Home Cart 0 Sign in  
X

[ CAS No. 3112-85-4 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 3112-85-4
Chemical Structure| 3112-85-4
Chemical Structure| 3112-85-4
Structure of 3112-85-4 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 3112-85-4 ]

Related Doc. of [ 3112-85-4 ]

Alternatived Products of [ 3112-85-4 ]

Product Details of [ 3112-85-4 ]

CAS No. :3112-85-4 MDL No. :MFCD00014741
Formula : C7H8O2S Boiling Point : -
Linear Structure Formula :- InChI Key :JCDWETOKTFWTHA-UHFFFAOYSA-N
M.W : 156.20 Pubchem ID :18369
Synonyms :

Calculated chemistry of [ 3112-85-4 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 39.54
TPSA : 42.52 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.9 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.26
Log Po/w (XLOGP3) : 0.5
Log Po/w (WLOGP) : 2.17
Log Po/w (MLOGP) : 1.51
Log Po/w (SILICOS-IT) : 1.12
Consensus Log Po/w : 1.31

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.5
Solubility : 4.92 mg/ml ; 0.0315 mol/l
Class : Very soluble
Log S (Ali) : -0.96
Solubility : 17.0 mg/ml ; 0.109 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.69
Solubility : 0.315 mg/ml ; 0.00202 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.63

Safety of [ 3112-85-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 3112-85-4 ]

* 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.

  • Upstream synthesis route of [ 3112-85-4 ]
  • Downstream synthetic route of [ 3112-85-4 ]

