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54827-17-7

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54827-17-7 Usage

Description

Tetramethylbenzidine(TMB) is a chromogenic substrate used in staining procedures in immunohistochemistry as well as being a visualising reagent used in enzyme-linked immunosorbent assays (ELISA). It is a white solid that forms a pale blue-green liquid in solution with ethyl acetate. Tetramethylbenzidine is degraded by sunlight and by fluorescent lights. It?is a soluble chromogen substrate for horseradish peroxidase detection systems. Tetramethylbenzidine is recommended for ELISA procedures.

Chemical Properties

Different sources of media describe the Chemical Properties of 54827-17-7 differently. You can refer to the following data:
1. Tetramethylbenzidine is sensitive to prolonged exposure to light. Neutralizes acids in exothermic reactions to form salts plus water.Tetramethylbenzidine may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.
2. White or light yellow solid, odorless, tasteless, insoluble in water, easily soluble in acetone, ether, dimethyl sulfoxide, dimethylformamide and other organic solvents.

Reactions

TMB can act as a hydrogen donor for the reduction of hydrogen peroxide to water by peroxidase enzymes such as horseradish peroxidase. Oxidation of TMB Shows the oxidation of 3,3′,5,5′-tetramethylbenzidine (TMB) to 3,3',5,5'-tetramethylbenzidine diimine The resulting diimine causes the solution to take on a blue colour, and this colour change can be read on a spectrophotometer at the wavelengths of 370 and 650 nm.

Carcinogenicity

It is not known if Tetramethylbenzidine is carcinogenic and the evidence is contradictory: Tetramethylbenzidine is not mutagenic by the Ames test, and did not induce formation of tumors in a single-arm study of 24 rats. On that evidence, it has been used as a replacement for carcinogenic compounds such as benzidine and o-phenylenediamine.

storage

Keep as concentrated solution, aliquot and store at 4oC. Do not freeze.

Uses

Different sources of media describe the Uses of 54827-17-7 differently. You can refer to the following data:
1. 3,3,5,5-Tetramethyl benzidine is used as a reagent in a sensitive staining procedure for the detection of low levels of heme-associated peroxidase activity of cytochrome P-450 on SDS-polyacrylamide or agarose gel; non-carcinogenic substitute for benzidine as reagent for the detection of blood and determination of hemoglobin content.
2. 3,3′,5,5′-Tetramethylbenzidine may be used as a substrate for the analysis of diclofenac in water samples and dextromethorphan and its major metabolite dextrorphan in urine samples using enzyme-linked immunosorbent assay (ELISA) and gas chromatography coupled to mass spectrometry (GC-MS).

Application

3,3′,5,5′-Tetramethylbenzidine (TMB) is a chromogenic substrate used in staining procedures in immunohistochemistry as well as being a visualising reagent used in enzyme-linked immunosorbent assays (ELISA). The substrate produces a soluble end product that is pale blue in color and can be read spectrophotometrically at 370 or 620-650 nm. The TMB reaction may be stopped with 2 M H2SO4 (resulting in a yellow color), and read at 450 nm. A sensitive and specific reagent for the detection of blood, assay of hemoglobin, assay of peroxidases.

Preparation

Synthesis of 3,3',5,5'-Tetramethylbenzidine: Using 2,6-dimethylaniline as raw material, through activation, oxidative coupling and purification, pure 3,3,5,5-tetramethylbenzidine was obtained Methylbenzidine, the total yield is 65%.

General Description

3,3',5,5'-tetramethylbenzidine appears as pale yellow crystals or off-white powder. (NTP, 1992)

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Tetramethylbenzidine is sensitive to prolonged exposure to light . Neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.

Fire Hazard

Flash point data for Tetramethylbenzidine are not available, however, Tetramethylbenzidine is probably combustible.

Biochem/physiol Actions

3,3′,5,5′-Tetramethylbenzidine/TMB can be used as a chromogen to increase the progression of product obtained in peroxidase reaction. In food and environmental decontamination procedures, TMB can be used in in?situ free available chlorine (FAC) monitoring of chlorite-based sanitizers.

Check Digit Verification of cas no

The CAS Registry Mumber 54827-17-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,4,8,2 and 7 respectively; the second part has 2 digits, 1 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 54827-17:
(7*5)+(6*4)+(5*8)+(4*2)+(3*7)+(2*1)+(1*7)=137
137 % 10 = 7
So 54827-17-7 is a valid CAS Registry Number.

