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1576-35-8

Basic Information
CAS No.: 1576-35-8
Name: Benzenesulfonic acid,4-methyl-, hydrazide
Molecular Structure:
Molecular Structure of 1576-35-8 (Benzenesulfonic acid,4-methyl-, hydrazide)
Formula: C7H10N2O2S
Molecular Weight: 186.23
Synonyms: p-Toluenesulfonylhydrazine;p-Tosyl hydrazide;Unifor H;p-Methylbenzenesulfonic acid hydrazide;p-Methylphenylsulfonylhydrazine;p-Toluenesulfonyl hydrazide;(4-Tolylsulfonyl)hydrazide;4-Methylbenzenesulfonicacid hydrazide;Cellmic H;
EINECS: 216-407-3
Density: 1.298 g/cm3
Melting Point: 103-108 °C(lit.)
Boiling Point: 340.5 °C at 760 mmHg
Flash Point: 159.7 °C
Solubility: water: 5 g/L (15 °C)
Appearance: white to off-white powder
Hazard Symbols: FlammableF,HarmfulXn
Risk Codes: 11-22-44
Safety: 16
Transport Information: UN 3226 4.1
PSA: 80.57000
LogP: 2.31900
Synthetic route
104-15-4

toluene-4-sulfonic acid

1576-35-8

toluene-4-sulfonic acid hydrazide

Conditions
ConditionsYield
With carbazic acid In neat (no solvent) at 100℃; for 5h; Green chemistry;94%
Multi-step reaction with 2 steps
1: triethylamine / acetonitrile / 0.01 h / 20 °C / Sonication
2: hydrazine hydrate / 0.02 h / Sonication
View Scheme
98-59-9

p-toluenesulfonyl chloride

1576-35-8

toluene-4-sulfonic acid hydrazide

Conditions
ConditionsYield
With hydrazine hydrate In tetrahydrofuran; water at 0 - 20℃;92%
With hydrazine hydrate In tetrahydrofuran; water at 5℃;92%
With hydrazine hydrate In dichloromethane for 0.25h;92%
260788-12-3

tert-butyl 2-tosylhydrazine-1-carboxylate

1576-35-8

toluene-4-sulfonic acid hydrazide

Conditions
ConditionsYield
With trifluoroacetic acid for 0.5h;78%
151416-59-0

dimethyl 4-amino-1-(p-toluenesulfonyl)pyrazolo<3,4-b>pyridine-5,6-dicarboxylate

A

1576-35-8

toluene-4-sulfonic acid hydrazide

B

4-amino-1H-pyrazolo<4',3':5,6>pyrido<2,3-d>pyridazine-5,8(6H,7H)-dione

Conditions
ConditionsYield
With hydrazine hydrate In ethanol 1.) reflux, 2 h, 2.) from 150 deg C to 200 deg C, 20 min.;A n/a
B 76%
64-17-5

ethanol

98-59-9

p-toluenesulfonyl chloride

1576-35-8

toluene-4-sulfonic acid hydrazide

Conditions
ConditionsYield
With hydrazine at 21℃; Rate constant;
7803-57-8

hydrazine hydrate

98-59-9

p-toluenesulfonyl chloride

1576-35-8

toluene-4-sulfonic acid hydrazide

Conditions
ConditionsYield
With water; benzene
1666-17-7

(E)-N′-benzylidene-4-methylbenzenesulfonohydrazide

1576-35-8

toluene-4-sulfonic acid hydrazide

Conditions
ConditionsYield
With water In phosphate buffer; ethanol at 25℃; pH=2.47; Kinetics; Further Variations:; pH-values;
1666-17-7

(E)-N′-benzylidene-4-methylbenzenesulfonohydrazide

A

100-52-7

benzaldehyde

B

1576-35-8

toluene-4-sulfonic acid hydrazide

Conditions
ConditionsYield
With water In ethanol for 3.8h; pH=2.47; Rate constant; Phosphoric acid buffer;
62460-99-5

(E)-4-methyl-N′-(1-phenylethylidene)benzenesulfonohydrazide

A

98-86-2

acetophenone

B

1576-35-8

toluene-4-sulfonic acid hydrazide

Conditions
ConditionsYield
With water In ethanol pH=2.47; Rate constant; Phosphoric acid buffer;
With water In ethanol pH=4.48; Rate constant; Citric acid buffer;
2232-08-8

