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Cas Database |
| Name |
3,3'-Dimethylbenzidine |
EINECS | 204-358-0 |
| CAS No. | 119-93-7 | Density | 1.106 g/cm3 |
| PSA | 52.04000 | LogP | 4.29720 |
| 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; |
Article Data | 39 |
3,3'-Dimethylbenzidine Synthetic route
- 119-93-7
o-tolidin
| Conditions | Yield |
|---|---|
| With hydrogenchloride In ethanol at 80℃; for 2h; | 81% |
| 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 | Yield |
|---|---|
| With lithium aluminium tetrahydride In diethyl ether for 24h; Reduction; Heating; | 24% |
| 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 |
| Conditions | Yield |
|---|---|
| With sulfuric acid bei der elektrolytischen Reduktion, an Kohlenstoffanode und Platinkathode; |
| Conditions | Yield |
|---|---|
| at 250℃; |
B
- 119-93-7
o-tolidin
| Conditions | Yield |
|---|---|
| beim Schmelzen; |
| 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 | Yield |
|---|---|
| Product distribution; Mechanism; various pH; comparison with other reducing agent : Zn; electrochemical reduction; |
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: 
T, 
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 NOx.
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.
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