Standard Article

Diazotization of Amines and Dediazoniation of Diazonium Ions

Amino, Nitroso, Nitro and Related Groups (1996)

  1. Heinrich Zollinger

Published Online: 15 DEC 2009

DOI: 10.1002/9780470682531.pat0083

Patai's Chemistry of Functional Groups

Patai's Chemistry of Functional Groups

How to Cite

Zollinger, H. 2009. Diazotization of Amines and Dediazoniation of Diazonium Ions. Patai's Chemistry of Functional Groups. .

Author Information

  1. Technisch-Chemisches Laboratorium, Eidgenössische Technische Hochschule (ETH), Zürich, Switzerland

Publication History

  1. Published Online: 15 DEC 2009

Featured Compounds

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  1. 1 - 49
Compound 1
Drug synonym:Not Available
Molecular Weight:Not Available
Molecular Formula:(CH2)nC6H8N2
SMILES:NCc1ccc(N)cc1
InChI:1S/C7H10N2/c8-5-6-1-3-7(9)4-2-6/h1-4H,5,8-9H2
InChIKey:BFWYZZPDZZGSLJ-UHFFFAOYSA-N
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Compound 2
Drug synonym:Not Available
Molecular Weight:183.206
Molecular Formula:C12H9NO
SMILES:NC1=CC2=C(C=C1)C1=CC=CC=C1O2
InChI:1S/C12H9NO/c13-8-5-6-10-9-3-1-2-4-11(9)14-12(10)7-8/h1-7H,13H2
InChIKey:GHQCIALFYKYZGS-UHFFFAOYSA-N
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Compound 3
Drug synonym:4‐aminobenzenesulfonic acid, sulfanilic acid
Molecular Weight:173.19
Molecular Formula:C6H7NO3S
SMILES:NC1=CC=C(C=C1)S(O)(=O)=O
InChI:1S/C6H7NO3S/c7-5-1-3-6(4-2-5)11(8,9)10/h1-4H,7H2,(H,8,9,10)
InChIKey:HVBSAKJJOYLTQU-UHFFFAOYSA-N
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Compound 4
Drug synonym:4‐aminobenzenesulfonic acid, sulfanilic acid
Molecular Weight:173.19
Molecular Formula:C6H7NO3S
SMILES:NC1=CC=C(C=C1)S(O)(=O)=O
InChI:1S/C6H7NO3S/c7-5-1-3-6(4-2-5)11(8,9)10/h1-4H,7H2,(H,8,9,10)
InChIKey:HVBSAKJJOYLTQU-UHFFFAOYSA-N
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Compound 5
Drug synonym:Not Available
Molecular Weight:83.0919
Molecular Formula:C3H5N3
SMILES:NC1=CC=NN1
InChI:1S/C3H5N3/c4-3-1-2-5-6-3/h1-2H,(H3,4,5,6)
InChIKey:JVVRJMXHNUAPHW-UHFFFAOYSA-N
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Compound 6
Drug synonym:Not Available
Molecular Weight:Not Available
Molecular Formula:Not Available
SMILES:Not Available
InChI:Not Available
InChIKey:Not Available
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Compound 8
Drug synonym:Not Available
Molecular Weight:177.1667
Molecular Formula:C6H7N7
SMILES:N(\N=N\c1cc[nH]n1)c1cc[nH]n1
InChI:1S/C6H7N7/c1-3-7-9-5(1)11-13-12-6-2-4-8-10-6/h1-4H,(H3,7,8,9,10,11,12)
InChIKey:MGTCKKMKOAYBRE-UHFFFAOYSA-N
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Compound 7
Drug synonym:Not Available
Molecular Weight:94.0748
Molecular Formula:C3H2N4
SMILES:[N-]=[N+]=C1C=CN=N1
InChI:1S/C3H2N4/c4-6-3-1-2-5-7-3/h1-2H
InChIKey:NZNXVABRGBFJED-UHFFFAOYSA-N
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Compound 9
Drug synonym:Not Available
Molecular Weight:Not Available
Molecular Formula:Not Available
SMILES:Not Available
InChI:Not Available
InChIKey:Not Available
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Compound 11
Drug synonym:Not Available
Molecular Weight:Not Available
Molecular Formula:Not Available
SMILES:Not Available
InChI:Not Available
InChIKey:Not Available
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Compound 10
Drug synonym:Not Available
Molecular Weight:Not Available
