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CAS RN: 1694-92-4 | Product Number: N0142
2-Nitrobenzenesulfonyl Chloride
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Purity: >95.0%(GC)(T)
Synonyms:
- o-Ns-Cl
Product Documents:
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| Product Number | N0142 |
| Purity / Analysis Method | >95.0%(GC)(T) |
| Molecular Formula / Molecular Weight | C__6H__4ClNO__4S = 221.61 |
| Physical State (20 deg.C) | Solid |
| Storage Temperature | Room Temperature (Recommended in a cool and dark place, <15°C) |
| Store Under Inert Gas | Store under inert gas |
| Condition to Avoid | Moisture Sensitive |
| CAS RN | 1694-92-4 |
| Reaxys Registry Number | 521155 |
| PubChem Substance ID | 87573527 |
| SDBS (AIST Spectral DB) | 4477 |
| MDL Number | MFCD00007430 |
Specifications
| Appearance | White to Yellow to Orange powder to crystal |
| Purity(GC) | min. 95.0 % |
| Purity(Argentometric Titration) | min. 95.0 % |
| Melting point | 64.0 to 70.0 °C |
Properties (reference)
| Melting Point | 64 °C |
| Solubility (soluble in) | Toluene |
GHS
| Pictogram |
|
| Signal Word | Danger |
| Hazard Statements | H314 : Causes severe skin burns and eye damage. H290 : May be corrosive to metals. |
| Precautionary Statements | P501 : Dispose of contents/ container to an approved waste disposal plant. P260 : Do not breathe dusts or mists. P234 : Keep only in original container. P264 : Wash skin thoroughly after handling. P280 : Wear protective gloves/ protective clothing/ eye protection/ face protection. P390 : Absorb spillage to prevent material damage. P303 + P361 + P353 : IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water/shower. P301 + P330 + P331 : IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. P363 : Wash contaminated clothing before reuse. P304 + P340 + P310 : IF INHALED: Remove person to fresh air and keep comfortable for breathing. Immediately call a POISON CENTER/doctor. P305 + P351 + P338 + P310 : IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER/doctor. P406 : Store in corrosive resistant container with a resistant inner liner. P405 : Store locked up. |
Related Laws:
Transport Information:
| UN Number | UN3261 |
| Class | 8 |
| Packing Group | II |
| H.S.code* | 2904.99-000 |
Application
TCI Practical Example: Nosylation of Amino Group Using o-Ns-Cl
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Used Chemicals
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Procedure
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To a solution of 4-methoxybenzylamine (1.00 g, 7.29 mmol) and triethylamine (1.11 mL, 8.02 mmol, 1.1 eq.) in dichloromethane (14.6 mL) was added o-Ns-Cl (1.70 g, 7.65 mmol, 1.05 eq.) at 0 °C and the mixture was stirred for 2 h at room temperature. The reaction mixture was quenched with 1 mol/L HCl aq. (14.6 mL) with cooling to 0 °C and the water layer was extracted with dichloromethane (4 x 10 mL). The combined organic layer was washed with brine, dried over sodium sulfate and filtered to give 1 as a pale yellow solid (2.32 g, 99% yield).
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Experimenter’s Comments
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The reaction mixture was monitored by TLC (ethyl acetate:hexane = 1:1, Rf = 0.6).
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Analytical Data
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Compound 1
1H NMR (270 MHz, DMSO-d6); δ 8.57 (t, J = 6.2 Hz, 1H), 7.75-7.92 (m, 4H), 7.15 (d, J = 8.8 Hz, 1H), 6.79 (d, J = 8.8 Hz, 1H), 4.08 (d, J = 6.2 Hz, 1H), 3.70 (s, 3H).
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Other Reference
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- PREPARATION OF SECONDARY AMINES FROM PRIMARY AMINES VIA 2-NITROBENZENESULFONAMIDES: N-(4-METHOXYBENZYL)-3-PHENYLPROPYLAMINE
Application
Ns-Protection of Primary Amino Groups
Typical Procedure:
To a 300 mL two-necked round-bottomed flask, 4-methoxybenzylamine (6.81 g, 49.6 mmol), 100 mL of dichloromethane and triethylamine (6.93 mL, 49.6 mmol) are added under nitrogen. The mixture is stirred and cooled with an ice bath while 2-nitrobenzenesulfonyl chloride (10.0 g, 45.1 mmol) is added over a period of 5 min. After 5 min, the ice bath is removed and the reaction mixture is stirred for 15 min at room temperature, and then quenched with 100 mL of 1 M-HCl. The aqueous layer is extracted with two 100 mL portions of dichloromethane, and the combined organic extracts are washed with 50 mL of brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to give 14.2 g of the crude product. Recrystallization from 500 mL of ethyl acetate/hexane (1:1) gives 13.00 g of N-(4-Methoxybenzyl)-2-nitrobenzenesulfonamide as white crystals (13.00 g, 90% yield).
To a 300 mL two-necked round-bottomed flask, 4-methoxybenzylamine (6.81 g, 49.6 mmol), 100 mL of dichloromethane and triethylamine (6.93 mL, 49.6 mmol) are added under nitrogen. The mixture is stirred and cooled with an ice bath while 2-nitrobenzenesulfonyl chloride (10.0 g, 45.1 mmol) is added over a period of 5 min. After 5 min, the ice bath is removed and the reaction mixture is stirred for 15 min at room temperature, and then quenched with 100 mL of 1 M-HCl. The aqueous layer is extracted with two 100 mL portions of dichloromethane, and the combined organic extracts are washed with 50 mL of brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to give 14.2 g of the crude product. Recrystallization from 500 mL of ethyl acetate/hexane (1:1) gives 13.00 g of N-(4-Methoxybenzyl)-2-nitrobenzenesulfonamide as white crystals (13.00 g, 90% yield).
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