sodium tosylate
Conditions | Yield |
---|---|
With sodium carbonate In water at 5 - 90℃; for 4h; | 99% |
Conditions | Yield |
---|---|
With trifluoroacetic anhydride; sodium iodide In acetone for 13h; Ambient temperature; | A 6% B 84% |
Conditions | Yield |
---|---|
With sodium hydroxide In methanol; dichloromethane at 20℃; for 16h; | 82% |
toluene-4-sulfonic acid 2,2,2-trifluoro-1-trifluoromethyl-ethyl ester
sodium tosylate
Conditions | Yield |
---|---|
With sodium hydroxide In methanol; dichloromethane at 20℃; for 16h; | 82% |
toluene-4-sulfonic acid 2,2,2-trichloro-ethyl ester
sodium tosylate
Conditions | Yield |
---|---|
With sodium hydroxide In methanol; dichloromethane at 20℃; for 16h; | 80% |
Conditions | Yield |
---|---|
With sodium hydroxide In methanol; dichloromethane at 20℃; for 16h; | 72% |
Conditions | Yield |
---|---|
In ethyl acetate at 70℃; for 5.75h; Product distribution; | A 71% B 46% |
toluene-4-sulfonic acid 2,2,2-trifluoro-1-phenyl-ethyl ester
sodium tosylate
Conditions | Yield |
---|---|
With sodium hydroxide In methanol; dichloromethane at 20℃; for 16h; | 65% |
monochloronitromethane
sodium 4-methylbenzenesulfinate
A
di(p-tolyl) disulfide
B
nitromethyl p-tolyl sulfone
C
sodium tosylate
Conditions | Yield |
---|---|
With nitromethane In N,N-dimethyl-formamide for 24h; Ambient temperature; | A 2% B 7% C 64% D 26% |
methanol
nitromethane anion
p-toluenesulfonyl fluoride
A
sodium tosylate
B
methyl p-toluene sulfonate
Conditions | Yield |
---|---|
at 20℃; for 20h; | A 54% B 37% |
ethanol
toluene-p-sulfonyl bromide
A
sodium tosylate
B
ethyl ester of p-toluenesulfonic acid
Conditions | Yield |
---|---|
In water at 23℃; for 24h; | A 47% B 51% |
toluene-p-sulfonyl bromide
A
sodium tosylate
B
ethyl ester of p-toluenesulfonic acid
Conditions | Yield |
---|---|
In ethanol; water at 23℃; for 24h; | A 47% B 51% |
ethanol
sodium 4-methylbenzenesulfinate
A
bis(4-methylphenyl)disulfone
B
nitromethyl p-tolyl sulfone
C
sodium tosylate
D
ethyl ester of p-toluenesulfonic acid
Conditions | Yield |
---|---|
With bromonitromethane In water at 24℃; for 2h; | A 15% B 24% C 42% D 18% |
bromonitromethane
sodium 4-methylbenzenesulfinate
A
bis(4-methylphenyl)disulfone
B
nitromethyl p-tolyl sulfone
C
sodium tosylate
D
ethyl ester of p-toluenesulfonic acid
Conditions | Yield |
---|---|
In ethanol; water at 24℃; for 2h; | A 15% B 24% C 42% D 18% |
sodium 4-methylbenzenesulfinate
A
bis(4-methylphenyl)disulfone
B
nitromethyl p-tolyl sulfone
C
sodium tosylate
D
ethyl ester of p-toluenesulfonic acid
Conditions | Yield |
---|---|
With bromonitromethane In ethanol; water at 24℃; for 2h; | A 15% B 24% C 42% D 18% |
toluene-p-sulfonyl bromide
sodium nitromethane
A
bis(4-methylphenyl)disulfone
B
nitromethyl p-tolyl sulfone
C
sodium tosylate
D
ethyl ester of p-toluenesulfonic acid
Conditions | Yield |
---|---|
In ethanol; water at 23℃; for 24h; Further byproducts given; | A 17% B 8% C 41% D 30% |
toluene-p-sulfonyl bromide
A
bis(4-methylphenyl)disulfone
B
nitromethyl p-tolyl sulfone
C
sodium tosylate
D
ethyl ester of p-toluenesulfonic acid
Conditions | Yield |
---|---|
With sodium nitromethane In ethanol; water at 23℃; for 24h; Further byproducts given; | A 17% B 8% C 41% D 30% |
2-bromo-2-nitropropane
sodium 4-methylbenzenesulfinate
A
α-nitroisopropyl p-tolyl sulfone
