Conditions | Yield |
---|---|
Stage #1: 4-nitro-aniline With hydrogenchloride; sodium nitrite In water at -5℃; for 0.166667h; Stage #2: With thionyl chloride; copper(l) chloride In water at -5 - 0℃; for 1.75h; | 99% |
Stage #1: 4-nitro-aniline With hydrogenchloride In water at 30 - 50℃; for 1h; Sandmeyer reaction; Stage #2: With sodium nitrite In water at -5 - 0℃; for 0.916667h; Sandmeyer reaction; Stage #3: With thionyl chloride; water; copper(l) chloride at -5 - 0℃; for 2.83333h; Sandmeyer reaction; | 81.7% |
Stage #1: 4-nitro-aniline With hydrogenchloride; acetic acid Stage #2: With sodium nitrite In water at -10 - -5℃; for 0.75h; Stage #3: With hydrogenchloride; sulfur dioxide; acetic acid; copper(l) chloride In water at 10℃; for 0.5h; | 68% |
With copper(I) chloride; hydrogenchloride; sulfur dioxide; acetic acid; sodium nitrite Multistep reaction; | |
With tert.-butylnitrite; sulfur dioxide; N-benzyl-N,N,N-triethylammonium chloride; ethylene glycol; copper dichloride In dichloromethane; acetonitrile at 0 - 20℃; Automated synthesizer; |
Conditions | Yield |
---|---|
With dihydrogen peroxide; zirconium(IV) chloride In water; acetonitrile at 25℃; for 0.0333333h; | 98% |
With thionyl chloride; dihydrogen peroxide In water; acetonitrile at 25℃; for 0.0166667h; | 98% |
With sulfuryl dichloride; potassium nitrate In acetonitrile at 0℃; for 1h; | 97% |
Conditions | Yield |
---|---|
With dihydrogen peroxide; zirconium(IV) chloride In water; acetonitrile at 25℃; for 0.0166667h; | 96% |
With N,N,N',N'-tetrachlorobenzene-1,3-disulphonamide; tetrabutyl-ammonium chloride; water In acetonitrile at 0 - 20℃; for 0.333333h; | 96% |
With trichloroisocyanuric acid; tetrabutylammomium bromide; water In acetonitrile at 0 - 20℃; for 0.333333h; | 96% |
1-acetylsulfanyl-4-nitro-benzene
4-Nitrobenzenesulfonyl chloride
Conditions | Yield |
---|---|
With hydrogenchloride; N-chloro-succinimide In acetonitrile at 10℃; | 95.6% |
Conditions | Yield |
---|---|
With sulfuryl dichloride; sodium sulfate In water; chlorobenzene | 95% |
Conditions | Yield |
---|---|
With 2,2,4,4,6,6-hexachloro-1,3,5-triaza-2,4,6-triphosphorine; potassium chloride at 25℃; for 0.0333333h; Neat (no solvent); | 95% |
Conditions | Yield |
---|---|
With copper(l) chloride; silver(l) oxide In acetic acid | 78% |
With sulfur dioxide; copper(l) chloride | |
With sulfur dioxide; copper(II) sulfate In acetic acid at 6 - 20℃; Yield given; |
Conditions | Yield |
---|---|
With N-chloro-succinimide In water; acetonitrile at 35℃; for 0.25h; | A 62% B 30% |
Conditions | Yield |
---|---|
With thionyl chloride; tris(bipyridine)ruthenium(II) dichloride hexahydrate In water; acetonitrile at 20℃; for 20h; Sealed tube; Irradiation; | 52% |
nitrostyrene
4-nitrobenzenediazonium chloride
A
1-Phenyl-2-nitroethyl-p-nitrophenylsulfon
B
4-Nitrobenzenesulfonyl chloride
Conditions | Yield |
---|---|
With sulfur dioxide In acetic acid; acetone at 15 - 20℃; | A 45% B n/a |
