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4-Methylbenzenesulfonhydrazide

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CAS:1576-35-8
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Products Intro: Product Name:4-Methylbenzenesulfonhydrazide
CAS:1576-35-8
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CAS:1576-35-8
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CAS:1576-35-8
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  • CAS:1576-35-8
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4-Methylbenzenesulfonhydrazide Basic information
Uses
Product Name:4-Methylbenzenesulfonhydrazide
Synonyms:n-toluolsulphonylhydrazine;p-toluenesulfohydrazide;p-tolylsulfonyl-hydrazin;4-METHYL-1-BENZENESULFONYL HYDRAZIDE;P-Benzene Sulfonyl Hydrazine;p-Toluenesulfonic acid hydrazide, p-Toluenesulfonyl hydrazide, Tosylhydrazide;Foamer TSH;p-Toluenesulfonhydrazide, p-Toluenesulfonic acid hydrazide, p-Toluenesulfonyl hydrazide, Tosylhydrazide
CAS:1576-35-8
MF:C7H10N2O2S
MW:186.23
EINECS:216-407-3
Product Categories:Building Blocks;Chemical Synthesis;Organic Building Blocks;Sulfonyl Hydrazides;Sulfur Compounds;Aromatic Hydrazides, Hydrazines, Hydrazones and Oximes;bc0001
Mol File:1576-35-8.mol
4-Methylbenzenesulfonhydrazide Structure
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)
Fp 60°C
storage temp. Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
solubility 5g/l
form Powder
pka9.39±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
InChIKeyICGLPKIVTVWCFT-UHFFFAOYSA-N
LogP0.55 at 25℃
CAS DataBase Reference1576-35-8(CAS DataBase Reference)
EPA Substance Registry SystemBenzenesulfonic 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 Information
ProviderLanguage
p-Toluenesulfonhydrazide English
SigmaAldrich English
ACROS English
ALFA English
4-Methylbenzenesulfonhydrazide Usage And Synthesis
Usesp-Toluenesulfonyl Hydrazide is a reactant that has been used in the synthesis of paspaline.
Chemical Propertieswhite to off-white powder
Uses4-Methylbenzenesulfonhydrazide was widely used reagent for the preparation of tosylhydrazones.
Applicationp-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.
Reactions4-Methylbenzenesulfonhydrazide as hydrogen donor in reduction reactions:reduction reaction of 4-MethylbenzenesulfonhydrazideA 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 ExplosibilityNot classified
Synthesis
Tosyl chloride

98-59-9

4-Methylbenzenesulfonhydrazide

1576-35-8

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 MethodsDissolve 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
Tag:4-Methylbenzenesulfonhydrazide(1576-35-8) Related Product Information
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