3,3',5,5'-Tetramethylbenzidine supplier

Name
Tetramethylbenzidine
EINECS 259-364-6
CAS No. 54827-17-7
Article Data17
CAS DataBase
Density 1.071 g/cm³
Solubility <0.1 g/100 mL at 20 °C in water
Melting Point 168-171 °C(lit.)
Formula C₁₆H₂₀N₂
Boiling Point 368.623 °C at 760 mmHg
Molecular Weight 240.348
Flash Point 210.8 °C
Transport Information UN 2796 8/PG 2
Appearance White or light yellow solid
Safety 26-36-36/37
Risk Codes 36/38-36/37/38-22
Molecular Structure
Hazard Symbols Xn, Xi
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;
PSA 52.04000
LogP 4.91400

Synthetic route

: 29418-31-3
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

: 24596-18-7
4-chloro-2,6-dimethylaniline

: 54827-17-7
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%

: 80387-68-4
2-methylindole-3-carboxaldehyde 2,6-dimethylphenylhydrazone

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

B: 80387-72-0
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

: 603-77-0
(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

: 1004761-68-5
2,6-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

: 24596-19-8
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

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

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

Conditions

Conditions	Yield
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

: 63615-06-5
2,2′,6,6′-(tetramethyldiphenyl)hydrazine

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

Conditions

Conditions	Yield
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

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

Conditions

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

: C30H28N2

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

Conditions

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

: 868961-34-6
oxo-(2,4,6-trimethylphenylamino)acetyl chloride

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

: 1071505-64-0
C38H42N4O4

Conditions

Conditions	Yield
In tetrahydrofuran	96%

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

: 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

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

: 75-44-5
phosgene

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

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

Conditions

Conditions	Yield
In various solvent(s) for 0.5h; Condensation; Heating;	90%

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

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

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

Conditions

Conditions	Yield
In dichloromethane at 20℃; Substitution;	88%

: 2-isothiocyanato-6-methylpyridine

: 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)

Conditions

Conditions	Yield
In methanol at 20℃;	85%

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

Conditions

Conditions	Yield
With hydrogenchloride In water; ethyl acetate for 0.5h; Solvent;	85%

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

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

Conditions

Conditions	Yield
With potassium dichromate; perchloric acid; acetic acid In water	84.3%

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

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

Conditions

Conditions	Yield
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;

: 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

: 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

Conditions	Yield
With pyridine; titanium tetrachloride In tetrahydrofuran at 25℃; for 48h; Reagent/catalyst; Temperature;	82%

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

: 2284-20-0
4-Methoxyphenyl isothiocyanate

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

Conditions

Conditions	Yield
In methanol at 20℃;	78%

: tetrakis(dimethylamido)titanium(IV)

: 75-77-4
chloro-trimethyl-silane

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

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

Conditions

Conditions	Yield
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%

...Expand

: 35967-24-9
(3,4,5-trimethoxyphenyl)isothiocyanate

: 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)

Conditions

Conditions	Yield
In methanol at 20℃;	75%

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

: 23165-44-8
p-butylphenyl isothiocyanate

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

Conditions

Conditions	Yield
In methanol at 20℃;	75%

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

: 2131-55-7
4-Chlorophenyl isothiocyanate

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

Conditions

Conditions	Yield
In methanol at 20℃;	75%

: 24677-78-9
2,3-dihydroxybenzaldehyde

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

: C30H28N2O4

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In toluene Heating;	72%

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

: 90-02-8
salicylaldehyde

: C30H28N2O2

Conditions

Conditions	Yield
In methanol at 70℃; for 3h; Inert atmosphere;	70%

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

: 100-52-7
benzaldehyde

: C30H28N2

Conditions

Conditions	Yield
In methanol at 70℃; for 3h; Inert atmosphere;	70%

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

: 551-06-4
1-isothiocyanatonaphthalene

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

Conditions

Conditions	Yield
In methanol at 20℃;	70%

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

: 2131-61-5
p-nitrophenyl isothiocyanate

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

Conditions

Conditions	Yield
In methanol at 20℃;	68%

: 1121-60-4
pyridine-2-carbaldehyde

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

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

Conditions

Conditions	Yield
In ethanol Heating / reflux;	62%

: 500-22-1
3-pyridinecarboxaldehyde

: 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)

Conditions

Conditions	Yield
With formic acid In ethanol; dichloromethane at 20℃;	62%

: 57146-54-0
oxodichloro-bis-diethyldithiocarbamato molybdenum(VI)

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

Conditions

Conditions	Yield
In methanol (N2); stirring (25°C, 10 h); filtn., solvent removal, washing (light petroleum, Et2O);	56%

: 24463-19-2
anthracenylmethyl chloride

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

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

Conditions

Conditions	Yield
With triethylamine In toluene Heating;	55%

: 395656-36-7
2-acetyl-6-[1-((2,6-dimethylphenyl)imino)ethyl]pyridine

: 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

Conditions	Yield
With p-toluene sulfinic acid In toluene for 24h; Reflux;	49.3%

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

: 6203-18-5
p-dimethylaminocinnamaldehyde

: 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

Conditions	Yield
In ethanol at 90℃; for 12h; Inert atmosphere;	48%

: 20432-35-3, 6203-18-5
3-(4-dimethylamino-phenyl)-propenal

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

: 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

Conditions	Yield
In ethanol at 90℃; for 12h; Inert atmosphere;	48%

: 540-80-7
tert.-butylnitrite

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

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

Conditions

Conditions	Yield
In Bromoform; ethyl acetate	43%
In Bromoform; ethyl acetate	43%

3,3',5,5'-Tetramethylbenzidine Consensus Reports

EPA Genetic Toxicology Program. Reported in EPA TSCA Inventory.

3,3',5,5'-Tetramethylbenzidine 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.

Product Name

Tetramethylbenzidine

Synthetic route

3,3',5,5'-Tetramethylbenzidine Consensus Reports

3,3',5,5'-Tetramethylbenzidine Specification

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