Home Cart Sign in  
Chemical Structure| 5219-65-8 Chemical Structure| 5219-65-8

Structure of 5219-65-8

Chemical Structure| 5219-65-8

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 5219-65-8 ]

CAS No. :5219-65-8
Formula : C9H10O2S
M.W : 182.24
SMILES Code : O=C(O)CCSC1=CC=CC=C1
MDL No. :MFCD00215509
InChI Key :IGPROYLOGZTOAM-UHFFFAOYSA-N
Pubchem ID :222492

Safety of [ 5219-65-8 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P264-P302+P352-P304+P340-P305+P351+P338-P332+P313-P337+P313

Application In Synthesis of [ 5219-65-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 5219-65-8 ]

[ 5219-65-8 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 5219-65-8 ]
  • [ 3528-17-4 ]
YieldReaction ConditionsOperation in experiment
80% With sulfuric acid; at 110℃; for 4h; Add 3-phenylthiopropionic acid (13.54g, 74mmol) to 50ml of 80% concentrated sulfuric acid,Stir at 110 C for 4h.After cooling to room temperature, the reaction solution was poured into 100 ml of ice water, and extracted with 100 ml of ethyl acetate three times each time. The organic phases were combined, and the organic layer was washed with 100 ml of saturated NaHCO3 solution and 100 ml of water to neutrality, and the organic layer was anhydrous. Dried over sodium sulfate,The solvent was removed in vacuo to obtain 9.7 g of thiochroman-4-one,Yield was 80%.
60% With sulfuric acid; at 0 - 20℃; for 16h; General procedure: Intermediates 1a-c (65 mmol, 1a: 12 g, 1b: 13 g, 1c: 17 g)were added portion wise to 80 mL con. H2SO4 at 0C. Theblood-red colored solution was stirred overnight at rt. After completion of the reaction, which was monitored by TLC,the reaction mixture was poured on ice. The separated solid was filtered, dried under vacuum and recrystallized fromhexane to give intermediates 2a-c. 3.2.1. Thiochroman-4-one(2a)Off-white solid; mp 28-30C; yield 6.4 g (60%); 13CNMR (100 MHz, DMSOd6): δ 26.54 (C1), 39.45 (C2),124.89 (C3), 126.67 (C4), 129.02 (C5), 130.36 (C6), 133.47(C7), 141.0 (C8), 193.95 (C9); 1H NMR (400MHz, CDCl3):δ 2.96-3.00 (m, 2H, C1H); 3.22-3.26 (m, 2H, C2H); 7.15-7.19 (dt, J = 8.4& 1.2 Hz, 1H, C3H); 7.26-7.28 (dt, J = 8.4 &1.2 Hz, 1H, C4H); 7.35-7.39 (dt, J = 8.4 & 1.6 Hz, 1H,C5H); 8.09-8.12 (dt, J = 8.4 & 1.6 Hz, 1H, C6H); IR (KBr,υmax, cm-1): 3027, 2937, 2850, 1728, 1670, 1520, 1418, 1152,891, 826. Anal.Calcd for C9H8OS: C, 65.82; H, 4.91. Found:C, 65.78; H, 4.93.
With sulfuric acid; at 0 - 20℃; General procedure: To a mixture of acrylic acid (700 μL, 720mg, 10mmol) and 4-fluorothiophenol (1985 mg, 15 mmol) was added I2 (20% mol, 760 mg, 3 mmol) and the mixture was stirred at 50 C for 24 h. After completion of reaction (monitored by TLC), a cold saturated sodium thiosulfate solution (30 mL) was added and extracted with dichloromethane (2 x 25 mL); the combined organic layers were mixed with a saturated solution of sodium bicarbonate and extracted to remove the unreacted starting material. The aqueous layerwas acidifiedwith 10%HCl and extractedwith dichloromethane (3 x 50 mL). The combined organic layers were dried over Na2SO4, evaporation of the solvent under reduced pressure afforded 1150 mg (64%) of the desired addition product. The product was cooled down to 0 C in an ice bath and 3 mL of concentrated sulfuric acid was added and the reaction mixture was allowed to warm to room temperature for 2 h with magnetic stirring. The reaction was quenched with ice and the mixture was extracted with dichloromethane (3 x 50 mL). The combined organic layers were washed once with water, followed by saturated NaHCO3 solution. The combined organic layers were washed with brine, dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by column chromatography over silica gel using hexane/EtOAc (9:1) as eluent to give 570 mg (90%) of pure 2 as a yellow solid.
With sulfuric acid; at 0 - 20℃; for 0.12h; General procedure: 3-(phenylthio)propanoic acids B was added slowly to a 100 mL flask filled with 25 mL conc. H2SO4 at 0 C.Then the resultant mixture was warmed up to room temperature and stirred at room temperature forabout 12 hrs. When the reaction is finished as indicated by TLC monitoring, the reaction mixture waspoured onto ice and extracted with CH2Cl2 (3X 30 mL)upon warming up to room temperature. Theorganic layers were combined and dried over anhydrous Na2SO4. It was then filtered, and concentratedunder vacuum. The crude product was purified by flash column chromatography (EtOAc/hexanes, 10%)to afford thiochroman-4-one C in 60-80% yield.
With sulfuric acid; at 0 - 20℃; Thiochromone were prepared according to previously reported procedures.Thiophenols were purchased and used as received. A250 mL flask was fitted with astirrer bar and charged with 1M NaOH (50 mL) and 1M Na2CO3 (50 mL). A solutionof thiophenols S1 (100mmol) in 60 mL EtOH and 3-chloropropanoic acid (11 g, 102mmol) in 40 mL H2O were added respectively to the above solution. The reactionmixture was stirred at room temperature for 2 h, and then temperature increased toreflux. After the reaction was completed as determined by TLC and cooled down toroom temperature, EtOH was evaporated and then the aqueous phase was acidified topH 1~2 with conc. HCl. The solution was extracted with CH2Cl2 for three times andthe combined organic layers were dried over anhydrous Na2SO4, filtered, andconcentrated. The residue was purified by flash column chromatography(hexane/EtOAc, 20/1 to 5/1) to produce 3-(phenylthio)propanoic acid S2 in 85-95%yield
With sulfuric acid; at 2 - 20℃; for 2h; General procedure: To a mixture of acrylic acid (700 mL, 720 mg, 10 mmol)and thiophenol or phenol (15 mmol), I2 (20% mol, 760 mg,3 mmol) was added, and the mixture was stirred at 50 C for24 h. After the completion of the reaction (monitored byTLC), a cold saturated sodium thiosulfate solution (30 mL)was added and extracted with dichloromethane (2 × 25 mL).The combined organic layers were mixed with a saturatedsolution of sodium bicarbonate and extracted to remove theunreacted starting material layer, which was acidified with10% HCl and extracted with dichloromethane (3 × 50 mL).The combined organic layers were dried over Na2SO4, andthe evaporation of the solvent under reduced pressureafforded 64-66% of the desired additional product. Theproduct was cooled down to 2 C in an ice bath, 3 mL ofconcentrated sulfuric acid was added, and the reactionmixture was allowed to warm to room temperature for 2 h,with magnetic stirring. The reaction was quenched with ice,and the mixture was extracted with dichloromethane (3 ×50 mL). The combined organic layers were washed oncewith water, and then with saturated NaHCO3 solution. Thecombined organic layers were washed with brine, dried overNa2SO4, and concentrated under reduced pressure. Theresidue was purified by column chromatography over silicagel using hexane/EtOAc (9:1), as an eluent, to obtainthiochroman-4-one or 4-chromanone, as a white solid(90-85%).

