Methyl p-toluenesulfonate

Reported in EPA TSCA Inventory.

1. Introduction of Methyl p-toluenesulfonate
Methyl p-toluenesulfonate is also known as Toluene-4-sulfonic acid methyl ester. It belongs to the product categories of Organic Building Blocks; Sulfur Compounds; Tosylates. What's more, its systematic name is methyl 4-methylbenzenesulfonate. Its classification codes are: (1)Agricultural Chemical; (2)Experimental pesticide; (3)Mutation data; (4)Skin / Eye Irritant; (5)Tumor data; (6)Unspecified / Unclassified pesticide. Methyl p-toluenesulfonate should be sealed and stored in a cool place.It is mainly used for the selective methylation reagent in organic synthesis, and is used in the manufacture of dyes.

2. Properties of Methyl p-toluenesulfonate
(1)ACD/LogP: 1.30; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.3; (4)ACD/LogD (pH 7.4): 1.3; (5)ACD/BCF (pH 5.5): 5.71; (6)ACD/BCF (pH 7.4): 5.71; (7)ACD/KOC (pH 5.5): 121.16; (8)ACD/KOC (pH 7.4): 121.16; (9)#H bond acceptors: 3; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 51.75 Å²; (13)Index of Refraction: 1.517; (14)Molar Refractivity: 46.56 cm³; (15)Molar Volume: 153.8 cm³; (16)Polarizability: 18.45×10^-24cm³; (17)Surface Tension: 37.9 dyne/cm; (18)Density: 1.21 g/cm³; (19)Flash Point: 130.3 °C; (20)Enthalpy of Vaporization: 51 kJ/mol; (21)Boiling Point: 291.8 °C at 760 mmHg; (22)Vapour Pressure: 0.00333 mmHg at 25°C.

3. Structure Descriptors of Methyl p-toluenesulfonate
(1)SMILES: O=S(=O)(OC)c1ccc(cc1)C
(2)Std. InChI: InChI=1S/C8H10O3S/c1-7-3-5-8(6-4-7)12(9,10)11-2/h3-6H,1-2H3
(3)Std. InChIKey: VUQUOGPMUUJORT-UHFFFAOYSA-N

4. Toxicity of Methyl p-toluenesulfonate

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
rat	LD50	oral	341mg/kg (341mg/kg)		"Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 1067, 1986.
rat	LD50	subcutaneous	250mg/kg (250mg/kg)		Zeitschrift fuer Krebsforschung. Vol. 74, Pg. 241, 1970.

5. Preparation of Methyl p-toluenesulfonate
Methyl p-toluenesulfonate can be prepared by toluene-4-sulfinic acid and methanol at the ambient temperature. This reaction will need reagents N-chlorosuccinimide, Et₃N and solvent CH₂Cl₂ with the reaction time of 2 hours. The yield is about 62%.

6. Use of Methyl p-toluenesulfonate
Methyl p-toluenesulfonate can be used to produce 1-methyl-4-aminopyridinium toluene-p-sulphonate at the temperature of 150 °C. The reaction time is 20 hours. The yield is about 64%.

7. Other details of Methyl p-toluenesulfonate
When you are using Methyl p-toluenesulfonate, please be cautious about it as the following:
Methyl p-toluenesulfonate is harmful if swallowed. It can cause burns. It is irritating to eyes, respiratory system and skin. It has a limited evidence of a carcinogenic effect and may cause sensitisation by skin contact. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need wear suitable protective clothing, gloves and eye/face protection. When using it, you must avoid contact with skins. In case of accident or if you feel unwell, you must seek medical advice immediately (show the label where possible).