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Chemical Structure| 5394-50-3 Chemical Structure| 5394-50-3

Structure of Dibenzyl hydrazodicarboxylate
CAS No.: 5394-50-3

Chemical Structure| 5394-50-3

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Synonyms: Dibenzyl hydrazine-1,2-dicarboxylate

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Product Details of [ 5394-50-3 ]

CAS No. :5394-50-3
Formula : C16H16N2O4
M.W : 300.31
SMILES Code : O=C(NNC(OCC1=CC=CC=C1)=O)OCC2=CC=CC=C2
Synonyms :
Dibenzyl hydrazine-1,2-dicarboxylate
MDL No. :MFCD00022028

Safety of [ 5394-50-3 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H318-H400
Precautionary Statements:P280-P305+P351+P338+P310
Class:9
UN#:3077
Packing Group:

Application In Synthesis of [ 5394-50-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 5394-50-3 ]

[ 5394-50-3 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 50995-48-7 ]
  • [ 5394-50-3 ]
  • methyl 1,2-dibenzyloxycarbonyl-hexahydro-pyridazine-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate;tetrabutylammomium bromide; In acetone; for 24h;Heating / reflux; 1 kg (3.3 mol) of 1,2-dibenzyloxycarbonyl-hydrazine, 0.025 kg of tetrabutylammonium bromide, 1 kg (2.2 eq) of potassium carbonate (K2CO3) as a fine powder and 5 l of acetone are placed in an equipped 8-liter reactor and the mixture is stirred. 1 kg (3.65 mol) of <strong>[50995-48-7]methyl 2,5-dibromovalerate</strong> are then added and the mixture is heated at the reflux temperature of the acetone for 24 hours. The mixture is cooled to 0 C. The solids are separated out by suction-filtration. The liquid medium is then concentrated under reduced pressure until an oily concentrate is obtained. 1 l of water is then added, followed by addition of 1.66 l of 30percent sodium hydroxide solution, while keeping the temperature at 40 C., and the reaction mixture is stirred for 5 to 7 hours at this temperature. 2.6 l of toluene are added, followed by slow addition of 1.4 l of 36percent hydrochloric acid to obtain a pH of about 1. The 1-benzyloxycarbonylhexahydropyridazin-3-yl-carboxylic acid of formula (I) crystallizes. It is filtered off by suction, washed with toluene and then with water, and dried. 0.62 kg of dry acid (overall yield 71percent) with a purity, determined by HPLC, of greater than 97.0percent is thus collected.
35 - ~ 85%Chromat. With potassium carbonate;methyl tributylammonium chloride; In water; toluene; at 80℃;Product distribution / selectivity; 168 g hydrazine hydrate (containing 24 percent by weight of hydrazine) and 300 g deionized water were charged to a 2 1 flask. 100 g aqueous sodium hydroxide (containing 32 percent by weight of sodium hydroxide) and 300 g benzyl chloroformate were added with vigorous stirring. The precipitate was filtered off and dried. Subsequently, the obtained solid was suspended in 650 g toluene. 267 g potassium carbonate and a catalytic amount of METHYL-TRI-N-BUTYLAMMONIUM chloride were added. Afterwards, 12 g water were added. The mixture was warmed up to 80 °C and subsequently 254 g <strong>[50995-48-7]methyl 2,5-dibromovalerate</strong> were added according to Reference Example 1, followed by determining the yield of the product by HPLC. It resulted in - 85percent. The solution in toluene was used for the manufacture of 1-BENZYLOXYCARBONYL-HEXAHYDRO- pyridazine-3-carboxylic acid as described in Example 3.; The reaction was carried out according to Example 1 with the difference that 35 g water were added corresponding to a concentration of approximately 5 percent concerning the mixture of solvent and water. A yield of merely 35 percent by area was determined by means of HPLC.
30%Chromat. With potassium carbonate;methyl tributylammonium chloride; In toluene; at 80℃;Product distribution / selectivity; The reaction was carried out according to Example 1 with the difference that the solvent was water-free. The yield of product was determined by means of high-pressure liquid chromatography. A yield of merely 30 percent by area was determined.
 

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