4-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)butanoic acid supplier

Name
4-(1,3-DIOXO-1,3-DIHYDRO-2H-ISOINDOL-2-YL)BUTANOIC ACID
EINECS 200-589-5
CAS No. 3130-75-4
Article Data88
CAS DataBase
Density 1.389 g /cm³
Solubility
Melting Point 119-121 °C
Formula C₁₂H₁₁NO₄
Boiling Point 442.1 °C at 760 mmHg
Molecular Weight 233.224
Flash Point 221.2 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols Xi
Synonyms 2-Isoindolinebutyricacid, 1,3-dioxo- (6CI,7CI,8CI);4-(1,3-Dioxo-1,3-dihydroisoindol-2-yl)butyric Acid;4-Phthalimidobutanoic acid;4-Phthalimidobutyric acid;N-Phthalyl-g-aminobutyric acid;NSC 119133;g-Phthalimidobutyric acid;
PSA 74.68000
LogP 1.08530

Synthetic route

: 85-44-9
phthalic anhydride

: 56-12-2
4-amino-n-butyric acid

: 3130-75-4
4-phthalimidobutyric acid

Conditions

Conditions	Yield
at 170℃; for 6h;	100%
at 180℃;	94%
In neat (no solvent) at 170℃; for 3h; Inert atmosphere; Schlenk technique;	94%

: 1074-82-4
potassium phtalimide

: 56-12-2
4-amino-n-butyric acid

: 3130-75-4
4-phthalimidobutyric acid

Conditions

Conditions	Yield
at 180℃; for 0.5h;	96%

: 88-99-3
benzene-1,2-dicarboxylic acid

: 56-12-2
4-amino-n-butyric acid

: 3130-75-4
4-phthalimidobutyric acid

Conditions

Conditions	Yield
With propionic acid for 4h; Heating;	90%

: 136918-14-4
phthalimide

: 56-12-2
4-amino-n-butyric acid

: 3130-75-4
4-phthalimidobutyric acid

Conditions

Conditions	Yield
In toluene for 3h; Product distribution / selectivity; Heating / reflux;	81%
With acetic acid for 3h;

: 22509-74-6
N-ethoxycarbonylphthalimide

: 56-12-2
4-amino-n-butyric acid

: 3130-75-4
4-phthalimidobutyric acid

Conditions

Conditions	Yield
With sodium carbonate In water for 5h; Ambient temperature;	80%
With sodium carbonate for 1h;	48%
With sodium carbonate In water for 6h;	36%
With sodium carbonate In water at 20℃; for 3h;	21%

: 627-00-9
γ-chlorobutyric acid

: 1074-82-4
potassium phtalimide

: 3130-75-4
4-phthalimidobutyric acid

Conditions

Conditions	Yield
In water; N,N-dimethyl-formamide	80%
In water; N,N-dimethyl-formamide	80%

: 340-90-9
N-phthaloyl-L-glutamic acid

: 3130-75-4
4-phthalimidobutyric acid

Conditions

Conditions	Yield
In acetonitrile for 30h; Decarboxylation; Irradiation;	70%
In acetone at 20℃; for 12h; Irradiation;

: 292638-85-8
acrylic acid methyl ester

: 340-90-9
N-phthaloyl-L-glutamic acid

A: 3130-75-4
4-phthalimidobutyric acid

: 3-(2-carboxy-ethyl)-9b-hydroxy-5-oxo-2,3,5,9b-tetrahydro-1H-pyrrolo[2,1-a]isoindole-1-carboxylic acid methyl ester

: 3-(2-carboxy-ethyl)-9b-hydroxy-5-oxo-2,3,5,9b-tetrahydro-1H-pyrrolo[2,1-a]isoindole-1-carboxylic acid methyl ester

Conditions

Conditions	Yield
In acetonitrile for 30h; Cycloaddition; Irradiation;	A 5% B 20% C 41%

...Expand

: 96-48-0
4-butanolide

: 1074-82-4
potassium phtalimide

: 3130-75-4
4-phthalimidobutyric acid

Conditions

Conditions	Yield
at 200℃;
With N,N-dimethyl-formamide

: 39739-03-2
4-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-butyric acid methyl ester

