Acetamide,N-(1,3-dihydro-1,3-dioxo-4-isobenzofuranyl)- supplier

Name
Acetamide,N-(1,3-dihydro-1,3-dioxo-4-isobenzofuranyl)-
EINECS 808-040-8
CAS No. 6296-53-3
Density 1.512 g/cm³
Solubility
Melting Point 185-186℃
Formula C₁₀H₇NO₄
Boiling Point 489.1 °C at 760 mmHg
Molecular Weight 205.17
Flash Point 249.6 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Phthalicanhydride, 3-acetamido- (6CI,8CI);3-Acetamidophthalic anhydride;3-Acetylaminophthalic anhydride;NSC 16261;NSC 17048;AC1L5EJ7;AC1Q6H8C;n-(1,3-Dioxo-1,3-dihydro-2-benzofuran-4-yl)acetamide;AKOS002687661;N-(1,3-dioxo-2-benzofuran-4-yl)acetamide;
PSA 72.47000
LogP 1.02860

Synthetic route

: 3-aminophthalic acid

: 108-24-7
acetic anhydride

: 6296-53-3
3-acetylaminophthalic anhydride

Conditions

Conditions	Yield
In Isopropyl acetate at 75 - 95℃; Temperature; Large scale;	88.6%

: 603-11-2
3-nitrophthalic acid

: 108-24-7
acetic anhydride

: 6296-53-3
3-acetylaminophthalic anhydride

Conditions

Conditions	Yield
With palladium 10% on activated carbon; hydrogen at 80 - 115℃; under 7500.75 Torr; Temperature; Autoclave;	83%

: 5434-20-8
3-aminophthalic acid

: 108-24-7
acetic anhydride

: 6296-53-3
3-acetylaminophthalic anhydride

Conditions

Conditions	Yield
for 4h; Concentration; Temperature; Reflux;	78.5%
at 0 - 5℃; for 4h; Heating / reflux;	61%
for 3h; Reflux;	61%

: 641-70-3
3-nitrophthalic acid anhydride

: 6296-53-3
3-acetylaminophthalic anhydride

Conditions

Conditions	Yield
With acetic anhydride; palladium Hydrogenation;

3-amino-phthalic acid-hydrochloride: 3-amino-phthalic acid-hydrochloride

: 6296-53-3
3-acetylaminophthalic anhydride

Conditions

Conditions	Yield
With acetic anhydride

: 108-24-7
acetic anhydride

<3-amino-phthalic acid >-anhydride: <3-amino-phthalic acid >-anhydride

: 6296-53-3
3-acetylaminophthalic anhydride

: 108-24-7
acetic anhydride

zinc-acetat-<3-amino phthalate>: zinc-acetat-<3-amino phthalate>

: 6296-53-3
3-acetylaminophthalic anhydride

: 603-11-2
3-nitrophthalic acid

: 6296-53-3
3-acetylaminophthalic anhydride

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: tin dichloride; hydrochloric acid View Scheme
Multi-step reaction with 2 steps 1: hydrogen / palladium-carbon / ethanol 2: acetic anhydride View Scheme
Multi-step reaction with 2 steps 1: palladium 10% on activated carbon; hydrogen / ethanol / 13 h / 2585.81 - 2844.39 Torr / Inert atmosphere 2: 3 h / Reflux View Scheme

: 5434-20-8
3-aminophthalic acid

: 6296-53-3
3-acetylaminophthalic anhydride

Conditions

Conditions	Yield
With acetic anhydride
With acetic anhydride
With acetic anhydride
With acetic anhydride
Multi-step reaction with 2 steps 1: hydrogenchloride / water / 15 h / 25 °C 2: water / 15 h / 100 °C View Scheme

: 108-24-7
acetic anhydride

: 6946-22-1
3-aminophthalic acid hydrochloride

: 6296-53-3
3-acetylaminophthalic anhydride

Conditions

Conditions	Yield
In water at 100℃; for 15h;	94 g
at 110℃; for 2h;	45 g
at 80 - 140℃; for 3h;

: 6296-53-3
3-acetylaminophthalic anhydride

: 151237-05-7
3,4,5-tris(dodec-1-yloxy)aniline

: 3-acetylamino-N-(3,4,5-tridodecyloxyphenyl)phthalimide

Conditions

Conditions	Yield
With acetic acid at 100℃; for 12h;	98%

: 6296-53-3
3-acetylaminophthalic anhydride

: 608141-42-0
(S)-2-[1 (3-ethoxy-4-methoxyphenyl)]-1-methanesulfonyl-2-ethylamine

: 608141-41-9
Apremilast

Conditions

Conditions	Yield
With acetic acid for 1h; Reflux; Large scale;	97%
With acetic acid In acetonitrile at 40℃; for 6h; Reflux;	94%
With acetic acid for 3h; Time; Reflux;	92%

