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【结 构 式】 
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【分子编号】14153 【品名】4-Fluoronitrobenzene; 1-Fluoro-4-nitrobenzene 【CA登记号】350-46-9 |
【 分 子 式 】C6H4FNO2 【 分 子 量 】141.1017032 【元素组成】C 51.07% H 2.86% F 13.46% N 9.93% O 22.68% |
合成路线1
该中间体在本合成路线中的序号：(IV)Reaction of 1-methyl-4-piperidone (I) with phenyllithium (II) gives 1-methyl-4-phenyl-4-piperidinol (III), which is alkylated with (IV) in NaH/DMF to yield (V), followed by reduction with hydrazine/Raney-Ni.
| 【1】 Eistetter, K.; Kley, H.-P.; Menge, H.G.; Schaefer, H. (Byk Gulden Lomberg Chemische Fabrik GmbH); Anti-depressant and analgesic 4-phenoxypiperidines. US 4333942 . |
| 【2】 Menge, H.G.; Eistetter, K.; Schaefer, H.; Kley, H.-P.; B-777-81. Drugs Fut 1983, 8, 5, 387. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 10919 | 1-Methyl-4-piperidone; 1-Methyltetrahydro-4(1H)-pyridinone; N-Methyl-4-piperidone;1-methylpiperidin-4-one | 1445-73-4 | C6H11NO | 详情 | 详情 |
| (II) | 24014 | Phenyllithium | 591-51-5 | C6H5Li | 详情 | 详情 |
| (III) | 24016 | 1-methyl-4-phenyl-4-piperidinol | C12H17NO | 详情 | 详情 | |
| (IV) | 14153 | 4-Fluoronitrobenzene; 1-Fluoro-4-nitrobenzene | 350-46-9 | C6H4FNO2 | 详情 | 详情 |
| (V) | 36052 | 1-methyl-4-phenyl-4-piperidinyl 4-nitrophenyl ether; 1-methyl-4-(4-nitrophenoxy)-4-phenylpiperidine | C18H20N2O3 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(V)The synthesis of metabolites M-III, M-IV and M-V of pioglitazone has been reported: a) Synthesis of metabolite M-IV: The reduction of 5-acetyl-2-methylpyridine (I) with NaBH4 in cooled ethanol gives the corresponding 1-hydroxyethyl derivative (II), which is protected with chloromethyl methyl ether and NaH in DMF yielding the methoxymethyl ether (III). The hydroxymethylation of (III) with aqueous formaldehyde at 150-60 C affords the ethanol (IV), which is condensed with 4-fluoronitrobenzene (V) by means of NaH in cooled DMF giving 5-[1-(methoxymethoxy)ethyl]-2-[2-(4-nitrophenoxy)ethyl]pyridine (VI). The reduction of the nitro group of (VI) with H2 over Pd/C in ethyl acetate yields the corresponding amino compound (VII), which is diazotized with NaNO2 in aqueous HBr and condensed with methyl acrylate (VIII) by means of Cu2O to afford the 2-bromopropionate derivative (IX). The cyclization of (IX) with thiourea (X) by means of sodium acetate in refluxing ethanol gives the intermediate iminothiazolidinone (XI), which without isolation, is treated with refluxing 2N HCl to give metabolite M-IV. b) Synthesis of metabolite M-III: By oxidation of metabolite M-IV with the pyridine.sulfur trioxide complex in ethanol/dichloromethane/triethylamine
