2-chloropyrimidine

• ChemBase ID: 74385
• Molecular Formular: C4H3ClN2
• Molecular Mass: 114.53302
• Monoisotopic Mass: 113.99847579
• SMILES: n1c(nccc1)Cl
• Canonical SMILES: Clc1ncccn1
• InChI: InChI=1S/C4H3ClN2/c5-4-6-2-1-3-7-4/h1-3H
• InChIKey: UNCQVRBWJWWJBF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-chloropyrimidine
• IUPAC Traditional name: pyrimidine, 2-chloro-
• Synonyms: 2-Chloro-1,3-diazine; 2-Chloropyrimidine; 2-Chloropyrimidine; C₂ Ceramide; N-Ethanoyl-D-sphingosine; Acetyl ceramide; N-ACETYL-D-SPHINGOSINE; 2-氯嘧啶

Database IDs

• CAS Number: 3102-57-6; 1722-12-9
• EC Number: 217-020-2
• MDL Number: MFCD00006060
• Beilstein Number: 107171
• PubChem SID: 24851590; 162039304
• PubChem CID: 74404

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.9582857
• LogD (pH = 7.4): 0.9582858
• Log P: 0.9582858
• Molar Refractivity: 28.2209 cm^3
• Polarizability: 10.574802 Å^3
• Polar Surface Area: 25.78 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 62-67°C; 63-66 °C(lit.); 64-67°C
• Boiling Point: 75-76 °C/10 mmHg(lit.); 75-76°C/10mm; 75-76°C/10mm
• Flash Point: 208.4 °F; 98 °C; 98°C; 98°C(208°F)

Safety Information

• Storage Condition: 0°C; -20°C
• Storage Warning: Moisture Sensitive; Toxic/Irritant/Hygroscopic/Store under Argon
• European Hazard Symbols: X; Harmful (Xn)
• UN Number: UN2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: III
• Risk Statements: 22-36; 22-36/37-43
• Safety Statements: 24-26-36/37; 26
• TSCA Listed: 否
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H319; H301-H319-H317-H335
• GHS Precautionary statements: P280H-P262-P305+P351+P338-P309-P310; P301 + P310-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Product Information

• Purity: ~98-99%; 95%; 98%
• Empirical Formula (Hill Notation): C4H3ClN2

DETAILS

MP Biomedicals - 02150656

Crystalline
Purity: ~98-99%
The crystals of this product vary in color from yellow to greenish, but the quality remains consistent, in the 98 to 99% range.

MP Biomedicals - 02158923

Purity: 98%
Inhibitor of cell proliferation and inducer of monocytic differentiation of HL-60 cells. Stimulates cytosolic serine/threonine protein phosphatase in T9 cells at low concentrations.

Sigma Aldrich - 193291

Other Notes
Remainder 2-hydroxypyrimidine
Packaging
10, 50 g in glass bottle

REFERENCES

• Kim, M.-Y., et al., J. Biol. Chem. , 266 : 484, (1991).
• Okazaki, T., et al., ibid. , 265 : 15823, (1990).
• Dobrowsky, R.T. and Hannun, Y.A., et al., J. Biol. Chem. , 267 : 5048, (1992).
• Alkoxylation with 3-butyn-1-ol, followed by intramolecular Diels-Alder reaction, leads to a fused pyridine system, by a sequence analogous to that shown for 2-Chloropyrazine, A10108: Tetrahedron, 45, 803 (1989). For a similar sequence using the anion of an alkynylmalononitrile, see: Tetrahedron, 45, 5151 (1989). For synthesis of a benzofuropyridine by the cyclization of a 2-(alkynylphenoxy)pyrimidine, see: Tetrahedron, 45, 6511 (1989).
• Organolithium reagents add to the 1,6-imine bond, giving, after aromatization with DDQ, 6-substituted 2-chloropyrimidines: J. Org. Chem., 53, 4137 (1988).