Product Name

  • Name

    3-Phenylglutaric acid

  • EINECS 224-016-4
  • CAS No. 4165-96-2
  • Article Data54
  • CAS DataBase
  • Density 1.2252 (rough estimate)
  • Solubility
  • Melting Point 140-143 ºC
  • Formula C11H12 O4
  • Boiling Point 379oC
  • Molecular Weight 208.214
  • Flash Point 185.3oC
  • Transport Information
  • Appearance Tan powder.
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 4165-96-2 (3-Phenylglutaric acid)
  • Hazard Symbols
  • Synonyms Glutaricacid, 3-phenyl- (6CI,7CI,8CI); 3-Phenylglutaric acid; 3-Phenylpentanedioicacid; b-Phenylglutaric acid
  • PSA 74.60000
  • LogP 1.71960

Synthetic route

2-phenyl-propane-1,1,3-tricarboxylic acid triethyl ester
5394-85-4

2-phenyl-propane-1,1,3-tricarboxylic acid triethyl ester

3-phenylglutaric acid
4165-96-2

3-phenylglutaric acid

Conditions
ConditionsYield
In potassium hydroxide for 24h; Heating;100%
3-methyl-5-[3-(3-methyl-4-nitro-5-isoxazolyl)-2-phenylpropyl]-4-nitroisoxazole
496806-21-4

3-methyl-5-[3-(3-methyl-4-nitro-5-isoxazolyl)-2-phenylpropyl]-4-nitroisoxazole

3-phenylglutaric acid
4165-96-2

3-phenylglutaric acid

Conditions
ConditionsYield
With potassium permanganate In water; acetone71%
3,5-dimethyl-4-nitroisoxazole
1123-49-5

3,5-dimethyl-4-nitroisoxazole

benzaldehyde
100-52-7

benzaldehyde

3-phenylglutaric acid
4165-96-2

3-phenylglutaric acid

Conditions
ConditionsYield
Stage #1: 3,5-dimethyl-4-nitroisoxazole; benzaldehyde With piperidine In tetrahydrofuran at 70 - 80℃; for 12h;
Stage #2: With potassium permanganate In tetrahydrofuran; water; acetone at 20℃; Further stages.;
60%
5-phenyl-cyclohexane-1,3-dione
493-72-1

5-phenyl-cyclohexane-1,3-dione

A

Bromoform
75-25-2

Bromoform

B

3-phenylglutaric acid
4165-96-2

3-phenylglutaric acid

Conditions
ConditionsYield
With sodium hypobromide
5-phenyl-cyclohexane-1,3-dione
493-72-1

5-phenyl-cyclohexane-1,3-dione

A

2-phenylsuccinic acid
635-51-8, 10424-29-0

2-phenylsuccinic acid

B

3-phenylglutaric acid
4165-96-2

3-phenylglutaric acid

Conditions
ConditionsYield
With permanganate(VII) ion
cinnamonitrile
4360-47-8

cinnamonitrile

sodium diethylmalonate
996-82-7

sodium diethylmalonate

3-phenylglutaric acid
4165-96-2

3-phenylglutaric acid

Conditions
ConditionsYield
durch Behandeln mit Salzsaeure;
sodium diethylmalonate
996-82-7, 34727-00-9, 73177-21-6

sodium diethylmalonate

3-phenylglutaric acid
4165-96-2

3-phenylglutaric acid

Conditions
ConditionsYield
Einw. von siedender Salzsaeure auf die entstehende Verbindung;
3-chloro-5-phenylcyclohex-2-en-1-one
51367-64-7

3-chloro-5-phenylcyclohex-2-en-1-one

A

2-phenylsuccinic acid
635-51-8, 10424-29-0

2-phenylsuccinic acid

B

3-phenylglutaric acid
4165-96-2

3-phenylglutaric acid

Conditions
ConditionsYield
With permanganate(VII) ion
3-phenylglutaronitrile
78533-73-0

