5-(Chlorosulphonyl)-2-fluorobenzoic acid
- Product Name
- 5-(Chlorosulphonyl)-2-fluorobenzoic acid
- CAS No.
- 37098-75-2
- Chemical Name
- 5-(Chlorosulphonyl)-2-fluorobenzoic acid
- Synonyms
- 2-Fluoro-5-(chlorosulfonyl)benzoic acid;5-(Chlorosulphonyl)-2-fluorobenzoic acid;5-Chlorosulfonyl-2-fluorobenzoicacid,97%;Benzoic acid, 5-(chlorosulfonyl)-2-fluoro-;3-Carboxy-4-fluorobenzenesulphonyl chloride
- CBNumber
- CB51261917
- Molecular Formula
- C7H4ClFO4S
- Formula Weight
- 238.62
- MOL File
- 37098-75-2.mol
5-(Chlorosulphonyl)-2-fluorobenzoic acid Property
- Melting point:
- 111-113℃
- Boiling point:
- 404.0±30.0 °C(Predicted)
- Density
- 1.670
- storage temp.
- under inert gas (nitrogen or Argon) at 2-8°C
- pka
- 2.07±0.10(Predicted)
- form
- Crystalline Powder
- color
- White to off-white
- Sensitive
- Moisture Sensitive
Safety
- RIDADR
- UN3261
- HazardClass
- 8
- HS Code
- 2916399090
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Danger
- Hazard statements
-
H314Causes severe skin burns and eye damage
H318Causes serious eye damage
- Precautionary statements
-
P301+P330+P331IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P405Store locked up.
N-Bromosuccinimide Price
- Product number
- C384973
- Product name
- 5-(Chlorosulfonyl)-2-fluorobenzoicacid
- Packaging
- 500mg
- Price
- $45
- Updated
- 2021/12/16
- Product number
- C384973
- Product name
- 5-(Chlorosulfonyl)-2-fluorobenzoicacid
- Packaging
- 5g
- Price
- $75
- Updated
- 2021/12/16
- Product number
- 082235
- Product name
- 5-(Chlorosulfonyl)-2-fluorobenzoic acid
- Purity
- 97%
- Packaging
- 10g
- Price
- $656
- Updated
- 2021/12/16
- Product number
- HCH0006065
- Product name
- 5-(CHLOROSULPHONYL)-2-FLUOROBENZOIC ACID
- Purity
- 95.00%
- Packaging
- 1G
- Price
- $721.57
- Updated
- 2021/12/16
- Product number
- HCH0006065
- Product name
- 5-(CHLOROSULPHONYL)-2-FLUOROBENZOIC ACID
- Purity
- 95.00%
- Packaging
- 2.5G
- Price
- $983.88
- Updated
- 2021/12/16
5-(Chlorosulphonyl)-2-fluorobenzoic acid Chemical Properties,Usage,Production
Synthesis
445-29-4
37098-75-2
1. O-fluorobenzoic acid (10.0 g, 71.4 mmol) was slowly added to chlorosulfonic acid (50 mL) at 0 °C and kept stirring at 0 °C for 1 hour. Once the reaction was complete, the mixture was slowly poured into ice water. The precipitate formed was collected by filtration, washed with water (3 x 100 mL) and dried under vacuum overnight to give 5-(chlorosulfonyl)-2-fluorobenzoic acid (10.5 g, 44.0 mmol) as a brown solid. 2. 5-(Chlorosulfonyl)-2-fluorobenzoic acid (10.0 g, 41.9 mmol) was dissolved in 60 mL of SOCl2 and refluxed for 1.5 hours. After evaporation to remove the SOCl2, the residue was dissolved in toluene (150 mL) and 3,4-difluoroaniline (6.5 g, 50.3 mmol) was added. The mixture was stirred at 100 °C for 4 h. After cooling to room temperature, the mixture was poured into saturated ammonium chloride solution (200 mL) and extracted with EtOAc (3 x 200 mL). The organic layers were combined, dried over sodium sulfate and concentrated in vacuum. Purification by fast chromatography (hexane/EtOAc = 6:4 v/v) afforded 3-((3,4-difluorophenyl)carbamoyl)-4-fluorobenzene-1-sulfonyl chloride (92% yield, 13.51 g, 38.6 mmol). 