: 6296-53-3
3-acetylaminophthalic anhydride

: 608141-43-1
(S)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethanamine-(S)-2-acetamido-4-methylpentanoate

: 608141-41-9
Apremilast

Conditions

Conditions	Yield
With triethylamine In ethyl acetate at 75 - 80℃; for 18h; Reagent/catalyst; Solvent;	95.1%
With sodium acetate; acetic acid at 80℃; for 5h; Reagent/catalyst; Temperature;	91.3%
Stage #1: (S)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethanamine-(S)-2-acetamido-4-methylpentanoate With sodium hydroxide In dichloromethane at 0 - 5℃; for 2h; Stage #2: 3-acetylaminophthalic anhydride With perchloric acid; acetic acid In dichloromethane at 45℃; for 3.33333h; Reflux;	89.2%

: 6296-53-3
3-acetylaminophthalic anhydride

: 24666-56-6
rac-α-aminoglutarimide hydrochloride

: 444289-17-2
N-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-4-yl)acetamide

Conditions

Conditions	Yield
With sodium acetate; acetic acid at 105℃; for 24h; Reagent/catalyst; Temperature;	95%

: 6296-53-3
3-acetylaminophthalic anhydride

: (1S)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylthio)ethan-1-amine

: 608141-41-9
Apremilast

Conditions

Conditions	Yield
Stage #1: 3-acetylaminophthalic anhydride; (1S)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylthio)ethan-1-amine With acetic acid In acetonitrile for 12h; Reflux; Stage #2: With sodium tungstate (VI) dihydrate; dihydrogen peroxide In acetonitrile at 20℃; for 7h; Cooling;	94%
Multi-step reaction with 2 steps 1.1: acetic acid / acetonitrile / 12 h / Reflux 2.1: acetic acid / acetonitrile / 20 °C 2.2: 7 h / 20 °C View Scheme

: 6296-53-3
3-acetylaminophthalic anhydride

: 608141-43-1
(S)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethanamine-(S)-2-acetamido-4-methylpentanoate

: 108-88-3
toluene

: apremilast hemitoluene

Conditions

Conditions	Yield
With acetic acid; sodium hydroxide In dichloromethane; water at 90℃; for 3h; Reagent/catalyst; Solvent;	91%

...Expand

: 6296-53-3
3-acetylaminophthalic anhydride

: 1258598-01-4
(S)-1-(3-(ethoxy-d5)-4-(methoxy-d3)phenyl)-2-(methylsulfonyl)ethanamine N-acetyl-L-leucine salt

: 1258597-45-3
(S)-N-(2-(1-(3-(ethoxy-d5)-4-(methoxy-d3)phenyl)-2-(methylsulfonyl)ethyl)-1,3-dioxoisoindolin-4-yl)acetamide

Conditions

Conditions	Yield
With acetic acid for 24h; Reflux;	89%
With acetic acid for 24h; Reflux;	89%

: 6296-53-3
3-acetylaminophthalic anhydride

: (S)-1-(3-(ethoxy-d5)-4-(methoxy-d3)phenyl)-2-(methylsulfonyl)ethylamine N-acetyl-L-leucine

: 1258597-45-3
(S)-N-(2-(1-(3-(ethoxy-d5)-4-(methoxy-d3)phenyl)-2-(methylsulfonyl)ethyl)-1,3-dioxoisoindolin-4-yl)acetamide

Conditions

Conditions	Yield
With acetic acid for 24h; Reflux;	89%

: 6296-53-3
3-acetylaminophthalic anhydride

: 1258597-97-5
(S)-1-(3-(ethoxy-d5)-4-(methoxy-d3)phenyl)-1-d-2-(methylsulfonyl)ethanamine N-acetyl-leucine salt

: 1258597-44-2
(S)-N-(2-(1-d-1-(3-(ethoxy-d5)-4-(methoxy-d3)phenyl)-2-(methylsulfonyl)ethyl)-1,3-dioxoisoindolin-4-yl)acetamide

Conditions

Conditions	Yield
Stage #1: 3-acetylaminophthalic anhydride; (S)-1-(3-(ethoxy-d5)-4-(methoxy-d3)phenyl)-1-d-2-(methylsulfonyl)ethanamine N-acetyl-leucine salt With acetic acid for 24h; Reflux; Stage #2: With sodium hydrogencarbonate In water	87%
With acetic acid for 24h; Reflux;	87%
With acetic acid for 24h; Reflux;	87%

: 109-99-9
tetrahydrofuran

: 6296-53-3
3-acetylaminophthalic anhydride

: 608141-42-0
(S)-2-[1 (3-ethoxy-4-methoxyphenyl)]-1-methanesulfonyl-2-ethylamine

