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87-48-9

Basic Information
CAS No.: 87-48-9
Name: 5-Bromoisatin
Article Data: 106
Molecular Structure:
Molecular Structure of 87-48-9 (5-Bromoisatin)
Formula: C8H4BrNO2
Molecular Weight: 226.029
Synonyms: Indole-2,3-dione,5-bromo- (7CI,8CI);Isatin, 5-bromo- (6CI);5-Bromo-1H-indole-2,3-dione;5-Bromo-2,3-indolinedione;5-Bromoindole-2,3-dione;NSC 4980;
EINECS: 201-747-7
Density: 1.826 g/cm3
Melting Point: 251-253 °C
Boiling Point: 136ºC
Appearance: Orange crystalline powder
Hazard Symbols: IrritantXi
Risk Codes: 37/38-41
Safety: 26-36/39-37/39-36
Transport Information: UN 2811
PSA: 46.17000
LogP: 1.72190
Synthetic route
66475-83-0

N-(4-bromophenyl)-2-(N-hydroximino)acetamide

87-48-9

5-Bromo-1H-indole-2,3-dione

Conditions
ConditionsYield
With sulfuric acid at 60 - 80℃; for 0.166667h;96%
With sulfuric acid at 60 - 80℃;89%
With sulfuric acid at 70℃; for 0.00277778h; Microwave irradiation;88%
20870-78-4

5-bromo-2-indolin-2-one

87-48-9

5-Bromo-1H-indole-2,3-dione

Conditions
ConditionsYield
With oxygen; copper(II) acetate monohydrate; potassium carbonate In N,N-dimethyl-formamide at 50℃; under 760.051 Torr; for 0.5h;96%
With tert.-butylnitrite; oxygen In tetrahydrofuran at 50℃; under 760.051 Torr; for 24h; Schlenk technique; Inert atmosphere;85%
With oxygen; sodium iodide In tetrahydrofuran at 60℃; for 12h; Schlenk technique; chemoselective reaction;83%

3-iodo-5-bromo-1H-indole

87-48-9

5-Bromo-1H-indole-2,3-dione

Conditions
ConditionsYield
With N-iodo-succinimide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide at 25 - 35℃; for 7h;94%
91-56-5

indole-2,3-dione

87-48-9

5-Bromo-1H-indole-2,3-dione

Conditions
ConditionsYield
With bromine; acetic acid at 0℃;89.43%
With tribromo-isocyanuric acid In trifluoroacetic acid at 20℃; for 0.5h;85%
With N-Bromosuccinimide In acetonitrile at 20℃; for 96h;77%

C9H4BrN3O2

87-48-9

5-Bromo-1H-indole-2,3-dione

Conditions
ConditionsYield
With copper(I) bromide In water; benzonitrile at 140℃; for 4h; Inert atmosphere;88%
10075-50-0

5-bromo-1H-indole

87-48-9

5-Bromo-1H-indole-2,3-dione

Conditions
ConditionsYield
With pyridinium chlorochromate In 1,2-dichloro-ethane at 80℃; for 2.5h;87%
With indium(III) chloride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In water; acetonitrile at 80℃; for 2h;86%
With N-iodo-succinimide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide at 15 - 25℃; for 3h;86%
22190-33-6

5-bromoindoline

87-48-9

5-Bromo-1H-indole-2,3-dione

Conditions
ConditionsYield
With iodine pentoxide In dimethyl sulfoxide at 80℃;86%
With o-iodosobenzoic acid; oxygen In dimethyl sulfoxide at 80℃; for 12h; Green chemistry;78%
877-03-2

5-bromo-1H-indole-3-carboxaldehyde

87-48-9

5-Bromo-1H-indole-2,3-dione

Conditions
ConditionsYield
With sodium chloride In water; acetonitrile at 50℃; for 2h; Green chemistry;85%
182344-70-3

5-bromo-indole-1-carboxylic acid tert-butyl ester

A

tert-butyl 5-bromo-3-iodo-1H-indole-1-carboxylate

B

87-48-9

5-Bromo-1H-indole-2,3-dione

Conditions
ConditionsYield
With N-iodo-succinimide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide at 15 - 25℃; for 3h;A 85%
B 5%
302-17-0

chloral hydrate

106-40-1

4-bromo-aniline

87-48-9

5-Bromo-1H-indole-2,3-dione

Conditions
ConditionsYield
Stage #1: chloral hydrate; 4-bromo-aniline With sulfuric acid; hydroxylamine hydrochloride; sodium sulfate In water at 130℃; for 1h;
Stage #2: With sulfuric acid at 50 - 70℃; for 1.5h;
78%
With hydrogenchloride; hydroxylamine hydrochloride; sodium sulfate In water at 90℃; for 0.0833333h;67.2%
Stage #1: chloral hydrate; 4-bromo-aniline With hydrogenchloride; hydroxylamine hydrochloride; sodium sulfate In water
Stage #2: With sulfuric acid at 60 - 80℃;
67%
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  • CAS No.87-48-9   5-Bromoisatin

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    Product Name: 5-Bromoisatin CAS: 87-48-9 MF: C8H4BrNO2 MW: 226.03 EINECS: 201-747-7 Mol File: 87-48-9.mol 5-Bromoisatin Structure 5-Bromoisatin Chemical Properties Melting point 247-252 °C (lit.) density 1.7498 (rough

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  • 87-48-9  CAS NO.87-48-9

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Specification

The 5-Bromoindole-2,3-dione with CAS registry number of 87-48-9 is also known as 5-Bromoisatin. The IUPAC name is 5-Bromo-1H-indole-2,3-dione. It belongs to product categories of Indole/indoline/oxindole; Indole and Indoline; Indane/Indanone and Derivatives; Indoles; Simple Indoles; Halogenated Heterocycles; Heterocyclic Building Blocks; IndolesBuilding Blocks. Its EINECS registry number is 201-747-7. In addition, the formula is C8H4BrNO2 and the molecular weight is 226.03. This chemical is a orange crystalline powder and should be sealed in cool, dry place.

Physical properties about 5-Bromoindole-2,3-dione are: (1)ACD/LogP: 1.33; (2)ACD/LogD (pH 5.5): 1.33; (3)ACD/LogD (pH 7.4): 1.31; (4)ACD/BCF (pH 5.5): 6.04; (5)ACD/BCF (pH 7.4): 5.78; (6)ACD/KOC (pH 5.5): 126.08; (7)ACD/KOC (pH 7.4): 120.73; (8)#H bond acceptors: 3; (9)#H bond donors: 1; (10)Index of Refraction: 1.649; (11)Molar Refractivity: 45.11 cm3; (12)Molar Volume: 123.7 cm3; (13)Surface Tension: 58.4 dyne/cm; (14)Density: 1.826 g/cm3.

Preparation of 5-Bromoindole-2,3-dione: it is prepared by reaction of indole-2,3-dione. The reaction needs reagents N-bromosaccharin, SiO2 and solvent CH2Cl2 at the temperature of 20 °C for 12 hours. The yield is about 58%.

5-Bromoindole-2,3-dione is prepared by reaction of indole-2,3-dione.

Uses of 5-Bromoindole-2,3-dione: it is used to produce 6-bromo-2-thiophen-2-yl-quinoline-4-carboxylic acid by reaction with 1-thiophen-2-yl-ethanone. The reaction occurs with solvents NaOH, water and other condition of heating for 2 hours. The yield is about 76%.

5-Bromoindole-2,3-dione is used to produce 6-bromo-2-thiophen-2-yl-quinoline-4-carboxylic acid by reaction with 1-thiophen-2-yl-ethanone.

When you are using this chemical, please be cautious about it. As a chemical, it is irritating to respiratory system and skin. What's more, it has risk of serious damage to eyes. During using it, wear suitable protective clothing, gloves and eye/face protection. If contact with eyes accidently, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
1. Canonical SMILES: C1=CC2=C(C=C1Br)C(=O)C(=O)N2
2. InChI: InChI=1S/C8H4BrNO2/c9-4-1-2-6-5(3-4)7(11)8(12)10-6/h1-3H,(H,10,11,12)
3. InChIKey: MBVCESWADCIXJN-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 437mg/kg (437mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION Pharmaceutical Chemistry Journal Vol. 15, Pg. 858, 1981.
mouse LD50 oral 3430mg/kg (3430mg/kg) BEHAVIORAL: EXCITEMENT

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 53(2), Pg. 93, 1988.
rat LD50 intraperitoneal 680mg/kg (680mg/kg) BEHAVIORAL: EXCITEMENT

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 53(2), Pg. 93, 1988.