4-methylbenzene-1-sulfonic acid hydrate

• ChemBase ID: 102796
• Molecular Formular: C7H10O4S
• Molecular Mass: 190.2169
• Monoisotopic Mass: 190.0299798
• SMILES: O.Cc1ccc(cc1)S(=O)(=O)O
• Canonical SMILES: Cc1ccc(cc1)S(=O)(=O)O.O
• InChI: InChI=1S/C7H8O3S.H2O/c1-6-2-4-7(5-3-6)11(8,9)10;/h2-5H,1H3,(H,8,9,10);1H2
• InChIKey: KJIFKLIQANRMOU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-methylbenzene-1-sulfonic acid hydrate
• IUPAC Traditional name: toluenesulfonic acid hydrate; hydrate para-toluene sulfonate
• Synonyms: 4-Methylbenzenesulfonic acid monohydrate; p-Toluenesulfonic acid monohydrate, ACS; p-TOLUENE SULFONIC ACID; Toluene Sulfonic Acid; p-TOLUENESULFONIC ACID MONOHYDRATE; p-Toluenesulfonic acid monohydrate; Toluenesulfonic acid mixture of isomers monohydrate; PTSA; Tosic acid monohydrate; 4-Methylbenzenesulfonic acid hydrate; 对甲苯磺酸一水合物, ACS; 对甲苯磺酸 一水合物; 甲基苯磺酸异构体混合物 一水合物; 对甲苯磺酸一水合物

Database IDs

• CAS Number: 6192-52-5; 104-15-4
• EC Number: 203-180-0
• MDL Number: MFCD00142137
• Beilstein Number: 3568023
• Merck Index: 149533
• PubChem SID: 24849965; 162088752; 24900151; 24865132; 24856510; 24846355
• PubChem CID: 521998
• Color Index Number: 42655

CALCULATED PROPERTIES

• Acid pKa: -2.1372879
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -0.7088225
• LogD (pH = 7.4): -0.7088248
• Log P: 1.6675739
• Molar Refractivity: 41.7217 cm^3
• Polarizability: 16.707253 Å^3
• Polar Surface Area: 54.37 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble0.1 g/mL, clear; H2O: soluble1 g/10 mL, clear, colorless
• Apperance: Crystalline; Solid
• Melting Point: 100-104 °C; 102-105 °C; 103-106 °C(lit.); 103-106°C; 103-106°C(anhy); 106-107 °C (anhydrous); 103-106 °C (monohydrate); 38 °C (metastable); 106-107°C; 96-99 °C(lit.)
• Boiling Point: 140°C/20mm; ca. 100 °C at 20 hPa
• Flash Point: 150°C(302°F)
• Auto Ignition Point: 350 °C
• Density: 1.23 - 1.24 g/cm^3 at 20 °C; 1.24
• Vapor Pressure: .1 hPa at 20 °C
• Vapor Density: 5.9 (vs air)

Safety Information

• Storage Condition: Room Temperature (15-30°C), Desiccate
• Storage Warning: Hygroscopic
• RTECS: XT6300000
• European Hazard Symbols: Corrosive (C); Irritant (Xi)
• UN Number: 2585; UN2585
• German water hazard class: 1
• Hazard Class: 8
• Packing Group: 3; III
• Australian Hazchem: 2X
• Risk Statements: 36/37/38; R:36/37/38
• Safety Statements: 26; 26-37; S:26-37
• EU Classification: C4
• EU Hazard Identification Number: 8B
• Emergency Response Guidebook(ERG) Number: 153
• TSCA Listed: 是
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H314-H319-H335; H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P280-P305+P351+P338-P309-P310
• Personal Protective Equipment: dust mask type N95 (US), 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; dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2585 8/PG 3

Product Information

• Purity: ≥85% toluene-4-sulfonic acid basis; ≥98.0% (HPLC); ≥98.0% (T); ≥98.5%; ≥98.5% (T); ≥99% isomers basis (calc. to H2O free subst.); ≥99.0%; ≥99.0% (sum of isomers, TLC); 95+%; 97%; 98%; 98.5%; 98.5+%; 99%
• Grade: ACS reagent; CP; puriss.; purum; reagent grade; ReagentPlus®; SAJ first grade; SAJ special grade
• Ignition Residue: ≤0.1%; ≤0.5%
• Impurities: ≤0.5% H2SO4; 8-12% water; 8-12% water (Karl Fischer); 9.5-11.5% water; 9-11% water
• Cation Traces: Fe: ≤0.01%; heavy metals (as Pb): ≤0.001%; Na: ≤0.002%
• Antion Traces: sulfate (SO42-): ≤0.3%
• Clarity of solution: passes test
• Linear Formula: CH3C6H4SO3H · H2O; CH3C6H5SO3H · H2O

DETAILS

MP Biomedicals - 02103087

Monohydrate
Crystalline
Purity: 99%

Sigma Aldrich - 89760

Other Notes
Lit.1; For a mild hydrolysis of proteins with subsequent quantitative estimation of tryptophan2

Sigma Aldrich - 161993

Packaging
15 kg in fiber drum
500 g in poly bottle
3 kg in poly drum

Sigma Aldrich - 402885

Packaging
100, 500 g in poly bottle
5 g in glass bottle

Sigma Aldrich - T35920

Application
Widely used catalyst
Packaging
100, 500 g in poly bottle
3, 15 kg in poly drum
5 g in glass bottle
Legal Information
ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

REFERENCES

• Esterifications: Org. Synth. Coll., 3, 146, 203, 610 (1955); 9, 722 (1998). Enamine formation: Org. Synth. Coll., 5, 277, 808 (1973); 6, 520 (1988). Protection of alcohols as their THP ethers: Org. Synth. Coll., 7, 334 (1990). Formation acetals: Org. Synth. Coll., 6, 567 (1988); 8, 155 (1993); 9, 251, 717 (1998), and oxazolidines: Org. Synth. Coll., 9, 300 (1998).
• For examples of the numerous applications as an organic-soluble acid catalyst, see:
• Adsorbed on silica gel, has been used for the dehydration of sec- and tert-alcohols to alkenes in good yield: Synthesis, 1159 (1985).
• See also Pyridinium p-toluenesulfonate, A15708.