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817204-32-3

817204-32-3

Identification

  • Product Name:Cytidine, N-benzoyl-2'-deoxy-2'-fluoro-2'-methyl-, 3',5'-dibenzoate, (2'R)-

  • CAS Number: 817204-32-3

  • EINECS:

  • Molecular Weight:571.562

  • Molecular Formula: C31H26FN3O7

  • HS Code:

  • Mol File:817204-32-3.mol

Synonyms:N4-benzoyl-3',5'-di-O-benzoyl-2'-fluoro-2'-C-methylcytidine;3',5'-di-O-trityluridine;3',5'-Di-O-Trityl-uridin;O3',O5'-ditrityl-uridine;3',5'-O-ditrityluridine;3',5'-Bis-triphenylmethyl-pyrimidin-ribosid;3',5'-ditrityluridine;4-(Benzoylamino)-1-[5-O-benzoyl-2-deoxy-2-fluoro-2-methyl-3-O-(ph enoxycarbonyl)-β-D-xylofuranosyl]-2(1H)-pyrimidinone;N4,3',5'-tri-O-benzoyl-2'-deoxy-2'-fluoro-2'-C-methylcytidine;

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Safety information and MSDS view more

  • Signal Word:Warning

  • Hazard Statement:H371 May cause damage to organs

  • 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

  • Manufacture/Brand
  • Product Description
  • Packaging
  • Price
  • Delivery
  • Purchase
  • Manufacture/Brand:TRC
  • Product Description:2’-Defluro-2’-methyleneSofosbuvir
  • Packaging:1mg
  • Price:$ 95
  • Delivery:In stock
  • Buy Now
  • Manufacture/Brand:TRC
  • Product Description:(2''R)-N-Benzoyl-2''-deoxy-2''-fluoro-2''-methyl-3'',5''-dibenzoateCytidine
  • Packaging:500mg
  • Price:$ 85
  • Delivery:In stock
  • Buy Now
  • Manufacture/Brand:TRC
  • Product Description:2’-Defluro-2’-methyleneSofosbuvir
  • Packaging:5mg
  • Price:$ 425
  • Delivery:In stock
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  • Manufacture/Brand:Crysdot
  • Product Description:(2R,3R,4R,5R)-5-(4-Benzamido-2-oxopyrimidin-1(2H)-yl)-2-((benzoyloxy)methyl)-4-fluoro-4-methyltetrahydrofuran-3-ylbenzoate 95+%
  • Packaging:100g
  • Price:$ 386
  • Delivery:In stock
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  • Manufacture/Brand:ChemScene
  • Product Description:Cytidine,N-benzoyl-2'-deoxy-2'-fluoro-2'-methyl-,3',5'-dibenzoate,(2'R)-
  • Packaging:10g
  • Price:$ 58
  • Delivery:In stock
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  • Manufacture/Brand:ChemScene
  • Product Description:Cytidine,N-benzoyl-2'-deoxy-2'-fluoro-2'-methyl-,3',5'-dibenzoate,(2'R)-
  • Packaging:100g
  • Price:$ 349
  • Delivery:In stock
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  • Manufacture/Brand:ChemScene
  • Product Description:Cytidine,N-benzoyl-2'-deoxy-2'-fluoro-2'-methyl-,3',5'-dibenzoate,(2'R)-
  • Packaging:25g
  • Price:$ 108
  • Delivery:In stock
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  • Manufacture/Brand:Chemenu
  • Product Description:[(2R,3R,4R,5R)-5-(4-benzamido-2-oxo-1,2-dihydropyrimidin-1-yl)-3-(benzoyloxy)-4-fluoro-4-methyloxolan-2-yl]methylbenzoate 95%
  • Packaging:100g
  • Price:$ 473
  • Delivery:In stock
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  • Manufacture/Brand:American Custom Chemicals Corporation
  • Product Description:[(2R,3R,4R,5R)-5-(4-BENZAMIDO-2-OXO-1,2-DIHYDROPYRIMIDIN-1-YL)-3-(BENZOYLOXY)-4-FLUORO-4-METHYLOXOLAN-2-YL]METHYL BENZOATE 95.00%
  • Packaging:5MG
  • Price:$ 458.68
  • Delivery:In stock
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  • Manufacture/Brand:Ambeed
  • Product Description:(2R,3R,4R,5R)-5-(4-Benzamido-2-oxopyrimidin-1(2H)-yl)-2-((benzoyloxy)methyl)-4-fluoro-4-methyltetrahydrofuran-3-ylbenzoate 97%
  • Packaging:25g
  • Price:$ 55
  • Delivery:In stock
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Relevant articles and documentsAll total 22 Articles be found