B
sodium tosylate
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide for 0.333333h; | A 31% B 36% C 15% |
Conditions | Yield |
---|---|
With Na; MeOH In tetrahydrofuran; acetonitrile simultaneous addn. of solns. of Ni-complex and Na/MeOH to boiling MeCN (6 h), refluxing (36 h, pptn.), cooling to room temp.; chromy., crystn. (MeCN/MeOH); elem.anal.; | A 36% B n/a |
Conditions | Yield |
---|---|
With Na; MeOH In acetonitrile simultaneous addn. of solns. of Ni-complex and Na/MeOH to boiling MeCN (over 4 h), refluxing (24 h, pptn.), cooling to room temp.; filtration, volume reduction, repeated chromy. (Al2O3,MeCN), EtOH addn., crystn. (12 h, freezer), washing (EtOH), drying (vac.); elem. anal.; | A 36% B n/a |
Conditions | Yield |
---|---|
With cetyltrimethylammonim bromide; sodium bromide In water at 25℃; Rate constant; Equilibrium constant; Kinetics; | |
With sodium bromide In water at 25℃; Rate constant; | |
With (CTA)2SO4; sodium bromide In water at 25℃; Rate constant; |
Conditions | Yield |
---|---|
With cetyltrimethylammonium chloride; sodium chloride In water at 25℃; Rate constant; Equilibrium constant; Kinetics; | |
With sodium chloride In water at 25℃; Rate constant; | |
With (CTA)2SO4; sodium chloride In water at 25℃; Rate constant; |
chlorosulfonate de trimethylsilyle
4-tolyltrimethylstannane
sodium tosylate
Conditions | Yield |
---|---|
With sodium hydrogencarbonate 1) CCl4, rt, 1 h, 2) H2O, 20 min; Yield given. Multistep reaction; |
thiophenolate
toluene-4-sulfonic acid 2-isocyano-ethyl ester
A
sodium tosylate
B
(2-Isocyano-ethylsulfanyl)-benzene
Conditions | Yield |
---|---|
With sodium ethanolate Rate constant; Product distribution; multistep reaction, 1.) ethanol, 25 deg C; 2.) ethanol; |
p-tolylsulfonylmethyl p-toluenesulfonate
A
formaldehyd
B
sodium tosylate
C
sodium 4-methylbenzenesulfinate
Conditions | Yield |
---|---|
With sodium hydroxide; cetyltrimethylammonim bromide In water at 32.1℃; Rate constant; Mechanism; oder SDS, Igepal catalysis (25 deg C); solvolysis in H2O, H2O-dioxane; |
N-methyl-N-nitrosotoluene-p-sulfonamide
A
diazomethane
B
sodium tosylate
Conditions | Yield |
---|---|
With sodium hydroxide; cetyltrimethylammonim bromide In ethanol at 25℃; | |
With sodium hydroxide; sodium dodecyl-sulfate In ethanol at 25℃; Kinetics; other micellar aggregates; other solvent; |
α-p-Tolylsulfonylbenzyl-p-toluenesulfonat
A
sodium tosylate
B
benzaldehyde
C
sodium 4-methylbenzenesulfinate
Conditions | Yield |
---|---|
With sodium hydroxide; cetyltrimethylammonim bromide In water at 32.1℃; Rate constant; Mechanism; |
1-phenyl-2-(p-tolylsulfonyloxy)ethanone
sodium phenylsulfonate
A
sodium tosylate
B
α-phenylsulfonyloxyacetophenone
Conditions | Yield |
---|---|
With 18-crown-6 ether In sulfolane at 50℃; Rate constant; Equilibrium constant; |
Toluene-4-sulfonic acid 4-nitro-benzenesulfonylmethyl ester
A
formaldehyd
B
sodium tosylate
C
sodium 4-nitrobenzenesulfinate
Conditions | Yield |
---|---|
With sodium hydroxide; cetyltrimethylammonim bromide In water at 32.1℃; Rate constant; Mechanism; solvolysis in H2O-dioxane; |
Conditions | Yield |
---|---|
Equilibrium constant; |
Conditions | Yield |
---|---|
With iodine | 100% |
sodium tosylate
2,2-difluoro-1,3-dimethyl-imidazolidine
2-fluoro-1,3-dimethylimidazolinium p-toluenesulfonate
