Gimeracil supplier | CasNO.103766-25-2

Name
Gimeracil
EINECS 1312995-182-4
CAS No. 103766-25-2
Article Data8
CAS DataBase
Density 1.56 g/cm³
Solubility
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
Appearance
Safety 24/25
Risk Codes R11; R14; R34
Molecular Structure
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;
PSA 53.09000
LogP 0.73390

Synthetic route

: 103792-80-9
3,5-dichloro-2,4-dihydroxypyridine

: 103766-25-2
5-Chloro-2,4-dihydroxypyridine

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With ethanol at 180℃;

...Expand

: 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

Conditions	Yield
With ethanol; sodium ethanolate at 180℃;

: 856850-46-9
2,4-diethoxy-5-chloro-pyridine

: 103766-25-2
5-Chloro-2,4-dihydroxypyridine

Conditions

Conditions	Yield
With hydrogenchloride at 160℃;

: 856851-45-1
4-chloro-2-ethoxypyridine

: 103766-25-2
5-Chloro-2,4-dihydroxypyridine

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

: 18677-43-5
2,4-dimethoxypyridine

: 103766-25-2
5-Chloro-2,4-dihydroxypyridine

Conditions

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

: 847550-92-9
3,5-dichloro-2,4-dimethoxypyridine

: 103766-25-2
5-Chloro-2,4-dihydroxypyridine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: water; hydrogenchloride / 6 h / 70 °C 2: acetic acid; sodium iodide / acetonitrile / 8 h / 60 °C View Scheme

: 103766-25-2
5-Chloro-2,4-dihydroxypyridine

: 874-60-2
4-methyl-benzoyl chloride

: C21H16ClNO4

Conditions

Conditions	Yield
With pyridine for 2h; Ambient temperature;	97%

: 103766-25-2
5-Chloro-2,4-dihydroxypyridine

: 98-88-4
benzoyl chloride

: 103815-09-4
2,4-dibenzoyloxy-5-chloropyridine

Conditions

Conditions	Yield
With pyridine for 2h; Ambient temperature;	87%

: 103766-25-2
5-Chloro-2,4-dihydroxypyridine

: 999-97-3
1,1,1,3,3,3-hexamethyl-disilazane

: 103766-30-9
2,4-bis(trimethylsilyloxy)-5-chloropyridine

Conditions

Conditions	Yield
Heating;	75%
for 6h; Reflux;

: 103766-25-2
5-Chloro-2,4-dihydroxypyridine

: 75-36-5
acetyl chloride

: 103766-99-0
4-acetoxy-5-chloro-2(1H)-pyridone

Conditions

Conditions	Yield
With pyridine for 4h; Ambient temperature;	52%

: 103766-25-2
5-Chloro-2,4-dihydroxypyridine

: 98-88-4
benzoyl chloride

A: 155131-51-4, 103766-26-3
2-benzoyloxy-5-chloro-2-pyridone

B: 103766-97-8
4-benzoyloxy-5-chloro-2-pyridone

C: 103815-09-4
2,4-dibenzoyloxy-5-chloropyridine

Conditions

Conditions	Yield
With pyridine for 4h; Ambient temperature;	A n/a B 47% C 18.9%

...Expand

: 103766-25-2
5-Chloro-2,4-dihydroxypyridine

: 874-60-2
4-methyl-benzoyl chloride

A: 4-Methyl-benzoic acid 5-chloro-2-oxo-1,2-dihydro-pyridin-4-yl ester

B: C21H16ClNO4

Conditions

Conditions	Yield
With pyridine for 4h; Ambient temperature;	A 36% B n/a

...Expand

: 103766-25-2
5-Chloro-2,4-dihydroxypyridine

: 55934-01-5
2,3,5-trichloropyridine

Conditions

Conditions	Yield
With trichlorophosphate at 130℃;

: 103766-25-2
5-Chloro-2,4-dihydroxypyridine

: 859295-89-9
3-bromo-5-chloro-pyridine-2,4-diol

Conditions

Conditions	Yield
With hydrogen bromide; bromine at 100℃;

: 103766-25-2
5-Chloro-2,4-dihydroxypyridine

: 875232-70-5
2,4-dibromo-5-chloropyridine

Conditions

Conditions	Yield
With phosphorus(V) oxybromide at 160℃;

