630-580-1088 sales@ambeed.com
Structure Search

List Search MOL Search Structure Search

0
Chemistry
Asymmetric Synthesis >>Chiral Building BlocksChiral Catalysts, Chiral Ligands and Chiral ReagentsChiral Resolution ReagentsBoronic acids/esters >>Aliphatic BoronsAromatic BoronsOther BoronsOxaborolesCatalysis Chemistry >>Achiral Crown LigandsC-H ActivationCarbon-Donor LigandsChiral Carbon LigandsChiral Crown LigandsChiral Olefin LigandsCross-CouplingCross-Coupling Using Transition Metal CatalystsDACH or Trost LigandsChemical Biology >>Conjugation Chemistry
GlycoscienceLinkers and CrosslinkersNucleic Acid ChemistryPEGylationPeptide ChemistryPhotolabile Protecting GroupHeterocyclic Building Blocks >>AcridinesAliphatic HeterocyclesAromatic HeterocyclesAzetidinesBenzimidazolesBenzisoxazolesBenzodioxansBenzofuransBenzothiazolesInorganic reagents >>Inorganic ReagentOrganic Building Blocks >>Acid AnhydridesAcyl Chlorides
AlcoholsAldehydesAliphatic Chain HydrocarbonsAliphatic Cyclic HydrocarbonsAlkenesAlkylsAlkynesOrganometallic Reagents >>Grignard ReagentsOrganoarsenicOrganobismuthOrganoboronOrganogermaniumOrganolithiumOrganomercuryOrganosiliconOrganotinSpecialty Synthesis >>Enzyme-Mediated SynthesisFluorous SynthesisIonic Liquids
Solid Supported SynthesisStains and Dyes >>Acid DyesAzoic DyesBasic DyesDirect DyesDisperse DyesDye IntermediatesMordant DyesOil DyesOther Stains and DyesSynthetic Reagents >>Acids and BasesC-C Bond FormationC-X Bond Formation (Halogen)C-X Bond Formation (Non-Halogen)Chelation and Complexation CompoundsCondensation AgentsCouplingDehydrating ReagentsFluorination Reagent
Pharmaceutical Intermediates
Analgesics >>BenzhydrocodoneBicifadineCapsaicinCelecoxibDebio-0827DexamethasoneElagolix SodiumEsketamine HydrochlorideIbuprofen SodiumAnesthetics >>CiprofolEsketamine HydrochlorideFospropofol Fospropofol DisodiumLevobupivacaine RemimazolamRemimazolam BesilateRemimazolam BesylateRopivacaineAnti-Addiction Agents >>Kakonein
Lofexidine HydrochlorideVarenicline Anti-inflammatory Agents >>ApremilastAsunaprevirATB-346 RelatedBalsalazide BaricitinibBencycloquidium BromideBudesonideCefiderocol Sulfate TosylateCeftaroline Fosamil AcetateAntibacterials >>AFN-1252 RelatedAlatrofloxacin Bedaquiline FumarateBesifloxacin BrilacidinCaspofungin AcetateCefiderocol Sulfate TosylateCefilavancinCeftaroline Fosamil
Anticonvulsants >>BrivaracetamCannabidiolEscitalopram OxalateEslicarbazepine Acetate RelatedFosphenytoinGabapentin EnacarbilJNJ-10234094LacosamideLevetiracetam RelatedAntidementia Agents >>Azeliragon RelatedDavunetideDonepezil HydrochlorideDonepezil RelatedEnsaculinFlorbetaben Flortaucipir F 18Flutemetamol IdalopirdineAntidepressants >>4-Chlorokynurenine
AgomelatineAgomelatine RelatedAllopregnanolone RelatedAmibegronAmitifadineAripiprazole RelatedBasimglurantBefloxatoneAntiemetics >>AprepitantAprepitant RelatedDolasetron RelatedDolasetron Mesylate HydrateFosaprepitant DimeglumineFosaprepitant RelatedOlanzapinePalonosetron RelatedPalonosetron HydrochlorideAntifungals >>Anidulafungin RelatedCabotegravirMore >>
Inhibitors/Agonists
ADC >>ADC AntibodyADC LinkerADC Linker with PayloadADC ToxinAntibody-Drug Conjugates (ADCs)Drug-Linker Conjugates for ADCAngiogenesis >>ALKBcr-AblBTKEGFRFAKFGFRFLT3HER2HIFAnti-infection >>3CLproAntibacterialAntibioticAntifungal
AntiparasiticAntiprotozoalAntiviralArenavirusBVDVApoptosis >>Apoptosis InducerBcl-2Bcl-6BRKc-Mycc-RETC/EBPCARDCaspaseAutophagy >>Atg4ATG4BATTECsAUTACsAutophagyBeclin1
FKBPLC3LRRK2Biochemical Reagent >>Cell Cycle >>AntifolateAPCAurora KinaseBUBCasein KinaseCdc25CDKChkCRISPR/Cas9Cytoskeleton >>ActinArp2/3 ComplexCYTHCytoplasmic DyneinDynaminFAKMore >>
Material Science
Aggregation-Induced Emission >>Other AIE BlocksTetraphenylethylene SeriesCOFs Linkers >>Aldehyde COFs LinkersAlkynyl COFs LinkersAmine COFs LinkersBoric COFs LinkersCyano COFs LinkersMultifunctional COFs linkersOther COFs linkersTriptycene SeriesElectronic Materials >>Battery MaterialsDye-Sensitized Solar Cell (DSSC) MaterialsElectronic MaterialLiquid Crystal (LC) MaterialsMolecular ConductorsOrganic Light-Emitting Diode (OLED) MaterialsOrganic Solar Cell (OPV) MaterialsOrganic Transistor (OFET) MaterialsPerovskite Solar Cell (PSC) MaterialsMagnetic Materials >>Magnetic Ionic LiquidsMagnetic MaterialMagnetic Metal Complexes
Organic Radicals Material Chemical Compounds >>Ligands for Functional Metal ComplexesLiquid Crystal (LC) Building BlocksPhthalocyanine Building BlocksPolymer and Macromolecule Semiconductor Building BlocksSmall Molecule Semiconductor Building BlocksSolubility Enhancing Reagents Supramolecular Host Materials MOF Ligands >>Carboxylic Acid MOF LigandsCarboxylic Acid Nitrogen-Containing Mixed MOF LigandsNitrogen-Containing MOF LigandsOther MOF LigandsNanomaterials >>Carbon NanomaterialsCeramic MembranesDendrimersGold NanoparticlesIron Oxide NanoparticlesMaterials by ApplicationMesoporous MaterialsMetals and Metal AlloysNano Minerals: NanoclaysOLED Materials >>Dopant
HostHTMOLED IntermediatesOther OLED related materialsOptical Materials >>Coumarin DyesCyanine and Squarylium DyesDCM DyesDipyrromethene DyesFluorescence MaterialsFluorescent ProbesHeat and Pressure Sensitive DyesNear-Infrared (NIR) DyesOrganic Non-Linear Optical (NLO) MaterialsOrganic Pigments >>Organic PigmentOther Materials >>Mateial OtherPolymer Science >>MonomersPolymer AdditivesPolymerization ReagentsPolymersResins
Contact Us
Home Cart 0 Sign in  
Chemistry
Organic Building Blocks
Aryls
dimethylamino
4-(Dimethylamino)benzohydrazide
Chemistry
Organic Building Blocks
Aryls
Amines Amides Hydrazines Hydrazides Benzene Compounds
dimethylamino
benzohydrazide