3-phenylglutaronitrile

3-phenylglutaric acid
4165-96-2

3-phenylglutaric acid

Conditions
ConditionsYield
With potassium hydroxide
2,4-diethoxycarbonyl-5-hydroxy-5-methyl-3-phenylcyclohexanone
17572-39-3

2,4-diethoxycarbonyl-5-hydroxy-5-methyl-3-phenylcyclohexanone

3-phenylglutaric acid
4165-96-2

3-phenylglutaric acid

Conditions
ConditionsYield
With potassium hydroxide
2-phenyl-1,1,3,3-tetraethoxycarbonylpropane
6768-26-9

2-phenyl-1,1,3,3-tetraethoxycarbonylpropane

3-phenylglutaric acid
4165-96-2

3-phenylglutaric acid

Conditions
ConditionsYield
With hydrogen bromide
With hydrogenchloride
With hydrogen bromide
diethyl 2-cyano-3-phenylpentanedioate
6456-84-4

diethyl 2-cyano-3-phenylpentanedioate

3-phenylglutaric acid
4165-96-2

3-phenylglutaric acid

Conditions
ConditionsYield
With sulfuric acid
3-phenylpent-2-enedioic acid
87894-68-6

3-phenylpent-2-enedioic acid

3-phenylglutaric acid
4165-96-2

3-phenylglutaric acid

Conditions
ConditionsYield
With hydrogen iodide at 150℃; im geschlossenen Rohr;
sodium diethylmalonate
996-82-7, 34727-00-9, 73177-21-6

sodium diethylmalonate

ethyl benzylidenecyanoacetate
2025-40-3

ethyl benzylidenecyanoacetate

3-phenylglutaric acid
4165-96-2

3-phenylglutaric acid

Conditions
ConditionsYield
With ethanol Erhitzen des Reaktionsprodukts mit wss. Bromwasserstoffsaeure;
[(Z)-3-Ethoxy-1-((E)-2-ethoxy-2-ethylsulfanyl-vinyl)-3-ethylsulfanyl-allyl]-benzene
32386-46-2

[(Z)-3-Ethoxy-1-((E)-2-ethoxy-2-ethylsulfanyl-vinyl)-3-ethylsulfanyl-allyl]-benzene

3-phenylglutaric acid
4165-96-2

3-phenylglutaric acid

Conditions
ConditionsYield
(acid hydrolysis);
3-phenylpentanedioic acid monoethyl ester
106842-97-1

3-phenylpentanedioic acid monoethyl ester

3-phenylglutaric acid
4165-96-2

3-phenylglutaric acid

Conditions
ConditionsYield
With sodium hydroxide
methyl-malonic acid dimethylester
609-02-9

methyl-malonic acid dimethylester

Methyl cinnamate
103-26-4

Methyl cinnamate

3-phenylglutaric acid
4165-96-2

3-phenylglutaric acid

Conditions
ConditionsYield
Multistep reaction;
diethyl 2,4‑diacetyl‑3‑phenylpentanedioate
13277-74-2

diethyl 2,4‑diacetyl‑3‑phenylpentanedioate

3-phenylglutaric acid
4165-96-2

3-phenylglutaric acid

Conditions
ConditionsYield
With potassium hydroxide In ethanol Heating;
Stage #1: diethyl 2,4‑diacetyl‑3‑phenylpentanedioate With sodium hydroxide In ethanol for 2h; Reflux;
Stage #2: With hydrogenchloride In ethanol; water Cooling with ice;
With potassium hydroxide In water at 80℃; for 2h;4.89 g
With water; sodium hydroxide In ethanol at 20℃; for 21h; Reflux;
3-phenylglutaric acid anhydride
4160-80-9

