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863329-65-1

863329-65-1

Identification

Synonyms:(2'R)-2'-Deoxy-2'-fluoro-2'-Methyl-uridine 3',5'-dibenzoate;2'Deoxy-2'fluoro-2'- Methyl- 3'5'-bis-o- (phenylcarbonyl) uridine;((2R,3R,4R,5R)-3-(benzoyloxy)-5-(2,4-dioxo-3,4-dihydropyriMidin-1(2H)-yl)-4-fluoro-4-Methyltetrahydrofuran-2-yl)Methyl benzoate;URIDINE, 2'-DEOXY-2'-FLUORO-2'-METHYL-, 3',5'-DIBENZOATE, (2'R)-;3',5'-di-O-benzoyl-2'-deoxy-2'-fluoro-2'-C-Methyluridine;Sofosbuvir Intermediate 3;[(2R,3R,4R,5R)-3-Benzoyloxy-5-(2,4-dioxopyrimidin-1-yl)-4-fluoro-4-methyl-tetrahydrofuran-2-yl]methyl benzoate;3',5'-Di-O-benzoyl-2'-deoxy-2'-fluoro-2'-methyluridine

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Safety information and MSDS view more

  • Signal Word:Warning

  • Hazard Statement:H319 Causes serious eye irritation

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

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  • Manufacture/Brand:TRC
  • Product Description:RO2433Dibenzoate
  • Packaging:100mg
  • Price:$ 60
  • Delivery:In stock
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  • Manufacture/Brand:TRC
  • Product Description:RO2433Dibenzoate
  • Packaging:1g
  • Price:$ 475
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:[(2R,3R,4R,5R)-3-Benzoyloxy-5-(2,4-dioxopyrimidin-1-yl)-4-fluoro-4-methyl-tetrahydrofuran-2-yl]methylbenzoate 95+%
  • Packaging:1g
  • Price:$ 594
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  • Manufacture/Brand:Crysdot
  • Product Description:[(2R,3R,4R,5R)-3-Benzoyloxy-5-(2,4-dioxopyrimidin-1-yl)-4-fluoro-4-methyl-tetrahydrofuran-2-yl]methylbenzoate 95+%
  • Packaging:1g
  • Price:$ 401
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  • Manufacture/Brand:Crysdot
  • Product Description:[(2R,3R,4R,5R)-3-Benzoyloxy-5-(2,4-dioxopyrimidin-1-yl)-4-fluoro-4-methyl-tetrahydrofuran-2-yl]methylbenzoate 95+%
  • Packaging:5g
  • Price:$ 1207
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  • Manufacture/Brand:Chemenu
  • Product Description:[(2R,3R,4R,5R)-3-Benzoyloxy-5-(2,4-dioxopyrimidin-1-yl)-4-fluoro-4-methyl-tetrahydrofuran-2-yl]methylbenzoate 95%
  • Packaging:5g
  • Price:$ 1137
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  • Manufacture/Brand:Chemenu
  • Product Description:[(2R,3R,4R,5R)-3-Benzoyloxy-5-(2,4-dioxopyrimidin-1-yl)-4-fluoro-4-methyl-tetrahydrofuran-2-yl]methylbenzoate 95%
  • Packaging:1g
  • Price:$ 379
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  • Manufacture/Brand:BLDpharm
  • Product Description:[(2R,3R,4R,5R)-3-Benzoyloxy-5-(2,4-dioxopyrimidin-1-yl)-4-fluoro-4-methyl-tetrahydrofuran-2-yl]methylbenzoate 95+%
  • Packaging:1g
  • Price:$ 530
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Relevant articles and documentsAll total 18 Articles be found

Structure-activity relationship of uridine-based nucleoside phosphoramidate prodrugs for inhibition of dengue virus RNA-dependent RNA polymerase