[ 3112-85-4 ] Synthesis Path-Upstream   1~14

  • 1
  • [ 3112-85-4 ]
  • [ 1521-51-3 ]
Reference: [1] Journal of Organic Chemistry, 1986, vol. 51, # 17, p. 3369 - 3371
  • 2
  • [ 3112-85-4 ]
  • [ 7726-95-6 ]
  • [ 74-83-9 ]
  • [ 108-86-1 ]
  • [ 583-53-9 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1911, vol. 30, p. 417
  • 3
  • [ 3112-85-4 ]
  • [ 814-49-3 ]
  • [ 56069-39-7 ]
Reference: [1] Journal of the American Chemical Society, 2011, vol. 133, # 13, p. 4702 - 4705
[2] Journal of the American Chemical Society, 2016, vol. 138, # 27, p. 8332 - 8335
[3] Journal of the Chemical Society - Perkin Transactions 1, 1998, # 24, p. 4097 - 4102
[4] Journal of the American Chemical Society, 2014, vol. 136, # 33, p. 11602 - 11605
  • 4
  • [ 3112-85-4 ]
  • [ 1805-32-9 ]
  • [ 2039-83-0 ]
Reference: [1] Chemical Communications, 2015, vol. 51, # 36, p. 7729 - 7732
  • 5
  • [ 100-68-5 ]
  • [ 3112-85-4 ]
  • [ 7205-98-3 ]
YieldReaction ConditionsOperation in experiment
87 %Chromat. With sodium hypochlorite pentahydrate In water; acetonitrile at 23 - 28℃; for 4 h; General procedure: 0.25 g (2 mmol) of thioanisole as a substrate, 10 mL of acetonitrile and 2 mL of water were placed in a 50 mL three-necked flask.The internal temperature of the flask was 23 ° C.0.79 g (4.8 mmol) of sodium hypochlorite pentahydrate crystals was added thereto at a time and stirred.The internal temperature of the flask rose to 28 ° C. and gradually decreased.GC analysis was carried out 3 hours after the start of the reaction, and 22percent of methyl phenyl sulfoxide,65percent of methyl phenyl sulfone was formed.As a by-product,6percent of chloromethyl phenyl sulfoxide,7percent of chloromethyl phenyl sulfone,A total of 0.8percent of higher order chlorides were observed.0.79 g (4.8 mmol) of sodium hypochlorite pentahydrate crystals was added and stirring was continued for 1 hour.Thioanisole,Methyl phenyl sulfoxide was completely disappeared and 87percent of methyl phenyl sulfone was formed.As impurities,11percent chloromethyl phenyl sulfone,0.5percent dichloromethyl phenyl sulfone,Production of trichloromethyl phenyl sulfone 1.3percent was observed.
Reference: [1] Patent: JP2017/52730, 2017, A, . Location in patent: Paragraph 0046
  • 6
  • [ 100-68-5 ]
  • [ 7205-94-9 ]
  • [ 1193-82-4 ]
  • [ 3112-85-4 ]
  • [ 7205-98-3 ]
YieldReaction ConditionsOperation in experiment
65 %Chromat. With sodium hypochlorite pentahydrate In water; acetonitrile at 23 - 28℃; for 3 h; General procedure: 0.25 g (2 mmol) of thioanisole as a substrate, 10 mL of acetonitrile and 2 mL of water were placed in a 50 mL three-necked flask.The internal temperature of the flask was 23 ° C.0.79 g (4.8 mmol) of sodium hypochlorite pentahydrate crystals was added thereto at a time and stirred.The internal temperature of the flask rose to 28 ° C. and gradually decreased.GC analysis was carried out 3 hours after the start of the reaction, and 22percent of methyl phenyl sulfoxide,65percent of methyl phenyl sulfone was formed.As a by-product,6percent of chloromethyl phenyl sulfoxide,7percent of chloromethyl phenyl sulfone,A total of 0.8percent of higher order chlorides were observed.0.79 g (4.8 mmol) of sodium hypochlorite pentahydrate crystals was added and stirring was continued for 1 hour.Thioanisole,Methyl phenyl sulfoxide was completely disappeared and 87percent of methyl phenyl sulfone was formed.As impurities,11percent chloromethyl phenyl sulfone,0.5percent dichloromethyl phenyl sulfone,Production of trichloromethyl phenyl sulfone 1.3percent was observed.
Reference: [1] Patent: JP2017/52730, 2017, A, . Location in patent: Paragraph 0046
  • 7
  • [ 3112-85-4 ]
  • [ 599-94-0 ]
  • [ 7205-98-3 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1987, # 3, p. 493 - 497
  • 8
  • [ 3112-85-4 ]
  • [ 657-46-5 ]
  • [ 654-47-7 ]
Reference: [1] Russian Journal of Organic Chemistry, 2002, vol. 38, # 10, p. 1462 - 1464
  • 9
  • [ 3112-85-4 ]
  • [ 657-46-5 ]
Reference: [1] Journal of the Chemical Society [Section] B: Physical Organic, 1969, p. 646 - 648
  • 10
  • [ 3112-85-4 ]
  • [ 5335-40-0 ]
YieldReaction ConditionsOperation in experiment
