetrafluoroborate In dimethyl sulfoxide; acetonitrile for 0.25h; Cooling with ice; Stage #2: N,N-dimethyl-aniline In dimethyl sulfoxide; acetonitrile at 20℃; for 0.75h; Cooling with ice;	79%

3-Chloropivaloyl chloride (4300-97-4) + 4-(4-aminophenyl)butyric Acid (15118-60-2) → 4-butyric acid

Conditions	Yield
With pyridine In 1,4-dioxane for 1h; Heating;	78%

4-(4-aminophenyl)butyric Acid (15118-60-2) + 2,5-dichloro-N-((tetrahydrofuran-2-yl)methyl)pyrimidin-4-amine → 4-(4-(5-chloro-4-((tetrahydrofuran-2-yl)methylamino)pyrimidin-2-ylamino)phenyl)butanoic acid

Conditions	Yield
With hydrogenchloride In acetonitrile at 150℃; for 2h; Microwave irradiation;	78%
With hydrogenchloride In water; acetonitrile at 150℃; for 2h; Microwave irradiation;	78%

2-chloroethyl isothiocyanate (1943-83-5) + 4-(4-aminophenyl)butyric Acid (15118-60-2) → 4-phenyl>butyric acid (13908-55-9)

Conditions	Yield
In 1,2-dimethoxyethane for 24h;	77%
In ethanol Ambient temperature;

4-(4-aminophenyl)butyric Acid (15118-60-2) + 3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride (129-64-6) → C19H19NO4 (1365657-65-3)

Conditions	Yield
With acetic acid In 1-methyl-pyrrolidin-2-one at 100℃; for 12h; Inert atmosphere;	76%

cyclobutanone (1191-95-3) + 4-(4-aminophenyl)butyric Acid (15118-60-2) → 4-[4-(1-cyanocyclobutylamino)phenyl]butanoic acid (915086-92-9)

Conditions	Yield
With trimethylsilyl cyanide at 80℃; for 13h;	74%

Upstream product

• 5600-62-4 4-(4-nitrophenyl)butanoic acid 
• 15116-32-2 4-(4-amino-phenyl)-butyric acid ethyl ester 
• 1821-12-1 4-Phenylbutyric acid 
• 14308-34-0 2,2-diethoxy-5-(4-nitro-phenyl)-2,3-dihydro-furan 
• 62-53-3 aniline 
• 103-84-4 Acetanilid 
• 5473-15-4 4-(4-acetamidophenyl)-4-oxobutanoic acid 

Downstream Products

• 80258-90-8 4-(4-(3-(4-nitrophenyl)ureido)phenyl)butanoic acid 
• 177653-18-8 E 352 
• 694438-89-6 N-(2,6-diisopropylphenyl)-N'-[(4-butyric acid)phenyl]-1,6,7,12-tetrachloroperylene-3,4:9,10-tetracarboxylic acid bisimide 

Relevant articles and documents

P-aminobenzene butyric acid preparation method

The invention relates to a P-aminobenzene butyric acid preparation method. According to the method, alkyl-acyl aniline serves as raw materials, dichloroethane serves as a reaction solvent, a compound A is prepared by the aid of acylation reaction and acetone water recrystallization modes, P-aminobenzene butyric acid is prepared by the aid of Huang Minglong reaction according to the weight ratio of a solvent S and the compound A of 1:1, and the highest yield of end products reach 98%. The method cannot generate solid waste difficult to being treated and is environmentally friendly and stable in process and suitable for industrial production and high in yield, the purity of the prepared P-aminobenzene butyric acid is good, and the method assists in normal stable production of chlorambucil.

Design, synthesis and biological evaluation of novel sesquiterpene mustards as potential anticancer agents

Several novel series of sesquiterpene mustards (SMs) bearing nitrogen mustard and glutathione (GSH)-reactive α-methylene-γ-butyrolactone groups were successfully prepared for the first time and showed excellent antiproliferative activities in vitro. Among them, compounds 2e and 2g displayed the highest antiproliferative properties with IC50 values ranging from 2.5 to 8.7 μM. The selectivity of these two compounds was evaluated by SRB method against human cancer and normal hepatic cells (HepG2 and L02). The induction of apoptosis and effects on the cell cycle distribution with compounds 2e and 2g were investigated by Hoechst 33,258 staining and flow cytometry, which exhibited that they could induce selective cell apoptosis and cell cycle arrest in HepG2 and L02 cells. In addition, further investigation showed that compounds 2e and 2g could obviously inhibit the proliferation of HepG2 cells by inducing significant DNA cross-linking and depleting GSH in cell media. The good cytotoxicity and selectivity of compounds 2e and 2g pointed them as promising leads for anticancer drug design.