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Heterocyclic Compounds

Heterocyclic compounds are a class of compounds that consist of carbon atoms and non-carbon atoms altogether forming a cyclic skeletal structure. These non-carbon atoms are collectively referred to as a heteroatom. The common heteroatoms include nitrogen, oxygen, and sulfur. Lactones, lactams, cyclic ethers that we’ve already learned are heterocyclic compounds. With similar properties of congeneric open-chain compounds, they will be discussed in corresponding chapters. This chapter will mainly discuss heterocyclic compounds with relatively stable ring system and with a certain degree of aromaticity, also known as aromatic heterocyclic compound.

There are many kinds and a large number of heterocyclic compounds widely distributed in nature. Many natural heterocyclic compounds in animals and plants play an important physiological role in the body. For example, heterocyclic structure exists in chlorophyll in plants, hemoglobin in animal blood, alkaloids and glycosides as the active ingredient in herbs, some antibiotics and vitamins, certain composition of amino acids in protein and bases in nucleotide. About half of the existing medicines have heterocyclic structures. Thus, heterocyclic compounds play an important role in organic compounds especially in organic medicines.

The most common and also the most important heterocyclic compounds are that with five-membered or six-membered heterocyclic ring and their fused heterocyclic compounds. Therefore, according to the size of the ring, heterocyclic compounds can be divided into five-membered compounds and six-membered heterocyclic compounds. E.g., furan, thiophene, pyrrole, imidazole, triazole and their fused heterocyclic compounds, indole, benzimidazole and diphenylene-oxide are all five-membered heterocyclic compounds, while pyridine, pyrimidine and their fused heterocyclic compounds, quinoline and quinazoline are all six-membered heterocyclic compounds.

According to the number of hetero atoms, five-membered compounds and six-membered heterocyclic compounds can be divided into one-hetero-atom-containing heterocyclic compounds and two-hetero-atom-containing and several-hetero-atom-containing heterocyclic compounds. E.g., furan, thiophene, pyridine, indole, quinoline, dibenzofuran, etc. are one-hetero-atom-containing heterocyclic compounds; imidazole, pyrimidine, benzimidazole, quinazoline, etc. are two-hetero-atom-containing heterocyclic compounds; purine, comprising more than two hetero atoms, is a several-hetero-atom-containing heterocyclic compound. According to the form of the ring in the molecule, heterocyclic compounds can be divided into single-heterocyclic compounds and fused heterocyclic compounds. E.g., furan, pyridine, pyrimidine, imidazole, etc. are single-heterocyclic compounds and indole, quinoline, dibenzofuran, purines, etc. are fused heterocyclic compounds.

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Structure Chemical Name CAS MF
2-Bromo-5-(piperidon-1-yl)pyridine 2-Bromo-5-(piperidon-1-yl)pyridine 1209457-82-8 C10H11BrN2O
