2-Chloroadenine

HCID 94904

Notes Reactions

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Basic information

CAS: 1839-18-5
Standard SMILES: Nc1nc(Cl)nc2nc[nH]c12
InChIKey: HBJGQJWNMZDFKL-UHFFFAOYSA-N
Molecular formula: C5H4ClN5
Average molar mass: 169.57 g/mol
Monoisotopic mass: 169.01552281

Names & identifiers

Preferred name: 2-Chloroadenine
IUPAC: 2-chloro-7H-purin-6-amine
English name: 2-Chloroadenine
Molecular formula: C5H4ClN5
Molecular weight: 169.57

Names & synonyms

2-Chloroadenine1839-18-52-Chloro-6-aminopurineNSC-7362A05OL9V6OMSQ-22982DTXSID30171515RefChem:470362DTXCID7094006606-011-22-chloro-7H-purin-6-amine2-chloro-9H-purin-6-amine

Show more names

CHLOROADENINENSC 7362oroadenine2-chloropurin2-Chloroadenine 97%2-Chloroadenine >2-Chlorophenthiazine

31458-56-7MFCD00037925Cladribine EP Impurity CAdenine, 2-chloro-1H-Purin-6-amine, 2-chloro-2-chloradenin6-AMINO-2-CHLORO-PURINE6-AMINO-2-CHLORO-7H-PURINE

Database identifiers

CAS: 1839-18-5
PubChem CID: 94904
DTXSID: DTXSID30171515
ChEMBL: CHEMBL134192
UNII: A05OL9V6OM
EC Number: 606-011-2
Nikkaji: J585.322B

Properties

Computed structural properties

XLogP: 0.4
Topological polar surface area: 80.5 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 4
Rotatable bonds: 0
Heavy atoms: 11
Formal charge: 0
Complexity: 154

Experimental & physicochemical properties

LogP0.35

Physicochemical properties

Melting point: 300 °C · >300°C(dec)
Boiling point: 279.76 °C · 279.76°C (rough estimate)
Density: 1.4937 · 1.4937 (rough estimate)
refractive index: 1.611 · 1.6110 (estimate)
storage temp.: -20 °C · -20°C
solubility: Aqueous Base (Slightly), DMSO (Very Slightly, Heated, Sonicated)
form: Solid
pka: 7.17 · 7.17±0.20(Predicted)
color: Pale yellow
Water Solubility: 8.3 mg/L · 8.3mg/L(25 ºC)
λmax: 264 nm · 264nm(lit.)
InChI: InChI=1S/C5H4ClN5/c6-5-10-3(7)2-4(11-5)9-1-8-2/h1H,(H3,7,8,9,10,11)
InChIKey: HBJGQJWNMZDFKL-UHFFFAOYSA-N
SMILES: NC1N=C(N=C2N=CNC2=1)Cl
CAS DataBase Reference: 1839 · 1839-18-5(CAS DataBase Reference)
FDA UNII: 5 OL9V6OM · A05OL9V6OM
UNSPSC Code: 41116107 · 41116107
NACRES: 24 · NA.24
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302
Precautionary statements: 264 · P264-P270-P301+P312+P330-P501
Hazard Codes: Xi,Xn
Risk Statements: 22 · 22
Safety Statements: 24 · 24/25
WGK Germany: 3 · 3
Hazard Note: Irritant
HS Code: 29339900 · 29339900
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 4 Oral · Acute Tox. 4 Oral

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 42 reports by companies from 3 notifications to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (100%)

Safety data

wgk: 3
hs_code: 29339900
risk_code: 22
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi,Xn
hazard_note: Irritant
safety_code: 24/25
Storage Class: 11 - Combustible Solids
Hazard statements: H302
Hazard Classifications: Acute Tox. 4 Oral
Precautionary statements: P264-P270-P301+P312+P330-P501

Chemistry & industry

Applications

Description2-Chloroadenine is a heterocyclic building block that has been used in the synthesis of adenosine antimetabolites with antineoplastic activity. It is also the major catabolite of 2-chloro-2’-deoxyadenosine.

Uses2-Chloroadenine is a compound useful in organic synthesis used in the preparation of 8-oxadenine derivatives.