Azides

Biological systems require working conditions at ambient temperature in aqueous media. “Bioorthogonal” techniques should be preferred, utilizing functional groups usually not present in biological systems. The azide group satisfies these requirements and therefore only minimally perturbs natural biological functions. Since the preparation of phenyl azide by Peter Griess in 1864, this energy-rich and versatile class of compounds has enjoyed considerable interest. Organic azides are used in peptide synthesis, combinatorial synthesis, heterocycle synthesis, and the ligation or modification of biopolymers. Azides are utilized in Huisgen 1,3-dipolar cycloadditions and Click chemistry applications. Recently, the Staudinger ligation, including traceless and nontraceless ligation, has been recognized as a highly chemoselective method for bioconjugates. The azido group can also be regarded as a protecting group for coordinating primary amines, especially in sensitive substrates like complex carbohydrates or peptide nucleic acids (PNA).

Learn More about Azides
Organic Azides and Azide Sources
Azide Building Blocks for Chemical Ligation
Staudinger Ligation

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CBR01707 5-(Trifluoromethyl)-1H-tetrazole hydrate AldrichCPR Aliphatic Azides
C2H3F3N4O
77213 Ethyl azidoacetate solution ~25% in toluene (NMR) Aliphatic Azides
C4H7N3O2
93528 Ethyl azidoacetate solution ~25% in ethanol (NMR) Aliphatic Azides
C4H7N3O2
88539 Ethyl azidoacetate solution ~30% in methylene chloride (NMR) Aliphatic Azides
C4H7N3O2
752320 S-(3-Azidopropyl)thioacetate 95% Aliphatic Azides
C5H9N3OS
712256 5-Azidopentanoic acid ≥97.0% Aliphatic Azides
C5H9N3O2
779083 1-Azido-3-bromobenzene solution ~0.5 M in tert-butyl methyl ether, ≥95.0% (HPLC) Aromatic Azides
C6H4BrN3
779377 1-Azido-4-bromobenzene solution ~0.5 M in tert-butyl methyl ether, ≥95.0% (HPLC) Aromatic Azides
C6H4BrN3
727482 1-Azido-4-chlorobenzene solution ~0.5 M in tert-butyl methyl ether, ≥95.0% (HPLC) Aromatic Azides
C6H4ClN3
779253 1-Azido-4-fluorobenzene solution ~0.5 M in tert-butyl methyl ether, ≥95.0% (HPLC) Aromatic Azides
C6H4FN3
727490 Azidobenzene solution ~0.5 M in tert-butyl methyl ether, ≥95.0% Aromatic Azides
C6H5N3
778583 Azidobenzene solution ~0.5 M in 2-methyltetrahydrofuran, ≥95.0% (HPLC) Green Alternative Aromatic Azides
C6H5N3
359556 4-Azidoaniline hydrochloride 97% Aromatic Azides
C6H6N4 · HCl
513989 1-Azido-1-deoxy-β-D-galactopyranoside 97% Aliphatic Azides
C6H11N3O5
514004 1-Azido-1-deoxy-β-D-glucopyranoside Aliphatic Azides
C6H11N3O5
712795 2-Azido-2-deoxy-D-glucose ≥98.0% (HPLC) Aliphatic Azides
C6H11N3O5
712752 6-Azido-6-deoxy-D-galactose ≥98.0% (HPLC) Aliphatic Azides
C6H11N3O5
712760 6-Azido-6-deoxy-D-glucose ≥95% (HPLC) Aliphatic Azides
C6H11N3O5
CDS010649 8-oxa-3-azabicyclo[3.2.1]octane hydrochloride AldrichCPR Aliphatic Azides
C6H12ClNO
CDS013695 (1S,4S)-2-Methyl-2,5-diaza-bicyclo[2.2.1]heptane dihydrobromide AldrichCPR Aliphatic Azides
C6H14Br2N2
