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Type HazMat fee for 500 gram (Estimated)
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Limited Quantity USD 15-60
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Inaccessible (Haz class 6.1), International USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic USD 100+
Accessible (Haz class 3, 4, 5 or 8), International USD 200+
Chemical Structure| 33543-55-4 Chemical Structure| 33543-55-4

Structure of 33543-55-4

Chemical Structure| 33543-55-4

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Product Details of [ 33543-55-4 ]

CAS No. :33543-55-4
Formula : C6H6N2O3
M.W : 154.12
SMILES Code : NOC1=CC=C([N+]([O-])=O)C=C1
MDL No. :MFCD12923172
InChI Key :OOHKBWPOLBTKMR-UHFFFAOYSA-N
Pubchem ID :15562106

Safety of [ 33543-55-4 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H228-H301+H311+H331-H315-H319
Precautionary Statements:P240-P210-P241-P280-P370+P378-P501-P261-P270-P271-P264-P337+P313-P305+P351+P338-P361+P364-P332+P313-P301+P310+P330-P302+P352+P312-P304+P340+P311-P403+P233-P405
Class:4.1(6.1)
UN#:2926
Packing Group:

Application In Synthesis of [ 33543-55-4 ]

* 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.

  • Upstream synthesis route of [ 33543-55-4 ]