54827-17-7 Well-known Company Product Price

  • Brand
  • (Code)Product description
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  • Detail
  • TCI America

  • (T2573)  3,3',5,5'-Tetramethylbenzidine [for Biochemical Research]  >98.0%(HPLC)(T)

  • 54827-17-7

  • 1g

  • 570.00CNY

  • Detail
  • TCI America

  • (T2573)  3,3',5,5'-Tetramethylbenzidine [for Biochemical Research]  >98.0%(HPLC)(T)

  • 54827-17-7

  • 5g

  • 1,490.00CNY

  • Detail
  • TCI America

  • (T1023)  3,3',5,5'-Tetramethylbenzidine  >98.0%(HPLC)(T)

  • 54827-17-7

  • 1g

  • 108.00CNY

  • Detail
  • TCI America

  • (T1023)  3,3',5,5'-Tetramethylbenzidine  >98.0%(HPLC)(T)

  • 54827-17-7

  • 5g

  • 380.00CNY

  • Detail
  • TCI America

  • (T1023)  3,3',5,5'-Tetramethylbenzidine  >98.0%(HPLC)(T)

  • 54827-17-7

  • 25g

  • 1,400.00CNY

  • Detail
  • Alfa Aesar

  • (A13868)  3,3',5,5'-Tetramethylbenzidine, 98%   

  • 54827-17-7

  • 1g

  • 377.0CNY

  • Detail
  • Alfa Aesar

  • (A13868)  3,3',5,5'-Tetramethylbenzidine, 98%   

  • 54827-17-7

  • 5g

  • 1389.0CNY

  • Detail
  • Alfa Aesar

  • (A13868)  3,3',5,5'-Tetramethylbenzidine, 98%   

  • 54827-17-7

  • 25g

  • 5102.0CNY

  • Detail
  • Sigma

  • (87748)  3,3′,5,5′-Tetramethylbenzidine  ≥98.0% (NT)

  • 54827-17-7

  • 87748-1G

  • 476.19CNY

  • Detail
  • Sigma

  • (87748)  3,3′,5,5′-Tetramethylbenzidine  ≥98.0% (NT)

  • 54827-17-7

  • 87748-5G

  • 1,547.91CNY

  • Detail
  • Sigma

  • (87748)  3,3′,5,5′-Tetramethylbenzidine  ≥98.0% (NT)

  • 54827-17-7

  • 87748-25G

  • 5,440.50CNY

  • Detail

54827-17-7SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Tetramethylbenzidine

1.2 Other means of identification

Product number -
Other names 3355TMB

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:54827-17-7 SDS

54827-17-7Synthetic route

1,2-Bis(2,4-dimethylphenyl)diazene
29418-31-3

1,2-Bis(2,4-dimethylphenyl)diazene

3,3',5,5'-tetramethylbenzidine
54827-17-7

3,3',5,5'-tetramethylbenzidine

Conditions
ConditionsYield
With hydrogenchloride; zinc In water; ethyl acetate at 20℃; Benzidine Rearrangement;96%
With ammonium chloride; zinc In methanol; water at 20℃; for 6h; Reflux;85 g
4-chloro-2,6-dimethylaniline
24596-18-7

4-chloro-2,6-dimethylaniline

3,3',5,5'-tetramethylbenzidine
54827-17-7

3,3',5,5'-tetramethylbenzidine

Conditions
ConditionsYield
With carbon dioxide; aluminium; 1-butyl-3-methylimidazolium trifluoromethanesulfonimide at 45℃; under 116262 Torr; for 10h; Ullmann reaction;93%
With 4-(3'-butyl-1'-imidazolio)-1-butanesulfonic acid hydrogen sulfate; aluminium In carbon dioxide at 45℃; under 116262 Torr; for 10h; Ullmann reaction; Supercritical conditions;91%
3,3’,5,5’-tetramethylbenzidine dihydrochloride

3,3’,5,5’-tetramethylbenzidine dihydrochloride

3,3',5,5'-tetramethylbenzidine
54827-17-7

3,3',5,5'-tetramethylbenzidine

Conditions
ConditionsYield
With sodium hydroxide In methanol at 50℃; for 1h; Inert atmosphere;72.4%
2-methylindole-3-carboxaldehyde 2,6-dimethylphenylhydrazone
80387-68-4

