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3-(Phenylazo)-2,6-pyridinediamine

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Name

3-(Phenylazo)-2,6-pyridinediamine

EINECS 202-363-2
CAS No. 94-78-0 Density 1.32 g/cm3
PSA 89.65000 LogP 3.82380
Solubility 904.20g/L(25 oC) Melting Point 139 °C
Formula C11H11N5 Boiling Point 442.3 °C at 760 mmHg
Molecular Weight 213.242 Flash Point 221.3 °C
Transport Information N/A Appearance dark red to violet crystalline powder
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 94-78-0 (3-(PHENYLAZO)-2,6-PYRIDINEDIAMINE) Hazard Symbols N/A
Synonyms

2,6-Pyridinediamine,3-(phenylazo)- (9CI);Pyridine, 2,6-diamino-3-(phenylazo)- (6CI,7CI,8CI);2,6-Diamino-3-phenylazopyridine;Gastracid;Gastrotest;NSC 145895;Phenazopyridine;3-Phenylazopyridine-2,6-diamine;

Article Data 8

3-(Phenylazo)-2,6-pyridinediamine Synthetic route

108-24-7

acetic anhydride

94-78-0

phenazopyridine

5222-90-2

2,6-bis-acetylamino-3-phenylazo-pyridine

Conditions
ConditionsYield
With pyridine at 20℃;88%
108-24-7

acetic anhydride

94-78-0

phenazopyridine

A

N-(6-amino-3-phenylazo-pyridin-2-yl)-acetamide

B

5222-90-2

2,6-bis-acetylamino-3-phenylazo-pyridine

Conditions
ConditionsYield
With pyridine at 20℃; for 3h;A 79%
B 12%

3-(Phenylazo)-2,6-pyridinediamine Consensus Reports

IARC Cancer Review: Animal Inadequate Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 8 ,1975,p. 117.(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) .

3-(Phenylazo)-2,6-pyridinediamine Specification

The 2,6-Pyridinediamine,3-(2-phenyldiazenyl)-, with the CAS registry number 94-78-0, is also known as 2,6-Diamino-3-phenylazopyridine. It belongs to the product categories of Aromatics; Bases & Related Reagents; Heterocycles; Intermediates & Fine Chemicals; Nucleotides; Pharmaceuticals. Its EINECS number is 202-363-2. This chemical's molecular formula is C11H11N5 and molecular weight is 213.24. What's more, its systematic name is 3-phenylazopyridine-2,6-diamine. Its classification codes are: (1)Drug / Therapeutic Agent; (2)Tumor data. It is a local anesthetic that has been used in urinary tract disorders. Its use is limited by problems with toxicity (primarily blood disorders) and potential carcinogenicity. 

Physical properties of 2,6-Pyridinediamine,3-(2-phenyldiazenyl)- are: (1)ACD/LogP: 2.94; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.9; (4)ACD/LogD (pH 7.4): 2.94; (5)#H bond acceptors: 5; (6)#H bond donors: 4; (7)#Freely Rotating Bonds: 2; (8)Polar Surface Area: 89.65 Å2; (9)Index of Refraction: 1.687; (10)Molar Refractivity: 61.13 cm3; (11)Molar Volume: 160.3 cm3; (12)Polarizability: 24.23×10-24cm3; (13)Surface Tension: 58.2 dyne/cm; (14)Density: 1.32 g/cm3; (15)Flash Point: 221.3 °C; (16)Enthalpy of Vaporization: 69.97 kJ/mol; (17)Boiling Point: 442.3 °C at 760 mmHg; (18)Vapour Pressure: 5.1E-08 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: Nc2nc(N)ccc2N=Nc1ccccc1
(2)Std. InChI: InChI=1S/C11H11N5/c12-10-7-6-9(11(13)14-10)16-15-8-4-2-1-3-5-8/h1-7H,(H4,12,13,14)
(3)Std. InChIKey: QPFYXYFORQJZEC-UHFFFAOYSA-N 

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man TDLo oral 4693mg/kg/3Y- (4693mg/kg) KIDNEY, URETER, AND BLADDER: OTHER CHANGES IN URINE COMPOSITION

BLOOD: METHEMOGLOBINEMIA-CARBOXYHEMOGLOBIN

SKIN AND APPENDAGES (SKIN): NAILS: OTHER
Annals of Internal Medicine. Vol. 127, Pg. 1137, 1997.
mouse LD50 oral 580mg/kg (580mg/kg)   Pharmaceutica Acta Helvetiae. Vol. 35, Pg. 423, 1960.
rat LD50 intraperitoneal 560mg/kg (560mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: STRUCTURAL OR FUNCTIONAL CHANGE IN TRACHEA OR BRONCHI

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Journal of Pharmacology and Experimental Therapeutics. Vol. 51, Pg. 200, 1934.

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