Wang, Gang,Lim, Siew Pheng,Chen, Yen-Liang,Hunziker, Jürg,Rao, Ranga,Gu, Feng,Seh, Cheah Chen,Ghafar, Nahdiyah Abdul,Xu, Haoying,Chan, Katherine,Lin, Xiaodong,Saunders, Oliver L.,Fenaux, Martijn,Zhong, Weidong,Shi, Pei-Yong,Yokokawa, Fumiaki

, p. 2324 - 2327 (2018/05/28)

To identify a potent and selective nucleoside inhibitor of dengue virus RNA-dependent RNA polymerase, a series of 2′- and/or 4′-ribose sugar modified uridine nucleoside phosphoramidate prodrugs and their corresponding triphosphates were synthesized and evaluated. Replacement of 2′-OH with 2′-F led to be a poor substrate for both dengue virus and human mitochondrial RNA polymerases. Instead of 2′-fluorination, the introduction of fluorine at the ribose 4′-position was found not to affect the inhibition of the dengue virus polymerase with a reduction in uptake by mitochondrial RNA polymerase. 2′-C-ethynyl-4′-F-uridine phosphoramidate prodrug displayed potent anti-dengue virus activity in the primary human peripheral blood mononuclear cell-based assay with no significant cytotoxicity in human hepatocellular liver carcinoma cell lines and no mitochondrial toxicity in the cell-based assay using human prostate cancer cell lines.

AN IMPROVED PROCESS FOR THE PREPARATION OF SOFOSBUVIR

-

Page/Page column 5; 8, (2018/02/20)

The present invention relates to an improved, commercially viable and industrially advantageous process for the preparation of Sofosbuvir. The present invention involves use of reagents that are less expensive, easier to handle and eco-friendly process.

Nucleoside phosphoramidate compound optical isomer and its application

-

Paragraph 0089-0091, (2018/07/30)

The invention belongs to the field of medicinal chemistry, and in particular relates to a nucleoside phosphoramidate compound optical isomer or its hydrate, solvate, crystal or a pharmaceutically acceptable salt, process for their preparation and pharmaceutical compositions containing these compounds and these compounds or compositions used as virus infectious disease treating drug use, in particular as viral hepatitis treatment drug use. The experimental result shows, the compounds of this invention to hepatitis c virus 1 b subtype and 1 a subtype exhibit good inhibitory activity, while at the same time to the host cell has very low toxicity, high effectiveness, the safety is good, suitable for the treatment and/or prevention of diseases associated with HCV infection.

Biphenyl nucleoside phosphoramidate application of compound

-

Paragraph 0033; 0034; 0035, (2018/07/07)

The invention belongs to the field of medicinal chemistry, provided the present invention of the formula 1 compound or its pharmaceutically acceptable salt, solvate, hydrate, stereoisomer or crystallization in preparation for the treatment of flavivirus, especially hepatitis c virus infection after the drug resistance of the patient, and/or prevention of drug-resistant patient disease onset or recurrence of the application of the medicament. The invention of the formula 1 compound has good medicine chest activity of HCV.

Synthesis method of sofosbuvir

-

, (2017/07/19)

The invention provides a synthesis method of sofosbuvir. The synthesis method of the sofosbuvir comprises the following steps: performing mitsunobu reaction on ((2R,3R,4R)-3-benzoyloxy)-4-fluorine-5-hydroxyl-4-methyltetrahydrofuran-2-yl)methyl benzoate to produce sulfonate to obtain a compound 1; abutting the compound 1 and N-benzoylcytosine to produce a compound 2. The method adopts mitsunobu reaction to avoid production of an isomer, and the isomer is reduced to 5 percent or below; according to the method, sulfonate and N-benzoylcytosine are abutted, so the use ofa stannic chloride raw material is avoided; furthermore, the yield is high and few solid waste is generated during aftertreatment, so that the method is suitable for large-scale industrialized production.

