Azo/Diazo Compounds

Azo compounds are derivatives of diazene (diimide), HN=NH, wherein both hydrogens are substituted by unsaturated hydrocarbon groups, e.g. PhN=NPh azobenzene or diphenyldiazene. Diazo compounds have two linked nitrogen atoms (azo) as a terminal functional group. Sigma-Aldrich offers azo and diazo compounds as alkyl and aryl derivatives. Azo compounds are good oxidizing agents and can be readily reduced back to hydrazine or primary amine. Additionally, azo compounds have been utilized in various biological assays, as coupling agents, and in synthetic dyes. Azo cross-linked polymers have been utilized in specialized drug delivery systems; and prodrugs utilizing azo linkages include sulfasalazine, ipsalazine, balsalazine, and olsalazine. Diazo compounds exhibit high synthetic versatility, spanning organic and inorganic chemistry. Diazomethane, produced using Diazald®, is an extremely versatile reagent for the preparation of both carbon-carbon and carbon-heteroatom bonds. Diazo compounds can be used to couple and immobilize biomolecules onto surfaces.

Learn More about Azo/Diazo Compounds
Raines Phosphine for Conversion of Azides to Diazo Compounds
Microreactor Technology
MRT - Ring Expansion

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Molecular Formula

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A96606 Azodicarboxamide 97% C2H4N4O2
E22201 Ethyl diazoacetate contains ≥13 wt. % dichloromethane C4H6N2O2
752150 Ethyl diazoacetate solution 15% in toluene C4H6N2O2
D8022 3,5-Dichlorophenyldiazonium tetrafluoroborate C6H3Cl2N2 · BF4
280895 4-Bromobenzenediazonium tetrafluoroborate 96% C6H4BBrF4N2
291536 Bis(2,2,2-trichloroethyl) azodicarboxylate ≥97% C6H4Cl6N2O4
395315 Ethyl diazoacetoacetate C6H8N2O3
480754 tert-Butyl diazoacetate C6H10N2O2
752169 tert-Butyl diazoacetate solution 15% in toluene C6H10N2O2
283088 4-Methoxybenzenediazonium tetrafluoroborate 98% C7H7BF4N2O
95642 Diazodimedone ≥98.0% (HPLC) C8H10N2O2
D1928 Fenaminosulf ≥98% C8H10N3NaO3S
D5146 Diazolidinyl urea ≥95% C8H14N4O7
452106 2,2′-Azobis(2-methylpropane) 97% C8H18N2
752177 Benzyl diazoacetate contains ~10% dichloromethane as stabilizer C9H8N2O2
752185 Benzyl diazoacetate solution 10% in toluene C9H8N2O2
776718 3-Diazo-3,4-dihydro-4-oxonaphthalene-1-sulfonyl chloride 97% C10H5ClN2O3S
227285 1-Diazo-2-naphthol-4-sulfonic acid powder C10H6N2O4S
301787 2,2′-Dihydroxyazobenzene 97% C12H10N2O2
11590 4,4′-Azobis(4-cyanovaleric acid) ≥98.0% (T) C12H16N4O4
173452 4-(Phenylazo)benzoyl chloride 97% C13H9ClN2O
479624 4-(Phenylazo)benzoic acid 98% C13H10N2O2
H5126 2-(4-Hydroxyphenylazo)benzoic acid ≥95% (HPLC) C13H10N2O3
64760 4-Methoxyazobenzene ≥98.0% C13H12N2O
CDS000139 Azobenzene-4,4′-dicarbonyl dichloride AldrichCPR C14H8Cl2N2O2
C5272 2-Chloro-4-benzamido-5-methylbenzenediazonium chloride hemi(zinc chloride) salt C14H11Cl2N3O · 0.5Cl2Zn
CDS010533 pigment orange 5 AldrichCPR C16H10N4O5
166804 Dibenzyl azodicarboxylate technical grade, 90% C16H14N2O4
CDS000401 Ponceau SX AldrichCPR C18H14N2Na2O7S2
CDS010534 pontacyl carmine 2b AldrichCPR C19H15N3Na2O9S2