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147959-19-1

147959-19-1

Identification

  • Product Name:3-Oxazolidinecarboxylicacid, 2,2-dimethyl-4-(2-oxoethyl)-, 1,1-dimethylethyl ester, (4S)-

  • CAS Number: 147959-19-1

  • EINECS:

  • Molecular Weight:243.303

  • Molecular Formula: C12H21 N O4

  • HS Code:2934999090

  • Mol File:147959-19-1.mol

Synonyms:3-Oxazolidinecarboxylicacid, 2,2-dimethyl-4-(2-oxoethyl)-, 1,1-dimethylethyl ester, (S)-;1,1-Dimethylethyl (4S)-2,2-dimethyl-4-(2-oxoethyl)oxazolidine-3-carboxylate

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Safety information and MSDS view more

  • Signal Word:no data available

  • Hazard Statement:no data available

  • 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:(S)-Tert-Butyl2,2-Dimethyl-4-(2-Oxoethyl)Oxazolidine-3-Carboxylate
  • Packaging:25mg
  • Price:$ 200
  • Delivery:In stock
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  • Manufacture/Brand:TRC
  • Product Description:(S)-Tert-Butyl2,2-Dimethyl-4-(2-Oxoethyl)Oxazolidine-3-Carboxylate
  • Packaging:5mg
  • Price:$ 60
  • Delivery:In stock
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  • Manufacture/Brand:TRC
  • Product Description:(S)-Tert-Butyl2,2-Dimethyl-4-(2-Oxoethyl)Oxazolidine-3-Carboxylate
  • Packaging:2.5mg
  • Price:$ 45
  • Delivery:In stock
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  • Manufacture/Brand:Labseeker
  • Product Description:(S)-TERT-BUTYL2,2-DIMETHYL-4-(2-OXOETHYL)OXAZOLIDINE-3-CARBOXYLATE 95
  • Packaging:1g
  • Price:$ 585
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  • Manufacture/Brand:Crysdot
  • Product Description:(S)-tert-Butyl2,2-dimethyl-4-(2-oxoethyl)oxazolidine-3-carboxylate 95+%
  • Packaging:250mg
  • Price:$ 475
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  • Manufacture/Brand:American Custom Chemicals Corporation
  • Product Description:(S)-TERT-BUTYL-2,2-DIMETHYL-4-(2-OXOETHYL)OXAZOLIDINE-3-CARBOXYLATE 98.00%
  • Packaging:5MG
  • Price:$ 498.53
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  • Manufacture/Brand:American Custom Chemicals Corporation
  • Product Description:(S)-TERT-BUTYL-2,2-DIMETHYL-4-(2-OXOETHYL)OXAZOLIDINE-3-CARBOXYLATE 98.00%
  • Packaging:0.25G
  • Price:$ 660
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  • Manufacture/Brand:AK Scientific
  • Product Description:(S)-tert-Butyl2,2-dimethyl-4-(2-oxoethyl)oxazolidine-3-carboxylate
  • Packaging:1g
  • Price:$ 1268
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  • Manufacture/Brand:Activate Scientific
  • Product Description:(S)-3-Boc-2,2-dimethyloxazolidine-4-acetaldehyde 95+% ee
  • Packaging:1 g
  • Price:$ 1139
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Relevant articles and documentsAll total 14 Articles be found

Synthesis of sphingosine analogues: Stereoselective synthesis of 3- deoxysphingosine and cis-isomers

Kawate, Tomohiko,Fukuta, Natsuko,Nishida, Atsushi,Nakagawa, Masako

, p. 2116 - 2118 (1997)

Both enantiomers of 3-deoxysphingosine as well as their cis-isomers were synthesized stereoselectively from L- and D-serine.

