1193-24-4

Basic information

• Product Name: 4,6-Dihydroxypyrimidine
• Synonyms: NSC 22838;4,6-DIHYDROXYPYRIMIDINE FOR SYNTHESIS;4,6-Dihydroxypyrimidine, 4,6-Dihydroxy-1,3-diazine;4,6- twohydroxy pyriMidine;4, 6-2 hydroxy pyriMidine;DihydroxypyriMidine;4,6-PYRIMIDINEDIOL;4,6-DIHYDROXYPYRIMIDINE
• CAS NO: 1193-24-4
• Molecular Formula: C₄H₄N₂O₂
• Molecular Weight: 112.09
• EINECS: 214-772-3
• Product Categories: Building Blocks;C4 to C5;Chemical Synthesis;Heterocyclic Building Blocks;Heterocycle-Pyrimidine series;PYRIMIDINE;FINE Chemical & INTERMEDIATES;APIs & Intermediate;Nucleotides and Nucleosides;Pyrimidines;Bases & Related Reagents;Nucleotides
• Mol File: 1193-24-4.mol
• Article Data: 15

Chemical Properties

• Melting Point: >300 °C(lit.)
• Boiling Point: 209.98°C (rough estimate)
• Flash Point: 170.6 °C
• Appearance: Yellow to orange/Powder
• Density: 1.4421 (rough estimate)
• Vapor Pressure: 0.001Pa at 20℃
• Refractive Index: 1.4610 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: 2.5 g/L (20° C)
• PKA: 5.70±0.10(Predicted)
• Water Solubility: 2.5 g/L (20 º C)
• BRN: 606433
• CAS DataBase Reference: 4,6-Dihydroxypyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 4,6-Dihydroxypyrimidine(1193-24-4)
• EPA Substance Registry System: 4,6-Dihydroxypyrimidine(1193-24-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 1
• RTECS: UW7523000
• TSCA: Yes
• Hazardous Substances Data: 1193-24-4(Hazardous Substances Data)

Usage

Description

4,6-Dihydroxypyrimidine, with the CAS number 1193-24-4, is a light yellow powder that serves as a versatile compound in the realm of organic synthesis. Its unique chemical structure allows it to be a valuable building block for the creation of various complex molecules and pharmaceuticals.

Uses

Used in Organic Synthesis:
4,6-Dihydroxypyrimidine is used as a synthetic building block for the development of a wide range of organic compounds. Its chemical properties make it suitable for use in the synthesis of various molecules, including pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4,6-Dihydroxypyrimidine is used as a key intermediate in the synthesis of various therapeutic agents. Its unique structure allows for the development of novel drugs with potential applications in treating a variety of diseases and medical conditions.
Used in Agrochemical Industry:
4,6-Dihydroxypyrimidine also finds application in the agrochemical industry, where it is used as a starting material for the synthesis of various agrochemicals, such as pesticides and herbicides. Its versatility in organic synthesis enables the development of new and effective products for agricultural use.
Used in Research and Development:
Due to its unique chemical properties, 4,6-Dihydroxypyrimidine is also utilized in research and development laboratories for the exploration of new chemical reactions and the synthesis of novel compounds. Its light yellow powder form makes it easy to handle and manipulate in various chemical processes.

Flammability and Explosibility

Notclassified

Synthesis

Synthesis of 4,6-dihydroxypyrimidine (DHP) by reaction of a malonic acid ester with formamide and an alkali metal alkoxide at elevated temperature.

InChI:InChI=1/C4H4N2O2/c7-3-1-4(8)6-2-5-3/h1-2H,(H2,5,6,7,8)

Synthetic route

malonic acid dimethyl ester (108-59-8) → 4,6-pyrimidinediol (1193-24-4)

Conditions	Yield
With sulfuric acid; sodium methylate; formamide In methanol; water	96%
With hydrogenchloride	76%
With hydrogenchloride; sodium methylate; formamide In methanol; water	75.1%
In water	74.8%

formamide (77287-34-4, 77287-35-5, 60100-09-6) + malonic acid dimethyl ester (108-59-8) → 4,6-pyrimidinediol (1193-24-4)