: 3130-75-4
4-phthalimidobutyric acid

Conditions

Conditions	Yield
With sulfuric acid; water
With hydrogenchloride; water; acetic acid

: 16011-10-2
(Z)-4-phthalimidocrotonic acid

: 3130-75-4
4-phthalimidobutyric acid

Conditions

Conditions	Yield
With ethanol; platinum Hydrogenation;

: 16011-09-9
(E)-4-(1,3-dioxoisoindolin-2-yl)but-2-enoic acid

: 3130-75-4
4-phthalimidobutyric acid

Conditions

Conditions	Yield
With ethanol; platinum Hydrogenation;

: 4-phthalimidobutylguanidine sulfate

: 3130-75-4
4-phthalimidobutyric acid

Conditions

Conditions	Yield
With potassium permanganate; sulfuric acid for 1h; Ambient temperature;	13 mg

: 25830-77-7
N-phthaloyl-L-glutamic anhydride

A: 3130-75-4
4-phthalimidobutyric acid

B: 5203-11-2
(S)-2-(1,3-dioxoisoindolin-2-yl)butanoic acid

Conditions

Conditions	Yield
With hydrogenchloride; [2,2]bipyridinyl; bis(1,5-cyclooctadiene)nickel (0) 1.) THF, reflux, 2.5h.; Yield given. Multistep reaction. Yields of byproduct given;
With hydrogenchloride; bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine 1.) THF, reflux, 2.5h.; Yield given. Multistep reaction. Yields of byproduct given;

γ-phthalimido-butyric acid nitrile: γ-phthalimido-butyric acid nitrile

: 3130-75-4
4-phthalimidobutyric acid

Conditions

Conditions	Yield
With sulfuric acid beim Versetzen der abgekuehlten Loesung mit Wasser und Erhitzen des Reaktionsgemisches auf 120-130grad.;

γ-phthalimido-ethylmalonic acid: γ-phthalimido-ethylmalonic acid

: 3130-75-4
4-phthalimidobutyric acid

: 22509-74-6
N-ethoxycarbonylphthalimide

: 3130-75-4
4-phthalimidobutyric acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 225 mg / sodium bicarbonate / H2O / 1 h / Ambient temperature 2: 13 mg / potassium permanganate, sulfuric acid (1 N) / 1 h / Ambient temperature View Scheme

: 2913-97-5
N-phthalimidyl-2-aminoacetaldehyde

: 3130-75-4
4-phthalimidobutyric acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine / 100 °C 2: platinum; ethanol / Hydrogenation View Scheme
Multi-step reaction with 2 steps 1: pyridine / 100 °C 2: platinum; ethanol / Hydrogenation View Scheme

: 7504-49-6
2-(4-diazo-3-oxobutyl)isoindoline-1,3-dione

: 3130-75-4
4-phthalimidobutyric acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: silver oxide 2: hydrochloric acid; acetic acid; water View Scheme

: 85-44-9
phthalic anhydride

γ-pyrrolidone: γ-pyrrolidone

: 3130-75-4
4-phthalimidobutyric acid

Conditions

Conditions	Yield
In nitrogen; water	116.2 g (99.6%)

: 85-44-9
phthalic anhydride

: 660-88-8
5-aminopentanoic acid

: 3130-75-4
4-phthalimidobutyric acid

Conditions

Conditions	Yield
With triethylamine In toluene Reflux;

: 5428-09-1
3-phthalimido-1-propene

: benzene 1,3,5-triyl triformate

A: 3130-75-4
4-phthalimidobutyric acid

B: 35340-62-6
2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)butanoic acid

C: 24431-49-0
3-(1,3-dioxoisoindolin-2-yl)-2-methylpropanoic acid

Conditions

Conditions	Yield
With formic acid; bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In tetrahydrofuran at 100℃; Inert atmosphere; Sealed tube; Overall yield = 53 %; Overall yield = 61.2 mg;

...Expand

: 107-95-9
3-amino propanoic acid

: 56-12-2
4-amino-n-butyric acid

: 3130-75-4
4-phthalimidobutyric acid

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In water; acetonitrile at 20℃; for 0.5h;	0.92 g

