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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
714283 (S)-2-Azido-propionic acid cyclohexylammonium salt ≥98% (CE) Aliphatic Azides
C3H5N3O2 · C6H13N
CDS010300 5-Methyl-2H-[1,2,3]triazole-4-carboxylic acid AldrichCPR Aromatic Azides
C4H5N3O2
88539 Ethyl azidoacetate solution ~30% in methylene chloride (NMR) Aliphatic Azides
C4H7N3O2
77213 Ethyl azidoacetate solution ~25% in toluene (NMR) Aliphatic Azides
C4H7N3O2
93528 Ethyl azidoacetate solution ~25% in ethanol (NMR) Aliphatic Azides
C4H7N3O2
752320 S-(3-Azidopropyl)thioacetate 95% Aliphatic Azides
C5H9N3OS
714275 (S)-2-Azido-3-methylbutyric acid cyclohexylammonium salt ≥98% (CE) Aliphatic Azides
C5H9N3O2·C6H13N
712256 5-Azidopentanoic acid ≥97.0% Aliphatic Azides
C5H9N3O2
714267 (S)-2-Azido-4-(methylthio)butanoic acid cyclohexylammonium salt ≥98% (CE) Aliphatic Azides
C5H9N3O2S · C6H13N
CDS015401 (1S,4S)-2-Oxa-5-azabicyclo[2.2.1]heptane hydrochloride AldrichCPR Aliphatic Azides
C5H10ClNO
CDS010433 2-Propyl-2H-1,2,3-triazol-4-amine AldrichCPR Aromatic Azides
C5H10N4
779318 1-Azido-2-bromobenzene solution ~0.5 M in tert-butyl methyl ether Aromatic Azides
C6H4BrN3
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
778958 1-Azido-2-chlorobenzene solution 0.5 M in tert-butyl methyl ether, ≥97% (HPLC) Aromatic Azides
C6H4ClN3
779938 1-Azido-3-chlorobenzene solution 0.5 M in tert-butyl methyl ether, ≥97% (HPLC) Aromatic Azides
C6H4ClN3
727482 1-Azido-4-chlorobenzene solution ~0.5 M in tert-butyl methyl ether, ≥95.0% (HPLC) Aromatic Azides
C6H4ClN3
778842 1-Azido-2-fluorobenzene solution 0.5 M in tert-butyl methyl ether, ≥95% (HPLC) Aromatic Azides
C6H4FN3
779814 1-Azido-3-fluorobenzene solution 0.5 M in tert-butyl methyl ether, ≥95.0% (HPLC) Aromatic Azides
C6H4FN3
779253 1-Azido-4-fluorobenzene solution ~0.5 M in tert-butyl methyl ether, ≥95.0% (HPLC) Aromatic Azides
C6H4FN3
778516 1-Azido-3-iodobenzene solution ~0.5 M in tert-butyl methyl ether, ≥97.0% (HPLC) Aromatic Azides
C6H4IN3
779482 1-Azido-4-iodobenzene solution 0.5 M in tert-butyl methyl ether, ≥95% (HPLC) Aromatic Azides
C6H4IN3
CDS009814 4-azido-2-nitrophenol AldrichCPR Aromatic Azides
C6H4N4O3
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
CDS002784 1H-1,2,3-Benzotriazol-7-ol AldrichCPR Aromatic Azides
C6H5N3O
11545 4-Azidoaniline hydrochloride ≥98.0% (AT) Aromatic Azides
C6H6N4 · HCl
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 ≥98% (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
CDS007177 4-Azido-2,3,5,6-tetrafluorobenzoic acid AldrichCPR Aromatic Azides
C7HF4N3O2
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
11555 4-Azidophenyl isothiocyanate ≥97.0% (CHN) Aromatic Azides
C7H4N4S
359564 4-Azidophenyl isothiocyanate 97% Aromatic Azides
C7H4N4S
778486 Benzoyl azide solution ~0.5 M in tert-butyl methyl ether, ≥95.0% (HPLC) Aromatic Azides
C7H5N3O
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
742457 1-(Azidomethyl)-4-bromobenzene solution ~0.5 M in dichloromethane, ≥96.0% (HPLC) Aromatic Azides
C7H6BrN3
745081 1-(Azidomethyl)-2-chlorobenzene solution ~0.5 M in tert-butyl methyl ether, ≥97.0% (HPLC) Aromatic Azides
C7H6ClN3
742341 1-(Azidomethyl)-4-chlorobenzene solution ~0.5 M in dichloromethane, ≥97.0% (GC) Aromatic Azides
C7H6ClN3
745200 1-(Azidomethyl)-2-fluorobenzene solution ~0.5 M in tert-butyl methyl ether, ≥97.0% (HPLC) Aromatic Azides