2-Bromo-5-ethylpyridine-4-boronic acid pinacol ester 2-Bromo-5-ethylpyridine-4-boronic acid pinacol ester 1402226-91-8 C13H19BBrNO2
2-bromo-6-(1,4-dioxan-2-yl)pyridine 2-bromo-6-(1,4-dioxan-2-yl)pyridine 1622834-82-5 C9H10BrNO2
2-Bromo-6-(hydroxymethyl)pyridine-4-boronic acid pinacol ester 2-Bromo-6-(hydroxymethyl)pyridine-4-boronic acid pinacol ester 2223046-54-4 C12H17BBrNO3
2-Bromo-6-(sec-butyl)pyridine-4-boronic acid pinacol ester 2-Bromo-6-(sec-butyl)pyridine-4-boronic acid pinacol ester 2223003-00-5 C15H23BBrNO2
2-Bromo-6-cyanopyridine-4-boronic acid pinacol ester 2-Bromo-6-cyanopyridine-4-boronic acid pinacol ester 2223044-64-0 C12H14BBrN2O2
2-Chloro-3-(2-methoxyphenyl)pyridine 2-Chloro-3-(2-methoxyphenyl)pyridine 1225682-75-6 C12H10ClNO
2-Chloro-3-(2-trifluoromethylphenyl)pyridine 2-Chloro-3-(2-trifluoromethylphenyl)pyridine 1226329-75-4 C12H7ClF3N
2-Chloro-3-(cyclobutyl)pyridine 2-Chloro-3-(cyclobutyl)pyridine 1417519-36-8 C9H10ClN
2-Chloro-3-(n-propyl)pyridine 2-Chloro-3-(n-propyl)pyridine 1417518-69-4 C8H10ClN
2-chloro-4-(1H-2-methylimidazol-1-yl)-6-cyclopropylpyrimidine 2-chloro-4-(1H-2-methylimidazol-1-yl)-6-cyclopropylpyrimidine 1412955-43-1 C11H11ClN4
2-chloro-4-(1H-4-methylimidazol-1-yl)-6-(tert-butyl)pyrimidine 2-chloro-4-(1H-4-methylimidazol-1-yl)-6-(tert-butyl)pyrimidine 1412958-60-1 C12H15ClN4
2-Chloro-4-(1H-pyridin-2-one)-6-methylpyrimidine 2-Chloro-4-(1H-pyridin-2-one)-6-methylpyrimidine 1412952-92-1 C10H8ClN3O
2-Chloro-4-(1H-pyrrol-1-yl)-6-(iso-propyl)pyrimidine 2-Chloro-4-(1H-pyrrol-1-yl)-6-(iso-propyl)pyrimidine 1412961-39-7 C11H12ClN3
2-Chloro-4-(2-fluorophenyl)-6-methylpyrimidine 2-Chloro-4-(2-fluorophenyl)-6-methylpyrimidine 1412953-40-2 C11H8ClFN2
2-Chloro-4-(2-furyl)-6-methylpyrimidine 2-Chloro-4-(2-furyl)-6-methylpyrimidine 1412956-41-2 C9H7ClN2O
2-Chloro-4-(2-pyridyl)-1,3,5-triazine 2-Chloro-4-(2-pyridyl)-1,3,5-triazine 1417518-59-2 C8H5ClN4
2-Chloro-4-(2-tolyl)-1,3,5-triazine 2-Chloro-4-(2-tolyl)-1,3,5-triazine 1417517-82-8 C10H8ClN3
2-Chloro-4-(3-chlorophenyl)-6-methylpyrimidine 2-Chloro-4-(3-chlorophenyl)-6-methylpyrimidine 897445-46-4 C11H8Cl2N2
2-Chloro-4-(3-furyl)-6-methylpyrimidine 2-Chloro-4-(3-furyl)-6-methylpyrimidine 1412959-26-2 C9H7ClN2O
2-Chloro-4-(3-thienyl)-1,3,5-triazine 2-Chloro-4-(3-thienyl)-1,3,5-triazine 1417518-61-6 C7H4ClN3S
2-Chloro-4-(3-tolyl)-1,3,5-triazine 2-Chloro-4-(3-tolyl)-1,3,5-triazine 1417519-21-1 C10H8ClN3
2-chloro-4-(4-methylpiperidin-1-yl)-6-(tert-butyl)pyrimidine 2-chloro-4-(4-methylpiperidin-1-yl)-6-(tert-butyl)pyrimidine 1412958-35-0 C14H22ClN3
2-Chloro-4-(5-pyrimidyl)-1,3,5-triazine 2-Chloro-4-(5-pyrimidyl)-1,3,5-triazine 1417518-12-7 C7H4ClN5
2-chloro-4-(cyclohexyl)-6-(tert-butyl)pyrimidine 2-chloro-4-(cyclohexyl)-6-(tert-butyl)pyrimidine 1412959-05-7 C14H21ClN2
2-Chloro-4-(pyridin-3-yl)-6-(iso-propyl)pyrimidine 2-Chloro-4-(pyridin-3-yl)-6-(iso-propyl)pyrimidine 1412953-45-7 C12H12ClN3
2-Chloro-4-(tert-butoxy)-6-(iso-propyl)pyrimidine 2-Chloro-4-(tert-butoxy)-6-(iso-propyl)pyrimidine 1412958-33-8 C11H17ClN2O
2-chloro-4-cyclohexyl-6-cyclopropylpyrimidine 2-chloro-4-cyclohexyl-6-cyclopropylpyrimidine 1412961-38-6 C13H17ClN2
