Product Name

  • Name

    4,6-Dihydroxypyrimidine

  • EINECS 214-772-3
  • CAS No. 1193-24-4
  • Article Data27
  • CAS DataBase
  • Density 1.4421 (rough estimate)
  • Solubility 2.5 g/L (20 °C)
  • Melting Point >300 °C(lit.)
  • Formula C4H4N2O2
  • Boiling Point 358.5 °C at 760 mmHg
  • Molecular Weight 112.088
  • Flash Point 170.6 °C
  • Transport Information
  • Appearance pale yellow crystals
  • Safety 26-36-37/39
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 1193-24-4 (4,6-Dihydroxypyrimidine)
  • Hazard Symbols IrritantXi
  • Synonyms 6-hydroxy-1H-pyrimidin-4-one;4,6-Dihydroxypyrimidine(DHP);4 (1H)-Pyrimidinone, 6-hydroxy-;4(3H)-Pyrimidinone, 6-hydroxy-;6-hydroxy-3H-pyrimidin-4-one;4,6-Pyrimidinediol;4,6-Dihydroxy pyrimidine 98%;
  • PSA 66.24000
  • LogP -0.11220

Synthetic route

malonic acid dimethyl ester
108-59-8

malonic acid dimethyl ester

4,6-pyrimidinediol
1193-24-4

4,6-pyrimidinediol

Conditions
ConditionsYield
With sulfuric acid; sodium methylate; formamide In methanol; water96%
With hydrogenchloride76%
With hydrogenchloride; sodium methylate; formamide In methanol; water75.1%
In water74.8%
malonic acid dimethyl ester
108-59-8

malonic acid dimethyl ester

4,6-pyrimidinediol
1193-24-4

4,6-pyrimidinediol

Conditions
ConditionsYield
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;
diethyl malonate
105-53-3

diethyl malonate

4,6-pyrimidinediol
1193-24-4

4,6-pyrimidinediol

Conditions
ConditionsYield
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

formamidine acetic acid

malonic acid dimethyl ester
108-59-8

malonic acid dimethyl ester

4,6-pyrimidinediol
1193-24-4

4,6-pyrimidinediol

Conditions
ConditionsYield
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

sodium ethanolate

diethyl malonate
105-53-3

diethyl malonate

formamidine
463-52-5

formamidine

4,6-pyrimidinediol
1193-24-4

4,6-pyrimidinediol

Conditions
ConditionsYield
reagiert analog mit Propionamidin;

A

C21H15N3O5

C21H15N3O5

B

2-(2-(6-(2-cyanophenoxy)pyrimidin-4-yloxy)phenyl)acetic acid methyl ester

2-(2-(6-(2-cyanophenoxy)pyrimidin-4-yloxy)phenyl)acetic acid methyl ester

C

methyl (E)-2-[2-[6-(2-cyanophenoxy)pyrimidin-4-yl]oxyphenyl]-3-methoxyprop-2-enoate

methyl (E)-2-[2-[6-(2-cyanophenoxy)pyrimidin-4-yl]oxyphenyl]-3-methoxyprop-2-enoate

D

4,6-pyrimidinediol
1193-24-4

4,6-pyrimidinediol

Conditions
ConditionsYield
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

malonodiamide

formic acid ethyl ester
109-94-4

formic acid ethyl ester

4,6-pyrimidinediol
1193-24-4

4,6-pyrimidinediol

Conditions
ConditionsYield
With sodium ethanolate In ethanol Reflux;
acetamidine
143-37-3

acetamidine

diethyl malonate
105-53-3

diethyl malonate

4,6-pyrimidinediol
1193-24-4

4,6-pyrimidinediol

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

4,6-Dihydroxypyrimidine Chemical Properties

IUPAC Name: 4-hydroxy-1H-pyrimidin-6-one 
Empirical Formula: C4H4N2O2
Molecular Weight: 112.0868g/mol 
EINECS: 214-772-3 
Structure of 4,6-Dihydroxypyrimidine (CAS NO.1193-24-4):

Index of Refraction: 1.648
Molar Refractivity: 26.23 cm3
Molar Volume: 72 cm3
Polarizability: 10.4×10-24cm3
Surface Tension: 65.3 dyne/cm
Density: 1.55 g/cm3
Flash Point: 170.6 °C
Enthalpy of Vaporization: 62.78 kJ/mol 
Melting Point: >300 °C(lit.)
Boiling Point: 358.5 °C at 760 mmHg
Vapour Pressure: 1.22E-05 mmHg at 25°C 
Water Solubility: 2.5 g/L (20 º C)
 Product Categories: PYRIMIDINE;FINE Chemical & INTERMEDIATES;APIs & Intermediate;Nucleotides and Nucleosides;Pyrimidines;Bases & Related Reagents;Nucleotides 
Canonical SMILES: C1=C(N=CNC1=O)O
InChI: InChI=1S/C4H4N2O2/c7-3-1-4(8)6-2-5-3/h1-2H,(H2,5,6,7,8)
InChIKey: DUFGYCAXVIUXIP-UHFFFAOYSA-N

4,6-Dihydroxypyrimidine Toxicity Data With Reference

1.    

pic-esc 1 g/L

    ZAPOAK    Zeitschrift fuer Allgemeine Mikrobiologie. Morphologie, Physiologie, Genetik und Oekologie der Mikroorganismen. 12 (1972),583.

4,6-Dihydroxypyrimidine Consensus Reports

Reported in EPA TSCA Inventory.

4,6-Dihydroxypyrimidine Safety Profile

Hazard Codes: IrritantXi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36-37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing. 
S37/39:Wear suitable gloves and eye/face protection.
WGK Germany: 1
RTECS: UW7523000
Hazard Note: Irritant
HS Code 29335995
Mutation data reported. When heated to decomposition it emits toxic vapors of NOx.

4,6-Dihydroxypyrimidine Specification

  4,6-Dihydroxypyrimidine , its cas register number is 1193-24-4. It also can be called 4(3H)-Pyrimidinone, 6-hydroxy- ; 4,6-Dihydroxypyrimidin ; 4,6-Pyrimidinediol ; 6-Hydroxy-4(1H)-pyrimidinone ; NSC 22838 . 4,6-Dihydroxypyrimidine (CAS NO.1193-24-4) is a light yellow powder.

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