[ CAS No. 19353-92-5 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
HazMat Fee +

There will be a HazMat fee per item when shipping a dangerous goods. The HazMat fee will be charged to your UPS/DHL/FedEx collect account or added to the invoice unless the package is shipped via Ground service. Ship by air in Excepted Quantity (each bottle), which is up to 1g/1mL for class 6.1 packing group I or II, and up to 25g/25ml for all other HazMat items.

Type HazMat fee for 500 gram (Estimated)
Excepted Quantity USD 0.00
Limited Quantity USD 15-60
Inaccessible (Haz class 6.1), Domestic USD 80+
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| 19353-92-5
Chemical Structure| 19353-92-5
Structure of 19353-92-5 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 110K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 19353-92-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 19353-92-5 ]

SDS Specification
Alternatived Products of [ 19353-92-5 ]

Product Details of [ 19353-92-5 ]

CAS No. :19353-92-5 MDL No. :MFCD00014761
Formula : C9H13N3O Boiling Point : -
Linear Structure Formula :- InChI Key :HITIGLAGJBMISF-UHFFFAOYSA-N
M.W : 179.22 Pubchem ID :88019
Synonyms :

Calculated chemistry of [ 19353-92-5 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 51.55
TPSA : 58.36 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.36 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.51
Log Po/w (XLOGP3) : 0.05
Log Po/w (WLOGP) : 0.36
Log Po/w (MLOGP) : 1.19
Log Po/w (SILICOS-IT) : -0.22
Consensus Log Po/w : 0.58

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.13
Solubility : 13.4 mg/ml ; 0.0748 mol/l
Class : Very soluble
Log S (Ali) : -0.83
Solubility : 26.6 mg/ml ; 0.148 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.15
Solubility : 1.27 mg/ml ; 0.00711 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.12

Safety of [ 19353-92-5 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P280 UN#:2811
Hazard Statements:H302-H317-H350 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 19353-92-5 ]

* 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 [ 19353-92-5 ]