 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 5219-65-8 ]

Aryls

Chemical Structure| 1141-45-3

A274970 [1141-45-3]

3-(Naphthalen-2-ylthio)propanoic acid

Similarity: 0.95

Chemical Structure| 10446-72-7

A571101 [10446-72-7]

3-(Naphthalen-1-ylthio)propanoic acid

Similarity: 0.92

Chemical Structure| 10446-72-7

A571101 [10446-72-7]

3-(Naphthalen-1-ylthio)propanoic acid

Similarity: 0.92

Chemical Structure| 10446-72-7

A571101 [10446-72-7]

3-(Naphthalen-1-ylthio)propanoic acid

Similarity: 0.92

Chemical Structure| 13739-35-0

A952937 [13739-35-0]

3-(p-Tolylthio)propanoic acid

Similarity: 0.90

Carboxylic Acids

Chemical Structure| 1141-45-3

A274970 [1141-45-3]

3-(Naphthalen-2-ylthio)propanoic acid

Similarity: 0.95

Chemical Structure| 10446-72-7

A571101 [10446-72-7]

3-(Naphthalen-1-ylthio)propanoic acid

Similarity: 0.92

Chemical Structure| 10446-72-7

A571101 [10446-72-7]

3-(Naphthalen-1-ylthio)propanoic acid

Similarity: 0.92

Chemical Structure| 13739-35-0

A952937 [13739-35-0]

3-(p-Tolylthio)propanoic acid

Similarity: 0.90

Chemical Structure| 880-13-7

A796305 [880-13-7]

3-(Phenylthio)butanoic acid

Similarity: 0.88

Sulfides

Chemical Structure| 1141-45-3

A274970 [1141-45-3]

3-(Naphthalen-2-ylthio)propanoic acid

Similarity: 0.95

Chemical Structure| 10446-72-7

A571101 [10446-72-7]

3-(Naphthalen-1-ylthio)propanoic acid

Similarity: 0.92

Chemical Structure| 10446-72-7

A571101 [10446-72-7]

3-(Naphthalen-1-ylthio)propanoic acid

Similarity: 0.92

Chemical Structure| 10446-72-7

A571101 [10446-72-7]

3-(Naphthalen-1-ylthio)propanoic acid

Similarity: 0.92

Chemical Structure| 10446-72-7

A571101 [10446-72-7]

3-(Naphthalen-1-ylthio)propanoic acid

Similarity: 0.92