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603-50-9

Basic Information
CAS No.: 603-50-9
Name: Phenol,4,4'-(2-pyridinylmethylene)bis-, 1,1'-diacetate
Molecular Structure:
Molecular Structure of 603-50-9 (Phenol,4,4'-(2-pyridinylmethylene)bis-, 1,1'-diacetate)
Formula: C22H19NO4
Molecular Weight: 361.40
Synonyms: Phenol,4,4'-(2-pyridinylmethylene)bis-, diacetate (ester) (9CI);Phenol,4,4'-(2-pyridylmethylene)di-, diacetate (6CI,7CI);Phenol,4,4'-(2-pyridylmethylene)di-, diacetate (ester) (8CI);4,4'-(2-Pyridylmethylene)diphenol diacetate;Bicol;Bis(p-acetoxyphenyl)-2-pyridylmethane;Bisacodyl;Brocalax;Broxalax;Contralax;Correctol Caplets;Dulcolan;Durolax;Eulaxan;Godalax;Hillcolax;Ivilax;Laco;Laxanin N;Laxine;Laxorex;Neolax;Perilax;Prepacol;Pyrilax;SK-Bisacodyl;Ulcol;Zetrax;
EINECS: 210-044-4
Density: 1.2 g/cm3
Melting Point: 138 °C
Boiling Point: 492.333 °C at 760 mmHg
Flash Point: 251.554 °C
Solubility: Soluble in alcohol (slightly), ether (slightly), chloroform, and acetone. Insoluble in water.
Appearance: white crystalline powder
Hazard Symbols: IrritantXi
Risk Codes: 22-36/37/38
Safety: 26-36
Transport Information:
PSA: 65.49000
LogP: 4.11240
Synthetic route
603-41-8

4,4'-(2-pyridylmethylene)diphenol

108-24-7

acetic anhydride

603-50-9

bisacodyl

Conditions
ConditionsYield
With sodium acetate at 100 - 140℃; Temperature; Large scale;95%
With pyridine In dichloromethane at 0 - 20℃; for 2h;88%
With sodium acetate
With pyridine
With sodium acetate
108-24-7

acetic anhydride

78539-92-1

3-(4-methoxyphenyl)-[1,2,3]triazolo[1,5-a]pyridine

159191-56-7

(4-((tert-butyldimethylsilyl)oxy)phenyl)boronic acid

603-50-9

bisacodyl

Conditions
ConditionsYield
Stage #1: 3-(4-methoxyphenyl)-[l,2,3]triazolo[1,5-a]pyridine; (4-((tert-butyldimethylsilyl)oxy)phenyl)boronic acid With potassium carbonate In benzene at 20℃; for 10h; UV-irradiation;
Stage #2: With hydrogen bromide; acetic acid Reflux;
Stage #3: acetic anhydride With triethylamine In dichloromethane at 20℃;
74%
29745-44-6

pyridine-2-carbonyl chloride

603-50-9

bisacodyl

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 8.4 g / triethylamine / CH2Cl2 / 0 - 20 °C
2: 56 percent / AlCl3 / 4 h / 160 °C
3: 94.5 percent / sodium borohydride / methanol / 2 h / 0 - 20 °C
4: 69 percent / H3PO4 / H2O / 0.5 h / 100 °C
5: 88 percent / pyridine / CH2Cl2 / 2 h / 0 - 20 °C
View Scheme
98-98-6

2-Picolinic acid

603-50-9

bisacodyl

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: thionyl chloride / benzene / 12 h / Heating
2: 8.4 g / triethylamine / CH2Cl2 / 0 - 20 °C
3: 56 percent / AlCl3 / 4 h / 160 °C
4: 94.5 percent / sodium borohydride / methanol / 2 h / 0 - 20 °C
5: 69 percent / H3PO4 / H2O / 0.5 h / 100 °C
6: 88 percent / pyridine / CH2Cl2 / 2 h / 0 - 20 °C
View Scheme
26838-86-8

pyridine-2-carboxylic acid phenyl ester

603-50-9

bisacodyl

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 56 percent / AlCl3 / 4 h / 160 °C
2: 94.5 percent / sodium borohydride / methanol / 2 h / 0 - 20 °C
3: 69 percent / H3PO4 / H2O / 0.5 h / 100 °C
4: 88 percent / pyridine / CH2Cl2 / 2 h / 0 - 20 °C
View Scheme
33455-95-7

4-hydroxyphenyl(2-pyridyl) carbinol

603-50-9

bisacodyl

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 69 percent / H3PO4 / H2O / 0.5 h / 100 °C
2: 88 percent / pyridine / CH2Cl2 / 2 h / 0 - 20 °C
View Scheme
33077-70-2