[ 19353-92-5 ] Synthesis Path-Downstream   1~14

  • 1
  • [ 1202-25-1 ]
  • [ 19353-92-5 ]
Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 655 - 670
[2]Chemistry Letters,1996,p. 47 - 48
[3]Journal of the American Chemical Society,2015,vol. 137,p. 14982 - 14991
[4]Chemistry of Heterocyclic Compounds,2019,vol. 55,p. 834 - 838
    Khim. Geterotsikl. Soedin.,2019,vol. 55,p. 834 - 838,5
[5]Bollettino Chimico Farmaceutico,1997,vol. 136,p. 244 - 249
[6]Chemische Berichte,1917,vol. 50,p. 1044
[7]Bioorganic and medicinal chemistry,2002,vol. 10,p. 557 - 560
[8]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 2909 - 2914
[9]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 6724 - 6731
[10]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 3028 - 3036
[11]Magnetic Resonance in Chemistry,2011,vol. 49,p. 648 - 654
[12]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 3615 - 3621
[13]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 1971 - 1985
[14]Dyes and Pigments,2020,vol. 175
  • 2
  • [ 19353-92-5 ]
  • [ 92-55-7 ]
  • 4-dimethylamino-N’-((5-nitrofuran-2-yl)methylene)benzohydrazide [ No CAS ]
Reference： [1]Bollettino Chimico Farmaceutico,1997,vol. 136,p. 244 - 249
  • 3
  • [ 619-84-1 ]
  • [ 19353-92-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: EDCI; 4-(N,N-dimethylamino)pyridine / tetrahydrofuran; dimethylformamide / 17 h / 20 °C 2: trifluoroacetic acid / CH2Cl2 / 2 h / 0 °C
Multi-step reaction with 2 steps 1: H2SO4 / Heating 2: hydrazine / H2O / Heating
Multi-step reaction with 2 steps 1: 96 percent / H2SO4 2: 56 percent / 35percent aq. hydrazine / Ambient temperature
Multi-step reaction with 2 steps 1: sulfuric acid / Reflux 2: hydrazine hydrate monohydrate / ethanol / Reflux
Multi-step reaction with 2 steps 1: sulfuric acid 2: hydrazine hydrate monohydrate / ethanol / Reflux
Multi-step reaction with 2 steps 1: sulfuric acid / 3 h / 70 °C 2: H4N2*5H2O / ethanol / 6 h / 70 °C
Multi-step reaction with 2 steps 1: sulfuric acid / Reflux 2: hydrazine hydrate monohydrate / ethanol / 70 °C
Multi-step reaction with 2 steps 1: sulfuric acid / 5 h / Reflux 2: hydrazine / methanol / 24 h / Reflux
Multi-step reaction with 2 steps 1: sulfuric acid / 2 h / 78 °C 2: hydrazine hydrate monohydrate / ethanol / 6 h / 78 °C
Multi-step reaction with 2 steps 1: sulfuric acid / 5 h / Reflux 2: hydrazine / methanol / 24 h / Reflux
Stage #1: p-N,N-dimethylaminobenzoic acid With sulfuric acid In methanol at 20℃; for 4h; Reflux; Stage #2: With hydrazine hydrate monohydrate In methanol at 75℃; for 0.5h; 4.1.1. General procedure for the synthesis of hydrazides General procedure: each carboxylic acid (a) (0.02 mol) was refluxed for 4 h in 20.0 mL (0.49 mol) of anhydrous methanol and 0.5 mL (0.01 mol) of sulfuric acid. The reaction mixture was cooled down to room temperature and the hydrazine hydrate 80% (v/v) (10.0 mL, 0.13 mol) was added. The system was maintained by vigorously stirring for more 30 min in reflux. After this period, the mixture was maintained at low temperature to give (b), and was purified from ethyl acetate. The hydrazide intermediate of compounds 1 and 2 were commercially obtained (Sigma-Aldrich, purity of 97%) [47].
Multi-step reaction with 2 steps 1: sulfuric acid / 6 h / 0 - 80 °C 2: hydrazine hydrate monohydrate / ethanol / 6 h / 80 °C

