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103766-25-2

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103766-25-2 Usage

Description

Gimeracil (103766-25-2) is a dihydropyrimidine dehydrogenase (DPD) inhibitor.? DPD is involved in the degradation of pyrimidine-based chemotherapeutic drugs such as 5-fluorouracil (5-FU).? Gimeracil is used along with 5-FU or Tegafur to prolong circulating concentrations of the drugs.1,2? Gimeracil has also been shown to act as a radiosensitizer via inhibition of homologous recombination in the repair of DNA double strand breaks.3

Chemical Properties

Off-White Solid

Uses

Different sources of media describe the Uses of 103766-25-2 differently. You can refer to the following data:
1. Gimeracil is an inhibitor of dihydropyrimidine dehydrogenase, which inhibits the early step in homologous recombination for double strand breaks repair.
2. Gimeracil is an antitumor agent. Gimeracil is a potent inhibitor of dihydropyrimidine dehydrogenase (DPD).
3. Antitumor agent. A potent inhibitor of dihydropyrimidine dehydrogenase (DPD)

References

1) Diasio (1999)?Clinical implications of dihydropyrimidine dehydrogenase inhibition; Oncology(Williston Park),?13?17 2) Kobayakawa and Kojima (2011),?Tegafur/gimeracil/oteracil (S-1) approved for the treatment of advanced gastric cancer in adults when given in combination with cisplatin: a review comparing it with other fluoropyrimidine-based therapies; Onco. Targets Ther.,?4?193 3) Sakata?et al.?(2011),?Gimeracil, an inhibitor of dihydropyrimidine dehydrogenase, inhibits the early step in homologous recombination; Cancer Sci.,?102?1712

Check Digit Verification of cas no

The CAS Registry Mumber 103766-25-2 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,0,3,7,6 and 6 respectively; the second part has 2 digits, 2 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 103766-25:
(8*1)+(7*0)+(6*3)+(5*7)+(4*6)+(3*6)+(2*2)+(1*5)=112
112 % 10 = 2
So 103766-25-2 is a valid CAS Registry Number.
InChI:InChI=1/C5H4ClNO2/c6-3-2-7-5(9)1-4(3)8/h1-2H,(H2,7,8,9)

103766-25-2 Well-known Company Product Price

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  • TCI America

  • (C2243)  Gimeracil  >98.0%(HPLC)(T)

  • 103766-25-2

  • 1g

  • 850.00CNY

  • Detail
  • TCI America

  • (C2243)  Gimeracil  >98.0%(HPLC)(T)

  • 103766-25-2

  • 5g

  • 2,450.00CNY

  • Detail

103766-25-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name 5-chloro-4-hydroxy-1H-pyridin-2-one

1.2 Other means of identification

Product number -
Other names Gimeracil

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:103766-25-2 SDS

103766-25-2Synthetic route

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

3,5-dichloro-2,4-dihydroxypyridine

5-Chloro-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℃;
3-Chloro-1,5-dioxa-spiro[5.5]undec-3-en-2-one
134878-51-6

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

ketene diethyl acetal
2678-54-8

ketene diethyl acetal

5-Chloro-2,4-dihydroxypyridine
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%
5-chloro-2,2-diethoxy-2,3-dihydropyran-4-one
904731-84-6

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

5-Chloro-2,4-dihydroxypyridine
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;
4,5-dichloro-2-hydroxypyridine
856965-66-7

4,5-dichloro-2-hydroxypyridine

sodium ethanolate
141-52-6

sodium ethanolate

A

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

5-Chloro-2,4-dihydroxypyridine

B

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

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

Conditions
ConditionsYield
With ethanol at 180℃;
4,5-dichloro-2-hydroxypyridine
856965-66-7

4,5-dichloro-2-hydroxypyridine

A

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

5-Chloro-2,4-dihydroxypyridine

B

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

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

Conditions
ConditionsYield
With ethanol; sodium ethanolate at 180℃;
2,4-diethoxy-5-chloro-pyridine
856850-46-9

2,4-diethoxy-5-chloro-pyridine

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

5-Chloro-2,4-dihydroxypyridine

Conditions
ConditionsYield
With hydrogenchloride at 160℃;
4-chloro-2-ethoxypyridine
856851-45-1

4-chloro-2-ethoxypyridine

5-Chloro-2,4-dihydroxypyridine
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
2-ethoxy-4,5-dichloro-pyridine
857991-71-0

2-ethoxy-4,5-dichloro-pyridine

5-Chloro-2,4-dihydroxypyridine
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
5-chloro-2-methoxy-2-t-butyldimethylsilyloxy-2,3-dihydropyran-4-one
904731-85-7

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

5-Chloro-2,4-dihydroxypyridine
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;
2,4-dichloropyridine
26452-80-2