N-tosylimidazole

1576-35-8

toluene-4-sulfonic acid hydrazide

Conditions
ConditionsYield
With hydrazine hydrate for 0.0166667h; Sonication;
80-48-8

methyl p-toluene sulfonate

1576-35-8

toluene-4-sulfonic acid hydrazide

Conditions
ConditionsYield
With hydrazine hydrate In methanol Reflux; Inert atmosphere;
108-94-1

cyclohexanone

1576-35-8

toluene-4-sulfonic acid hydrazide

4545-18-0

N'-cyclohexylidene-4-methylbenzene-1-sulfonohydrazide

Conditions
ConditionsYield
In methanol at 20℃; for 3h;100%
In methanol at 20℃; Inert atmosphere;99.5%
With hydrogenchloride In methanol for 24h; Heating;97%
66-77-3

1-naphthaldehyde

1576-35-8

toluene-4-sulfonic acid hydrazide

19350-73-3

(Z)-4-methyl-N'-(naphthalen-1-ylmethylene) benzenesulfonohydrazide

Conditions
ConditionsYield
In diethyl ether for 1h; Ambient temperature;100%
In methanol85%
In methanol at 60℃;
120-92-3

cyclopentanone

1576-35-8

toluene-4-sulfonic acid hydrazide

17529-98-5

cyclopentanone p-tolylsulfonylhydrazone

Conditions
ConditionsYield
In ethanol at 100℃; for 1h;100%
In ethanol at 100℃; for 1.66667h; Inert atmosphere;100%
In methanol at 20℃; Inert atmosphere;99.5%
684-16-2

Hexafluoroacetone

1576-35-8

toluene-4-sulfonic acid hydrazide

N-tosyl-N'-(1-hydroxy-1-trifluoromethyl-2,2,2-trifluoroethyl)hydrazine

Conditions
ConditionsYield
for 3h;100%
529-34-0

3,4-dihydronaphthalene-1(2H)-one

1576-35-8

toluene-4-sulfonic acid hydrazide

17336-59-3

1-tetralone tosylhydrazone

Conditions
ConditionsYield
In methanol at 20℃; Schlenk technique;100%
In methanol at 20℃;88%
Stage #1: 3,4-dihydronaphthalene-1(2H)-one With methanol for 0.25h; Heating / reflux;
Stage #2: toluene-4-sulfonic acid hydrazide With toluene-4-sulfonic acid In methanol for 4.5h; Heating / reflux;
87%
502-49-8

cycloactanone

1576-35-8

toluene-4-sulfonic acid hydrazide

2567-85-3

cyclooctanone p-tolylsulfonylhydrazone

Conditions
ConditionsYield
In ethanol at 100℃; for 1h;100%
In ethanol at 100℃; for 1.66667h; Inert atmosphere;100%
In methanol at 20℃; Schlenk technique;100%
5164-64-7

bicyclo[2.1.1]hexan-2-one

1576-35-8

toluene-4-sulfonic acid hydrazide

62708-51-4

bicyclo<2.1.1>hexan-2-one (p-tolylsulfonyl)hydrazone

Conditions
ConditionsYield
In methanol for 8h; Heating;100%
10265-39-1

7,7-dimethoxynorbornan-2-one

1576-35-8

toluene-4-sulfonic acid hydrazide

53329-08-1, 74035-49-7

7,7-dimethoxybicyclo<2.2.1>heptan-2-one p-toluenesulfonylhydrazone

Conditions
ConditionsYield
In methanol for 24h; Ambient temperature;100%
6102-41-6, 6102-44-9, 14116-78-0, 70749-10-9, 70749-11-0, 78341-47-6

rel-(4aS,8aS)-1,2,3,4,4a,5,8,8a-octahydronaphthalen-2-one

1576-35-8

toluene-4-sulfonic acid hydrazide

111219-19-3

C17H22N2O2S

Conditions
ConditionsYield
In ethanol for 1h; Heating;100%
2009-81-6

2-dimethylaminomethylene-1,3-bis(dimethylimonio)propane diperchlorate

1576-35-8

toluene-4-sulfonic acid hydrazide

137305-40-9

1-(4'-Methylphenylsulfonyl)-4-pyrazolecarboxaldehyde 4'-methylphenylsulfonylhydrazone

