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
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
Safety
- WGK Germany
- 3
- RTECS
- AU7357200
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.
N-Bromosuccinimide Price
- Product number
- C3773
- Product name
- 5'-Chloro-5'-deoxyadenosine
- Packaging
- 5G
- Price
- $71
- Updated
- 2025/07/31
- Product number
- C3773
- Product name
- 5'-Chloro-5'-deoxyadenosine
- Packaging
- 25G
- Price
- $213
- Updated
- 2025/07/31
- Product number
- D232545
- Product name
- 5''-Deoxy-5''-chloroadenosine
- Packaging
- 25g
- Price
- $195
- Updated
- 2021/12/16
- Product number
- 295588
- Product name
- 5'-Chloro-5'-deoxyadenosine
- Packaging
- 5g
- Price
- $337
- Updated
- 2021/12/16
- Product number
- D232545
- Product name
- 5''-Deoxy-5''-chloroadenosine
- Packaging
- 100g
- Price
- $610
- Updated
- 2021/12/16
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
5'-CHLORO-5'-DEOXYADENOSINE Suppliers
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View Lastest Price from 5'-CHLORO-5'-DEOXYADENOSINE manufacturers
- 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
- 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
- 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