• Name

  2-Azidoadenosine

• EINECS
• CAS No. 59587-07-4
• Article Data5
• CAS DataBase
• Density
• Solubility
• Melting Point 170-172 °C
• Formula C₁₀H₁₂N₈O₄
• Boiling Point
• Molecular Weight 308.256
• Flash Point
• Transport Information
• Appearance Off-white to grey solid
• Safety
• Risk Codes
• Molecular Structure
• Hazard Symbols
• Synonyms 2-Azido-D-adenosine;(4S,2R,3R,5R)-2-[6-Amino-2-(diazoazamvinyl)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol;NSC 36905;AC1LABXO;(2R,3R,4S,5R)-2-(6-Amino-2-azidopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol;
• PSA 189.29000
• LogP -1.00424

Synthetic route

174500-37-9

Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(2-azido-6-chloro-purin-9-yl)-tetrahydro-furan-3-yl ester

59587-07-4

2-Azidoadenosine

Conditions

Conditions	Yield
With ammonia In ethanol at 30℃; for 48h;	89%

146-77-0

2-Chloroadenosine

59587-07-4

2-Azidoadenosine

Conditions

Conditions	Yield
Stage #1: 2-Chloroadenosine With hydrazine hydrate at 20℃; for 16h; Stage #2: With acetic acid; sodium nitrite In water for 1h; cooling;	61%
Multi-step reaction with 2 steps 1: H2NNH2*H2O / 20 °C 2: NaNO2; acetic acid / H2O / 0 °C View Scheme

2-hydrazono-adenosine

2-hydrazono-adenosine

59587-07-4

2-Azidoadenosine

Conditions

Conditions	Yield
With acetic acid; sodium nitrite

15763-11-8

2-hydrazinoadenosine

59587-07-4

2-Azidoadenosine

Conditions

Conditions	Yield
With acetic acid; sodium nitrite In water at 0℃;

6974-32-9

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

thioether-bound (4-hydroxypyrimidine-2-yl)-Merrifield resin

thioether-bound (4-hydroxypyrimidine-2-yl)-Merrifield resin

59587-07-4

2-Azidoadenosine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: SnCl4 / acetonitrile / 20 °C 2.1: NH3 / methanol / 20 °C 3.1: hydrazine monohydrate / 16 h / 20 °C 3.2: 61 percent / sodium nitrite; acetic acid / H2O / 1 h / cooling View Scheme

15373-23-6

(2R,3R,4R,5R)-2-((benzoyloxy)methyl)-5-(2,6-dichloro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl dibenzoate

59587-07-4

2-Azidoadenosine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: NH3 / methanol / 20 °C 2.1: hydrazine monohydrate / 16 h / 20 °C 2.2: 61 percent / sodium nitrite; acetic acid / H2O / 1 h / cooling View Scheme

5451-40-1

2,6 dichloropurine

59587-07-4

2-Azidoadenosine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: SnCl4 / acetonitrile / 20 °C 2.1: NH3 / methanol / 20 °C 3.1: hydrazine monohydrate / 16 h / 20 °C 3.2: 61 percent / sodium nitrite; acetic acid / H2O / 1 h / cooling View Scheme

16321-99-6

2-amino-6-chloro-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine

59587-07-4

2-Azidoadenosine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 75 percent / isoamyl nitrite, trimethylsilyl azide / acetonitrile / 1) -20 deg C, 12 h; 2) 0 deg C, 2 d 2: 89 percent / NH3 / ethanol / 48 h / 30 °C View Scheme

118-00-3

G

59587-07-4

2-Azidoadenosine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: pyridine / dimethylformamide 2: POCl, Et4NCl, N,N-dimethylaniline / acetonitrile 3: 75 percent / isoamyl nitrite, trimethylsilyl azide / acetonitrile / 1) -20 deg C, 12 h; 2) 0 deg C, 2 d 4: 89 percent / NH3 / ethanol / 48 h / 30 °C View Scheme

6979-94-8

2',3',5'-tri-O-acetyl-guanosine

59587-07-4

2-Azidoadenosine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: POCl, Et4NCl, N,N-dimethylaniline / acetonitrile 2: 75 percent / isoamyl nitrite, trimethylsilyl azide / acetonitrile / 1) -20 deg C, 12 h; 2) 0 deg C, 2 d 3: 89 percent / NH3 / ethanol / 48 h / 30 °C View Scheme

2-azido-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-9H-purin-6-amine

59587-07-4

2-Azidoadenosine

Conditions

Conditions	Yield
With methanol; ammonia at 50℃; for 15h; Inert atmosphere;

59587-07-4

2-Azidoadenosine

2-azidoadenosine 5'-triphosphate

Conditions

Conditions	Yield
With trimethyl phosphite; tri(n-butyl)ammonium pyrophosphate; trichlorophosphate	58%

59587-07-4

2-Azidoadenosine

C10H13N9O12P3(3-)

Conditions

Conditions	Yield
With trimethyl phosphite; (Bu3NH)4*(PO3)2NH; trichlorophosphate	58%

59587-07-4

2-Azidoadenosine

(2R,3R,4S,5R)-2-(8-Amino-tetrazolo[1,5-a]purin-5-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol

Conditions

Conditions	Yield
In dimethylsulfoxide-d6 at 24.85℃; Equilibrium constant; Thermodynamic data; Further Variations:; Solvents; Temperatures;

59587-07-4

2-Azidoadenosine

77-76-9

2,2-dimethoxy-propane

160150-06-1

2-azido-2',3'-O-isopropylideneadenosine

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In acetone at 20℃; for 16h; Inert atmosphere;	1.57 g

1255942-06-3

(3-(5H,6H-11,12-didehydrodibenzo[b,f]azocin-5-yl)-3-oxopropyl)amine

59587-07-4

2-Azidoadenosine

A

C28H28N10O5

B

C28H28N10O5

Conditions

Conditions	Yield
In methanol at 20℃; for 16h;

...Expand

(1R,8S)-9-hydroxymethyl-bicyclo[6.1.0]nonyne

59587-07-4

2-Azidoadenosine

A

C20H26N8O5

B

C20H26N8O5

Conditions

Conditions	Yield
In water; acetonitrile at 20℃; for 2h; Overall yield = 100 %; Overall yield = 9.3 mg;

...Expand

15715-58-9

triethylamine carbonate

59587-07-4

2-Azidoadenosine

A

2-azidoadenosine monophosphate triethylammonium salt

B

(x)C6H15N*C10H13N8O7P

Conditions

Conditions	Yield
Stage #1: 2-Azidoadenosine With trimethyl phosphite; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; trichlorophosphate In acetonitrile at 0℃; Stage #2: triethylamine carbonate In acetonitrile at 0℃; for 0.5h;	A 60 %Spectr. B 40 %Chromat.

...Expand

15715-58-9

triethylamine carbonate

59587-07-4

2-Azidoadenosine

A

2-azidonicotinamide adenosine diphosphate triethylammonium salt

B

(x)C6H15N*C21H27N10O14P2(1+)

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: trichlorophosphate; trimethyl phosphite; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene / acetonitrile / 0 °C 1.2: 0.5 h / 0 °C 2.1: triethylamine; 1,1'-carbonyldiimidazole / N,N-dimethyl-formamide / 4 h / 20 °C 2.2: 96 h / 20 °C View Scheme

...Expand

2-Azidoadenosine Specification