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84-40-2

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84-40-2 Usage

Preparation

(a) 3H-indol-3-one,2-(1,3-dihydro-3-oxo-2H-indol-2-ylidene)-1,2-dihydro- in sulfuric 1-Amino-4-bromo-9,10-dioxo-9,10-dihydroanthracene-2-sulfonic acid in two (FIAT 764 and 1313); (b) 3H-indol-3-one,2-(1,3-dihydro-3-oxo-2H-indol-2-ylidene)-1,2-dihydro- in the boiling Nitrobenzene with Bromine bromination.

Properties and Applications

dark blue to navy blue. Aquamarine blue powder. Insoluble in Etanol. In concentrated sulfuric acid to blue light green, blue precipitation after dilution. Alkaline reduction leuco for yellow; Acid reduction leuco for pale yellow. The product of the cotton fiber to direct the gender is tall, good levelness. Used for cotton fabric direct printing, resist printing, prevent discharge and coloring discharge. Also can be used for silk and wool dyeing of wool directness high, good levelness. Standard Ironing Fastness Chlorine bleach Light Fastness Mercerized Oxygen bleach Soaping Fading Stain ISO 3-4 2-3 4-5 1 3-4 AATCC 5 1 4-5 3 3-4

Standard

Ironing Fastness

Fading

Stain

ISO

3-4

AATCC

5

Check Digit Verification of cas no

The CAS Registry Mumber 84-40-2 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 4 respectively; the second part has 2 digits, 4 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 84-40:
(4*8)+(3*4)+(2*4)+(1*0)=52
52 % 10 = 2
So 84-40-2 is a valid CAS Registry Number.

84-40-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name (2E)-5-bromo-2-(5-bromo-3-oxo-1H-indol-2-ylidene)-1H-indol-3-one

1.2 Other means of identification

Product number -
Other names 5,5'-dibromoindigo

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:84-40-2 SDS

84-40-2Synthetic route

5-bromo-3-indoxyl acetate
17357-14-1

5-bromo-3-indoxyl acetate

5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione
84-40-2

5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione

nitromethane
75-52-5

nitromethane

5-bromo-2-nitrobenzaldehyde
20357-20-4

5-bromo-2-nitrobenzaldehyde

5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione
84-40-2

5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione

Conditions
ConditionsYield
Stage #1: nitromethane; 5-bromo-2-nitrobenzaldehyde With sodium methylate In methanol
Stage #2: With sodium sulfate; sodium hydroxide In water
56%
5-bromo-2-<(carboxymethyl)amino>-benzoic acid
32253-75-1

5-bromo-2-<(carboxymethyl)amino>-benzoic acid

5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione
84-40-2

5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione

Conditions
ConditionsYield
With sodium acetate; acetic anhydride Verseifen des Reaktionsprodukts und nachfolgende Oxydation mit Luft;
1-(2-amino-5-bromophenyl)ethanone
29124-56-9

1-(2-amino-5-bromophenyl)ethanone

5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione
84-40-2

5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione

Conditions
ConditionsYield
With quinoline; sulfur
1-(2-amino-5-bromo-phenyl)-2,2-dibromo-ethanone

1-(2-amino-5-bromo-phenyl)-2,2-dibromo-ethanone

5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione
84-40-2

5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione

Conditions
ConditionsYield
With sodium hydroxide Schuetteln der erhaltenen Loesung mit Luft;
2-(ethoxycarbonylmethyl-nitroso-amino)-5-bromo-benzoic acid ethyl ester

2-(ethoxycarbonylmethyl-nitroso-amino)-5-bromo-benzoic acid ethyl ester

5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione
84-40-2

5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione

Conditions
ConditionsYield
With potassium hydroxide Behandeln des Reaktionsprodukts im Wasser mit Luft;
5-bromo-2-nitrobenzaldehyde
20357-20-4

5-bromo-2-nitrobenzaldehyde

acetone
67-64-1

acetone

5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione
84-40-2

5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione

Conditions
ConditionsYield
With sodium hydroxide
With sodium hydroxide
With sodium hydroxide In water
1H,1H'-2,2'-Biindolylidene-3,3'-dione
482-89-3

1H,1H'-2,2'-Biindolylidene-3,3'-dione

5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione
84-40-2

5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione

Conditions
ConditionsYield
With bromine
5.5'-dibromo-dehydroindigo diacetate

5.5'-dibromo-dehydroindigo diacetate

5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione
84-40-2

5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione

Conditions
ConditionsYield
durch Reduktion;
5-bromo-isatin chloride

5-bromo-isatin chloride

5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione
84-40-2

5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione

Conditions
ConditionsYield
With hydrogen iodide; sulphurous acid; acetic acid
<5-bromo-2-nitro-α-oxy-benzyl>-acetone

