4-Methylbenzenesulfonhydrazide Chemical Properties

Melting point:

103-108 °C(lit.)

Boiling point:

340.5±35.0 °C(Predicted)

Density 

1.42g/cm3

vapor pressure 

0Pa at 20℃

refractive index 

1.5400 (estimate)

Flash point:

60°C

storage temp. 

Keep in dark place,Inert atmosphere,Store in freezer, under -20°C

solubility 

5g/l

form 

Powder

pka

9.39±0.10(Predicted)

color 

White or off-white to slightly grayish

Water Solubility 

5 g/L (15 ºC)

Sensitive 

Moisture Sensitive

BRN 

610130

Stability:

Light Sensitive

InChIKey

ICGLPKIVTVWCFT-UHFFFAOYSA-N

LogP

0.55 at 25℃

CAS DataBase Reference

1576-35-8(CAS DataBase Reference)

EPA Substance Registry System

Benzenesulfonic acid, 4-methyl-, hydrazide (1576-35-8)

Safety Information

Hazard Codes 

F,Xn

Risk Statements 

11-22-44-2017/11/22

Safety Statements 

16-26

RIDADR 

UN 3226 4.1

WGK Germany 

3

RTECS 

MW0210000

TSCA 

Yes

HazardClass 

4.1

PackingGroup 

II

HS Code 

29280090

MSDS

• Language:English Provider:p-Toluenesulfonhydrazide
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

4-Methylbenzenesulfonhydrazide Usage And Synthesis

Uses

p-Toluenesulfonyl Hydrazide is a reactant that has been used in the synthesis of paspaline.

Chemical Properties

white to off-white powder

Uses

4-Methylbenzenesulfonhydrazide was widely used reagent for the preparation of tosylhydrazones.

Application

p-Toluenesulfonyl hydrazide is used as a reagent for the preparation of tosylhydrazones. It was used to prepare dipyrazolo[1,5-a:4',3'-c]pyridines and 1,2,3-selenadiazole derivatives.

Reactions

4-Methylbenzenesulfonhydrazide as hydrogen donor in reduction reactions:A base-mediated semihydrogenation of ynamides using 4-Methylbenzenesulfonhydrazide (p-toluenesulfonyl hydrazide) as an inexpensive and easy-to-handle hydrogen donor provides the thermodynamically unfavorable Z-enamides exclusively without overhydrogenation and reduction of other functional groups.

Flammability and Explosibility

Not classified

Synthesis

General procedure for the synthesis of p-toluenesulfonyl hydrazide from p-toluenesulfonyl chloride: general method: preparation of p-toluenesulfonyl hydrazide. A mixed solution of water (300 mL) and hydrazine hydrate (12.5 g; 0.25 mol) was cooled to about 5 °C in an ice-water bath. The reaction temperature was kept below 8 °C while a tetrahydrofuran (50 mL) solution of p-toluenesulfonyl chloride (5.54 g, 0.025 mol) was slowly added under stirring. After the addition was completed, the reaction mixture was continued to be stirred at room temperature for 30 min. Subsequently, the tetrahydrofuran was removed by distillation under reduced pressure. The white solid product was isolated by filtration and washed with cold water (3 x 15 mL). Finally, the product was dried in air overnight to give pure p-toluenesulfonyl hydrazide (4.86 g; 89% yield).

Purification Methods

Dissolve the 4-Methylbenzenesulfonhydrazide in hot MeOH (~1g/4mL), filter through Celite and precipitate the material by adding 2-2.5 volumes of distilled H2O. Dry it in air or in a vacuum. [Fiedman et al. Org Synth Coll Vol V 1055 1973, Beilstein 11 II 66.]

References

[1] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 17, p. 4629 - 4636
[2] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 13, p. 3397 - 3407
[3] Archiv der Pharmazie, 2014, vol. 347, # 8, p. 576 - 588
[4] Patent: CN107056871, 2017, A. Location in patent: Paragraph 0022; 0030; 0038
[5] Journal of Molecular Structure, 2017, vol. 1133, p. 80 - 89

4-Methylbenzenesulfonhydrazide(1576-35-8)Related Product Information

• p-Toluenesulfonyl semicarbazide
• Tosylmethyl isocyanide
• Toluenesulfonamide
• p-Anisaldehyde
• 4-Methoxyphenol
• 4-Methylphenylsulfonylurea
• p-Anisidine
• Tosyl azide
• 4-Nitrobenzonitrile
• 4-Methoxybenzyl cyanide
• p-Toluenesulfonamide
• p-Toluidine
• Tosyl chloride
• Maleic hydrazide
• antioxidant 1024
• 1-[1-(Bromomethyl)ethenyl]-2,4-difluoro-benzene
• PHENYL {4-[4-(4-HYDROXYPHENYL)PIPERAZIN-1-YL]PHENYL}CARBAMATE
• 2-[(1S,2S)-1-ethyl-2-bezyloxypropyl]-2,4-dihydro-4-[4-[4-(4-hydroxyphenyl)-1-piperazinyl]phenyl]- 3H-1,2,4-Triazol-3-one