: 3130-75-4
4-phthalimidobutyric acid

: 10314-06-4
4-phthalimidobutyryl chloride

Conditions

Conditions	Yield
With oxalyl dichloride In dichloromethane for 6h; Heating;	100%
With thionyl chloride	92%
With thionyl chloride In dichloromethane for 5h; Heating;	92%

: 79-37-8
oxalyl dichloride

: 3130-75-4
4-phthalimidobutyric acid

: N,N-bis(n-butylcarbamoyloxyethyl)-N-(4-phthalimidobutyryl) amine

Conditions

Conditions	Yield
With hydrogenchloride In N,N-bis(n-butylcarbamoyloxyethyl) amine; dichloromethane; triethylamine	97.1%
With hydrogenchloride In N,N-bis(n-butylcarbamoyloxyethyl) amine; dichloromethane; triethylamine

: 3130-75-4
4-phthalimidobutyric acid

: 17356-08-0
thiourea

: 92166-54-6
2-amino-4-(3-phthalimidopropyl)thiazole

Conditions

Conditions	Yield
Stage #1: 4-phthalimidobutyric acid; thiourea In N,N-dimethyl-formamide at 20℃; for 2h; Stage #2: With water; potassium carbonate	97%

: 3130-75-4
4-phthalimidobutyric acid

: 35197-64-9
2-bromo-4-(1,3-dioxoisoindolin-2-yl)butanoic acid

Conditions

Conditions	Yield
With phosphorus; bromine In tetrachloromethane Heating; 6-8 h;	96%
With phosphorus; bromine In tetrachloromethane 80 deg C, 30 min, reflux 8 h;	80%
Stage #1: 4-phthalimidobutyric acid With thionyl chloride for 2h; Heating / reflux; Stage #2: With bromine for 52h; Product distribution / selectivity; Heating / reflux;	58%

: 6723-30-4
O-2-tetrahydro-2H-pyranhydroxylamine

: 3130-75-4
4-phthalimidobutyric acid

: 1356930-35-2
4-(1,3-dioxoisoindolin-2-yl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In chloroform at 20℃;	94%

: 67-56-1
methanol

: 3130-75-4
4-phthalimidobutyric acid

: 39739-03-2
4-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-butyric acid methyl ester

Conditions

Conditions	Yield
With thionyl chloride at 0℃; for 4h;	93%

: 3130-75-4
4-phthalimidobutyric acid

: 4-phthalimidoperbutanoic acid

Conditions

Conditions	Yield
With sulfuric acid; dihydrogen peroxide	90%

: 3130-75-4
4-phthalimidobutyric acid

: 9b-hydroxy-1,2,3,9b-tetrahydro-5H-pyrrolo[2,1-a]isoindol-5-one

Conditions

Conditions	Yield
Stage #1: 4-phthalimidobutyric acid With potassium carbonate In water Sonication; Stage #2: In water; acetonitrile for 2.78h; Inert atmosphere; Flow reactor; UV-irradiation;	88%
With potassium carbonate In water; acetone at 15℃; Irradiation;	75%
With potassium carbonate In acetone Irradiation;	75%
Multi-step reaction with 2 steps 1: acetone; water / 0.25 h / Inert atmosphere 2: acetone; water / Irradiation; Inert atmosphere View Scheme

: 3130-75-4
4-phthalimidobutyric acid

: 97240-79-4
topiramate

: C24H30N2O11S

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	88%

: 100-60-7
N-methylcyclohexylamine

: 3130-75-4
4-phthalimidobutyric acid

: N-cyclohexyl-N-methyl-4-(1,3-dioxoisoindolin-2-yl)butanamide

Conditions

Conditions	Yield
Stage #1: 4-phthalimidobutyric acid With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.333333h; Inert atmosphere; Stage #2: N-methylcyclohexylamine In dichloromethane at 20℃; for 17h; Inert atmosphere;	87%

