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Gimeracil
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Name

Gimeracil

 EINECS 1312995-182-4
CAS No. 103766-25-2 Density 1.56 g/cm3
PSA 53.09000 LogP 0.73390
Solubility N/A Melting Point 274 ºC
Formula C5H4ClNO2 Boiling Point 281.9 ºC at 760 mmHg
Molecular Weight 145.545 Flash Point 124.3 ºC
Transport Information N/A Appearance N/A
Safety 24/25 Risk Codes R11; R14; R34
Molecular Structure Molecular Structure of 103766-25-2 (Gimeracil) Hazard Symbols F,C
Synonyms

5-Chloro-2,4-dihydroxypyridine;5-Chloro-4-hydroxy-2(1H)-pyridinone;5-Chloro-4-hydroxy-2-pyridone;2(1H)-Pyridinone, 5-chloro-4-hydroxy-;Gimestat;Cdhp compound;

Article Data 8

Gimeracil Synthetic route

103792-80-9

3,5-dichloro-2,4-dihydroxypyridine

103766-25-2

5-Chloro-2,4-dihydroxypyridine

Conditions
ConditionsYield
With acetic acid; sodium iodide In acetonitrile at 60℃; for 8h;86%
With hydrogen bromide; sodium hydrogensulfite at 200℃;
134878-51-6

3-Chloro-1,5-dioxa-spiro[5.5]undec-3-en-2-one

2678-54-8

ketene diethyl acetal

103766-25-2

5-Chloro-2,4-dihydroxypyridine

Conditions
ConditionsYield
Stage #1: 3-Chloro-1,5-dioxa-spiro[5.5]undec-3-en-2-one; ketene diethyl acetal In water; xylene at 128 - 130℃; for 0.666667h;
Stage #2: With acetyl chloride In ethanol at 20℃; for 1h;
Stage #3: With sodium hydroxide; ammonia Product distribution / selectivity; more than 3 stages;		72.4%
904731-84-6

5-chloro-2,2-diethoxy-2,3-dihydropyran-4-one

103766-25-2

5-Chloro-2,4-dihydroxypyridine

Conditions
ConditionsYield
Stage #1: 5-chloro-2,2-diethoxy-2,3-dihydropyran-4-one With acetyl chloride In ethanol at 20℃; for 1h;
Stage #2: With ammonia In ethanol; water at 20℃; for 15h; Product distribution / selectivity;		33%
Stage #1: 5-chloro-2,2-diethoxy-2,3-dihydropyran-4-one With acetyl chloride In ethanol at 20℃; for 1h;
Stage #2: With ammonia In ethanol; water at 20℃; for 16h; Product distribution / selectivity;
856965-66-7

4,5-dichloro-2-hydroxypyridine

141-52-6

sodium ethanolate

A

103766-25-2

5-Chloro-2,4-dihydroxypyridine

B

4-ethoxy-5-chloro-pyridin-2-ol

Conditions
ConditionsYield
With ethanol at 180℃;
856965-66-7

4,5-dichloro-2-hydroxypyridine

A

103766-25-2

5-Chloro-2,4-dihydroxypyridine

B

4-ethoxy-5-chloro-pyridin-2-ol

Conditions
ConditionsYield
With ethanol; sodium ethanolate at 180℃;
856850-46-9

2,4-diethoxy-5-chloro-pyridine

103766-25-2

5-Chloro-2,4-dihydroxypyridine

Conditions
ConditionsYield
With hydrogenchloride at 160℃;
856851-45-1

4-chloro-2-ethoxypyridine

103766-25-2

5-Chloro-2,4-dihydroxypyridine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: acetic acid; chlorine
2: aqueous hydrochloric acid / 160 °C / Unter Druck
3: sodium ethylate; ethanol / 180 °C
View Scheme
Multi-step reaction with 3 steps
1: acetic acid; chlorine
2: aqueous ethanolic NaOH-solution / 160 °C
3: aqueous hydrochloric acid / 160 °C
View Scheme
Multi-step reaction with 3 steps
1: acetic acid; chlorine
2: aqueous ethanolic NaOH-solution / 160 °C
3: aqueous hydrochloric acid / 160 °C
View Scheme
857991-71-0

2-ethoxy-4,5-dichloro-pyridine

103766-25-2

5-Chloro-2,4-dihydroxypyridine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aqueous hydrochloric acid / 160 °C / Unter Druck
2: sodium ethylate; ethanol / 180 °C
View Scheme
Multi-step reaction with 2 steps
1: aqueous ethanolic NaOH-solution / 160 °C
2: aqueous hydrochloric acid / 160 °C
View Scheme
Multi-step reaction with 2 steps
1: aqueous ethanolic NaOH-solution / 160 °C
2: aqueous hydrochloric acid / 160 °C
View Scheme
904731-85-7

5-chloro-2-methoxy-2-t-butyldimethylsilyloxy-2,3-dihydropyran-4-one

103766-25-2

5-Chloro-2,4-dihydroxypyridine

Conditions
ConditionsYield
Stage #1: 5-chloro-2-methoxy-2-t-butyldimethylsilyloxy-2,3-dihydropyran-4-one With acetyl chloride In methanol at 20℃; for 1h;
Stage #2: With ammonia In methanol; water for 2.5h; Product distribution / selectivity;
26452-80-2

2,4-dichloropyridine

103766-25-2

5-Chloro-2,4-dihydroxypyridine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 6 h / 120 °C / Inert atmosphere
2: N-chloro-succinimide / acetonitrile / 3 h / 50 °C
3: water; hydrogenchloride / 6 h / 70 °C
4: acetic acid; sodium iodide / acetonitrile / 8 h / 60 °C
View Scheme
Multi-step reaction with 4 steps
1: 6 h / 120 °C / Inert atmosphere
2: N-chloro-succinimide / acetonitrile / 50 °C
3: water; hydrogenchloride / 6 h / 70 °C
4: acetic acid; sodium iodide / acetonitrile / 8 h / 60 °C
View Scheme

Gimeracil Specification

The Gimeracil with CAS registry number of 103766-25-2 is also known as 5-Chloro-4-hydroxy-2(1H)-pyridinone. The IUPAC name is 5-Chloro-2-hydroxy-1H-pyridin-4-one. It belongs to product categories of Pyridine; Antitumors for Research and Experimental Use; Biochemistry; Chloropyridines; Halopyridines; Intermediates & Fine Chemicals; Pharmaceuticals. In addition, the formula is C5H4ClNO2 and the molecular weight is 145.54. This chemical can be used as antitumor agent and a potent inhibitor of dihydropyrimidine dehydrogenase (DPD).

Physical properties about Gimeracil are: (1)ACD/LogP: -1.04; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -2.35; (4)ACD/LogD (pH 7.4): -4.05; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 3; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 1; (12)Index of Refraction: 1.617; (13)Molar Refractivity: 32.64 cm3; (14)Molar Volume: 93.2 cm3; (15)Surface Tension: 58.4 dyne/cm; (16)Density: 1.56 g/cm3; (17)Flash Point: 124.3 °C; (18)Enthalpy of Vaporization: 60.44 kJ/mol; (19)Boiling Point: 281.9 °C at 760 mmHg; (20)Vapour Pressure: 0.000408 mmHg at 25 °C.

You can still convert the following datas into molecular structure:
1. Canonical SMILES: C1=C(NC=C(C1=O)Cl)O
2. InChI: InChI=1S/C5H4ClNO2/c6-3-2-7-5(9)1-4(3)8/h1-2H,(H2,7,8,9)
3. InChIKey: ZPLQIPFOCGIIHV-UHFFFAOYSA-N

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