: 103766-25-2
5-Chloro-2,4-dihydroxypyridine

: Acetic acid 5-chloro-4-oxo-1,4-dihydro-pyridin-2-yl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 75 percent / Heating 2: stannic chloride / CH2Cl2 / 5 h / Ambient temperature View Scheme

: 103766-25-2
5-Chloro-2,4-dihydroxypyridine

: 5-chloro-4-hydroxyl-1-methoxymethyl-2-pyridone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 75 percent / Heating 2: 49 percent / acetonitrile / 6 h / Ambient temperature View Scheme

: 103766-25-2
5-Chloro-2,4-dihydroxypyridine

: 103815-27-6
5-chloro-1-ethoxymethyl-4-hydroxy-2(1H)-pyridone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 75 percent / Heating 2: 39 percent / acetonitrile / 6 h / Ambient temperature View Scheme

: 103766-25-2
5-Chloro-2,4-dihydroxypyridine

: 103792-63-8
(+/-)-5-chloro-4-hydroxy-1-(2-tetrahydrofuryl)-2-pyridone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 75 percent / Heating 2: stannic chloride / CH2Cl2 / Ambient temperature View Scheme

: 103766-25-2
5-Chloro-2,4-dihydroxypyridine

: 155131-51-4, 103766-26-3
2-benzoyloxy-5-chloro-2-pyridone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 75 percent / Heating 2: stannic chloride / CH2Cl2 / 5 h / Ambient temperature View Scheme

: 103766-25-2
5-Chloro-2,4-dihydroxypyridine

: 103766-97-8
4-benzoyloxy-5-chloro-2-pyridone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 18.9 percent / pyridine / 4 h / Ambient temperature 2: 37 percent / aniline / dioxane / 7 h / 90 - 100 °C View Scheme
Multi-step reaction with 2 steps 1: 87 percent / pyridine / 2 h / Ambient temperature 2: 37 percent / aniline / dioxane / 7 h / 90 - 100 °C View Scheme

: 103766-25-2
5-Chloro-2,4-dihydroxypyridine

: 1-benzyloxymethyl-5-chloro-4-hydroxy-2(1H)-pyridone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 75 percent / Heating 2: 57 percent / acetonitrile / 6 h / Ambient temperature View Scheme

: 103766-25-2
5-Chloro-2,4-dihydroxypyridine

: 4-benzoyloxy-5-chloro-1-ethoxymethyl-2-pyridone

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 75 percent / Heating 2: 39 percent / acetonitrile / 6 h / Ambient temperature 3: 93 percent / Et3N / dioxane / 6 h / Heating View Scheme

: 103766-25-2
5-Chloro-2,4-dihydroxypyridine

: 3-[3-(2-benzoyloxy-5-chloro-4-pyridyloxycarbonyl)-benzoyl]-5-fluoro-1-(2-tetrahydrofuranyl)uracil

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine / 4 h / Ambient temperature 2: Et3N / CHCl3 / 2 h / Ambient temperature View Scheme
Multi-step reaction with 3 steps 1: 75 percent / Heating 2: stannic chloride / CH2Cl2 / 5 h / Ambient temperature 3: Et3N / CHCl3 / 2 h / Ambient temperature View Scheme

: 103766-25-2
5-Chloro-2,4-dihydroxypyridine

: 3-[3-(2-acetoxy-5-chloro-4-pyridyloxycarbonyl)-benzoyl]-5'-deoxy-2',3'-di-O-acetyl-5-fluorouridine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 75 percent / Heating 2: stannic chloride / CH2Cl2 / 5 h / Ambient temperature 3: Et3N / CHCl3 / 2 h / Ambient temperature View Scheme

: 103766-25-2
5-Chloro-2,4-dihydroxypyridine

: 405230-82-2
2,5-dichloro-4-amino-pyridine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: phosphoryl chloride / 130 °C 2: aqueous NH3 / 160 °C View Scheme

: 103766-25-2
5-Chloro-2,4-dihydroxypyridine

: 3-bromo-2,4,5-trichloro-pyridine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: concentrated aqueous hydrobromic acid; bromine / 100 °C 2: phosphoryl chloride / 130 °C View Scheme

: 103766-25-2
5-Chloro-2,4-dihydroxypyridine

: 2,3,4-tribromo-5-chloro-pyridine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: concentrated aqueous hydrobromic acid; bromine / 100 °C 2: phosphoryl bromide / 160 °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

Product Name

Gimeracil

Synthetic route

Gimeracil Specification

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