Bifunctional Tripeptide with a Phosphonic Acid as a Br?nsted Acid for Michael Addition: Mechanistic Insights

Cortes-Clerget, Margery,Jover, Jesús,Dussart, Jade,Kolodziej, Emilie,Monteil, Maelle,Migianu-Griffoni, Evelyne,Gager, Olivier,Deschamp, Julia,Lecouvey, Marc

supporting information, p. 6654 - 6662 (2017/05/15)

Enamine catalysis is a widespread activation mode in the field of organocatalysis and is often encountered in bifunctional organocatalysts. We previously described H-Pro-Pro-pAla-OMe as a bifunctional catalyst for Michael addition between aldehydes and ar

NOVEL QUINOLINE-SUBSTITUTED COMPOUND

-

, (2016/10/10)

An object to be achieved by the present invention is to provide a novel compound having EGFR inhibitory effects and cell growth inhibitory effects, as well as a medication useful for the prevention and/or treatment of cancer based on the EGFR inhibitory effects. The present invention provides a compound represented by Formula (I) below, or a salt thereof.

Expeditious synthesis of enantiopure, orthogonally protected bis-α-amino acids (OPBAAs) and their use in a study of Nod1 stimulation

Chen, Po-Ting,Lin, Cheng-Kun,Tsai, Chih-Ju,Huang, Duen-Yi,Nien, Fu-Yao,Lin, Wan-Wan,Cheng, Wei-Chieh

supporting information, p. 474 - 482 (2015/01/30)

A convenient approach towards the synthesis of orthogonally protected chiral bis-a-amino acids (OPBAAs) is described. The key transformations include: (1) a highly stereoselective conjugation (alkylation) of the Sch?llkopf bislactim ethers and oxazolidinyl alkyl halides to build a backbone skeleton; and (2) our orthogonal protection strategy. A series of enantiopure OPBAAs bearing a variety of alkyl chain as a spacer; two stereogenic centers; and three protecting groups were prepared as examples. These versatile molecules were applied to the synthesis of biologically interesting di- or tri-peptide analogues, including chiral iE-meso-DAP and A-iE-meso-DAP, for the study of Nod1 activation in the innate immune response.

FACTOR XIa INHIBITORS

-

Page/Page column 71, (2015/12/09)

The present invention provides a compound of Formula (I) and pharmaceutical compositions comprising one or more said compounds, and methods for using said compounds for treating or preventing thromboses, embolisms, hypercoagulability or fibrotic changes. The compounds are selective Factor XIa inhibitors or dual inhibitors of Factor XIa and plasma kallikrein.

Chemo-enzymatic synthesis of the azasugars 1,4-dideoxyallonojirimycin and 1,4-dideoxymannojirimycin

Venkataiah, Mallam,Reddipalli, Gowrisankar,Jasti, Lakshmi Swarnalatha,Fadnavis, Nitin W.

, p. 1855 - 1860 (2012/01/13)

The enzymatic resolution of the N-phenylacetyl derivative of racemic homoserine lactone with penicillin G acylase immobilized on Eupergit C gave (R)-(+)-α-amino-γ-butyrolactone and (S)-(-)-α-N- phenylacetamido-γ-butyrolactone in high enantiomeric purity (ee >99%) and 46-47% yields for each enantiomer. The enantiomers were converted into azasugars 1,4-dideoxyallonojirimycin and 1,4-dideoxymannojirimycin using Wittig olefination, catalytic ring-closing metathesis (RCM), and stereoselective dihydroxylation with OsO4 in 29% overall yield over 11 high yielding steps. Enzyme inhibition studies showed that 1,4-dideoxyallonojirimycin is a better β-glucosidase inhibitor (IC50 32.4 μM toward β-glucosidase from almonds) and a better β-galactosidase inhibitor (IC50 5.9 mM for β-galactosidase from Aspergillus oryzae) than 1,4-dideoxymannojirimycin (IC50 2.86 mM and 12.5 mM for β-glucosidase and β-galactosidase, respectively).

