3,3'-Dimethylbenzidine supplier

Name
C.I. 37230
EINECS 204-358-0
CAS No. 119-93-7
Article Data39
CAS DataBase
Density 1.106 g/cm³
Solubility insoluble in water
Melting Point 128-131 °C(lit.)
Formula C₁₄H₁₆N₂
Boiling Point 361 °C at 760 mmHg
Molecular Weight 212.294
Flash Point 205.1 °C
Transport Information UN 3082 9/PG 3
Appearance light grey-green to grey powder
Safety 53-45-61
Risk Codes 45-68-51/53-22
Molecular Structure
Hazard Symbols T,N
Synonyms Benzidine,3,3'-dimethyl- (8CI);3,3'-Dimethyl-4,4'-biphenyldiamine;3,3'-Dimethyl-4,4'-diaminobiphenyl;3,3'-Dimethylbenzidine;3,3'-Tolidine;4,4'-Diamino-3,3'-dimethyl-1,1'-biphenyl;4,4'-Diamino-3,3'-dimethylbiphenyl;4'-Amino-3,3'-dimethyl[1,1'-biphenyl]-4-ylamine;C.I. 37230;C.I. Azoic DiazoComponent 113;Fast Dark Blue Base R;o,o'-Tolidine;[1,1'-Biphenyl]-4,4'-diamine,3,3'-dimethyl-;o-Tolidine;
PSA 52.04000
LogP 4.29720

Synthetic route

: N,N'-di-o-tolyl-hydrazinecarboxylic acid tert-butyl ester

: 119-93-7
o-tolidin

Conditions

Conditions	Yield
With hydrogenchloride In ethanol at 80℃; for 2h;	81%

: 617-22-1
2,2'-dimethylhydrazobenzene

: 119-93-7
o-tolidin

Conditions

Conditions	Yield
Stage #1: 2,2'-dimethylhydrazobenzene With hydrogenchloride In water at 30 - 90℃; for 2h; Stage #2: With water; sodium hydroxide pH=9 - 10;	65.3%
With hydrogenchloride; sodium hydrogensulfite; xylene

: 15403-45-9
Dimethyl 4,4'-diamino-3,3'-biphenylylenedicarboxylate

: 119-93-7
o-tolidin

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether for 24h; Reduction; Heating;	24%

: 64-17-5
ethanol

: 5-oxo-1-phenyl-2,5-dihydro-1H-[1,2,3]triazole-4-carboxylic acid methyl ester; o-tolidine salt

A: diazomalonic acid methyl ester-anilide

B: 119-93-7
o-tolidin

...Expand

: 88-72-2
1-methyl-2-nitrobenzene

: 119-93-7
o-tolidin

Conditions

Conditions	Yield
With sodium carbonate; palladium; isopropyl alcohol at 80℃; under 7355.08 Torr; anschliessend Behandeln mit wss.Salzsaeure und mit Eisen;
Multi-step reaction with 2 steps 1.1: sodium dodecylbenzenesulfonate; 0.8wt% Pd/C; hydrogen; sodium hydroxide; [1,4]naphthoquinone / ethanol / 30 °C / 4500.45 Torr / Autoclave 2.1: hydrogenchloride / water / 2 h / 30 - 90 °C 2.2: pH 9 - 10 View Scheme

: 88-72-2
1-methyl-2-nitrobenzene

A: 119-93-7
o-tolidin

B: 95-53-4
o-toluidine

Conditions

Conditions	Yield
With sulfuric acid bei der elektrolytischen Reduktion, an Kohlenstoffanode und Platinkathode;

: 83-83-0
o-tolidine-6,6'-disulfonic acid

: 119-93-7
o-tolidin

Conditions

Conditions	Yield
at 250℃;

: 5-oxo-1-phenyl-2,5-dihydro-1H-[1,2,3]triazole-4-carboxylic acid methyl ester; o-tolidine salt