Conditions
ConditionsYield
With sodium carbonate In ethanol Ambient temperature;100%
132272-85-6

dimethyl cis-1,2-dimethyl-5-oxocyclohex-3-ene-1,2-dicarboxylate

1576-35-8

toluene-4-sulfonic acid hydrazide

C19H24N2O6S

Conditions
ConditionsYield
In methanol 1/ 21 h, RT, 2/ 20 min, reflux;100%
129001-03-2, 129098-99-3

(1S,5R)-9-(tert-butoxycarbonyl)-5-(methoxycarbonyl)-9-azabicyclo<4.2.1>-nonan-2-one

1576-35-8

toluene-4-sulfonic acid hydrazide

129001-08-7, 129099-07-6, 129099-08-7, 129099-09-8

(1S,5S)-9-(tert-butoxycarbonyl)-5-(methoxycarbonyl)-9-azabicyclo<4.2.1>nonan-2-one (4-tolylsulfonyl)hydrazone

Conditions
ConditionsYield
With pyridine; succinic acid anhydride; dmap; 3 A molecular sieve; pyridinium p-toluenesulfonate 1) CH2Cl2, RT, 3 h; 2) overnight;100%
132235-18-8

pentaspiro[2.0.3.0.3.0.3.0.3.0]nonadecane-1-carbaldehyde

1576-35-8

toluene-4-sulfonic acid hydrazide

132235-19-9

N-pentaspiro[2.0.3.0.3.0.3.0.3.0]nonadec-1-ylidene-N'-(p-tosyl)hydrazine

Conditions
ConditionsYield
With triethylamine In dichloromethane100%
132235-24-6

hexaspiro[2.0.3.0.3.0.3.0.3.0.3.0]tricosane-1-carbaldehyde

1576-35-8

toluene-4-sulfonic acid hydrazide

132235-25-7

N-hexaspiro[2.0.3.0.3.0.3.0.3.0.3.0]tricosan-1-ylidene-N'-(p-tosyl)hydrazine

Conditions
ConditionsYield
With triethylamine In dichloromethane100%
132235-32-6

[2-13C]hexaspiro[2.0.3.0.3.0.3.0.3.0.3.0]tricosane-1-carbaldehyde

1576-35-8

toluene-4-sulfonic acid hydrazide

132235-33-7

[2-13C]-N-hexaspiro[2.0.3.0.3.0.3.0.3.0.3.0]tricosan-1-ylidene-N'-(p-tosyl)hydrazine

Conditions
ConditionsYield
With triethylamine In dichloromethane100%
78167-14-3

9-Chloro-2,3-dihydro-1-thiaphenalen-3-one

1576-35-8

toluene-4-sulfonic acid hydrazide

78167-15-4

9-Chloro-2,3-dihydro-1-thiaphenalene-3-tosylhydrazone

Conditions
ConditionsYield
In ethanol for 6h; Heating;100%
111476-69-8

methyl 4-O-acetyl-2-O-benzoyl-6-deoxy-α-L-arabinohexopyranosid-3-ulose

1576-35-8

toluene-4-sulfonic acid hydrazide

113668-65-8

methyl 4-O-acetyl-2-O-benzoyl-6-deoxy-α-L-arabinohexapyranosid-3-ulose (p-tolylsulfonyl)hydrazone

Conditions
ConditionsYield
In ethanol for 0.5h; Ambient temperature;100%
104788-46-7

(1R,2S,7S,8S)-10-Benzoyl-4-oxo-9-oxa-10-aza-tricyclo[6.2.2.02,7]dodec-5-ene-7-carboxylic acid methyl ester

1576-35-8

toluene-4-sulfonic acid hydrazide

C26H27N3O6S

Conditions
ConditionsYield
In methanol100%
10265-39-1, 53585-72-1, 74035-53-3, 83829-13-4

(1R,4S)-7,7-Dimethoxy-bicyclo[2.2.1]heptan-2-one

1576-35-8

toluene-4-sulfonic acid hydrazide

Conditions
ConditionsYield
In methanol for 24h; Ambient temperature;100%
124549-68-4, 124600-41-5