2-[(E)-2-nitroethenyl]furan
4-nitrobenzenediazonium chloride
A
4-Nitrobenzenesulfonyl chloride
Conditions | Yield |
---|---|
With sulfur dioxide In acetic acid; acetone at 15 - 20℃; | A n/a B 26% |
Conditions | Yield |
---|---|
With nitric acid; acetic acid neben anderen Produkten; |
Conditions | Yield |
---|---|
With chlorosulfonic acid at 25℃; Rate constant; E(activ.), var. temperatures; |
Conditions | Yield |
---|---|
With thionyl chloride In N,N-dimethyl-formamide |
4-Nitrobenzenesulfonyl chloride
Conditions | Yield |
---|---|
With chlorosulfonic acid at 100℃; |
4-Nitrobenzenesulfonyl chloride
Conditions | Yield |
---|---|
With phosphorus pentachloride |
4-Nitrobenzenesulfonyl chloride
Conditions | Yield |
---|---|
With phosphorus pentachloride |
sulfuric acid
nitric acid
benzenesulfonyl chloride
A
2-Nitrobenzenesulfonyl chloride
B
3-nitrobenzenesulphonyl chloride
C
4-Nitrobenzenesulfonyl chloride
4-nitrobenzenesulfenyl chloride
dichloromethane
A
di(p-nitrophenyl) disulfide
B
4-nitrobenzenesulfonyl fluoride
C
4-Nitrobenzenesulfonyl chloride
chlorosulfonic acid
p-nitrobenzenesulfonic acid
4-Nitrobenzenesulfonyl chloride
Conditions | Yield |
---|---|
at 100℃; Reaktion des Ammoniumsalzes; |
1-(benzylsulphanyl)-4-Nitrobenzene
chlorine
acetic acid
4-Nitrobenzenesulfonyl chloride
S-nitrophenyl O-ethylxanthate
4-Nitrobenzenesulfonyl chloride
Conditions | Yield |
---|---|
With water; chlorine at 5 - 10℃; |
2-phenylaniline
4-Nitrobenzenesulfonyl chloride
N-([1,1'-biphenyl]-2-yl)-4-nitrobenzenesulfonamide
Conditions | Yield |
---|---|
With pyridine at 140℃; for 0.5h; | 100% |
Conditions | Yield |
---|---|
With pyridine at 0 - 25℃; | 100% |
With pyridine In dichloromethane for 4.5h; Reflux; | 98% |
With zinc oxide-nanoparticle at 50℃; for 0.75h; Neat (no solvent); chemoselective reaction; | 97% |
benzylamine
4-Nitrobenzenesulfonyl chloride
N-benzyl-4-nitrobenzenesulfonamide
Conditions | Yield |
---|---|
With triethylamine In dichloromethane 1) 0 deg C, 1 h, 2) room temperature; | 100% |
In dichloromethane at 20℃; for 0.5h; Inert atmosphere; | 97% |
With 4-methyl-morpholine In dichloromethane at 0 - 20℃; | 89% |
Conditions | Yield |
---|---|
With ammonia | 100% |
With ammonium hydroxide In tetrahydrofuran for 1h; Cooling with ice; | 97% |
With ammonium hydroxide; silica gel In dichloromethane at 20℃; for 0.75h; | 95% |
4-Nitrobenzenesulfonyl chloride
p-nitrobenzenesulfonyl azide
Conditions | Yield |
---|---|
With sodium azide In water; acetone at 0 - 20℃; for 11h; Sealed tube; | 100% |
With sodium azide In ethanol at 25℃; for 0.05h; | 96% |
With sodium azide; tributyl methyl phsophonium chloride immobibized on polystyrene matrix In 1,2-dichloro-ethane at 45℃; for 4h; | 93% |
4-chloro-aniline
4-Nitrobenzenesulfonyl chloride
4-nitro-N-(4-chlorophenyl)benzenesulfonamide
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 20℃; | 100% |
With pyridine at 20℃; | 84% |
With sodium acetate In methanol; water at 60℃; | 71% |