A: diazomalonic acid methyl ester-anilide

B: 119-93-7
o-tolidin

Conditions

Conditions	Yield
beim Schmelzen;

: 584-90-7
trans-di-o-tolyl-diazene

: 119-93-7
o-tolidin

Conditions

Conditions	Yield
With ethanol; tin(ll) chloride
With hydrogenchloride; water; sulphurous acid at 40 - 50℃; Reagens 4: Jodkalium;

: 2538-83-2
trypane blue

A: 119-93-7
o-tolidin

B: 3545-88-8
3,5-diamino-4-hydroxy-naphthalene-2,7-disulfonic acid

Conditions

Conditions	Yield
Product distribution; Mechanism; various pH; comparison with other reducing agent : Zn; electrochemical reduction;

: 102276-74-4
2,2'-dimethyl-4-nitro-ONN-azoxybenzene

A: 119-93-7
o-tolidin

B: 3,3'-Dimethyl-biphenyl-2,5,4'-triamine

C: 95-53-4
o-toluidine

D: 95-70-5
2-methyl-p-phenylenediamine

Conditions

Conditions	Yield
With hydrogenchloride; acetic acid; tin(ll) chloride for 2h; Title compound not separated from byproducts;

...Expand

: 584-90-7
2,2'-dimethylazobenzene

: 119-93-7
o-tolidin

Conditions

Conditions	Yield
Mechanism; controlled potential electrolysis; pH=2.8-4.0; -0.25 V;

: 72-57-1
trypan blue

A: 119-93-7
o-tolidin

B: 13629-82-8
3,3'-dimethyl-4-aminobiphenyl

C: 3,3'-dimethyl-4-amino-4'-hydroxybiphenyl

Conditions

Conditions	Yield
With sodium dithionate In various solvent(s) at 70℃; pH=6; Product distribution; Further Variations:; Reaction partners; Reduction;

...Expand

: 7647-01-0
hydrogenchloride

: 617-22-1
2,2'-dimethylhydrazobenzene

: 119-93-7
o-tolidin

: 60-29-7
diethyl ether

: 617-22-1
2,2'-dimethylhydrazobenzene

chlorine monoxide: chlorine monoxide

: 119-93-7
o-tolidin

...Expand

: 7732-18-5
water

: 7782-99-2
sulphurous acid

: 584-90-7
2,2'-dimethylazobenzene

potassium iodide: potassium iodide

: 119-93-7
o-tolidin

Conditions

Conditions	Yield
at 40 - 50℃;

...Expand

: 64-17-5
ethanol

: 584-90-7
2,2'-dimethylazobenzene

tin dichloride: tin dichloride

: 119-93-7
o-tolidin

...Expand

: 7647-01-0
hydrogenchloride

: 617-22-1
2,2'-dimethylhydrazobenzene

A: 119-93-7
o-tolidin

B: 109689-54-5
3,3'-dimethyl-biphenyl-2,4'-diyldiamine

...Expand

: 7647-01-0
hydrogenchloride

: 60-29-7
diethyl ether

: 617-22-1
2,2'-dimethylhydrazobenzene

A: 119-93-7
o-tolidin

B: 3-methyl-N1-o-tolyl-o-phenylenediamine

Conditions

Conditions	Yield
at -40℃; Behandeln des Reaktionsprodukts mit Wasser;

...Expand

: 7647-01-0
hydrogenchloride

: 617-22-1
2,2'-dimethylhydrazobenzene

A: 119-93-7
o-tolidin

B: 584-90-7
2,2'-dimethylazobenzene

C: 95-53-4
o-toluidine

...Expand

: 64-17-5
ethanol

: 584-90-7
2,2'-dimethylazobenzene

tin dichloride: tin dichloride

A: 119-93-7
o-tolidin

B: 956-31-0, 51284-68-5, 116723-89-8
N,N'-Di-o-tolyl-diazene N-oxide

...Expand

o-hydrazotoluene: o-hydrazotoluene

: 119-93-7
o-tolidin

Conditions

Conditions	Yield
With hypochlorous anhydride; diethyl ether; chlorine monoxide
With hydrogenchloride