2,4-dichloropyridine

5-Chloro-2,4-dihydroxypyridine
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
2,4-dimethoxypyridine
18677-43-5

2,4-dimethoxypyridine

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

5-Chloro-2,4-dihydroxypyridine

Conditions
ConditionsYield
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
3,5-dichloro-2,4-dimethoxypyridine
847550-92-9

3,5-dichloro-2,4-dimethoxypyridine

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

5-Chloro-2,4-dihydroxypyridine

Conditions
ConditionsYield
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
5-Chloro-2,4-dihydroxypyridine
103766-25-2

5-Chloro-2,4-dihydroxypyridine

4-methyl-benzoyl chloride
874-60-2

4-methyl-benzoyl chloride

C21H16ClNO4

C21H16ClNO4

Conditions
ConditionsYield
With pyridine for 2h; Ambient temperature;97%
5-Chloro-2,4-dihydroxypyridine
103766-25-2

5-Chloro-2,4-dihydroxypyridine

benzoyl chloride
98-88-4

benzoyl chloride

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

2,4-dibenzoyloxy-5-chloropyridine

Conditions
ConditionsYield
With pyridine for 2h; Ambient temperature;87%
5-Chloro-2,4-dihydroxypyridine
103766-25-2

5-Chloro-2,4-dihydroxypyridine

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

1,1,1,3,3,3-hexamethyl-disilazane

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

2,4-bis(trimethylsilyloxy)-5-chloropyridine

Conditions
ConditionsYield
Heating;75%
for 6h; Reflux;
5-Chloro-2,4-dihydroxypyridine
103766-25-2

5-Chloro-2,4-dihydroxypyridine

acetyl chloride
75-36-5

acetyl chloride

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

4-acetoxy-5-chloro-2(1H)-pyridone

Conditions
ConditionsYield
With pyridine for 4h; Ambient temperature;52%
5-Chloro-2,4-dihydroxypyridine
103766-25-2

5-Chloro-2,4-dihydroxypyridine

benzoyl chloride
98-88-4

benzoyl chloride

A

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

2-benzoyloxy-5-chloro-2-pyridone

B

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

4-benzoyloxy-5-chloro-2-pyridone

C

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

2,4-dibenzoyloxy-5-chloropyridine

Conditions
ConditionsYield
With pyridine for 4h; Ambient temperature;A n/a
B 47%
C 18.9%
5-Chloro-2,4-dihydroxypyridine
103766-25-2

5-Chloro-2,4-dihydroxypyridine

4-methyl-benzoyl chloride
874-60-2

4-methyl-benzoyl chloride

A

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

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

B

C21H16ClNO4

C21H16ClNO4

Conditions
ConditionsYield
With pyridine for 4h; Ambient temperature;A 36%
B n/a
5-Chloro-2,4-dihydroxypyridine
103766-25-2

5-Chloro-2,4-dihydroxypyridine

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

2,3,5-trichloropyridine

Conditions
ConditionsYield
With trichlorophosphate at 130℃;
5-Chloro-2,4-dihydroxypyridine
103766-25-2

5-Chloro-2,4-dihydroxypyridine

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

3-bromo-5-chloro-pyridine-2,4-diol

Conditions
ConditionsYield
With hydrogen bromide; bromine at 100℃;
5-Chloro-2,4-dihydroxypyridine
103766-25-2

5-Chloro-2,4-dihydroxypyridine

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

2,4-dibromo-5-chloropyridine

Conditions
ConditionsYield
With phosphorus(V) oxybromide at 160℃;
5-Chloro-2,4-dihydroxypyridine
103766-25-2

5-Chloro-2,4-dihydroxypyridine

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

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 75 percent / Heating
2: stannic chloride / CH2Cl2 / 5 h / Ambient temperature
View Scheme
5-Chloro-2,4-dihydroxypyridine
103766-25-2

5-Chloro-2,4-dihydroxypyridine

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

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 75 percent / Heating
2: 49 percent / acetonitrile / 6 h / Ambient temperature
View Scheme
5-Chloro-2,4-dihydroxypyridine
103766-25-2

5-Chloro-2,4-dihydroxypyridine

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

5-chloro-1-ethoxymethyl-4-hydroxy-2(1H)-pyridone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 75 percent / Heating
2: 39 percent / acetonitrile / 6 h / Ambient temperature
View Scheme
5-Chloro-2,4-dihydroxypyridine
103766-25-2

5-Chloro-2,4-dihydroxypyridine

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

(+/-)-5-chloro-4-hydroxy-1-(2-tetrahydrofuryl)-2-pyridone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 75 percent / Heating
2: stannic chloride / CH2Cl2 / Ambient temperature
View Scheme
5-Chloro-2,4-dihydroxypyridine
103766-25-2

