(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-4-fluoro-2-(hydroxymethyl)tetrahydrofuran-3-ol

Basic Information

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CAS Number

64183-27-3

Molecular Formula

C10H12FN5O3

Molecular Weight

269.24 g/mol

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Ethers

Basic Chemical Raw Materials Organic Chemicals Amines

Basic Chemical Raw Materials Organic Chemicals Heterocyclic Compounds

Pharmaceutical Chemicals Pharmaceutical Intermediates Heterocyclic Intermediates

Fine Chemicals Specialty Chemicals UV Stabilizers

Agricultural Chemicals Pesticides Herbicides

Basic Physical Properties

Physical State

White to Yellow Solid

Boiling Point

628.6°C at 760 mmHg

Water Solubility

Soluble in water.

SMILES

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C1=NC(=C2C(=N1)N(C=N2)C3C(C(C(O3)CO)O)F)N

InChI

InChI=1S/C10H12FN5O3/c11-5-7(18)4(1-17)19-10(5)16-3-15-6-8(12)13-2-14-9(6)16/h2-5,7,10,17-18H,1H2,(H2,12,13,14)/t4-,5-,7-,10-/m1/s1

InChIKey

ZGYYPTJWJBEXBC-QYYRPYCUSA-N

LogP

-1.0028

Topological Polar Surface Area

119.31 Å²

Hydrogen Bond Donor/Acceptor

4 / 8

Complexity

338

Safety Information

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GHS Hazard Pictograms

H302

Hazard Statement

H302 Harmful if swallowed
Acute toxicity, oral

Synonyms & References

English

2-Fluoro-2-deoxyadenosine
(2R,3R,4R,5R)-4-Fluoro-2-hydroxymethyl-5-(6-methylamino-purin-9-yl)-tetrahydro-furan-3-ol
6-Amino-9-(2-deoxy-2-fluoro-beta-D-ribofuranosyl)-9H-purine
2'-Fluoro-2'-deoxyadenosine
C10H12FN5O3
AKOS015900907
BDBM50144932
9-(2-Fluoro-2-deoxy-beta-D-ribofuranosyl)-purin-6-amine
(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-4-fluoro-2-(hydroxymethyl)tetrahydrofuran-3-ol
(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-4-fluoro-2-(hydroxymethyl)oxolan-3-ol
HG1028
A851108
2 inverted exclamation marka-Deoxy-2 inverted exclamation marka-fluoroadenosine
MFCD09750859
CS-0097284
AS-49376
AC-9552
AMY31026
NSC 274941
CHEMBL309579
ZGYYPTJWJBEXBC-QYYRPYCUSA-N
9-(2-Deoxy-2-fluoro-beta-D-ribofuranosyl)adenine
BP-58852
2'-BETA-FLUORO-2',3'-DEOXYADENOSINE
PD158370
2'F-dA
(2R,3R,4R,5R)-5-(6-Amino-9H-purin-9-yl)-4-fluoro-2-(hydroxymethyl)tetrahydrofuran-3-ol
SCHEMBL237404
Adenosine, 2'-deoxy-2'-fluoro-
HY-W039442
2'-Deoxy-2'-fluoroadenosine

MDL Number

MFCD09750859

Customs Code

2934999090

FAQ

What are the physical and chemical properties of (2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-4-fluoro-2-(hydroxymethyl)tetrahydrofuran-3-ol (CAS: 64183-27-3)?

The compound (2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-4-fluoro-2-(hydroxymethyl)tetrahydrofuran-3-ol (CAS: 64183-27-3) has a crystalline form and a molecular weight of approximately 331.2 g/mol. It is poorly soluble in water but soluble in organic solvents. Chemically, it is highly reactive due to the presence of the hydroxymethyl and aminopurin-9-yl groups. It exhibits good reactivity in nucleophilic substitution reactions.

How is (2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-4-fluoro-2-(hydroxymethyl)tetrahydrofuran-3-ol (CAS: 64183-27-3) typically synthesized?

This compound can be synthesized through multistep organic synthesis, involving the protection of the hydroxyl group, coupling with the 9-aminopurine, and subsequent deprotection. Commonly used catalysts include transition metals, and the process often involves high yields and good selectivity.

What industries use (2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-4-fluoro-2-(hydroxymethyl)tetrahydrofuran-3-ol (CAS: 64183-27-3)?

This compound finds application in the pharmaceutical industry, particularly in the development of antiviral and anticancer drugs. It is also used in the polymer industry for its potential in modifying polymer properties, in sensor technology for its reactivity, and in semiconductor manufacturing for its electronic properties.

What precautions should be taken when handling (2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-4-fluoro-2-(hydroxymethyl)tetrahydrofuran-3-ol (CAS: 64183-27-3)?

When handling this compound, it is essential to wear appropriate personal protective equipment (PPE), including gloves, goggles, and a lab coat. Work should be conducted in a well-ventilated area or fume hood. Spills should be cleaned up immediately using absorbent materials and disposed of according to local regulations. Always refer to the Safety Data Sheet (SDS) for detailed handling and emergency procedures.