Process route upstream and downstream products

Process route

2′,3′,5′-tri-O-benzoyl-2′-C-methyluridine
23643-36-9

2′,3′,5′-tri-O-benzoyl-2′-C-methyluridine

(2‘R)-2‘-deoxy-2’-fluoro-2-methyluridine-3’,5’-dibenzoate
863329-65-1

(2‘R)-2‘-deoxy-2’-fluoro-2-methyluridine-3’,5’-dibenzoate

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: potassium carbonate; phosphoramide / 150 °C
2: tetrabutyl ammonium fluoride / chlorobenzene / Reflux
With tetrabutyl ammonium fluoride; potassium carbonate; phosphoramide; In chlorobenzene;
(2R,3R,4R,5R)-5-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-2-((benzoyloxy)methyl)-4-fluoro-4-methyltetrahydrofuran-3-yl benzoate
817204-32-3

(2R,3R,4R,5R)-5-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-2-((benzoyloxy)methyl)-4-fluoro-4-methyltetrahydrofuran-3-yl benzoate

(2‘R)-2‘-deoxy-2’-fluoro-2-methyluridine-3’,5’-dibenzoate
863329-65-1

(2‘R)-2‘-deoxy-2’-fluoro-2-methyluridine-3’,5’-dibenzoate

Conditions
Conditions Yield
With formic acid; In water; at 25 - 100 ℃; for 7.5h;
93%
With acetic acid; In water; Reflux;
91.4%
With acetic acid; In water; Reflux;
91%
With acetic acid; In water; at 110 ℃; for 5h;
90%
With water; acetic acid; Reflux;
90%
With acetic acid; In water; at 110 ℃; for 20h;
88%
With acetic acid; In water; at 110 ℃; for 20h; Reflux;
88%
With acetic acid; for 12h; Heating;
87%
With acetic acid; In water; at 120 - 140 ℃; Large scale;
85.41%
With acetic acid; In water; at 120 - 140 ℃; Large scale;
85.41%
With acetic acid; In water; at 90 - 105 ℃;
With acetic acid; In water; for 20h; Reflux;
75 g
N<SUP>4</SUP>-benzoyl-3',5'-di-O-benzoyl-2'-deoxy-2'-fluoro-2'-C-methylcytidine

N4-benzoyl-3',5'-di-O-benzoyl-2'-deoxy-2'-fluoro-2'-C-methylcytidine

3',5'-di-O-benzoyl-2'-deoxy-2'-fluoro-2'-C-methyluridine
863329-65-1

3',5'-di-O-benzoyl-2'-deoxy-2'-fluoro-2'-C-methyluridine

Conditions
Conditions Yield
With acetic acid; In water; at 110 ℃; for 5h;
90%
3',5'-O-dibenozyl-2'deoxy-2'-fluoro-2'-C-methyl-N<sub>4</sub>-benzoylcytidine

3',5'-O-dibenozyl-2'deoxy-2'-fluoro-2'-C-methyl-N4-benzoylcytidine

(2‘R)-2‘-deoxy-2’-fluoro-2-methyluridine-3’,5’-dibenzoate
863329-65-1

(2‘R)-2‘-deoxy-2’-fluoro-2-methyluridine-3’,5’-dibenzoate

Conditions
Conditions Yield
With water; acetic acid; at 110 ℃; for 20h;
88%
1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-2-C-methyl-D-ribofuranose
914912-73-5

1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-2-C-methyl-D-ribofuranose

(2‘R)-2‘-deoxy-2’-fluoro-2-methyluridine-3’,5’-dibenzoate
863329-65-1

(2‘R)-2‘-deoxy-2’-fluoro-2-methyluridine-3’,5’-dibenzoate

Conditions
Conditions Yield
uracil; With N,O-bis-(trimethylsilyl)-acetamide; In chlorobenzene; for 0.5h; Reflux;
1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-2-C-methyl-D-ribofuranose; With tin(IV) chloride; In chlorobenzene; Reagent/catalyst; Reflux;
86.5%
((2R,3R,4S,5R)-3-(benzoyloxy)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-hydroxy-4-methyltetrahydrofuran-2-yl)methyl benzoate
944476-44-2

