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61676-62-8

61676-62-8

Identification

  • Product Name:1,3,2-Dioxaborolane,4,4,5,5-tetramethyl-2-(1-methylethoxy)-

  • CAS Number: 61676-62-8

  • EINECS:-0

  • Molecular Weight:186.059

  • Molecular Formula: C9H19BO3

  • HS Code:29209090

  • Mol File:61676-62-8.mol

Synonyms:Boric acid,cyclic tetramethylethylene isopropyl ester (7CI);2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;4,4,5,5-tetramethyl-2-(1-methylethoxy)-1,3,2-dioxaborolane;Isopropoxy4,4,5,5-Tetramethyl-1,3,2-dioxaborolane;Isopropyl pinacol borate;Isopropoxyboronic acid pinacol ester;

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Safety information and MSDS view more

  • Pictogram(s):IrritantXi

  • Hazard Codes:Xi

  • Signal Word:Warning

  • Hazard Statement:H226 Flammable liquid and vapour

  • 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

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  • Manufacture/Brand:TRC
  • Product Description:2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
  • Packaging:5g
  • Price:$ 45
  • Delivery:In stock
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  • Manufacture/Brand:TCI Chemical
  • Product Description:2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane >98.0%(GC)(T)
  • Packaging:100g
  • Price:$ 127
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  • Manufacture/Brand:TCI Chemical
  • Product Description:2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane >98.0%(GC)(T)
  • Packaging:5g
  • Price:$ 10
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  • Manufacture/Brand:TCI Chemical
  • Product Description:2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane >98.0%(GC)(T)
  • Packaging:25g
  • Price:$ 33
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  • Manufacture/Brand:Synthonix
  • Product Description:4,4,5,5-tetramethyl-2-(propan-2-yloxy)-1,3,2-dioxaborolane 97.0%
  • Packaging:100g
  • Price:$ 40
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:Isopropoxyboronic acid, pinacol ester
  • Packaging:500 g
  • Price:$ 279
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:Isopropoxyboronic acid, pinacol ester
  • Packaging:25 g
  • Price:$ 24
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:Isopropoxyboronic acid, pinacol ester
  • Packaging:100 g
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 98%
  • Packaging:5ml
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 98%
  • Packaging:500ml
  • Price:$ 607
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Relevant articles and documentsAll total 27 Articles be found

A study of the effect on nucleophilic hydrolytic activity of pancreatic elastase, trypsin, chymotrypsin, and leucine aminopeptidase by boronic acids in the presence of arabinogalactan: A subsequent study on the hydrolytic activity of chymotrypsin by boronic acids in the presence of mono-, di-, and trisaccharides

Smoum, Reem,Rubinstein, Abraham,Srebnik, Morris

, p. 464 - 474 (2003)

The hydrolytic activity of trypsin, chymotrypsin, elastase, and leucine aminopeptidase, is inhibited by different boronic acids. However, all the enzymes are inhibited by the compound CbzAla(boro)Gly(OH)2. Therefore, these additives can control the nucleophilic hydrolytic activity of these enzymes.

Synthesis and stability of new spiroaminoborate esters

Stepanenko, Viatcheslav,De Jesús, Melvin,Garcia, Carmelo,Barnes, Charles L.,Ortiz-Marciales, Margarita

, p. 910 - 913 (2012)

New spiroaminoborate esters derived from 1,1-diphenylprolinol, ephedrine, and dihydroquinine with different alkoxy substituents were prepared as stable crystalline compounds and characterized by spectroscopical analysis and specific rotation. The structure of the spiroborate 4 derived from 1,1-diphenylprolinol and dicyclohexyl-1,1′-diol was confirmed by X-ray analysis.

Hydroboration of nitriles, esters, and amides catalyzed by simple neosilyllithium

Bandyopadhyay, Ayan,Bhattacharjee, Jayeeta,Kumar Singh, Saurabh,Kumari, Kusum,Moorthy, Shruti,Panda, Tarun K.,Sai Kumar, Gobbilla

supporting information, (2022/03/31)

We present here an efficient method for the hydroboration of organic nitriles, carboxylic esters, and carboxamides with pinacolborane (HBpin) using an alkali metal catalyst, neosilyllithium (LiCH2SiMe3), in neat reaction conditions. The reactions were accomplished with efficient catalytic reactivity and demonstrated by neosilyllithium at room temperature, in solvent-free condition, to afford a high yield of the corresponding N-boryl amines, boryl ethers, and amine hydrochlorides. The protocol for the catalytic reaction presented in this paper is simple and efficient, with diverse substrate scope for nitriles, carboxylic esters, and carboxamides showing excellent functional group tolerance. DLPNO-CCSD(T) calculations were also performed, showing that the hydroboration of nitriles catalyzed by neosilyllithium occurs through the pre-coordination of the nitrile at Lewis acid lithium followed by hydride migration from the B–H entity.

