603-41-8

Usage

Uses

Used in Pharmaceutical Industry:
p,p'-(2-Pyridylmethylene)bisphenol is used as an active pharmaceutical ingredient (API) for its cathartic properties. As the active form of Bisacodyl, it acts as a stimulant laxative, promoting bowel movements and relieving constipation. Its effectiveness in treating gastrointestinal disorders and promoting regular bowel function makes it a valuable component in the development of pharmaceutical products.
Used in Chemical Synthesis:
In the field of organic chemistry, p,p'-(2-pyridylmethylene)bisphenol serves as a key intermediate in the synthesis of various complex organic molecules. Its unique structure allows for further functionalization and modification, making it a versatile building block for the creation of novel compounds with potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science.
Used in Material Science:
Due to its structural properties, p,p'-(2-pyridylmethylene)bisphenol can be utilized in the development of advanced materials with specific characteristics. For instance, it can be incorporated into the synthesis of polymers, resins, and coatings, where its unique chemical properties can contribute to enhanced performance, such as improved thermal stability, mechanical strength, or chemical resistance.
Used in Research and Development:
As a novel compound with unique structural features, p,p'-(2-pyridylmethylene)bisphenol holds potential for further research and development. It can be employed as a model compound to study various chemical reactions, mechanisms, and interactions with other molecules. This can lead to a better understanding of its properties and the discovery of new applications in various fields.

Synthetic route

3,3'-dichloro-4,4'-(pyridin-2-ylmethylene)diphenol → 4,4'-(2-pyridylmethylene)diphenol (603-41-8)

Conditions	Yield
With nickel aluminum; sodium hydroxide at 20℃; for 9h; Concentration;	95.7%

bisacodyl (603-50-9) → 4,4'-(2-pyridylmethylene)diphenol (603-41-8)

Conditions	Yield
With potassium hydroxide In ethanol; water at 20℃; for 72h;	92%
With sodium hydroxide In water; acetonitrile at 50℃; for 5h; Temperature;	10.99 g

3-(4-methoxyphenyl)-[1,2,3]triazolo[1,5-a]pyridine (78539-92-1) + (4-((tert-butyldimethylsilyl)oxy)phenyl)boronic acid (159191-56-7) → 4,4'-(2-pyridylmethylene)diphenol (603-41-8)

Conditions	Yield
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;	80%

pyridine-2-carbaldehyde (1121-60-4) + phenol (108-95-2) → 4,4'-(2-pyridylmethylene)diphenol (603-41-8)

Conditions	Yield
With sulfuric acid at 0 - 20℃; for 3h;	71.1%
Stage #1: phenol With sulfuric acid; alpha cyclodextrin at 20℃; Large scale; Stage #2: pyridine-2-carbaldehyde Large scale;	59.4%
With sulfuric acid

4-hydroxyphenyl(2-pyridyl) carbinol (33455-95-7) + phenol (108-95-2) → 4,4'-(2-pyridylmethylene)diphenol (603-41-8)

Conditions	Yield
With phosphoric acid In water at 100℃; for 0.5h;	69%

4,4'-(pyridin-2-ylmethylene)dianiline (85171-91-1) → 4,4'-(2-pyridylmethylene)diphenol (603-41-8)

Conditions	Yield
With sulfuric acid; sodium nitrite

di[4'',4'''-di(methoxy)phenyl](2'-pyridyl)methanol (67916-54-5) → 4,4'-(2-pyridylmethylene)diphenol (603-41-8)

Conditions	Yield
With hydrogen iodide
With hydrogen iodide; acetic acid at 100℃; for 6h; Reagent/catalyst; Large scale;	1.6 kg

bis-(4-methoxy-phenyl)-[2]pyridyl-acetonitrile (94871-89-3) → 4,4'-(2-pyridylmethylene)diphenol (603-41-8)

Conditions	Yield
With hydrogen bromide Erwaermen des Reaktionsprodukts mit wss.Kalilauge;

2-diethoxymethyl-pyridine (27443-37-4) + phenol (108-95-2) → 4,4'-(2-pyridylmethylene)diphenol (603-41-8)

Conditions	Yield
With sulfuric acid
With sulfuric acid

phenol (108-95-2) + sodium-salt of/the/ hydroxy-<2>pyridyl-methanesulfonic acid → 4,4'-(2-pyridylmethylene)diphenol (603-41-8)