Conditions	Yield
With sodium methylate In methanol at 60 - 70℃; for 8h; Large scale;	90%
Stage #1: formamide; malonic acid dimethyl ester With sodium methylate In methanol at 95℃; for 1h; Stage #2: With hydrogenchloride In water at 35℃; pH=2.8; Temperature; pH-value; Reagent/catalyst; Solvent;	82.5%
With sodium methylate In methanol at 50℃; for 2h; Concentration; Temperature;

formamide (77287-34-4, 77287-35-5, 60100-09-6) + diethyl malonate (105-53-3) → 4,6-pyrimidinediol (1193-24-4)

Conditions	Yield
With methanol; sodium methylate for 3h; Reflux;	85%
With sodium ethanolate In ethanol at 65 - 110℃; for 49h;	82%
Stage #1: formamide With sodium In ethanol at 45℃; for 10h; Stage #2: diethyl malonate In ethanol at 65 - 110℃; for 4h;	67.9%

formamidine acetic acid (3473-63-0) + malonic acid dimethyl ester (108-59-8) → 4,6-pyrimidinediol (1193-24-4)

Conditions	Yield
Stage #1: formamidine acetic acid With sodium methylate In methanol at 0℃; for 0.0833333h; Inert atmosphere; Stage #2: malonic acid dimethyl ester In methanol at 0℃; for 5h; Reflux;	62%

sodium ethanolate (141-52-6) + diethyl malonate (105-53-3) + formamidine (463-52-5) → 4,6-pyrimidinediol (1193-24-4)

Conditions	Yield
reagiert analog mit Propionamidin;

azoxystrobin (215934-32-0, 131860-33-8) → C21H15N3O5 + 2-(2-(6-(2-cyanophenoxy)pyrimidin-4-yloxy)phenyl)acetic acid methyl ester + methyl (E)-2-[2-[6-(2-cyanophenoxy)pyrimidin-4-yl]oxyphenyl]-3-methoxyprop-2-enoate + 4,6-pyrimidinediol (1193-24-4)

Conditions	Yield
In methanol; water at 19℃; Quantum yield; Further Variations:; pH-values; UV-irradiation;
In methanol; water at 19℃; Quantum yield; Irradiation;

malonodiamide (108-13-4) + formic acid ethyl ester (109-94-4) → 4,6-pyrimidinediol (1193-24-4)

Conditions	Yield
With sodium ethanolate In ethanol Reflux;

acetamidine (143-37-3) + diethyl malonate (105-53-3) → 4,6-pyrimidinediol (1193-24-4)

Conditions	Yield
With sodium methylate In methanol at 0 - 25℃; for 18h;

Upstream product

• 141-52-6 sodium ethanolate 
• 105-53-3 diethyl malonate 
• 463-52-5 formamidine 
• 215934-32-0 azoxystrobin 
• 108-59-8 malonic acid dimethyl ester 
• 77287-34-4 formamide 
• 108-13-4 malonodiamide 
• 109-94-4 formic acid ethyl ester 
• 143-37-3 acetamidine 
• 289-95-2 PYRIMIDINE 
• 3473-63-0 formamidine acetic acid 
• 1193-24-4 6-hydroxy-3,4-dihydropyrimidin-4-one 

