Product Name

  • Name

    Phenazopyridine hydrochloride

  • EINECS 205-243-8
  • CAS No. 136-40-3
  • Density 1.2645 (rough estimate)
  • Solubility 0.01-0.1 g/100 mL at 20 ºC in water
  • Melting Point 139 ºC
  • Formula C11H11N5.HCl
  • Boiling Point 442.3 ºC at 760 mmHg
  • Molecular Weight 249.703
  • Flash Point 221.3 ºC
  • Transport Information
  • Appearance brick-red crystals
  • Safety 26-36/37-45-36/37/39-27
  • Risk Codes 22-36/37/38-40-34
  • Molecular Structure Molecular Structure of 136-40-3 (Phenazopyridine hydrochloride)
  • Hazard Symbols HarmfulXn,CorrosiveC
  • Synonyms Phenazopyridine hydrochloride [USAN];2,6-Diamino-3-(phenylazo)pyridine monohydrochloride;Bisteril;Phenyl-idium;Pyridium;Pyrazodine;Azo-Mandelamine;2,6-Pyridinediamine, 3- (phenylazo)-, monohydrochloride;Phenylazo tablets;Urobiotic-250;Urazium;Thiosulfil-A;3-(Phenylazo)-2,6-pyridinediamine, hydrochloride;2,6-Diamino-3-phenylazopyridine hydrochloride;component of Azo Gantrisin;Azo Gantanol;component of Azo-Mandelamine;Azomine;2,6-Pyridinediamine,3-(phenylazo)-,monohydrochloride;Di-Azo;Azodyne;
  • PSA 89.65000
  • LogP 4.62580

Synthetic route

2,6-Diaminopyridine
141-86-6

2,6-Diaminopyridine

aniline
62-53-3

aniline

3-phenyldiazenylpyridine-2,6-diamine monohydrochloride
136-40-3

3-phenyldiazenylpyridine-2,6-diamine monohydrochloride

Conditions
ConditionsYield
With hydrogenchloride; sodium nitrite 1) 10 min, ice-cooled, 2) r. t., 20 min; Yield given. Multistep reaction;
3-phenyldiazenylpyridine-2,6-diamine monohydrochloride
136-40-3

3-phenyldiazenylpyridine-2,6-diamine monohydrochloride

pyridium
94-78-0

pyridium

Conditions
ConditionsYield
With potassium carbonate In water; ethyl acetate at 20℃; for 0.5h;92%
With sodium hydroxide In water
salicylaldehyde
90-02-8

salicylaldehyde

3-phenyldiazenylpyridine-2,6-diamine monohydrochloride
136-40-3

3-phenyldiazenylpyridine-2,6-diamine monohydrochloride

2-({[6-amino-5-(2-phenyldiazenyl)pyridin-2-yl]imino}methyl)phenol hydrochloride
1454284-39-9

2-({[6-amino-5-(2-phenyldiazenyl)pyridin-2-yl]imino}methyl)phenol hydrochloride

Conditions
ConditionsYield
In ethanol for 2h;86%
3-phenyldiazenylpyridine-2,6-diamine monohydrochloride
136-40-3

3-phenyldiazenylpyridine-2,6-diamine monohydrochloride

5-Nitrosalicylaldehyde
97-51-8

5-Nitrosalicylaldehyde

2-({[6-amino-5-(2-phenyldiazenyl)pyridin-2-yl]imino}methyl)-4-nitrophenol hydrochloride
1454284-41-3

2-({[6-amino-5-(2-phenyldiazenyl)pyridin-2-yl]imino}methyl)-4-nitrophenol hydrochloride

Conditions
ConditionsYield
In ethanol for 2h;86%
2-hydroxy-5-methoxybenzaldehyde
672-13-9

2-hydroxy-5-methoxybenzaldehyde

3-phenyldiazenylpyridine-2,6-diamine monohydrochloride
136-40-3

3-phenyldiazenylpyridine-2,6-diamine monohydrochloride

2-({[6-amino-5-(2-phenyldiazenyl)pyridin-2-yl]imino}methyl)-4-methoxyphenol hydrochloride
1454284-40-2

2-({[6-amino-5-(2-phenyldiazenyl)pyridin-2-yl]imino}methyl)-4-methoxyphenol hydrochloride

Conditions
ConditionsYield
In ethanol for 2h;85%
3-phenyldiazenylpyridine-2,6-diamine monohydrochloride
136-40-3