3-phenylglutaric acid anhydride

sulfuric acid
7664-93-9

sulfuric acid

3-phenylglutaric acid
4165-96-2

3-phenylglutaric acid

Conditions
ConditionsYield
at 20℃;
hydrogenchloride
7647-01-0

hydrogenchloride

5-oxo-3-phenyl-5-piperidino-valeric acid
102076-28-8

5-oxo-3-phenyl-5-piperidino-valeric acid

3-phenylglutaric acid
4165-96-2

3-phenylglutaric acid

hydrogenchloride
7647-01-0

hydrogenchloride

2,6-dioxo-4-phenyl-piperidine-3-carboxylic acid ethyl ester
105812-70-2

2,6-dioxo-4-phenyl-piperidine-3-carboxylic acid ethyl ester

3-phenylglutaric acid
4165-96-2

3-phenylglutaric acid

dihydrogen peroxide
7722-84-1

dihydrogen peroxide

2-acetyl-5-phenylcyclohexane-1,3-dione
2057-01-4

2-acetyl-5-phenylcyclohexane-1,3-dione

3-phenylglutaric acid
4165-96-2

3-phenylglutaric acid

2-acetyl-5-phenylcyclohexane-1,3-dione
2057-01-4

2-acetyl-5-phenylcyclohexane-1,3-dione

hypobromite

hypobromite

3-phenylglutaric acid
4165-96-2

3-phenylglutaric acid

hydrogenchloride
7647-01-0

hydrogenchloride

2,6-dioxo-1,4-diphenyl-piperidine-3-carboxylic acid ethyl ester

2,6-dioxo-1,4-diphenyl-piperidine-3-carboxylic acid ethyl ester

A

3-phenylglutaric acid
4165-96-2

3-phenylglutaric acid

B

aniline
62-53-3

aniline

5-phenyl-cyclohexane-1,3-dione
493-72-1

5-phenyl-cyclohexane-1,3-dione

aqueous permanganate

aqueous permanganate

A

2-phenylsuccinic acid
635-51-8, 10424-29-0

2-phenylsuccinic acid

B

3-phenylglutaric acid
4165-96-2

3-phenylglutaric acid

β-phenyl-propane-α.α.γ-tricarboxylic acid triethyl ester

β-phenyl-propane-α.α.γ-tricarboxylic acid triethyl ester

3-phenylglutaric acid
4165-96-2

3-phenylglutaric acid

Conditions
ConditionsYield
With alkaline solution erhitzt das durch verd. Salzsaeure ausgeschiedene Oel auf 110-120grad;
With barium dihydroxide erhitzt das durch verd. Salzsaeure ausgeschiedene Oel auf 110-120grad;
2-cyano-3-phenyl-glutaric acid imide

2-cyano-3-phenyl-glutaric acid imide

3-phenylglutaric acid
4165-96-2

3-phenylglutaric acid

Conditions
ConditionsYield
With sulfuric acid
2-phenyl-propane-tetracarboxylic acid-(1.1.3.3)-tetramethyl ester

2-phenyl-propane-tetracarboxylic acid-(1.1.3.3)-tetramethyl ester

3-phenylglutaric acid
4165-96-2

3-phenylglutaric acid

Conditions
ConditionsYield
With alkaline solution Erhitzen des Reaktionsprodukts auf 130grad;
2-phenyl-propane-tricarboxylic acid-(1.1.3)-methyl ester-(1)

2-phenyl-propane-tricarboxylic acid-(1.1.3)-methyl ester-(1)

3-phenylglutaric acid
4165-96-2

3-phenylglutaric acid

Conditions
ConditionsYield
With potassium hydroxide at 100℃; Erhitzen des Reaktionsprodukts auf 170-185grad;
ethanol
64-17-5

ethanol

3-phenylglutaric acid
4165-96-2

3-phenylglutaric acid

diethyl 3-phenylpentanedioate
55951-74-1

diethyl 3-phenylpentanedioate

Conditions
ConditionsYield
With sulfuric acid at 80℃; for 3h;98%
Stage #1: 3-phenylglutaric acid With thionyl chloride at 80℃; for 1h;
Stage #2: ethanol at 80℃; for 0.5h;
91.5%
With sulfuric acid at 80℃; for 3h;74%
3-phenylglutaric acid
4165-96-2