| 【1】 Momose, Y.; Sohda, T.; Meguro, K.; Hatanaka, C.; Ikeda, H.; Oi, S.; Studies on antidiabetic agents: Synthesis and biological activities of pioglitazone and related compounds. 11th Symp Med Chem (Dec 4-5, Tokushima) 1990, Abst P-11. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| M-IV | 63861 | 5-(4-{2-[5-(1-hydroxyethyl)-2-pyridinyl]ethoxy}benzyl)-1,3-thiazolidine-2,4-dione | C19H20N2O4S | 详情 | 详情 | |
| M-III | 63862 | 5-{4-[2-(5-acetyl-2-piperidinyl)ethoxy]benzyl}-1,3-thiazolidine-2,4-dione | C19H24N2O4S | 详情 | 详情 | |
| (I) | 14149 | 1-(6-Methyl-3-pyridinyl)-1-ethanone | C8H9NO | 详情 | 详情 | |
| (II) | 14150 | 1-(6-Methyl-3-pyridinyl)-1-ethanol | C8H11NO | 详情 | 详情 | |
| (III) | 14151 | 5-[1-(Methoxymethoxy)ethyl]-2-methylpyridine; Methoxymethyl 1-(6-methyl-3-pyridinyl)ethyl ether | C10H15NO2 | 详情 | 详情 | |
| (IV) | 14152 | 2-[5-[1-(Methoxymethoxy)ethyl]-2-pyridinyl]-1-ethanol | C11H17NO3 | 详情 | 详情 | |
| (V) | 14153 | 4-Fluoronitrobenzene; 1-Fluoro-4-nitrobenzene | 350-46-9 | C6H4FNO2 | 详情 | 详情 |
| (VI) | 14154 | 2-[5-[1-(Methoxymethoxy)ethyl]-2-pyridinyl]ethyl 4-nitrophenyl ether; 5-[1-(Methoxymethoxy)ethyl]-2-[2-(4-nitrophenoxy)ethyl]pyridine | C17H20N2O5 | 详情 | 详情 | |
| (VII) | 14155 | 4-(2-[5-[1-(Methoxymethoxy)ethyl]-2-pyridinyl]ethoxy)aniline; 4-(2-[5-[1-(Methoxymethoxy)ethyl]-2-pyridinyl]ethoxy)phenylamine | C17H22N2O3 | 详情 | 详情 | |
| (VIII) | 14156 | methyl acrylate | 96-33-3 | C4H6O2 | 详情 | 详情 |
| (IX) | 14157 | methyl 2-bromo-3-[4-(2-[5-[1-(methoxymethoxy)ethyl]-2-pyridinyl]ethoxy)phenyl]propanoate | C21H26BrNO5 | 详情 | 详情 | |
| (X) | 10180 | Thiourea | 62-56-6 | CH4N2S | 详情 | 详情 |
| (XI) | 14159 | 2-Imino-5-[4-(2-[5-[1-(methoxymethoxy)ethyl]-2-pyridinyl]ethoxy)benzyl]-1,3-thiazolan-4-one | C21H25N3O4S | 详情 | 详情 |
合成路线3
该中间体在本合成路线中的序号：(V)c) Synthesis of metabolite M-V: The reduction of 6-methylpyridine-3-carboxylic acid methyl ester (XII) with LiAlH4 in THF gives the corresponding hydroxymethyl derivative (XIII), which is protected with chloromethyl methyl ether as before yielding the methoxymethoxymethyl compound (XIV). Hydroxymethylation of (XIV) with formaldehyde as described affords the ethanol derivative (XV), which is condensed with 4-fluoronitrobenzene (V) as before giving 5-(hydroxymethyl)-2-[2-(4-nitrophenoxy)ethyl]pyridine (XVI). The deprotection of (XVI) with HCl in refluxing methanol yields the hydroxymethyl compound (XVII), which is treated with SOCl2 in refluxing chloroform to afford the chloromethyl compound (XVIII). The reaction of (XVIII) with KCN in hot DMF gives the corresponding cyanomethyl derivative (XIX), which by reduction of the NO2 group with H2 over Pd/C in ethyl acetate yields the amino derivative (XX). The diazotation of (XX) with NaNO2 in aqueous HBr followed by condensation with methyl acrylate as before affords the 2-bromopropionate (XXI), which is cyclized with thiourea (X) as reported to give iminothiazolidinone derivative (XXII). Finally, the hydrolysis of the cyano gives Metabolite M-V.