779520 1-Azido-2-(trifluoromethyl)benzene solution ~0.5 M in tert-butyl methyl ether, ≥95.0% (HPLC) Aromatic Azides
C7H4F3N3
779415 1-Azido-3-(trifluoromethyl)benzene solution ~0.5 M in tert-butyl methyl ether, ≥95.0% (HPLC) Aromatic Azides
C7H4F3N3
779199 1-Azido-4-(trifluoromethyl)benzene solution ~0.5 M in tert-butyl methyl ether, ≥95.0% (HPLC) Aromatic Azides
C7H4F3N3
727458 2-Azidobenzoic acid solution ~0.25 M in tert-butyl methyl ether, ≥95.0% (HPLC) Aromatic Azides
C7H5N3O2
CDS011338 3H-Benzotriazole-5-carboxylic acid AldrichCPR Aromatic Azides
C7H5N3O2
778877 4-Azidobenzoic acid solution ~0.2 M in tert-butyl methyl ether, ≥95.0% (HPLC) Aromatic Azides
C7H5N3O2
340138 4-Carboxybenzenesulfonazide 97% Various Azides
C7H5N3O4S
745081 1-(Azidomethyl)-2-chlorobenzene solution ~0.5 M in tert-butyl methyl ether, ≥97.0% (HPLC) Aromatic Azides
C7H6ClN3
745200 1-(Azidomethyl)-2-fluorobenzene solution ~0.5 M in tert-butyl methyl ether, ≥97.0% (HPLC) Aromatic Azides
C7H6FN3
779164 2-Azidotoluene solution ~0.5 M in tert-butyl methyl ether, ≥95.0% (HPLC) Aromatic Azides
C7H7N3
727466 4-Azidotoluene solution ~0.5 M in tert-butyl methyl ether, ≥95.0% (HPLC) Aromatic Azides
C7H7N3
742430 Benzyl azide solution ~0.5 M in dichloromethane, ≥95.0% (HPLC) Aromatic Azides
C7H7N3
779261 2-Azidoanisole solution 0.5 M in tert-butyl methyl ether, ≥95% (HPLC) Aromatic Azides
C7H7N3O
727431 4-Azidoanisole solution ~0.5 M in tert-butyl methyl ether, ≥90.0% (HPLC) Aromatic Azides
C7H7N3O
713589 p-Toluenesulfonyl azide solution 11-15 % (w/w) in toluene, 97% Various Azides
C7H7N3O2S
244546 Azidomethyl phenyl sulfide 95% Various Azides
C7H7N3S
CDS018107 4-azidobenzohydrazide AldrichCPR Aromatic Azides
C7H7N5O
45334 Aziprotryne PESTANAL®, analytical standard Various Azides
C7H11N7S
745316 4-(Azidomethyl)benzonitrile solution ~0.5 M in tert-butyl methyl ether, ≥97.0% (HPLC) Aromatic Azides
C8H6N4
CDS001024 4-(1H-Tetraazol-5-yl)benzaldehyde AldrichCPR Aromatic Azides
C8H6N4O
CDS005480 3-(2H-Tetrazol-5-yl)-benzoic acid AldrichCPR Aromatic Azides
C8H6N4O2
CDS003883 p-Azidoacetophenone AldrichCPR Aromatic Azides
C8H7N3O
779741 Methyl 2-azidobenzoate solution ~0.5 M in tert-butyl methyl ether Aromatic Azides
C8H7N3O2
779644 Methyl 3-azidobenzoate solution ~0.5 M in tert-butyl methyl ether Aromatic Azides
C8H7N3O2
404764 4-Acetamidobenzenesulfonyl azide 97% Various Azides
C8H8N4O3S
744980 1-(Azidomethyl)-2-methylbenzene solution ~0.5 M in tert-butyl methyl ether, ≥97.0% (HPLC) Aromatic Azides
C8H9N3
CDS015331 3-methylbenzylazide AldrichCPR Aromatic Azides
C8H9N3
CDS018827 (1-methyl-1H-1,2,3-benzotriazol-5-yl)methylamine AldrichCPR Aromatic Azides
C8H10N4
690430 (S)-(−)-4-tert-Butyl hydrogen 2-azidosuccinate (dicyclohexylammonium) salt ≥98.0% Aliphatic Azides
C8H13N3O4 · C12H23N
670995 2-Acetamido-2-deoxy-β-D-glucopyranosyl azide ≥98% (HPLC) Aliphatic Azides
C8H14N4O5
17758 11-Azido-3,6,9-trioxaundecan-1-amine technical, ≥90% (GC) Aliphatic Azides
C8H18N4O3