4-methoxy-aniline
4-Nitrobenzenesulfonyl chloride
N-(4-methoxyphenyl)-4-nitrobenzene sulphonamide
Conditions | Yield |
---|---|
With pyridine In 1,2-dichloro-ethane at 150℃; for 0.166667h; Microwave irradiation; | 100% |
With pyridine at 20℃; | 98% |
In ethanol at 25℃; | 96% |
(S)-Methyl lactate
4-Nitrobenzenesulfonyl chloride
(S)-(-)-2-(4'-Nitrophenylsulfonyloxy)-propionsaeure-methylester
Conditions | Yield |
---|---|
With triethylamine | 100% |
With dmap; triethylamine In dichloromethane at 0℃; | 100% |
With triethylamine In ethyl acetate at 26.85 - 59.85℃; | 20% |
With triethylamine In ethyl acetate 1.) room temp., overnight, 2.) 60 deg C, 1h; | 361 g |
4-Nitrobenzenesulfonyl chloride
(2R,3S)-3-tert-butoxycarbonylamino-1-isobutylamino-4-phenyl-2-butanol
[(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In dichloromethane; water at 20℃; for 21h; | 100% |
With sodium hydrogencarbonate In dichloromethane; water at 23℃; for 12h; | 96% |
With triethylamine In isopropyl alcohol at 60 - 65℃; for 1h; | 96.5% |
(S)-Alaninol
4-Nitrobenzenesulfonyl chloride
(2S)-2-methyl-1-[(4-nitrophenyl)sulfonyl]aziridine
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 20℃; for 5h; | 100% |
In pyridine; dichloromethane at 0 - 20℃; | 98% |
2-Aminobenzyl alcohol
4-Nitrobenzenesulfonyl chloride
N-[2-(hydroxymethyl)phenyl]-4-nitrobenzene-1-sulfonamide
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 20℃; for 3h; | 100% |
With pyridine In chloroform at 20℃; Inert atmosphere; | 82% |
With pyridine In dichloromethane for 1.5h; | 70% |
2-[(1,1,2,2-tetramethyl-1-silapropoxy)methyl]phenylamine
4-Nitrobenzenesulfonyl chloride
N-(2-(((tert-butyldimethylsilyl)oxy)methyl)phenyl)-4-nitrobenzenesulfonamide
Conditions | Yield |
---|---|
With TEA In dichloromethane at 20℃; for 3h; | 100% |
In dichloromethane at 20℃; for 3h; Inert atmosphere; | 71% |
In dichloromethane |
2-[(1,1,2,2-tetramethyl-1-silapropoxy)methyl]phenylamine
4-Nitrobenzenesulfonyl chloride
Conditions | Yield |
---|---|
With TEA In dichloromethane at 20℃; for 5h; | 100% |
1-amino-3-methylbenzene
4-Nitrobenzenesulfonyl chloride
4-nitro-N-(m-tolyI)benzenesulfonamide
Conditions | Yield |
---|---|
With pyridine In 1,2-dichloro-ethane at 150℃; for 0.166667h; Microwave irradiation; | 100% |
With pyridine In dichloromethane at 20℃; Inert atmosphere; | 99% |
With pyridine In dichloromethane at 20℃; Inert atmosphere; | 99% |
4-Nitrobenzenesulfonyl chloride
2-{[(dimethylamino)methylidene]amino}-3,5-dihydro-7-iodo-3-[(pivaloyloxy)methyl]-4H-pyrrolo[3,2-d]pyrimidin-4-one
C21H23IN6O7S
Conditions | Yield |
---|---|
With sodium hydride In dichloromethane | 100% |
N-(5-aminopyridin-2-yl)acetamide
4-Nitrobenzenesulfonyl chloride
N-(5-(4-nitrophenylsulfonamido)pyridin-2-yl)acetamide
Conditions | Yield |
---|---|
Stage #1: N-(5-aminopyridin-2-yl)acetamide; 4-Nitrobenzenesulfonyl chloride With triethylamine In dichloromethane at 20℃; for 18h; Stage #2: With sodium hydroxide; water In methanol for 18h; Stage #3: With hydrogenchloride In water | 100% |
