CN114230470A - Synthetic method and application of stable isotope labeled benzidine - Google Patents
Synthetic method and application of stable isotope labeled benzidine Download PDFInfo
- Publication number
- CN114230470A CN114230470A CN202111557533.6A CN202111557533A CN114230470A CN 114230470 A CN114230470 A CN 114230470A CN 202111557533 A CN202111557533 A CN 202111557533A CN 114230470 A CN114230470 A CN 114230470A
- Authority
- CN
- China
- Prior art keywords
- labeled
- stable isotope
- benzidine
- added
- synthetic method
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 title claims abstract description 37
- 238000010189 synthetic method Methods 0.000 title claims description 12
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims abstract description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 22
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000000203 mixture Substances 0.000 claims abstract description 19
- 238000006243 chemical reaction Methods 0.000 claims abstract description 17
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims abstract description 16
- 239000003054 catalyst Substances 0.000 claims abstract description 12
- 238000003756 stirring Methods 0.000 claims abstract description 10
- WDFQBORIUYODSI-UHFFFAOYSA-N 4-bromoaniline Chemical compound NC1=CC=C(Br)C=C1 WDFQBORIUYODSI-UHFFFAOYSA-N 0.000 claims abstract description 8
- 235000011056 potassium acetate Nutrition 0.000 claims abstract description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000003960 organic solvent Substances 0.000 claims abstract description 5
- 239000000376 reactant Substances 0.000 claims abstract description 5
- 238000001308 synthesis method Methods 0.000 claims abstract description 5
- 239000012299 nitrogen atmosphere Substances 0.000 claims abstract description 3
- GMQUEDBQYNHEEM-UHFFFAOYSA-N [B].[B].CC(C)(O)C(C)(C)O.CC(C)(O)C(C)(C)O Chemical compound [B].[B].CC(C)(O)C(C)(C)O.CC(C)(O)C(C)(C)O GMQUEDBQYNHEEM-UHFFFAOYSA-N 0.000 claims abstract 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 15
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 14
- 239000000284 extract Substances 0.000 claims description 10
- 239000012074 organic phase Substances 0.000 claims description 10
- 238000004440 column chromatography Methods 0.000 claims description 9
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical group N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 claims description 5
- 239000000706 filtrate Substances 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 4
- 238000012805 post-processing Methods 0.000 claims description 3
- 238000000746 purification Methods 0.000 claims description 3
- 238000012958 reprocessing Methods 0.000 claims description 3
- 239000005695 Ammonium acetate Substances 0.000 claims description 2
- 235000019257 ammonium acetate Nutrition 0.000 claims description 2
- 229940043376 ammonium acetate Drugs 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 21
- 230000002194 synthesizing effect Effects 0.000 abstract description 6
- 238000011161 development Methods 0.000 abstract description 3
- 238000002156 mixing Methods 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 29
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- WDFQBORIUYODSI-IDEBNGHGSA-N 4-bromoaniline Chemical compound N[13C]1=[13CH][13CH]=[13C](Br)[13CH]=[13CH]1 WDFQBORIUYODSI-IDEBNGHGSA-N 0.000 description 9
- HFACYLZERDEVSX-WCGVKTIYSA-N [13C]1(=[13CH][13CH]=[13C](N)[13CH]=[13CH]1)[13C]1=[13CH][13CH]=[13C](N)[13CH]=[13CH]1 Chemical compound [13C]1(=[13CH][13CH]=[13C](N)[13CH]=[13CH]1)[13C]1=[13CH][13CH]=[13C](N)[13CH]=[13CH]1 HFACYLZERDEVSX-WCGVKTIYSA-N 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 5
- 238000001514 detection method Methods 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
- 235000019441 ethanol Nutrition 0.000 description 5
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000011159 matrix material Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- HFACYLZERDEVSX-BJLRPUNDSA-N 4-(4-amino-2,3-dideuteriophenyl)-N,N,2,3,5,6-hexadeuterioaniline Chemical group C1(=C(C(=C(N([2H])[2H])C(=C1[2H])[2H])[2H])[2H])C=1C(=C(C(N)=CC=1)[2H])[2H] HFACYLZERDEVSX-BJLRPUNDSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000004750 isotope dilution mass spectroscopy Methods 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 2
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000012491 analyte Substances 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 230000000711 cancerogenic effect Effects 0.000 description 2
- 231100000315 carcinogenic Toxicity 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229910052805 deuterium Inorganic materials 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- 150000001989 diazonium salts Chemical class 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 206010005003 Bladder cancer Diseases 0.000 description 1
- 208000005623 Carcinogenesis Diseases 0.000 description 1