Molecular Formula:Not Available
SMILES:Not Available
InChI:Not Available
InChIKey:Not Available
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Compound 12
Drug synonym:Not Available
Molecular Weight:320.3905
Molecular Formula:C18H20N6
SMILES:NC1=N[N+](CC1)=C1C=CC(C=C1)=C1C=CC(C=C1)=[N+]1CCC(N)=N1
InChI:1S/C18H19N6/c19-17-9-11-23(21-17)15-5-1-13(2-6-15)14-3-7-16(8-4-14)24-12-10-18(20)22-24/h1-8,19H,9-12H2,(H2,20,22)/q+1/p+1
InChIKey:OVAPKZOFZKXWIK-UHFFFAOYSA-O
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Compound 13
Drug synonym:Not Available
Molecular Weight:Not Available
Molecular Formula:Not Available
SMILES:Not Available
InChI:Not Available
InChIKey:Not Available
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Compound 14
Drug synonym:Not Available
Molecular Weight:99.0946
Molecular Formula:C2H5N5
SMILES:Cn1nnc(N)n1
InChI:1S/C2H5N5/c1-7-5-2(3)4-6-7/h1H3,(H2,3,5)
InChIKey:AZUKLCJYWVMPML-UHFFFAOYSA-N
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Compound 15
Drug synonym:Not Available
Molecular Weight:209.1721
Molecular Formula:C4H7N11
SMILES:Cn1nnc(N\N=N\c2nnn(C)n2)n1
InChI:1S/C4H7N11/c1-14-9-3(7-12-14)5-11-6-4-8-13-15(2)10-4/h1-2H3,(H,5,6,9,10)
InChIKey:LTKJKKNHTVTKFT-UHFFFAOYSA-N
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Compound 17
Drug synonym:Not Available
Molecular Weight:96.0509
Molecular Formula:CN6
SMILES:[N-]=[N+]=C1N=NN=N1
InChI:1S/CN6/c2-3-1-4-6-7-5-1
InChIKey:CCIGNVHJZFBDPI-UHFFFAOYSA-N
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Compound 16
Drug synonym:Not Available
Molecular Weight:132.512
Molecular Formula:CHClN6
SMILES:[Cl-].N#[N+]C1=NN=NN1
InChI:1S/CHN6.ClH/c2-3-1-4-6-7-5-1;/h(H,4,5,6,7);1H/q+1;/p-1
InChIKey:PARRMKRTMHYKDB-UHFFFAOYSA-M
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Compound 18
Drug synonym:Not Available
Molecular Weight:108.1411
Molecular Formula:C6H8N2
SMILES:NC1=C(N)C=CC=C1
InChI:1S/C6H8N2/c7-5-3-1-2-4-6(5)8/h1-4H,7-8H2
InChIKey:GEYOCULIXLDCMW-UHFFFAOYSA-N
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Compound 19
Drug synonym:Not Available
Molecular Weight:120.1314
Molecular Formula:C6H6N3
SMILES:Nc1ccccc1[N+]#N
InChI:1S/C6H6N3/c7-5-3-1-2-4-6(5)9-8/h1-4H,7H2/q+1
InChIKey:NXCOSEIUCIOFNB-UHFFFAOYSA-N
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Compound 20
Drug synonym:Not Available
Molecular Weight:119.124
Molecular Formula:C6H5N3
SMILES:N1N=NC2=CC=CC=C12
InChI:1S/C6H5N3/c1-2-4-6-5(3-1)7-9-8-6/h1-4H,(H,7,8,9)
InChIKey:QRUDEWIWKLJBPS-UHFFFAOYSA-N
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Compound 21
Drug synonym:Not Available
Molecular Weight:132.1217
Molecular Formula:C6H4N4
SMILES:N#[N+]c1ccccc1[N+]#N
InChI:1S/C6H4N4/c7-9-5-3-1-2-4-6(5)10-8/h1-4H/q+2
InChIKey:FKOLVOYBZCYQQJ-UHFFFAOYSA-N
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Compound 22
Drug synonym:Not Available
Molecular Weight:176.238
Molecular Formula:C9H8N2S
SMILES:Nc1cc(sn1)-c1ccccc1
InChI:1S/C9H8N2S/c10-9-6-8(12-11-9)7-4-2-1-3-5-7/h1-6H,(H2,10,11)
InChIKey:VLQBYPSKWKIMPS-UHFFFAOYSA-N
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Compound 23b
Drug synonym:Not Available
Molecular Weight:120.1088
Molecular Formula:C6H4N2O
SMILES:[O-]c1ccc(cc1)[N+]#N
InChI:1S/C6H4N2O/c7-8-5-1-3-6(9)4-2-5/h1-4H
InChIKey:WTQZSMDDRMKJRI-UHFFFAOYSA-N
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Compound 23a
Drug synonym:Not Available