3-phenyldiazenylpyridine-2,6-diamine monohydrochloride

2-hydroxynaphthalene-1-carbaldehyde
708-06-5

2-hydroxynaphthalene-1-carbaldehyde

1-({[6-amino-5-(2-phenyldiazenyl)pyridin-2-yl]imino}methyl)-2-naphthol hydrochloride
1454284-42-4

1-({[6-amino-5-(2-phenyldiazenyl)pyridin-2-yl]imino}methyl)-2-naphthol hydrochloride

Conditions
ConditionsYield
In ethanol for 2h;83%
3-phenyldiazenylpyridine-2,6-diamine monohydrochloride
136-40-3

3-phenyldiazenylpyridine-2,6-diamine monohydrochloride

A

pyrido[3,4-c]cinnoline-2,4-diamine

pyrido[3,4-c]cinnoline-2,4-diamine

B

N3-phenylpyridine-2,3,4,6-tetraamine

N3-phenylpyridine-2,3,4,6-tetraamine

C

2,6-diamino-1-(4-aminophenyl)pyridin-4(1H)-one

2,6-diamino-1-(4-aminophenyl)pyridin-4(1H)-one

D

2,3,6-triaminopyridine
4318-79-0

2,3,6-triaminopyridine

Conditions
ConditionsYield
In methanol for 12h; UV-irradiation;A 35%
B 15%
C 5%
D 12%
...Expand
3-phenyldiazenylpyridine-2,6-diamine monohydrochloride
136-40-3

3-phenyldiazenylpyridine-2,6-diamine monohydrochloride

Blue Fluorophor
4324-87-2

Blue Fluorophor

Conditions
ConditionsYield
With ammonium hydroxide; copper(II) sulfate In water for 6h; Heating;
3-phenyldiazenylpyridine-2,6-diamine monohydrochloride
136-40-3

3-phenyldiazenylpyridine-2,6-diamine monohydrochloride

C8H5NO2*C11H11N5
1374137-75-3

C8H5NO2*C11H11N5

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide / water
2: ethanol / 24 h / 60 °C
View Scheme
3-phenyldiazenylpyridine-2,6-diamine monohydrochloride
136-40-3

3-phenyldiazenylpyridine-2,6-diamine monohydrochloride

C8H8O3*C11H11N5
1374137-77-5

C8H8O3*C11H11N5

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide / water
2: ethanol / 24 h / 20 °C
View Scheme
3-phenyldiazenylpyridine-2,6-diamine monohydrochloride
136-40-3

3-phenyldiazenylpyridine-2,6-diamine monohydrochloride

C7H5NO3S*C11H11N5
1374137-78-6

C7H5NO3S*C11H11N5

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide / water
2: ethanol
View Scheme
3-phenyldiazenylpyridine-2,6-diamine monohydrochloride
136-40-3

3-phenyldiazenylpyridine-2,6-diamine monohydrochloride

2ClH*C22H18N10

2ClH*C22H18N10

Conditions
ConditionsYield
With multi-walled carbon nanotubes modified with ZnCrFeO4 magnetic nanoparticles (MWCNTs/ZnCrFeO4/CPE) In aq. phosphate buffer pH=2; Reagent/catalyst; Electrochemical reaction;

Phenazopyridine hydrochloride Chemical Properties


IUPAC Name: 3-Phenyldiazenylpyridine-2,6-diamine
Molecular Formula: C11H12ClN5
Molecular Weight: 249.70 g/mol
Canonical SMILES: c1(c(nc(N)cc1)N)\N=N/c1ccccc1.Cl
InChI: InChI=1/C11H11N5.ClH/c12-10-7-6-9(11(13)14-10)16-15-8-4-2-1-3-5-8;/h1-7H,(H4,12,13,14);1H/b16-15-; 
EINECS: 205-243-8
Classification Code: Analgesic; Drug / Therapeutic Agent; Human Data; Mutation data; Tumor data
Product Categories: Intermediates & Fine Chemicals; Pharmaceuticals
H-Bond Donor: 3
H-Bond Acceptor: 5
Rotatable Bond Count: 2
Tautomer Count: 12
Exact Mass: 249.078123
MonoIsotopic Mass: 249.078123
Topological Polar Surface Area: 89.6
Heavy Atom Count: 17 
Complexity: 237
Flash Point: 221.3 °C 
Enthalpy of Vaporization: 69.97 kJ/mol 
Boiling Point: 442.3 °C at 760 mmHg 
Melting Point: 139 °C
Water Solubility: 0.01-0.1 g/100 mL at 20 °C
Vapour Pressure of Phenazopyridine hydrochloride (CAS NO.136-40-3): 5.1E-08 mmHg at 25 °C

Phenazopyridine hydrochloride Uses

  Phenazopyridine hydrochloride (CAS NO.136-40-3) is used as 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.

