4-methoxybenzene-1-sulfonyl chloride

• ChemBase ID: 86976
• Molecular Formular: C7H7ClO3S
• Molecular Mass: 206.64668
• Monoisotopic Mass: 205.98044276
• SMILES: S(=O)(=O)(c1ccc(cc1)OC)Cl
• Canonical SMILES: COc1ccc(cc1)S(=O)(=O)Cl
• InChI: InChI=1S/C7H7ClO3S/c1-11-6-2-4-7(5-3-6)12(8,9)10/h2-5H,1H3
• InChIKey: DTJVECUKADWGMO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-methoxybenzene-1-sulfonyl chloride
• IUPAC Traditional name: 4-methoxybenzenesulfonyl chloride
• Synonyms: 4-(Chlorosulphonyl)anisole; 4-Methoxybenzenesulphonyl chloride; 4-methoxybenzene-1-sulfonyl chloride; 4-Methoxybenzenesulfonyl chloride; p-Anisolesulfonyl chloride; 4-甲氧基苯磺酰氯

Database IDs

• CAS Number: 98-68-0
• EC Number: 202-692-1
• MDL Number: MFCD00007446
• Beilstein Number: 609005
• PubChem SID: 162074092; 24883568; 24896472
• PubChem CID: 7401

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 1.7618775
• LogD (pH = 7.4): 1.7618775
• Log P: 1.7618775
• Molar Refractivity: 46.7154 cm^3
• Polarizability: 18.958841 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 37-42°C; 39-42 °C; 39-42 °C(lit.); 39-43°C; 41 - 43°C
• Boiling Point: 119-122°C/0.4mm; 119-122°C/0.4mm; 173 °C/14 mmHg(lit.)
• Flash Point: >110°C; >110°C(230°F); 112 °C; 233.6 °F
• Hydrophobicity(logP): 0.089

Safety Information

• Storage Warning: Corrosive/Light Sensitive/Moisture Sensitive/Keep Cold/Store under Argon; Moisture Sensitive
• European Hazard Symbols: Corrosive (C)
• UN Number: 3261; UN3261
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2; II
• 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
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (T); 95%; 97%; 98%; 98+%; 99%
• Grade: purum
• Linear Formula: CH3OC6H4SO2Cl

DETAILS

Sigma Aldrich - M10204

Packaging
5, 25 g in glass bottle

Sigma Aldrich - 64809

Other Notes
Protecting group agent for various nitrogen functions1,2,3

REFERENCES

• Amines and other N-functions can be protected as 4-methoxybenzenesufonyl (PMBS, Mps) derivatives: Chem. Pharm. Bull., 29, 2592 (1981), useful for the imidazole in histidines, stable to TFA and HBr/AcOH: Bull. Chem. Soc. Jpn., 47, 3146 (1974); J. Org. Chem., 45, 547 (1980); deprotection in TFA is promoted by dimethyl sulfide: J. Chem. Soc., Chem. Commun., 955 (1979). For deprotection of PMBS-indoles using Mg in methanol, see: J. Org. Chem., 62, 6519 (1997).
• Also used for protection of the guanidino function of arginine residues in peptide synthesis. The sulfonamide is cleaved by triflic acid under less drastic conditions than tosyl groups: Chem. Pharm. Bull., 24, 1568 (1976). Compare also 4-Methoxy-2,3,6-trimethylbenzenesulfonyl chloride, L11829. See Appendix 6.