Preparation method of intermediate

-

, (2021/09/08)

The invention relates to the technical field of biological pharmacy. More specifically, the compound shown in Formula -3 - is prepared by reacting a compound represented by Formula -4 - with a modified 4R red aluminum, and then subjecting the compound of

Method for preparing sofosbuvir intermediate by using continuous flow micro-channel reactor

-

Paragraph 0033-0046, (2020/07/02)

The invention discloses a process method for preparing (2 'R)-N-benzoyl-2'-deoxy-2'-fluoro-2'-methylcytidyl-3 ', 5 '-dibenzoate, and belongs to the technical field of organic synthesis application, the process method is a novel process method for preparing a target product within reaction time of dozens of seconds from (2R, 3R, 4R, 5R)-3-(benzoyloxy)-5-chloro-4-fluoro-4-methyltetrahydrofuran-2-yl)methyl benzoate as a raw material in a continuous flow micro-channel reactor and stannic chloride as a catalyst by introducing materials into the reactor through a counting pump, heating, mixing andreacting to obtain a product; the method has the characteristics of simplicity and safety in operation, high yield and short reaction time, and can realize continuous production; the yield of the product is 55% or above, and the purity reaches 99%.

A preparation process of rope non-cloth wei improved method

-

Paragraph 0008, (2019/03/28)

The invention provides a method for improving technique of rope non-cloth wei, for the oxidation of olefinic bond when [...], the oxidizing agent is potassium permanganate into sodium permanganate, product yield from 78% improved to 90% or more; in cytosine with halo ethylthio butt coupling reaction using tin tetrachloride to replace the zinc chloride catalytic, yield from 75% to a 88%; using five fluoro phenol instead of the nitro phenol to prepare phosphoric acid ester side chain, so that the phosphoric acid ester side chain of the yield from 80% up to 95%.

Stereoselective N-glycosylation with N4-acyl cytosines and efficient synthesis of gemcitabine

Liu, Tongchao,Tang, Jiadeng,Liang, Jianpeng,Chen, Yabin,Wang, Xiaowen,Shen, Jingkang,Zhao, Dongmei,Xiong, Bing,Cen, Jun-Da,Chen, Yue-Lei

, p. 1203 - 1213 (2019/01/29)

Through systematical comparison of various N4-protected cytosine derivatives in the glycosylation step of gemcitabine synthesis, highly beta-stereoselective and high yielding TBAI catalyzed N-glycosylation was achieved with N4-Bz cytosine and anomeric mixture of 2,2‘-difluororibose mesylate donor. The subsequent global deprotection gave gemcitabine efficiently. Meanwhile, the anomeric chloride intermediate and fluoride-displaced side products of this N-glycosylation were identified, too. This new glycosylation method reveals the importance of N4-protection in the stereoselective preparation of pyrimidine nucleoside, also provides a potential alternative to current industrial process to gemcitabine.

