2-Methyl-5-(p-tolyldiazenyl)aniline is a biochemical compound that may be utilized as a biomaterial or organic/chemical reagent for biomedical research.

Physicochemical Properties

Molecular Formula	C14H15N3
Molecular Weight	225.29
Exact Mass	225.127
CAS #	97-56-3
PubChem CID	7340
Appearance	GOLDEN CRYSTALS REDDISH-BROWN TO YELLOW CRYSTALS YELLOW LEAVES FROM ALCOHOL
Density	1.09 g/cm3
Boiling Point	407.7ºC at 760 mmHg
Melting Point	101-102 °C
Flash Point	200.4ºC
Index of Refraction	1.571
LogP	4.882
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	2
Heavy Atom Count	17
Complexity	264
Defined Atom Stereocenter Count	0
SMILES	N(C1C=C(C)C(N)=CC=1)=NC1C(C)=CC=CC=1
InChi Key	PFRYFZZSECNQOL-UHFFFAOYSA-N
InChi Code	InChI=1S/C14H15N3/c1-10-5-3-4-6-14(10)17-16-12-7-8-13(15)11(2)9-12/h3-9H,15H2,1-2H3
Chemical Name	2-methyl-4-[(2-methylphenyl)diazenyl]aniline
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

ADME/Pharmacokinetics

Absorption, Distribution and Excretion AFTER ORAL DOSING WITH (3)H-AAT FOR 2-4 WK, RADIOACTIVITY WAS FOUND IN NUCLEIC ACIDS & PROTEIN. RADIOACTIVITY COULD NO LONGER BE DETECTED BOUND TO PROTEIN AFTER 28 DAYS, BUT WAS PRESENT IN BOTH RNA & DNA 84 DAYS AFTER SINGLE DOSE OF (3)H-AAT. USING AUTORADIOGRAPHY WITH (3)H-AAT & IMMUNOFLUORESCENCE, CMPD WAS SHOWN TO BE TAKEN UP BY PERIPORTAL AREAS OF LIVER LOBULES. RADIOACTIVITY WAS DISTRIBUTED IN ALL PARTS OF CELLS; HOWEVER, BY FLUORESCENCE MICROSCOPY AAT-SPECIFIC ANTIGEN WAS DETECTED IN CYTOPLASMIC GRANULES & AROUND MEMBRANES OF NUCLEUS & NUCLEOLUS. Metabolism / Metabolites LIVERS OF MICE & RATS DOSED WITH AAT CONTAIN FOUR PREVIOUSLY UNIDENTIFIED CMPD, ONE OF WHICH WAS FOUND LATER TO BE 4,4'-BIS(ORTHO-TOLYLAZO)-2,2'-DIMETHYLAZOBENZENE. BILE OF RATS DOSED WITH AAT CONTAINS N-GLUCURONIDE OF AAT, N-GLUCURONIDE OF CORRESPONDING 2-HYDROXYMETHYL DERIVATIVE (IE, 4-AMINO-2-HYDROXYMETHYL-3'-METHYLAZOBENZENE, SULFATE & GLUCURONIDES OF 4-AMINO-4'-HYDROXYAZOTOLUENE & N-GLUCURONIDE-O-SULFATE OF 4'-HYDROXYAZOTOLUENE). IN RABBITS, PARA-TOLUENEDIAMINE IS FORMED ... . AZO LINKAGE OF AAT IS EASILY REDUCED BY YEAST TO GIVE ORTHO-TOLUIDINE & 2-METHYL-1,4-PHENYLENEDIAMINE ... . [2-methyl-4-(o-tolylazo)phenyl]amine has known human metabolites that include 2'-hydroxymethyl-3-raethyl-4-aminoazoberizene, 4'-hydroxy-o-aminoazotoJuene, and N-hydroxy-oaminoazotohiene.

Additional Infomation

o-Aminoazotoluene can cause cancer according to an independent committee of scientific and health experts. Reddish-brown to golden crystals; orangish red powder. Odorless. (NTP, 1992) Ortho-Aminoazotoluene is a member of azobenzenes. o-Aminoazotoluene is a synthetic organic azo dye used mainly in experimental research, carcinogenic o-Aminoazotoluene induces hepatomas, lung tumors, bladder tumors, and lung hemangioendotheliomas in animals when administered in the diet. (NCI04) An azo dye with carcinogenic properties. Mechanism of Action Increase in the chemical carcinogenicity of aromatic amines due to the presence of methyl groups and aromatic rings is examined. Based on the multistage process of carcinogenesis, data indicate that methyl groups and aromatic amines convert initiators into complete carcinogens. Experiments on rats with aromatic amines show that o-aminoazotoluene and 4-dimethylaminobenzene induce liver tumors. 4-Aminobenzene, considered a tumor initiator, also induces liver tumors in rats. The methyl groups are specifically active; 4-diethylaminobenzene is not carcinogenic whereas 4-dimethylaminobenzene is. Several studies with the aromatic hydrocarbons phenanthrene, chrysene, and benz(a)anthracene show them to be either noncarcinogenic, weakly carcinogenic, or tumor initiators. The methyl derivatives trimethylphenanthrene and 1,2,3,4-tetramethylphenanthrene are weak but not positive skin carcinogens in mice. 7,12-Dimethylbenz(a)anthracene is a very potent tumor promoter. Benzene rings also contribute to the carcinogenic process. It was concluded that in many cases the increase in carcinogenic activity after methyl groups are introduced into the molecule is due to tumor promoting rather than initiating activity.

Solubility Data

Solubility (In Vitro)

May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples

Solubility (In Vivo)

Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	4.4387 mL	22.1936 mL	44.3872 mL
	5 mM	0.8877 mL	4.4387 mL	8.8774 mL
	10 mM	0.4439 mL	2.2194 mL	4.4387 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.