2-methylindole-3-carboxaldehyde 2,6-dimethylphenylhydrazone

A

3,3',5,5'-tetramethylbenzidine
54827-17-7

3,3',5,5'-tetramethylbenzidine

B

3-(4-amino-3,5-dimethylphenyl)-2-methylindole
80387-72-0

3-(4-amino-3,5-dimethylphenyl)-2-methylindole

C

2,6-dimethylaniline
87-62-7

2,6-dimethylaniline

Conditions
ConditionsYield
With PPA; Polyphosphoric acid (PPA) at 100℃; for 0.5h;A 1.85 g
B 2.53 g
C 0.77 g
(2,6-dimethylphenyl)hydrazine
603-77-0

(2,6-dimethylphenyl)hydrazine

3,3',5,5'-tetramethylbenzidine
54827-17-7

3,3',5,5'-tetramethylbenzidine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 51 percent / traces of AcOH / 0.75 h / 140 - 150 °C
2: 1.85 g / polyphosphoric acid (PPA) / 0.5 h / 100 °C
View Scheme
4-bromo-2,6-dimethylphenylamine
24596-19-8

4-bromo-2,6-dimethylphenylamine

A

3,3',5,5'-tetramethylbenzidine
54827-17-7

3,3',5,5'-tetramethylbenzidine

B

2,6-dimethylaniline
87-62-7

2,6-dimethylaniline

Conditions
ConditionsYield
With sodium formate; cetyltrimethylammonim bromide; palladium on charcoal In waterA 7.7 parts (63.3%)
B n/a
3,3',5,5'-tetramethylbenzidine diimine

3,3',5,5'-tetramethylbenzidine diimine

3,3',5,5'-tetramethylbenzidine
54827-17-7

3,3',5,5'-tetramethylbenzidine

Conditions
ConditionsYield
With uric Acid In aq. acetate buffer at 30℃; for 0.416667h; pH=4.4;
2,6-dimethylaniline
87-62-7

2,6-dimethylaniline

3,3',5,5'-tetramethylbenzidine
54827-17-7

3,3',5,5'-tetramethylbenzidine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N-Bromosuccinimide / N,N-dimethyl-formamide / 2 h / 0 - 20 °C
2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate / 1,4-dioxane / 16 h / 75 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1: N-Bromosuccinimide / N,N-dimethyl-formamide / 2 h / 0 - 20 °C
2: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 15 h / 80 °C / Inert atmosphere
3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate / 1,4-dioxane / 16 h / 75 °C / Inert atmosphere
View Scheme
Multi-step reaction with 5 steps
1: sodium tungstate (VI) dihydrate; dihydrogen peroxide / diethyl ether; water / 9 h / 20 - 30 °C
2: sodium thiosulfate; sodium hydrogen sulfide / methanol / 2.5 h / 20 - 75 °C
3: sulfuric acid / chlorobenzene / 3 h / 20 - 40 °C
4: hydrazine hydrate; hydrogenchloride; pyrographite / water / 2.5 h / 100 °C
5: sodium hydroxide / methanol / 1 h / 50 °C / Inert atmosphere
View Scheme
4-bromo-2,6-dimethylphenylamine
24596-19-8

4-bromo-2,6-dimethylphenylamine

3,3',5,5'-tetramethylbenzidine
54827-17-7

3,3',5,5'-tetramethylbenzidine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 15 h / 80 °C / Inert atmosphere
2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate / 1,4-dioxane / 16 h / 75 °C / Inert atmosphere
View Scheme
2,6-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline
1004761-68-5

2,6-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

4-bromo-2,6-dimethylphenylamine
24596-19-8

4-bromo-2,6-dimethylphenylamine

3,3',5,5'-tetramethylbenzidine
54827-17-7

3,3',5,5'-tetramethylbenzidine

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In 1,4-dioxane at 75℃; for 16h; Inert atmosphere;210 g
2,2′,6,6′-tetramethylazobenzene-N,N'-dioxide