- 206010012442 Dermatitis contact Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 206010067125 Liver injury Diseases 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 description 1
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000036952 cancer formation Effects 0.000 description 1
- 231100000504 carcinogenesis Toxicity 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 208000010247 contact dermatitis Diseases 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 125000004431 deuterium atom Chemical group 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000001948 isotopic labelling Methods 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 201000002528 pancreatic cancer Diseases 0.000 description 1
- 208000008443 pancreatic carcinoma Diseases 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 201000005112 urinary bladder cancer Diseases 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
- C07C209/74—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton by halogenation, hydrohalogenation, dehalogenation, or dehydrohalogenation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
本发明公开了一种稳定同位素标记的联苯胺的合成方法及其应用,合成方法包括:将稳定同位素标记的苯胺与N‑溴代丁二酰亚胺置于有机溶剂中混合,加入催化剂后在室温下搅拌反应,反应后对混合物进行后处理得到4‑溴苯胺‑13C6H4;在氮气气氛保护下,将得到的4‑溴苯胺‑13C6H4加入到含有钯/碳催化剂、乙酸钾和双(频哪醇合)二硼的乙醇溶液中,加热搅拌,反应后冷却至室温,并对得到的反应物进行再处理,即得稳定同位素标记的联苯胺。本发明所提供的方法步骤简单且工艺可控,具有效率高和产率高的优势;本发明所制备得到的稳定同位素标记的4,4'‑联苯胺‑13C12H8的质量稳定,具有极大的开发利用价值。The invention discloses a method for synthesizing stable isotope-labeled benzidine and application thereof. The synthesis method comprises: placing stable isotope-labeled aniline and N-bromosuccinimide in an organic solvent and mixing, adding a catalyst and adding The reaction was stirred at room temperature, and after the reaction, the mixture was post-treated to obtain 4 -bromoaniline - 13C6H4 ; under nitrogen atmosphere protection, the obtained 4 -bromoaniline - 13C6H4 was added to a catalyst containing palladium/carbon , potassium acetate and bis(pinacol) diboron in ethanol solution, heat and stir, cool to room temperature after the reaction, and reprocess the obtained reactant to obtain stable isotope-labeled benzidine. The method provided by the invention has simple steps and controllable process, and has the advantages of high efficiency and high yield; the stable isotope-labeled 4,4'-benzidine- 13 C 12 H 8 prepared by the invention has stable quality, It has great development and utilization value.
Description
Claims (9)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202111557533.6A CN114230470A (en) | 2021-12-19 | 2021-12-19 | Synthetic method and application of stable isotope labeled benzidine |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202111557533.6A CN114230470A (en) | 2021-12-19 | 2021-12-19 | Synthetic method and application of stable isotope labeled benzidine |
Publications (1)
Publication Number | Publication Date |
---|---|
CN114230470A true CN114230470A (en) | 2022-03-25 |
Family
ID=80758685
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202111557533.6A Pending CN114230470A (en) | 2021-12-19 | 2021-12-19 | Synthetic method and application of stable isotope labeled benzidine |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN114230470A (en) |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1490302A (en) * | 2002-10-15 | 2004-04-21 | 协和化学株式会社 | Benzidine compound preparing method |
CN1506349A (en) * | 2002-12-11 | 2004-06-23 | 中国石油化工股份有限公司 | Prepn process of 4-amino diphenylamine |
KR20160106238A (en) * | 2015-03-02 | 2016-09-12 | (주)부흥산업사 | Novel aromatic amine derivatives for organic electroluminescent device |
CN106995461A (en) * | 2017-03-03 | 2017-08-01 | 中山大学 | A kind of Phosphine ligands of the structure containing benzofuran and its preparation method and application |
CN109467561A (en) * | 2018-11-19 | 2019-03-15 | 广东工业大学 | A dual-donor hole transport material containing a phenothiazine structure, a preparation method thereof, and a perovskite solar cell |
CN111303011A (en) * | 2018-12-12 | 2020-06-19 | 乐金显示有限公司 | Organic compound, light-emitting diode and light-emitting device having the same |
WO2021152435A1 (en) * | 2020-01-27 | 2021-08-05 | Hikal Limited | Process for preparation of 5-bromo-1, 2, 3-trichlorobenzene |
-
2021
- 2021-12-19 CN CN202111557533.6A patent/CN114230470A/en active Pending
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1490302A (en) * | 2002-10-15 | 2004-04-21 | 协和化学株式会社 | Benzidine compound preparing method |
CN1506349A (en) * | 2002-12-11 | 2004-06-23 | 中国石油化工股份有限公司 | Prepn process of 4-amino diphenylamine |
KR20160106238A (en) * | 2015-03-02 | 2016-09-12 | (주)부흥산업사 | Novel aromatic amine derivatives for organic electroluminescent device |
CN106995461A (en) * | 2017-03-03 | 2017-08-01 | 中山大学 | A kind of Phosphine ligands of the structure containing benzofuran and its preparation method and application |