3-phenylglutaric acid

3-phenylglutaric acid anhydride
4160-80-9

3-phenylglutaric acid anhydride

Conditions
ConditionsYield
In acetic anhydride for 2h; Heating;98%
With thionyl chloride for 15h; Heating;95%
With dicyclohexyl-carbodiimide In dichloromethane at 0℃;95%
3-phenylglutaric acid
4165-96-2

3-phenylglutaric acid

4-phenyltetrahydro-2H-pyran
20638-52-2

4-phenyltetrahydro-2H-pyran

Conditions
ConditionsYield
With indium(III) bromide; 1,1,3,3-Tetramethyldisiloxane In toluene at 60℃; for 15h; Inert atmosphere;98%
3-phenylglutaric acid
4165-96-2

3-phenylglutaric acid

4-phenylpiperidine-2,6-dione
14149-31-6

4-phenylpiperidine-2,6-dione

Conditions
ConditionsYield
With urea at 150℃; for 2h;97%
With ammonia in Schmelze;
3-phenylglutaric acid
4165-96-2

3-phenylglutaric acid

3-(4-Nitro-phenyl)-pentanedioic acid
92289-14-0

3-(4-Nitro-phenyl)-pentanedioic acid

Conditions
ConditionsYield
Stage #1: 3-phenylglutaric acid With sulfuric acid at 0℃; for 0.333333h;
Stage #2: With nitric acid at 20℃; for 3.33333h; Conversion of starting material;
94%
3-phenylglutaric acid
4165-96-2

3-phenylglutaric acid

3-phenylpentane-1,5-diol
829-27-6

3-phenylpentane-1,5-diol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 16h; Reflux; Inert atmosphere;93%
With dimethylsulfide borane complex In tetrahydrofuran at 0 - 25℃; for 16h; Inert atmosphere;92%
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 16h; Reflux;90%
3-phenylglutaric acid
4165-96-2

3-phenylglutaric acid

2-(3-oxo-2,3-dihydro-1H-inden-1-yl)acetic acid
25173-12-0

2-(3-oxo-2,3-dihydro-1H-inden-1-yl)acetic acid

Conditions
ConditionsYield
Stage #1: 3-phenylglutaric acid With thionyl chloride for 0.5h; Heating / reflux;
Stage #2: With aluminum (III) chloride In nitrobenzene at 80℃; for 1.5h; Friedel Crafts Acylation;
90%
With PPA at 125℃; for 0.166667h;73%
With sulfuric acid at 100℃;
tempol
3637-10-3

tempol

3-phenylglutaric acid
4165-96-2

3-phenylglutaric acid

C29H46N2O6

C29H46N2O6

Conditions
ConditionsYield
Stage #1: tempol; 3-phenylglutaric acid With dmap In dichloromethane for 0.5h; Inert atmosphere;
Stage #2: With dicyclohexyl-carbodiimide In dichloromethane at -5 - 20℃; for 8h; Inert atmosphere;
86.3%
4-hydroxy-2,2,6,6-tetramethylpiperidine
2403-88-5

4-hydroxy-2,2,6,6-tetramethylpiperidine

3-phenylglutaric acid
4165-96-2

3-phenylglutaric acid

C29H46N2O4

C29H46N2O4

Conditions
ConditionsYield
Stage #1: 4-hydroxy-2,2,6,6-tetramethylpiperidine; 3-phenylglutaric acid With dmap In dichloromethane for 0.5h; Inert atmosphere;
Stage #2: With dicyclohexyl-carbodiimide In dichloromethane at -5 - 20℃; for 8h; Inert atmosphere;
86.2%
3-phenylglutaric acid
4165-96-2