2,2′,6,6′-tetramethylazobenzene-N,N'-dioxide

3,3',5,5'-tetramethylbenzidine
54827-17-7

3,3',5,5'-tetramethylbenzidine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: sodium thiosulfate; sodium hydrogen sulfide / methanol / 2.5 h / 20 - 75 °C
2: sulfuric acid / chlorobenzene / 3 h / 20 - 40 °C
3: hydrazine hydrate; hydrogenchloride; pyrographite / water / 2.5 h / 100 °C
4: sodium hydroxide / methanol / 1 h / 50 °C / Inert atmosphere
View Scheme
2,2′,6,6′-(tetramethyldiphenyl)hydrazine
63615-06-5

2,2′,6,6′-(tetramethyldiphenyl)hydrazine

3,3',5,5'-tetramethylbenzidine
54827-17-7

3,3',5,5'-tetramethylbenzidine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sulfuric acid / chlorobenzene / 3 h / 20 - 40 °C
2: hydrazine hydrate; hydrogenchloride; pyrographite / water / 2.5 h / 100 °C
3: sodium hydroxide / methanol / 1 h / 50 °C / Inert atmosphere
View Scheme
C30H28N2O2

C30H28N2O2

3,3',5,5'-tetramethylbenzidine
54827-17-7

3,3',5,5'-tetramethylbenzidine

Conditions
ConditionsYield
With water In N,N-dimethyl-formamide pH=1.8;
C30H28N2

C30H28N2

3,3',5,5'-tetramethylbenzidine
54827-17-7

3,3',5,5'-tetramethylbenzidine

Conditions
ConditionsYield
With water In N,N-dimethyl-formamide pH=1.8;
oxo-(2,4,6-trimethylphenylamino)acetyl chloride
868961-34-6

oxo-(2,4,6-trimethylphenylamino)acetyl chloride

3,3',5,5'-tetramethylbenzidine
54827-17-7

3,3',5,5'-tetramethylbenzidine

C38H42N4O4
1071505-64-0

C38H42N4O4

Conditions
ConditionsYield
In tetrahydrofuran96%
3,3',5,5'-tetramethylbenzidine
54827-17-7

3,3',5,5'-tetramethylbenzidine

5-dodecyloxy-2-hydroxyterephthaldehyde
376368-24-0

5-dodecyloxy-2-hydroxyterephthaldehyde

polymer; monomers: 5-dodecyloxy-2-hydroxyterephthaldehyde; 3,3\,,5,5\-tetramethylbenzidine

polymer; monomers: 5-dodecyloxy-2-hydroxyterephthaldehyde; 3,3\,,5,5\-tetramethylbenzidine

Conditions
ConditionsYield
With lithium chloride In 1-methyl-pyrrolidin-2-one; N,N,N,N,N,N-hexamethylphosphoric triamide at 20℃; for 24h;92%
phosgene
75-44-5

phosgene

3,3',5,5'-tetramethylbenzidine
54827-17-7

3,3',5,5'-tetramethylbenzidine

3,3',5,5'-tetramethylbiphenyl-4,4'-diisocyanate

3,3',5,5'-tetramethylbiphenyl-4,4'-diisocyanate

Conditions
ConditionsYield
In various solvent(s) for 0.5h; Condensation; Heating;90%
3,3',5,5'-tetramethylbenzidine
54827-17-7

3,3',5,5'-tetramethylbenzidine

1,1'-Thiocarbonyldi-2(1H)-pyridone
102368-13-8

1,1'-Thiocarbonyldi-2(1H)-pyridone

4,4'-diisothiocyanato-3,5,3',5'-tetramethyl-biphenyl

4,4'-diisothiocyanato-3,5,3',5'-tetramethyl-biphenyl

Conditions
ConditionsYield
In dichloromethane at 20℃; Substitution;88%
2-isothiocyanato-6-methylpyridine

2-isothiocyanato-6-methylpyridine

3,3',5,5'-tetramethylbenzidine
54827-17-7

3,3',5,5'-tetramethylbenzidine

1,1'-(3,3',5,5'-tetramethyl-[1,1'-biphenyl]-4,4'-diyl)bis(3-(6-methylpyridin-2-yl)thiourea)

1,1'-(3,3',5,5'-tetramethyl-[1,1'-biphenyl]-4,4'-diyl)bis(3-(6-methylpyridin-2-yl)thiourea)

Conditions
ConditionsYield
In methanol at 20℃;85%
3,3',5,5'-tetramethylbenzidine
54827-17-7

