GB713255A - Improvements in and relating to methine dyes - Google Patents
Improvements in and relating to methine dyesInfo
- Publication number
- GB713255A GB713255A GB8139/51A GB813951A GB713255A GB 713255 A GB713255 A GB 713255A GB 8139/51 A GB8139/51 A GB 8139/51A GB 813951 A GB813951 A GB 813951A GB 713255 A GB713255 A GB 713255A
- Authority
- GB
- United Kingdom
- Prior art keywords
- prepared
- iodide
- general formula
- ethyl
- trimethylene
- 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.)
- Expired
Links
- 239000000975 dye Substances 0.000 title abstract 11
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 title abstract 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 abstract 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 20
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 18
- 238000010992 reflux Methods 0.000 abstract 13
- 150000003839 salts Chemical group 0.000 abstract 13
- 239000000298 carbocyanine Substances 0.000 abstract 12
- 235000019441 ethanol Nutrition 0.000 abstract 11
- 125000004429 atom Chemical group 0.000 abstract 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 6
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 abstract 6
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 abstract 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 abstract 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 4
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 abstract 4
- 238000010438 heat treatment Methods 0.000 abstract 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- 150000001299 aldehydes Chemical class 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000003118 aryl group Chemical group 0.000 abstract 3
- 150000003233 pyrroles Chemical class 0.000 abstract 3
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 abstract 2
- GJYHLESHXPAPRA-UHFFFAOYSA-N 1-(3,4,4a,5-tetrahydro-2h-quinolin-1-yl)ethanone Chemical compound C1C=CC=C2N(C(=O)C)CCCC21 GJYHLESHXPAPRA-UHFFFAOYSA-N 0.000 abstract 2
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical class C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 abstract 2
- HSJKGGMUJITCBW-UHFFFAOYSA-N 3-hydroxybutanal Chemical compound CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 abstract 2
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 abstract 2
- 239000005977 Ethylene Substances 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 abstract 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 2
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 abstract 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 abstract 2
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 abstract 2
- DXYYSGDWQCSKKO-UHFFFAOYSA-N methylbenzothiazole Natural products C1=CC=C2SC(C)=NC2=C1 DXYYSGDWQCSKKO-UHFFFAOYSA-N 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 235000009518 sodium iodide Nutrition 0.000 abstract 2
- 239000001117 sulphuric acid Substances 0.000 abstract 2
- 235000011149 sulphuric acid Nutrition 0.000 abstract 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 abstract 2
- 239000008096 xylene Substances 0.000 abstract 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 abstract 2
- ABFWVMFZVUBVKR-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline;hydrochloride Chemical compound Cl.C1=CC=C2CCCNC2=C1 ABFWVMFZVUBVKR-UHFFFAOYSA-N 0.000 abstract 1
- ORGVJFSJIVVAJU-UHFFFAOYSA-M 1,2-dimethylquinolin-1-ium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.C1=CC=CC2=[N+](C)C(C)=CC=C21 ORGVJFSJIVVAJU-UHFFFAOYSA-M 0.000 abstract 1
- RNTCWULFNYNFGI-UHFFFAOYSA-N 1-(2,3-dihydroindol-1-yl)ethanone Chemical compound C1=CC=C2N(C(=O)C)CCC2=C1 RNTCWULFNYNFGI-UHFFFAOYSA-N 0.000 abstract 1
- YXDQYLWDHRSJTD-UHFFFAOYSA-N 2,3-dimethyl-1-phenylpyrrole Chemical compound CC1=C(C)C=CN1C1=CC=CC=C1 YXDQYLWDHRSJTD-UHFFFAOYSA-N 0.000 abstract 1