Catalytic hydroboration of carbonyl derivatives by using phosphinimino amide ligated magnesium complexes

Cui, Dongmei,Li, Min,Liu, Xinli

supporting information, p. 13037 - 13041 (2021/10/12)

Reduction of carbonyl derivatives by using Earth-abundant, cheap, and environmentally benign metal-based catalysts through an atom-efficient method is a challenging task. Herein, we report the synthesis and characterization of dinuclear magnesium complexes 1-3 chelated by a phosphinimino amide skeleton. In combination with pinacolborane (HBpin) as a reducing agent, complex 1 bearing an ortho-methyl substituent on the phenyl ring of the ligand showed excellent reduction capability for a broad range of carbonyl derivatives under mild reaction conditions. Aldehydes, ketones, and acrolein substrates were efficiently reduced to the corresponding alkoxy-borane products with a record high TOF. Besides, acrolein derivatives were exclusively reduced to 1,2-regioselective products. Using two equiv. of HBpin, ester substrates were reduced to two kinds of alkoxy-borane products. Carbonate reduction accomplished by using complex 1 and three equiv. of HBpin afforded diols and a methanol precursor, respectively. When chiral substrates such as (S)-1,2-propanediol carbonate and l-lactide or polymeric P(l-LA) were employed, the chirality was almost retained in their reductive products.

Hydroboration of aldehydes, ketones and CO2under mild conditions mediated by iron(iii) salen complexes

James, Alexander P.,Lau, Samantha,Provis-Evans, Cei B.,Webster, Ruth L.

supporting information, p. 10696 - 10700 (2021/08/17)

The hydroboration of aldehydes, ketones and CO2is demonstrated using a cheap and air stable [Fe(salen)]2-μ-oxo pre-catalyst with pinacolborane (HBpin) as the reductant under mild conditions. This catalyst system chemoselectively hydroborates aldehydes over ketones and ketones over alkenes. In addition, the [Fe(salen)2]-μ-oxo pre-catalyst shows good efficacy at reducing “wet” CO2with HBpin at room temperature.

Nucleophilic Addition and α-C-H Substitution Reactions of an Imine Mediated by Dibutylmagnesium and Organolithium Reagents

Dang, Yan,Jia, Chaohong,Li, Yafei,Li, Yahong,Lu, Yanhua,Wang, Yalan,Xia, Yuanzhi,Xu, Man,Zhang, Liang

, (2021/07/17)

A series of nucleophilic addition reactions and α-C-H substitution reactions of an imine-containing ligand 2-(2-((((1H-pyrrol-2-yl)methylene)amino)methyl)-1H-pyrrol-1-yl)-N,N-dimethylethan-1-amine (HL1) were reported. The reactions of HL1 with 0.5 and 2 equiv ofnBu2Mg, respectively, gave two complexes of compositions [Mg(L1)2] (1) and [Mg2(L2)2] (2) (H2L2 =N-((1-(2-(dimethylamino)ethyl)-1H-pyrrol-2-yl)methyl)-1-(1H-pyrrol-2-yl)pentan-1-amine). The nucleophilic addition ofnBu2Mg to the C═N bond of the HL1 ligand occurred in the process for the formation of2. Treatment of HL1 with 2 and 1 equiv ofnBuLi generated [Li2(L3)2] (3) (HL3 = 2-(2-(((1-(1H-pyrrol-2-yl)pentylidene)amino)methyl)-1H-pyrrol-1-yl)-N,N-dimethylethan-1-amine) and [Li2(L1)2] (4). An α-C-H substitution of the HC═NR moiety of the HL1 ligand triggered bynBuLi was discovered in the preparation of3. The formation of3demonstrates a new concept for the C-C coupling that involved inert C-H bond activation of HC═NR skeleton. The reactions of HL1 with MeLi,sec-BuLi, and tert-BuLi, respectively, were also examined. The products for both the nucleophilic addition of organolithium reagents to the C═N bond and α-C-H substitution of the HC═NR moiety of the HL1 ligand were determined. The mechanisms for the formations of2and3were rationalized by DFT calculations. The hydroboration reactions catalyzed by2were investigated, and these reactions characterize ample substrate scope, very good yields, and high selectivity.

