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

pka

3.88±0.20(Predicted)

Appearance

White to yellow Solid

Water Solubility 

Soluble in water 1360 mg/L 25°C.

InChI

InChI=1S/C8H7NO2/c9-6-2-1-5-4-11-8(10)7(5)3-6/h1-3H,4,9H2

InChIKey

ZIJZDNKZJZUROE-UHFFFAOYSA-N

SMILES

C1(=O)C2=C(C=CC(N)=C2)CO1

CAS DataBase Reference

57319-65-0(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

• Language:English Provider:ALFA

6-AMINOPHTHALIDE Usage And Synthesis

Chemical Properties

white to light yellow crystal powde

Uses

It is used to produce 6-acetylamino-phthalide. It is also used as a starting material in the reduction reaction.

Uses

6-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.

Definition

ChEBI: 6-Amino-1,3-dihydroisobenzofuran-1-one is a member of 2-benzofurans.

Synthesis

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

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