| 【1】 Momose, Y.; Sohda, T.; Meguro, K.; Hatanaka, C.; Ikeda, H.; Oi, S.; Studies on antidiabetic agents: Synthesis and biological activities of pioglitazone and related compounds. 11th Symp Med Chem (Dec 4-5, Tokushima) 1990, Abst P-11. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| M-V | 63863 | 2-[6-(2-{4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy}ethyl)-3-pyridinyl]acetic acid | C19H18N2O5S | 详情 | 详情 | |
| (V) | 14153 | 4-Fluoronitrobenzene; 1-Fluoro-4-nitrobenzene | 350-46-9 | C6H4FNO2 | 详情 | 详情 |
| (VIII) | 14156 | methyl acrylate | 96-33-3 | C4H6O2 | 详情 | 详情 |
| (X) | 10180 | Thiourea | 62-56-6 | CH4N2S | 详情 | 详情 |
| (XII) | 14160 | methyl 6-methylnicotinate | 5470-70-2 | C8H9NO2 | 详情 | 详情 |
| (XIII) | 14161 | (6-Methyl-3-pyridinyl)methanol | C7H9NO | 详情 | 详情 | |
| (XIV) | 14162 | Methoxymethyl (6-methyl-3-pyridinyl)methyl ether; 5-[(Methoxymethoxy)methyl]-2-methylpyridine | C9H13NO2 | 详情 | 详情 | |
| (XV) | 14163 | 2-[5-[(Methoxymethoxy)methyl]-2-pyridinyl]-1-ethanol | C10H15NO3 | 详情 | 详情 | |
| (XVI) | 14164 | 5-[(Methoxymethoxy)methyl]-2-[2-(4-nitrophenoxy)ethyl]pyridine; 2-[5-[(Methoxymethoxy)methyl]-2-pyridinyl]ethyl 4-nitrophenyl ether | C16H18N2O5 | 详情 | 详情 | |
| (XVII) | 14165 | [6-[2-(4-Nitrophenoxy)ethyl]-3-pyridinyl]methanol | C14H14N2O4 | 详情 | 详情 | |
| (XVIII) | 14166 | 2-[5-(Chloromethyl)-2-pyridinyl]ethyl 4-nitrophenyl ether; 5-(Chloromethyl)-2-[2-(4-nitrophenoxy)ethyl]pyridine | C14H13ClN2O3 | 详情 | 详情 | |
| (XIX) | 14167 | 2-[6-[2-(4-Nitrophenoxy)ethyl]-3-pyridinyl]acetonitrile | C15H13N3O3 | 详情 | 详情 | |
| (XX) | 14168 | 2-[6-[2-(4-Aminophenoxy)ethyl]-3-pyridinyl]acetonitrile | C15H15N3O | 详情 | 详情 | |
| (XXI) | 14169 | methyl 2-bromo-3-(4-[2-[5-(cyanomethyl)-2-pyridinyl]ethoxy]phenyl)propanoate | C19H19BrN2O3 | 详情 | 详情 | |
| (XXII) | 14170 | 2-[6-(2-[4-[(2-Imino-4-oxo-1,3-thiazolan-5-yl)methyl]phenoxy]ethyl)-3-pyridinyl]acetonitrile | C19H18N4O2S | 详情 | 详情 |
合成路线4
该中间体在本合成路线中的序号：(II)The condensation of 2-(5-ethyl-2-pyridyl)ethanol (I) with 4-fluoronitrobenzene (II) by means of NaH in DMF gives 4-[2-(5-ethyl-2-pyridyl)ethoxy]nitrobenzene (III), which is reduced with H2 over Pd/C in methanol to yield the corresponding aniline (IV). The reaction of (IV) with NaNO2/HBr and methyl acrylate (V) in acetone/methanol affords the 2-bromopropionate derivative (VI), which is cyclized with thiourea (VII) by means of NaOAc in refluxing ethanol to provide the 2-imino-4-thiazolidinone (VIII). Finally, this compound is hydrolyzed with refluxing 2N HCl.
