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2-Amino-6-chloropurine Riboside

CAS No.
2004-07-1
Chemical Name:
2-Amino-6-chloropurine Riboside
Synonyms
6-Cl-Gr;NSC 44586;2-Amino-6-chL;6-CHLOROADENOSINE;6-CHLOROGUANOSINE;6-Chloroguanosine2;oropurine riboside;Regadenoson Impurity 40;6-CHLOROGUANINE RIBOSIDE;2-NH2-6-Cl-purine-riboside
CBNumber:
CB1755136
Molecular Formula:
C10H12ClN5O4
Molecular Weight:
301.69
MDL Number:
MFCD00005735
MOL File:
2004-07-1.mol
MSDS File:
SDS
Last updated:2026-04-17 13:05:51
Product description Number Pack Size Price
2-Amino-6-chloropurine Riboside >95.0%(HPLC)(T) A2054 1g $45
2-Amino-6-chloropurine Riboside >95.0%(HPLC)(T) A2054 5g $176
2-Amino-6-chloro-9-(b-D-ribofuranosyl)purine A617553 1g $45
2-Amino-6-chloropurine-9-β-D-riboside A603510 500mg $45
2-Amino-6-chloropurine-9-b-D-riboside A1376-58 500mg $319
More product size

2-Amino-6-chloropurine Riboside Properties

Melting point 165-167 °C (dec.)(lit.)
Boiling point 729.9±70.0 °C(Predicted)
Density 1.8359 (rough estimate)
refractive index -38 ° (C=0.1, H2O)
storage temp. Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
solubility DMSO, Methanol
pka 13.05±0.70(Predicted)
form Powder
color White to Off-white
InChIKey TXWHPSZYRUHEGT-ACJOCUEISA-N
CAS DataBase Reference 2004-07-1(CAS DataBase Reference)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H302-H315-H319-H332-H335
Precautionary statements  P261-P280-P305+P351+P338
Hazard Codes  Xi
Risk Statements  36/37/38
Safety Statements  24/25-36-26
WGK Germany  3
Hazard Note  Irritant
HS Code  29349990
NFPA 704
0
1 0

2-Amino-6-chloropurine Riboside price More Price(30)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
TCI Chemical A2054 2-Amino-6-chloropurine Riboside >95.0%(HPLC)(T) 2004-07-1 1g $45 2026-03-19 Buy
TCI Chemical A2054 2-Amino-6-chloropurine Riboside >95.0%(HPLC)(T) 2004-07-1 5g $176 2026-03-19 Buy
TRC A617553 2-Amino-6-chloro-9-(b-D-ribofuranosyl)purine 2004-07-1 1g $45 2021-12-16 Buy
TRC A603510 2-Amino-6-chloropurine-9-β-D-riboside 2004-07-1 500mg $45 2021-12-16 Buy
Usbiological A1376-58 2-Amino-6-chloropurine-9-b-D-riboside 2004-07-1 500mg $319 2021-12-16 Buy
Product number Packaging Price Buy
A2054 1g $45 Buy
A2054 5g $176 Buy
A617553 1g $45 Buy
A603510 500mg $45 Buy
A1376-58 500mg $319 Buy

2-Amino-6-chloropurine Riboside Chemical Properties,Uses,Production

Chemical Properties

Colourless Crystalline Solid

Uses

2-Amino-6-chloropurine riboside (1) is a a novel class of inhibitors of endogenous protein degradation for the preparation of a number of important purine nucleoside derivatives. For example, 6-thioguanosine 2 and 6-selenoguanosine 3 were prepared from a reaction of 1 and the corresponding sodium thiosulfate or potassium selenosulfate.1) 18O-labeled guanosine 4 was incubated from 1 with adenosine deaminase in (18O)-water.2) 2-Amino-6-ethoxypurine riboside 5 and 2-amino-N6-amino-N6-methyladenosine 6 were prepared by treatment of 1 with nucleophiles, sodium ethoxide and methylhydrazine, respectively.3,4) 2-Amino-N6-substituted purine analogues, as typified by 6, were reported as anti-malarial active compounds.
2-Amino-6-chloropurine Riboside Reaction