Construction of Silicon-Containing Seven-Membered Rings by Catalytic [4 + 2 + 1] Cycloaddition through Rhodium Silylenoid

Sasaki, Ikuo,Ohmura, Toshimichi,Suginome, Michinori

supporting information, p. 2961 - 2966 (2020/04/10)

A rhodium-catalyzed [4 + 2 + 1] cycloaddition involving 1,3-diene, alkyne, and silylene to afford silicon-containing seven-membered rings was established. In the presence of a rhodium catalyst bearing bis(diphenylphosphino)methane (DPPM), nona-1,3-dien-8-yne derivatives reacted efficiently at 80-110 °C with boryl(isopropoxy)silane or boryl(diethyamino)silane, which reacts as the synthetic equivalent of silylene, to afford 1-silacyclohepta-2,5-dienes (2,5-dihydro-1H-silepines). Regiodivergent and chemo- and stereoselective functionalization of the seven-membered nonconjugated diene was achieved by hydroboration mediated by Cs2CO3 or an iridium catalyst.

Process route upstream and downstream products

Process route

2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

Triisopropyl borate
5419-55-6

Triisopropyl borate

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
61676-62-8

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions
Conditions Yield
In hexane;
92%
In hexane; Heating;
92%
at 90 ℃;
90%
In hexane; byproducts: (CH3)2CHOH; slowly distn. of a azeotrope i-PrOH/hexane at 55-60°C from a soln. of B(OiPr)3 and pinacol in hexane, solvents removed at 15 Torr, distn. (0.1 Torr, 40°C bath); redistn. of iPrOB(O2C2(CH3)4, elem. anal.;
89%
In hexane; at 55 - 60 ℃;
89%
at 80 - 85 ℃; Inert atmosphere;
87.5%
In hexane; at 55 - 60 ℃;
82%
at 68 ℃; for 2h;
44%
at 115 ℃; for 3h;
at 90 ℃;
In toluene; Inert atmosphere; Reflux;
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

methyloxirane
75-56-9,16033-71-9

methyloxirane

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
61676-62-8

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

2-propoxy-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane
1130-16-1

2-propoxy-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

Conditions
Conditions Yield
With C48H58Mg2N4; In benzene-d6; at 90 ℃; for 8h; Overall yield = 99 %Spectr.; Inert atmosphere; Glovebox;
Triisopropyl borate
5419-55-6

Triisopropyl borate

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
61676-62-8

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions
Conditions Yield
With 2,3-dimethyl-2,3-butane diol; In hexane; at 90 ℃;
86%
Ethyl isobutyrate
97-62-1

Ethyl isobutyrate

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

2-ethoxy-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane
1126-93-8

2-ethoxy-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
61676-62-8

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions
Conditions Yield
With tris(bis(trimethylsilyl)amido)lanthanum(III); In benzene-d6; at 25 ℃; for 0.25h; Overall yield = > 99 percent; Glovebox;
acetone
67-64-1

acetone

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
61676-62-8

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions
Conditions Yield
With H4O8Zr6(12+)*3C14H6O6(4-)*3C14H8O4(2-)*3Ti(4+)*6C3H7O(1-); In hexane; toluene; at 25 ℃; for 24h; Inert atmosphere; Schlenk technique; Glovebox;
63 %Spectr.
With C12H14F3NO4SSn; In toluene; at 43 ℃; for 0.16h; chemoselective reaction; Catalytic behavior; Inert atmosphere; Glovebox;
With C26H38NNiOP; In benzene-d6; at 25 ℃; for 0.0833333h; Catalytic behavior; Inert atmosphere; Sealed tube;
With two-dimensional iron(II) coordination polymer based on a divergent 4'-(4-diphenylamino)phenyl-4,2';6',4''-terpyridine ligand; potassium tert-butylate; In neat (no solvent); at 20 ℃; for 1h; chemoselective reaction; Green chemistry;
99 %Chromat.
With [(i-Bu)2ATIGeOTf]; at 60 ℃; for 5h; Catalytic behavior; Schlenk technique;
With C16H32LiO6(1+)*C32H40AlN4O(1-); In tetrahydrofuran-d8; at 20 ℃; Reagent/catalyst; Catalytic behavior; Inert atmosphere; Schlenk technique;
With (μ-oxo)bis[(1,2-ethanediamino-N,N'-bis(salicylidene))iron(III)]; In [D3]acetonitrile; at 60 ℃; for 24h; Inert atmosphere; Schlenk technique; Glovebox;
46 %Spectr.
With C36H56Mg2N8; In chloroform-d1; at 20 ℃; for 0.5h; Inert atmosphere;
> 99 %Spectr.
2-(isopropoxydimethylsilyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
929887-20-7

