5-Bromophthalide
- Product Name
- 5-Bromophthalide
- CAS No.
- 64169-34-2
- Chemical Name
- 5-Bromophthalide
- Synonyms
- 5-bromoisobenzofuran-1(3H)-one;5-broMo-1,3-dihydro-2-benzofuran-1-one;ROXA-024;5-BromophthaL;5-Bromophthali;5-BROMOPHTHALIDE;5-Bromophathalide;5-Bromophthalide,98%;5-Bromophthalide 97%;5-Bromophthalide >
- CBNumber
- CB3157943
- Molecular Formula
- C8H5BrO2
- Formula Weight
- 213.03
- MOL File
- 64169-34-2.mol
5-Bromophthalide Property
- Melting point:
- 162-166 °C(lit.)
- Boiling point:
- 377.7±42.0 °C(Predicted)
- Density
- 1.742±0.06 g/cm3(Predicted)
- storage temp.
- Inert atmosphere,Room Temperature
- solubility
- Soluble in acetone.
- form
- Crystalline Powder
- color
- Beige to light yellow
- InChI
- InChI=1S/C8H5BrO2/c9-6-1-2-7-5(3-6)4-11-8(7)10/h1-3H,4H2
- InChIKey
- IUSPXLCLQIZFHL-UHFFFAOYSA-N
- SMILES
- C1(=O)C2=C(C=C(Br)C=C2)CO1
- CAS DataBase Reference
- 64169-34-2(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
- 647187
- Product name
- 5-Bromophthalide
- Purity
- 97%
- Packaging
- 5g
- Price
- $29.97
- Updated
- 2025/07/31
- Product number
- 647187
- Product name
- 5-Bromophthalide
- Purity
- 97%
- Packaging
- 25g
- Price
- $79.1
- Updated
- 2025/07/31
- Product number
- B2770
- Product name
- 5-Bromophthalide
- Packaging
- 5G
- Price
- $31
- Updated
- 2025/07/31
- Product number
- B2770
- Product name
- 5-Bromophthalide
- Purity
- >98.0%(GC)
- Packaging
- 25g
- Price
- $94
- Updated
- 2025/07/31
- Product number
- B686570
- Product name
- 5-Bromophthalide
- Packaging
- 10g
- Price
- $70
- Updated
- 2021/12/16
5-Bromophthalide Chemical Properties,Usage,Production
Chemical Properties
5-Bromophthalide is white to Pale Yellow Crystalline Solid
Uses
5-Bromophthalide is a useful synthetic intermediate
Uses
5-Bromophthalide is an important organic intermediate. It can be used in agrochemical, pharmaceutical and dyestuff field. It is a key intermediate of citalopram.
Synthesis
65399-05-5
64169-34-2
The general procedure for the synthesis of 5-bromophthalide from 5-aminophthalide was as follows: first, 5-nitrophthalimide (8) was prepared by nitration of phthalimide (7), using 200 g of phthalimide (7) in a mixture of HNO3 and H2SO4 acids at 0 °C to give 146 g of the product (8) in 56% yield. Subsequently, 8 was reduced to amine 9 by catalytic hydrogenation, using 5% Pd/C as catalyst, in EtOAc solvent in 97% yield. This step encountered the bottleneck of high solvent usage in large-scale operation. The improved method used the catalytic reduction reaction of zinc powder and copper(II) sulfate in 6 M NaOH aqueous solution to prepare aminophthalide 10 directly from 8 in one step in 100% yield, which effectively solved the bottleneck problem. Aminophthalide 10 was converted to 5-bromophthalide 11 in 76% yield by the Sandmeyer reaction in the presence of NaNO2 and 4 M HBr at 0 °C, followed by the addition of CuBr. A single batch yielded 36 g of 11. Next, 11 was reduced by diisobutylaluminum hydride (DIBAL) in toluene at -42 °C to give bromolactone 12 in 77% yield . Finally, 12 was reacted with boron trifluoride ether compounds in methanol to prepare bromoacetal 6 in 96% yield. The whole synthetic route was efficient and only the last two steps (e and f) required purification of the product by chromatography.
References
[1] Patent: US2011/77394, 2011, A1. Location in patent: Page/Page column 15
[2] Patent: CN108383833, 2018, A. Location in patent: Paragraph 0013
[3] Journal of the Chemical Society, 1931, p. 867,869
[4] Journal of Heterocyclic Chemistry, 2006, vol. 43, # 5, p. 1195 - 1204
[5] European Journal of Medicinal Chemistry, 2010, vol. 45, # 5, p. 1941 - 1946
5-Bromophthalide Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from 5-Bromophthalide manufacturers
- Product
- 5-Bromophthalide 64169-34-2
- Price
- US $0.00-0.00/g
- Min. Order
- 0.001g
- Purity
- 0.99
- Supply Ability
- 1 tons
- Release date
- 2024-11-15
- Product
- 5-Bromophthalide 64169-34-2
- Price
- US $400.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 10000KG
- Release date
- 2020-10-24
- Product
- 5-Bromophthalide 64169-34-2
- Price
- US $1.00/KG
- Min. Order
- 1KG
- Purity
- 98%
- Supply Ability
- 100KG
- Release date
- 2018-08-20