4-Nitrobenzenesulfonyl chloride
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In dichloromethane for 4h; Reflux; Inert atmosphere; | 100% |
C24H43NO4Si
4-Nitrobenzenesulfonyl chloride
2-(tert-butoxycarbonylamino)-3,3-dimethyl-3-[2,4-dimethyl-6-(nitrobenzene-4-sulfonyloxy)phenyl]propyl tert-butyldimethylsilyl ether
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 5.5h; Inert atmosphere; Reflux; | 100% |
Conditions | Yield |
---|---|
With sodium carbonate In dichloromethane; water for 2h; | 100% |
66% | |
With triethylamine In dichloromethane at 0 - 20℃; |
2-[3-(tritylamino)phenyl]ethanol
4-Nitrobenzenesulfonyl chloride
4-nitrobenzenesulfonic acid 2-[3-(tritylamino)phenyl]ethyl ester
Conditions | Yield |
---|---|
Stage #1: 2-[3-(tritylamino)phenyl]ethanol; 4-Nitrobenzenesulfonyl chloride With 1,4-diaza-bicyclo[2.2.2]octane In dichloromethane at 0℃; for 0.75h; Inert atmosphere; Stage #2: With sodium hydrogencarbonate In dichloromethane; water | 100% |
ethyl 2-amino-4-(tetrahydro-4H-pyran-4-ylidene)butanoate
4-Nitrobenzenesulfonyl chloride
ethyl 2-{[(4-nitrophenyl)sulfonyl]amino}-4-(tetrahydro-4Hpyran-4-ylidene)butanoate
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 2h; Inert atmosphere; | 100% |
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 2h; Inert atmosphere; | 100% |
[(3R)-5-methyl-2,3-dihydro-1-benzofuran-3-yl]methanol
4-Nitrobenzenesulfonyl chloride
[(3S)-5-methyl-2,3-dihydro-1-benzofuran-3-yl]methyl 4-nitrobenzenesulfonate
Conditions | Yield |
---|---|
With dmap; triethylamine at 20℃; | 100% |
phenylmethyl 1-piperazinecarboxylate
4-Nitrobenzenesulfonyl chloride
4-(4-nitrobenzenesulfonyl)piperazine-1-carboxylic acid benzyl ester
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 1h; Inert atmosphere; | 100% |
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 1h; Inert atmosphere; | 100% |
With triethylamine In dichloromethane at 0 - 25℃; for 2h; Inert atmosphere; | 74% |
1-(tert-butoxycarbonyl)-4-aminopiperidine
4-Nitrobenzenesulfonyl chloride
4-(4-nitrobenzenesulfonylamino)piperidine-1-carboxylic acid tert-butyl ester
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; | 100% |
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; |
4-Nitrobenzenesulfonyl chloride
piperidin-4-ylcarbamic acid benzyl ester
[1-(4-nitrobenzenesulfonyl)piperidin-4-yl]carbamic acid benzyl ester
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; | 100% |
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; | 100% |
(2R,3S)-2-(4-fluorophenyl)-3-isopropylaziridine
4-Nitrobenzenesulfonyl chloride
(2R,3S)-2-(4-fluorophenyl)-3-isopropyl-1-(4-nitrophenylsulfonyl)aziridine
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; | 100% |
(2S,3R)-2-(4-fluorophenyl)-3-isopropylaziridine
4-Nitrobenzenesulfonyl chloride
(2S,3R)-2-(4-fluorophenyl)-3-isopropyl-1-(4-nitrophenylsulfonyl)aziridine
