Ethyl p-toluenesulfonate

Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

The Benzenesulfonic acid,4-methyl-, ethyl ester, with the CAS registry number 80-40-0, is also known as p-Toluenesulfonic acid, ethyl ester. It belongs to the product categories of Sulphur Derivatives; Organic Building Blocks; Sulfur Compounds; Tosylates. Its EINECS number is 201-276-7. This chemical's molecular formula is C₉H₁₂O₃S and molecular weight is 200.25. What's more, its systematic name is ethyl 4-methylbenzenesulfonate. Its classification codes are: (1)Mutation data; (2)Tumor data. It should be sealed and stored in a cool place. It is a plasticizer for cellulose acetate, and also used as ethylating agent. It is also used as intermediates in manufacturering sensitive materials.

Physical properties of Benzenesulfonic acid,4-methyl-, ethyl ester are: (1)ACD/LogP: 1.83; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.83; (4)ACD/LogD (pH 7.4): 1.83; (5)ACD/BCF (pH 5.5): 14.48; (6)ACD/BCF (pH 7.4): 14.48; (7)ACD/KOC (pH 5.5): 235.72; (8)ACD/KOC (pH 7.4): 235.72; (9)#H bond acceptors: 3; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 51.75 Å²; (13)Index of Refraction: 1.512; (14)Molar Refractivity: 51.19 cm³; (15)Molar Volume: 170.3 cm³; (16)Polarizability: 20.29×10^-24cm³; (17)Surface Tension: 37.6 dyne/cm; (18)Density: 1.175 g/cm³; (19)Flash Point: 157.8 °C; (20)Enthalpy of Vaporization: 52.49 kJ/mol; (21)Boiling Point: 306.2 °C at 760 mmHg; (22)Vapour Pressure: 0.00142 mmHg at 25°C.

Preparation: this chemical can be prepared by 2,2-dimethyl-propionic acid ethyl ester and toluene 4-sulfonic acid monohydrate by heating. This reaction will need solvent toluene with the reaction time of 24 hours. The yield is about 51%.

Uses of Benzenesulfonic acid,4-methyl-, ethyl ester: it can be used to produce 2-pyridin-4-yl-butyronitrile at the ambient temperature. It will need reagent NaH and solvents dimethylsulfoxide, toluene with the reaction time of 15 hours. The yield is about 43.7%.

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. It has a limited evidence of a carcinogenic effect. It is harmful if swallowed. 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. In case of accident or if you feel unwell, you must seek medical advice immediately (show the label where possible).

You can still convert the following datas into molecular structure:
(1)SMILES: O=S(=O)(OCC)c1ccc(cc1)C
(2)Std. InChI: InChI=1S/C9H12O3S/c1-3-12-13(10,11)9-6-4-8(2)5-7-9/h4-7H,3H2,1-2H3
(3)Std. InChIKey: VRZVPALEJCLXPR-UHFFFAOYSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intraperitoneal	1gm/kg (1000mg/kg)		JNCI, Journal of the National Cancer Institute. Vol. 62, Pg. 911, 1979.
rat	LD50	subcutaneous	500mg/kg (500mg/kg)		Zeitschrift fuer Krebsforschung. Vol. 74, Pg. 241, 1970.