Reference： [1]Szczepankiewicz; Chiou; Credo; Alder; Nukkala; Zielinski; Jarvis; Mollison; Frost; Bauch; Hui; Liu; Claiborne; Li; Rosenberg; Jae; Tasker; Gunawardana; Von Geldern; Gwaltney II; Wu-Wong; Gehrke [Journal of Medicinal Chemistry, 2001, vol. 44, # 25, p. 4416 - 4430]
[2]Rando, Daniela G; Sato, Dayse N; Siqueira, Leonardo; Malvezzi, Alberto; Leite, Clarice Q F; do Amaral, Antonia T; Ferreira, Elizabeth I; Tavares, Leoberto C [Bioorganic and medicinal chemistry, 2002, vol. 10, # 3, p. 557 - 560]
[3]Tavares; Penna; Amaral [Bollettino Chimico Farmaceutico, 1997, vol. 136, # 3, p. 244 - 249]
[4]Zhang, Li-Rong; Liu, Zhi-Jun; Zhang, Hui; Sun, Jian; Luo, Yin; Zhao, Ting-Ting; Gong, Hai-Bin; Zhu, Hai-Liang [Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 11, p. 3615 - 3621]
[5]Du, Qian-Ru; Li, Dong-Dong; Pi, Ya-Zhou; Li, Jing-Ran; Sun, Jian; Fang, Fei; Zhong, Wei-Qing; Gong, Hai-Bin; Zhu, Hai-Liang [Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 8, p. 2286 - 2297]
[6]Kamal, Ahmed; Srikanth; Vishnuvardhan; Kumar, G. Bharath; Suresh Babu, Korrapati; Hussaini, S.M. Ali; Kapure, Jeevak Sopanrao; Alarifi, Abdullah [Bioorganic Chemistry, 2016, vol. 65, p. 126 - 136]
[7]Meira, Cássio S.; dos Santos Filho, José Maurício; Sousa, Caroline C.; Anjos, Pâmela S.; Cerqueira, Jéssica V.; Dias Neto, Humberto A.; da Silveira, Rafael G.; Russo, Helena M.; Wolfender, Jean-Luc; Queiroz, Emerson F.; Moreira, Diogo R.M.; Soares, Milena B.P. [Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 8, p. 1971 - 1985]
[8]Wang, Zhi-Gang; Ding, Xiao-Jing; Huang, Yu-Ying; Yan, Xiao-Jing; Ding, Bin; Li, Qing-Zhong; Xie, Cheng-Zhi; Xu, Jing-Yuan [Dyes and Pigments, 2020, vol. 175]
[9]Liu, Jie; Zhang, Guang-Yu; Zhang, Zhe; Li, Bo; Chai, Fei; Wang, Qi; Zhou, Zi-Dan; Xu, Ling-Ling; Wang, Shou-Kai; Jin, Zhen; Tang, You-Zhi [Bioorganic Chemistry, 2021, vol. 112]
[10]Yan, Xiao-Jing; Li, Zhe; Liu, Hai-Bo; Wang, Zhi-Gang; Fan, Jing; Xie, Cheng-Zhi; Li, Qing-Zhong; Xu, Jing-Yuan [Journal of Photochemistry and Photobiology A: Chemistry, 2022, vol. 422]
[11]De Azevedo, Ricardo Alexandre; Ferreira, Adilson Kleber; Jorge, Salomo Dria; Palace-Berl, Fanny; Pasqualoto, Kerly Fernanda Mesquita; Silva, Marcelo Nunes; Tavares, Leoberto Costa; Teixeira, Sarah Fernandes; Zingales, Bianca; Zorzi, Rodrigo Rocha [European Journal of Medicinal Chemistry, 2015, vol. 96, p. 330 - 339]
[12]Babu, Bathini Nagendra; Kaki, Venkata Rao; Kiranmai, Gaddam; Makhal, Priyanka N.; Nagesh, Narayana; Parimala Devi, G.; Shaikh, Arbaz Sujat; Shankaraiah, Nagula; Sigalapalli, Dilep Kumar; Tangellamudi, Neelima D.; Tokala, Ramya [Bioorganic and Medicinal Chemistry Letters, 2022, vol. 65]
  • 4
  • [ 10287-53-3 ]
  • [ 19353-92-5 ]
YieldReaction ConditionsOperation in experiment
91% With hydrazine hydrate In ethanol for 12h; Reflux; Inert atmosphere; Schlenk technique; General Procedure for the synthesis of the compounds 2A. General procedure: Hydrazine monohydrate (5 mmol) was added dropwise to a solution of compounds 1A-C (1mmol) in EtOH. The mixture was refluxed for 12 h, and then the solvent was removed by rotary evaporation. The residue was treated with water and extracted with CH2Cl2. The organic layer was washed with water and dried over magnesium sulfate. The solvent was removed by rotary evaporation. The residue was purified by recrystallization.
75% With hydrazine In ethanol for 48h; Reflux;
With hydrazine hydrate In ethanol Reflux;
With hydrazine hydrate In ethanol Reflux;
With H4N2*5H2O In ethanol at 70℃; for 6h;
With hydrazine hydrate In ethanol at 90℃; Inert atmosphere; 1.b b. In product A, 80% hydrazine hydrate and 95% ethanol are added in a 1:20 molar ratio. The reaction is refluxed under a nitrogen atmosphere at 90 ° C. The reaction is completed and the column is purified (mobile phase dichloromethane: methanol = 20: 1) to give product B.
With hydrazine hydrate In ethanol for 16h; Reflux; 2.2. Synthesis of Compound 1 As shown in Scheme 1, the reflux of 4-dimethylamino-benzoic acidethyl ester (0.3584 g, 2 mmol) and hydrazine hydrate (85%,0.5 mL) in25 mL of ethanol solution were removed until the complete consumptionof imidazole-2-formaldehyde, which was monitored by TLC(about 16 h). 4-Dimethylamino-benzoic acid hydrazide (0.1791 g, 1.0mmol) and imidazole-2-formaldehyde (0.096 g, 1.0mmol)were solvedin 25 mL ethanol and kept refluxing until complete consumption of imidazole-2-formaldehyde, which was monitored by TLC (about 12 h).The reaction mixture was cooled to room temperature and a whiteprecipitate was obtained through recrystallization. The white precipitatewas collected by filtration and washed three times withmethanol to get purified precipitate, and the total yield was up to73%. Ultimately, a white solid of compound 1 was obtained by thevacuum dryer and was characterized by NMR, Elemental analysesand ESI mass data, which were consistent with the proposedformulation.Compound 1: 1H NMR (400 MHz, DMSO-d6): δ (ppm) 12.73 (s, 1H),8.30 (s, 1H), 7.78(d, J=12 Hz, 2H), 7.10(s, 1H), 6.96(d, J=8 Hz, 2H),6.73(d, J = 8 Hz, 2H), 2.98(s, 6H); 13C NMR (400 MHz, DMSO-d6) δ(ppm): 167.94, 152.59, 143.49, 132.93, 129.55, 123.84, 119.60, 111.30,39.91; ESI-MS m/z [M - H]+: calcd, 258.13 found, 258.14; ElementAnal.: calcd. for C13H15N5O: C, 60.69; H, 5.88; N, 27.22%, found: C,61.28; H, 5.62; N, 26.65%.
With hydrazine hydrate In ethanol; toluene at 70℃; for 16h;
With hydrazine hydrate In ethanol at 78℃; for 6h;

