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N-Acetylsulfanilyl chloride

Basic information Safety Supplier Related

N-Acetylsulfanilyl chloride Basic information

Product Name:
N-Acetylsulfanilyl chloride
Synonyms:
  • ASC
  • 4-ACETYLAMINO BENZENESULFONYL CHLORIDE
  • 4-ACETAMIDOPHENYLSULFONYL CHLORIDE
  • 4-ACETAMIDOBENZENESULFONYL CHLORIDE
  • 4-ACETAMIDOBENZENESULPHONYL CHLORIDE
  • -(acetylamino)benzenesulfonylchloride
  • 4-(acetylamino)-benzenesulfonylchlorid
  • 4'-(Chlorosulfonyl)acetanilide
CAS:
121-60-8
MF:
C8H8ClNO3S
MW:
233.67
EINECS:
204-485-1
Product Categories:
  • Amines
  • Aromatics
  • Sulfonyl Chlorides
  • Sulfur & Selenium Compounds
Mol File:
121-60-8.mol
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N-Acetylsulfanilyl chloride Chemical Properties

Melting point:
142-145 °C (dec.)(lit.)
Boiling point:
426.8±28.0 °C(Predicted)
Density 
1.2977 (rough estimate)
refractive index 
1.6300 (estimate)
storage temp. 
-20°C
pka
13.75±0.70(Predicted)
form 
Granular Crystalline Powder or Crystals
color 
White to cream-beige
Water Solubility 
SLIGHTLY SOLUBLE
Sensitive 
Moisture Sensitive
Merck 
14,103
BRN 
746676
CAS DataBase Reference
121-60-8(CAS DataBase Reference)
NIST Chemistry Reference
P-acetamidobenzene sulfonyl chloride(121-60-8)
EPA Substance Registry System
Benzenesulfonyl chloride, 4-(acetylamino)- (121-60-8)
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Safety Information

Hazard Codes 
C
Risk Statements 
22-34-37
Safety Statements 
26-36/37/39-45-28B
RIDADR 
UN 3261 8/PG 2
WGK Germany 
3
RTECS 
DB8837500
9-21
TSCA 
Yes
HazardClass 
8
PackingGroup 
II
HS Code 
29242995
Hazardous Substances Data
121-60-8(Hazardous Substances Data)
Toxicity
LD50 oral in rat: > 3200mg/kg

MSDS

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N-Acetylsulfanilyl chloride Usage And Synthesis

Chemical Properties

OFF-WHITE TO SLIGHTLY GREY GRANULAR CRYST. POWDER

Uses

A sulfanilamide derivative of Chitosan

Uses

Intermediate in the preparation of sulfanilamide and its derivatives.

Biotechnological Production

After more than three decades of strain and process optimization, the 2KGA fermentation by K. vulgare has reached a performance level that makes it increasingly difficult to achieve further cost-relevant improvements. Instead, opportunities can be seen in the succeeding step of 2KGA rearrangement to ascorbic acid, which still follows the same concept as laid out in the 1930s by Reichstein and Grüssner. This chemical step contributes significantly to the overall process costs. A process Industrial Production of L-Ascorbic Acid (Vitamin C) and D-Isoascorbic Acid 171 concept that could convert sorbitol directly to ascorbic acid would therefore be most attractive. In theory, this could build on the established 2KGA fermentation with an enzyme-catalyzed 2KGA to Asc rearrangement (2,6-hemiacetal to 1,4- lactone) as extension. Ab initio energy calculations as well as experimental results (own unpublished results) indicate that in aqueous environment, Asc is thermodynamically far more stable than 2KGA and (nearly) quantitative conversion should be possible. However, no enzyme efficiently catalyzing this reaction has so far been identified. The few publications of enzyme catalysis for this reaction so far shows only trace activity and no significant improvements have been reported. 2KGA may represent a kinetic trap in an aqueous environment and biotechnological reaction pathways all the way to Asc may need to avoid 2KGA. Accordingly, 2KGA is also not part of natural biosynthetic routes, where Asc formation directly results from the oxidation of precursor molecules with appropriately preformed 1,4-lactone linkage (L-gulono-1,4-lactone in animals, L-galactono-1,4-lactone in plants). Enzymes converting L-gulono-1,4-lactone to Asc are also known from bacteria, even from Ketogulonicigenium. The biochemical description of the Ketogulonicigenium enzyme indicates that it belongs to the family of heterotrimeric periplasmic flavohemoproteins, of which several can be found in the published Ketogulonicigenium genomes. Besides sharing the same FAD cofactor, these enzymes bear no similarity to the mammalian gulono-1,4- lactone dehydrogenase. The use of these natural or nature-like Asc-forming enzymatic steps in biotechnological production processes is so far precluded by the rare nature of these L-sugar-derived lactone precursor molecules and the lack of efficient production methods for these compounds. It was, therefore, a tantalizing discovery when Asc formation directly from L-sorbosone, the intermediate of the efficient 2KGA formation route, was identified in those two species already in the focus for 2KGA production for decades: K. vulgare and G. oxydans. Besides an earlier report of L-sorbosone to Asc activity derived from plant tissue , which did not see consolidating follow-ups, the above observations are the first evidence of biological Asc formation from a molecule other than a 1,4-lactone.

Safety Profile

A poison by intraperitoneal route.Moderately toxic by ingestion. When heated todecomposition it emits toxic vapors of NOx, SOx, and Cl.

Purification Methods

Crystallise the chloride from toluene, CHCl3, or ethylene dichloride. [Beilstein 14 IV 2703.]

N-Acetylsulfanilyl chlorideSupplier

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