o-hydrazotoluene: o-hydrazotoluene

A: 119-93-7
o-tolidin

B: 109689-54-5
3,3'-dimethyl-biphenyl-2,4'-diyldiamine

Conditions

Conditions	Yield
With hydrogenchloride

: 64-17-5
ethanol

: 88-72-2
1-methyl-2-nitrobenzene

: 7664-93-9
sulfuric acid

carbon anode: carbon anode

platinum cathode: platinum cathode

A: 119-93-7
o-tolidin

B: 95-53-4
o-toluidine

Conditions

Conditions	Yield
bei der elektrolytischen Reduktion;

...Expand

: 83-83-0
o-tolidine-6,6'-disulfonic acid

lime/chalk/: lime/chalk/

: 119-93-7
o-tolidin

: 7647-01-0
hydrogenchloride

: 92245-52-8
3,3'-dimethyl-4'-nitro-biphenyl-4-ylamine

tin: tin

: 119-93-7
o-tolidin

...Expand

: 7647-01-0
hydrogenchloride

: 5-oxo-1-phenyl-2,5-dihydro-1H-[1,2,3]triazole-4-carboxylic acid methyl ester; o-tolidine salt

A: 119-93-7
o-tolidin

B 1-phenyl-1.2.3-triazolone-(5)-carboxylic acid-(4)-methyl ester: 1-phenyl-1.2.3-triazolone-(5)-carboxylic acid-(4)-methyl ester

...Expand

: 5-oxo-1-phenyl-2,5-dihydro-1H-[1,2,3]triazole-4-carboxylic acid methyl ester; o-tolidine salt

natrium carbonate: natrium carbonate

A: 119-93-7
o-tolidin

B 1-phenyl-1.2.3-triazolone-(5)-carboxylic acid-(4)-methyl ester: 1-phenyl-1.2.3-triazolone-(5)-carboxylic acid-(4)-methyl ester

...Expand

: 2-diazo-N-phenyl-malonamic acid methyl ester; compound with 3,3'-dimethyl-benzidine

diluted hydrochloric acid: diluted hydrochloric acid

A: diazomalonic acid methyl ester-anilide

B: 119-93-7
o-tolidin

...Expand

: 119-93-7
o-tolidin

: 98-09-9
benzenesulfonyl chloride

: 6324-67-0
N,N'-(3,3'-dimethylbiphenyl-4,4'-diyl)dibenzenesulfonamide

Conditions

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 4h; pH=Ca. 8;	98%
With pyridine

: 119-93-7
o-tolidin

: 774-74-3
2-(2,4-dichlorophenoxy)acetyl chloride

: 2-(2,4-dichloro-phenoxy)-N-{4'-[2-(2,4-dichloro-phenoxy)-acetylamino]-3,3'-dimethyl-biphenyl-4-yl}-acetamide

Conditions

Conditions	Yield
With sodium hydroxide; PEG-600 In dichloromethane; water at 20℃; for 1h; Acylation;	98%

: 353-50-4
Carbonyl fluoride

: 119-93-7
o-tolidin

: 3,3'-dimethylbiphenyl-4,4'-dicarbamayl fluoride

Conditions

Conditions	Yield
In chlorobenzene; acetone at 20℃; for 3h; Glovebox;	98%

: 119-93-7
o-tolidin

: 108-24-7
acetic anhydride

: 3546-11-0
3,3'-dimethyl-4,4'-diacetylaminobiphenyl

Conditions

Conditions	Yield
for 0.00277778h; Green chemistry;	97%

: 626-60-8
3-Chloropyridine

: 119-93-7
o-tolidin

: N-{2-methyl-4-[3-methyl-4-(3-piridylamino)phenyl]phenyl}-3-pyridinamine

Conditions

Conditions	Yield
With sodium t-butanolate; Ni(0)*2IPr In 1,4-dioxane at 100℃;	95%