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; | 100% |
(2R,3S)-2-phenyl-3-isopropylaziridine
4-Nitrobenzenesulfonyl chloride
(2R,3S)-2-phenyl-3-isopropyl-1-(4-nitrophenylsulfonyl)aziridine
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; | 100% |
(2R,3S)-(-)-2-phenyl-3-methyl-1-aziridine
4-Nitrobenzenesulfonyl chloride
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; | 100% |
(2S,3R)-2-(4-fluorophenyl)-3-methylaziridine
4-Nitrobenzenesulfonyl chloride
(2S,3R)-2-(4-fluorophenyl)-3-methyl-1-(4-nitrophenylsulfonyl)aziridine
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; | 100% |
Molecule structure of 4-Nitrobenzenesulfonyl chloride (CAS NO.98-74-8):
IUPAC Name: 4-Nitrobenzenesulfonyl chloride
Molecular Weight: 221.61826 g/mol
Molecular Formula: C6H4ClNO4S
Density: 1.606 g/cm3
Melting Point: 75 °C
Boiling Point: 349.7 °C at 760 mmHg
Flash Point: 165.3 °C
Index of Refraction: 1.588
Molar Refractivity: 46.43 cm3
Molar Volume: 137.9 cm3
Polarizability: 18.4×10-24 cm3
Surface Tension: 57.1 dyne/cm
Enthalpy of Vaporization: 57.07 kJ/mol
Vapour Pressure: 9.33E-05 mmHg at 25 °C
Water Solubility: insoluble
Sensitive: moisture sensitive
XLogP3: 2.1
H-Bond Acceptor: 4
Rotatable Bond Count: 1
Exact Mass: 220.954956
MonoIsotopic Mass: 220.954956
Topological Polar Surface Area: 77.3
Heavy Atom Count: 13
Complexity: 283
Canonical SMILES: C1=CC(=CC=C1[N+](=O)[O-])S(=O)(=O)Cl
InChI: InChI=1S/C6H4ClNO4S/c7-13(11,12)6-3-1-5(2-4-6)8(9)10/h1-4H
InChIKey: JXRGUPLJCCDGKG-UHFFFAOYSA-N
EINECS: 202-697-9
Product Categories: Benzene derivatives; Benzene series; Phenyls & Phenyl-Het; Sulphonyl Chlorides; Phenyls & Phenyl-Het; Sulphonyl Chlorides; Organic Building Blocks; Sulfonyl Halides; Sulfur Compounds
4-Nitrobenzenesulfonyl chloride (CAS NO.98-74-8) is commonly used as a medicine and dyes intermediates.
Mixed 60g 4, 4'-dinitro-diphenyl disulfide, 300ml concentrated hydrochloric acid and 60ml concentrated nitric acid, heated to 80 °C, which leads to chlorine reaction. At the end of the reaction, dump out the resulting chloride, washed with 80 °C water, get the crude, after acetic acid recrystallization may get 72g product.
Hazard Codes: C
Risk Statement: 34-52/53
R34:Causes burns.
R52/53:Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
Safety Statements: 26-36/37/39-45-61
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S61:Avoid release to the environment. Refer to special instructions / safety data sheets.
RIDADR: UN 3261 8/PG 2
WGK Germany: 3
F: 21
Hazard Note: Corrosive/Moisture Sensitive
HazardClass: 8
PackingGroup: II
HS Code: 29049085
4-Nitrobenzenesulfonyl chloride (CAS NO.98-74-8) is also named as 4-Nitrobenzenesulfonic acid chloride ; 4-Nitrophenylsulfonyl chloride ; AI3-52248 ; NSC 13065 ; p-Nitrobenzenesulfonyl chloride ; p-Nitrophenylsulfonyl chloride . 4-Nitrobenzenesulfonyl chloride (CAS NO.98-74-8) is yellow to brown powder.
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