CAS No.54827-17-7,Tetramethylbenzidine Suppliers,MSDS download

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Basic Information

Molecular Structure:
CAS No.:	54827-17-7
Name:	Tetramethylbenzidine
Article Data:	17
Cas Database

Formula:	C₁₆H₂₀N₂
Molecular Weight:	240.348
Synonyms:	[1,1'-Biphenyl]-4,4'-diamine, 3,3',5,5'-tetramethyl-;3,3',5,5'-Tetramethyl-4,4'-biphenyldiamine;3,3',5,5'-Tetramethylbenzidine;
EINECS:	259-364-6
Density:	1.071 g/cm³
Melting Point:	168-171 °C(lit.)
Boiling Point:	368.623 °C at 760 mmHg
Flash Point:	210.8 °C
Solubility:	<0.1 g/100 mL at 20 °C in water
Appearance:	White or light yellow solid
Hazard Symbols:	Xn, Xi
Risk Codes:	36/38-36/37/38-22
Safety:	26-36-36/37
Transport Information:	UN 2796 8/PG 2
PSA:	52.04000
LogP:	4.91400

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Synthetic route

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

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

Conditions

Conditions	Yield
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

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4-chloro-2,6-dimethylaniline

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3,3',5,5'-tetramethylbenzidine

Conditions

Conditions	Yield
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

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

Conditions

Conditions	Yield
With sodium hydroxide In methanol at 50℃; for 1h; Inert atmosphere;	72.4%

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

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

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

C: 87-62-7
2,6-dimethylaniline

Conditions

Conditions	Yield
With PPA; Polyphosphoric acid (PPA) at 100℃; for 0.5h;	A 1.85 g B 2.53 g C 0.77 g

...Expand

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(2,6-dimethylphenyl)hydrazine

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

Conditions

Conditions	Yield
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

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

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

B: 87-62-7
2,6-dimethylaniline

Conditions

Conditions	Yield
With sodium formate; cetyltrimethylammonim bromide; palladium on charcoal In water	A 7.7 parts (63.3%) B n/a

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

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

Conditions

Conditions	Yield
With uric Acid In aq. acetate buffer at 30℃; for 0.416667h; pH=4.4;

: 87-62-7
2,6-dimethylaniline

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

Conditions

Conditions	Yield
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

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

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

Conditions

Conditions	Yield
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

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

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4-bromo-2,6-dimethylphenylamine

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

Conditions

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In 1,4-dioxane at 75℃; for 16h; Inert atmosphere;	210 g

Raw Materials

24596-19-8

24596-18-7

603-77-0

Downstream Products

144653-01-0

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Consensus Reports

EPA Genetic Toxicology Program. Reported in EPA TSCA Inventory.

Specification

The 3,3',5,5'-Tetramethylbenzidine, with its cas register number 54827-17-7, is a kind of white or light yellow solid. It also can be called Tetramethylbenzidine; 3,3',5,5'-Tetramethyl-(1,1'-biphenyl)-4,4'-diamine; TMB Quick; and (1,1'-Biphenyl)-4,4'-diamine, 3,3',5,5'-tetramethyl-. Tetramethylbenzidine should be stored in shady and cool warehouse and mainly used as raw material of fine chemicals and pharmaceutical intermediate.

Physical properties about 3,3',5,5'-Tetramethylbenzidine are: (1)ACD/LogP: 2.673; (2)ACD/LogD (pH 5.5): 2.63; (3)ACD/LogD (pH 7.4): 2.67; (4)ACD/BCF (pH 5.5): 57.63; (5)ACD/BCF (pH 7.4): 63.22; (6)ACD/KOC (pH 5.5): 617.03; (7)ACD/KOC (pH 7.4): 676.88; (8)#H bond acceptors: 2; (9)#H bond donors: 4; (10)#Freely Rotating Bonds: 3; (11)Index of Refraction: 1.618; (12)Molar Refractivity: 78.617 cm³; (13)Molar Volume: 224.379 cm³; (14)Polarizability: 31.166 10-24cm³; (15)Surface Tension: 45.5379981994629 dyne/cm; (16)Density: 1.071 g/cm³; (17)Flash Point: 210.807 °C; (18)Enthalpy of Vaporization: 61.53 kJ/mol; (19)Boiling Point: 368.623 °C at 760 mmHg; (20)Vapour Pressure: 0 mmHg at 25°C

When you are using this chemical, please be cautious about it as the following:
1. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice;
2. Wear suitable protective clothing;
3. Wear suitable protective clothing and gloves;

You can still convert the following datas into molecular structure:
(1)InChI=1S/C16H20N2/c1-9-5-13(6-10(2)15(9)17)14-7-11(3)16(18)12(4)8-14/h5-8H,17-18H2,1-4H3;
(2)InChIKey=UAIUNKRWKOVEES-UHFFFAOYSA-N;
(3)Smilesc1(c(cc(c2cc(c(N)c(c2)C)C)cc1C)C)N;

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intraperitoneal	135mg/kg (135mg/kg)		Progress in Mutation Research. Vol. 1, Pg. 682, 1981.
quail	LD50	oral	> 316mg/kg (316mg/kg)		Ecotoxicology and Environmental Safety. Vol. 6, Pg. 149, 1982.