Synthesis

2',3',5'-Tri-O-acetyl-2-aMino-6-chloropurine Riboside

16321-99-6

2-Amino-6-chloropurine Riboside

2004-07-1

GENERAL STEPS: (2R,3R,4R,5R)-2-(Acetoxymethyl)-5-(2-amino-6-chloro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate (1.56 g, 3.64 mmol) was dissolved in acetone (10 mL), phosphate buffer (58 mL, pH 8) and Novozyme (1.6 g) were added. The reaction mixture was stirred at 60°C for 8 days. After completion of the reaction, the enzyme was removed by filtration and washed with ethanol (50 mL) and acetone (50 mL). The filtrate was concentrated under reduced pressure and the resulting crude product was purified by silica gel column chromatography (eluent: CH2Cl2:MeOH, 85:15) to afford (2R,3R,4S,5R)-2-(2-amino-6-chloro-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol (0.61 g, 55% yield) as a light blue powder.1H NMR ( 400 MHz, DMSO-d6) δ 8.38 (s, 1H, H-8), 6.99 (s, 1H, NH2), 5.81 (d, J = 5.80 Hz, 1H, H-1'), 5.49 (br s, 1H, OH-2'), 5.19 (br s, 1H, OH-3'), 5.05 (t, J = 5.24 Hz, 1H, OH -5'), 4.47 (t, J = 4.85 Hz, 1H, H-2'), 4.20-4.02 (m, 1H, H-3'), 3.90 (q, J = 3.98 Hz, 1H, H-4'), 3.69-3.60 (m, 1H, H2-5'), 3.59-3.52 (m, 1H, H2-5'); 13C NMR (100 MHz, DMSO-d6) δ 160.5, 154.7, 150.2, 141.9, 124.2, 87.4, 86.0, 74.2, 70.9, 61.9; high resolution ES-MS m/z 302.0649 ([M + H]+, C10H1335ClN5O4 calculated value 302.0651).

References

[1] A. JANKOWSKI L. T D Wise. Sodium Thiosulfate and Potassium Selenosulfate as Reagents to Prepare Thio-and Selenopurine Nucleosides[J]. Nucleosides, Nucleotides & Nucleic Acids, 1989, 8 1: 339-348. DOI:10.1080/07328318908054179.
[2] SUNDEEP RAYAT. 5-Cyanoimino-4-oxomethylene-4,5-dihydroimidazole and 5-Cyanoamino-4-imidazolecarboxylic Acid Intermediates in Nitrosative Guanosine Deamination: Evidence from 18O-Labeling Experiments[J]. Journal of the American Chemical Society, 2004, 126 32: 9960-9969. DOI:10.1021/ja049835q.
[3] MORRIS J. ROBINS. Nucleic acid related compounds. 114. Synthesis of 2,6-(disubstituted)purine 2′,3′-dideoxynucleosides and selected cytotoxic, anti-hepatitis b, and adenosine deaminase substrate activities[J]. Journal of Heterocyclic Chemistry, 2009, 38 6: 1297-1306. DOI:10.1002/jhet.5570380609.
[4] KATHLEEN TOO . Anti-malarial activity of N6-modified purine analogues[J]. Bioorganic & Medicinal Chemistry, 2007, 15 16: Pages 5551-5562. DOI:10.1016/j.bmc.2007.05.038.
[5] ALICJA STACHELSKA-WIERZCHOWSKA. Tri-Cyclic Nucleobase Analogs and their Ribosides as Substrates of Purine-Nucleoside Phosphorylases. II Guanine and Isoguanine Derivatives.[J]. Molecules, 2019, 24 8. DOI:10.3390/molecules24081493.
[6] SHIH-HSI CHU Ming Y C Chyng Yann Shiue. Synthesis and cytotoxicity of 6-selenopurine arabinoside and related compounds[J]. Journal of pharmaceutical sciences, 1975, 64 8: 1343-1346. DOI:10.1002/jps.2600640818.