Conditions	Yield
With sulfuric acid
With sulfuric acid

pyridine-2-carbonyl chloride (29745-44-6) → 4,4'-(2-pyridylmethylene)diphenol (603-41-8)

Conditions	Yield
Multi-step reaction with 4 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 View Scheme

2-Picolinic acid (98-98-6) → 4,4'-(2-pyridylmethylene)diphenol (603-41-8)

Conditions	Yield
Multi-step reaction with 5 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 View Scheme

pyridine-2-carboxylic acid phenyl ester (26838-86-8) → 4,4'-(2-pyridylmethylene)diphenol (603-41-8)

Conditions	Yield
Multi-step reaction with 3 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 View Scheme

(4-hydroxyphenyl)(pyridin-2-yl)methanone (33077-70-2) → 4,4'-(2-pyridylmethylene)diphenol (603-41-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 94.5 percent / sodium borohydride / methanol / 2 h / 0 - 20 °C 2: 69 percent / H3PO4 / H2O / 0.5 h / 100 °C View Scheme

pyridine-2-carbaldehyde (1121-60-4) → 4,4'-(2-pyridylmethylene)diphenol (603-41-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogenchloride 2: sulfuric acid; sodium nitrite View Scheme

2-pyridyllithium (17624-36-1) → 4,4'-(2-pyridylmethylene)diphenol (603-41-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: diethyl ether / -65 - -40 °C 2: aqueous hydriodic acid View Scheme

bis(p-methoxyphenyl)methanone (90-96-0) → 4,4'-(2-pyridylmethylene)diphenol (603-41-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: diethyl ether / -65 - -40 °C 2: aqueous hydriodic acid View Scheme

aniline (62-53-3) → 4,4'-(2-pyridylmethylene)diphenol (603-41-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogenchloride 2: sulfuric acid; sodium nitrite View Scheme

1-bromo-4-methoxy-benzene (104-92-7) → 4,4'-(2-pyridylmethylene)diphenol (603-41-8)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: magnesium / tetrahydrofuran / 1 h / 20 - 65 °C / Inert atmosphere; Large scale 1.2: 4 h / 10 - 20 °C / Inert atmosphere; Large scale 2.1: hydrogen iodide; acetic acid / 6 h / 100 °C / Large scale View Scheme

ethyl-2-picolinate (2524-52-9) → 4,4'-(2-pyridylmethylene)diphenol (603-41-8)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: magnesium / tetrahydrofuran / 1 h / 20 - 65 °C / Inert atmosphere; Large scale 1.2: 4 h / 10 - 20 °C / Inert atmosphere; Large scale 2.1: hydrogen iodide; acetic acid / 6 h / 100 °C / Large scale View Scheme

Guttalax (10040-45-6) → 4-((4-hydroxyphenyl)(pyridin-2-yl)methyl)phenyl hydrogen sulfate (51264-33-6) + 4,4'-(2-pyridylmethylene)diphenol (603-41-8)

Conditions	Yield
With water at 40℃; for 730.5h;

Guttalax (10040-45-6) → 4-((4-hydroxyphenyl)(pyridin-2-yl)methyl)phenyl hydrogen sulfate (51264-33-6) + 4,4'-(2-pyridylmethylene)diphenol (603-41-8) + (hydroxy(pyridin-2-yl)methylene)bis(4,1-phenylene) bis(sulfate)

Conditions	Yield
With water at 40℃; for 4383h; Temperature;

4,4'-(2-pyridylmethylene)diphenol (603-41-8) + acetic anhydride (108-24-7) → bisacodyl (603-50-9)

Conditions	Yield
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

4,4'-(2-pyridylmethylene)diphenol (603-41-8) → Guttalax (10040-45-6)

Conditions	Yield
Stage #1: 4,4'-(2-pyridylmethylene)diphenol With pyridine; chlorosulfonic acid at 0 - 20℃; for 5h; Stage #2: With sodium hydroxide Concentration; Cooling with ice;	86.4%
Stage #1: 4,4'-(2-pyridylmethylene)diphenol With pyridine; chlorosulfonic acid at 10 - 25℃; for 12h; Inert atmosphere; Large scale; Stage #2: With water; sodium hydroxide at 0℃; pH=11; pH-value; Inert atmosphere; Large scale;	2.1 kg

4,4'-(2-pyridylmethylene)diphenol (603-41-8) + 8-tosyloxy-3,6-dioxaoctanol (77544-68-4) → 2,2′-(((((((pyridin-2-ylmethylene)bis(4,1-phenylene))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))diethanol

