6-Bromoisatin
- Iupac Name：6-bromo-1H-indole-2,3-dione
- CAS No.: 6326-79-0
- Molecular Weight：226.02686
- Modify Date.: 2022-11-29 08:20
- Introduction:
Orange Powder
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1. Names and Identifiers
- 1.1 Name
- 6-Bromoisatin
- 1.2 Synonyms
1H-6-bromoindole-2,3-dione 1H-Indole-2,3-dione, 6-bromo- 6-BROMO ISATINIC ANHYDRIDE 6-bromo-1H-benzo[d]azolidine-2,3-dione 6-BROMO-1H-INDOLE-2,3-DIONE 6-bromo-2,3-dihydro-1H-indole-2,3-dione 6-BROMOINDOLE-2,3-DIONE 6-BROMOINDOLINE-2,3-DIONE 6-Bromo-Isatin 6-Bromoisatin 6-Bromo indole-2,3-dione 6-monobromoisatin AKOS B018432 BROMOISATIN(6-) BUTTPARK 50\07-95 MFCD01631138
- 1.3 CAS No.
- 6326-79-0
- 1.4 CID
- 95716
- 1.5 EINECS(EC#)
- 678-162-2
- 1.6 Molecular Formula
- C8H4BrNO2 (isomer)
- 1.7 Inchi
- InChI=1S/C8H4BrNO2/c9-4-1-2-5-6(3-4)10-8(12)7(5)11/h1-3H,(H,10,11,12)
- 1.8 InChkey
- HVPQMLZLINVIHW-UHFFFAOYSA-N
- 1.9 Canonical Smiles
- C1=CC2=C(C=C1Br)NC(=O)C2=O
- 1.10 Isomers Smiles
- C1=CC2=C(C=C1Br)NC(=O)C2=O
2. Properties
- 2.1 Density
- 1.826
- 2.1 Melting point
- 274°C
- 2.1 Refractive index
- 1.649
- 2.1 Precise Quality
- 224.94300
- 2.1 PSA
- 46.17000
- 2.1 logP
- 1.72190
- 2.1 Appearance
- Orange Powder
- 2.2 Storage
- -20°C Freezer
- 2.3 Chemical Properties
- Orange Powder
- 2.4 Color/Form
- Light-red to Brown Solid
- 2.5 pKa
- 8.83±0.20(Predicted)
- 2.6 StorageTemp
- Keep in dark place,Sealed in dry,Room Temperature
3. Use and Manufacturing
- 3.1 Methods of Manufacturing
- Step 2: 6-Bromo-lH-indole-2, 3-dioneTo the concentrated sulfuric acid (275 mL) at 50 °C was added N-(3-Bromo- phenyl)-2-hydroxyimino-acetamide (55 g, 0.2272 mol). The temperature was raised to 90 °C and maintained for 3 h. The reaction mixture was added to ice cold water to get yellow precipitate. The precipitate was filtered and dried to get the title compound as a yellow solid [50 g, 98percent]. This material was taken to the next step without any further purification6-bromo-1 /-/-indole-2, 3-dioneTo sulfuric acid (2.3 L) at 60°C was added A/-(3-bromophenyl)-2- (hydroxyimino)ethanamide (1 10 g, 456.43 mmol) portionwise over 30 minutes such that the temperature of the reaction mixture did not exceed 65°C. The mixture was heated to 80°C for 15 minutes, cooled to 70°C, and poured onto crushed ice. The ice mixture was allowed to stand for 1 h. Solids were collected by filtration, washed with water, and dried. The crude material was dissolved in a solution of NaOH (58 g) in water at 60°C and acidified with acetic acid. After standing for 0.5 h, the mixture was cooled to 35°C. Solids were collected by filtration and washed with a minimal amount of water. The filter cake was set aside. The filtrate was acidified with concentrated HCI and allowed to stand for 2 h at 5°C. Solids were collected by filtration and washed with water. The combined filter cakes were dried in vacuo to afford 6-bromo-1 H-indole-2, 3-dione (33 g, 32percent yield). To concentrated sulfuric acid (275 mL) at 50° C. was added N-(3-bromo-phenyl)-2-hydroxyimino-acetamide (55 g, 0.2272 mol). The temperature was raised to 90° C. and maintained for 3 hours. The reaction mixture was added to ice cold water to provide a yellow precipitate. The precipitate was filtered and dried to provide the title compound as a yellow solid (50 g, 98percent). This material was taken for next step without any further purification.Example 59; Preparation of A33; Synthesis of 4-Bromoisatin (K-98) and 6-Bromoisatin (K-99); To a solution chloral hydride (50.0 g, 0.247 mol) in water (237mL) were successively added NaSulfuric acid (1 L) was heated in a 3 L beaker on a hot plate to 60 °C and then removed. The dry isonitrosoacetanilide 2a-f was added in portion with stirring over 30 min so that the temperature did not exceed 65 °C. The mixture was then heated to 80 °C for 15 min, allowed to cool to 70 °C and cooled on ice. The solution was poured onto crushed ice (5 L) and left to stand for 1 h before filtering the orange-red precipitate. The product was washed by stirring with water (400 mL) and filtered to give a mixture of 3a-f and 4a-f. The crude product was dissolved in a solution of NaOH (20 g) in water (200 mL) at 60 °C, and then acidified with acetic acid (60 mL). After standing 0.5 h and cooling to 35 °C, the 4a-4f precipitate was filtered and washed with water (50 mL). The combined filtrate and washings were acidified with conc. HCL (60mL) and, after standing for 2 h at 5 °C, the 3a-f precipitate was filtered off and washed with water (50 mL). Yields: 3a: 27percent, 3b: 14percent, 3c : 29percent, 3d: 22percent, 3e: 33percent, 3f : 31percent, 4a: 56percent, 4b: 64percent, 4c: 53percent, 4d: 59percent, 4e: 49percent, 4f : 51percent.10.00 g (58.13 mmol) of 3-bromoaniline was placed in a 1000 mL round bottom flask, 500 mL of water was added, (45.343 mmol) of anhydrous sodium sulfate and 13.33 g (191.84 mmol) of hydrochloric acid light were added under stirring. Then, 10 mL of a 2 mol / L hydrochloric acid solution was added and stirred at room temperature for 5 min.Finally, 10.58 g (63.95 mmol) of chloral hydrate was added. The reaction mixture was stirred at room temperature for 15 min, then heated at 90 ° C under reflux reaction 2KTLC detection of raw materials disappeared, Then cooled to room temperature, filtered and vacuum dried to give 12.90 g of a pale yellow solid. 0 mL of concentrated sulfuric acid was added to a 100 mL round bottom flask and 12.90 g of a yellow solid was slowly added to concentrated sulfuric acid at 50 ° C and reacted at 65 ° C for 30 min after complete addition.After the reaction, the reaction mixture was cooled to room temperature. The reaction mixture was poured into an ice-water mixture and stirred for 30 minutes. The solid was filtered by suction filtration and dried in a vacuum oven. Petroleum ether: ethyl acetate = To give 4.12 g of 6-bromoindolinedione in a yield of 31.4percent.