: 3130-75-4
4-phthalimidobutyric acid

: 3598-60-5
4-phthalimidobutanal

Conditions

Conditions	Yield
Stage #1: 4-phthalimidobutyric acid With 2,6-dimethylpyridine; nickel(II) bromide trihydrate; 4,4'-di-tert-butyl-2,2'-bipyridine; zinc; dimethyl dicarbonate In ethyl acetate for 0.25h; Inert atmosphere; Green chemistry; Stage #2: With diphenylsilane In ethyl acetate at 60℃; for 16h; Inert atmosphere; Green chemistry;	86%
Multi-step reaction with 2 steps 1: thionyl chloride / DMFA / 30 - 70 °C 2: 100 percent / H2 / Pd/BaSO4 / xylene / 6 h / Heating; catalyst poison View Scheme
Multi-step reaction with 2 steps 1: thionyl chloride 2: palladium/barium sulfate; xylene / 140 °C / Hydrogenation View Scheme
Multi-step reaction with 2 steps 1: oxalyl dichloride / dichloromethane / 8 h 2: palladium 10% on activated carbon; hydrogen; 2,6-dimethylpyridine / tetrahydrofuran / 6 h / 22 °C / 775.74 Torr View Scheme

: 927812-49-5
4-(1,3-diacetoxypropan-2-yloxy)indoline

: 3130-75-4
4-phthalimidobutyric acid

: 952595-60-7
1-(4-phthalimidobutanoyl)-4-(1,3-diacetoxypropan-2-yloxy)indoline

Conditions

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In acetonitrile at 20℃;	85%

: 3130-75-4
4-phthalimidobutyric acid

: 5-oxo-3,5-dihydro-2H-pyrrolo[2,1-a]isoindole-1-carboxylic acid

Conditions

Conditions	Yield
Stage #1: 4-phthalimidobutyric acid With t-butyldimethylsiyl triflate; triethylamine In chloroform for 3h; Stage #2: With potassium carbonate In methanol Further stages.;	85%

: 186581-53-3, 908094-01-9
diazomethane

: 3130-75-4
4-phthalimidobutyric acid

: 41306-64-3
2-(5-bromo-4-oxo-pentyl)-isoindole-1,3-dione

Conditions

Conditions	Yield
Stage #1: 4-phthalimidobutyric acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃; for 1h; Stage #2: diazomethane In diethyl ether; dichloromethane at 0℃; for 1.5h; Stage #3: With hydrogen bromide In diethyl ether; dichloromethane; water	84%
Stage #1: 4-phthalimidobutyric acid With sulfuryl dichloride Stage #2: diazomethane In diethyl ether Stage #3: With hydrogen bromide In tetrahydrofuran

: 5407-57-8
N-(7-chloroquinolin-4-yl)ethylenediamine

: 3130-75-4
4-phthalimidobutyric acid

: N-(2-((7-chloroquinolin-4-yl)amino)ethyl)-4-(1,3-dioxoisoindolin-2-yl)butanamide

Conditions

Conditions	Yield
Stage #1: 4-phthalimidobutyric acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 0.0833333h; Stage #2: N-(7-chloroquinolin-4-yl)ethylenediamine In N,N-dimethyl-formamide at 20℃; for 3h;	83%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;	83%

: 91-16-7
1,2-dimethoxybenzene

: 3130-75-4
4-phthalimidobutyric acid

: 76356-13-3
1-(3,4-dimethoxyphenyl)-4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)butan-1-one

Conditions

Conditions	Yield
With PPA at 80 - 90℃; for 1h;	82%

: 3130-75-4
4-phthalimidobutyric acid

: 106-89-8
epichlorohydrin

: 97663-53-1
N-(3-carboxypropyl)phthalimide glycidyl ester

Conditions

Conditions	Yield
benzyltrimethylammonium chloride for 0.25h; Heating;	81%

: 3130-75-4
4-phthalimidobutyric acid

: 59524-62-8
L-alanyl-D-isoglutamine benzyl ester hydrochloride

: benzyl N-(4-phthalimidobutanoyl)-L-alanyl-D-isoglutaminate

Conditions

Conditions	Yield
With diphenylphosphoranyl azide; triethylamine In N,N-dimethyl-formamide 1.) 0 deg C, 1 h, 2.) r.t., 24 h;	81%

: 13401-18-8
1,3-Dimethyllumazine

: 3130-75-4
4-phthalimidobutyric acid

: 121485-74-3
7-[3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-propyl]-1,3-dimethyl-1H-pteridine-2,4-dione

Conditions

Conditions	Yield
With ammonium peroxydisulfate; silver nitrate In water; acetonitrile for 5.5h; Heating;	80%

