ChemicalBook > CAS DataBase List > 5'-CHLORO-5'-DEOXYADENOSINE

5'-CHLORO-5'-DEOXYADENOSINE

Product Name: 5'-CHLORO-5'-DEOXYADENOSINE
CAS No.: 892-48-8
Chemical Name: 5'-CHLORO-5'-DEOXYADENOSINE
Synonyms: Ribavirin Impurity 63;5'-Cl-5'-deoxyadenosine;5'-Chloro-5'-deoxyadenosin;5’-chloro-5’-deoxy-adenosin;5'-CHLORO-5'-DEOXYADENOSINE;5'-Deoxy-5'-chloroadenosine;Adenosine,5'-chloro-5'-deoxy-;5'-CHLORO-5'-DEOXY-D-ADENOSINE;5-CHLORO-5-DEOXYADENOSINE HYDRATE;5'-CHLORO-5'-DEOXYADENOSINE USP/EP/BP
CBNumber: CB4706654
Molecular Formula: C10H12ClN5O3
Formula Weight: 285.69
MOL File: 892-48-8.mol

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5'-CHLORO-5'-DEOXYADENOSINE Property

Melting point:: 187 °C (exothermic decomp onset @144.5 C)(lit.)
Boiling point:: 645.6±65.0 °C(Predicted)
Density: 2.03±0.1 g/cm3(Predicted)
storage temp.: Keep in dark place,Sealed in dry,2-8°C
solubility: DMSO (Slightly), Water (Slightly, Heated)
form: Solid
pka: 13.03±0.70(Predicted)
color: Off-White to Light Beige
InChI: InChI=1S/C10H12ClN5O3/c11-1-4-6(17)7(18)10(19-4)16-3-15-5-8(12)13-2-14-9(5)16/h2-4,6-7,10,17-18H,1H2,(H2,12,13,14)/t4-,6-,7-,10-/m1/s1
InChIKey: IYSNPOMTKFZDHZ-KQYNXXCUSA-N
SMILES: C(Cl)[C@H]1O[C@@H](N2C3C(=C(N=CN=3)N)N=C2)[C@H](O)[C@@H]1O

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Safety

WGK Germany: 3
RTECS: AU7357200

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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

H335May cause respiratory irritation

Precautionary statements

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

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: C3773
Product name: 5'-Chloro-5'-deoxyadenosine
Packaging: 5G
Price: $71
Updated: 2025/07/31

TCI Chemical

Product number: C3773
Product name: 5'-Chloro-5'-deoxyadenosine
Packaging: 25G
Price: $213
Updated: 2025/07/31

TRC

Product number: D232545
Product name: 5''-Deoxy-5''-chloroadenosine
Packaging: 25g
Price: $195
Updated: 2021/12/16

Usbiological

Product number: 295588
Product name: 5'-Chloro-5'-deoxyadenosine
Packaging: 5g
Price: $337
Updated: 2021/12/16

TRC

Product number: D232545
Product name: 5''-Deoxy-5''-chloroadenosine
Packaging: 100g
Price: $610
Updated: 2021/12/16

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5'-CHLORO-5'-DEOXYADENOSINE Chemical Properties,Usage,Production

Uses

5''-Deoxy-5''-chloroadenosine is an intermediate in the synthesis of 5''-Deoxy-5''-(methylthio)adenosine (D242600), a substrate to study the specificity and kinetics of 5′-methylthioadenosinephosphorylase (MTAP) (EC2.4.2.28), a tumor suppressor gene expressed enzyme that supports the S-adenosylmethionine (AdoMet) and methionine salvage pathways.

Definition

ChEBI: 5'-chloro-5'-deoxyadenosine is a member of adenosines. It is functionally related to an adenosine.