3-phenylglutaric acid

urea
57-13-6

urea

4-phenylpiperidine-2,6-dione
14149-31-6

4-phenylpiperidine-2,6-dione

Conditions
ConditionsYield
at 160℃; for 3h;79%
at 160℃; for 1h;72%
2,3,4,5,6-pentafluorophenol
771-61-9

2,3,4,5,6-pentafluorophenol

3-phenylglutaric acid
4165-96-2

3-phenylglutaric acid

1,5-bis(pentafluorophenyl)-3-phenylpentanedioate

1,5-bis(pentafluorophenyl)-3-phenylpentanedioate

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In ethyl acetate at 0℃; for 5h;75%
3-phenylglutaric acid
4165-96-2

3-phenylglutaric acid

4-amino-2-chlorobenzonitrile
20925-27-3

4-amino-2-chlorobenzonitrile

5-((3-chloro-4-cyanophenyl)amino)-5-oxo-3-phenylpentanoic acid
1427185-38-3

5-((3-chloro-4-cyanophenyl)amino)-5-oxo-3-phenylpentanoic acid

Conditions
ConditionsYield
Stage #1: 3-phenylglutaric acid With acetic anhydride at 100℃; for 14h;
Stage #2: 4-amino-2-chlorobenzonitrile With triethylamine In toluene at 80℃; for 3h;
72.9%
3-phenylglutaric acid
4165-96-2

3-phenylglutaric acid

(2-fluoro-1-fluoromethyl-ethyl)-benzene
87453-29-0

(2-fluoro-1-fluoromethyl-ethyl)-benzene

Conditions
ConditionsYield
With xenon difluoride; hydrogen fluoride In dichloromethane at 22℃; for 12h;60%
With xenon difluoride; hydrogen fluoride In dichloromethane at 22℃;60%
With xenon difluoride In dichloromethane for 8h;60%
3-phenylglutaric acid
4165-96-2

3-phenylglutaric acid

Conditions
ConditionsYield
Stage #1: 3-phenylglutaric acid With trifluoroacetic anhydride In dichloromethane at 0℃; for 2h;
Stage #2: With sodium tetrahydroborate In tetrahydrofuran for 24h;
Stage #3: With trifluoroacetic acid In dichloromethane for 16h;
60%
Multi-step reaction with 4 steps
1: AcCl / 3 h
2: 91 percent / pyridine / 2 h / Heating
3: potassium tert-butoxide; LiBH4 / tetrahydrofuran / 1 h / Heating
4: p-TsOH / toluene
View Scheme
Multi-step reaction with 2 steps
1: 98 percent / acetic anhydride / 2 h / Heating
2: 19 percent / NaBH4 / tetrahydrofuran / 1 h / 0 deg C to rt
View Scheme
Multi-step reaction with 2 steps
1: 95 percent / dicyclohexylcarbodiimide / CH2Cl2 / 0 °C
2: 86 percent / NaBH4 / tetrahydrofuran / a) 0 deg C, 1 h, b) RT, 0.5 h
View Scheme
Multi-step reaction with 2 steps
1: lithium aluminium tetrahydride / tetrahydrofuran / 24 h / Inert atmosphere; Reflux
2: 1-hydroxytetraphenylcyclopentadienyl(tetraphenyl-2,4-cyclopentadien-1-one)-μ-hydrotetracarbonyldiruthenium(II); {bis(salicylidene-γ-iminopropyl)methylamine}cobalt(II); 2,6-dimethoxy-p-quinone / chlorobenzene / 24 h / 80 °C
View Scheme
3-phenylglutaric acid
4165-96-2

3-phenylglutaric acid

methyl iodide
74-88-4

methyl iodide

3-phenyl-pentanedioic acid monomethyl ester
132015-40-8

3-phenyl-pentanedioic acid monomethyl ester

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 0 - 25℃; for 16h;55%
Stage #1: 3-phenylglutaric acid; methyl iodide With caesium carbonate In N,N-dimethyl-formamide at 0 - 25℃; for 16h;
Stage #2: With sodium hydrogencarbonate In water; N,N-dimethyl-formamide pH=~ 9;
3-phenylglutaric acid
4165-96-2