Technology for preparing sofosbuvir intermediate

-

, (2018/04/02)

A technology for preparing a sofosbuvir intermediate represented by formula 1 comprises the following steps: (a) reducing a compound 2 by sodium borohydride to generate a compound 3; (b) reacting thecompound 3 with a methanol-hydrochloric acid solution to generate a compound 4; (c) carrying out a fluorination reaction on the compound 4 and a fluorination reagent in a reaction solvent at -10 to -65 DEG C under the protection of nitrogen, and post-treating a reaction solution after the reaction is fully carried out in order to obtain a compound 5; (d) cooling an n-hexane or petroleum ether or cyclohexane solution of the compound 5 to -5-5 DEG C under the protection of nitrogen, adding thionyl chloride, slowly dropwise adding methanol or ethanol at a controlled temperature of -5-5 DEG C, rising the temperature to 10-40 DEG C after the dropwise addition, continuously performing stirring until the reaction is completed , and removing the solvent to obtain a compound 6; and (e) condensing the compound 6 and a compound 7, and carrying out hydrolysis treatment to obtain the target product which is the compound 1. The preparation technology has the characteristics of high yield, convenience and safety in operation, less discharge of three wastes, low production cost, and suitableness for industrial production.

Process route upstream and downstream products

Process route

(2R)-2-deoxy-2-fluoro-2-methyl-α/β-D-erythro-pentofuranosyl chloride-3,5-dibenzoate
1500076-79-8

(2R)-2-deoxy-2-fluoro-2-methyl-α/β-D-erythro-pentofuranosyl chloride-3,5-dibenzoate

N-(2-Trimethylsilanyloxy-pyrimidin-4-yl)-benzamide
85743-99-3

N-(2-Trimethylsilanyloxy-pyrimidin-4-yl)-benzamide

(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

Conditions
Conditions Yield
(2R)-2-deoxy-2-fluoro-2-methyl-α/β-D-erythro-pentofuranosyl chloride-3,5-dibenzoate; N-(2-Trimethylsilanyloxy-pyrimidin-4-yl)-benzamide; In chlorobenzene; at 23 ℃; for 0.25h;
With tin(IV) chloride; In chlorobenzene; at 50 - 60 ℃; for 18h;
72.5%
With tin(IV) chloride; In chlorobenzene; at 75 ℃;
65%
(2R)-2-deoxy-2-fluoro-2-methyl-α/β-D-erythro-pentofuranosyl chloride-3,5-dibenzoate; N-(2-Trimethylsilanyloxy-pyrimidin-4-yl)-benzamide; With tin(IV) chloride; In chlorobenzene; at 70 ℃; for 10h;
With water; sodium hydrogencarbonate; In dichloromethane; chlorobenzene; at 10 - 45 ℃; for 0.5h;
(2R)-2-deoxy-2-fluoro-2-methyl-α/β-D-erythro-pentofuranosyl chloride-3,5-dibenzoate; N-(2-Trimethylsilanyloxy-pyrimidin-4-yl)-benzamide; With tin(IV) chloride; In dichloromethane; at 30 - 80 ℃; for 20h; under 1875.19 Torr; Sealed tube;
With acetic acid; In dichloromethane; water; at 18 - 25 ℃;
34.9 g
(2R)-2-deoxy-2-fluoro-2-methyl-α/β-D-erythro-pentofuranosyl chloride-3,5-dibenzoate; N-(2-Trimethylsilanyloxy-pyrimidin-4-yl)-benzamide; With tin(IV) chloride; In dichloromethane; at 75 - 80 ℃; for 20h; under 1875.19 Torr;
With acetic acid; In dichloromethane; water; at 18 - 25 ℃;
34.9 g
((2R,3R,4R,5R)-3-(benzoyloxy)-5-chloro-4-fluoro-4-methyltetrahydrofuran-2-yl)methylbenzoate

((2R,3R,4R,5R)-3-(benzoyloxy)-5-chloro-4-fluoro-4-methyltetrahydrofuran-2-yl)methylbenzoate

N-(2-Trimethylsilanyloxy-pyrimidin-4-yl)-benzamide
85743-99-3

N-(2-Trimethylsilanyloxy-pyrimidin-4-yl)-benzamide

(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

Conditions
Conditions Yield
With tin(IV) chloride; acetic acid; In dichloromethane; chlorobenzene; at 70 - 85 ℃; for 0.0166667h; under 750.075 - 2250.23 Torr; Reagent/catalyst; Temperature; Pressure;
72%
C<sub>31</sub>H<sub>28</sub>FN<sub>3</sub>O<sub>7</sub>