Synthesis

58-61-7

892-48-8

General steps: 1. Preparation of (2R,3R,4S,5S)-2-(6-amino-9H-purin-9-yl)-5-(chloromethyl) tetrahydrofuran-3,4-diol Under ice bath cooling conditions, (2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol (1 g, 3.47 mmol) was dissolved in acetonitrile (10 ml), pyridine (593 mg, 0.6 ml, 7.49 mmol) and SOCl2 (2.22 g, 1.36 ml, 18.65 mmol). The reaction mixture was stirred at 0-5 °C for 3-4 h, followed by slow warming to room temperature and stirring overnight. After completion of the reaction, the suspension was concentrated in vacuum. Methanol (20 ml), water (2 ml) and NH4OH (4 ml) were added to the concentrate and stirred for 0.5 h at room temperature. The reaction mixture was again concentrated to dryness. The crude product was dissolved in methanol, silica gel (3 g) was added and the solvent was subsequently removed. The residue was purified by silica gel column chromatography (SGC) using gradient elution with ethyl acetate:methanol (0%-10%) to afford the target compound (0.915 g, 86% yield) as a light yellow solid. NMR (500 MHz, MeOD): δ 8.24 (s, 1H), 8.02 (s, 1H), 7.27-7.20 (m, 5H), 6.19 (d, J = 2.0 Hz, 1H), 5.48-5.46 (m, 1H), 5.08-5.06 (m, 1H), 4.43 (t, J = 4.0 Hz, 1H), 3.83 -3.81 (m, 2H), 3.01-2.99 (br s, 2H), 1.60 (s, 3H), 1.38 (s, 3H) ppm. LCMS (m/z): 395.8 [M + H]+.

References

[1] Journal of Medicinal Chemistry, 2012, vol. 55, # 18, p. 8066 - 8074,9
[2] Angewandte Chemie - International Edition, 2016, vol. 55, # 46, p. 14277 - 14280
[3] Angew. Chem., 2016, vol. 128, # 46, p. 14489 - 14492,4
[4] Tetrahedron Letters, 2018, vol. 59, # 4, p. 415 - 417
[5] Patent: US4373097, 1983, A

5'-CHLORO-5'-DEOXYADENOSINE Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from 5'-CHLORO-5'-DEOXYADENOSINE manufacturers

Shenzhen Nexcon Pharmatechs Ltd.

Product: 5'-CHLORO-5'-DEOXYADENOSINE 892-48-8
Price: US $0.00-0.00/G
Min. Order: 1G
Purity: 97%
Supply Ability: 2000
Release date: 2025-05-30

Henan Aochuang Chemical Co.,Ltd.

Product: 5'-Chloro-5'-deoxy-D-adenosine 892-48-8
Price: US $0.00-0.00/kg
Min. Order: 1kg
Purity: 98%
Supply Ability: 1Ton
Release date: 2022-09-29

Zhuozhou Wenxi import and Export Co., Ltd

Product: 5"-CHLORO-5"-DEOXYADENOSINE 892-48-8
Price: US $15.00-10.00/KG
Min. Order: 1KG
Purity: 99%+ HPLC
Supply Ability: Monthly supply of 1 ton
Release date: 2021-07-10

892-48-8, 5'-CHLORO-5'-DEOXYADENOSINERelated Search:

4-Chloro-1-butanol Adenine Sulfate Adenine hydrochloride hemihydrate Adenine hydrochloride (S)-1-Chloro-2-propanol Tetrahydrofurfuryl chloride (S)-(+)-3-Chloro-1,2-propanediol 2-(2-Chloroethoxy)ethanol 1-(2-Chloroethoxy)propane 5-Chloropentanol 3-Chloro-1,2-propanediol 2-CHLORO-2'-DEOXYADENOSINE,CLADRIBINE [2-CHLORO-2''-DEOXYADENOSINE],2-CHLORO-2''-DEOXYADENOSINE (CDA: CLADRIBINE) 5-CHLOROPENTYLAMINE (S)-3-AMINO-1,2-DIHYDROXYPROPANE HYDROCHLORIDE 5'-CHLORO-5'-DEOXYADENOSINE 8-CHLORO-2'-DEOXYADENOSINE 2-chloro-3'-deoxyadenosine 2-CHLORO-2'-DEOXYADENOSINE 5'-TRIPHOSPHATE, TETRALITHIUM SALT

5'-CHLORO-5'-DEOXYADENOSINE

5-CHLORO-5-DEOXYADENOSINE HYDRATE

5'-CHLORO-5'-DEOXYADENOSINE MONOHYDRATE

5’-chloro-5’-deoxy-adenosin

5'-CHLORO-5'-DEOXY-D-ADENOSINE

5'-Deoxy-5'-chloroadenosine

5'-Cl-5'-deoxyadenosine

Adenosine,5'-chloro-5'-deoxy-

9-(5-chloro-5-deoxypentofuranosyl)-9H-purin-6-amine

Ribavirin Impurity 63

5'-CHLORO-5'-DEOXYADENOSINE USP/EP/BP

5'-Chloro-5'-deoxyadenosin

892-48-8

Specialty Synthesis

Oligonucleotide Synthesis

Nucleosides