- ASKXFFSMDYXORX-UHFFFAOYSA-N 2-(2-methylsulfanylbut-1-enyl)-1,3-benzothiazole Chemical compound CSC(=CC=1SC2=C(N1)C=CC=C2)CC ASKXFFSMDYXORX-UHFFFAOYSA-N 0.000 abstract 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 abstract 1
- JRMAQQQTXDJDNC-UHFFFAOYSA-M 2-ethoxy-2-oxoacetate Chemical compound CCOC(=O)C([O-])=O JRMAQQQTXDJDNC-UHFFFAOYSA-M 0.000 abstract 1
- FRWYFWZENXDZMU-UHFFFAOYSA-N 2-iodoquinoline Chemical compound C1=CC=CC2=NC(I)=CC=C21 FRWYFWZENXDZMU-UHFFFAOYSA-N 0.000 abstract 1
- ISIREYSCXHEQAD-UHFFFAOYSA-M 2-methyl-1-phenylquinolin-1-ium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.CC1=CC=C2C=CC=CC2=[N+]1C1=CC=CC=C1 ISIREYSCXHEQAD-UHFFFAOYSA-M 0.000 abstract 1
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 abstract 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 abstract 1
- JNOOPBCMWGHKBM-UHFFFAOYSA-M 6-chloro-1,2-dimethylquinolin-1-ium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.C1=C(Cl)C=CC2=[N+](C)C(C)=CC=C21 JNOOPBCMWGHKBM-UHFFFAOYSA-M 0.000 abstract 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 abstract 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 abstract 1
- 239000007868 Raney catalyst Substances 0.000 abstract 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 abstract 1
- 229910000564 Raney nickel Inorganic materials 0.000 abstract 1
- GANRMZBROZGBGJ-UHFFFAOYSA-N [I-].C(C)C=1C=CC=C2C=CC(=[NH+]C12)C Chemical compound [I-].C(C)C=1C=CC=C2C=CC(=[NH+]C12)C GANRMZBROZGBGJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 abstract 1
- 125000004659 aryl alkyl thio group Chemical group 0.000 abstract 1
- 125000005110 aryl thio group Chemical group 0.000 abstract 1
- 150000001555 benzenes Chemical class 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000001816 cooling Methods 0.000 abstract 1
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 abstract 1
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 1
- 238000001704 evaporation Methods 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 150000002391 heterocyclic compounds Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052740 iodine Inorganic materials 0.000 abstract 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 abstract 1
- 229910000000 metal hydroxide Inorganic materials 0.000 abstract 1
- 150000004692 metal hydroxides Chemical class 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- SQYNKIJPMDEDEG-UHFFFAOYSA-N paraldehyde Chemical compound CC1OC(C)OC(C)O1 SQYNKIJPMDEDEG-UHFFFAOYSA-N 0.000 abstract 1
- 229960003868 paraldehyde Drugs 0.000 abstract 1
- KLJOVDQWQVYFFR-UHFFFAOYSA-N perchloric acid;quinoline Chemical compound [O-]Cl(=O)(=O)=O.[NH+]1=CC=CC2=CC=CC=C21 KLJOVDQWQVYFFR-UHFFFAOYSA-N 0.000 abstract 1
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 abstract 1
- QWYZFXLSWMXLDM-UHFFFAOYSA-M pinacyanol iodide Chemical compound [I-].C1=CC2=CC=CC=C2N(CC)C1=CC=CC1=CC=C(C=CC=C2)C2=[N+]1CC QWYZFXLSWMXLDM-UHFFFAOYSA-M 0.000 abstract 1
- 230000001376 precipitating effect Effects 0.000 abstract 1
- 238000001556 precipitation Methods 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 150000003222 pyridines Chemical class 0.000 abstract 1
- 150000003248 quinolines Chemical class 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 abstract 1
- 239000012429 reaction media Substances 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- BAZAXWOYCMUHIX-UHFFFAOYSA-M sodium perchlorate Chemical compound [Na+].[O-]Cl(=O)(=O)=O BAZAXWOYCMUHIX-UHFFFAOYSA-M 0.000 abstract 1
- 229910001488 sodium perchlorate Inorganic materials 0.000 abstract 1
- 125000005504 styryl group Chemical group 0.000 abstract 1
- 125000000101 thioether group Chemical group 0.000 abstract 1
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 abstract 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- 239000011592 zinc chloride Substances 0.000 abstract 1