Reference： [1]Khelladi, Mustapha; Leclerc, Nicolas; Jacquemin, Denis; De Nicola, Antoinette; Ulrich, Gilles [Tetrahedron Letters, 2018, vol. 59, # 10, p. 878 - 881]
[2]Location in patent: experimental part Mu, Honglei; Gong, Rui; Ren, Lin; Zhong, Cheng; Sun, Yimin; Fu, Enqin [Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2008, vol. 70, # 4, p. 923 - 928]
[3]Location in patent: scheme or table Zheng, Qing-Zhong; Zhang, Xiao-Min; Xu, Ying; Cheng, Kui; Jiao, Qing-Cai; Zhu, Hai-Liang [Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 22, p. 7836 - 7841]
[4]Du, Qian-Ru; Li, Dong-Dong; Pi, Ya-Zhou; Li, Jing-Ran; Sun, Jian; Fang, Fei; Zhong, Wei-Qing; Gong, Hai-Bin; Zhu, Hai-Liang [Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 8, p. 2286 - 2297]
[5]Kamal, Ahmed; Srikanth; Vishnuvardhan; Kumar, G. Bharath; Suresh Babu, Korrapati; Hussaini, S.M. Ali; Kapure, Jeevak Sopanrao; Alarifi, Abdullah [Bioorganic Chemistry, 2016, vol. 65, p. 126 - 136]
[6]Current Patent Assignee: HUAZHONG UNIVERSITY OF SCIENCE & TECHNOLOGY - CN107501123, 2017, A Location in patent: Paragraph 0021
[7]Fang, Hao; Huang, Peng-Cheng; Wu, Fang-Ying [Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2018, vol. 204, p. 568 - 575]
[8]Mahy, William; Willis, Nicky J.; Zhao, Yuguang; Woodward, Hannah L.; Svensson, Fredrik; Sipthorp, James; Vecchia, Luca; Ruza, Reinis R.; Hillier, James; Kjær, Svend; Frew, Sarah; Monaghan, Amy; Bictash, Magda; Salinas, Patricia C.; Whiting, Paul; Vincent, Jean-Paul; Jones, E. Yvonne; Fish, Paul V. [Journal of Medicinal Chemistry, 2020, vol. 63, # 21, p. 12942 - 12956]
[9]Liu, Jie; Zhang, Guang-Yu; Zhang, Zhe; Li, Bo; Chai, Fei; Wang, Qi; Zhou, Zi-Dan; Xu, Ling-Ling; Wang, Shou-Kai; Jin, Zhen; Tang, You-Zhi [Bioorganic Chemistry, 2021, vol. 112]
  • 5
  • [ 19353-92-5 ]
  • [ 10406-06-1 ]
  • [ 1252802-29-1 ]
Reference： [1]European Journal of Medicinal Chemistry,2010,vol. 45,p. 4664 - 4668
  • 6
  • [ 2215-76-1 ]
  • [ 19353-92-5 ]
  • [ 1292823-32-5 ]
YieldReaction ConditionsOperation in experiment
With acetic acid In ethanol at 60℃; for 12h; 1 EXAMPLE 1(N',N"¾N',N'''£')-N',N'''-((Oxybis(4,1-phenylene))bis(methanylylidene))bis(4- (dimethylamino)benzohydrazide) (Compound 101)[0565] Compound 101 was prepared according to the procedure described in Scheme II. To a solution of 4,4' -oxybisbenzaldehyde (Aldrich, 42 mg, 0.186 mmol) and 4- dimethylaminobenzyhydrazide (Alfa Aesar, 73 mg, 0.408 mmol) in 3 mL of ethanol was added 3 drops of acetic acid. The reaction was heated to 60 °C for 12 h, cooled to room temperature and filtered. The white precipitate was washed with water (5 mL) followed by methanol (5 mL) and dried under vacuum to yield 55 mg of compound 101 as a white powder. [M+H]+ calcd for C32H33N6O3: 549.26; found: 549.05.
Reference： [1]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - WO2011/46954, 2011, A1 Location in patent: Page/Page column 125
  • 7
  • [ 19353-92-5 ]
  • [ 50868-68-3 ]
  • 2-[(E)-2-(5-bromothiophen-2-yl)ethenyl]-5-[4-(N,N-dimethylamino)phenyl]-1,3,4-oxadiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