3-phenylglutaric acid

water
7732-18-5

water

(1,3,5-triaza-7-phosphaadamantane)
53597-69-6

(1,3,5-triaza-7-phosphaadamantane)

silver(l) oxide
20667-12-3

silver(l) oxide

2Ag(1+)*C11H10O4(2-)*8H2O*2C6H12N3P

2Ag(1+)*C11H10O4(2-)*8H2O*2C6H12N3P

Conditions
ConditionsYield
In methanol at 20℃; for 2h;50%
methanol
67-56-1

methanol

3-phenylglutaric acid
4165-96-2

3-phenylglutaric acid

dimethyl 3-phenylpentanedioate
19006-47-4

dimethyl 3-phenylpentanedioate

Conditions
ConditionsYield
With sulfuric acid
sulfuric acid In toluene for 24h; Ambient temperature;
With sulfuric acid
Ketene
463-51-4

Ketene

diethyl ether
60-29-7

diethyl ether

3-phenylglutaric acid
4165-96-2

3-phenylglutaric acid

3-phenylglutaric acid anhydride
4160-80-9

3-phenylglutaric acid anhydride

Ketene
463-51-4

Ketene

3-phenylglutaric acid
4165-96-2

3-phenylglutaric acid

3-phenylglutaric acid anhydride
4160-80-9

3-phenylglutaric acid anhydride

Conditions
ConditionsYield
With diethyl ether
3-phenylglutaric acid
4165-96-2

3-phenylglutaric acid

3-(4-bromophenyl)pentanedioic acid
1141-24-8

3-(4-bromophenyl)pentanedioic acid

Conditions
ConditionsYield
With bromine
3-phenylglutaric acid
4165-96-2

3-phenylglutaric acid

3-phenyl-glutaroyl chloride
216586-10-6

3-phenyl-glutaroyl chloride

Conditions
ConditionsYield
With phosphorus pentachloride
With thionyl chloride for 1h; Heating;
3-phenylglutaric acid
4165-96-2

3-phenylglutaric acid

diethyl 3-phenylpentanedioate
55951-74-1

diethyl 3-phenylpentanedioate

Conditions
ConditionsYield
With tetrachloromethane; ethanol
3-phenylglutaric acid
4165-96-2

3-phenylglutaric acid

2-bromo-3-phenyl-glutaric acid dimethyl ester
861372-79-4

2-bromo-3-phenyl-glutaric acid dimethyl ester

Conditions
ConditionsYield
With phosphorus pentachloride; bromine Eingiessen des Reaktionsprodukts in Methanol;

3-Phenylglutaric acid Chemical Properties

Molecular Structure of 3-Phenylglutaric acid (CAS NO.4165-96-2):

Molecular Formula: C11H12O4
Molecular Weight: 208.2106
IUPAC Name: 3-Phenylpentanedioic acid
Synonyms of 3-Phenylglutaric acid (CAS NO.4165-96-2): 3-Phenylglutaric acid, 98+% ; 3-Phenylglutaricacid,97% ; Benzylsuccinic ; Pentanedioic acid, 3-phenyl-
CAS NO: 4165-96-2
Classification Code: Carboxylic Acid Monomers ; Monomers ; Polymer Science
Melting point: 140-143 °C 
Index of Refraction: 1.566
Molar Refractivity: 52.83 cm3
Molar Volume: 161.7 cm3
Surface Tension: 57.5 dyne/cm
Density: 1.287 g/cm3
Flash Point: 185.3 °C
Enthalpy of Vaporization: 63.84 kJ/mol
Boiling Point: 359.4 °C at 760 mmHg
Vapour Pressure: 8.61E-06 mmHg at 25°C

3-Phenylglutaric acid Safety Profile

WGK Germany of 3-Phenylglutaric acid (CAS NO.4165-96-2): 3

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