Process route upstream and downstream products

Process route

(4S)-2,2-dimethyl-4-(2-hydroxyethyl)oxazolidine-3-carboxylic acid tert-butyl ester
147959-18-0

(4S)-2,2-dimethyl-4-(2-hydroxyethyl)oxazolidine-3-carboxylic acid tert-butyl ester

(4S)-2,2-dimethyl-3-(t-butoxycarbonyl)-4-(formylmethyl)-1,3-oxazolidine
147959-19-1

(4S)-2,2-dimethyl-3-(t-butoxycarbonyl)-4-(formylmethyl)-1,3-oxazolidine

Conditions
Conditions Yield
(4S)-2,2-dimethyl-4-(2-hydroxyethyl)oxazolidine-3-carboxylic acid tert-butyl ester; With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -60 ℃;
With triethylamine; In dichloromethane; at -60 - 20 ℃; for 1.5h;
100%
With 1,3-oxazolidine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In ethyl acetate; at 80 ℃; for 3.5h;
100%
With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -60 - 20 ℃; for 1.5h;
97%
(4S)-2,2-dimethyl-4-(2-hydroxyethyl)oxazolidine-3-carboxylic acid tert-butyl ester; With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -60 ℃; for 0.75h;
With triethylamine; In dichloromethane; at -60 - 20 ℃; for 1.5h;
97%
With pyridinium chlorochromate; In dichloromethane; at 20 ℃; for 0.666667h;
79%
With pyridinium chlorochromate; In dichloromethane; for 2.5h;
74%
With Dess-Martin periodane; In dichloromethane; for 0.3h; Ambient temperature;
(4S)-2,2-dimethyl-4-(2-hydroxyethyl)oxazolidine-3-carboxylic acid tert-butyl ester; With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -78 - -60 ℃; for 0.75h;
With triethylamine; In dichloromethane; at -78 - 20 ℃; for 1h;
(4S)-2,2-dimethyl-4-(2-hydroxyethyl)oxazolidine-3-carboxylic acid tert-butyl ester; With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -78 ℃; for 0.5h;
With triethylamine; In dichloromethane; at -78 - 20 ℃; for 0.5h;
(4S)-2,2-dimethyl-4-(2-hydroxyethyl)oxazolidine-3-carboxylic acid tert-butyl ester; With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -78 ℃; for 0.75h;
With triethylamine; In dichloromethane; at -78 - 20 ℃; for 1h;
With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 18 ℃; for 2.1h; Schlenk technique;
With sulfur trioxide pyridine complex; triethylamine; In dimethyl sulfoxide; at 20 ℃; for 1h;
6.06 g
oxalyl dichloride
79-37-8

oxalyl dichloride

(4S)-2,2-dimethyl-4-(2-hydroxyethyl)oxazolidine-3-carboxylic acid tert-butyl ester
147959-18-0

(4S)-2,2-dimethyl-4-(2-hydroxyethyl)oxazolidine-3-carboxylic acid tert-butyl ester

(4S)-2,2-dimethyl-3-(t-butoxycarbonyl)-4-(formylmethyl)-1,3-oxazolidine
147959-19-1

(4S)-2,2-dimethyl-3-(t-butoxycarbonyl)-4-(formylmethyl)-1,3-oxazolidine

Conditions
Conditions Yield
With dimethyl sulfoxide; triethylamine;
74%
(S)-2-(tert-butoxycarbonylamino)-1,4-butanediol
128427-10-1,156627-42-8

(S)-2-(tert-butoxycarbonylamino)-1,4-butanediol

(4S)-2,2-dimethyl-3-(t-butoxycarbonyl)-4-(formylmethyl)-1,3-oxazolidine
147959-19-1