5-Chloro-2,4-dihydroxypyridine

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

2-benzoyloxy-5-chloro-2-pyridone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 75 percent / Heating
2: stannic chloride / CH2Cl2 / 5 h / Ambient temperature
View Scheme
5-Chloro-2,4-dihydroxypyridine
103766-25-2

5-Chloro-2,4-dihydroxypyridine

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

4-benzoyloxy-5-chloro-2-pyridone

Conditions
ConditionsYield
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
5-Chloro-2,4-dihydroxypyridine
103766-25-2

5-Chloro-2,4-dihydroxypyridine

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

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 75 percent / Heating
2: 57 percent / acetonitrile / 6 h / Ambient temperature
View Scheme
5-Chloro-2,4-dihydroxypyridine
103766-25-2

5-Chloro-2,4-dihydroxypyridine

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

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

Conditions
ConditionsYield
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
5-Chloro-2,4-dihydroxypyridine
103766-25-2

5-Chloro-2,4-dihydroxypyridine

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

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

Conditions
ConditionsYield
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
5-Chloro-2,4-dihydroxypyridine
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

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

Conditions
ConditionsYield
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
5-Chloro-2,4-dihydroxypyridine
103766-25-2

5-Chloro-2,4-dihydroxypyridine

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

2,5-dichloro-4-amino-pyridine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: phosphoryl chloride / 130 °C
2: aqueous NH3 / 160 °C
View Scheme
5-Chloro-2,4-dihydroxypyridine
103766-25-2

5-Chloro-2,4-dihydroxypyridine

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

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: concentrated aqueous hydrobromic acid; bromine / 100 °C
2: phosphoryl chloride / 130 °C
View Scheme
5-Chloro-2,4-dihydroxypyridine
103766-25-2

5-Chloro-2,4-dihydroxypyridine

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

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

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

103766-25-2Related news

Gimeracil (cas 103766-25-2) sensitizes cells to radiation via inhibition of homologous recombination07/17/2019

Background and purpose5-Chloro-2,4-dihydroxypyridine (Gimeracil) is a component of an oral fluoropyrimidine derivative S-1. Gimeracil is originally added to S-1 to yield prolonged 5-FU concentrations in tumor tissues by inhibiting dihydropyrimidine dehydrogenase, which degrades 5-FU. We found th...detailed

Equilibrium solubility investigation and thermodynamic aspects of biologically active Gimeracil (cas 103766-25-2) (form P) dissolved in aqueous co-solvent mixtures of isopropanol, N,N-dimethylformamide, ethylene glycol and dimethylsulfoxide07/16/2019

Solubilities of gimeracil (form P) in aqueous co-solvent mixtures of isopropanol, N,N-dimethylformamide (DMF), ethylene glycol (EG) and dimethylsulfoxide (DMSO) were investigated via the isothermal dissolution equilibrium method at (283.15–328.15) K under ambient pressure p = 101.2 kPa. Experim...detailed

103766-25-2Relevant articles and documents

CONVENIENT AND PRACTICAL SYNTHESIS OF 5-CHLORO-4-HYDROXY-2(1H)-PYRIDINONE

Yano, Shin-go,Ohno, Tomoyasu,Ogawa, Kazuo

, p. 145 - 148 (1993)

5-Chloro-4-hydroxy-2(1H)-pyridinone (1) was prepared by 4-step reactions via the key intermediate 5-chloro-3-cyano-4-methoxy-2(1H)-pyridinone (5).This synthetic route has several advantages over the reported methods in procedure, yield and applicability.

A convenient synthesis of gimeracil

Li, Xiao-Lin,Zhu, Hao-Ting,Zhan, Li,Liu, Ting,Cheng, Guang,Liu, Ning,Yu, Shan-Bao,Li, Hui,Luo, Yu,Yang, Fan,Tang, Jie

, p. 33 - 34 (2018/02/28)

A practical three-step synthetic approach to gimeracil in a 68% overall yield is described, using 2,4-dimethoxypyridine as the starting material with 3,5-dichloro-2,4-dimethoxypyridine and 3,5-dichloro-2,4-dihydroxypyridine as intermediates. The advantages of this procedure include short reaction steps, simple operation and good yield.

A lucky US pyrimidine of the composition and its preparation method

-

Paragraph 0025; 0041; 0042; 0043; 0044; 0045, (2017/08/02)

The invention provides a gimeracil composition, a preparation method of gimeracil analogues such as 1-methyl-4-hydroxyl-5-chloro-2-(1H) pyridine, 4-methoxy-5-chloro-2-(1H) pyridine and 3-cyano-4-hydroxyl-5-chloro-2-(1H) pyridine, and application of the analogues in research on quality control of gimeracil.

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