((2R,3R,4S,5R)-3-(benzoyloxy)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-hydroxy-4-methyltetrahydrofuran-2-yl)methyl benzoate

(2‘R)-2‘-deoxy-2’-fluoro-2-methyluridine-3’,5’-dibenzoate
863329-65-1

(2‘R)-2‘-deoxy-2’-fluoro-2-methyluridine-3’,5’-dibenzoate

C<sub>24</sub>H<sub>22</sub>N<sub>2</sub>O<sub>8</sub>
944476-44-2

C24H22N2O8

C<sub>24</sub>H<sub>22</sub>N<sub>2</sub>O<sub>8</sub>

C24H22N2O8

Conditions
Conditions Yield
With triethylamine tris(hydrogen fluoride); triethylamine; ethanaminium,N-(difluoro-λ4-sulfanylidene)-N-ethyl-,tetrafluoroborate; In dichloromethane; at -80 - 40 ℃; for 20h; Inert atmosphere;
12 %Chromat.
((2R,3R,4S,5R)-3-(benzoyloxy)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-hydroxy-4-methyltetrahydrofuran-2-yl)methyl benzoate
944476-44-2

((2R,3R,4S,5R)-3-(benzoyloxy)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-hydroxy-4-methyltetrahydrofuran-2-yl)methyl benzoate

(2‘R)-2‘-deoxy-2’-fluoro-2-methyluridine-3’,5’-dibenzoate
863329-65-1

(2‘R)-2‘-deoxy-2’-fluoro-2-methyluridine-3’,5’-dibenzoate

C<sub>24</sub>H<sub>22</sub>N<sub>2</sub>O<sub>8</sub>
944476-44-2

C24H22N2O8

C<sub>24</sub>H<sub>22</sub>N<sub>2</sub>O<sub>8</sub>

C24H22N2O8

C<sub>24</sub>H<sub>20</sub>N<sub>2</sub>O<sub>7</sub>

C24H20N2O7

Conditions
Conditions Yield
With diethylamino-sulfur trifluoride; In dichloromethane; at -78 ℃; for 1h; Inert atmosphere;
20 %Chromat.
42 %Chromat.
C<sub>24</sub>H<sub>20</sub>N<sub>2</sub>O<sub>7</sub>
944476-43-1

C24H20N2O7

(2‘R)-2‘-deoxy-2’-fluoro-2-methyluridine-3’,5’-dibenzoate
863329-65-1

(2‘R)-2‘-deoxy-2’-fluoro-2-methyluridine-3’,5’-dibenzoate

Conditions
Conditions Yield
With tetrabutyl ammonium fluoride; In chlorobenzene; Solvent; Reagent/catalyst; Reflux;
1.3 g
((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate
874638-80-9,1033394-94-3