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View Lastest Price from 2-Amino-6-chloropurine Riboside manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
2-Amino-6-chloropurine-9-riboside pictures 2026-04-17 2-Amino-6-chloropurine-9-riboside
2004-07-1
US $0.00-0.00 / Kg/Drum 1KG 98%min 500kg WUHAN FORTUNA CHEMICAL CO., LTD
2-Amino-6-chloropurine-9-riboside pictures 2026-04-17 2-Amino-6-chloropurine-9-riboside
2004-07-1
US $0.00 / G/KG 1G/KG 99% 100000000KG Anhuyan (Hainan) Biotechnology Co., LTD
6-Chloroguanineriboside pictures 2026-04-17 6-Chloroguanineriboside
2004-07-1
US $0.00-0.00 / mg 10g TargetMol Chemicals Inc.
2-AMINO-6-CHLORO-9-(BETA-D-RIBOFURANOSYL)PURINE 2-AMINO-6-CHLOROPURINE-9-BETA-D-RIBOSIDE 2-AMINO-6-CHLOROPURINE-9-RIBOSIDE 2-AMINO-6-CHLOROPURINE RIBOSIDE 6-CHLOROADENOSINE 6-CHLOROGUANINE RIBOSIDE 6-CHLOROGUANOSINE 6-chloro-9-beta-D-ribofuranosyl-9H-purin-2-amine 2-Amino-6-chloro-9H-purine-9-riboside 2-Amino-6-chloropurine-9-b-D-riboside 2-Amino-6-chloro-9-(b-D-ribofuranosyl)purine 6-Chloroguanosine2 2-AMINO-6-CHLOROPURINE RIBOSIDE 97% (HPLC) 2-AMINO-6-CHLOROPURINE RIBOSIDE (6-CHLOROGUANOSINE) 9H-PURIN-2-AMINE, 6-CHLORO-9-.BETA.-D-RIBOFURANOSYL- 2-Amino-6-chloropurine-9--D-riboside 2-NH2-6-Cl-purine-riboside 6-Cl-Gr 9H-Purin-2-amine, 6-chloro-9-β-D-ribofuranosyl- 6-Chloroguanosine≥ 98% (HPLC) (2R,3R,4S,5R)-2-(2-amino-6-chloro-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol 2-Amino-6-chloropurine riboside, 95%, water ≤4.5% 2-Amino-6-chloropurine riboside, 98%, Water ≤1.3% 2-Amino-6-chloropurine-9-ridoside 6-Chloroguanine nucleoside 2-Amino-6-chloropurine-9-riboside,99% (-)-2-Amino-6-chloropurine riboside, 6-Chloroguanine riboside 1β-(2-Amino-6-chloro-9H-purine-9-yl)-1-deoxy-β-D-ribofuranose 2-Amino-6-chloro-9-β-D-ribofuranosyl-9H-purine 6-Chloro-9-(β-D-ribofuranosyl)-9H-purine-2-amine 6-Chloro-9-β-D-ribofuranosyl-9H-purin-2-amine 9-(β-D-Ribofuranosyl)-6-chloro-9H-purine-2-amine 2-Amino-6-chloropurine riboside ,98% 2-AMino-6-chloropurine Ribonucleoside NSC 44586 (2R,3R,4S,5R)-2-(2-aMino-6-chloro-9H-purin-9-yl)-5-(hydroxyMethyl)-tetrahydrofuran-3,4-diol 2-Amino-6-chloro-9-(β-D-ribofuranosyl)purine 2-Amino-6-chloro-9-(beta-D-ribofuranosyl)-9H-purine 2-Amino-6-chloro-9H-purine-9-riboside, 6-Chloro-9-(beta-D-ribofuranosyl)-9H-purin-2-amine, (2R,3R,4S,5R)-2-(2-Amino-6-chloro-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol 2-AMino-6-chloropurine riboside, Water ≤1.3% 6- chlorineguanine nucleotide 2-AMino-6-chloropurine riboside, water ≤4.5% 2-Amino-6-chloropurine Riboside > 2-Amino-6-chL oropurine riboside 2-Amino-6-chloropurine-9-riboside, 6-Chloro-guanosine 2-Amino-6-chloropurine-9-riboside USP/EP/BP 2-Amino-6-chloropurine-9-β-D-riboside 2-Amino-6-chloro purine-9-riboside, 2-Amino-6-chloro-9-(b-D-ribofurano syl)-9H-purine, endogenous protein degradation inhibitor -Amino-6-chloro purine-9-riboside (2R,3S,4R,5R)-2-(2-amino-6-chloro-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol Regadenoson Impurity 40 2-AMINO-6-CHLOROPURINE RIBOSIDE (2A6CIPR) 2004-07-1 2004-7-1 2004-07-01 2004-07-0 2004/7/1