Conditions | Yield |
---|---|
In acetonitrile at 0 - 30℃; for 3h; Product distribution / selectivity; | 100% |
In [D3]acetonitrile at 20 - 30℃; for 3h; Product distribution / selectivity; |
sodium tosylate
(8S,9R)-(-)-N-benzylcinchonidinium chloride
N-9-benzylcinchonidinium p-toluenesulfonate
Conditions | Yield |
---|---|
In dichloromethane; water | 100% |
Conditions | Yield |
---|---|
In methanol at 60℃; for 1h; | 100% |
Conditions | Yield |
---|---|
In methanol at 60℃; for 1h; | 100% |
p-N,N-dimethylaminobenzamidopropyl(dimethyl)(lauryl)ammonium chloride
sodium tosylate
(p-methoxycinnamidopropyl)dimethylamine
Conditions | Yield |
---|---|
In water | 99.93% |
p-methoxy cinnamidopropyldimethyllauryl ammonium chloride
sodium tosylate
Conditions | Yield |
---|---|
In water | 99.83% |
Conditions | Yield |
---|---|
With iodine; triethylamine In methanol at 20℃; for 6h; | 98% |
Conditions | Yield |
---|---|
In [D3]acetonitrile at 25℃; for 12h; | 98% |
Conditions | Yield |
---|---|
In water at 20℃; for 4h; Inert atmosphere; | 98% |
Conditions | Yield |
---|---|
With sulfuric acid; triphenylphosphine In water at 50℃; for 10h; | 98% |
Conditions | Yield |
---|---|
Stage #1: titanium(IV) isopropylate; water; citric acid In tetrahydrofuran at 90℃; for 1h; Stage #2: sodium tosylate With sodium hydroxide In tetrahydrofuran pH=4.75; | 98% |
(4-methoxy-3-(trifluoromethyl)phenyl)boronic acid
2-(diacetoxyiodo)mesitylene
sodium tosylate
Conditions | Yield |
---|---|
Stage #1: (4-methoxy-3-(trifluoromethyl)phenyl)boronic acid With boron trifluoride diethyl etherate In dichloromethane at 0℃; for 0.166667h; Sealed tube; Inert atmosphere; Stage #2: 2-(diacetoxyiodo)mesitylene In dichloromethane at 0 - 20℃; Sealed tube; Inert atmosphere; Stage #3: sodium tosylate In dichloromethane; water for 0.005h; Inert atmosphere; | 98% |
Conditions | Yield |
---|---|
Stage #1: sodium tosylate; tert-butyl 2-(2-methoxyethoxymethyl)acrylate With iodine In ethyl acetate Stage #2: With triethylamine | 97% |
Conditions | Yield |
---|---|
With sulfuric acid; triphenylphosphine In water at 50℃; for 10h; | 97% |
1-(2-chlorophenyl)ethanone
sodium tosylate
1-(2-chlorophenyl)-2-(p-tosyl)ethanone
Conditions | Yield |
---|---|
With iodine; triethylamine In methanol at 20℃; for 6h; | 96% |
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; cetyltrimethylammonim bromide; triphenylphosphine In water at 70℃; for 3h; Tsuji-Trost Allylation; Micellar solution; Green chemistry; | 96% |
Conditions | Yield |
---|---|
With sulfuric acid; triphenylphosphine In water at 50℃; for 10h; | 96% |
Conditions | Yield |
---|---|
With hydrogenchloride In water at 80℃; for 6h; | 96% |
sodium tosylate
1,3,5-trimethyl-benzene
1,3,5-trimethyl-2-(toluene-4-sulfonyl)-benzene
Conditions | Yield |
---|---|
With methanesulfonic acid; phosphorus pentoxide at 20℃; for 24h; | 95% |
(μ-pyrazine)decaamminediruthenium(II,III) pentachloride
sodium tosylate
Creutz-Taube complex
Conditions | Yield |
---|---|
In water under Ar, a satd. aq. soln. of Na(tos) was added to a soln. of ((NH3)5Ru(N2C4H4)Ru(NH3)5)Cl5*5H2O in water; ppt. was filtered off, washed with ethanol and ether, dried in vac.; elem. anal.; | 95% |
2,6-dichlorostyrene
sodium tosylate
(E)-1,3-dichloro-2-(2-tosylvinyl)benzene
Conditions | Yield |
---|---|