(4-hydroxyphenyl)(pyridin-2-yl)methanone

603-50-9

bisacodyl

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 94.5 percent / sodium borohydride / methanol / 2 h / 0 - 20 °C
2: 69 percent / H3PO4 / H2O / 0.5 h / 100 °C
3: 88 percent / pyridine / CH2Cl2 / 2 h / 0 - 20 °C
View Scheme
108-95-2

phenol

2-chlorobenzylhalide

2-chlorobenzylhalide

603-50-9

bisacodyl

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 69 percent / H3PO4 / H2O / 0.5 h / 100 °C
2: 88 percent / pyridine / CH2Cl2 / 2 h / 0 - 20 °C
View Scheme
1121-60-4

pyridine-2-carbaldehyde

603-50-9

bisacodyl

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: concentrated sulfuric acid
2: sodium acetate
View Scheme
Multi-step reaction with 2 steps
1: aqueous hydrochloric acid; acetic acid
2: sodium acetate
View Scheme
Multi-step reaction with 3 steps
1: hydrogenchloride
2: sulfuric acid; sodium nitrite
3: sodium acetate
View Scheme

bisacodyl

bisacodyl

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sulfuric acid; sodium nitrite
2: sodium acetate
View Scheme
62-53-3

aniline

603-50-9

bisacodyl

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydrogenchloride
2: sulfuric acid; sodium nitrite
3: sodium acetate
View Scheme
108-95-2

phenol

603-50-9

bisacodyl

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: concentrated sulfuric acid
2: sodium acetate
View Scheme
Multi-step reaction with 2 steps
1: aqueous hydrochloric acid; acetic acid
2: sodium acetate
View Scheme
Multi-step reaction with 2 steps
1: sulfuric acid
2: sodium acetate
View Scheme
1121-60-4

pyridine-2-carbaldehyde

108-95-2

phenol

603-50-9

bisacodyl

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sulfuric acid
2: sodium acetate
View Scheme
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    603-50-9

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    603-50-9

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Consensus Reports

Reported in EPA TSCA Inventory.

Standards and Recommendations

ASSAY: 99.0% min
RESIDUE ON IGNITION: 0.1% max
HEAVY METALS: 10ppm max
LOSS ON DRYING: 0.5% max

Specification

The Bisacodyl, with the CAS registry number 603-50-9, is also known as Bis(p-acetoxyphenyl)-2-pyridylmethane. It belongs to the product categories of Active Pharmaceutical Ingredients; Intermediates & Fine Chemicals; Pharmaceuticals. Its EINECS number is 210-044-4. This chemical's molecular formula is C22H19NO4 and molecular weight is 361.40. What's more, its systematic name is (2-Pyridinylmethylene)di-4,1-phenylene diacetate. Its classification codes are: (1)Cathartics; (2)Gastrointestinal Agents; (3)Laxative. It is a stimulant laxative drug that works directly on the large colon to produce a bowel movement. It is typically prescribed for relief of constipation and for the management of neurogenic bowel dysfunction as well as part of bowel preparation before medical examinations.

Physical properties of Bisacodyl are: (1)ACD/LogP: 3.453; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.39; (4)ACD/LogD (pH 7.4): 3.45; (5)ACD/BCF (pH 5.5): 214.64; (6)ACD/BCF (pH 7.4): 247.54; (7)ACD/KOC (pH 5.5): 1558.81; (8)ACD/KOC (pH 7.4): 1797.78; (9)#H bond acceptors: 5; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 7; (12)Polar Surface Area: 65.49 Å2; (13)Index of Refraction: 1.584; (14)Molar Refractivity: 100.741 cm3; (15)Molar Volume: 301.156 cm3; (16)Polarizability: 39.937×10-24cm3; (17)Surface Tension: 46.97 dyne/cm; (18)Density: 1.2 g/cm3; (19)Flash Point: 251.554 °C; (20)Enthalpy of Vaporization: 75.924 kJ/mol; (21)Boiling Point: 492.333 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

When you are using this chemical, please be cautious about it as the following:
This chemical is harmful if swallowed. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need wear suitable protective clothing.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(Oc1ccc(cc1)C(c2ccc(OC(=O)C)cc2)c3ncccc3)C
(2)Std. InChI: InChI=1S/C22H19NO4/c1-15(24)26-19-10-6-17(7-11-19)22(21-5-3-4-14-23-21)18-8-12-20(13-9-18)27-16(2)25/h3-14,22H,1-2H3
(3)Std. InChIKey: KHOITXIGCFIULA-UHFFFAOYSA-N

The toxicity data is as follows:  

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo intravenous 40mg/kg (40mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 3, Pg. 19, 1953.
dog LD50 oral > 15gm/kg (15000mg/kg)   Drugs in Japan Vol. -, Pg. 854, 1990.
dog LDLo intravenous 40mg/kg (40mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 3, Pg. 19, 1953.
mouse LD50 oral 17500mg/kg (17500mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

BEHAVIORAL: ATAXIA

BLOOD: HEMORRHAGE
Toxicology and Applied Pharmacology. Vol. 2, Pg. 243, 1960.
mouse LDLo intravenous 80mg/kg (80mg/kg)   Toxicology and Applied Pharmacology. Vol. 2, Pg. 243, 1960.
rabbit LDLo intravenous 40mg/kg (40mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 3, Pg. 19, 1953.
rat LD50 oral 4320mg/kg (4320mg/kg) BLOOD: CHANGES IN SPLEEN

GASTROINTESTINAL: OTHER CHANGES

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)
Toxicology and Applied Pharmacology. Vol. 2, Pg. 243, 1960.