D2253
2,6-Dichloropurine
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About This Item
Empirical Formula (Hill Notation):
C5H2Cl2N4
CAS Number:
Molecular Weight:
189.00
EC Number:
226-681-6
UNSPSC Code:
12352204
PubChem Substance ID:
Beilstein/REAXYS Number:
9354
MDL number:
InChI key
RMFWVOLULURGJI-UHFFFAOYSA-N
InChI
1S/C5H2Cl2N4/c6-3-2-4(9-1-8-2)11-5(7)10-3/h1H,(H,8,9,10,11)
SMILES string
Clc1nc(Cl)c2nc[nH]c2n1
mp
185-195 °C (dec.) (lit.)
storage temp.
−20°C
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signalword
Danger
hcodes
Hazard Classifications
Acute Tox. 3 Oral
Storage Class
6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
Regulatory Information
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Occupational contact sensitization to 2,6-dichloropurine.
R J Rycroft
Contact dermatitis, 7(6), 349-350 (1981-11-01)
M Eugenia García-Rubiño et al.
Acta crystallographica. Section C, Crystal structure communications, 67(Pt 12), o484-o486 (2011-12-06)
Two polymorphs of 2,6-dichloropurine, C(5)H(2)Cl(2)N(4), have been crystallized and identified as the 9H- and 7H-tautomers. Despite differences in the space group and number of symmetry-independent molecules, they exhibit similar hydrogen-bonding motifs. Both crystal structures are stabilized by intermolecular N-H···N interactions
Occupational contact sensitization to 2,6-dichloropurine.
R J Rycroft
Contact dermatitis, 7(3), 162-163 (1981-05-01)
T Maruyama et al.
Nucleosides, nucleotides & nucleic acids, 19(7), 1193-1203 (2000-09-22)
A general procedure to obtain tetra-substituted uric acid by stepwise N-alkylation is described. 2,6-Dichloropurine (1) was condensed with 1-propanol by Mitsunobu reaction to give 9-propyl congener (2). Treatment of 2 with ammonia gave adenine derivative (4a), which was converted to
Michal Hocek et al.
The Journal of organic chemistry, 68(14), 5773-5776 (2003-07-04)
Fe-catalyzed cross-coupling reactions of 9-substituted or protected 2,6-dichloropurines with 1 equiv of methylmagnesium chloride gave regioselectively 2-chloro-6-methylpurines in good yields. The same reactions with 3 equiv of methylmagnesium chloride or Pd-catalyzed reactions with trimethylaluminum afforded 2,6-dimethylpurines. The 2-chloro-6-methylpurines underwent another
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