1-hydroxy-7-azatricyclo<6.3.1.02.7>dodecan-9-one

1576-35-8

toluene-4-sulfonic acid hydrazide

124549-76-4, 124600-43-7

tosylhydrazone of 1-hydroxy-7-azatricyclo<6.3.1.02.7>dodecan-9-one

Conditions
ConditionsYield
With trimethyl orthoformate In methanol at 50℃; for 16h;100%
124549-68-4, 124600-41-5

1-hydroxy-7-azatricyclo<6.3.1.02.7>dodecan-9-one

1576-35-8

toluene-4-sulfonic acid hydrazide

124549-76-4, 124600-43-7

tosylhydrazone of 1-hydroxy-7-azatricyclo<6.3.1.02.7>dodecan-9-one

Conditions
ConditionsYield
With trimethyl orthoformate In methanol at 50℃; for 16h;100%
118451-46-0

heptacyclo<7.7.0.02,6.03,15.04,12.05,10.011,16>hexadecane-7,13-dione

1576-35-8

toluene-4-sulfonic acid hydrazide

C30H36N4O4S2

Conditions
ConditionsYield
In ethanol for 16h; Heating;100%
73586-29-5

4-methylene-2-adamantanone

1576-35-8

toluene-4-sulfonic acid hydrazide

87433-44-1, 87433-45-2, 102780-96-1

4-methylene-2-adamantanone tosylhydrazone

Conditions
ConditionsYield
In ethanol100%
1576-35-8

toluene-4-sulfonic acid hydrazide

502-42-1

cycloheptanone

56382-69-5

cycloheptanone p-tolylsulfonylhydrazone

Conditions
ConditionsYield
In methanol at 20℃; Schlenk technique;100%
In ethanol at 100℃; for 0.25h; Inert atmosphere;99%
In ethanol for 2h; Reflux; Inert atmosphere;90%
591-31-1

3-methoxy-benzaldehyde

1576-35-8

toluene-4-sulfonic acid hydrazide

19350-71-1

N'-(3-methoxybenzylidene)-4-methylbenzen sulfonohydrazide

Conditions
ConditionsYield
In ethanol for 8h; Reflux;100%
With polystyrene sulfonic acid In water at 100℃; for 0.0833333h; Wavelength; Reagent/catalyst; Solvent; Temperature; Microwave irradiation; Green chemistry;92%
In methanol at 20℃; for 3h;90%
1576-35-8

toluene-4-sulfonic acid hydrazide

173044-65-0

Benzoic acid (1R,2R,6S,7S,9R)-2-hydroxy-2,6,10,10-tetramethyl-3-oxo-11-oxa-tricyclo[7.2.1.01,6]dodec-7-yl ester

173044-66-1

3-(4-Toluenesulfonylhydrazono)-4β-hydroxy-9β-benzoyloxy-β-dihydroagarofuran

Conditions
ConditionsYield
In ethanol for 10h; Ambient temperature;100%
1576-35-8

toluene-4-sulfonic acid hydrazide

6630-33-7

ortho-bromobenzaldehyde

p-toluenesulfonylhydrazone of 2-bromobenzaldehyde

Conditions
ConditionsYield
100%
69649-19-0

pentacyclo[5.4.0.02,6.03,10.05,8]undecane-8-one

1576-35-8

toluene-4-sulfonic acid hydrazide

pentacyclo<5.4.0.02,6.03,10.05,9>undecan-8-one p-tosylhydrazone

Conditions
ConditionsYield
In ethanol at 80℃;100%
1576-35-8

toluene-4-sulfonic acid hydrazide

(+/-)-trans-2-<1-(4-isopropylphenyl)-1-methylethyl>cyclohexyl 2-oxo-2-phenylacetate

(+/-)-trans-2-<1-(4-isopropylphenyl)-1-methylethyl>cyclohexyl 2-oxo-2-phenylacetate tosylhydrazone

Conditions
ConditionsYield
In toluene Heating;100%
1576-35-8

toluene-4-sulfonic acid hydrazide

(+/-)-trans-2-<1-(4-t-butylphenyl)-1-methylethyl>cyclohexyl 2-oxo-2-phenylacetate