C7H6FN3
745308 1-(Azidomethyl)-4-fluorobenzene solution ~0.5 M in dichloromethane, ≥97.0% (HPLC) Aromatic Azides
C7H6FN3
CDS005469 5-(3-hydroxyphenyl) tetrazole AldrichCPR Aromatic Azides
C7H6N4O
779164 2-Azidotoluene solution ~0.5 M in tert-butyl methyl ether, ≥95.0% (HPLC) Aromatic Azides
C7H7N3
778613 3-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
778729 3-Azidoanisole solution 0.5 M in tert-butyl methyl ether, ≥97% (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
CDS003388 4-(3-chlorophenyl)semicarbazide hydrochloride AldrichCPR Aromatic Azides
C7H9Cl2N3O
CDS003397 4-(4-chlorophenyl)semicarbazide hydrochloride AldrichCPR Aromatic Azides
C7H9Cl2N3O
45334 Aziprotryne PESTANAL®, analytical standard Various Azides
C7H11N7S
712779 (S)-2-Azido-3-tert-butoxypropionic acid cyclohexylammonium salt ≥98% (CE) Aliphatic Azides
C7H13N3O3 ·C6H13N
A6057 4-Azidophenacyl bromide powder Aromatic Azides
C8H6BrN3O
CDS006608 2-azido-1-(3-fluoro-phenyl)ethanone AldrichCPR Aromatic Azides
C8H6FN3O
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
CDS005443 4-(2H-Tetrazol-5-yl)-benzoic acid AldrichCPR Aromatic Azides
C8H6N4O2
CDS000249   4-(5-Sulfanyl-1H-tetraazol-1-yl)benzoic acid AldrichCPR Aromatic Azides
C8H6N4O2S
CDS004672 2-(trifluoromethyl)benzoic acid hydrazide AldrichCPR Aromatic Azides
C8H7F3N2O
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
779598 Methyl 4-azidobenzoate solution ~0.5 M in tert-butyl methyl ether, ≥95% (HPLC) Aromatic Azides
C8H7N3O2
CDS008302 2-chloro-4-azidomethylanisole AldrichCPR Aromatic Azides
C8H8ClN3O
404764 4-Acetamidobenzenesulfonyl azide 97% Various Azides
C8H8N4O3S
CDS005784 2-(4-Chlorophenyl)acetohydrazide AldrichCPR Aromatic Azides
C8H9ClN2O
CDS013379 3-chlorophenylacetylhydrazide AldrichCPR Aromatic Azides
C8H9ClN2O
744980 1-(Azidomethyl)-2-methylbenzene solution ~0.5 M in tert-butyl methyl ether, ≥97.0% (HPLC) Aromatic Azides
C8H9N3
742570 1-(Azidomethyl)-4-methylbenzene solution ~0.5 M in tert-butyl methyl ether, ≥95.0% (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
CDS006822 2-azido-1-(4-difluoromethoxy-phenyl)-ethanone AldrichCPR Aromatic Azides
C9H7F2N3O2
CDS011675 2-Phenyl-2H-1,2,3-triazole-4-carboxylic acid AldrichCPR Aromatic Azides
C9H7N3O2
CDS004871 (4-Oxo-1,2,3-benzotriazin-3(4H)-yl)acetic acid AldrichCPR Aromatic Azides
C9H7N3O3
CDS006821 2-azido-1-benzo[1,3]dioxol-5-yl-ethanone AldrichCPR Aromatic Azides
C9H7N3O3
CDS020053 5-[2-Phenylethenyl]-2H-tetraazole AldrichCPR Aliphatic Azides
C9H8N4
CDS006819 2-Azido-1-p-tolyl-ethanone AldrichCPR Aromatic Azides
C9H9N3O
690767 (S)-2-Azido-3-phenylpropionic acid (dicyclohexylammonium) salt ≥98% Aliphatic Azides
C9H9N3O2 · C12H23N
CDS002551 2-(2H-1,2,3-Benzotriazol-2-yl)propanoic acid AldrichCPR Aromatic Azides
C9H9N3O2
CDS006820 2-azido-1-(4-methoxy-phenyl)-ethanone AldrichCPR Aromatic Azides
C9H9N3O2
690104 3-(4-Azidophenyl)propionic acid ≥97.0% (T) Aromatic Azides
C9H9N3O2
CDS008345 3-benzotriazol-1-yl-propionic acid AldrichCPR Aromatic Azides
C9H9N3O2
152854 4-Methoxybenzyloxycarbonyl azide 95% Various Azides
C9H9N3O3
CDS017230 2-Amino-4-(2-methyl-2H-tetraazol-5-yl)benzoic acid AldrichCPR Aromatic Azides
C9H9N5O2
690554 (S)-5-tert-Butyl hydrogen 2-azidoglutarate (dicyclohexylammonium) salt 99% Aliphatic Azides
C9H15N3O4 · C12H23N