43% With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In ethyl acetate at 160℃; Sealed tube; Inert atmosphere; Microwave irradiation; 15 General procedure for two steps synthesis of 1,3,4-oxadiazole derivatives 8-17 (Method A) and general procedure for one-step synthesis of 1,3,4-oxadiazole derivatives 8-28 (Method B) General procedure: Method B; To a stirred solution of acrylic acid (200mg, 1 eq) and substituted hydrazide (1 eq) in dry ethyl acetate (5-10mL) were added dropwise T3P (3 eq, 50% solution in EtOAc) and triethylamine (5 eq). The reaction vessel was sealed under argon atmosphere and the mixture was heated under microwave conditions at 160°C for 20min to 30min. The completion of reaction was confirmed by TLC. The mixture was cooled to room temperature. The organic layer was washed twice with 1N HCl, once with H2O and once with brine. The organic layer was dried under Na2SO4 and concentrated under reduced pressure. The crude product was purified by silica gel flash chromatography (cyclohexan/EtOAc or DCM/Methanol) to afford the desired 1,3,4-oxadiazole derivative.; 4.1.2.15 2-[(E)-2-(5-bromothiophen-2-yl)ethenyl]-5-[(4-N,N-dimethyl)phenyl]-1,3,4-oxadiazole 20 1H RMN (DMSO-d6, 400 MHz): δ = 7.81 (d, J = 8.9 Hz, 2H), 7.72 (d, J = 16.1 Hz, 1H), 7.34 (d, J = 3.8 Hz, 1H), 7.25 (d, J = 3.8 Hz, 1H), 6.94 (d, J = 16.2 Hz, 1H), 6.80 (d, J = 9.0 Hz, 2H), 2.98 (s, 6H); 13C NMR (DMSO-d6, 101 MHz): δ = 164.52, 162.95, 152.89, 142.14, 132.35, 131.40, 130.30, 128.46, 114.75, 112.28, 110.07, 109.86, 40.18; LC/MS (ESI): 375.77 [M+H]+ and isotopic peak: 377.77; purity = 96%; HRMS (TOF, ESI+) cald for C16H15N3OSBr (M + H)+ 376.0119, found 376.0119; orange powder. Yield = 43%.
Reference： [1]Benmansour, Fatiha; Eydoux, Cécilia; Querat, Gilles; De Lamballerie, Xavier; Canard, Bruno; Alvarez, Karine; Guillemot, Jean-Claude; Barral, Karine [European Journal of Medicinal Chemistry, 2016, vol. 109, p. 146 - 156]
  • 8
  • [ 19353-92-5 ]
  • [ 13395-36-3 ]
  • C19H27N3O4 [ No CAS ]
  • C19H27N3O4 [ No CAS ]
Reference： [1]Russian Journal of Coordination Chemistry,2017,vol. 43,p. 93 - 96
    Koord. Khim.,2017,vol. 43,p. 99 - 102,4
  • 9
  • [ 19353-92-5 ]
  • [ 10111-08-7 ]
  • C13H15N5O [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% In ethanol; for 12h; As shown in Scheme 1, the reflux of 4-dimethylamino-benzoic acidethyl ester (0.3584 g, 2 mmol) and hydrazine hydrate (85%,0.5 mL) in25 mL of ethanol solution were removed until the complete consumptionof imidazole-2-formaldehyde, which was monitored by TLC(about 16 h). 4-Dimethylamino-benzoic acid hydrazide (0.1791 g, 1.0mmol) and imidazole-2-formaldehyde (0.096 g, 1.0mmol)were solvedin 25 mL ethanol and kept refluxing until complete consumption of imidazole-2-formaldehyde, which was monitored by TLC (about 12 h).The reaction mixture was cooled to room temperature and a whiteprecipitate was obtained through recrystallization. The white precipitatewas collected by filtration and washed three times withmethanol to get purified precipitate, and the total yield was up to73%. Ultimately, a white solid of compound 1 was obtained by thevacuum dryer and was characterized by NMR, Elemental analysesand ESI mass data, which were consistent with the proposedformulation.Compound 1: 1H NMR (400 MHz, DMSO-d6): delta (ppm) 12.73 (s, 1H),8.30 (s, 1H), 7.78(d, J=12 Hz, 2H), 7.10(s, 1H), 6.96(d, J=8 Hz, 2H),6.73(d, J = 8 Hz, 2H), 2.98(s, 6H); 13C NMR (400 MHz, DMSO-d6) delta(ppm): 167.94, 152.59, 143.49, 132.93, 129.55, 123.84, 119.60, 111.30,39.91; ESI-MS m/z [M - H]+: calcd, 258.13 found, 258.14; ElementAnal.: calcd. for C13H15N5O: C, 60.69; H, 5.88; N, 27.22%, found: C,61.28; H, 5.62; N, 26.65%.
Reference： [1]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2018,vol. 204,p. 568 - 575
  • 10
  • [ 103854-64-4 ]
