p-Toluenesulfonamide Property

Melting point:

134-137 °C (lit.)

Boiling point:

221 °C (10 mmHg)

Density 

1.2495 (rough estimate)

vapor density 

5.9 (vs air)

refractive index 

1.6100 (estimate)

Flash point:

202 °C

storage temp. 

Store below +30°C.

solubility 

DMSO: soluble

pka

10.20±0.10(Predicted)

form 

Crystalline Powder

color 

White

Odor

Odorless

Water Solubility 

0.32 g/100 mL (25 º C)

BRN 

472689

LogP

0.820

CAS DataBase Reference

70-55-3(CAS DataBase Reference)

NIST Chemistry Reference

4-Methylbenzenesulfonamide(70-55-3)

EPA Substance Registry System

p-Toluenesulfonamide (70-55-3)

Safety

Hazard Codes 

Xi,Xn

Risk Statements 

36-20/21/22

Safety Statements 

26-36

WGK Germany 

1

RTECS 

XT5075000

TSCA 

Yes

PackingGroup 

III

HS Code 

29350090

Hazardous Substances Data

70-55-3(Hazardous Substances Data)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

p-Toluenesulfonamide Chemical Properties,Usage,Production

Role and purpose

P-toluene sulfonamide is a kind of excellent solid plasticizer used for thermoset plastic. It is suitable for being applied to phenolic resin, melamine resin, urea-formaldehyde resins and polyamide resins. Combination with a small amount can improve workability and make the solidification be uniform, and thus endowing the products with a good gloss. However, P-toluene sulfonamide has no softening effect as the liquid plasticizer, and is incompatible with polyvinyl chloride and vinyl chloride copolymer and is partially compatible with cellulose acetate, cellulose acetate butyrate and cellulose nitrate.
p-Toluene sulfonamide has a low toxicity. It has been approved by the US Food and Drug Administration for being applied into adhesives as food packaging materials.
p-Toluene sulfonamide is briefly called TSH and is commonly used for nickel plating. It can improve the coating structure by the adsorption on the electrode so that it has some degree of surface glossing effect; it is generally not strictly limited for the added amount of brighteners lax; moreover it also has very light effects on the coating characteristics. However, it can only give semi-bright coatings, and the surface gloss is related to the polishing quality of the matrix before plating.
Currently, the brightener agents of nickel plating used is mostly some kinds of organic compounds. And the used amount of these organic compound, although are very little, but with a significant effect. In addition to brightening the coating, it can also largely determine the mechanical properties and chemical properties of the coating. But it must be realized that, since the bright nickel plating solution has been added to the organic brightener, it naturally makes the nickel plating layer contain a relative big amount of organic sulfur and other impurities, thus inevitably enlarging the internal stress, so its mechanical properties is a bitter lower than the conventional nickel-plate, and is prone to crack layer when the plating gets stress; its antirust ability is also worse than the dark nickel. Thus, a single layer of bright nickel is unable to improve the corrosion resistance and mechanical properties of the nickel layer; it must need to form a bi-layer and multilayer nickel or chromium to form a multilayer combination of decorative protective coatings.
When toluene sulfonamide is heated to 105 °C, it will be decomposed and there will be nitrogen released (gas evolution 130 mL/g); p-toluene sulfonamide foaming agents can give a fine foaming with small product shrinkage. It also has a high tear strength and good stability. Thereby, it has a wide range of applications.
The above information is edited by the chemicalbook of Dai xiongfeng.

Uses

1. It is used in the manufacture of dyes, synthetic resins, paints, disinfectants and wood processing brightener.
2. It is used for the manufacture of plasticizers, disinfectants; it can also be used for the production of synthetic resins, paints, and fluorescent dyes.
3. It can be used as primary brightener in the bright nickel plating. It is sued for bright nickel plating for multilayer to obtain uniform bright coating. It has a commonly used amount of 0.2~0.3 g/L.
4. It can be used as plasticizers, also used for synthesis of organics, resins and saccharin.

Production methods

It is obtained by the reaction between toluenesulfonyl chloride and ammonia.
First, add part of HN3 water into the reaction pot, stirring for adding p-toluenesulfonyl chloride with the temperature rising naturally to above 50 °C; after the temperature has dropped, add the remaining ammonia and have reaction for 0.5 h at 85~90 °C. Stop the reaction when the pH reaches 8 to 9. Cool to 20 °C, filter, and wash the filter cake with water to obtain the crude. Then further go through bleaching via activated carbon, alkali dissolution, acid precipitation, rejection filter, drying to get products.

Chemical Properties

White leaflets. Soluble in alcohol; very slightly soluble inwater.Combustible.

Uses

p-Toluenesulfonamide was used to prepare the precursor required for synthesis of ethyl 6-phenyl-1-tosyl-1,2,5,6-tetrahydropyridine-3-carboxylate.

Uses

Used in the manufacture of plasticizer, disinfectant, fungicide, fungicides, wood brightener. Also can be used in the production of synthetic resin, the coating, the fluorescent dye, pharmaceutical, etc.

Uses

4-Tolylsulfonamide is a carbonic anhydrase inhibitor used the synthesis of antiglaucoma and anticancer drugs.

Definition

ChEBI: A sulfonamide that is benzenesulfonamide bearing a methyl group at position 4.

Synthesis Reference(s)

The Journal of Organic Chemistry, 47, p. 4327, 1982 DOI: 10.1021/jo00143a031
Synthetic Communications, 20, p. 293, 1990 DOI: 10.1080/00397919008052297
Synthesis, p. 1031, 1986 DOI: 10.1055/s-1986-31862

General Description

p-Toluenesulfonamide undergoes FeCl₃-catalyzed direct substitution reaction with benzylic and allylic alcohols.It is employed as nucleophile in tetrabutylammonium fluoride (TBAF) catalyzed vinyl aziridine opening reaction.

Purification Methods

Crystallise the amide from hot water, then from EtOH or Et2O/pet ether. [Beilstein 11 H 104, 11 IV 376.]