- 3.2 Purification Methods
- 6-Bromoisatin recrystallises from AcOH (yellow needles). It is a plant growth substance. IR in CHCl3 has 1320 and 3440cm-1. [Sadler J Org max Chem 21 169 1956, Beilstein 21 III/IV 5012.] 6-Bromoisatin Preparation Products And Raw materials Raw materials
- 3.3 Usage
- Antimicrobial
4. Safety and Handling
- 4.1 Hazard Codes
- Xi
- 4.1 Risk Statements
- R22
- 4.1 Safety Statements
- S22;S24/25
- 4.1 Hazard Class
- IRRITANT
- 4.1 Hazard Declaration
- H302
- 4.1 Caution Statement
- P261, P264, P270, P271, P272, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P333+P313, P337+P313, P362, P363, P403+P233, P405, P501
5. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
Skin irritation, Category 2
Eye irritation, Category 2
Specific target organ toxicity \u2013 single exposure, Category 3
2.2 GHS label elements, including precautionary statements
| Pictogram(s) |  |
| Signal word | Warning |
| Hazard statement(s) | H315 Causes skin irritation H319 Causes serious eye irritation H335 May cause respiratory irritation |
| Precautionary statement(s) | |
| Prevention | P264 Wash ... thoroughly after handling. P280 Wear protective gloves/protective clothing/eye protection/face protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area. |
| Response | P302+P352 IF ON SKIN: Wash with plenty of water/... P321 Specific treatment (see ... on this label). P332+P313 If skin irritation occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P312 Call a POISON CENTER/doctor/\u2026if you feel unwell. |
| Storage | P403+P233 Store in a well-ventilated place. Keep container tightly closed. P405 Store locked up. |
| Disposal | P501 Dispose of contents/container to ... |
2.3 Other hazards which do not result in classification
none
6. Synthesis Route
6326-79-0Total: 7 Synthesis Route
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Literatures:
ENDO PHARMACEUTICALS INC.; SMITH, Roger, Astbury; THOMPSON, Scott, Kevin; HOSAHALLI, Subramanya; BEJUGAM, Mallesham; NANDURI, Srinivas; PANIGRAHI, Sunil, Kumar; MAHALINGAM, Natarajan Patent: WO2012/58671 A1, 2012 ; Location in patent: Page/Page column 91 ;
Yield: ~99%
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8. Other Information
- 8.0 Mesh Entry Terms
- 6-bromoisatin
- 8.1 Chemical Properties
- Orange Powder
- 8.2 Uses
- Antimicrobial
- 8.3 Purification Methods
- 6-Bromoisatin recrystallises from AcOH (yellow needles). It is a plant growth substance. IR in CHCl3 has 1320 and 3440cm-1. [Sadler J Org max Chem 21 169 1956, Beilstein 21 III/IV 5012.]
9. Computational chemical data
- Molecular Weight: 226.02686g/mol
- Molecular Formula: C8H4BrNO2
- Compound Is Canonicalized: True
- XLogP3-AA: null
- Exact Mass: 224.94254
- Monoisotopic Mass: 224.94254
- Complexity: 241
- Rotatable Bond Count: 0
- Hydrogen Bond Donor Count: 1
- Hydrogen Bond Acceptor Count: 2
- Topological Polar Surface Area: 46.2
- Heavy Atom Count: 12
- Defined Atom Stereocenter Count: 0
- Undefined Atom Stereocenter Count: 0
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Isotope Atom Count: 0
- Covalently-Bonded Unit Count: 1
- CACTVS Substructure Key Fingerprint: AAADcYByMAAAEAAAAAAAAAAAAAAAAWAAAAAwAAAAAAAAAFgBAAAAHgBQAAABrAyBmAAwwILAAACIAqVSUACCAAAlAgQIiAGAZOgIIDrAlbGEIYhglADIy9cciICOAgAAAAECAAAEAAAAAgQAAAAAAAAAAA==
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11. Realated Product Infomation
-120YR
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