: 2C22H24N2O7S*C4H8O

Conditions

Conditions	Yield
With acetic acid for 4h; Reagent/catalyst; Reflux;	87%

...Expand

: 6296-53-3
3-acetylaminophthalic anhydride

: 6118-65-6
3-acetamidophthalimide

Conditions

Conditions	Yield
With urea In N,N-dimethyl-formamide at 100℃; for 6h; Concentration; Temperature; Solvent;	85%

: 6296-53-3
3-acetylaminophthalic anhydride

: C12H19NO4S*C10H10ClNO5

: 608141-41-9
Apremilast

Conditions

Conditions	Yield
With acetic acid for 24h; Time; Reflux;	85%

: 6296-53-3
3-acetylaminophthalic anhydride

: 1258598-13-8
(S)-1-(3-(ethoxy-d5)-4-(methoxy-d3)phenyl)-2-((methyl-d3)sulfonyl)-2,2-d2-ethanamine N-acetyl-L-leucine salt

: 1258597-49-7
(S)-N-(2-(1-(3-(ethoxy-d5)-4-(methoxy-d3)phenyl)-2-((methyl-d3)sulfonyl)-2,2-d2-ethyl)-1,3-dioxoisoindolin-4-yl)acetamide

Conditions

Conditions	Yield
With deuteroacetic acid for 24h; Reflux;	84%
With acetic acid for 24h; Reflux;	84%
With acetic acid for 24h; Reflux;	84%

: 6296-53-3
3-acetylaminophthalic anhydride

: C13H21NO3S

: C23H26N2O6S

Conditions

Conditions	Yield
With formic acid In methanol at 30℃; for 12h; Reagent/catalyst;	84%

: 6296-53-3
3-acetylaminophthalic anhydride

: C17H19F2NO4S

: C27H24F2N2O7S

Conditions

Conditions	Yield
With acetic acid at 100 - 110℃; for 2h;	83.7%

: C2H4O2*C12H16N2O2

: 6296-53-3
3-acetylaminophthalic anhydride

: 882052-94-0
C22H21N3O5

Conditions

Conditions	Yield
With acetic acid for 17h;	83%

: 6296-53-3
3-acetylaminophthalic anhydride

: (R,R)-O,O’-di-p-toluoyl-tartrate

: 608141-41-9
Apremilast

Conditions

Conditions	Yield
With acetic acid for 24h; Reflux;	83%

: 109-99-9
tetrahydrofuran

: 6296-53-3
3-acetylaminophthalic anhydride

: C12H19NO4S*C10H10ClNO5

: 2C22H24N2O7S*C4H8O

Conditions

Conditions	Yield
Stage #1: tetrahydrofuran; C12H19NO4S*C10H10ClNO5 With potassium carbonate In dichloromethane; water at 30 - 33℃; for 0.5h; Stage #2: 3-acetylaminophthalic anhydride With acetic acid Reflux;	83%

...Expand

: 6296-53-3
3-acetylaminophthalic anhydride

: 608141-42-0
(S)-2-[1 (3-ethoxy-4-methoxyphenyl)]-1-methanesulfonyl-2-ethylamine

: C21H22N2O7S

Conditions

Conditions	Yield
In acetic acid butyl ester at 110 - 125℃; Temperature; Large scale;	80.4%

: 340020-00-0
R-4-amino-4-(3-ethoxy-4-methoxyphenyl)butan-2-ol

: 6296-53-3
3-acetylaminophthalic anhydride

: N-{2-[1-(R)-(3-ethoxy-4-methoxyphenyl)-3-hydroxybutyl]-1,3-dioxoisoindolin-4-yl}acetamide

Conditions

Conditions	Yield
With triethylamine at 80 - 90℃; for 7h;	80%

: 6296-53-3
3-acetylaminophthalic anhydride

: 1258598-09-2
((S)-1-(ethoxy-d5)-4-methoxyphenyl)-2-(methylsulfonyl)ethanamine N-acetyl-L-leucine salt

: 1258597-47-5
(S)-N-(2-(1-(3-(ethoxy-d5)-4-methoxyphenyl)-2-(methylsulfonyl)ethyl)-1,3-dioxoisoindolin-4-yl)acetamide

Conditions

Conditions	Yield
With acetic acid for 24h; Reflux;	80%
With acetic acid for 24h; Reflux;	80%
With acetic acid for 24h; Reflux;	80%

: 6296-53-3
3-acetylaminophthalic anhydride

: 608141-42-0
(S)-2-[1 (3-ethoxy-4-methoxyphenyl)]-1-methanesulfonyl-2-ethylamine

: 635705-72-5
4-amino-2-[(1S)-1-(3-ethoxy 4-methoxyphenyl)-2-methanesulfonylethyl]-2,3-dihydro-1H-isoindole-1,3-dione