| 【1】 Meguro, K.; Fujita, T. (Takeda Chemical Industries, Ltd.); Thiazolidinedione derivs., their production and use. EP 0193256; ES 8705886; JP 1986267580; US 4687777 . |
| 【2】 Sohda, T.; Momose, Y.; Meguro, K.; Kawamatsu, Y.; Sugiyama, Y.; Ikeda, H.; Studies on antidiabetic agents. Synthesis and hypoglycemic activity of 5-[4-(pyridylalkoxy)benzyl]-2,4-thiazolidinediones. Arzneim-Forsch Drug Res 1990, 40, 1, 37. |
| 【3】 Prous, J.; Castaner, J.; PIOGLITAZONE HYDROCHLORIDE < Prop INNM; USAN >. Drugs Fut 1990, 15, 11, 1080. |
| 【4】 Meguro, K.; Momose, Y.; Sohda, T.; Oi, S.; Ikeda, H.; Hatanaka, C.; Studies on antidiabetic agents. X. Synthesis and biological activities of pioglitazone and related compounds. Chem Pharm Bull 1991, 39, 6, 1440-5. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 14139 | 2-(5-Ethyl-2-pyridinyl)-1-ethanol | 5223-06-3 | C9H13NO | 详情 | 详情 |
| (II) | 14153 | 4-Fluoronitrobenzene; 1-Fluoro-4-nitrobenzene | 350-46-9 | C6H4FNO2 | 详情 | 详情 |
| (III) | 62867 | 5-ethyl-2-[2-(4-nitrophenoxy)ethyl]pyridine; 2-(5-ethyl-2-pyridinyl)ethyl 4-nitrophenyl ether | C15H16N2O3 | 详情 | 详情 | |
| (IV) | 62868 | 4-[2-(5-ethyl-2-pyridinyl)ethoxy]aniline; 4-[2-(5-ethyl-2-pyridinyl)ethoxy]phenylamine | C15H18N2O | 详情 | 详情 | |
| (V) | 14156 | methyl acrylate | 96-33-3 | C4H6O2 | 详情 | 详情 |
| (VI) | 62869 | methyl 2-bromo-3-{4-[2-(5-ethyl-2-pyridinyl)ethoxy]phenyl}propanoate | C19H22BrNO3 | 详情 | 详情 | |
| (VII) | 10180 | Thiourea | 62-56-6 | CH4N2S | 详情 | 详情 |
| (VIII) | 62870 | 5-{4-[2-(5-ethyl-2-pyridinyl)ethoxy]benzyl}-2-imino-1,3-thiazolidin-4-one | C19H21N3O2S | 详情 | 详情 |
合成路线5
该中间体在本合成路线中的序号：(II)The condensation of mercapto benzothiazole (I) with 4-fluoronitrobenzene (II) afforded the 4-nitrophenyl thioether (III). After reduction of the nitro group of (III) with iron in HOAc, the resulting aniline (IV) was acylated with the dichloroisatoic anhydride (V) to produce the anthranylamide (VI). This was finally condensed with 3,5-dichloro-2-hydroxybenzenesulfonyl chloride (VII) to yield the corresponding sulfonamide.
| 【1】 Dumas, J.; Witowsky, J.; Hatoum-Mokdad, H.; Sibley, R.; Chen, J.; Dixon, B.; Wong, S.; Konig, G.; Britelli, D.; Synthesis and structure activity relationships of novel small molecule cathepsin D inhibitors. Bioorg Med Chem Lett 1999, 9, 17, 2531. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 34296 | 6-ethoxy-1,3-benzothiazol-2-ylhydrosulfide; 6-ethoxy-1,3-benzothiazole-2-thiol | 120-53-6 | C9H9NOS2 | 详情 | 详情 |
| (II) | 14153 | 4-Fluoronitrobenzene; 1-Fluoro-4-nitrobenzene | 350-46-9 | C6H4FNO2 | 详情 | 详情 |
| (III) | 46843 | 6-ethoxy-2-[(4-nitrophenyl)sulfanyl]-1,3-benzothiazole; ethyl 2-[(4-nitrophenyl)sulfanyl]-1,3-benzothiazol-6-yl ether | C15H12N2O3S2 | 详情 | 详情 | |
| (IV) | 46844 | 4-[(6-ethoxy-1,3-benzothiazol-2-yl)sulfanyl]aniline; 4-[(6-ethoxy-1,3-benzothiazol-2-yl)sulfanyl]phenylamine | C15H14N2OS2 | 详情 | 详情 | |