CN109467561A (en) * | 2018-11-19 | 2019-03-15 | 广东工业大学 | A dual-donor hole transport material containing a phenothiazine structure, a preparation method thereof, and a perovskite solar cell |
CN111303011A (en) * | 2018-12-12 | 2020-06-19 | 乐金显示有限公司 | Organic compound, light-emitting diode and light-emitting device having the same |
WO2021152435A1 (en) * | 2020-01-27 | 2021-08-05 | Hikal Limited | Process for preparation of 5-bromo-1, 2, 3-trichlorobenzene |
Non-Patent Citations (2)
Title |
---|
FANGYU DU ET AL.,: "imerization of Aromatic Compounds Using Palladium-Carbon-Catalyzed Suzuki–Miyaura Cross-Coupling by One-Pot Synthesis", 《SYNLETT》, vol. 29, pages 779 - 784 * |
张青山: "《有机合成反应基础》", 31 December 2004, 高等教育出版社, pages: 43 * |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
Gao et al. | A highly selective fluorescent chemosensor for iron ion based on 1H-imidazo [4, 5-b] phenazine derivative | |
CN105315264B (en) | A kind of N '-(Quinoline -2- methylene)- 7- diethylaminocoumarin -3- formylhydrazines and its preparation method and application | |
Adao et al. | CuII–salan compounds: Synthesis, characterization and evaluation of their potential as oxidation catalysts | |
CN107488147A (en) | A kind of fluorescence probe and preparation method and application | |
CN103254096B (en) | A kind of synthetic method of cold labeling basic orange II | |
CN110590784B (en) | Derivative based on pyrrolopyrroledione and preparation method and application thereof | |
CN113735829B (en) | Fluorescent reagent for detecting organic phosphate and preparation method thereof | |
CN110286105B (en) | A kind of fluorescent probe and preparation method thereof | |
CN104151327A (en) | Synthesis and separation method of trans-seven-membered-cucurbituril | |
CN108484414B (en) | Formaldehyde fluorescent probe and formaldehyde detection sheet based on tetraphenylethylene and preparation method thereof, and method of using formaldehyde detection sheet | |
CN107892654B (en) | Isolongifolane-based fluorescent acid-base indicator and synthetic method and application thereof | |
CN108863984B (en) | Thiazacrown ether-fluorenschiff base fluorescent molecular probe for detecting Mg2+, Fe3+, Cu2+ and preparation method | |
CN114230470A (en) | Synthetic method and application of stable isotope labeled benzidine | |
CN112300107B (en) | Triptycene functional material, preparation method and application thereof | |
CN109503604A (en) | Benzimidazole benzimidazole derivative and its synthetic method | |
CN118652196A (en) | A fluorescent probe for detecting lead ions in traditional Chinese medicine and a preparation method thereof | |
CN109232658B (en) | A kind of chiral rhodium complex and its preparation and application | |
CN113173883A (en) | 8-hydroxyquinoline functionalized column [5] arene, synthesis thereof and application thereof in detection and adsorption of ethylenediamine | |
CN111253443A (en) | Preparation method and application of a class of cyclometal iridium complexes modified with electron-withdrawing groups | |
CN107235962A (en) | A kind of enhanced fluorescence probe, its preparation method and application based on naphthalimide | |
CN113651821B (en) | A fluorescent probe based on diketopyrrolopyrrole derivatives and its application | |
CN105461726B (en) | The one-step method for synthesizing of the hydroxy-porphyrin of new type water-solubility eight | |
CN115286646A (en) | Probe for detecting amine compound residues in polyurethane, preparation method and application thereof | |
CN116068110B (en) | Synthesis and application of azide mass spectrometry probe | |
CN113979890A (en) | A kind of Schiff base ligand and its preparation method and application of multinuclear rare earth complex |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
CB02 | Change of applicant information | ||
CB02 | Change of applicant information |
Address after: Room 801, building 5, Changzhou inspection and testing industrial park, Changzhou City, Jiangsu Province 213000 Applicant after: Changzhou Manhag Testing Technology Co.,Ltd. Address before: 213000 Black Peony Science Park, Tianning District, Changzhou City, Jiangsu Province Applicant before: Manhag Testing Technology Co.,Ltd. |
|
TA01 | Transfer of patent application right | ||
TA01 | Transfer of patent application right |
Effective date of registration: 20230919 Address after: 101100 second floor, building 63, No. 15, Jingsheng South 4th Street, Jinqiao Science and technology industrial base, Tongzhou Park, Zhongguancun Science and Technology Park, Tongzhou District, Beijing Applicant after: Beijing Manhattan Biotechnology Co.,Ltd. Address before: Room 801, building 5, Changzhou inspection and testing industrial park, Changzhou City, Jiangsu Province 213000 Applicant before: Changzhou Manhag Testing Technology Co.,Ltd. |
|
RJ01 | Rejection of invention patent application after publication | ||
RJ01 | Rejection of invention patent application after publication |
Application publication date: 20220325 |