: 119-93-7
o-tolidin

: 108-90-7
chlorobenzene

: N-phenyl-4-(4-anilino3-methylphenyl)-2-methylaniline

Conditions

Conditions	Yield
With sodium t-butanolate; Ni(0)*2IPr In 1,4-dioxane at 100℃;	95%

: 24677-78-9
2,3-dihydroxybenzaldehyde

: 119-93-7
o-tolidin

: C28H24N2O4

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In toluene Heating;	91%

: 119-93-7
o-tolidin

: 90-02-8
salicylaldehyde

: 16182-38-0
N,N'-bis(salicylidene)-o-tolidine

Conditions

Conditions	Yield
With formic acid In ethanol at 20℃;	90%
With ethanol

: 17610-00-3
3,5-Di-tert-butylbenzaldehyde

: 119-93-7
o-tolidin

: (N4E,N4'E)-N4,N4'-bis(3,5-di-tert-butylbenzylidene)-3,3'-dimethyl[1,1'-biphenyl]-4,4'-diamine

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 130℃; for 24h; Molecular sieve; Autoclave;	90%

: 99-34-3
3,5-dinitrobenzoic acid

: 119-93-7
o-tolidin

: 3,3'-dimethyl-biphenyl-4,4'-diamine; compound with 3,5-dinitro-benzoic acid

Conditions

Conditions	Yield
In ethanol at 20℃; for 0.25h;	89%

: 12093-10-6
ferrocenecarboxaldehyde

: 119-93-7
o-tolidin

: 186822-62-8
[(η(5)-C5H5)Fe(η(5)-C5H4CH=NC6H3-2-Me-)]2

Conditions

Conditions	Yield
In benzene byproducts: H2O; mixing dimethylbenzidine with 2 equiv. of Fe-complex soln. at 20°C, azeotropic distn. off of H2O; hot filtration, evapn. (vac.), treatment with hexane, filtration, dryingin air; elem. anal.;	89%
With aluminum oxide In toluene ferrocene in toluene treated with benzidine, refluxed (Ar) for 3 days inthe presence of Al2O3; hot filtered, concd.(vac.), washed (ethanol), dried (vac.), elem. anal.;	89%

: 119-93-7
o-tolidin

: 91-68-9
3-diethylaminophenol

: C34H40N6O2

Conditions

Conditions	Yield
Stage #1: o-tolidin With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 1h; Stage #2: 3-diethylaminophenol In water at 0 - 5℃; for 2h; pH=5-6;	88.3%

: 92-50-2
2-( N-ethylanilino)ethanol

: 119-93-7
o-tolidin

: C34H40N6O2

Conditions

Conditions	Yield
Stage #1: o-tolidin With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 1h; Stage #2: 2-( N-ethylanilino)ethanol In water at 0 - 5℃; for 2h; pH=5-6;	87.1%

: 119-93-7
o-tolidin

: 120-21-8
4-Diethylaminobenzaldehyde

: bis[4-(diethylamino)benzylidene]-3,3'-dimethylbiphenyl-4,4'-diamine

Conditions

Conditions	Yield
With acetic acid In ethanol at 70 - 80℃; for 0.583333h;	87%

: 2460-58-4
2-hydroxy-4-nitrobenzaldehyde

: 119-93-7
o-tolidin

: C28H22N4O6

Conditions

Conditions	Yield
With acetic acid In ethanol at 80 - 85℃;	86.5%

: 119-93-7
o-tolidin

: 94-34-8
N-(2-cyanoethyl)-N-methylaniline

: C34H34N8

Conditions

Conditions	Yield
Stage #1: o-tolidin With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 1h; Stage #2: N-(2-cyanoethyl)-N-methylaniline In water at 0 - 5℃; for 2h; pH=5-6;	85.2%

: 119-93-7
o-tolidin

: 90-02-8
salicylaldehyde

: 16182-38-0
2,2'-((1E,1'E)-((3,3'-dimethyl-[1,1'-biphenyl]-4,4'-diyl)bis(azanylylidene))bis(methanylylidene))diphenol

