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119-93-7

Basic Information
CAS No.: 119-93-7
Name: 3,3'-Dimethylbenzidine
Molecular Structure:
Molecular Structure of 119-93-7 (3,3'-Dimethylbenzidine)
Formula: C14H16N2
Molecular Weight: 212.29
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;
EINECS: 204-358-0
Density: 1.106 g/cm3
Melting Point: 128-131 °C(lit.)
Boiling Point: 361 °C at 760 mmHg
Flash Point: 205.1 °C
Solubility: insoluble in water
Appearance: light grey-green to grey powder
Hazard Symbols: ToxicT,DangerousN
Risk Codes: 45-68-51/53-22
Safety: 53-45-61
Transport Information: UN 3082 9/PG 3
PSA: 52.04000
LogP: 4.29720
Synthetic route

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

119-93-7

o-tolidin

Conditions
ConditionsYield
With hydrogenchloride In ethanol at 80℃; for 2h;81%
617-22-1

2,2'-dimethylhydrazobenzene

119-93-7

o-tolidin

Conditions
ConditionsYield
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
ConditionsYield
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

88-72-2

1-methyl-2-nitrobenzene

119-93-7

o-tolidin

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
beim Schmelzen;
584-90-7

trans-di-o-tolyl-diazene

119-93-7

o-tolidin

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With hydrogenchloride; acetic acid; tin(ll) chloride for 2h; Title compound not separated from byproducts;
584-90-7

2,2'-dimethylazobenzene

119-93-7

o-tolidin

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

7782-99-2

sulphurous acid

584-90-7

2,2'-dimethylazobenzene

potassium iodide

potassium iodide

119-93-7

o-tolidin

Conditions
ConditionsYield
at 40 - 50℃;
64-17-5

ethanol

584-90-7

2,2'-dimethylazobenzene

tin dichloride

tin dichloride

119-93-7

o-tolidin

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

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
ConditionsYield
at -40℃; Behandeln des Reaktionsprodukts mit Wasser;
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

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

o-hydrazotoluene

o-hydrazotoluene

119-93-7

o-tolidin

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
bei der elektrolytischen Reduktion;
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

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

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

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

119-93-7

o-tolidin

98-09-9

benzenesulfonyl chloride

6324-67-0

N,N'-(3,3'-dimethylbiphenyl-4,4'-diyl)dibenzenesulfonamide

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
In tetrahydrofuran85%
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With sodium hydroxide In 1,4-dioxane at 20℃; for 0.2h;84%
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91-96-3
612-75-9
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    C.I. 37230

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  • Casno:

    119-93-7

    Low price high 3,3'-Dimethylbenzidine 119-93-7

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Chemistry

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

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.

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.

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.

Safety Profile

Hazard Codes: ToxicT, DangerousN
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 NOx.

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

Analytical Methods

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

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.