3,3',5,5'-tetramethylbenzidine

Conditions
ConditionsYield
With hydrogenchloride In water; ethyl acetate for 0.5h; Solvent;85%
3,3',5,5'-tetramethylbenzidine
54827-17-7

3,3',5,5'-tetramethylbenzidine

3,3',5,5'-tetramethylbenzidinochinon-diimoniumperchlorat

3,3',5,5'-tetramethylbenzidinochinon-diimoniumperchlorat

Conditions
ConditionsYield
With potassium dichromate; perchloric acid; acetic acid In water84.3%
3,3',5,5'-tetramethylbenzidine
54827-17-7

3,3',5,5'-tetramethylbenzidine

3,3',5,5'-tetramethylbenzidine-d16

3,3',5,5'-tetramethylbenzidine-d16

Conditions
ConditionsYield
With water-d2; platinum on carbon at 180℃; for 24h; Product distribution / selectivity;82%
With hydrogen; water-d2; palladium on activated charcoal; 10% palladium on active carbon; platinum on carbon In water-d2 at 180℃; for 24h;54%
With water-d2; platinum on carbon; palladium 10% on activated carbon at 180℃; for 24h; Product distribution / selectivity;54%
With hydrogen; water-d2; palladium on activated charcoal; platinum on activated charcoal at 180℃; for 24h;
3,3',5,5'-tetramethylbenzidine
54827-17-7

3,3',5,5'-tetramethylbenzidine

(1R,3R,8R,10R)-2,2,9,9-tetramethyl-3,4,7,8,9,10-hexahydro-1H-1,3:8,10-dimethanocyclopenta[1,2-b:5,4-b']diquinolin-12(2H)-one

(1R,3R,8R,10R)-2,2,9,9-tetramethyl-3,4,7,8,9,10-hexahydro-1H-1,3:8,10-dimethanocyclopenta[1,2-b:5,4-b']diquinolin-12(2H)-one

3,3',5,5'-tetramethyl-N4,N4'-bis((1R,3R,8R,10R)-2,2,9,9-tetramethyl-3,4,7,8,9,10-hexahydro-1H-1,3:8,10-dimethanocyclopenta[1,2-b:5,4-b']diquinolin-12(2H)-ylidene)-[1,1'-biphenyl]-4,4'-diamine

3,3',5,5'-tetramethyl-N4,N4'-bis((1R,3R,8R,10R)-2,2,9,9-tetramethyl-3,4,7,8,9,10-hexahydro-1H-1,3:8,10-dimethanocyclopenta[1,2-b:5,4-b']diquinolin-12(2H)-ylidene)-[1,1'-biphenyl]-4,4'-diamine

Conditions
ConditionsYield
With pyridine; titanium tetrachloride In tetrahydrofuran at 25℃; for 48h; Reagent/catalyst; Temperature;82%
3,3',5,5'-tetramethylbenzidine
54827-17-7

3,3',5,5'-tetramethylbenzidine

4-Methoxyphenyl isothiocyanate
2284-20-0

4-Methoxyphenyl isothiocyanate

1,1'-(3,3',5,5'-tetramethyl-[1,1'-biphenyl]-4,4'-diyl)bis(3-(4-methoxyphenyl)thiourea)

1,1'-(3,3',5,5'-tetramethyl-[1,1'-biphenyl]-4,4'-diyl)bis(3-(4-methoxyphenyl)thiourea)

Conditions
ConditionsYield
In methanol at 20℃;78%
tetrakis(dimethylamido)titanium(IV)

tetrakis(dimethylamido)titanium(IV)

chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

3,3',5,5'-tetramethylbenzidine
54827-17-7

3,3',5,5'-tetramethylbenzidine

[(Me2NH)2TiCl2(3,3',5,5'-tetramethyl-1,1'-biphenyl-4,4'-diimido)TiCl2(NHMe2)]
950993-23-4

[(Me2NH)2TiCl2(3,3',5,5'-tetramethyl-1,1'-biphenyl-4,4'-diimido)TiCl2(NHMe2)]