((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate

(2‘R)-2‘-deoxy-2’-fluoro-2-methyluridine-3’,5’-dibenzoate
863329-65-1

(2‘R)-2‘-deoxy-2’-fluoro-2-methyluridine-3’,5’-dibenzoate

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / -20 °C / Inert atmosphere
2.1: dmap / 1.5 h / -20 °C / Inert atmosphere
3.1: N,O-bis-(trimethylsilyl)-acetamide / chlorobenzene / 2 h / 80 °C
3.2: 16 h / 65 °C
4.1: acetic acid / water / 5 h / 110 °C
With dmap; N,O-bis-(trimethylsilyl)-acetamide; acetic acid; lithium tri-t-butoxyaluminum hydride; In tetrahydrofuran; water; chlorobenzene;
Multi-step reaction with 4 steps
1: sodium bis(2-methoxyethoxy)aluminium dihydride / dichloromethane / -20 - -15 °C / Inert atmosphere
2: N-ethyl-N,N-diisopropylamine / toluene / 1 h / -5 - 0 °C
3: tin(IV) chloride; N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / Reflux
4: acetic acid / water / 90 - 105 °C
With N,O-bis-(trimethylsilyl)-acetamide; tin(IV) chloride; acetic acid; N-ethyl-N,N-diisopropylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; In dichloromethane; water; toluene; acetonitrile;
Multi-step reaction with 3 steps
1.1: Red-Al(OCH2CF3) / dichloromethane / 0.5 h / -10 °C
1.2: 16 h / -10 - 20 °C
2.1: ammonium sulfate / chlorobenzene / 1.5 h / 20 °C
2.2: 10 h / 70 °C
3.1: acetic acid / water / 20 h / Reflux
With ammonium sulfate; acetic acid; In dichloromethane; water; chlorobenzene;
Multi-step reaction with 4 steps
1: diisobutylaluminium hydride / dichloromethane / 2.5 h / Inert atmosphere
2: N-chloro-succinimide; triphenylphosphine / dichloromethane / 1 h / 0 - 15 °C / Inert atmosphere
3: tin(IV) chloride / chlorobenzene / 75 °C
4: formic acid / water / 7.5 h / 25 - 100 °C
With N-chloro-succinimide; formic acid; tin(IV) chloride; diisobutylaluminium hydride; triphenylphosphine; In dichloromethane; water; chlorobenzene;
Multi-step reaction with 4 steps
1.1: aluminium / dichloromethane; 2,2,2-trifluoroethanol; toluene / 0 - 10 °C
2.1: triphenylphosphine; diethylazodicarboxylate / toluene / 0 - 30 °C
3.1: ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane / chlorobenzene / 90 - 100 °C
3.2: 65 - 70 °C
4.1: acetic acid / water / Reflux
With ammonium sulfate; acetic acid; triphenylphosphine; 1,1,1,3,3,3-hexamethyl-disilazane; aluminium; diethylazodicarboxylate; In dichloromethane; 2,2,2-trifluoroethanol; water; chlorobenzene; toluene; 2.1: |Mitsunobu Displacement;
((2R,3R,4R)-3-(benzoyloxy)-4-fluoro-5-hydroxy-4-methyltetrahydrofuran-2-yl)methyl benzoate

((2R,3R,4R)-3-(benzoyloxy)-4-fluoro-5-hydroxy-4-methyltetrahydrofuran-2-yl)methyl benzoate

(2‘R)-2‘-deoxy-2’-fluoro-2-methyluridine-3’,5’-dibenzoate
863329-65-1

(2‘R)-2‘-deoxy-2’-fluoro-2-methyluridine-3’,5’-dibenzoate

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1.1: dmap / 1.5 h / -20 °C / Inert atmosphere
2.1: N,O-bis-(trimethylsilyl)-acetamide / chlorobenzene / 2 h / 80 °C
2.2: 16 h / 65 °C
3.1: acetic acid / water / 5 h / 110 °C
With dmap; N,O-bis-(trimethylsilyl)-acetamide; acetic acid; In water; chlorobenzene;
Multi-step reaction with 3 steps
1: N-ethyl-N,N-diisopropylamine / toluene / 1 h / -5 - 0 °C
2: tin(IV) chloride; N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / Reflux
3: acetic acid / water / 90 - 105 °C
With N,O-bis-(trimethylsilyl)-acetamide; tin(IV) chloride; acetic acid; N-ethyl-N,N-diisopropylamine; In water; toluene; acetonitrile;
Multi-step reaction with 3 steps
1: N-chloro-succinimide; triphenylphosphine / dichloromethane / 1 h / 0 - 15 °C / Inert atmosphere
2: tin(IV) chloride / chlorobenzene / 75 °C
3: formic acid / water / 7.5 h / 25 - 100 °C
With N-chloro-succinimide; formic acid; tin(IV) chloride; triphenylphosphine; In dichloromethane; water; chlorobenzene;

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