With sodium periodate; acetic acid; potassium iodide In acetonitrile at 20℃; for 3h; | 95% |
1-hexadecyl-3-(6-hydroxyhexyl)imidazolium chloride
sodium tosylate
1-hexadecyl-3-(6-hydroxyhexyl)imidazolium tosylate
Conditions | Yield |
---|---|
In dichloromethane; water | 95% |
ethyl 2-benzoylacrylate
sodium tosylate
Conditions | Yield |
---|---|
With copper dichloride; palladium dichloride In 1,4-dioxane at 90℃; for 8h; Baylis-Hillman Reaction; | 95% |
Conditions | Yield |
---|---|
With copper dichloride; palladium dichloride In 1,4-dioxane at 90℃; for 8h; Baylis-Hillman Reaction; | 95% |
sodium tosylate
para-bromoacetophenone
1-(4-bromophenyl)-2-tosylethanone
Conditions | Yield |
---|---|
With iodine; triethylamine In methanol at 20℃; for 6h; | 95% |
Conditions | Yield |
---|---|
With iodine; triethylamine at 20℃; for 6h; | 95% |
2-vinylpyridine
sodium tosylate
4-methylphenyl 2-(2-pyridyl)ethyl sulfide
Conditions | Yield |
---|---|
With sulfuric acid; triphenylphosphine In water at 50℃; for 10h; | 95% |
Conditions | Yield |
---|---|
With 1,3,5-trichloro-2,4,6-triazine; 18-crown-6 ether In acetone for 20h; Heating; | 94% |
Stage #1: sodium tosylate With potassium phosphate; bis(trichloromethyl) carbonate In dichloromethane at 0 - 5℃; for 0.0833333h; Stage #2: With triethylamine In dichloromethane at 20℃; for 0.5h; | 93% |
With trichlorophosphate In sulfolane; acetonitrile at 68 - 72℃; for 0.666667h; | 87% |
Structure of Sodium p-toluenesulfonate (CAS NO.657-84-1):
IUPAC Name: 4-Methylbenzenesulfonic acid; sodium
Molecular Formula: C7H7NaO3S
Molar mass: 194.18 g/mol
Flash Point: 500 °C
Water Solubility: soluble
Stability: stable. incompatible with strong oxidizing agents.
H-Bond Donor: 1
H-Bond Acceptor: 3
Rotatable Bond Count: 1
Exact Mass: 195.009184
MonoIsotopic Mass: 195.009184
Topological Polar Surface Area: 54.4
Heavy Atom Count: 12
Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)O.[Na]
InChI: InChI=1S/C7H8O3S.Na/c1-6-2-4-7(5-3-6)11(8,9)10;/h2-5H,1H3,(H,8,9,10);
InChIKey: CUYTYLVEYFUAAX-UHFFFAOYSA-N
EINECS: 211-522-5
Sodium p-toluenesulfonate (CAS NO.657-84-1) is mainly used in industrial organic synthesis. It is also used for the synthesis of doxycycline, dipyridamole, naproxen, and for the production of amoxicillin, cefadroxil intermediate in medicine.
1. | ivn-mus LD50:1700 mg/kg | BJPCAL British Journal of Pharmacology and Chemotherapy. 14 (1959),536. |
Reported in EPA TSCA Inventory.
Hazard Codes: Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
WGK Germany: 1
RTECS: XT7350000
HS Code: 29041000
Moderately toxic by intravenous route. When heated to decomposition it emits toxic fumes of SOx and Na2O. See also SULFONATES.
Sodium p-toluenesulfonate (CAS NO.657-84-1) is also named as 4-Toluenesulfonic acid sodium salt ; AI3-50010 ; Benzenesulfonic acid, 4-methyl-, sodium salt ; HSDB 5738 ; NSC 203318 ; Naxonate hydrotrope ; Sodium 4-methylbenzenesulfonate ; Sodium p-methylbenzenesulfonate ; Sodium p-tolyl sulfonate ; Sodium p-tolylsulfonate ; Sodium paratoluene sulphonate ; Sodium toluene-p-sulphonate ; Sodium toluenesulfonate ; Sodium tosylate ; Tosylate, sodium ; p-Toluenesulfonic acid sodium salt ; para-Toluenesulfonic acid, sodium salt . Sodium p-toluenesulfonate (CAS NO.657-84-1) is white powder.
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