Conditions
ConditionsYield
In toluene under Ar, Schlenk techniques; diamine added to soln. of Ti compd. in toluene at room temp. (molar ratio = 1:1), about 8 equiv. of Me3SiCl added at room temp., mixt. stirred at room temp. overnight; crystd. (without or on addn. of pentane) or evapn. of soln., solid washed with pentane, dried under vac., recrystd. from toluene/pentane; elem. anal.;77%
(3,4,5-trimethoxyphenyl)isothiocyanate
35967-24-9

(3,4,5-trimethoxyphenyl)isothiocyanate

3,3',5,5'-tetramethylbenzidine
54827-17-7

3,3',5,5'-tetramethylbenzidine

1,1'-(3,3',5,5'-tetramethyl-[1,1'-biphenyl]-4,4'-diyl)bis(3-(3,4,5-trimethoxyphenyl)thiourea)

1,1'-(3,3',5,5'-tetramethyl-[1,1'-biphenyl]-4,4'-diyl)bis(3-(3,4,5-trimethoxyphenyl)thiourea)

Conditions
ConditionsYield
In methanol at 20℃;75%
3,3',5,5'-tetramethylbenzidine
54827-17-7

3,3',5,5'-tetramethylbenzidine

p-butylphenyl isothiocyanate
23165-44-8

p-butylphenyl isothiocyanate

1,1'-(3,3',5,5'-tetramethyl-[1,1'-biphenyl]-4,4'-diyl)bis(3-(4-butylphenyl)thiourea)

1,1'-(3,3',5,5'-tetramethyl-[1,1'-biphenyl]-4,4'-diyl)bis(3-(4-butylphenyl)thiourea)

Conditions
ConditionsYield
In methanol at 20℃;75%
3,3',5,5'-tetramethylbenzidine
54827-17-7

3,3',5,5'-tetramethylbenzidine

4-Chlorophenyl isothiocyanate
2131-55-7

4-Chlorophenyl isothiocyanate

1,1'-(3,3',5,5'-tetramethyl-[1,1'-biphenyl]-4,4'-diyl)bis(3-(4-chlorophenyl)thiourea)

1,1'-(3,3',5,5'-tetramethyl-[1,1'-biphenyl]-4,4'-diyl)bis(3-(4-chlorophenyl)thiourea)

Conditions
ConditionsYield
In methanol at 20℃;75%
2,3-dihydroxybenzaldehyde
24677-78-9

2,3-dihydroxybenzaldehyde

3,3',5,5'-tetramethylbenzidine
54827-17-7

3,3',5,5'-tetramethylbenzidine

C30H28N2O4

C30H28N2O4

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene Heating;72%
3,3',5,5'-tetramethylbenzidine
54827-17-7

3,3',5,5'-tetramethylbenzidine

salicylaldehyde
90-02-8

salicylaldehyde

C30H28N2O2

C30H28N2O2

Conditions
ConditionsYield
In methanol at 70℃; for 3h; Inert atmosphere;70%
3,3',5,5'-tetramethylbenzidine
54827-17-7

3,3',5,5'-tetramethylbenzidine

benzaldehyde
100-52-7

benzaldehyde

C30H28N2

C30H28N2

Conditions
ConditionsYield
In methanol at 70℃; for 3h; Inert atmosphere;70%
3,3',5,5'-tetramethylbenzidine
54827-17-7

3,3',5,5'-tetramethylbenzidine

1-isothiocyanatonaphthalene
551-06-4

1-isothiocyanatonaphthalene

1,1'-(3,3',5,5'-tetramethyl-[1,1'-biphenyl]-4,4'-diyl)bis(3-(naphthalen-1-yl)thiourea)

1,1'-(3,3',5,5'-tetramethyl-[1,1'-biphenyl]-4,4'-diyl)bis(3-(naphthalen-1-yl)thiourea)

Conditions
ConditionsYield
In methanol at 20℃;70%
3,3',5,5'-tetramethylbenzidine
54827-17-7

3,3',5,5'-tetramethylbenzidine

p-nitrophenyl isothiocyanate
2131-61-5

p-nitrophenyl isothiocyanate

1,1'-(3,3',5,5'-tetramethyl-[1,1'-biphenyl]-4,4'-diyl)bis(3-(4-nitrophenyl)thiourea)

1,1'-(3,3',5,5'-tetramethyl-[1,1'-biphenyl]-4,4'-diyl)bis(3-(4-nitrophenyl)thiourea)

