6-AMINOPHTHALIDE

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CAS:57319-65-0
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Products Intro: Product Name:6-amino-1,3-dihydroisobenzofuran-1-one
CAS:57319-65-0
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  • CAS:57319-65-0
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6-AMINOPHTHALIDE Basic information
Product Name:6-AMINOPHTHALIDE
Synonyms:BUTTPARK 33\04-93;6-AMINO-2-BENZOFURAN-1(3H)-ONE;6-AMINO-1,3-DIHYDROISOBENZOFURAN-1-ONE;6-AMINOISOBENZOFURAN-1-ONE;6-AMINOPHTHALIDE;6-Aminophtalide;6-Aminophthalide,95%;6-Amino-1,3-dihydroisobenzofuran-1-one, 95+%
CAS:57319-65-0
MF:C8H7NO2
MW:149.15
EINECS:260-675-4
Product Categories:Miscellaneous;Amines;Furan&Benzofuran;Fused Ring Systems
Mol File:57319-65-0.mol
6-AMINOPHTHALIDE Structure
6-AMINOPHTHALIDE Chemical Properties
Melting point 183 °C
Boiling point 420.2±45.0 °C(Predicted)
density 1.376±0.06 g/cm3(Predicted)
storage temp. under inert gas (nitrogen or Argon) at 2–8 °C
pka3.88±0.20(Predicted)
AppearanceWhite to yellow Solid
Water Solubility Soluble in water 1360 mg/L 25°C.
InChIInChI=1S/C8H7NO2/c9-6-2-1-5-4-11-8(10)7(5)3-6/h1-3H,4,9H2
InChIKeyZIJZDNKZJZUROE-UHFFFAOYSA-N
SMILESC1(=O)C2=C(C=CC(N)=C2)CO1
CAS DataBase Reference57319-65-0(CAS DataBase Reference)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36-37/39
RIDADR UN2811
Hazard Note Irritant
HS Code 2932990090
MSDS Information
ProviderLanguage
ALFA English
6-AMINOPHTHALIDE Usage And Synthesis
Chemical Propertieswhite to light yellow crystal powde
UsesIt is used to produce 6-acetylamino-phthalide. It is also used as a starting material in the reduction reaction.
Uses6-Aminophthalide is used in the total synthesis of uncialamycin and its application to antitumor antibiotics. Also used in permethyl ningalin analogs as P-glycoprotein inhibitors.
DefinitionChEBI: 6-Amino-1,3-dihydroisobenzofuran-1-one is a member of 2-benzofurans.
Synthesis
6-Nitrophthalide

610-93-5

6-AMINOPHTHALIDE

57319-65-0

General procedure for the synthesis of 6-aminophthalide from 6-nitrotetrachlorophthalide: Commercially available 6-nitro-1(3H)-isobenzofuranone (9.9 g, 55 mmol) was dissolved in a solvent mixture of tetrahydrofuran (20 mL) and methanol (60 mL), and 5% palladium-carbon catalyst (1.5 g) was subsequently added. The reaction mixture was stirred at room temperature for 20 h under hydrogen atmosphere. Upon completion of the reaction, the mixture was filtered and the solid was washed sequentially with ethyl acetate and methanol. The filtrate and washings were combined and the resulting solution was concentrated under reduced pressure. The resulting solid was washed with ethyl acetate to give 6-aminophthalide (6.21 g) as a crystalline solid. The washings were concentrated and the residue was crystallized by mixed ethyl acetate-hexane solvent to obtain additional 6-aminophthalide (0.95 g, 87% total yield). The product was confirmed by NMR hydrogen spectrum (400 MHz, CD3OD): δ 5.225 (2H, s), 7.060 (1H, d, J = 2 Hz), 7.071 (1H, dd, J = 9, 2 Hz), 7.288 (1H, d, J = 9 Hz). Infrared spectra (KBr pressed) νmax cm-1: 3473, 3372, 3278, 1735, 1631, 1504, 1330, 1059, 992.

References[1] Physical Chemistry Chemical Physics, 2005, vol. 7, # 24, p. 4070 - 4081
[2] Chemistry - A European Journal, 2016, vol. 22, # 13, p. 4600 - 4607
[3] ACS Catalysis, 2014, vol. 4, # 10, p. 3504 - 3511
[4] Patent: EP1362856, 2003, A1. Location in patent: Page/Page column 159
[5] Journal of Heterocyclic Chemistry, 2006, vol. 43, # 5, p. 1195 - 1204
6-AMINOPHTHALIDE Preparation Products And Raw materials
Raw materials6-Nitrophthalide-->Methanol-->Tetrahydrofuran-->Hydrogen
Preparation Products5-CHLORO-2-FORMYL-BENZOIC ACID-->6-Cyanophthalide-->6-IODO-3 H-ISOBENZOFURAN-1-ONE
Tag:6-AMINOPHTHALIDE(57319-65-0) Related Product Information
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