3,5-dichloro-2-hydroxybenzene-1-sulfonyl chloride

• ChemBase ID: 146176
• Molecular Formular: C6H3Cl3O3S
• Molecular Mass: 261.51022
• Monoisotopic Mass: 259.886848
• SMILES: c1c(cc(c(c1S(=O)(=O)Cl)O)Cl)Cl
• Canonical SMILES: Clc1cc(Cl)c(c(c1)S(=O)(=O)Cl)O
• InChI: InChI=1S/C6H3Cl3O3S/c7-3-1-4(8)6(10)5(2-3)13(9,11)12/h1-2,10H
• InChIKey: KXFQRJNVGBIDHA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3,5-dichloro-2-hydroxybenzene-1-sulfonyl chloride
• IUPAC Traditional name: 3,5-dichloro-2-hydroxybenzenesulfonyl chloride
• Synonyms: 2,4-Dichlorophenol-6-sulfonyl chloride; 3,5-Dichloro-2-hydroxybenzenesulfonyl chloride; 2,4-二氯苯酚-6-磺酰氯; 3,5-二氯-2-羟基苯磺酰氯

Database IDs

• CAS Number: 23378-88-3
• EC Number: 245-619-9
• MDL Number: MFCD00007432
• Beilstein Number: 2940993
• PubChem SID: 24848764; 162240375
• PubChem CID: 90078

CALCULATED PROPERTIES

• Acid pKa: 4.628405
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 2.580839
• LogD (pH = 7.4): 1.5648425
• Log P: 3.474073
• Molar Refractivity: 51.8427 cm^3
• Polarizability: 21.050396 Å^3
• Polar Surface Area: 54.37 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 78-80°C; 80-83 °C(lit.)

Safety Information

• Storage Warning: Moisture Sensitive
• European Hazard Symbols: Corrosive (C)
• UN Number: 3261; UN3261
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2; III
• Risk Statements: 34
• Safety Statements: 26-36/37/39-45
• TSCA Listed: 否
• GHS Pictograms: GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H314; H314-H318
• GHS Precautionary statements: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3261 8/PG 2

Product Information

• Purity: 97%; 99%
• Linear Formula: Cl2C6H2(OH)SO2Cl

DETAILS

Sigma Aldrich - 146110

Packaging
25 g in glass bottle

REFERENCES

• Reagent for peptide coupling with low racemization: Tetrahedron Lett., 35, 9561 (1994). See Appendix 6. Reaction is thought to proceed via an o-thioquinone S,S-dioxide, leading to a carboxylic sulfonic mixed anhydride which rearranges to an active ester: