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Basic Information

Molecular Structure:
CAS No.:	443-69-6
Name:	5-Fluoroisatin
Article Data:	70

Formula:	C₈H₄FNO₂
Molecular Weight:	165.124
Synonyms:	5-fluoro-1H-indole-2,3-dione;1H-Indole-2,3-dione, 5-fluoro-;
EINECS:	-0
Density:	1.446 g/cm³
Melting Point:	224-227 °C(lit.)
Boiling Point:	417.9oC at 760mmHg
Flash Point:	206.5oC
Appearance:	red crystalline powder
Hazard Symbols:	Xi
Risk Codes:	36/37/38
Safety:	26-37/39-36
PSA:	46.17000
LogP:	1.09850

Synthetic route

: 351-09-7
N-(4-fluorophenyl)-2-(hydroxyimino) acetamide

: 443-69-6
5-fluoro-1H-indole-2,3-dione

Conditions

Conditions	Yield
With sulfuric acid In water at 80℃; for 0.333333h;	88.6%
With sulfuric acid In water at 50 - 75℃; Temperature;	88.2%
With sulfuric acid at 20℃;	85%

: N-(4-fluorophenyl)-2-(hydroxyimino)acetamide

: 443-69-6
5-fluoro-1H-indole-2,3-dione

Conditions

Conditions	Yield
With sulfuric acid at 50 - 75℃; for 0.333333h;	88.2%

: 2343-22-8
5-fluoroindoline

: 443-69-6
5-fluoro-1H-indole-2,3-dione

Conditions

Conditions	Yield
With iodine pentoxide In dimethyl sulfoxide at 80℃;	87%
With o-iodosobenzoic acid; oxygen In dimethyl sulfoxide at 80℃; for 12h; Green chemistry;	72%

: 1174558-44-1
3-(4-fluorophenylimino)-5-fluoro-N-(4-fluorophenyl)-3H-indole-2-amine

: 443-69-6
5-fluoro-1H-indole-2,3-dione

Conditions

Conditions	Yield
With hydrogenchloride; acetic acid In water for 0.333333h; Reflux;	85%

: 56341-41-4
5-fluoroindol-2(3H)-one

A: 443-69-6
5-fluoro-1H-indole-2,3-dione

B: (E)-5-fluoro-5'-methoxy-[3,3'-biindolinylidene]-2,2'-dione

Conditions

Conditions	Yield
With oxygen; sodium iodide In tetrahydrofuran at 60℃; for 12h; Schlenk technique; chemoselective reaction;	A 80% B 8%

: 201230-82-2
carbon monoxide

: N'-(2-bromo-4-fluorophenyl)-N,N-dimethylurea

: 443-69-6
5-fluoro-1H-indole-2,3-dione

Conditions

Conditions	Yield
Stage #1: N'-(2-bromo-4-fluorophenyl)-N,N-dimethylurea With methyllithium In tetrahydrofuran; diethyl ether at 0℃; Stage #2: With tert.-butyl lithium In tetrahydrofuran; diethyl ether; n-heptane at 0℃; for 1h; Stage #3: carbon monoxide In tetrahydrofuran; diethyl ether; n-heptane at 0℃; for 0.5h;	79%
Yield given; Multistep reaction;

: phenylglycine isopropyl ester

: 371-40-4
4-fluoroaniline

: 443-69-6
5-fluoro-1H-indole-2,3-dione

Conditions

Conditions	Yield
In acetonitrile at 60℃; for 16h;	78.7%

: 399-52-0
5-fluoro-1H-indole

: 443-69-6
5-fluoro-1H-indole-2,3-dione

Conditions

Conditions	Yield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; oxygen In acetonitrile at 20℃; for 18h;	68%

: 302-17-0
chloral hydrate

: 371-40-4
4-fluoroaniline

: 443-69-6
5-fluoro-1H-indole-2,3-dione

Conditions

Conditions	Yield
Stage #1: chloral hydrate; 4-fluoroaniline With hydrogenchloride; hydroxylamine hydrochloride; sodium sulfate In water Stage #2: With sulfuric acid at 60 - 80℃;	63%
Stage #1: chloral hydrate; 4-fluoroaniline With hydrogenchloride; hydroxylamine hydrochloride; sodium sulfate for 0.166667h; Heating; Stage #2: With sulfuric acid for 1h; Heating;
Stage #1: chloral hydrate; 4-fluoroaniline With hydroxylamine hydrochloride; sodium sulfate In water Sandmeyer reaction; Stage #2: With sulfuric acid In methanol Sandmeyer reaction;

: 4-Fluoroisonitrosoacetanilide

: 443-69-6
5-fluoro-1H-indole-2,3-dione

Conditions

Conditions	Yield
With sulfuric acid 1) 50 deg C, 30 min; 2) 80 deg C, 10 min;	62%

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Specification

The 5-Fluoroindoline-2,3-dione is an organic compound with the formula C₈H₄FNO₂. The IUPAC name of this chemical is 5-fluoro-1H-indole-2,3-dione. With the CAS registry number 443-69-6, it is also named as 1H-Indole-2,3-dione, 5-fluoro-. The product's categories are Isatin Series; Blocks; Indoles Oxindoles; Indole/indoline/oxindole; Indole and Indoline; Indane/Indanone and Derivatives; Sunitinib; Heterocyclic Compounds; Indoles; Simple Indoles; Heterocycles; Intermediates & Fine Chemicals; Pharmaceuticals; Boronic Acid; Building Blocks; Heterocyclic Building Blocks; Fluorinated Heterocyclic Series. Besides, it is a red crystalline powder, which is the intermediates of cardiovascular and anti-inflammatory drugs.

Physical properties about 5-Fluoroindoline-2,3-dione are: (1)ACD/LogP: 0.61 ; (2)ACD/LogD (pH 5.5): 0.61; (3)ACD/LogD (pH 7.4): 0.58; (4)ACD/BCF (pH 5.5): 1.71; (5)ACD/BCF (pH 7.4): 1.59; (6)ACD/KOC (pH 5.5): 51.14; (7)ACD/KOC (pH 7.4): 47.53; (8)#H bond acceptors: 3; (9)#H bond donors: 1; (10)Polar Surface Area: 37.38 Å²; (11)Index of Refraction: 1.584; (12)Molar Refractivity: 37.41 cm³; (13)Molar Volume: 111.7 cm³; (14)Polarizability: 14.83×10^-24cm³; (15)Surface Tension: 50.8 dyne/cm; (16)Density: 1.477 g/cm³.

Preparation: this chemical can be prepared by hydroxyimino-acetic acid-(4-fluoro-anilide). This reaction will need reagent sulfuric acid.

Uses of 5-Fluoroindoline-2,3-dione: it can be used to produce 6-fluoro-1H-benzo[d][1,3]oxazine-2,4-dione. It will need reagent CrO₃ and acetic acid.

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. When you are using it, wear suitable gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: Fc1cc2c(cc1)NC(=O)C2=O
(2)InChI: InChI=1/C8H4FNO2/c9-4-1-2-6-5(3-4)7(11)8(12)10-6/h1-3H,(H,10,11,12)
(3)InChIKey: GKODDAXOSGGARJ-UHFFFAOYAY
(4)Std. InChI: InChI=1S/C8H4FNO2/c9-4-1-2-6-5(3-4)7(11)8(12)10-6/h1-3H,(H,10,11,12)
(5)Std. InChIKey: GKODDAXOSGGARJ-UHFFFAOYSA-N