<5-bromo-2-nitro-α-oxy-benzyl>-acetone

5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione
84-40-2

5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione

Conditions
ConditionsYield
With alkali
1H,1H'-2,2'-Biindolylidene-3,3'-dione
482-89-3

1H,1H'-2,2'-Biindolylidene-3,3'-dione

bromo-starch

bromo-starch

5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione
84-40-2

5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione

compound of 5-bromo-2-nitro-phenyllactic acid aldehyde with acetaldehyde

compound of 5-bromo-2-nitro-phenyllactic acid aldehyde with acetaldehyde

5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione
84-40-2

5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione

Conditions
ConditionsYield
With alkali
5.5'-dibromo-3.3'-dioxo-diindolinyl-(2.2')-disulfonic acid-(2.2')(?)

5.5'-dibromo-3.3'-dioxo-diindolinyl-(2.2')-disulfonic acid-(2.2')(?)

A

5-Bromo-1H-indole-2,3-dione
87-48-9

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

B

5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione
84-40-2

5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione

Conditions
ConditionsYield
With hydrogenchloride
N-(4-bromo-2-(2,2-dibromoacetyl)phenyl)acetamide
85976-21-2

N-(4-bromo-2-(2,2-dibromoacetyl)phenyl)acetamide

5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione
84-40-2

5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: alcohol; water; hydrobromic acid / man faellt mit Wasser
2: diluted NaOH-solution / Schuetteln der erhaltenen Loesung mit Luft
View Scheme
5-bromo-1H-indole

5-bromo-1H-indole

5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione
84-40-2

5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione

N,N’-di-Boc-5,5’-dibromoindigo

N,N’-di-Boc-5,5’-dibromoindigo

5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione
84-40-2

5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione

Conditions
ConditionsYield
UV-irradiation;
3-iodo-5-bromo-1H-indole

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

5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione
84-40-2

5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: acetic acid / 1 h / 90 °C
2: sodium hydroxide / water; ethanol / 2 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: acetic acid / 1 h / 90 °C
2: sodium hydroxide / ethanol / 2 h / 20 °C
View Scheme
5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione
84-40-2

5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione

5-Bromo-2-aminobenzoic acid
5794-88-7

5-Bromo-2-aminobenzoic acid

Conditions
ConditionsYield
Stage #1: 5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione With bromamine B; sodium hydroxide; palladium dichloride In water; acetonitrile at 60℃; for 3.66667h; pH=12;
Stage #2: In water Acidic conditions;
95%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione
84-40-2

5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione

N,N’-di-Boc-5,5’-dibromoindigo

N,N’-di-Boc-5,5’-dibromoindigo

Conditions
ConditionsYield
With dmap; triethylamine In tetrahydrofuran at 20℃;94%
With dmap at 20℃; for 72h; Darkness;45.6%
sulfuric acid
7664-93-9

sulfuric acid

bromine
7726-95-6

bromine

5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione
84-40-2

5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione

4.5.7.4'.5'.7'-hexabromo-indigo perbromide

4.5.7.4'.5'.7'-hexabromo-indigo perbromide

bromine
7726-95-6

bromine

iodine
7553-56-2

iodine

5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione
84-40-2

5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione

4.5.7.4'.5'.7'-hexabromo-indigo perbromide

4.5.7.4'.5'.7'-hexabromo-indigo perbromide

bromine
7726-95-6

bromine

5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione
84-40-2

5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione

4.5.7.5'.7'-pentabromo-indigo perbromide

4.5.7.5'.7'-pentabromo-indigo perbromide

Conditions
ConditionsYield
at 100 - 120℃;
chlorosulfonic acid
7790-94-5

chlorosulfonic acid

bromine
7726-95-6

bromine

5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione
84-40-2

5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione

4.5.7.5'.7'-pentabromo-indigo perbromide

4.5.7.5'.7'-pentabromo-indigo perbromide

4.5.7.5'.7'-pentabromo-indigo perbromide

4.5.7.5'.7'-pentabromo-indigo perbromide

acetic acid
64-19-7

acetic acid

5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione
84-40-2

5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione

permanganate

permanganate

5.5'-dibromo-2.2'-diacetoxy-3.3'-dioxo-diindolinyl-(2.2')