2-(isopropoxydimethylsilyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

diethyl (E)-2-(but-2-yn-1-yl)-2-(penta-2,4-dien-1-yl)malonate
222549-37-3

diethyl (E)-2-(but-2-yn-1-yl)-2-(penta-2,4-dien-1-yl)malonate

diethyl 7-methyl-1,3,3a,6-tetrahydro-2H-indene-2,2-dicarboxylate
1009843-86-0

diethyl 7-methyl-1,3,3a,6-tetrahydro-2H-indene-2,2-dicarboxylate

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
61676-62-8

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

diethyl 1,2,2-trimethyl-2,5a,6,8-tetrahydrocyclopenta[c]silepine-7,7(3H)-dicarboxylate

diethyl 1,2,2-trimethyl-2,5a,6,8-tetrahydrocyclopenta[c]silepine-7,7(3H)-dicarboxylate

Conditions
Conditions Yield
With bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; bis-diphenylphosphinomethane; In 1,2-dichloro-ethane; at 80 ℃; for 6h; regioselective reaction; Inert atmosphere; Sealed tube;
8 %Spectr.
68 %Spectr.
51%
2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

isopropoxyboronic acid
52732-22-6

isopropoxyboronic acid

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
61676-62-8

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions
Conditions Yield
Inert atmosphere; Reflux; Large scale reaction;
87.5%
2-(isopropoxydimethylsilyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
929887-20-7

2-(isopropoxydimethylsilyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
61676-62-8

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions
Conditions Yield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; 1,3-bis-(diphenylphosphino)propane; diethyl (E)-2-(but-2-yn-1-yl)-2-(penta-2,4-dien-1-yl)malonate; In 1,2-dichloro-ethane; at 80 ℃; for 6h; Reagent/catalyst; regioselective reaction; Inert atmosphere; Sealed tube;
71%Spectr.
2-(isopropoxydimethylsilyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
929887-20-7

2-(isopropoxydimethylsilyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

diethyl (E)-2-(but-2-yn-1-yl)-2-(penta-2,4-dien-1-yl)malonate
222549-37-3

diethyl (E)-2-(but-2-yn-1-yl)-2-(penta-2,4-dien-1-yl)malonate

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
61676-62-8

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

diethyl 1,2,2-trimethyl-2,5a,6,8-tetrahydrocyclopenta[c]silepine-7,7(3H)-dicarboxylate

diethyl 1,2,2-trimethyl-2,5a,6,8-tetrahydrocyclopenta[c]silepine-7,7(3H)-dicarboxylate

Conditions
Conditions Yield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; bis-diphenylphosphinomethane; In 1,2-dichloro-ethane; at 80 ℃; for 6h; regioselective reaction; Inert atmosphere; Sealed tube;
2-(isopropoxydimethylsilyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
929887-20-7

2-(isopropoxydimethylsilyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

diethyl (E)-2-(but-2-yn-1-yl)-2-(penta-2,4-dien-1-yl)malonate
222549-37-3

diethyl (E)-2-(but-2-yn-1-yl)-2-(penta-2,4-dien-1-yl)malonate

diethyl 7-methyl-1,3,3a,6-tetrahydro-2H-indene-2,2-dicarboxylate
1009843-86-0

diethyl 7-methyl-1,3,3a,6-tetrahydro-2H-indene-2,2-dicarboxylate

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
61676-62-8

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions
Conditions Yield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; 1,5-bis-(diphenylphosphino)pentane; In 1,2-dichloro-ethane; at 80 ℃; for 6h; regioselective reaction; Inert atmosphere; Sealed tube;
6 %Spectr.
51%Spectr.

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