: 3130-75-4
4-phthalimidobutyric acid

: magnesium monomethyl malonate

: 213820-50-9
6-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-3-oxo-hexanoic acid methyl ester

Conditions

Conditions	Yield
With 1,1'-carbonyldiimidazole In tetrahydrofuran for 24h;	80%

: 10065-72-2
L-Alanine methyl ester

: 3130-75-4
4-phthalimidobutyric acid

: methyl 2-(4-(phthalimido-2-yl)butanamido)propanoate

Conditions

Conditions	Yield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In acetonitrile at 0 - 23℃; for 18h;	80%

: 3373-59-9
L-threonine methyl ester

: 3130-75-4
4-phthalimidobutyric acid

: methyl 2-(4-(phthalimido-2-yl)butanamido)-3-hydroxybutanoate

Conditions

Conditions	Yield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In acetonitrile at 0 - 23℃; for 18h;	80%

: 542-81-4
sulfure de methyle et de 2-chloroethyle

: 3130-75-4
4-phthalimidobutyric acid

: 4-phthalimidobutyric acid 2-(methylthio)ethyl ester

Conditions

Conditions	Yield
With triethylamine In ethyl acetate for 72h; Heating;	79%

: 3130-75-4
4-phthalimidobutyric acid

: 2-(3-fluoropentyl)isoindoline-1,3-dione

Conditions

Conditions	Yield
With disodium hydrogenphosphate; Ir[dF(CF3)ppy]2(dtbbpy)PF6; Selectfluor In water; acetonitrile for 12h; Inert atmosphere; Microwave irradiation;	79%

4-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)butanoic acid Specification

The IUPAC name of 4-Phthalimidobutyric acid is 4-(1,3-dioxoisoindol-2-yl)butanoic acid. With the CAS registry number 3130-75-4, it is also named as 1,3-Dihydro-1,3-dioxo-2H-isoindole-2-butanoic acid. The product's classification codes are Drug / Therapeutic Agent; Reproductive Effect. In addition, its molecular formula is C₁₂H₁₁NO₄ and molecular weight is 233.22.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 1.58; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.66; (4)ACD/LogD (pH 7.4): -1.14; (5)ACD/BCF (pH 5.5): 1.12; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 20.68; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 5; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 4; (12)Index of Refraction: 1.605; (13)Molar Refractivity: 57.79 cm³; (14)Molar Volume: 167.7 cm³; (15)Surface Tension: 62.3 dyne/cm; (16)Density: 1.389 g/cm³; (17)Flash Point: 221.2 °C; (18)Melting Point: 119-121 °C; (19)Enthalpy of Vaporization: 73.72 kJ/mol; (20)Boiling Point: 442.1 °C at 760 mmHg; (21)Vapour Pressure: 1.36E-08 mmHg at 25 °C.

Preparation of 4-Phthalimidobutyric acid: this chemical can be prepared by the reaction of Phthalic acid anhydride with 4-Amino-butyric acid.

This reaction will occur at temperature of 180 °C. The yield is 94 %.

Uses of 4-Phthalimidobutyric acid: it can be used to produce 4-Phthalimido-butyryl chloride.

This reaction needs SOCl₂. The yield is 92 %.

People can use the following data to convert to the molecule structure.
(1)SMILES: O=C2c1ccccc1C(=O)N2CCCC(=O)O
(2)InChI: InChI=1/C12H11NO4/c14-10(15)6-3-7-13-11(16)8-4-1-2-5-9(8)12(13)17/h1-2,4-5H,3,6-7H2,(H,14,15)
(3)InChIKey: HMKSXJBFBVGLJJ-UHFFFAOYAP
(4)Std. InChI: InChI=1S/C12H11NO4/c14-10(15)6-3-7-13-11(16)8-4-1-2-5-9(8)12(13)17/h1-2,4-5H,3,6-7H2,(H,14,15)
(5)Std. InChIKey: HMKSXJBFBVGLJJ-UHFFFAOYSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intraperitoneal	327mg/kg (327mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD	Indian Journal of Experimental Biology. Vol. 27, Pg. 805, 1989.

Product Name

4-(1,3-DIOXO-1,3-DIHYDRO-2H-ISOINDOL-2-YL)BUTANOIC ACID

Synthetic route

4-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)butanoic acid Specification

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