77983 4,4,5,5,6,6,7,7,8,8,9,9,9-Tridecafluorononyl azide ≥97.0% Aliphatic Azides
C9H6F13N3
CDS006821 2-azido-1-benzo[1,3]dioxol-5-yl-ethanone AldrichCPR Aromatic Azides
C9H7N3O3
690767 (S)-2-Azido-3-phenylpropionic acid (dicyclohexylammonium) salt ≥98% Aliphatic Azides
C9H9N3O2 · C12H23N
CDS006820 2-azido-1-(4-methoxy-phenyl)-ethanone AldrichCPR Aromatic Azides
C9H9N3O2
690104 3-(4-Azidophenyl)propionic acid ≥97.0% (T) Aromatic Azides
C9H9N3O2
152854 4-Methoxybenzyloxycarbonyl azide 95% Various Azides
C9H9N3O3
712590 O-(2-Azidoethyl)-O′-methyl-triethylene glycol ≥90% (NMR) Aliphatic Azides
C9H19N3O4
CDS012829 5-(4-Methoxyphenyl)-2H-1,2,3-triazole-4-carbonitrile AldrichCPR Aromatic Azides
C10H8N4O
CDS013703 1-Isopropyl-1H-1,2,3-benzotriazole-5-carboxylic acid AldrichCPR Aromatic Azides
C10H11N3O2
276219 1-Azidoadamantane 97% Aliphatic Azides
C10H15N3
670006 (R)-2-(Azidomethyl)-1-Boc-pyrrolidine ≥95% (HPLC) Aliphatic Azides
C10H18N4O2
669881 (S)-2-(Azidomethyl)-1-Boc-pyrrolidine ≥95% (HPLC) Aliphatic Azides
C10H18N4O2
97087 4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-Heptadecafluoroundecyl azide ≥97.0% Aliphatic Azides
C11H6F17N3
670790 2,3,4-Tri-O-acetyl-β-D-xylopyranosyl azide ≥98.0% (HPLC) Aliphatic Azides
C11H15N3O7
714224 Bis(N-diazo)-tris(O-acetyl)-2-deoxystreptamine ≥97% (HPLC) Aliphatic Azides
C12H16N6O6
514012 1-Azido-1-deoxy-β-D-lactopyranoside 97% Aliphatic Azides
C12H21N3O10
31755 7-(Diethylamino)coumarin-3-carbonyl azide BioReagent, suitable for fluorescence, ≥95% (HPLC) Various Azides
C14H14N4O3
513970 1-Azido-1-deoxy-β-D-galactopyranoside tetraacetate 97% Aliphatic Azides
C14H19N3O9
513997 1-Azido-1-deoxy-β-D-glucopyranoside tetraacetate Aliphatic Azides
C14H19N3O9
G4168 α-D-Mannopyranosyl azide tetraacetate ≥90% (TLC) Aliphatic Azides
C14H19N3O9
76172 O-(2-Aminoethyl)-O′-(2-azidoethyl)pentaethylene glycol ≥90% (oligomer purity) Aliphatic Azides
C14H30N4O6
712817 2,3,4,6-Tetra-O-acetyl-1-azido-1-deoxy-α-D-galactopyranosyl cyanide ≥98.0% (HPLC) Aliphatic Azides
C15H18N4O9
778443 2,4,6-Triisopropylbenzenesulfonyl azide solution 10%±2% in toluene, ≥98% (HPLC) Various Azides
C15H23N3O2S
689440 O-(2-Azidoethyl)heptaethylene glycol ≥95% (oligomer purity) Aliphatic Azides
C16H33N3O8
714151 Fmoc-β-azido-Ala-OH ≥98.0% (HPLC) Aliphatic Azides
C18H16N4O4
76318 O-(2-Aminoethyl)-O′-(2-azidoethyl)heptaethylene glycol ≥90% (oligomer purity) Aliphatic Azides
C18H38N4O8
714291 (S)-5-Azido-2-(Fmoc-amino)pentanoic acid ≥97.0% (HPLC) Aliphatic Azides
C20H20N4O4
71613 O-(2-Azidoethyl)-O-[2-(diglycolyl-amino)ethyl]heptaethylene glycol ≥90% (oligomer purity) Aliphatic Azides
C22H42N4O12
701300 Bis(11-azidoundecyl) disulfide 99% (HPLC) Aliphatic Azides
C22H44N6S2
77787 O-(2-Aminoethyl)-O′-(2-azidoethyl)nonaethylene glycol ≥90% (oligomer purity) Aliphatic Azides
C22H46N4O10
671215 2-Acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl azide ≥98.0% (HPLC) Aromatic Azides
C29H32N4O5
726249 O-(2-Azidoethyl)nonadecaethylene glycol ≥95% (oligomer purity) Aliphatic Azides
C40H81N3O20