Conditions
ConditionsYield
In methanol at 20℃;68%
pyridine-2-carbaldehyde
1121-60-4

pyridine-2-carbaldehyde

3,3',5,5'-tetramethylbenzidine
54827-17-7

3,3',5,5'-tetramethylbenzidine

3,5,3',5'-tetramethyl-N,N-bis(pyridin-2-ylmethylene)biphenyl-4,4'-diamine

3,5,3',5'-tetramethyl-N,N-bis(pyridin-2-ylmethylene)biphenyl-4,4'-diamine

Conditions
ConditionsYield
In ethanol Heating / reflux;62%
3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

3,3',5,5'-tetramethylbenzidine
54827-17-7

3,3',5,5'-tetramethylbenzidine

(1E,1′E)-N,N′-(3,3′,5,5′-tetramethyl-[1,1′-biphenyl]-4,4′-diyl)bis(1-(pyridin-3-yl)methanimine)

(1E,1′E)-N,N′-(3,3′,5,5′-tetramethyl-[1,1′-biphenyl]-4,4′-diyl)bis(1-(pyridin-3-yl)methanimine)

Conditions
ConditionsYield
With formic acid In ethanol; dichloromethane at 20℃;62%
oxodichloro-bis-diethyldithiocarbamato molybdenum(VI)
57146-54-0

oxodichloro-bis-diethyldithiocarbamato molybdenum(VI)

3,3',5,5'-tetramethylbenzidine
54827-17-7

3,3',5,5'-tetramethylbenzidine

Conditions
ConditionsYield
In methanol (N2); stirring (25°C, 10 h); filtn., solvent removal, washing (light petroleum, Et2O);56%
anthracenylmethyl chloride
24463-19-2

anthracenylmethyl chloride

3,3',5,5'-tetramethylbenzidine
54827-17-7

3,3',5,5'-tetramethylbenzidine

3,3',5,5'-tetramethyl-N-(9-anthrylmethyl)benzidine

3,3',5,5'-tetramethyl-N-(9-anthrylmethyl)benzidine

Conditions
ConditionsYield
With triethylamine In toluene Heating;55%
2-acetyl-6-[1-((2,6-dimethylphenyl)imino)ethyl]pyridine
395656-36-7

2-acetyl-6-[1-((2,6-dimethylphenyl)imino)ethyl]pyridine

3,3',5,5'-tetramethylbenzidine
54827-17-7

3,3',5,5'-tetramethylbenzidine

N,N'-bis(1-(6-(1-(2,6-dimethylphenylimino)ethyl)pyridin-2-yl)ethylidene)-3,5,3',5'-tetramethylbenzidine
1574293-42-7

N,N'-bis(1-(6-(1-(2,6-dimethylphenylimino)ethyl)pyridin-2-yl)ethylidene)-3,5,3',5'-tetramethylbenzidine

Conditions
ConditionsYield
With p-toluene sulfinic acid In toluene for 24h; Reflux;49.3%
3,3',5,5'-tetramethylbenzidine
54827-17-7

3,3',5,5'-tetramethylbenzidine

p-dimethylaminocinnamaldehyde
6203-18-5

p-dimethylaminocinnamaldehyde

(E)-N-((E)-3-(4-(dimethylamino)phenyl)allylidene)-4-(4-((E)-((E)-3-(4-(dimethylamino)phenyl)allylidene)amino)-3,5-dimethylphenyl)-2,6-dimethylphenyl-1-amine
1193110-70-1

(E)-N-((E)-3-(4-(dimethylamino)phenyl)allylidene)-4-(4-((E)-((E)-3-(4-(dimethylamino)phenyl)allylidene)amino)-3,5-dimethylphenyl)-2,6-dimethylphenyl-1-amine

Conditions
ConditionsYield
In ethanol at 90℃; for 12h; Inert atmosphere;48%
3-(4-dimethylamino-phenyl)-propenal
20432-35-3, 6203-18-5

3-(4-dimethylamino-phenyl)-propenal

3,3',5,5'-tetramethylbenzidine
54827-17-7

3,3',5,5'-tetramethylbenzidine

(E)-N-((E)-3-(4-(dimethylamino)phenyl)allylidene)-4-(4-((E)-((E)-3-(4-(dimethylamino)phenyl)allylidene)amino)-3,5-dimethylphenyl)-2,6-dimethylphenyl-1-amine
1193110-70-1

