2-chloro-4,6-dimethoxy-1,3,5-triazine

• ChemBase ID: 68016
• Molecular Formular: C5H6ClN3O2
• Molecular Mass: 175.57304
• Monoisotopic Mass: 175.01485413
• SMILES: n1c(nc(nc1OC)OC)Cl
• Canonical SMILES: COc1nc(OC)nc(n1)Cl
• InChI: InChI=1S/C5H6ClN3O2/c1-10-4-7-3(6)8-5(9-4)11-2/h1-2H3
• InChIKey: GPIQOFWTZXXOOV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-chloro-4,6-dimethoxy-1,3,5-triazine
• IUPAC Traditional name: 2-chloro-4,6-dimethoxy-1,3,5-triazine
• Synonyms: 2-Chloro-4,6-dimethoxy-1,3,5-triazine; 4,6-Dimethoxy-2-chloro-s-triazine; 2,4-Dimethoxy-6-chloro-1,3,5-triazine; NSC 46520; 2-Chloro-4,6-dimethoxy-1,3,5-triazine; 2-氯-4,6-二甲氧基-1,3,5-三嗪

Database IDs

• CAS Number: 3140-73-6
• EC Number: 221-541-0
• MDL Number: MFCD00075607
• Beilstein Number: 148988
• PubChem SID: 24863373; 24854604; 162033748
• PubChem CID: 18450

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 1.8065119
• LogD (pH = 7.4): 1.8065119
• Log P: 1.8065119
• Molar Refractivity: 40.8386 cm^3
• Polarizability: 14.911079 Å^3
• Polar Surface Area: 57.13 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: White Solid
• Melting Point: 71 - 74°C; 71-74 °C(lit.); 75-79 °C; 75-79°C; 78-80°C
• Boiling Point: 99-100°C/1mm
• Hydrophobicity(logP): 1.434

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere
• Storage Warning: IRRITANT
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36/37; 26-37-60
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥98.0% (AT); 95%; 95+%; 97%; 98%
• Grade: purum
• Empirical Formula (Hill Notation): C5H6ClN3O2

DETAILS

Sigma Aldrich - 375217

Packaging
1, 5 g in glass bottle
Application
A stable, yet highly reactive, peptide coupling agent.1

Sigma Aldrich - 24320

Other Notes
Intermediate for the synthesis of triazines. Activating agent for peptide coupling1; Direct reduction of active esters to aldehydes2

REFERENCES

• Similarly, carboxylic acids are converted to Weinreb amides by reaction with N,O-dialkyl hydroxylamines: J. Org. Chem., 66, 2534 (2001).
• Reagent for activation of carboxylic acids to nucleophiles: J. Org. Chem., 63, 4248 (1998). Peptide coupling reagent: Synthesis, 917 (1987). With N-methylmorpholine forms the quaternary chloride (DMTMM) which is a valuable low-cost coupling agent in solid-phase peptide synthesis: Synlett, 275 (2000). For a reexamination of the use of the reagent in peptide coupling, see: Tetrahedron Lett., 42, 4161 (2002); see also Appendix 6.
• Can also be used for the esterification of carboxylic acids: Synthesis, 593 (1999). The intermediate active esters can be hydrogenolyzed, providing a simple method for reduction of acids to aldehydes; at higher pressures, further reduction to the alcohol can be effected: J. Org. Chem., 64, 8962 (1999).