  • [ 19353-92-5 ]
  • C20H20N4O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol; at 80℃; for 3h; General procedure: 8-Methoxyquinoline-2-carbaldehyde (25, 0.534 mmol) was refluxedwith various substituted acylhydrazines (0.587 mmol, 1.1 eq) in ethanol(5-10 mL) to get acyl hydrazides of 8-hydroxyquinoline. After completionof reaction, quinoline acyl hydrazides were found as precipitateson cooling to -15 C. Precipitates were washed with coldethanol and dried under vacuum. These acyl hydrazides were used directlyfor one pot synthesis of 2,5-disubstituted-1,3,4-oxadiazole usingiodine/K2CO3 catalysed oxidative cyclization. To the acyl hydrazides(1.0 eq) in DMSO (5-10 mL), K2CO3 (3.0 eq) and iodine (1.2 eq) wereadded in sequence and refluxed at 110 C. After the completion, thereaction mixture was cooled and saturated solution of sodium thiosulfatewas added. The precipitates were collected and dried under highvacuum to get the respective compounds (33-50).
Reference： [1]Bioorganic Chemistry,2018,vol. 80,p. 591 - 601
  • 11
  • [ 7310-95-4 ]
  • [ 19353-92-5 ]
  • (N',N'''E,N',N'''E)-N',N'''-((2-hydroxy-5-methyl-1,3-phenylene)bis(methanylylidene))bis(4-(dimethylamino)benzohydrazide) [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With trifluoroacetic acid In dimethyl sulfoxide at 20 - 100℃; for 16h; General experimental procedure for the synthesis ofcompounds 3. General procedure: A mixture of the corresponding dialdehyde(1 eq.) and the corresponding hydrazide (2 eq.) were dissolvedin DMSO (up to a 0.1-0.01 M concentration) and a few dropsof trifluoroacetic acid were added. The reaction mixture washeated at 100°C for 4 hours and left at room temperatureovernight (12 h). To the reaction mixture water was added(90% v/v) and the resulting precipitate was filtered, washedwith water and dried to afford pure product.
81% With trifluoroacetic acid In dimethyl sulfoxide at 20 - 100℃; General experimental procedure for the synthesis ofcompounds 3 General procedure: A mixture of the corresponding dialdehyde(1 eq.) and the corresponding hydrazide (2 eq.) were dissolvedin DMSO (up to a 0.1-0.01 M concentration) and a few dropsof trifluoroacetic acid were added. The reaction mixture washeated at 100°C for 4 hours and left at room temperatureovernight (12 h). To the reaction mixture water was added(90% v/v) and the resulting precipitate was filtered, washedwith water and dried to afford pure product. (N',N'''E,N',N'''E)-N',N'''-((2-hydroxy-5-methyl-1,3-phenylene)bis(methanylylidene))bis(4-(dimethylamino)benzohydrazide) 3a. Yellow solid. Yield 81%(0.445 g). m.p.209-212 °C. Rf=0.29 (silica, DCM:MeOH=9:1).1HNMR (500.13 MHz, DMSO-d6): δ= 12.42 (s, 1H, -OH), 11.81(s, 2H, -NH), 8.67 (s, 2H, H5), 7.84 (d, 4H, 3J = 8.9 Hz,H7/H11), 7.50 (s, 2H, H3), 6.77 (s, 4H, 3J = 8.9 Hz, H8/H10),3.01 (s, 12H, -N(CH3)2), 2.31 (s, 3H, -CH3) ppm. 13C NMR(125.77 MHz, DMSO-d6): 162.7 (C=O), 154.4 (C-1), 152.6(C-9), 144.5 (C-5), 129.7 (C-3), 129.2 (C-7/C-11), 128.1 (C-4), 120.2 (C-2), 118.9 (C-6), 110.9 (C8/C10), 39.6 (-N(CH3)2overlapped with DMSO), 20.0 (-CH3) ppm. HRMS (APCI, +)m/z: calc. for C27H31N6O3 [M+H]+487.2458; found 487.2447
Reference： [1]Coman, Anca G.; Hadade, Niculina D.; Hanganu, Anamaria; Mǎdǎlan, Augustin M.; Matache, Mihaela; Paun, Anca; Popescu, Codruţa C. [Revue Roumaine de Chimie, 2020, vol. 65, # 1, p. 109 - 114]
[2]Coman, Anca G.; Paun, Anca; Popescu, Codruța C.; Hadade, Niculina D.; Hanganu, Anamaria; Mădălan, Augustin M.; Matache, Mihaela [Revue Roumaine de Chimie, 2021, vol. 65, # 1, p. 109 - 114]