[ 33543-55-4 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 83077-00-3 ]
  • [ 33543-55-4 ]
YieldReaction ConditionsOperation in experiment
99.9%
Stage #1: at 25 - 32℃; for 1 h;
Stage #2: With sodium hydroxide In water at 33℃;
240 g Water-moist Ethyl-N-(4-nitrophenoxy)acetimidate, containing 181 g, 0.807 mol of product (when dry) was added to 397g 37 percent hydrochloric acid (5eq) in portions over 50 minutes, keeping the temperature at 25-32°C. Analysis (HPLC) after 60 minutes showed a conversion of 99.9percent. The slurry was diluted with 37 ml water and then neutralised with 58Og 33percent NaOH keeping the temperature below 330C. The slurry was then cooled to 240C, filtered, and the filter cake washed with 210 ml water. Drying afforded 124.5g 0-4-nitrophenyl hydroxylamine. Assay (NMR) 99.8 percent, chromatographic purity (HPLC) 99.4 area percent. Yield 99.9 percent
99.9%
Stage #1: at 25 - 32℃; for 1.83333 h;
Stage #2: With sodium hydroxide In water at 33℃;
240 g Water-moist Ethyl-N-(4-nitrophenoxy) acetimidate, containing 181 g, 0.807 mol of product (when dry) was added to 397g 37 percent hydrochloric acid (5eq) in portions over 50 minutes, keeping the temperature at 25-320C. Analysis (HPLC) after 60 minutes showed a conversion of 99.9percent. The slurry was diluted with 37 ml water and then neutralised with 58Og 33percent NaOH keeping the temperature below 33°C. The slurry was then cooled to 240C, filtered, and the filter cake washed with 210 ml water. Drying afforded 124.5g 0-4-nitrophenyl hydroxylamine. Assay (NMR) 99.8 percent, chromatographic purity (HPLC) 99.4 areapercent. Yield 99.9 percent
94%
Stage #1: With hydrogenchloride; water In acetonitrile at 25 - 30℃; for 2 h;
Stage #2: With sodium hydroxide In water; acetonitrile
Wet ethyl N-(4-nitrophenoxy)acetimidate, 781g (dry weight) is dissolved in 210Og acetonitrile and the temperature adjusted to ca 25CC. 515g 37 percent hydrochloric acid is added at such rate as to keep the temperature below 3O0C. The mixture is stirred at 25-3O0C until the reaction is complete, ca 2h. Then 209Og of 12 percent NaOH(aq) is added at 25-3O0C and the mixture stirred for ca 30 minutes. Vacuum is applied and ca 85 percent of the acetonitrile stripped at 100 mbar and a jacket temperature of 5O0C (inner temperature 25-3O0C). Water, 209Og, is added and the slurry stirred for 60 minutes. The product is filtered and washed with 505g water followed by drying under vacuum at 40°C. O-(4-Nitrophenyl)hydroxylamine, 56Og, is obtained. Yield 94 percent.
References: [1] Patent: WO2010/38029, 2010, A1, . Location in patent: Page/Page column 45.
[2] Patent: WO2010/116140, 2010, A1, . Location in patent: Page/Page column 47.
[3] Patent: WO2009/44143, 2009, A2, . Location in patent: Page/Page column 38.
[4] Journal of Organic Chemistry, 1984, vol. 49, p. 1348 - 1352.
[5] Journal of the American Chemical Society, 1982, vol. 104, # 23, p. 6393 - 6397.
[6] Patent: US2013/165674, 2013, A1, .
[7] Angewandte Chemie - International Edition, 2015, vol. 54, # 47, p. 14017 - 14021[8] Angew. Chem., 2015, vol. 127, # 47, p. 14223 - 14227,5.
  • 2
  • [ 350-46-9 ]
  • [ 33543-55-4 ]
References: [1] Organic Letters, 2019, vol. 21, # 1, p. 283 - 286.
[2] Journal of Physical Organic Chemistry, 1999, vol. 12, # 5, p. 357 - 363.
[3] Journal of the American Chemical Society, 1982, vol. 104, # 23, p. 6393 - 6397.
[4] Tetrahedron, 1972, vol. 28, p. 3833 - 3843.
[5] Organic Letters, 2013, vol. 15, # 13, p. 3366 - 3369.
[6] Organic Process Research and Development, 2002, vol. 6, # 3, p. 230 - 233.
[7] Angewandte Chemie - International Edition, 2015, vol. 54, # 47, p. 14017 - 14021[8] Angew. Chem., 2015, vol. 127, # 47, p. 14223 - 14227,5.
  • 3
  • [ 100-02-7 ]
  • [ 344266-15-5 ]
  • [ 33543-55-4 ]
  • [ 959-22-8 ]
References: [1] Journal of the American Chemical Society, 1981, vol. 103, # 15, p. 4558 - 4565.
  • 4
  • [ 100-02-7 ]
  • [ 33543-55-4 ]
References: [1] Organic and Biomolecular Chemistry, 2004, vol. 2, # 10, p. 1471 - 1475.
[2] Advanced Synthesis and Catalysis, 2017, vol. 359, # 10, p. 1643 - 1648.
  • 5
  • [ 344266-15-5 ]
  • [ 33543-55-4 ]
  • [ 959-22-8 ]
References: [1] Journal of the American Chemical Society, 1981, vol. 103, # 15, p. 4558 - 4565.
  • 6
  • [ 41828-26-6 ]
  • [ 33543-55-4 ]
References: [1] Journal of the American Chemical Society, 1981, vol. 103, # 15, p. 4558 - 4565.
  • 7
  • [ 100-47-0 ]
  • [ 33543-55-4 ]
  • [ 959-22-8 ]
  • [ 891-43-0 ]
  • [ 55-21-0 ]
References: [1] Journal of the American Chemical Society, 1981, vol. 103, # 15, p. 4558 - 4565.
  • 8
  • [ 100-00-5 ]
  • [ 33543-55-4 ]
References: [1] Journal of Organic Chemistry, 1984, vol. 49, p. 1348 - 1352.
[2] Patent: US2013/165674, 2013, A1, .
  • 9
  • [ 33543-54-3 ]
  • [ 33543-55-4 ]
References: [1] Tetrahedron, 1972, vol. 28, p. 3833 - 3843.
[2] Organic Process Research and Development, 2002, vol. 6, # 3, p. 230 - 233.
  • 10
  • [ 100-47-0 ]
  • [ 100-02-7 ]
  • [ 33543-55-4 ]
  • [ 959-22-8 ]
  • [ 891-43-0 ]
References: [1] Journal of the American Chemical Society, 1981, vol. 103, # 15, p. 4558 - 4565.
  • 11
  • [ 83077-00-3 ]
  • [ 100-02-7 ]
  • [ 33543-55-4 ]
References: [1] Journal of Organic Chemistry, 2012, vol. 77, # 23, p. 10835 - 10845.
  • 12
  • [ 118-83-2 ]
  • [ 33543-55-4 ]
References: [1] Journal of Organic Chemistry, 2012, vol. 77, # 23, p. 10835 - 10845.
  • 13
  • [ 100-00-5 ]
  • [ 100-02-7 ]
  • [ 33543-55-4 ]
References: [1] Journal of Organic Chemistry, 2012, vol. 77, # 23, p. 10835 - 10845.
 

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