| (V) | 46845 | 3,5-Dichloroisatoic anhydride; 6,8-dichloro-2H-3,1-benzoxazine-2,4(1H)-dione | 4693-00-9 | C8H3Cl2NO3 | 详情 | 详情 |
| (VI) | 46846 | 2-amino-3,5-dichloro-N-[4-[(6-ethoxy-1,3-benzothiazol-2-yl)sulfanyl]phenyl]benzamide | C22H17Cl2N3O2S2 | 详情 | 详情 | |
| (VII) | 46847 | 3,5-dichloro-2-hydroxybenzenesulfonyl chloride | 23378-88-3 | C6H3Cl3O3S | 详情 | 详情 |
合成路线6
该中间体在本合成路线中的序号：(I)The condensation between 4-fluoronitrobenzene (I) and tetrazole (II) provided a mixture of regioisomeric (4-nitrophenyl)tetrazoles (III) and (IV). Reduction of this mixture employing hydrazine and FeCl3 gave the corresponding mixture of amino derivatives from which the required isomer (V) was isolated by column chromatography. Alternatively, 4-nitroaniline (VI) was converted into the desired (4-nitrophenyl)tetrazole regioisomer (III) by reaction with sodium azide and trimethyl orthoformate in HOAc. Subsequent reduction of the nitro group of (III) employing hydrazine and FeCl3 gave aniline (V). This compound was also obtained by another alternative procedure consisting in protection of 4-nitroaniline (VI) as the N,N-dibenzyl amine (VII), followed by reduction of the nitro group and cyclization with NaN3 and trimethyl orthoformate to afford tetrazole (VIII). Further hydrogenolysis of the benzyl protecting groups of (VIII) yielded 1-(4-aminophenyl)tetrazole (V). Aniline (V) was then converted to the intermediate phenyl carbamate (IX) by treatment with phenyl chloroformate in pyridine. Optionally, the intermediate phenyl carbamate (IX) was converted into the aryl imidazolone (XII) by condensation with 2,2-diethoxyethylamine (X) and then acid-catalyzed cyclization of the resulting N-(2,2-diethoxyethyl)urea (XI) to give (XII).
| 【4】 Itoh, K.; Okonogi, K.; Tasaka, A. (Takeda Chemical Industries, Ltd.); Azole cpds., their production and use. EP 0809640; JP 1997183769; WO 9625410 . |
| 【5】 Kitazaki, T.; Matsushita, Y.; Hosono, H.; Itoh, K.; Mitsudera, H. (Takeda Chemical Industries, Ltd.); Triazole derivs. and their production. EP 0884311 . |
| 【1】 Ichikawa, T.; Matsushita, Y.; Yamada, M.; Tasaka, A.; Yamaguchi, M.; Itoh, K.; Okonogi, K.; Kitazaki, T.; TAK-456 and the water-soluble prodrug TAK-457, new antifungal triazoles: Synthesis and in vitro antifungal activity. 40th Intersci Conf Antimicrob Agents Chemother (Sept 17 2000, Toronto) 2000, Abst F-1085. |
| 【2】 Ichikawa, T.; et al.; Optically active antifungal azoles. XI. An alternative synthetic route for 1-[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-3-[4-(1H-1-tetrazolyl)phenyl]-2-imidazolidinone (TAK-456) and its analog. Chem Pharm Bull 2000, 48, 12, 1947. |
| 【3】 Hosono, H.; Itoh, K.; Kitazaki, T.; Ichikawa, T.; Okonogi, K.; Tasaka, A.; Matsushita, Y.; Hayashi, R.; Optically active antifungal azoles. X. Synthesis and antifungal activity of N-[4-(azolyl)phenyl] and N-[4-(azolylmethyl)phenyl]-N'[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H,1,2,4-triazol-1-yl)propyl]-azolones. Chem Pharm Bull 2000, 48, 12, 1935. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 14153 | 4-Fluoronitrobenzene; 1-Fluoro-4-nitrobenzene | 350-46-9 | C6H4FNO2 | 详情 | 详情 |
