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2-Chloroadenosine

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Name

2-Chloroadenosine

EINECS 205-678-3
CAS No. 146-77-0 Density 2.19 g/cm3
PSA 139.54000 LogP -0.74540
Solubility 10 mg/mL in water Melting Point 162 °C
Formula C10H12ClN5O4 Boiling Point 591.8 °C at 760 mmHg
Molecular Weight 301.689 Flash Point 311.7 °C
Transport Information N/A Appearance white to off-white crystalline solid
Safety 24/25 Risk Codes N/A
Molecular Structure Molecular Structure of 146-77-0 (6-Amino-2-chloropurine riboside) Hazard Symbols N/A
Synonyms

Cl-Ado;6-Amino-2-chloropurine riboside;(2R,3R,4R,5R)-2-(6-amino-2-chloro-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol;4-26-00-03725 (Beilstein Handbook Reference);2-(6-amino-2-chloro-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol;Antibiotic AT 265B;Adenosine,2-chloro-;2-Chloroadenosinehemihydrate;

Article Data 37

2-Chloroadenosine Synthetic route

79999-39-6, 24638-99-1

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

146-77-0

2-Chloroadenosine

Conditions
ConditionsYield
With methanol; sodium methylate for 1h; Reflux;96%
1839-18-5

2-chloroadenine

58-96-8

uridine

146-77-0

2-Chloroadenosine

Conditions
ConditionsYield
With hydrogenchloride; potassium dihydrogenphosphate; potassium hydroxide In water; dimethyl sulfoxide at 58 - 61℃; for 4h; pH=7.1-7.2; Enzymatic reaction;85%
With potassium phosphate; Geobacillus thermoglucosidasius purine nucleoside phosphorylase; Thermus thermophilus pyrimidine nucleoside phosphorylase In water at 70℃; for 1h; pH=7; Enzymatic reaction;
With dipotassium hydrogenphosphate; purine nucleoside phosphorylase; pyrimidine nucleoside phosphorylase; glycine In aq. buffer at 60℃; pH=9; Equilibrium constant; Enzymatic reaction;
3056-18-6

(2R,3R,4R,5R)-4-(acetyloxy)-2-[(acetyloxy)methyl]-5-(2,6-dichloro-9H-purin-9-yl)tetrahydro-3-furanyl acetate

146-77-0

2-Chloroadenosine

Conditions
ConditionsYield
With ethanol; ammonia at 20℃;75%
With ammonia In ethanol at 100℃; for 24h;73%
With ammonium hydroxide In tetrahydrofuran for 72h; Ambient temperature; Yield given;
195727-26-5

2-chloro-2′,3′,5′-tri-O-(t-butyldimethylsilyl)adenosine

146-77-0

2-Chloroadenosine

Conditions
ConditionsYield
With potassium fluoride In methanol at 80℃; for 24h;74%
1839-18-5

2-chloroadenine

146-77-0

2-Chloroadenosine

Conditions
ConditionsYield
With hydrogenchloride; potassium dihydrogenphosphate; potassium hydroxide In water; dimethyl sulfoxide at 58 - 61℃; for 4h; pH=7.1-7.2; Enzymatic reaction;70%
With Trypanosoma brucei purine nucleoside 2'-deoxyribosyltransferase, Y5F mutant In aq. phosphate buffer at 50℃; for 0.5h; pH=6.5; Enzymatic reaction;
1055168-98-3

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

146-77-0

2-Chloroadenosine

Conditions
ConditionsYield
With sodium methylate In methanol at 20℃; for 7h;67%
15465-92-6

2-chloro-6-methoxy-purine riboside

146-77-0

2-Chloroadenosine

Conditions
ConditionsYield
With methanol; ammonia
75802-60-7

2,8-dichloro-adenosine

146-77-0

2-Chloroadenosine

Conditions
ConditionsYield
With sodium hydroxide; Pd-BaSO4 Hydrogenation;
(1R)-tri-O-benzoyl-1-<2,6-dichloro-purin-9-yl>-1,4-anhydro-ribitol

(1R)-tri-O-benzoyl-1-<2,6-dichloro-purin-9-yl>-1,4-anhydro-ribitol

146-77-0

2-Chloroadenosine

Conditions
ConditionsYield
With methanol; ammonia
105499-44-3

2,3,5-tri-O-acetyl-α-D-ribofuranosyl chloride

6-amino-2chloro-purin-9-ylmercury(1+) chloride

6-amino-2chloro-purin-9-ylmercury(1+) chloride

146-77-0

2-Chloroadenosine

Conditions
ConditionsYield
With xylene und Behandeln des Reaktionsprodukts mit methanol.NH3;

2-Chloroadenosine Specification

The 2-Chloroadenosine, with the CAS registry number 146-77-0 and EINECS registry number 205-678-3, has the systematic name of 1,2,3,5-tetra-O-acetyl-β-L-ribofuranose. It is a kind of white to off-white crystalline solid, and belongs to the following product categories: Miscellaneous Biochemicals; 13C & 2H Sugars; Biochemistry; Nucleosides and their analogs; Nucleosides, Nucleotides & Related Reagents; Bases & Related Reagents; Carbohydrates & Derivatives; Heterocycles; Nucleotides; Adenosine receptor; Adenosine. And the molecular formula of the chemical is C10H12ClN5O4. Besides, it is always used as selective A1-adenosine receptor agonist which can induce apoptosis.

The physical properties of 2-Chloroadenosine are as followings: (1)ACD/LogP: -0.46; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): -0.46; (4)ACD/LogD (pH 7.4): -0.46; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 13.4; (8)ACD/KOC (pH 7.4): 13.4; (9)#H bond acceptors: 9; (10)#H bond donors: 5; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 83.76 Å2; (13)Index of Refraction: 1.912; (14)Molar Refractivity: 64.55 cm3; (15)Molar Volume: 137.4 cm3; (16)Polarizability: 25.59×10-24cm3; (17)Surface Tension: 106.5 dyne/cm; (18)Density: 2.19 g/cm3; (19)Flash Point: 311.7 °C; (20)Enthalpy of Vaporization: 92.84 kJ/mol; (21)Boiling Point: 591.8 °C at 760 mmHg; (22)Vapour Pressure: 7.47E-15 mmHg at 25°C. 

You can still convert the following datas into molecular structure:
(1)SMILES: Clc1nc(c2ncn(c2n1)[C@@H]3O[C@@H]([C@@H](O)[C@H]3O)CO)N
(2)InChI: InChI=1/C10H12ClN5O4/c11-10-14-7(12)4-8(15-10)16(2-13-4)9-6(19)5(18)3(1-17)20-9/h2-3,5-6,9,17-19H,1H2,(H2,12,14,15)/t3-,5-,6-,9-/m1/s1
(3)InChIKey: BIXYYZIIJIXVFW-UUOKFMHZBQ

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