5.5'-dibromo-2.2'-diacetoxy-3.3'-dioxo-diindolinyl-(2.2')

sulfuric acid
7664-93-9

sulfuric acid

nitric acid
7697-37-2

nitric acid

5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione
84-40-2

5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione

5.5'-dibromo-7.7'-dinitro-indigo

5.5'-dibromo-7.7'-dinitro-indigo

sulfite(2-)
14265-45-3

sulfite(2-)

5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione
84-40-2

5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione

lead electrodes

lead electrodes

5.5'-dibromo-leuco indigo

5.5'-dibromo-leuco indigo

Conditions
ConditionsYield
at 70℃; Electrolysis;
bromine
7726-95-6

bromine

5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione
84-40-2

5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione

5.7.5'.7'-tetrabromo-indigo dibromide

5.7.5'.7'-tetrabromo-indigo dibromide

Conditions
ConditionsYield
at 40 - 60℃;
sulfuric acid
7664-93-9

sulfuric acid

bromine
7726-95-6

bromine

5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione
84-40-2

5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione

5.7.5'.7'-tetrabromo-indigo dibromide

5.7.5'.7'-tetrabromo-indigo dibromide

Conditions
ConditionsYield
at 45℃;
5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione
84-40-2

5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione

potassium permanganate

potassium permanganate

dibromo-anhydro-isatin-α-anthranilide

dibromo-anhydro-isatin-α-anthranilide

chlorine
7782-50-5

chlorine

acetic acid
64-19-7

acetic acid

5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione
84-40-2

5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione

A

monochloro-5.5'-dibromo-dihydroindigo

monochloro-5.5'-dibromo-dihydroindigo

B

dichloro-5.5'-dibromo-dehydroindigo

dichloro-5.5'-dibromo-dehydroindigo

sulfuryl dichloride
7791-25-5

sulfuryl dichloride

chlorine
7782-50-5

chlorine

5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione
84-40-2

5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione

monochlorodibromoindigo

monochlorodibromoindigo

84-40-2Relevant articles and documents

High-Performance Ambipolar Polymers Based on Electron-Withdrawing Group Substituted Bay-Annulated Indigo

Yang, Jie,Jiang, Yaqian,Tu, Zeyi,Zhao, Zhiyuan,Chen, Jinyang,Yi, Zhengran,Li, Yifan,Wang, Shuai,Yi, Yuanping,Guo, Yunlong,Liu, Yunqi

, (2019/01/05)

For donor–acceptor conjugated polymers, it is an effective strategy to improve their electron mobilities by introducing electron-withdrawing groups (EWGs, such as F, Cl, or CF3) into the polymer backbone. However, the introduction of different EWGs always requires a different synthetic approach, leading to additional arduous work. Here, an effective two-step method is developed to obtain EWG substituted bay-annulated indigo (BAI) units. This method is effective to introduce various EWGs (F, Cl, or CF3) into BAI at different substituted positions. Based on this method, EWG substituted BAI acceptors, including 2FBAI, 2ClBAI, and 2CF3BAI, are reported for the first time. Furthermore, four polymers of PBAI-V, P2FBAI-V, P2ClBAI-V, and P4OBAI-V are developed. All the polymers show ambipolar transport properties. Particularly, P2ClBAI-V exhibits remarkable hole and electron mobilities of 4.04 and 1.46 cm2 V?1 s?1, respectively. These mobilities are among the highest values for BAI-based polymers.

Design of indigo derivatives as environment-friendly organic semiconductors for sustainable organic electronics

Klimovich,Leshanskaya,Troyanov,Anokhin,Novikov,Piryazev,Ivanov,Dremova,Troshin

, p. 7621 - 7631 (2014/12/10)

We report the synthesis and systematic investigation of nine different indigo derivatives as promising materials for sustainable organic electronics. It has been shown that chemical design allows one to tune optoelectronic properties of indigoids as well

High performance ambipolar organic field-effect transistors based on indigo derivatives

Pitayatanakul, Oratai,Higashino, Toshiki,Kadoya, Tomofumi,Tanaka, Masaki,Kojima, Hirotaka,Ashizawa, Minoru,Kawamoto, Tadashi,Matsumoto, Hidetoshi,Ishikawa, Ken,Mori, Takehiko

, p. 9311 - 9317 (2015/01/09)

A bio-inspired organic semiconductor 5,5′-diphenylindigo shows excellent and well-balanced ambipolar transistor properties; its hole and electron mobilities are 0.56 and 0.95 cm2 V-1 s-1, respectively. The enhanced performance is attributed to the extended π-π overlap of the phenyl groups as well as the characteristic packing pattern that is a hybrid of the herringbone and brickwork structures. The ambipolar transistor characteristics are analyzed considering its operating regions, where a large unipolar saturated region appears due to the difference of the electron and hole threshold voltages.

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