Conditions

Conditions	Yield
With acetic acid In ethanol for 8h; Reflux;	85.1%

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

: 119-93-7
o-tolidin

: 1071505-63-9
C36H38N4O4

Conditions

Conditions	Yield
In tetrahydrofuran	85%

: 119-93-7
o-tolidin

: 298-12-4
Glyoxilic acid

: 2,2'-(3,3'-dimethylbiphenyl-4,4'-diyl)bis(azan-1-yl-1-ylidene)diacetic acid

Conditions

Conditions	Yield
With acetic acid In ethanol Reflux;	85%

: 119-93-7
o-tolidin

: 2872-47-1
1-amino-4-chloroanthraquinone

: 88653-20-7
1-amino-4-(4'-amino-2,3'-dimethylbiphenylylamino)anthraquinone

Conditions

Conditions	Yield
With aluminium trichloride In nitrobenzene Ambient temperature;	84%

: 119-93-7
o-tolidin

: 91-13-4
α,α'-dibromo-o-xylene

: 1197914-43-4
4,4'-di-(2,3-dihydro-1H-isoindol-2-yl)-3,3'-dimethyl-biphenyl

Conditions

Conditions	Yield
With sodium hydroxide In 1,4-dioxane at 20℃; for 0.2h;	84%

3,3'-Dimethylbenzidine Chemical Properties

Molecule structure of o-Tolidine (CAS NO.119-93-7):

IUPAC Name: 4-(4-Amino-3-methylphenyl)-2-methylaniline
Molecular Weight: 212.29024 g/mol
Molecular Formula: C₁₄H₁₆N₂
Density: 1.106 g/cm³
Melting Point: 128-131 °C(lit.)
Boiling Point: 361 °C at 760 mmHg
Flash Point: 205.1 °C
Index of Refraction: 1.638
Molar Refractivity: 68.96 cm³
Molar Volume: 191.8 cm³
Surface Tension: 49 dyne/cm
Enthalpy of Vaporization: 60.67 kJ/mol
Vapour Pressure: 2.14E-05 mmHg at 25 °C
XLogP3: 2.3
H-Bond Donor: 2
H-Bond Acceptor: 2
Rotatable Bond Count: 1
Exact Mass: 212.131349
MonoIsotopic Mass: 212.131349
Topological Polar Surface Area: 52
Heavy Atom Count: 16
Canonical SMILES: CC1=C(C=CC(=C1)C2=CC(=C(C=C2)N)C)N
InChI: InChI=1S/C14H16N2/c1-9-7-11(3-5-13(9)15)12-4-6-14(16)10(2)8-12/h3-8H,15-16H2,1-2H3
InChIKey: NUIURNJTPRWVAP-UHFFFAOYSA-N
EINECS: 204-358-0
Product Categories: Intermediates of Dyes and Pigments; Organics

3,3'-Dimethylbenzidine Uses

o-Tolidine (CAS NO.119-93-7) is a commercially important aromatic amines used mainly for dye production, but also for the production of certain elastomers. It is also widely used as a reagent or indicator in analytical, clinical and forensic chemistry, such as in the analytical determination of gold. o-Tolidine is used as an intermediate for the production of soluble azo dyes and insoluble pigments used particularly in the textile, leather and paper industries.

3,3'-Dimethylbenzidine Toxicity Data With Reference

1.	dns-hmn:hla 1 µmol/L	CNREA8 Cancer Research. 38 (1978),2621.
2.	dns-rat:lvr 1 µmol/L	MUREAV Mutation Research. 136 (1984),255.
3.	orl-rat TDLo:4500 mg/kg/27D-I:CAR	CNREA8 Cancer Research. 28 (1968),924.
4.	ipr-rat LDLo:125 mg/kg	CBCCT* “Summary Tables of Biological Tests“ National Research Council Chemical-Biological Coordination Center. 6 (1954),64.
5.	ipr-mus LDLo:125 mg/kg	CBCCT* “Summary Tables of Biological Tests“ National Research Council Chemical-Biological Coordination Center. 6 (1954),64.