Phenazopyridine hydrochloride Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo oral 35mg/kg (35mg/kg) VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION
KIDNEY, URETER, AND BLADDER: HEMATURIA
BLOOD: METHEMOGLOBINEMIA-CARBOXYHEMOGLOBIN		 American Journal of Diseases of Children. Vol. 117, Pg. 369, 1969.
 
child TDLo oral 125mg/kg (125mg/kg) LUNGS, THORAX, OR RESPIRATION: CYANOSIS
BLOOD: METHEMOGLOBINEMIA-CARBOXYHEMOGLOBIN
BLOOD: OTHER HEMOLYSIS WITH OR WITHOUT ANEMIA		 Clinical Pediatrics Vol. 10, Pg. 537, 1971.
 
child TDLo oral 400mg/kg (400mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
LUNGS, THORAX, OR RESPIRATION: CYANOSIS		 American Journal of Diseases of Children. Vol. 110, Pg. 105, 1965.
 
man TDLo oral 86mg/kg/10D-I (86mg/kg) SPINAL CORD: INFLAMMATORY CHANGES Annals of Internal Medicine. Vol. 106, Pg. 164, 1987.
man TDLo oral 114mg/kg (114mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"
KIDNEY, URETER, AND BLADDER: URINE VOLUME DECREASED		 Human Toxicology. Vol. 2, Pg. 539, 1983.
 
mouse LD50 intravenous 180mg/kg (180mg/kg)   U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#04014,
rat LD50 oral 472mg/kg (472mg/kg)   Toxicology and Applied Pharmacology. Vol. 1, Pg. 42, 1959.
rat LDLo intraperitoneal 200mg/kg (200mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
LUNGS, THORAX, OR RESPIRATION: DYSPNEA
LUNGS, THORAX, OR RESPIRATION: STRUCTURAL OR FUNCTIONAL CHANGE IN TRACHEA OR BRONCHI		 Journal of Pharmacology and Experimental Therapeutics. Vol. 51, Pg. 200, 1934.
women TDLo oral 34mg/kg (34mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
KIDNEY, URETER, AND BLADDER: URINE VOLUME DECREASED		 Annals of Internal Medicine. Vol. 72, Pg. 89, 1970.
 
women TDLo oral 140mg/kg (140mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING
BLOOD: NORMOCYTIC ANEMIA		 Canadian Medical Association Journal. Vol. 91, Pg. 756, 1964.

Phenazopyridine hydrochloride Safety Profile

Confirmed carcinogen with experimental carcinogenic and tumorigenic data. A poison by intraperitoneal and intravenous routes. Moderately toxic by ingestion. Human systemic effects by ingestion: somnolence, cyanosis, diarrhea, nausea or vomiting, anuria or decreased urine volume, normocytic anemia, methemoglobinemia-carboxyhemoglobinemia, dehydration, changes in blood sodium levels. Mutation data reported. When heated to decomposition it emits very toxic fumes of NOx and HCl.
Hazard Codes: HarmfulXn,CorrosiveC
Risk Statements: 22-36/37/38-40-34
R22: Harmful if swallowed. 
R36/37/38: Irritating to eyes, respiratory system and skin. 
R34: Causes burns. 
R40: Limited evidence of a carcinogenic effect.
Safety Statements of Phenazopyridine hydrochloride (CAS NO.136-40-3): 26-36/37-45-36/37/39-27 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36/37: Wear suitable protective clothing and gloves. 
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection. 
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S27: Take off immediately all contaminated clothing.

Phenazopyridine hydrochloride Specification

 Phenazopyridine hydrochloride (CAS NO.136-40-3), its Synonyms are 2,6-Diamino-3-(phenylazo)pyridine monohydrochloride ; 2,6-Diamino-3-phenylazopyridine hydrochloride ; 2,6-Pyridinediamine, 3-(phenylazo)-, monohydrochloride ; 3-(Phenylazo)-2,6-pyridinediamine, hydrochloride ; 3-Phenylazo-2,6-diaminopyridine hydrochloride ; Azo-Standard ; Azodyne ; Azomine ; Azosulfisox ; Bisteril ; Phenazodine ; Phenazopyridine HCl ; Phenazopyridinium chloride ; Phenyl-idium ; Pyridine, 2,6-diamino-3-(phenylazo)-, hydrochloride and so on. It is brick-red crystals.

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