Conditions	Yield
Stage #1: 4,4'-(2-pyridylmethylene)diphenol With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 1h; Inert atmosphere; Stage #2: 8-tosyloxy-3,6-dioxaoctanol In N,N-dimethyl-formamide at 80℃; for 96h; Inert atmosphere;	70%

4,4'-(2-pyridylmethylene)diphenol (603-41-8) + 5-tosyloxy-3-oxapentanol (118591-58-5) → 2,2′-(((((pyridin-2-ylmethylene)bis(4,1-phenylene))bis(oxy))bis(ethane-2,1-diyl))bis(oxy)) diethanol

Conditions	Yield
Stage #1: 4,4'-(2-pyridylmethylene)diphenol With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 1h; Inert atmosphere; Stage #2: 5-tosyloxy-3-oxapentanol In N,N-dimethyl-formamide at 80℃; for 96h; Inert atmosphere;	60%

4,4'-(2-pyridylmethylene)diphenol (603-41-8) + p-toluenesulfonic acid 2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethyl ester (77544-60-6) → 2,2′-(((((((((pyridin-2-ylmethylene)bis(4,1-phenylene))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))diethanol

Conditions	Yield
Stage #1: 4,4'-(2-pyridylmethylene)diphenol With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 1h; Inert atmosphere; Stage #2: p-toluenesulfonic acid 2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethyl ester In N,N-dimethyl-formamide at 80℃; for 96h; Inert atmosphere;	50%

4,4'-(2-pyridylmethylene)diphenol (603-41-8) + 2-bromoethanol (540-51-2) → 2,2′-(((pyridin-2-ylmethylene)bis(4,1-phenylene))bis(oxy))diethanol + 4-((4-(2-hydroxyethoxy)phenyl)(pyridin-2-yl)methyl)phenol

Conditions	Yield
Stage #1: 4,4'-(2-pyridylmethylene)diphenol With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 0.5h; Inert atmosphere; Stage #2: 2-bromoethanol With potassium iodide In N,N-dimethyl-formamide at 80℃; for 96h; Inert atmosphere;	A 15% B 50%

4,4'-(2-pyridylmethylene)diphenol (603-41-8) + 2-[2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethoxy]ethyl 4-methylbenzenesulfonate (155130-15-7) → 14,14′-(((pyridin-2-ylmethylene)bis(4,1-phenylene))bis(oxy))bis(3,6,9,12-tetraoxatetradecan-1-ol)

Conditions	Yield
Stage #1: 4,4'-(2-pyridylmethylene)diphenol With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 1h; Inert atmosphere; Stage #2: 2-[2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethoxy]ethyl 4-methylbenzenesulfonate In N,N-dimethyl-formamide at 80℃; for 96h; Inert atmosphere;	45%

4,4'-(2-pyridylmethylene)diphenol (603-41-8) + dimethyl sulfate (77-78-1) → 2-(4,4'-dihydroxy-benzhydryl)-1-methyl-pyridinium; methyl sulfate

Conditions	Yield
With tetrahydrofuran

4,4'-(2-pyridylmethylene)diphenol (603-41-8) → 2-(4,4'-dihydroxy-benzhydryl)-piperidine

Conditions	Yield
With acetic acid; platinum at 40℃; Hydrogenation;
With ethanol; nickel at 100℃; under 73550.8 Torr; Hydrogenation;

4,4'-(2-pyridylmethylene)diphenol (603-41-8) + allyl bromide (106-95-6) → C24H23NO2

Conditions	Yield
With potassium carbonate In acetone

4,4'-(2-pyridylmethylene)diphenol (603-41-8) → C24H23NO2

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / acetone 2: BCl3 / CH2Cl2 View Scheme

Upstream product

• 1121-60-4 pyridine-2-carbaldehyde 
• 108-95-2 phenol 
• 85171-91-1 4,4'-(pyridin-2-ylmethylene)dianiline 
• 67916-54-5 di[4'',4'''-di(methoxy)phenyl](2'-pyridyl)methanol 
• 94871-89-3 bis-(4-methoxy-phenyl)-[2]pyridyl-acetonitrile 
• 27443-37-4 2-diethoxymethyl-pyridine 
• 33455-95-7 4-hydroxyphenyl(2-pyridyl) carbinol 
• 29745-44-6 pyridine-2-carbonyl chloride 
• 98-98-6 2-Picolinic acid 
• 26838-86-8 pyridine-2-carboxylic acid phenyl ester 
• 33077-70-2 (4-hydroxyphenyl)(pyridin-2-yl)methanone 
• 17624-36-1 2-pyridyllithium 
• 90-96-0 bis(p-methoxyphenyl)methanone 
• 62-53-3 aniline 