3,3'-Dimethylbenzidine Consensus Reports

NTP 10th Report on Carcinogens. IARC Cancer Review: Group 2B IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 ,1987,p. 56.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Limited Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 1 ,1972,p. 87.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . EPA Genetic Toxicology Program. Community Right-To-Know List. Reported in EPA TSCA Inventory.

3,3'-Dimethylbenzidine Safety Profile

Hazard Codes: Toxic T, Dangerous N
Risk Statements: 45-68-51/53-22
R45:May cause cancer.
R68:Possible risk of irreversible effects.
R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
R22:Harmful if swallowed.
Safety Statements: 53-45-61
S53:Avoid exposure - obtain special instructions before use.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S61:Avoid release to the environment. Refer to special instructions / safety data sheets.
RIDADR: UN 3082 9/PG 3
WGK Germany: 3
RTECS: DD1225000
F: 8
HazardClass: 6.1(b)
PackingGroup: III
Confirmed carcinogen with experimental carcinogenic and tumorigenic data. Poison by intraperitoneal route. Moderately toxic by ingestion. Human mutation data reported. When heated to decomposition it emits toxic fumes of NO_x.

3,3'-Dimethylbenzidine Standards and Recommendations

ACGIH TLV: Animal Carcinogen
DFG MAK: Animal Carcinogen, Suspected Human Carcinogen
NIOSH REL: (o-Toluidine) CL 0.02 mg/m³/60M; avoid skin contact

3,3'-Dimethylbenzidine Analytical Methods

For occupational chemical analysis use OSHA: #ID-71 or NIOSH: Dyes, 5013.

3,3'-Dimethylbenzidine Specification

o-Tolidine (CAS NO.119-93-7) is also named as 2-Tolidin ; 2-Tolidin [German] ; 2-Tolidina ; 2-Tolidina [Italian] ; 2-Tolidine ; 3,3'-Dimethyl-(1,1'-biphenyl)-4,4'-diamine ; 3,3'-Dimethyl-4,4'-biphenyldiamine ; 3,3'-Dimethyl-4,4'-diaminobiphenyl ; 3,3'-Dimethyl-4,4'-diphenyldiamine ; 3,3'-Dimethylbenzidine ; 3,3'-Tolidine ; 4,4'-Bi-o-toluidine ; 4,4'-Di-o-toluidine ; 4,4'-Diamino-3,3'-dimethylbiphenyl ; 4,4'-Diamino-3,3'-dimethyldiphenyl ; 4-13-00-00419 (Beilstein Handbook Reference) ; AI3-19499 ; BRN 2210640 ; Bianisidine ; C.I. 37230 ; CI Azoic diazo component 113 ; Diaminoditolyl ; Diaminotolyl ; Fast Dark Blue Base R ; HSDB 1640 ; 3,3'-Dimethylbenzidine ; RCRA waste number U095 . o-Tolidine (CAS NO.119-93-7) is light grey-green to grey powder. It is insoluble in water. o-Tolidine is sensitive to exposure to light. It may be also sensitive to prolonged exposure to air. It is a weak base that forms salts with hydrochloric acid or sulfuric acid. o-Tolidine can be acetylated. It is incompatible with strong agents. Flash point data for o-Tolidine are not available; however, it is probably combustible.

Product Name

C.I. 37230

Synthetic route

3,3'-Dimethylbenzidine Chemical Properties

3,3'-Dimethylbenzidine Uses

3,3'-Dimethylbenzidine Toxicity Data With Reference

3,3'-Dimethylbenzidine Consensus Reports

3,3'-Dimethylbenzidine Safety Profile

3,3'-Dimethylbenzidine Standards and Recommendations

3,3'-Dimethylbenzidine Analytical Methods

3,3'-Dimethylbenzidine Specification

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