(+/-)-trans-2-<1-(4-t-butylphenyl)-1-methylethyl>cyclohexyl 2-oxo-2-phenylacetate tosylhydrazone

Conditions
ConditionsYield
In toluene Heating;100%
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    4-Methylbenzenesulfonhydrazide CAS: 1576-35-8

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    Product name 4-Methylbenzenesulfonhydrazide Synonyms p-Toluenesulfonhydrazide; p-Toluenesulfonyl hydrazide Toluene-4-sulphonohydrazide; 4-Methylbenzenesulfonylh

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    4-Methylbenzenesulfonhydrazide Basic information Product Name: 4-Methylbenzenesulfonhydrazide Synonyms: 4-methylbenzenesulfonicacidhydrazide;4-methyl-benzenesulfonicacihydrazide;Benzenes

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    4-Methylbenzenesulfonhydrazide

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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

The Benzenesulfonic acid,4-methyl-, hydrazide, with the CAS registry number 1576-35-8, is also known as p-Toluenesulfonylhydrazine. It belongs to the product category of Aromatic Hydrazides, Hydrazines, Hydrazones and Oximes. Its EINECS number is 216-407-3. This chemical's molecular formula is C7H10N2O2S and molecular weight is 186.23. What's more, its systematic name is 4-methylbenzenesulfonohydrazide. Its classification code is Drug / Therapeutic Agent. It is stable at common pressure and temperature, and it should be sealed and stored in a cool, ventilated and dry place. Moreover, it should be protected from oxides and heat. It is used in organic synthesis. It is also used as foaming agent.

Physical properties of Benzenesulfonic acid,4-methyl-, hydrazide are: (1)ACD/LogP: 0.32; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.32; (4)ACD/LogD (pH 7.4): 0.32; (5)ACD/BCF (pH 5.5): 1.03; (6)ACD/BCF (pH 7.4): 1.02; (7)ACD/KOC (pH 5.5): 35.57; (8)ACD/KOC (pH 7.4): 35.22; (9)#H bond acceptors: 4; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 49 Å2; (13)Index of Refraction: 1.575; (14)Molar Refractivity: 47.46 cm3; (15)Molar Volume: 143.4 cm3; (16)Polarizability: 18.81×10-24cm3; (17)Surface Tension: 48.9 dyne/cm; (18)Density: 1.298 g/cm3; (19)Flash Point: 159.7 °C; (20)Enthalpy of Vaporization: 58.41 kJ/mol; (21)Boiling Point: 340.5 °C at 760 mmHg; (22)Vapour Pressure: 8.55E-05 mmHg at 25°C.

Preparation: this chemical can be prepared by hydrazine hydrate and ptoluenesulfonyl chloride at the ambient temperature. This reaction will need reagent sulfuric acid.

Benzenesulfonic acid,4-methyl-, hydrazide can be prepared by hydrazine hydrate and ptoluenesulfonyl chloride at the ambient temperature

Uses of Benzenesulfonic acid,4-methyl-, hydrazide: it can be used to produce cyclohexanone (toluene-4-sulfonyl)-hydrazone at the ambient temperature. It will need solvent hexane with the reaction time of 2 hours. The yield is about 91%.

Benzenesulfonic acid,4-methyl-, hydrazide can be used to produce cyclohexanone (toluene-4-sulfonyl)-hydrazone at the ambient temperature

When you are using this chemical, please be cautious about it as the following:
This chemical is highly flammable, so you should keep it away from sources of ignition - No smoking. It is harmful if swallowed. Moreover, it has a risk of explosion if heated under confinement. 

You can still convert the following datas into molecular structure:
(1)SMILES: O=S(=O)(c1ccc(cc1)C)NN
(2)Std. InChI: InChI=1S/C7H10N2O2S/c1-6-2-4-7(5-3-6)12(10,11)9-8/h2-5,9H,8H2,1H3
(3)Std. InChIKey: ICGLPKIVTVWCFT-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 1200mg/kg (1200mg/kg)   Russian Pharmacology and Toxicology Vol. 36, Pg. 27, 1973.
rat LD50 oral 283mg/kg (283mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
International Journal of Toxicology. Vol. 16.

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