Encyclopedia / Catalysts / Organic Intermediate / Pharmaceutical Intermediates

4-Fluorobenzenesulfonamide

CAS：402-46-0
MW:175.177
MF：C6H6FNO2S

4-Fluorobenzenesulfonamide, with the chemical formula C6H6FNO2S and CAS registry number 402-46-0, is a compound known for its applications in various chemical processes. This white solid, also referred to as 4-Fluorobenzenesulfonamide, is characterized by its fluorine and sulfonamide functional groups. It is commonly used as a building block in the synthesis of pharmaceuticals and agrochemicals, offering a versatile platform for the introduction of fluorine and sulfonamide moieties into different molecules. 4-Fluorobenzenesulfonamide has been studied for its potential antimicrobial and antitumor activities. It is important to note that the information provided here is based on the latest available data and may be subject to change as new research emerges.

View more+

Email Tweet Share

Names and ldentifier
Properties
Use and Manufacturing
Msds
NMR Spectrum
Other Information
Computational chemical data
Realated Product Infomation

1. Names and Identifiers

1.1 Name: 4-Fluorobenzenesulfonamide

1.2 Synonyms: 4-(fluoro)benzenesulfonamide; 4-FLOUROBENZENESULFONAMIDE; 4-fluorobenzene-1-sulfonaMide; 4-fluorobenzenesulphonamide; 4-fluorobenzensulfonamide; 4-fluorobenzesulfonamide; 4-fluorophenylsulfonamide; 4-FLUROBENZENESULFONAMIDE; Benzenesulfonamide, 4-fluoro-; Benzenesulfonamide, 4-fluoro- (9CI); Benzenesulfonamide, p-fluoro-; Benzenesulfonamide,p-fluoro; EINECS 206-946-2; MFCD00025384; p-fluoro-benzenesulfonamid; p-Fluorobenzenesulfonamide; p-Fluorobenzenesulfonamide (PFSA); p-fluorobenzenesulphonamide; p-fluorophenylsulfonamide;

View all

1.3 CAS No.: 402-46-0

1.4 CID: 120231

1.5 EINECS: 206-946-2

1.6 Molecular Formula: C6H6FNO2S

1.7 Inchi: InChI=1S/C6H6FNO2S/c7-5-1-3-6(4-2-5)11(8,9)10/h1-4H,(H2,8,9,10)

1.8 InChkey: LFLSATHZMYYIAQ-UHFFFAOYSA-N

1.9 Canonical Smiles: C1=CC(=CC=C1F)S(=O)(=O)N

1.10 Isomers Smiles: C1=CC(=CC=C1F)S(=O)(=O)N

2. Properties

2.1 Appearance: Not Available

2.2 Storage: Ambient temperatures.

2.3 pKa: 10.00±0.10(Predicted)

2.4 Water Solubility: It is soluble in water.

3. Use and Manufacturing

3.1 Description

4-Fluorobenzenesulfonamide, with the chemical formula C6H6FNO2S, has the CAS number 402-46-0. It appears as a white solid with no distinct odor. The basic structure of 4-Fluorobenzenesulfonamide consists of a benzene ring with a fluorine atom and a sulfonamide group attached to it. This compound is sparingly soluble in water. Safety information regarding 4-Fluorobenzenesulfonamide is not available.

Applicable Fields

Pharmaceuticals: 4-Fluorobenzenesulfonamide is used in the field of pharmaceuticals. Its purpose in this field may involve its role as an intermediate in the synthesis of various pharmaceutical compounds. The mechanism of action in pharmaceutical applications may vary depending on the specific compound being synthesized.

Storage

Conditions: Store in a cool and dry place.