Downstream Products

• 138918-23-7 4,6-dihydroxy-5-benzylthiopyrimidine 
• 141764-36-5 5-phenylfuro<2,3-d>pyrimidin-4(3H)-one 
• 141764-35-4 5,6-dihydro-6-nitro-5-phenylfuro<2,3-d>pyrimidin-4(3H)one 
• 141764-46-7 5-(4-chlorophenyl)furo[2,3-d]pyrimidin-4(3H)-one 
• 141764-39-8 (5S,6S)-5-(4-Chloro-phenyl)-6-nitro-5,6-dihydro-3H-furo[2,3-d]pyrimidin-4-one 
• 141764-44-5 5-(2-Chloro-phenyl)-3H-furo[2,3-d]pyrimidin-4-one 
• 141764-37-6 (5R,6S)-5-(2-Chloro-phenyl)-6-nitro-5,6-dihydro-3H-furo[2,3-d]pyrimidin-4-one 
• 141764-45-6 5-(3-Chloro-phenyl)-3H-furo[2,3-d]pyrimidin-4-one 
• 141764-38-7 (5S,6S)-5-(3-Chloro-phenyl)-6-nitro-5,6-dihydro-3H-furo[2,3-d]pyrimidin-4-one 
• 141764-49-0 5-(4-methoxyphenyl)furo[2,3-d]pyrimidin-4(3H)-one 
• 141764-42-3 (5S,6S)-5-(4-Methoxy-phenyl)-6-nitro-5,6-dihydro-3H-furo[2,3-d]pyrimidin-4-one 
• 141764-42-3 (5S,6R)-5-(4-Methoxy-phenyl)-6-nitro-5,6-dihydro-3H-furo[2,3-d]pyrimidin-4-one 
• 141764-48-9 5-(3-Methoxy-phenyl)-3H-furo[2,3-d]pyrimidin-4-one 
• 141764-41-2 (5S,6S)-5-(3-Methoxy-phenyl)-6-nitro-5,6-dihydro-3H-furo[2,3-d]pyrimidin-4-one 

Relevant articles and documents

Sustainable and cost-efficient electro-synthesis of formamidine acetate from cyanamide in aqueous acidic electrolyte

Formamidine represents a versatile building block in synthetic organic chemistry. We developed a new electrochemical synthesis of formamidine acetate by cathodic reduction of cyanamide in an aqueous electrolyte and in high yield. The crude product could be used for further conversions, such as to pyrimidines without purification. Compared to established synthetic routes neither prior processing of cyanamide was necessary, nor precious transition-metal catalyst were required, nor any reagent waste was produced, and only biocompatible and sustainable solvents were employed for this process, following the requirements ofgreen chemistry.

Photochemical transformation of azoxystrobin in aqueous solutions

The photochemical behaviour of azoxystrobin fungicide (AZX) in water was studied under laboratory conditions. Photodegradation was initiated using a solar simulator (xenon arc lamp) or a jacketed Pyrex reaction cell equipped with a 125 W, high-pressure mercury lamp. HPLC/MS analysis (APCI and ESI in positive and negative modes) was used to identify AZX photoproducts. The calculated polychromatic quantum efficiencies (φ{symbol}) of AZX at pH 4.5, 7 and 9 were 5.42 × 10-3, 3.47 × 10-3 and 3.06 × 10-3 (degraded molecules per absorbed photon), respectively. The relatively narrow range of values indicates the stability of AZX with respect to photodegradation in the studied pH range. Results from the HPLC/MS analysis suggest that the phototransformation of AZX proceeds via multiple, parallel reaction pathways including: (1) photo-isomerization (E → Z), (2) photo-hydrolysis of the methyl ester and of the nitrile group, (3) cleavage of the acrylate double bond, (4) photohydrolytic ether cleavage between the aromatic ring giving phenol, and (5) oxidative cleavage of the acrylate double bond.

Preparation method of 4, 6-dihydroxypyrimidine

The invention provides a preparation method of 4, 6-dihydroxypyrimidine. The preparation method comprises the steps of carrying out a first-stage reaction, recovering reaction byproducts, carrying outa second-stage reaction, carrying out dissolving, recovering a solvent, and carrying out adsorbing. According to the preparation method, the raw materials comprise diester malonate, formamide and analkali metal alcoholate solution, and the mass content of the alkali metal alcoholate in the alkali metal alcoholate solution is 30%-50%. The preparation process of the 4, 6-dihydroxypyrimidine is a process of recovering a solvent by adopting normal-pressure reaction and negative-pressure distillation, and positive-pressure operation is avoided in the whole process on the premise of ensuring the yield and quality of the product, so that the preparation process is simple and easy to implement, and industrial production is easy to realize. According to the invention, a suitable sodium methoxideconcentration is selected according to the specific ratio relationship of dimethyl malonate, formamide and sodium methoxide, such that the material consumption is further reduced and the product yieldis improved on the premise of ensuring qualified product quality.