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About This Item
Empirical Formula (Hill Notation):
C4H3Cl2N3
CAS Number:
Molecular Weight:
163.99
Beilstein:
126885
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.
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Assay
97%
form
liquid
mp
145-148 °C (lit.)
solubility
95% ethanol: soluble 50 mg/mL, clear to slightly hazy, colorless to faintly yellow
functional group
chloro
storage temp.
2-8°C
SMILES string
Nc1c(Cl)ncnc1Cl
InChI
1S/C4H3Cl2N3/c5-3-2(7)4(6)9-1-8-3/h1H,7H2
InChI key
NIGDWBHWHVHOAD-UHFFFAOYSA-N
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Application
5-Amino-4,6-dichloropyrimidine was used in the synthesis of:
- oxepane ring containing monocyclic, conformationally restricted bicyclic and spirocyclic nucleosides[1]
- conformationally locked bicyclo[2.2.1]heptane/oxa-bicyclo[3.2.1]octane nucleosides[2]
- N(7)-substituted purines[3]
- chiral derivatives of (+)-erythro-9-(2-hydroxy-3-nonyl)adenine[4]
- 9-alkyl-6-substituted-purine analogs, potent anticonvulsant agents[5]
- pyrimido-oxazepines in a three-step process with microwave heating at 150°C[6]
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Subhankar Tripathi et al.
The Journal of organic chemistry, 72(19), 7427-7430 (2007-08-25)
Carbohydrate-derived substrates having (i) C-5 nitrone and C-3-O-allyl, (ii) C-4 vinyl and a C-3-O-tethered nitrone, and (iii) C-5 nitrone and C-4-allyloxymethyl generated tetracyclic isoxazolidinooxepane/-pyran ring systems upon intramolecular nitrone cycloaddition reactions. Deprotection of the 1,2-acetonides of these derivatives followed by
J L Kelley et al.
Journal of medicinal chemistry, 31(3), 606-612 (1988-03-01)
Several 9-alkyl-6-substituted-purines were synthesized and tested for anticonvulsant activity against maximal electroshock-induced seizures (MES) in rats. Most compounds were prepared in three steps from 5-amino-4,6-dichloropyrimidine or in two steps via alkylation of 6-chloropurine. Potent anticonvulsant activity against MES resided in
Jinglin Liu et al.
Journal of combinatorial chemistry, 8(3), 410-416 (2006-05-09)
A regiospecific strategy for the preparation of N(7)-substituted purines in an efficient manner was devised. This approach to 6,7,8-trisubstituted purines relies on the cyclization reactions of suitably substituted pyrimidines (1) with either a carboxylic acid or an aldehyde. The method
Sk Sahabuddin et al.
The Journal of organic chemistry, 71(16), 5980-5992 (2006-07-29)
The carbohydrate-derived substrate 3-C-allyl-1,2:5,6-di-O-isopropylidene-alpha-D-allofuranose was judiciously manipulated for preparing suitable synthons, which could be converted to a variety of isoxazolidino-spirocycles and -tricycles through the application of ring-closing metathesis (RCM) and intramolecular nitrone cycloaddition (INC) reactions. Cleavage of the isoxazolidine rings
Tetrahedron Letters, 48, 1489-1489 (2007)
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