View all

3.2 Methods of Manufacturing: 31. N-(4-fluorophenyl)sulfonyl-a-dehydrocyclohexylglycine.; 2-cyclohexyl-2-oxoethanoic acid (3.0 g, 19.2 mmol) was combined with p-toluenesulfonamide (2.70 g, 15.4 mmol) in toluene (21 mL) and diethyleneglycol diethyl ether (3 mL). MSA (0.10 mL, 1.5 mmol) was added, and this mixture was heated at reflux for 28h, then cooled to rt. The resulting solids were mixed with EtOAc (35 mL) and NaHC03 (2.6 g) in water (60 mL), until all materials dissolved. The aqueous was separated, and the organics were washed with NaH C03 (0.40 g) in water (10 mL). The combined aqueous layer was then washed with EtOAc (20 mL). The aqueous layer was cooled to 0 C, then treated with HCl (12.1 N, 3.1 mL). The resulting solids were filtered and washed with water and dried to give 3.0 g of crude material. The solids were then recrystallized from toluene/ methanol to give 2.8 g of white solid (58% yield). mp 214-215 C. 1H-NMR (400 MHz, CD30D) d 7.83-7.88 (m, 2H), 7.23-7.29 (m, 2H), 2.61-2.65 (m, 2H), 2.21-2.24 (m, 2H), 1.55-1.59 (m, 4H), 1.41-1.46 (m, 2H); 13C NMR (100 MHz, CD30D) 167.2, 166.3, 163.7, 155.3, 136.5 (2 peaks), 129.9 (2 peaks), 118.3, 115.5, 115.3, 31.0, 30.5, 27.6, 27.2, 25.7 ppm. HRMS calcd for C14H15FN04S (M-H) : 312.0706, Found: 312.0707.Example 10 27. N-(4-fluorobenzene)sulfonyl-alpha-dehydrovaline.; 3-methyl-2-oxobutyic acid, sodium salt (5.0 g, 36.2 mmol) was slurried in MTBE (25 mL) and cooled to 0 C, then HCI (12.1 N, 3.1 mL) was added. The resulting biphasic was warmed to rt, then saturated with Na2S04. The inorganic solids were filtered and washed with MTBE (25 mL). The combined organics were stripped to give a light-yellow oil. This oil was dissolved in toluene (35 mL) and diethyleneglycol diethyl ether (5 mL) and p-toluenesulfonamide (5.1 g, 29.0 mmol) then methanesulfonic acid (0.19 mL, 2.9 mmol) were added. The resulting mixture was heated at reflux with Dean-Stark removal of water for 24h, then cooled to 5 C. The resulting solid was filtered, and dried to give 5.4 g of crude material, which was recrystallized from MeOH/ water (16 mL/ 38 mL) to give 4.90 g of pure white solid (62% isolated yield). mp 172-173 C. IH-NMR (400 MHz, CD30D) d 7.83-7.86 (m, 2H), 7.22-7.27 (m, 2H), 2.12 (s, 3H), 1.87 (s, 3H); 13C NMR (100 MHz, CD30D) 166.6, 166.3, 163.7, 151.6, 136.7 (2 peaks), 129.9, 129.8, 120.8, 115.5, 115.3, 22.0, 20.4 ppm. HRMS calcd for C11H11FNO4S (M-H) : 272.0393, Found: 272.0398.[859] To a mixture of

View all

4. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 3

Acute toxicity - Dermal, Category 3

Skin irritation, Category 2

Eye irritation, Category 2

Acute toxicity - Inhalation, Category 3

Specific target organ toxicity \u2013 single exposure, Category 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H301+H311+H331 Toxic if swallowed, in contact with skin or if inhaled H315 Causes skin irritation H319 Causes serious eye irritation H335 May cause respiratory irritation
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P280 Wear protective gloves/protective clothing/eye protection/face protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area.
Response	P301+P310 IF SWALLOWED: Immediately call a POISON CENTER/doctor/\u2026 P321 Specific treatment (see ... on this label). P330 Rinse mouth. P302+P352 IF ON SKIN: Wash with plenty of water/... P312 Call a POISON CENTER/doctor/\u2026if you feel unwell. P361+P364 Take off immediately all contaminated clothing and wash it before reuse. P332+P313 If skin irritation occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P311 Call a POISON CENTER/doctor/\u2026
Storage	P405 Store locked up. P403+P233 Store in a well-ventilated place. Keep container tightly closed.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

View all

5. NMR Spectrum

13C NMR : Predict

1H NMR : Predict

Predict 1H proton NMR

6. Synthesis Route

402-46-0Total: 10 Synthesis Route

349-88-2 132 Suppliers

402-46-0 70 Suppliers

349-89-3

402-46-0 70 Suppliers

View all

7. Precursor and Product

precursor:

76-63-1

349-88-2

24850-33-7

349-89-3

29083-05-4

368-85-4

462-06-6

10493-33-1

product:

105899-98-7

312-52-7

3895-25-8

98996-94-2

371-42-6

1525-81-1

7062-49-9

727-36-6

501682-72-0

30059-39-3

8. Computed Properties

Molecular Weight：175.177g/mol
Molecular Formula：C₆H₆FNO₂S
Compound Is Canonicalized：True
XLogP3-AA：175.01032777
Monoisotopic Mass：175.01032777
Complexity：213
Rotatable Bond Count：1
Hydrogen Bond Donor Count：1
Hydrogen Bond Acceptor Count：4
Topological Polar Surface Area：68.5
Heavy Atom Count：：11
Defined Atom Stereocenter Count：0
Undefined Atom Stereocenter Count：0
Defined Bond Stereocenter Count：0
Undefined Bond Stereocenter Count：0
Isotope Atom Count：0
Covalently-Bonded Unit Count：1
CACTVS Substructure Key Fingerprint：AAADcYBiMQBAAAAAAAAAAAAAAAAAAAAAAAAwAAAAAAAAAAABAAAAGQQQQAAACACAUAgwAYAAAAKAACBCAHBCABAgAAAIiBgAAIgIICKAERCAIAAggAAIiAcAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

9.Other Information

Usage: 4-Fluorobenzenesulfonamide, is used to produce bis-(4-fluoro-benzenesulfonyl)-amine with 4-fluoro-benzenesulfonyl chloride at temperature of 55 - 60. This reaction will need reagent OH-.