3. To a solution of 3-((3,4-difluorophenyl)carbamoyl)-4-fluorobenzene-1-sulfonyl chloride (10.0 g, 28.6 mmol) in CH2Cl2 (200 mL) was added alkynylpropylamine hydrochloride (3.1 g, 34.3 mmol) and Et3N (7.8 mL, 57.2 mmol) at 0 °C. After stirring at room temperature overnight, the solution was poured into saturated ammonium chloride solution (250 mL) and extracted with CH2Cl2 (3 x 100 mL). The organic layers were combined, dried over sodium sulfate and concentrated in vacuum. The resulting solid was washed with ether (50 mL) and hexane (50 mL) to afford N-(3,4-difluorophenyl)-2-fluoro-5-(N-(prop-2-yn-1-yl)aminosulfonyl)benzamide (74% yield, 7.8 g, 21.1 mmol) as a white powder. 4. An aqueous (1 mL) solution of bromocyclopropane (0.6 mL, 4.9 mmol) and sodium azide (483 mg, 7.4 mmol) was heated at 120 °C for 30 min under microwave radiation. Acetonitrile (1 mL) solution of compound 12 (0.1 g, 0.3 mmol), sodium ascorbate (10 mg, 0.05 mmol) and copper sulfate (20 mg, 0.12 mmol) were added. The mixture was heated at 80°C under microwave radiation for 30 min, poured into saturated ammonium chloride solution (50 mL) and extracted with EtOAc (3 x 50 mL). The organic layers were combined, dried with sodium sulfate and concentrated in vacuum. Purification by fast chromatography (hexane:EtOAc = 6:4 v/v) afforded compound 13 (19% yield, 23 mg, 0.05 mmol) as a white powder. 5. 1H NMR (400 MHz, acetone-d6) δ 9.92 (s, 1H), 8.25 (dd, J = 6.6,2.5 Hz, 1H), 8.06-7.95 (m, 2H), 7.77 (s, 1H), 7.58-7.52 (m, 1H), 7.48 (dd, J = 10.1,8.7 Hz, 1H) for compound 13 , 7.37 (dt, J = 10.6,9.0 Hz, 1H), 7.21 (brs, 1H), 6.11-5.94 (m, 1H), 5.32-5.16 (m, 1H), 4.99 (dt, J = 6.0,1.5 Hz, 2H), 4.32 (s, 2H).13C NMR (101 MHz, acetone-d6) δ 188.9,167.9,162.1,150.2,149.2 (d, J = 12.9 Hz), 146.8 (d, J = 13.0 Hz), 142.8,137.9 (d, J = 5.9 Hz), 128.5,124.6,120.4-118.2 (m), 117.5 (dd, J = 6.0,3.6Hz ), 110.6 (d, J = 22.1 Hz), 81.5,73.3,33.2,29.7,12.8 (d, J = 9.6 Hz).19F NMR (377 MHz, acetone-d6) δ-110.6 (s), -139.6-139.7 (m), -146.1-146.3 (m).HRMS (ESI): C19H17F3N5O3S m/z [M + H]+ Calculated value: 452.1004, measured value: 452.0999.
References
[1] Patent: US6207829, 2001, B1
[2] European Journal of Medicinal Chemistry, 2017, vol. 138, p. 407 - 421
[3] Journal of Medicinal Chemistry, 2010, vol. 53, # 12, p. 4603 - 4614
[4] Patent: US2008/221327, 2008, A1. Location in patent: Page/Page column 4-5
[5] Patent: CN105712952, 2016, A. Location in patent: Paragraph 0346; 0347; 0348
5-(Chlorosulphonyl)-2-fluorobenzoic acid Preparation Products And Raw materials
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View Lastest Price from 5-(Chlorosulphonyl)-2-fluorobenzoic acid manufacturers
- Product
- 5-(Chlorosulphonyl)-2-fluorobenzoic acid 37098-75-2
- Price
- US $10.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 10 mt
- Release date
- 2024-12-09
- Product
- 5-(Chlorosulphonyl)-2-fluorobenzoic acid 37098-75-2
- Price
- US $0.00-0.00/KG
- Min. Order
- 5mg
- Purity
- 99%HPLC
- Supply Ability
- 2000tons
- Release date
- 2020-01-07
- Product
- 5-(Chlorosulphonyl)-2-fluorobenzoic acid 37098-75-2
- Price
- US $1.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 100KG
- Release date
- 2020-01-08