Molecular Weight:120.1088
Molecular Formula:C6H4N2O
SMILES:[N-]=[N+]=C1C=CC(=O)C=C1
InChI:1S/C6H4N2O/c7-8-5-1-3-6(9)4-2-5/h1-4H
InChIKey:WTQZSMDDRMKJRI-UHFFFAOYSA-N
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Compound 24
Drug synonym:Not Available
Molecular Weight:292.206
Molecular Formula:C14H4N4O4
SMILES:[N-]=[N+]=c1ccc(=O)c2c1c(=O)c1c(c(ccc1=O)=[N+]=[N-])c2=O
InChI:1S/C14H4N4O4/c15-17-5-1-3-7(19)11-9(5)13(21)12-8(20)4-2-6(18-16)10(12)14(11)22/h1-4H
InChIKey:YOCJPYGUCNLPTQ-UHFFFAOYSA-N
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Compound 25
Drug synonym:Not Available
Molecular Weight:195.22
Molecular Formula:C12H9N3
SMILES:NC1=CC=CC2=NC3=CC=CC=C3N=C12
InChI:1S/C12H9N3/c13-8-4-3-7-11-12(8)15-10-6-2-1-5-9(10)14-11/h1-7H,13H2
InChIKey:QWUFXJHVFNRNCU-UHFFFAOYSA-N
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Compound 26
Drug synonym:Not Available
Molecular Weight:222.2022
Molecular Formula:C12H6N4O
SMILES:[N-]=[N+]=C1C(=O)C=CC2=NC3=CC=CC=C3N=C12
InChI:1S/C12H6N4O/c13-16-12-10(17)6-5-9-11(12)15-8-4-2-1-3-7(8)14-9/h1-6H
InChIKey:PNDCJNGNAFSTFE-UHFFFAOYSA-N
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Compound 27
Drug synonym:Not Available
Molecular Weight:164.1613
Molecular Formula:C8H8N2O2
SMILES:CC(=O)O\N=N\c1ccccc1
InChI:1S/C8H8N2O2/c1-7(11)12-10-9-8-5-3-2-4-6-8/h2-6H,1H3/b10-9+
InChIKey:DSAGFZCHZBGVKD-MDZDMXLPSA-N
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Compound 28
Drug synonym:Not Available
Molecular Weight:164.1613
Molecular Formula:C8H8N2O2
SMILES:CC([O-])=O.N#[N+]c1ccccc1
InChI:1S/C6H5N2.C2H4O2/c7-8-6-4-2-1-3-5-6;1-2(3)4/h1-5H;1H3,(H,3,4)/q+1;/p-1
InChIKey:BKTLDKMUWKCASK-UHFFFAOYSA-M
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Compound 30
Drug synonym:Not Available
Molecular Weight:Not Available
Molecular Formula:Not Available
SMILES:Not Available
InChI:Not Available
InChIKey:Not Available
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Compound 31
Drug synonym:Not Available
Molecular Weight:Not Available
Molecular Formula:Not Available
SMILES:Not Available
InChI:Not Available
InChIKey:Not Available
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Compound 32
Drug synonym:Not Available
Molecular Weight:101.13
Molecular Formula:C2H3N3S
SMILES:Nc1ncns1
InChI:1S/C2H3N3S/c3-2-4-1-5-6-2/h1H,(H2,3,4,5)
InChIKey:VJHTZTZXOKVQRN-UHFFFAOYSA-N
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Compound 33
Drug synonym:Not Available
Molecular Weight:130.128
Molecular Formula:C2H2N4OS
SMILES:O=NNc1ncns1
InChI:1S/C2H2N4OS/c7-6-5-2-3-1-4-8-2/h1H,(H,3,4,5,7)
InChIKey:LTFKRBODNIBJLL-UHFFFAOYSA-N
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Compound 34
Drug synonym:Not Available
Molecular Weight:113.121
Molecular Formula:C2HN4S
SMILES:N#[N+]c1ncns1
InChI:1S/C2HN4S/c3-6-2-4-1-5-7-2/h1H/q+1
InChIKey:VJUPOEBMLHXOPI-UHFFFAOYSA-N
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Compound 38
Drug synonym:Not Available
Molecular Weight:Not Available
Molecular Formula:Not Available
SMILES:Not Available
InChI:Not Available
InChIKey:Not Available
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Compound 39
Drug synonym:Not Available
Molecular Weight:Not Available
Molecular Formula:Not Available
SMILES:Not Available
InChI:Not Available
InChIKey:Not Available
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Compound 40
Drug synonym:Not Available
