5-Aminophthalide
- Product Name
- 5-Aminophthalide
- CAS No.
- 65399-05-5
- Chemical Name
- 5-Aminophthalide
- Synonyms
- Roxadustat-002;Einecs 265-731-1;5-Aminophthliade;5-AMINOPHTHALIDE;Aminophthalide,5-;TIMTEC-BB SBB007358;5-Aminophthalide ,98%;Roxadustat Impurity 91;5-AMINOPHENYL PHTHALEIN;5-amino-3H-2-benzofuran-1-one
- CBNumber
- CB7763102
- Molecular Formula
- C8H7NO2
- Formula Weight
- 149.15
- MOL File
- 65399-05-5.mol
5-Aminophthalide Property
- Melting point:
- 178 °C
- Boiling point:
- 438.6±45.0 °C(Predicted)
- Density
- 1.376±0.06 g/cm3(Predicted)
- storage temp.
- under inert gas (nitrogen or Argon) at 2–8 °C
- form
- Solid
- pka
- 2.10±0.20(Predicted)
- Appearance
- Light yellow to yellow Solid
- InChI
- InChI=1S/C8H7NO2/c9-6-1-2-7-5(3-6)4-11-8(7)10/h1-3H,4,9H2
- InChIKey
- ISMUWQMUWFPFBZ-UHFFFAOYSA-N
- SMILES
- C1(=O)C2=C(C=C(N)C=C2)CO1
- CAS DataBase Reference
- 65399-05-5(CAS DataBase Reference)
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P405Store locked up.
N-Bromosuccinimide Price
- Product number
- A577133
- Product name
- 5-Aminophthalide
- Packaging
- 500mg
- Price
- $90
- Updated
- 2021/12/16
- Product number
- FA70724
- Product name
- 5-Aminophthalide
- Packaging
- 500mg
- Price
- $65
- Updated
- 2021/12/16
- Product number
- FA70724
- Product name
- 5-Aminophthalide
- Packaging
- 1g
- Price
- $100
- Updated
- 2021/12/16
- Product number
- FA70724
- Product name
- 5-Aminophthalide
- Packaging
- 2g
- Price
- $140
- Updated
- 2021/12/16
- Product number
- OR927089
- Product name
- 5-Aminophthalide
- Purity
- 95%
- Packaging
- 250mg
- Price
- $175
- Updated
- 2021/12/16
5-Aminophthalide Chemical Properties,Usage,Production
Synthesis
3676-85-5
65399-05-5
The general steps for the synthesis of 5-aminophthalide from 4-amino phthalimide are as follows: first, phthalimide (7) undergoes a bromoacetal reaction to produce compound 6, as shown in Figure 1. According to the literature, these transformations have been carried out on a large scale and some of the steps have been optimized. The specific operation included the nitration of 200 g of phthalimide (7) to obtain 146 g of 5-nitrophthalimide (8). Subsequently, a 2L Parr hydrogenator pressure vessel was used to reduce 30 g of 8 by catalytic hydrogenation to 25 g of amine 9. This step was the bottleneck of the synthesis due to the large amount of solvent required. Next, aminophthalide 10 was quantitatively obtained from 9 by a copper-catalyzed reaction of zinc in an aqueous base.Steps b and c can be combined, i.e., treatment of 8 with zinc powder and copper(II) sulfate in a 2 M NaOH aqueous solution.This modification is not demonstrated in Fig. 1. The one-step preparation of 100 g of 10 from 146 g of 9 may be achieved by eliminating the bottleneck step, as shown in FIG. 11. The steps detailed in FIG. 11 include: a) reaction using HNO3 and H2SO4 at 0 °C in 56% yield; b) 5% Pd/C catalyzed hydrogenation in EtOAc in 97% yield; c) reaction with Zn and CuSO4 in 6 M NaOH at 5 °C. followed by heating at 70-80°C for 16 h in 100% yield; d) treatment with NaNO2 and 4 M HBr at 0°C, followed by the addition of CuBr; e) reaction with DIBAL in toluene at -42°C; f) treatment with BF3-OEt2 and MeOH at room temperature.
References
[1] Tetrahedron, 1998, vol. 54, # 26, p. 7485 - 7496
[2] Patent: US2011/77394, 2011, A1. Location in patent: Page/Page column 15
[3] Archiv der Pharmazie, 1985, vol. 318, # 7, p. 640 - 648
[4] Patent: CN108383833, 2018, A. Location in patent: Paragraph 0012
[5] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 1, p. 53 - 56
5-Aminophthalide Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from 5-Aminophthalide manufacturers
- Product
- 5-Aminophthalide 65399-05-5
- Price
- US $7.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 1000KG
- Release date
- 2018-08-21