Downstream Products

• 603-50-9 bisacodyl 
• 10040-45-6 Guttalax 

Relevant academic research and scientific papers

Preparation method of bisacodyl

The present invention provides the preparation method shown in formula I., the preparation method of bisacodyl. The present invention provides a new method for the preparation of bisacodyl.

Preparation method of sodium picosulfate

The invention belongs to the technical field of medicines, and relates to a preparation method of sodium picosulfate, in particular to condensation of pyridine -2 - formaldehyde and phenol under an acidic condition, and the obtained intermediate 4,4 ' - (2 - pyridinmethylene) - bisphenol uses sulfamic acid as a sulfonating agent. The method is relatively simple in process operation and high in sample purity.

Method for preparing high-purity sodium picosulfate intermediate and sodium picosulfate

The invention discloses a method for preparing high-purity sodium picosulfate and an intermediate thereof. The method comprises the following steps: (1) dropwise adding concentrated sulfuric acid and 2-pyridylaldehyde into an acetonitrile solution of phenol in sequence for reaction; (2) adjusting to be alkaline after reaction quenching, neutralizing, dispersing and crystallizing, and refining a crude product by using organic alcohol; (3) adding the intermediate into a pyridine solution of chlorosulfonic acid, washing off pyridine by using acetone after the reaction is finished, treating into sodium salt by using an alkali, concentrating until dryness, extracting by using hot methanol, adding ethyl acetate for crystallization, filtering and drying to obtain a sodium picosulfate crude product; and (4) thermally extracting the crude product with absolute ethyl alcohol, adding a proper amount of purified water, cooling and crystallizing to obtain the sodium picosulfate monohydrate. According to the method, the high-purity intermediate and the sodium picosulfate monohydrate can be stably obtained by controlling the content of the isomer in the intermediate.

Colloidal gold detection kit for sodium picosulfate, bisacodyl and deacetylated bisacodyl and application of colloidal gold detection kit

The invention discloses a novel compound. By adopting the compound, the recognition sensitivity and specificity of sodium picosulfate, bisacodyl and deacetylated bisacodyl can be improved. A chromatographic immune colloidal gold principle is applied, the compounds are made into antigens, a detection device is further formed, the detection device comprises a test strip and a reaction cup, and a detection line and a quality control line in the test strip are used for semi-quantitative detection of the content of sodium picosulfate, bisacodyl and deacetylated bisacodyl in a sample through line colorimetry. According to the invention, whether a sample contains sodium picosulfate, bisacodyl and deacetylated bisacodyl or not can be rapidly and accurately detected within a short time, the detection requirement of illegally adding sodium picosulfate, bisacodyl and deacetylated bisacodyl in weight-losing products can be met, and the requirement of on-site supervision and law enforcement of supervision departments and detection institutions can be met. Compared with the prior art, the kit has the characteristics of convenience in use, economy, quickness, easiness in manufacturing and low cost.

Synthesis method of sodium picosulfate

The method comprises the following steps: adding acridine to an organic solvent, adding basic substances for reaction, adjusting pH values, filtering to obtain 4 and 4' - (2 -pyridylmethyl) bisphenol. 4, 4' - (2 - Picoline) bisphenol was added to the reaction solvent, a basic substance was added, and then a sulfonating reagent was added for the reaction. After the completion of the reaction, the crude product is obtained by quenching, extraction, concentration and recrystallization. The crude product was recrystallized from sodium sulfate to give a qualified sodium sulfate product. The method has the advantages that the process route is simple, the operation is simpler, the yield is increased and the like, the purity of the intermediate produced by the method is high, and the sodium metabisulfite meeting the requirements of the pharmacopeia can be easily obtained to solve the defects caused by the prior art.

