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2-Amino-6-chloropurine Riboside

Product Name
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
Formula Weight
301.69
MOL File
2004-07-1.mol
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2-Amino-6-chloropurine Riboside Property

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
form 
Powder
pka
13.05±0.70(Predicted)
color 
White to Off-white
InChIKey
TXWHPSZYRUHEGT-ACJOCUEISA-N
CAS DataBase Reference
2004-07-1(CAS DataBase Reference)
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Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
24/25-36-26
WGK Germany 
3
Hazard Note 
Irritant
HS Code 
29349990
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

TCI Chemical
Product number
A2054
Product name
2-Amino-6-chloropurine Riboside
Purity
>95.0%(HPLC)(T)
Packaging
1g
Price
$45
Updated
2025/07/31
TCI Chemical
Product number
A2054
Product name
2-Amino-6-chloropurine Riboside
Purity
>95.0%(HPLC)(T)
Packaging
5g
Price
$176
Updated
2025/07/31
TRC
Product number
A617553
Product name
2-Amino-6-chloro-9-(b-D-ribofuranosyl)purine
Packaging
1g
Price
$45
Updated
2021/12/16
TRC
Product number
A603510
Product name
2-Amino-6-chloropurine-9-β-D-riboside
Packaging
500mg
Price
$45
Updated
2021/12/16
Usbiological
Product number
A1376-58
Product name
2-Amino-6-chloropurine-9-b-D-riboside
Packaging
500mg
Price
$319
Updated
2021/12/16
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2-Amino-6-chloropurine Riboside Chemical Properties,Usage,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.

Synthesis

16321-99-6

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.

2-Amino-6-chloropurine Riboside Preparation Products And Raw materials

Raw materials

Preparation Products

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2-Amino-6-chloropurine Riboside Suppliers

Americas 1 Belgium 1 Canada 2 China 280 Europe 2 France 1 Germany 4 India 2 Japan 2 Russia 1 Slovakia 1 South Korea 1 Switzerland 2 Ukraine 1 United Kingdom 12 United States 37 Global 350
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View Lastest Price from 2-Amino-6-chloropurine Riboside manufacturers

Moxin Chemicals
Product
Regadenoson Impurity 2004-07-1
Price
US $0.00-0.00/mg
Min. Order
10mg
Purity
99%+ HPLC
Supply Ability
1000
Release date
2025-06-16
WUHAN FORTUNA CHEMICAL CO., LTD
Product
2-Amino-6-chloropurine-9-riboside 2004-07-1
Price
US $0.00-0.00/Kg/Drum
Min. Order
1KG
Purity
98%min
Supply Ability
500kg
Release date
2021-12-09
Hebei Chuanghai Biotechnology Co., Ltd
Product
2-Amino-6-chloropurine-9-riboside 2004-07-1
Price
US $10.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
10 mt
Release date
2024-11-22

2004-07-1, 2-Amino-6-chloropurine RibosideRelated Search:

PUROMYCIN AMINONUCLEOSIDE Adenosine Guanine Guanosine Guanosine 5'-monophosphate disodium salt Glycine 6-Chloroguanine 6-Chloropurine Acyclovir Ribavirin 6-Chloropurine ribonucleoside 3-Aminophenol 6-Aminocaproic acid 6-Thioguanine NUCLEOSIDE PHOSPHORYLASE BACTERIAL 5'-Guanylic acid 6-O-Methyl-guanine Tris(hydroxymethyl)aminomethane

  • 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 &gt
  • 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