(E)-N-((E)-3-(4-(dimethylamino)phenyl)allylidene)-4-(4-((E)-((E)-3-(4-(dimethylamino)phenyl)allylidene)amino)-3,5-dimethylphenyl)-2,6-dimethylphenyl-1-amine

Conditions
ConditionsYield
In ethanol at 90℃; for 12h; Inert atmosphere;48%
tert.-butylnitrite
540-80-7

tert.-butylnitrite

3,3',5,5'-tetramethylbenzidine
54827-17-7

3,3',5,5'-tetramethylbenzidine

4,4'-dibromo-3,3',5,5'-tetramethylbiphenyl
144653-01-0

4,4'-dibromo-3,3',5,5'-tetramethylbiphenyl

Conditions
ConditionsYield
In Bromoform; ethyl acetate43%
In Bromoform; ethyl acetate43%

54827-17-7Relevant articles and documents

Enzyme mimicking inorganic hybrid Ni@MnO2 for colorimetric detection of uric acid in serum samples

Pal, Jaya,Pal, Tarasankar

, p. 83738 - 83747 (2016)

Reliable and inexpensive detection of uric acid in the absence of any peroxide or enzyme is very challenging for the development of a new cost effective clinical method. Herein, we report an easy, cost effective and nonenzymetic method for selective detection and quantification of uric acid using 3,3′,5,5′-tetramethylbenzidine (TMB) and a Ni@MnO2 hybrid nanomaterial. The ultra-long porous core-shell Ni@MnO2 hybrid nanomaterial, obtained from a simple redox transformation reaction between a prickly nickel nanowire and KMnO4 solution, is reported for the first time. The growth mechanism is studied from time-dependent FESEM and TEM images. The hybrid nanomaterial exhibited intrinsic oxidase-like activity that helps catalytic oxidation of TMB (colourless) to a blue colored product which becomes colourless in the presence of uric acid. Moreover, this colorimetric method has been exploited for the assay of serum uric acid in real samples. Our proposed method can detect as low as 0.24 μM of uric acid with a linear range from 1 to 40 μM. Therefore, we believe that this method would be useful for the detection of uric acid in clinical laboratory.

Synthesis method of biochemical preparation TMB

-

, (2018/03/26)

The invention discloses a synthesis method of a biochemical preparation TMB. The synthesis method includes following steps: synthesizing 1,2, 2', 6, 6'-azo tetratoluidine-N, N-dioxide; synthesizing 1,2, 2', 6, 6'-tetramethyl diphenylhydrazine; synthesizing 3,TMB (1/2)H2SO4; preparing 4,TMB 2HCl; preparing TMB. The synthesis method is simple in synthesis route, cheap and easy-to-obtain in raw material, low in synthesis cost and high in yield.

Diverse applications of TMB-based sensing probes

Huang, Li,Cao, Ying-Juan,Sun, Xiang-Ying,Liu, Bin,Shen, Jiang-Shan

supporting information, p. 5667 - 5676 (2018/08/17)

Extending the research on 3,3′,5,5′-tetramethylbenzidine (TMB) and its derivatives in analytical chemistry is important, considering that TMB is widely used as an enzyme catalytic substrate. In this work, two TMB derivatives, TMBS and TMBB, were synthesized via a facile and one-step condensation reaction between the -NH2 group of TMB and the -CHO group of salicylaldehyde or benzaldehyde. Because at low pH the two Schiff base compounds can release TMB which can emit strong fluorescence, the probes could show dual-modal signal responses, fluorescence and UV-vis absorption, towards the pH. Practical applications of pH sensing in Chinese rice vinegar and lemon juice samples were successfully demonstrated. On the basis of these findings, a catalytic chromogenic reaction was developed to monitor the pH with the naked eye, too. Furthermore, considering the chemical equilibrium reaction between CO2 and H2O and that glucose oxidase (GOD) can catalyse the dehydrogenation and oxidation reaction of β-d-glucose to produce gluconic acid, both of which can result in lowering the pH values of the two Schiff base systems, highly sensitive and selective dual-modal sensing systems for detecting CO2 and β-d-glucose have also been successfully established. Therefore, the two synthesized TMB derivatives can demonstrate their robust application potential.

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