Conditions

Conditions	Yield
With perchloric acid; acetic acid at 65 - 85℃; for 2.5h; Inert atmosphere; Reflux;	80%

: 6296-53-3
3-acetylaminophthalic anhydride

: 62-53-3
aniline

: 20871-13-0
3-acetylamino-N-phenylphthalimide

Conditions

Conditions	Yield
With acetic acid at 100℃; for 17h;	79%

: 6296-53-3
3-acetylaminophthalic anhydride

: (S)-1-(3-(ethoxy)-4-(methoxy-d3)phenyl)-2-(methylsulfonyl)ethylamine N-acetyl-L-leucine

: C22H21(2)H3N2O7S

Conditions

Conditions	Yield
Stage #1: (S)-1-(3-(ethoxy)-4-(methoxy-d3)phenyl)-2-(methylsulfonyl)ethylamine N-acetyl-L-leucine With sodium hydroxide In dichloromethane for 0.0833333h; Stage #2: 3-acetylaminophthalic anhydride With acetic acid In tetrahydrofuran at 70℃; for 24h;	79%

: 109-99-9
tetrahydrofuran

: 6296-53-3
3-acetylaminophthalic anhydride

: (R,R)-O,O’-di-p-toluoyl-tartrate

: 2C22H24N2O7S*C4H8O

Conditions

Conditions	Yield
Stage #1: (R,R)-O,O’-di-p-toluoyl-tartrate With potassium carbonate In dichloromethane; water at 30 - 33℃; for 0.5h; Stage #2: tetrahydrofuran; 3-acetylaminophthalic anhydride With acetic acid	79%

...Expand

: 340020-01-1
S-4-amino-4-(3-ethoxy-4-methoxyphenyl)butan-2-ol

: 6296-53-3
3-acetylaminophthalic anhydride

: N-{2-[1S-(3-ethoxy-4-methoxyphenyl)-3-hydroxybutyl]-1,3-dioxoisoindolin-4-yl}acetamide

Conditions

Conditions	Yield
With triethylamine In DMF (N,N-dimethyl-formamide) at 80 - 90℃; for 7h;	78%

: 6296-53-3
3-acetylaminophthalic anhydride

: 608142-27-4
(R)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)-ethylamine

: 608141-44-2
R-Apremilast

Conditions

Conditions	Yield
With acetic acid Microwave irradiation;	78%
With acetic acid Reflux;

Acetamide,N-(1,3-dihydro-1,3-dioxo-4-isobenzofuranyl)- Specification

The Acetamide,N-(1,3-dihydro-1,3-dioxo-4-isobenzofuranyl)- with CAS registry number of 6296-53-3 is also known as 3-Acetylaminophthalic anhydride. The IUPAC name is N-(1,3-Dioxo-2-benzofuran-4-yl)acetamide. In addition, the formula is C₁₀H₇NO₄ and the molecular weight is 205.17.

Physical properties about Acetamide,N-(1,3-dihydro-1,3-dioxo-4-isobenzofuranyl)- are: (1)ACD/LogP: 0.46; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.46; (4)ACD/LogD (pH 7.4): 0.46; (5)ACD/BCF (pH 5.5): 1.33; (6)ACD/BCF (pH 7.4): 1.33; (7)ACD/KOC (pH 5.5): 42.61; (8)ACD/KOC (pH 7.4): 42.61; (9)#H bond acceptors: 5; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 63.68Å²; (13)Index of Refraction: 1.657; (14)Molar Refractivity: 49.95 cm³; (15)Molar Volume: 135.6 cm³; (16)Polarizability: 19.8×10^-24cm³; (17)Surface Tension: 71.8 dyne/cm; (18)Density: 1.512 g/cm³; (19)Flash Point: 249.6 °C; (20)Enthalpy of Vaporization: 75.53 kJ/mol; (21)Boiling Point: 489.1 °C at 760 mmHg; (22)Vapour Pressure: 1.03E-09 mmHg at 25 °C

You can still convert the following datas into molecular structure:
1. SMILES: O=C1OC(=O)c2c1cccc2NC(=O)C
2. InChI: InChI=1/C10H7NO4/c1-5(12)11-7-4-2-3-6-8(7)10(14)15-9(6)13/h2-4H,1H3,(H,11,12)
3. InChIKey: PAUAJOABXCGLCN-UHFFFAOYAP
4. Std. InChI: InChI=1S/C10H7NO4/c1-5(12)11-7-4-2-3-6-8(7)10(14)15-9(6)13/h2-4H,1H3,(H,11,12)
5. Std. InChIKey: PAUAJOABXCGLCN-UHFFFAOYSA-N

Product Name

Acetamide,N-(1,3-dihydro-1,3-dioxo-4-isobenzofuranyl)-

Synthetic route

Acetamide,N-(1,3-dihydro-1,3-dioxo-4-isobenzofuranyl)- Specification

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