2-cyclobutoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine 2-cyclobutoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine 1353877-85-6 C14H21BN2O3
2-cyclobutyl-4-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2-cyclobutyl-4-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2223045-20-1 C15H21BFNO2
2-cyclohexyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole 2-cyclohexyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole 1402166-60-2 C15H24BNO2S
2-cyclopentyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole 2-cyclopentyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole 2096335-20-3 C14H22BNO2S
2-cyclopropyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile 2-cyclopropyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile 2223041-07-2 C16H20BNO2
2-cyclopropyl-6-(1,4-dioxan-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2-cyclopropyl-6-(1,4-dioxan-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2222996-06-5 C18H26BNO4
2-Ethyl-5-trifluoromethylpyridine-3-boronic acid pinacol ester 2-Ethyl-5-trifluoromethylpyridine-3-boronic acid pinacol ester 2223047-56-9 C14H19BF3NO2
2-Fluoro-3-bromo-4-(sec-butyl)pyridine 2-Fluoro-3-bromo-4-(sec-butyl)pyridine 1622835-53-3 C9H11BrFN
2-Fluoro-6-(2-furyl)pyridine 2-Fluoro-6-(2-furyl)pyridine 1563530-60-8 C9H6FNO
2-Fluoro-6-(2-thienyl)pyridine-3-boronic acid pinacol ester 2-Fluoro-6-(2-thienyl)pyridine-3-boronic acid pinacol ester 2223044-51-5 C15H17BFNO2S
2-Fluoro-6-(3-tolyl)pyridine-3-boronic acid pinacol ester 2-Fluoro-6-(3-tolyl)pyridine-3-boronic acid pinacol ester 2223012-40-4 C18H21BFNO2
2-Fluoro-6-(iso-butyl)pyridine-3-boronic acid pinacol ester 2-Fluoro-6-(iso-butyl)pyridine-3-boronic acid pinacol ester 2223050-11-9 C15H23BFNO2
2-Fluoro-6-(methoxycarbonyl)pyridine-3-boronic acid pinacol ester 2-Fluoro-6-(methoxycarbonyl)pyridine-3-boronic acid pinacol ester 2223052-86-4 C13H17BFNO4
2-Fluoro-6-(tert-butyl)pyridine 2-Fluoro-6-(tert-butyl)pyridine 1501904-66-0 C9H12FN
2-Fluoro-6-(thiazol-4-yl)pyridine 2-Fluoro-6-(thiazol-4-yl)pyridine 1563529-25-8 C8H5FN2S
2-Fluoro-6-(thiazol-5-yl)pyridine-3-boronic acid pinacol ester 2-Fluoro-6-(thiazol-5-yl)pyridine-3-boronic acid pinacol ester 2223036-00-6 C14H16BFN2O2S
2-fluoro-6-isopropyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2-fluoro-6-isopropyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2223048-99-3 C14H21BFNO2
2-fluoro-6-propyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2-fluoro-6-propyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2223041-51-6 C14H21BFNO2
2-Hydroxy-3-(3-tolyl)pyridine 2-Hydroxy-3-(3-tolyl)pyridine 143074-75-3 C12H11NO
2-Hydroxy-3-(cyclobutyl)pyridine 2-Hydroxy-3-(cyclobutyl)pyridine 1417517-81-7 C9H11NO
2-hydroxy-4-(1H-4-methylpyrozol-1-yl)-6-(tert-butyl)pyrimidine 2-hydroxy-4-(1H-4-methylpyrozol-1-yl)-6-(tert-butyl)pyrimidine 1412957-17-5 C12H16N4O
2-Hydroxy-4-(1H-imidazol-1-yl)-6-methylpyrimidine 2-Hydroxy-4-(1H-imidazol-1-yl)-6-methylpyrimidine 1412952-99-8 C8H8N4O
2-hydroxy-4-(2-chlorophenyl)-6-cyclopropylpyrimidine 2-hydroxy-4-(2-chlorophenyl)-6-cyclopropylpyrimidine 1412955-64-6 C13H11ClN2O