Molecular Weight:Not Available
Molecular Formula:Not Available
SMILES:Not Available
InChI:Not Available
InChIKey:Not Available
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Compound 41
Drug synonym:Not Available
Molecular Weight:Not Available
Molecular Formula:Not Available
SMILES:Not Available
InChI:Not Available
InChIKey:Not Available
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Compound 42
Drug synonym:Not Available
Molecular Weight:575
Molecular Formula:C34H28O2Pd
SMILES:[Pd].O=C(\C=C\C1=CC=CC=C1)/C=C/C1=CC=CC=C1.O=C(\C=C\C1=CC=CC=C1)/C=C/C1=CC=CC=C1
InChI:1S/2C17H14O.Pd/c2*18-17(13-11-15-7-3-1-4-8-15)14-12-16-9-5-2-6-10-16;/h2*1-14H;/b2*13-11+,14-12+;
InChIKey:UKSZBOKPHAQOMP-SVLSSHOZSA-N
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Compound 43
Drug synonym:Not Available
Molecular Weight:Not Available
Molecular Formula:Not Available
SMILES:Not Available
InChI:Not Available
InChIKey:Not Available
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Compound 44
Drug synonym:Not Available
Molecular Weight:Not Available
Molecular Formula:Not Available
SMILES:Not Available
InChI:Not Available
InChIKey:Not Available
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Compound 45
Drug synonym:Not Available
Molecular Weight:Not Available
Molecular Formula:Not Available
SMILES:Not Available
InChI:Not Available
InChIKey:Not Available
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Compound 46
Drug synonym:Not Available
Molecular Weight:Not Available
Molecular Formula:Not Available
SMILES:Not Available
InChI:Not Available
InChIKey:Not Available
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Compound 47
Drug synonym:Not Available
Molecular Weight:318.191
Molecular Formula:C19H18FeO
SMILES:[Fe++].c1cc[cH-]c1.[CH]1[CH]C=C(CC2COc3ccccc23)[CH-]1
InChI:1S/C14H15O.C5H5.Fe/c1-2-6-11(5-1)9-12-10-15-14-8-4-3-7-13(12)14;1-2-4-5-3-1;/h3-8,12H,1-2,9-10H2;1-5H;/q2*-1;+2
InChIKey:SPJYOMBBGHSDTL-UHFFFAOYSA-N
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Compound 49
Drug synonym:Not Available
Molecular Weight:142.154
Molecular Formula:C10H6O
SMILES:Not Available
InChI:1S/C10H8O/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-6H,7H2
InChIKey:RZPFVRFSYMUDJO-UHFFFAOYSA-N
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Compound 50
Drug synonym:Not Available
Molecular Weight:142.154
Molecular Formula:C10H6O
SMILES:O=C=C1C=Cc2ccccc12
InChI:1S/C10H6O/c11-7-9-6-5-8-3-1-2-4-10(8)9/h1-6H
InChIKey:DGTQIUUXHSIFQS-UHFFFAOYSA-N
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Compound 51
Drug synonym:Not Available
Molecular Weight:160.1693
Molecular Formula:C10H8O2
SMILES:OC(=O)C1=CCC2=CC=CC=C12
InChI:1S/C10H8O2/c11-10(12)9-6-5-7-3-1-2-4-8(7)9/h1-4,6H,5H2,(H,11,12)
InChIKey:NZSCUDBGUBVDLO-UHFFFAOYSA-N
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Compound 48a
Drug synonym:Not Available
Molecular Weight:170.1674
Molecular Formula:C10H6N2O
SMILES:[O-]c1c(ccc2ccccc12)[N+]#N
InChI:1S/C10H6N2O/c11-12-9-6-5-7-3-1-2-4-8(7)10(9)13/h1-6H
InChIKey:URQUNWYOBNUYJQ-UHFFFAOYSA-N
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Compound 48b
Drug synonym:Not Available
Molecular Weight:170.1674
Molecular Formula:C10H6N2O
SMILES:[N-]=[N+]=C1C=Cc2ccccc2C1=O
InChI:1S/C10H6N2O/c11-12-9-6-5-7-3-1-2-4-8(7)10(9)13/h1-6H
InChIKey:URQUNWYOBNUYJQ-UHFFFAOYSA-N
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