C31H28FN3O7

(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

Conditions
Conditions Yield
With manganese(IV) oxide; In toluene; at 20 ℃; for 2h;
84%
4-N-benzoylcytosine
26661-13-2

4-N-benzoylcytosine

C<sub>21</sub>H<sub>21</sub>FO<sub>8</sub>S

C21H21FO8S

(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

Conditions
Conditions Yield
4-N-benzoylcytosine; With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane; In chlorobenzene; at 90 - 100 ℃;
C21H21FO8S; With 2,6-dimethylpyridine; In chlorobenzene; at 65 - 70 ℃; Temperature;
67.4%
(2R)-2-deoxy-2-fluoro-2-methyl-α/β-D-erythro-pentofuranosyl chloride-3,5-dibenzoate
1500076-79-8

(2R)-2-deoxy-2-fluoro-2-methyl-α/β-D-erythro-pentofuranosyl chloride-3,5-dibenzoate

N<sub>4</sub>-benzoylcitosine
26661-13-2

N4-benzoylcitosine

(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

Conditions
Conditions Yield
With ammonium sulfate; tin(IV) chloride; 1,1,1,3,3,3-hexamethyl-disilazane; In chlorobenzene; at 85 - 135 ℃; Reflux;
57.3%
(2R)-2-deoxy-2-fluoro-2-methyl-α/β-D-erythro-pentofuranosyl chloride-3,5-dibenzoate
1500076-79-8

(2R)-2-deoxy-2-fluoro-2-methyl-α/β-D-erythro-pentofuranosyl chloride-3,5-dibenzoate

N<sub>4</sub>,O-bis(trimethylsilyl)-N<sub>4</sub>-benzoylcytosine
64339-87-3

N4,O-bis(trimethylsilyl)-N4-benzoylcytosine

(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

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

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

Conditions
Conditions Yield
With tin(IV) chloride; tetra-(n-butyl)ammonium iodide; In chlorobenzene; at 80 ℃; for 16h; Inert atmosphere;
57%
13%
((2R,3R,4R,5R)-3-(benzoyloxy)-5-chloro-4-fluoro-4-methyltetrahydrofuran-2-yl)methyl benzoate
1199809-23-8,1500076-79-8

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

N-(2-Trimethylsilanyloxy-pyrimidin-4-yl)-benzamide
85743-99-3

N-(2-Trimethylsilanyloxy-pyrimidin-4-yl)-benzamide

(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

Conditions
Conditions Yield
With tin(IV) chloride; In dichloromethane; at 75 - 80 ℃; for 20h; Autoclave;
37.2%
N<sup>4</sup>-benzoyl-1-(2-C-methyl-3,5-di-O-benzoyl-β-D-arabinofuranosyl)cytosine
863329-62-8,863329-64-0

N4-benzoyl-1-(2-C-methyl-3,5-di-O-benzoyl-β-D-arabinofuranosyl)cytosine

(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

Conditions
Conditions Yield
With diethylamino-sulfur trifluoride;
19%
With diethylamino-sulfur trifluoride; at -20 ℃; for 1h; Inert atmosphere;
16.3%
4-N-benzoylcytosine
26661-13-2

4-N-benzoylcytosine

(2R,3R,4R)-3-(benzoyloxy)-4-fluoro-5-(methanesulfonyloxy)-4-methyloxolan-2-yl benzoate

(2R,3R,4R)-3-(benzoyloxy)-4-fluoro-5-(methanesulfonyloxy)-4-methyloxolan-2-yl benzoate

(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

Conditions
Conditions Yield
With potassium carbonate; In ethyl acetate; at 80 ℃;
28.3 g
C<sub>11</sub>H<sub>9</sub>N<sub>3</sub>O<sub>2</sub>

C11H9N3O2

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

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

(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

Conditions
Conditions Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene; In ethyl acetate; at 64 ℃; for 3h; Temperature;
33.2 g

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