| (II) | 32408 | 1H-1,2,3,4-tetraazole; Tetrazole | 288-94-8 | CH2N4 | 详情 | 详情 |
| (III) | 45555 | 1-(4-nitrophenyl)-1H-1,2,3,4-tetraazole | C7H5N5O2 | 详情 | 详情 | |
| (IV) | 45556 | 2-(4-nitrophenyl)-2H-1,2,3,4-tetraazole | 67-97-0 | C7H5N5O2 | 详情 | 详情 |
| (V) | 45557 | 4-(1H-1,2,3,4-tetraazol-1-yl)phenylamine; 4-(1H-1,2,3,4-tetraazol-1-yl)aniline | C7H7N5 | 详情 | 详情 | |
| (VI) | 15547 | 4-nitrophenylamine; p-Nitroaniline; 4-nitroaniline | 100-01-6 | C6H6N2O2 | 详情 | 详情 |
| (VII) | 45558 | N,N-dibenzyl-N-(4-nitrophenyl)amine; N,N-dibenzyl-4-nitroaniline | C20H18N2O2 | 详情 | 详情 | |
| (VIII) | 45559 | N,N-dibenzyl-N-[4-(1H-1,2,3,4-tetraazol-1-yl)phenyl]amine; N,N-dibenzyl-4-(1H-1,2,3,4-tetraazol-1-yl)aniline | C21H19N5 | 详情 | 详情 | |
| (IX) | 45560 | phenyl 4-(1H-1,2,3,4-tetraazol-1-yl)phenylcarbamate | C14H11N5O2 | 详情 | 详情 | |
| (X) | 10331 | 2,2-Diethoxy-1-ethanamine; 2,2-Diethoxyethylamine; Aminoacetaldehyde diethyl acetal | 645-36-3 | C6H15NO2 | 详情 | 详情 |
| (XI) | 45561 | N-(2,2-diethoxyethyl)-N'-[4-(1H-1,2,3,4-tetraazol-1-yl)phenyl]urea | C14H20N6O3 | 详情 | 详情 | |
| (XII) | 45562 | 1-[4-(1H-1,2,3,4-tetraazol-1-yl)phenyl]-1,3-dihydro-2H-imidazol-2-one | C10H8N6O | 详情 | 详情 |
合成路线7
该中间体在本合成路线中的序号：(II)The reaction of the sodium salt of 2-methyl-4-nitroimidazole (I) with 4-fluoronitrobenzol (II) gives nitrefazole.
合成路线8
该中间体在本合成路线中的序号：(IV)In an alternative method, p-nitroaniline (I) is reacted with ethylene oxide (II) to afford diol (III). This compound can also be prepared by condensation of 1-fluoro-4-nitrobenzene (IV) with diethanolamine (V). Chlorination of diol (III) to provide (VI) is accomplished with either mesyl chloride or SOCl2 in the presence of pyridine. Then, nitro group reduction in (VI) by means of iron and HCl affords aniline (VII).
| 【1】 Jordan, A.M.; Khan, T.H.; Malkin, H.; Osborn, H.M.I.; Synthesis and analysis of urea and carbamate prodrugs as candidates for melanocyte-directed enzyme prodrug therapy (MDEPT). Bioorg Med Chem 2002, 10, 8, 2625. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 15547 | 4-nitrophenylamine; p-Nitroaniline; 4-nitroaniline | 100-01-6 | C6H6N2O2 | 详情 | 详情 |
| (II) | 10393 | Oxirane; Ethylene oxide | 75-21-8 | C2H4O | 详情 | 详情 |
| (III) | 64080 | 2-[(2-hydroxyethyl)-4-nitroanilino]-1-ethanol | C10H14N2O4 | 详情 | 详情 | |
| (IV) | 14153 | 4-Fluoronitrobenzene; 1-Fluoro-4-nitrobenzene | 350-46-9 | C6H4FNO2 | 详情 | 详情 |
| (V) | 24273 | 2-[(2-hydroxyethyl)amino]-1-ethanol | 111-42-2 | C4H11NO2 | 详情 | 详情 |
| (VI) | 64081 | N,N-bis(2-chloroethyl)-4-nitroaniline; N,N-bis(2-chloroethyl)-N-(4-nitrophenyl)amine | C10H12Cl2N2O2 | 详情 | 详情 | |
| (VII) | 64082 | N~1~,N~1~-bis(2-chloroethyl)-1,4-benzenediamine; N-(4-aminophenyl)-N,N-bis(2-chloroethyl)amine | C10H14Cl2N2 | 详情 | 详情 |