2-hydroxy-4-(2-fluorophenyl)-6-methylpyrimidine 2-hydroxy-4-(2-fluorophenyl)-6-methylpyrimidine 1412958-79-2 C11H9FN2O
2-Hydroxy-4-(2-thienyl)-6-methylpyrimidine 2-Hydroxy-4-(2-thienyl)-6-methylpyrimidine 26963-45-1 C9H8N2OS
2-Hydroxy-4-(2-trifluoromethylphenyl)-6-(iso-propyl)pyrimidine 2-Hydroxy-4-(2-trifluoromethylphenyl)-6-(iso-propyl)pyrimidine 1412955-13-5 C14H13F3N2O
2-Hydroxy-4-(3-methoxyphenyl)pyrimidine 2-Hydroxy-4-(3-methoxyphenyl)pyrimidine 1159817-10-3 C11H10N2O2
2-Hydroxy-4-(3-methylpiperidin-1-yl)-6-methylpyrimidine 2-Hydroxy-4-(3-methylpiperidin-1-yl)-6-methylpyrimidine 1412958-64-5 C11H17N3O
2-hydroxy-4-(iso-propyl)-6-(tert-butyl)pyrimidine 2-hydroxy-4-(iso-propyl)-6-(tert-butyl)pyrimidine 1412959-39-7 C11H18N2O
2-Hydroxy-4-(n-propyl)pyrimidine 2-Hydroxy-4-(n-propyl)pyrimidine 1215073-86-1 C7H10N2O
2-hydroxy-4-(pyridin-4-yl)-6-cyclopropylpyrimidine 2-hydroxy-4-(pyridin-4-yl)-6-cyclopropylpyrimidine 1412955-88-4 C12H11N3O
2-hydroxy-4-(pyrimindin-5-yl)-6-(tert-butyl)pyrimidine 2-hydroxy-4-(pyrimindin-5-yl)-6-(tert-butyl)pyrimidine 1412954-27-8 C12H14N4O
2-Hydroxy-4-cyclohexyl-6-methylpyrimidine 2-Hydroxy-4-cyclohexyl-6-methylpyrimidine 1412958-07-6 C11H16N2O
2-Hydroxy-5-(5-methyl-2-pyridyl)pyrazine 2-Hydroxy-5-(5-methyl-2-pyridyl)pyrazine 1159819-22-3 C10H9N3O
2-isobutyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine 2-isobutyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine 2223048-95-9 C14H23BN2O2
2-methoxy-6-(tetrahydrofuran-3-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2-methoxy-6-(tetrahydrofuran-3-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2223003-86-7 C16H24BNO4
2-methyl-4-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)thiazole 2-methyl-4-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)thiazole 1402174-35-9 C15H19BN2O2S
2-Methyl-6-(tert-butoxy)pyridine-4-boronic acid pinacol ester 2-Methyl-6-(tert-butoxy)pyridine-4-boronic acid pinacol ester 1402166-45-3 C16H26BNO3
2-methyl-6-(tetrahydro-2H-pyran-3-yl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2-methyl-6-(tetrahydro-2H-pyran-3-yl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2222996-85-0 C17H26BNO3
2-N-ETHYL-2-N-METHYLPYRIDINE-2,6-DIAMINE 2-N-ETHYL-2-N-METHYLPYRIDINE-2,6-DIAMINE 1446410-05-4 C8H13N3
3-(2-oxopyridin-1(2H)-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile 3-(2-oxopyridin-1(2H)-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile 2223053-18-5 C18H19BN2O3
3-(2-Trifluoromethylphenyl)pyridine-2-boronic acid pinacol ester 3-(2-Trifluoromethylphenyl)pyridine-2-boronic acid pinacol ester 2223012-15-3 C18H19BF3NO2
3-(butan-2-yl-d9)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 3-(butan-2-yl-d9)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2241875-32-9 C15H15BD9NO2
3-(Cyclobutyl)pyridine-4-boronic acid pinacol ester 3-(Cyclobutyl)pyridine-4-boronic acid pinacol ester 2223052-17-1 C15H22BNO2
3-(CYCLOPENTYLOXY)PYRIDIN-2-AMINE 3-(CYCLOPENTYLOXY)PYRIDIN-2-AMINE 1152595-98-6 C10H14N2O
