Guidechem | China Chemical Manufacturers,suppliers,B2B Marketplace
  • Products
  • Encyclopedia
  • Buy offers
  • Suppliers
Home> Encyclopedia >Agrochemical Intermediates>Pharmaceutical Intermediates>Organic Intermediate
6-Bromoisatin structure
6-Bromoisatin structure


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

Orange Powder

View more+
1. Names and Identifiers
1.1 Name
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.
1.4 CID
1.6 Molecular Formula
C8H4BrNO2 (isomer)
1.7 Inchi
1.8 InChkey
1.9 Canonical Smiles
1.10 Isomers Smiles
2. Properties
2.1 Density
2.1 Melting point
2.1 Refractive index
2.1 Precise Quality
2.1 PSA
2.1 logP
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
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
4. Safety and Handling
4.1 Hazard Codes
4.1 Risk Statements
4.1 Safety Statements
4.1 Hazard Class
4.1 Hazard Declaration
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

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

Signal word


Hazard statement(s)

H315 Causes skin irritation

H319 Causes serious eye irritation

H335 May cause respiratory irritation

Precautionary statement(s)

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.


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.


P403+P233 Store in a well-ventilated place. Keep container tightly closed.

P405 Store locked up.


P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification


8. Other Information
8.0 Mesh Entry Terms
8.1 Chemical Properties
Orange Powder
8.2 Uses
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
10. Recommended Suppliers
Global101SuppliersView all >>
  • Products:Manufacture & Supply Biopharm Chemical, Specialty Chemical, PetroChemical.
  • Tel:86-592-8883942
Factory Supply 6-Bromoisatin
  • Purity:99%Packing: 200kg/bag FOB
  • Price: 0.1 USD/kilogram
  • Time: 2023/03/01
  • Products:Chemical products
  • Tel:86-571-88938639
  • Purity:99%Packing: 200kg/bag FOB
  • Price: 2 USD/kilogram
  • Time: 2023/06/02
  • Products:Pharmaceutical, chemical technology research and development
  • Tel:086-0532-80960264
  • Purity:99%Packing: 200kg/bag FOB
  • Price: 1 USD/kilogram
  • Time: 2023/06/05
  • Products:Our company is an internationally oriented research based pharmaceutical company with headquarters located in Hangzhou,China.
  • Tel:86-571-87758773
  • Purity:99%Packing: 200kg/bag FOB
  • Price:  
  • Time: 2023/05/31
  • Products:Pharmaceutical intermediates
  • Tel:+86-25-83208295
  • Purity:99%Packing: 200kg/bag FOB
  • Price:  
  • Time: 2019/05/29
11. Realated Product Infomation