Preparation and application of broad-spectrum antibody for simultaneously detecting three illegal additives in weight-losing health food

The invention discloses a preparation method and application of a broad-spectrum antibody for simultaneous detection. The invention firstly provides two haptens, namely a hapten 1 and a hapten 2, wherein the structural formula of the hapten 1 is shown as a formula (I); and the structural formula of the hapten 2 is shown as a formula (III). According to the present invention, the hapten 1 is used to prepare the antibody for simultaneously detecting the three illegal additives in the weight-losing health food, the hapten 2 is used to prepare an artificial antigen 2 for coating, and the antibody has high sensitivity and high specificity on the three illegal additives in the weight-losing health food so as to meet the detection limit required by market supervision; meanwhile, an immunoassay method which is low in cost, high in sensitivity and stable and is used for simultaneously detecting three illegal additives in the weight-losing health-care food is established, and the immunoassay method has a good application prospect.

Pegylated triarylmethanes: Synthesis, antimicrobial activity, anti-proliferative behavior and in silico studies

We describe herein the synthesis, characterization and biological studies of novel PEGylated triarylmethanes. Non-symmetrical and symmetrical triarylmethanes series have been synthesized by Friedel-Crafts hydroxyalkylation or directly from bisacodyl respectively followed by a functionalization with PEG fragments in order to increase bioavailability and biological effectiveness. The antimicrobial activity was investigated against Gram-positive and Gram-negative foodborne pathogens and against Candida albicans, an opportunistic pathogenic yeast. The anti-biocidal activity was also studied using Staphylococcus aureus as a reference bacterium. Almost all PEGylated molecules displayed an antifungal activity comparable with fusidic acid with MIC values ranging from 6.25 to 50 μg/mL. Compounds also revealed a promising antibiofilm activity with biofilm eradication percentages values above 80% for the best molecules (compounds 4d and 7). Compounds 7 and 8b showed a modest antiproliferative activity against human colorectal cancer cell lines HT-29. Finally, in silico molecular docking studies revealed DHFR and DNA gyrase B as potential anti-bacterial targets and in silico predictions of ADME suggested adequate drug-likeness profiles for the synthetized triarylmethanes.

Hapten BIS for rapidly detecting bisacodin, artificial antigen, antibody of artificial antigen and detection method

The invention discloses a hapten BIS for rapidly detecting bisacodin, an artificial antigen, an antibody of the artificial antigen and a detection method. The invention firstly provides a hapten BIS for detecting bisacodin, and the structural formula of the hapten BIS is shown as a formula (I): an artificial antigen and an antibody for detecting bisacodin are prepared by using the hapten, the antibody has high sensitivity and high specificity recognition capability compared with bisacodin, the detection range of the antibody is 0.09-4.92 mu g/kg, and the lowest detection limit is 0.07 mu g/kg.Therefore, the bisacodin antibody prepared by the invention is high in detection sensitivity and strong in specificity in comparison with sacodin, and can meet the field detection requirements of large-batch samples; in addition, the hapten BIS, the artificial antigen and the antibody are simple in preparation method and low in cost, and have wide application prospects in detection of bisacodin.

Light-induced metal-free transformations of unactivated pyridotriazoles

A highly efficient and practical method for incorporation of the arylmethylpyridyl moiety into diverse molecules has been developed. This method features the transition metal-free light-induced room temperature transformation of pyridotriazoles into pyridyl carbenes, which are capable of smooth arylation, X-H insertion, and cyclopropanation reactions. The synthetic usefulness of the developed method was illustrated in a facile synthesis of biologically active molecules.

A process for preparing sodium new method (by machine translation)

The invention relates to a method for preparing (V) indicated by the sodium of the method, the method comprises the following steps: (a) in formula (I) indicated by the 2 - picolinic ester as the starting material, as shown in formula (II) of 4 - halogenated phenyl ether in the formula (III) Grignard reaction indicated by the 4', 4" - dialkoxy diphenyl - (2 - pyridine) - methanol (compound III). (B) 4 ', 4 "- dialkoxy diphenyl - (2 - pyridine) - methanol (compound III) in the Lewis acid under the action of removing a water molecule and alkoxy alkyl, formula (IV) as shown by a 4', 4" - dihydroxy phenyl - (2 - pyridine) - methane (compound IV). (C) 4', 4" - dihydroxy phenyl - (2 - pyridine) - methane with chlorosulfuric acid in sulfuric acid esterification reaction, sodium hydroxide after treatment, to obtain crude sodium, by recrystallization to obtain high-purity sodium (compound V). The present invention provides a kind of existing technology with the different sodium new preparation method, the method is simple in operation, the atom economy is high, is suitable for industrial production. (by machine translation)