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HomeProduct name listTetramethylbenzidine

Tetramethylbenzidine

Synonym(s):TMB;3,3′,5,5′-Tetramethylbenzidine;TMB substrate;3,3?,5,5?-Tetramethylbenzidine;TMB, Insoluble

  • CAS NO.:54827-17-7
  • Empirical Formula: C16H20N2
  • Molecular Weight: 240.34
  • MDL number: MFCD00007748
  • EINECS: 259-364-6
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-19 23:02:33
Tetramethylbenzidine Structural

What is Tetramethylbenzidine?

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. TMB 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

Tetramethylbenzidine is a white or light yellow solid, odorless, tasteless, insoluble in water, easily soluble in acetone, ether, dimethyl sulfoxide, dimethylformamide and other organic solvents. It forms a pale blue-green liquid in solution with ethyl acetate. TMB is degraded by sunlight and by fluorescent lights.

The Uses of Tetramethylbenzidine

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).

The Uses of Tetramethylbenzidine

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.

What are the applications of Application

3,3′,5,5′-Tetramethylbenzidine is a sensitive reagent for the detection of hemoglobin

Preparation

The synthesis of 3,3',5,5'-Tetramethylbenzidine involved using 2,6-dimethylaniline as the raw material. The process included activation, oxidative coupling, and purification, resulting in the production of pure material. The yield of 3,3,5,5-tetramethylbenzidine was 65%.

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.

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.

Carcinogenicity

The carcinogenic potential of Tetramethylbenzidine is uncertain due to conflicting evidence. It 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.
DOI: 10.1177/26.2.24068

Properties of Tetramethylbenzidine

Melting point: 168-171 °C(lit.)
Boiling point: 100 °C
Density  1
refractive index  1.5519 (estimate)
storage temp.  2-8°C
solubility  Slightly soluble. <0.1 g/100 mL at 20°C.
form  tablet
pka 4.49±0.10(Predicted)
color  Cream
Water Solubility  Slightly soluble. <0.1 g/100 mL at 20 ºC
Sensitive  Light Sensitive
BRN  2808541
Stability: Stable, but moisture sensitive and may be light sensitive. Incompatible with water, strong oxidizing agents.
CAS DataBase Reference 54827-17-7(CAS DataBase Reference)
EPA Substance Registry System 3,3',5,5'-Tetramethylbenzidine (54827-17-7)

Safety information for Tetramethylbenzidine

Signal word Warning
Pictogram(s)
ghs
Flame
Flammables
GHS02
ghs
Exclamation Mark
Irritant
GHS07
ghs
Health Hazard
GHS08
GHS Hazard Statements H225:Flammable liquids
H302:Acute toxicity,oral
H312:Acute toxicity,dermal
H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H332:Acute toxicity,inhalation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
H370:Specific target organ toxicity, single exposure
Precautionary Statement Codes P210:Keep away from heat/sparks/open flames/hot surfaces. — No smoking.
P260:Do not breathe dust/fume/gas/mist/vapours/spray.
P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P303+P361+P353:IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304+P340:IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P405:Store locked up.

Computed Descriptors for Tetramethylbenzidine

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