(4S)-2,2-dimethyl-3-(t-butoxycarbonyl)-4-(formylmethyl)-1,3-oxazolidine

Conditions
Conditions Yield
2: Swern oxidation;
Multi-step reaction with 3 steps
1.1: p-toluenesulfonic acid monohydrate / CH2Cl2 / 2 h / 20 °C
1.2: 67 h / 20 °C
2.1: 14.64 g / silica gel / CH2Cl2; H2O / 72 h / 20 °C
3.1: 97 percent / DMSO; oxalyl chloride; Et3N / CH2Cl2 / 1.5 h / -60 - 20 °C
With oxalyl dichloride; silica gel; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In dichloromethane; water; 3.1: Swern oxidation;
Multi-step reaction with 2 steps
1: 42 percent / p-toluenesulfonic acid / CH2Cl2 / 16 h / Ambient temperature
2: 74 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h
With toluene-4-sulfonic acid; pyridinium chlorochromate; In dichloromethane;
Multi-step reaction with 2 steps
1.1: toluene-4-sulfonic acid / dichloromethane / 3 h / 20 °C
2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C
2.2: 0.5 h / -78 - 20 °C
With oxalyl dichloride; toluene-4-sulfonic acid; dimethyl sulfoxide; In dichloromethane; 2.1: Swern oxidation / 2.2: Swern oxidation;
Multi-step reaction with 2 steps
1.1: (R)-10-camphorsulfonic acid / dichloromethane / 3 h / Reflux
2.1: dimethyl sulfoxide; oxalyl dichloride / dichloromethane / 0.75 h / -78 °C
2.2: 1 h / -78 - 20 °C
With oxalyl dichloride; (R)-10-camphorsulfonic acid; dimethyl sulfoxide; In dichloromethane; 2.1: |Swern Oxidation / 2.2: |Swern Oxidation;
Multi-step reaction with 2 steps
1: toluene-4-sulfonic acid / dichloromethane / 2 h / 18 °C
2: triethylamine; oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2.1 h / -78 - 18 °C / Schlenk technique
With oxalyl dichloride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In dichloromethane;
(S)-N-tert-butoxycarbonyl-aspartic acid diethyl ester
128427-09-8

(S)-N-tert-butoxycarbonyl-aspartic acid diethyl ester

(4S)-2,2-dimethyl-3-(t-butoxycarbonyl)-4-(formylmethyl)-1,3-oxazolidine
147959-19-1

(4S)-2,2-dimethyl-3-(t-butoxycarbonyl)-4-(formylmethyl)-1,3-oxazolidine

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1.1: 97 percent / NaBH4 / ethanol / Heating
2.1: p-toluenesulfonic acid monohydrate / CH2Cl2 / 2 h / 20 °C
2.2: 67 h / 20 °C
3.1: 14.64 g / silica gel / CH2Cl2; H2O / 72 h / 20 °C
4.1: 97 percent / DMSO; oxalyl chloride; Et3N / CH2Cl2 / 1.5 h / -60 - 20 °C
With sodium tetrahydroborate; oxalyl dichloride; silica gel; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In ethanol; dichloromethane; water; 4.1: Swern oxidation;
Multi-step reaction with 3 steps
1: 97 percent / NaBH4 / ethanol / 4 h / Heating
2: 42 percent / p-toluenesulfonic acid / CH2Cl2 / 16 h / Ambient temperature
3: 74 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h
With sodium tetrahydroborate; toluene-4-sulfonic acid; pyridinium chlorochromate; In ethanol; dichloromethane;
(4S)-4-[2-(1-methoxy-1-methylethoxy)ethyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester
850996-87-1

(4S)-4-[2-(1-methoxy-1-methylethoxy)ethyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

(4S)-2,2-dimethyl-3-(t-butoxycarbonyl)-4-(formylmethyl)-1,3-oxazolidine
147959-19-1

(4S)-2,2-dimethyl-3-(t-butoxycarbonyl)-4-(formylmethyl)-1,3-oxazolidine

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 14.64 g / silica gel / CH2Cl2; H2O / 72 h / 20 °C
2: 97 percent / DMSO; oxalyl chloride; Et3N / CH2Cl2 / 1.5 h / -60 - 20 °C
With oxalyl dichloride; silica gel; dimethyl sulfoxide; triethylamine; In dichloromethane; water; 2: Swern oxidation;
di-<i>tert</i>-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

(4S)-2,2-dimethyl-3-(t-butoxycarbonyl)-4-(formylmethyl)-1,3-oxazolidine
147959-19-1

(4S)-2,2-dimethyl-3-(t-butoxycarbonyl)-4-(formylmethyl)-1,3-oxazolidine

Conditions
Conditions Yield
Multi-step reaction with 5 steps
1.1: 98 percent / Et3N / H2O; dioxane
2.1: 97 percent / NaBH4 / ethanol / Heating
3.1: p-toluenesulfonic acid monohydrate / CH2Cl2 / 2 h / 20 °C
3.2: 67 h / 20 °C
4.1: 14.64 g / silica gel / CH2Cl2; H2O / 72 h / 20 °C
5.1: 97 percent / DMSO; oxalyl chloride; Et3N / CH2Cl2 / 1.5 h / -60 - 20 °C
With sodium tetrahydroborate; oxalyl dichloride; silica gel; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In 1,4-dioxane; ethanol; dichloromethane; water; 5.1: Swern oxidation;
dimethyl N-tert-butoxycarbonyl-L-aspartate
130622-08-1,55747-84-7

dimethyl N-tert-butoxycarbonyl-L-aspartate

(4S)-2,2-dimethyl-3-(t-butoxycarbonyl)-4-(formylmethyl)-1,3-oxazolidine
147959-19-1