3-(piperidin-1-yl-d10)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 3-(piperidin-1-yl-d10)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2241875-15-8 C16H25BN2O2
3-(propyl-d7)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 3-(propyl-d7)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2241875-27-2 C14H15BD7NO2
3-(PYRIMIDIN-5-YL)PYRIDIN-2-AMINE 3-(PYRIMIDIN-5-YL)PYRIDIN-2-AMINE 1339008-94-4 C9H8N4
3,4-Dibromo-6-(n-propyl)pyridine 3,4-Dibromo-6-(n-propyl)pyridine 1353855-12-5 C8H9Br2N
3-Amino-6-(2-furyl)pyridazine 3-Amino-6-(2-furyl)pyridazine 38530-09-5 C8H7N3O
3-Amino-6-(6-fluoropyridyl-2-yl)pyridazine 3-Amino-6-(6-fluoropyridyl-2-yl)pyridazine 1215073-67-8 C9H7FN4
3-Amino-6-(cyclohexyl)pyridine-4-boronic acid pinacol ester 3-Amino-6-(cyclohexyl)pyridine-4-boronic acid pinacol ester 2223049-67-8 C17H27BN2O2
3-Bromo-1-(cyclopentyl)-1H-pyrrole 3-Bromo-1-(cyclopentyl)-1H-pyrrole 1622840-22-5 C9H12BrN
3-bromo-2-cyclopropyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 3-bromo-2-cyclopropyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 2223049-52-1 C14H19BBrNO2
3-Bromo-2-fluoro-6-(1,4-dioxan-2-yl)pyridine 3-Bromo-2-fluoro-6-(1,4-dioxan-2-yl)pyridine 1622835-05-5 C9H9BrFNO2
3-Bromo-4-cyclobutyl-2-chloropyridine 3-Bromo-4-cyclobutyl-2-chloropyridine 1622839-34-2 C9H9BrClN
3-Bromo-4-cyclopentyl-2-pyridinecarbonitrile 3-Bromo-4-cyclopentyl-2-pyridinecarbonitrile 1622839-37-5 C11H11BrN2
3-Bromo-6-(1H-pyrazol-1-yl)pyridazine 3-Bromo-6-(1H-pyrazol-1-yl)pyridazine 1159821-22-3 C7H5BrN4
3-Bromo-6-(2-furyl)pyridazine 3-Bromo-6-(2-furyl)pyridazine 1086383-84-7 C8H5BrN2O
3-Bromo-6-(3-methyl-1H-pyrazol-1-yl)pyridazine 3-Bromo-6-(3-methyl-1H-pyrazol-1-yl)pyridazine 1159820-81-1 C8H7BrN4
3-Bromo-6-(4-aminophenyl)pyridazine 3-Bromo-6-(4-aminophenyl)pyridazine 1215072-36-8 C10H8BrN3
3-Bromo-6-(cyclopentyl)pyridazine 3-Bromo-6-(cyclopentyl)pyridazine 1086383-78-9 C9H11BrN2
3-Chloro-6-(iso-propenyl)pyridazine 3-Chloro-6-(iso-propenyl)pyridazine 1314356-00-7 C7H7ClN2
4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-4-yl)morpholine-2,2,3,3,5,5,6,6-d8 4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-4-yl)morpholine-2,2,3,3,5,5,6,6-d8 2241874-84-8 C15H15BD8N2O3
4-(3-Fluorophenyl)-1,3,5-triazin-2-amine 4-(3-Fluorophenyl)-1,3,5-triazin-2-amine 1343187-41-6 C9H7FN4
4-(3-Trifluoromethylphenyl)-1,3,5-triazin-2-amine 4-(3-Trifluoromethylphenyl)-1,3,5-triazin-2-amine 1409868-50-3 C10H7F3N4
4-(4-Fluorophenyl)-1,3,5-triazin-2-amine 4-(4-Fluorophenyl)-1,3,5-triazin-2-amine 1341941-49-8 C9H7FN4
4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)morpholine-2,2,3,3,5,5,6,6-d8 4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)morpholine-2,2,3,3,5,5,6,6-d8 2241875-16-9 C15H23BN2O3
4-(sec-Butyl)-1,3,5-triazin-2-amine 4-(sec-Butyl)-1,3,5-triazin-2-amine 1342722-72-8 C7H12N4
4-(tetrahydro-2H-pyran-4-yl)pyrimidin-2-amine 4-(tetrahydro-2H-pyran-4-yl)pyrimidin-2-amine 1398511-14-2 C9H13N3O
4,5-Dibromo-2-cyanopyridine 4,5-Dibromo-2-cyanopyridine 1381935-13-2 C6H2Br2N2
4,6-Dichloro-2-(2-methyl-4-fluorophenyl)pyrimidine 4,6-Dichloro-2-(2-methyl-4-fluorophenyl)pyrimidine 1353854-26-8 C11H7Cl2FN2
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