  • 12
  • [ 769-26-6 ]
  • [ 19353-92-5 ]
  • 4-(dimethylamino)-N'-(1-mesitylethylidene)benzohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With C83H64AuF6N3O6S2; In chlorobenzene; at 60℃; for 42h;Schlenk technique; General procedure: In a small Schlenk flask equipped with a small stirring bar the corresponding alkyne (0.5 mmol) and the corresponding benzhydrazide (0.5 mmol) were mixed with anisole or chlorobenzene (2 mL). For the internal standard mesitylene (69 μL, 0.5 mmol) was added. A stock solution of the corresponding gold-triflimide catalyst (0.005 M in anisole or chlorobenzene, 200 μL, 0.001 mmol, 0.2 mol %) was introduced to the mixture. The reaction mixture was stirred at 60 C or 80 C for the respective time and the progress of the reaction was monitored by GC. After the reaction was completed, the solvent was removed in vacuo and the residue triturated in pentane. Column chromatography (DCM/ethyl acetate 5:1) afforded the respective benzohydrazone in good to excellent yields.
Reference： [1]Beilstein Journal of Organic Chemistry,2020,vol. 16,p. 2080 - 2086
  • 13
  • [ 19353-92-5 ]
  • [ 1895-39-2 ]
  • N,N-dimethyl-4-(1,3,4-oxadiazol-2-yl-d)aniline [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With potassium phosphate; water-d2 In acetonitrile at 100℃; for 1h; Sealed tube; Inert atmosphere; 2. General procedure for the synthesis of 3 General procedure: Anhydrous CH3CN (2 mL) was added to a mixture of ClCF2COONa 2a (0.3 mmol, 1.5 equiv) and hydrazides 1 (0.2 mmol, 1 equiv) in the presence of K3PO4 (0.3 mmol, 1.5 equiv) and D2O (4 mmol, 20equiv). Then the sealed tube was stirred at 100 °C under N2 for 1 h. Upon completion of the reaction, the solvent was evaporated under reduced pressure and the residue was purified by flash column chromatograph (silica gel, petroleum ether:EtOAc = 2:1, v/v) to give the desired product 4.
Reference： [1]Wang, Ya; Mu, Shiqiang; Li, Xin; Song, Qiuling [Chinese Chemical Letters, 2022, vol. 33, # 3, p. 1511 - 1514]
  • 14
  • [ 19353-92-5 ]
  • [ 1895-39-2 ]
  • [ 90839-97-7 ]
YieldReaction ConditionsOperation in experiment
93% With potassium phosphate In acetonitrile at 100℃; for 1h; Sealed tube; Inert atmosphere; 2. General procedure for the synthesis of 3 General procedure: CH3CN (2 mL) was added to a mixture of ClCF2COONa 2a (0.3 mmol, 1.5 equiv) and hydrazides 1 (0.2 mmol, 1 equiv) in the presence of K3PO4 (0.3 mmol, 1.5 equiv). Then the sealed tube was stirred at 100 °C under N2 for 1 h. Upon completion of the reaction, the solvent was evaporated under reduced pressure and the residue was purified by flash column chromatograph (silica gel, petroleum ether:EtOAc = 2:1, v/v) to give the desired product 3.
Reference： [1]Wang, Ya; Mu, Shiqiang; Li, Xin; Song, Qiuling [Chinese Chemical Letters, 2022, vol. 33, # 3, p. 1511 - 1514]

Tags: 19353-92-5 synthesis path| 19353-92-5 SDS| 19353-92-5 COA| 19353-92-5 purity| 19353-92-5 application| 19353-92-5 NMR| 19353-92-5 COA| 19353-92-5 structure

Same Skeleton Products
Related Products
Categories
Chemistry
Organic Building Blocks
Amines
dimethylamino
Chemistry
Organic Building Blocks
Hydrazides
benzohydrazide
Chemistry
Organic Building Blocks
Benzene Compounds
benzohydrazide
Chemistry
Organic Building Blocks
Aryls
Chemistry
Organic Building Blocks
Amides
Chemistry
Organic Building Blocks
Hydrazines
Historical Records