(4S)-2,2-dimethyl-3-(t-butoxycarbonyl)-4-(formylmethyl)-1,3-oxazolidine

Conditions
Conditions Yield
3: Swern oxidation;
Multi-step reaction with 3 steps
1.1: lithium aluminium tetrahydride / tetrahydrofuran / 13 h / 0 - 20 °C / Inert atmosphere
2.1: (R)-10-camphorsulfonic acid / dichloromethane / 3 h / Reflux
3.1: dimethyl sulfoxide; oxalyl dichloride / dichloromethane / 0.75 h / -78 °C
3.2: 1 h / -78 - 20 °C
With lithium aluminium tetrahydride; oxalyl dichloride; (R)-10-camphorsulfonic acid; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; 3.1: |Swern Oxidation / 3.2: |Swern Oxidation;
tert-butyl (4S)-2,2-dimethyl-4-vinyl-1,3-oxazolidine-3-carboxylate
133625-87-3

tert-butyl (4S)-2,2-dimethyl-4-vinyl-1,3-oxazolidine-3-carboxylate

(4S)-2,2-dimethyl-3-(t-butoxycarbonyl)-4-(formylmethyl)-1,3-oxazolidine
147959-19-1

(4S)-2,2-dimethyl-3-(t-butoxycarbonyl)-4-(formylmethyl)-1,3-oxazolidine

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 1.) 9-borabicyclo<3.3.1>nonane, 2.) aq. H2O2, NaOH / 1.) THF, RT, 12 h, 2.) THF, RT, 4 h
2: Des-Martin periodinane / CH2Cl2 / 0.3 h / Ambient temperature
With sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; dihydrogen peroxide; Dess-Martin periodane; In dichloromethane;
di-<i>tert</i>-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

(4S)-2,2-dimethyl-3-(t-butoxycarbonyl)-4-(formylmethyl)-1,3-oxazolidine
147959-19-1

(4S)-2,2-dimethyl-3-(t-butoxycarbonyl)-4-(formylmethyl)-1,3-oxazolidine

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1.1: sodium hydroxide / tetrahydrofuran / 0.5 h
2.1: toluene-4-sulfonic acid / dichloromethane / 3 h / 20 °C
3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C
3.2: 0.5 h / -78 - 20 °C
With oxalyl dichloride; toluene-4-sulfonic acid; dimethyl sulfoxide; sodium hydroxide; In tetrahydrofuran; dichloromethane; 3.1: Swern oxidation / 3.2: Swern oxidation;
(S)-2-t-butoxycarbonylaminosuccinic acid 4-methyl ester
59768-74-0,124184-67-4

(S)-2-t-butoxycarbonylaminosuccinic acid 4-methyl ester

(4S)-2,2-dimethyl-3-(t-butoxycarbonyl)-4-(formylmethyl)-1,3-oxazolidine
147959-19-1

(4S)-2,2-dimethyl-3-(t-butoxycarbonyl)-4-(formylmethyl)-1,3-oxazolidine

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1.1: 4-methyl-morpholine; chloroformic acid ethyl ester / tetrahydrofuran / 1 h
1.2: 0.5 h
2.1: boron trifluoride diethyl etherate / acetone / 4 h / 20 °C
3.1: diisobutylaluminium hydride / dichloromethane / 2 h / Cooling with ice
4.1: triethylamine; sulfur trioxide pyridine complex / dimethyl sulfoxide / 1 h / 20 °C
With 4-methyl-morpholine; boron trifluoride diethyl etherate; sulfur trioxide pyridine complex; chloroformic acid ethyl ester; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; acetone;

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