- 235000005074 zinc chloride Nutrition 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/14—Styryl dyes
- C09B23/145—Styryl dyes the ethylene chain carrying an heterocyclic residue, e.g. heterocycle-CH=CH-C6H5
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cosmetics (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Coloring (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US154883A US2646430A (en) | 1950-04-08 | 1950-04-08 | Quinoline dyes of the polymethine series and process of preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB713255A true GB713255A (en) | 1954-08-11 |
Family
ID=22553221
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8139/51A Expired GB713255A (en) | 1950-04-08 | 1951-04-09 | Improvements in and relating to methine dyes |
| GB21879/52A Expired GB713293A (en) | 1950-04-08 | 1951-04-09 | Improvements in and relating to methine dyes |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB21879/52A Expired GB713293A (en) | 1950-04-08 | 1951-04-09 | Improvements in and relating to methine dyes |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US2646430A (cg-RX-API-DMAC10.html) |
| BE (1) | BE502441A (cg-RX-API-DMAC10.html) |
| FR (1) | FR1053842A (cg-RX-API-DMAC10.html) |
| GB (2) | GB713255A (cg-RX-API-DMAC10.html) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2786054A (en) * | 1954-08-19 | 1957-03-19 | Eastman Kodak Co | Cyanines from triazolo bases |
| DE1072476B (cg-RX-API-DMAC10.html) * | 1957-06-20 | |||
| DE1240865B (de) * | 1961-06-29 | 1967-05-24 | Heyden Chem Fab | Verfahren zur Herstellung von Indolin-6-sulfonamid und seinen 1-Acylderivaten |
| US3637395A (en) * | 1970-04-09 | 1972-01-25 | Eastman Kodak Co | Silver halide emulsions containing cyclic enamine cyanine dyes |
| DE2351296C3 (de) * | 1973-10-12 | 1978-08-31 | Bayer Ag, 5090 Leverkusen | Kationische Farbstoffe, deren Herstellung und deren Verwendung |
| US5534416A (en) * | 1993-04-13 | 1996-07-09 | Molecular Probes, Inc. | Fluorescent viability assay using cyclic-substituted unsymmetrical cyanine dyes |
| US5658751A (en) * | 1993-04-13 | 1997-08-19 | Molecular Probes, Inc. | Substituted unsymmetrical cyanine dyes with selected permeability |
| US6147205A (en) * | 1995-12-15 | 2000-11-14 | Affymetrix, Inc. | Photocleavable protecting groups and methods for their use |
| US20110028350A1 (en) * | 1995-12-15 | 2011-02-03 | Affymetrix, Inc. | Photocleavable protecting groups |
| WO2002020150A2 (en) * | 2000-09-11 | 2002-03-14 | Affymetrix, Inc. | Photocleavable protecting groups |
| US7547775B2 (en) * | 2004-12-31 | 2009-06-16 | Affymetrix, Inc. | Parallel preparation of high fidelity probes in an array format |
| US8338093B2 (en) * | 2004-12-31 | 2012-12-25 | Affymetrix, Inc. | Primer array synthesis and validation |
| EP1885718B1 (en) | 2005-05-11 | 2017-03-15 | Life Technologies Corporation | Fluorescent chemical compounds having high selectivity for double stranded dna, and methods for their use |
| WO2010035589A1 (ja) * | 2008-09-25 | 2010-04-01 | 独立行政法人農業・食品産業技術総合研究機構 | 色素化合物及びその製造方法、並びに着色料 |
| CN115504933B (zh) * | 2022-10-13 | 2024-12-13 | 深圳万知达企业管理有限公司 | 一种多取代喹啉酮化合物的制备方法及其应用 |
-
0
- BE BE502441D patent/BE502441A/xx unknown
-
1950
- 1950-04-08 US US154883A patent/US2646430A/en not_active Expired - Lifetime
-
1951
- 1951-04-07 FR FR1053842D patent/FR1053842A/fr not_active Expired
- 1951-04-09 GB GB8139/51A patent/GB713255A/en not_active Expired
- 1951-04-09 GB GB21879/52A patent/GB713293A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE502441A (cg-RX-API-DMAC10.html) | |
| US2646430A (en) | 1953-07-21 |
| FR1053842A (fr) | 1954-02-05 |
| GB713293A (en) | 1954-08-11 |
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