712590 O-(2-Azidoethyl)-O′-methyl-triethylene glycol ≥90% (NMR) Aliphatic Azides
C9H19N3O4
CDS012649 Tetrazolo[1,5-a]quinoline-4-carbaldehyde AldrichCPR Aromatic Azides
C10H6N4O
CDS012829 5-(4-Methoxyphenyl)-2H-1,2,3-triazole-4-carbonitrile AldrichCPR Aromatic Azides
C10H8N4O
CDS018988 2-azido-1-methylquinolinium tetrafluoroborate AldrichCPR Aromatic Azides
C10H9BF4N4
CDS011590 3-(4-oxo-1,2,3-benzotriazin-3(4H)-yl)propanoic acid AldrichCPR Aromatic Azides
C10H9N3O3
CDS014306 5-Methyl-2-phenyl-2H-1,2,3-triazole-4-carboxamide AldrichCPR Aromatic Azides
C10H10N4O
CDS013703 1-Isopropyl-1H-1,2,3-benzotriazole-5-carboxylic acid AldrichCPR Aromatic Azides
C10H11N3O2
CDS001900 3-(1H-1,2,3-Benzotriazol-1-yl)butanoic acid AldrichCPR Aromatic Azides
C10H11N3O2
CDS017016 3-benzotriazol-1-yl-2-methyl-propionic 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
CDS018989 2-azido-1-ethylquinolinium tetrafluoroborate AldrichCPR Aromatic Azides
C11H11BF4N4
670790 2,3,4-Tri-O-acetyl-β-D-xylopyranosyl azide ≥98.0% (HPLC) Aliphatic Azides
C11H15N3O7
CDS010943 N-(4-Isopropylbenzyl)-2H-tetrazol-5-amine AldrichCPR Aromatic Azides
C11H15N5
690651 (S)-(−)-2-Azido-6-(Boc-amino)hexanoic acid (dicyclohexylammonium) salt ≥97% Aliphatic Azides
C11H20N4O4 · C12H23N
711152 11-Azido-1-undecanethiol 96% Aliphatic Azides
C11H23SN3
CDS004185 2-Phenyl-2,5,6,7-tetrahydro-4H-1,2,3-benzotriazol-4-one AldrichCPR Aromatic Azides
C12H11N3O
CDS011115 N-(1-Naphthylmethyl)-2H-tetrazol-5-amine AldrichCPR Aromatic Azides
C12H11N5
CDS018938 2-azido-N-phenylacetyl-butyramide AldrichCPR Aromatic Azides
C12H14N4O2
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
CDS013051 N-(3H-2,3,4,5-tetraazolyl)(phenylcyclopentyl)formamide AldrichCPR Aromatic Azides
C13H15N5O
712175 (S)-2-Azido-3-(4-tert-butoxyphenyl)propionic acid cyclohexylammonium salt ≥98% (CE) Aliphatic Azides
C13H17N3O3 · C6H13N
363227 4,4′-Diazido-2,2′-stilbenedisulfonic acid disodium salt hydrate 97% Aromatic Azides
C14H8N6Na2O6S2 · xH2O
33483 4,4′-Diazido-2,2′-stilbenedisulfonic acid disodium salt tetrahydrate ≥99.0% Aromatic Azides
C14H8N6Na2O6S2 · 4H2O
CDS015654 4-(1H-1,2,3-benzotriazol-1-ylmethyl)benzoic acid AldrichCPR Aromatic Azides
C14H11N3O2
CDS012384 N-(1,1′-Biphenyl-4-ylmethyl)-2H-tetrazol-5-amine AldrichCPR Aromatic Azides
C14H13N5
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
712809 2-Azido-D-galactose tetraacetate ≥97% (HPLC) Aliphatic Azides
C14H19N3O9
712787 2-Azido-β-D-glucose tetraacetate ≥98% (HPLC) 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
723045 2,4,6-Triisopropylbenzenesulfonyl azide contains 15 wt. % water as stabilizer, 97% Various Azides
C15H23N3O2S
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
722154 4-Dodecylbenzenesulfonyl azide (soft type) (mixture) Various Azides
C18H29N3O2S
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
712620 N-Boc-4-azido-L-homoalanine (dicyclohexylammonium) salt ≥97% (CE) Aliphatic Azides
C21H39N5O4
712639 N-Boc-5-azido-L-norvaline (dicyclohexylammonium) salt ≥98.0% (CE) Aliphatic Azides
C22H41N5O4
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
712647 N-Boc-6-azido-L-norleucine (dicyclohexylammonium) salt ≥98.0% (CE) Aliphatic Azides
C23H43N5O4
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
671118 2-Acetamido-2-deoxy-β-D-glucopyranosyl azide 3,4,6-triacetate ≥98.0% (HPLC) Various Azides