75% With chlorosulfonic acid In chlorosulfonic acid at 90℃; for 18 h; 3-Methanesulfonylbenzene-1-sulfonyl chloride
The intermediate 3-methanesulfonylbenzene-1-sulfonyl chloride was synthesized according to the methods disclosed in Park et al., J. Med. Chem. 51(21):6902-6915 (2008).
Specifically, methyl sulfonyl benzene (110 g, 0.7 mol) was heated for 18 hours at 90° C. in chlorosulfonic acid (450 mL, 6.7 mol) after which time the reaction mixture was allowed to cool to a temperature of about 21° C. before slowly being poured onto crushed ice.
The resulting slurry was twice extracted into EtOAc (2 L for each extraction).
The organic portions were combined and washed with brine (50 mL) before being dried over sodium sulfate, filtered and concentrated under reduced pressure to provide the intermediate sulfonyl chloride as an off white solid (125 g, yield 75percent).
1H NMR (400 MHz, CDCl3) δ ppm 8.61 (1 h, t, J=1.7 Hz), 8.35-8.31 (2H, m), 7.90 (1H, t, J=7.9 Hz), 3.15 (3H, s).
6.1% at 90℃; for 18 h; Methylsulfonylbenzene (5 g, 32 mmol) was placed into chlorosulfonic acid (37 g, 320 mmol), heated at 90 °Cfor 18 h, and cooled to room temperature. The mixture was slowly poured into crushed ice. The resulting suspensionwas extracted with ethyl acetate (2 3 200 mL). The organic layers were separated, combined, washed with saturatedaqueous NaCl solution (50 mL), and dried with sodium sulfate. After suction filtration, the resulting filtrate was distilledunder reduced pressure. The residue was the intermediate 3-methylsulfonylphenyl-1-sulfonyl chloride (50 mg, yield6.1percent).
Reference: [1] Patent: US2014/206769, 2014, A1, . Location in patent: Paragraph 0146
[2] Patent: EP3348548, 2018, A1, . Location in patent: Paragraph 0103
  • 11
  • [ 1193-82-4 ]
  • [ 3112-85-4 ]
  • [ 426-58-4 ]
  • [ 20808-12-2 ]
  • [ 1535-65-5 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1996, vol. 44, # 4, p. 703 - 708
[2] Chemical and Pharmaceutical Bulletin, 1996, vol. 44, # 4, p. 703 - 708
[3] Chemical and Pharmaceutical Bulletin, 1996, vol. 44, # 4, p. 703 - 708
[4] Chemical and Pharmaceutical Bulletin, 1996, vol. 44, # 4, p. 703 - 708
[5] Chemistry Letters, 1995, # 7, p. 581 - 582
  • 12
  • [ 3112-85-4 ]
  • [ 1535-65-5 ]
Reference: [1] Tetrahedron Letters, 2017, vol. 58, # 5, p. 396 - 400
  • 13
  • [ 3112-85-4 ]
  • [ 17025-47-7 ]
YieldReaction ConditionsOperation in experiment
72% at 75℃; for 5 h; General procedure: To a solution of NaOH (15percent w/w, 8 mL) cooled to 5 °C, Br2 (0.4 mL, 15 mmol, 3 equiv) was added dropwise while maintaining the temperature of the mixture below 10 °C. Next, the sulfone (5 mmol, 1 equiv) was added in one portion. The resulting mixture was stirred for the given time (Table 1) at 75 °C. The mixture was cooled to room temperature, and the precipitate filtered off, washed with H2O, dried in air, and crystallized from 2-PrOH. See Supplementary data for the characterization of the bromination products obtained
Reference: [1] Journal of Organic Chemistry, 1986, vol. 51, # 17, p. 3369 - 3371
[2] Tetrahedron Letters, 2012, vol. 53, # 48, p. 6606 - 6610,5
  • 14
  • [ 6704-31-0 ]
  • [ 3112-85-4 ]
  • [ 1221819-46-0 ]
YieldReaction ConditionsOperation in experiment
82%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.666667 h;
Stage #2: With diethyl chlorophosphate In tetrahydrofuran; hexane for 0.5 h;
Stage #3: at -78℃; for 2 h;
To a solution of (methylsulfonyl)benzene (2.2 g, 13.9 mmol) in THF (38 mL) at 0 was added n-BuLi (2.5 M in hexanes, 12.2 mL, 30.6 mmol) dropwise over 10 minutes. After the mixture was stirred for 30 min, chlorodiethylphosphonate (2.4 mL, 16.7 mmol) was added dropwise to the reaction. After 30 minutes, a solution of oxetan-3-one (1.0 g, 13.9 mmol) in THF (2 mL) was added dropwise to the reaction mixture at -78 . The reaction mixture was stirred at -78 for 2 hours, then diluted with aqueous NH4Cl (100 mL) and extracted with EtOAc (100 mL x 2) . The combined organic layers were concentrated and the residue was purified by silica gel chromatxography column (petroleum ether/EtOAc = 3/1) to give the title compound (2.4 g, 82percent) as a colorless oil. 1H NMR (400 MHz, CDCl3) : δ7.90-7.88 (m, 2H) , 7.68-7.64 (m, 1H) , 7.57 (t, J= 7.6 Hz, 2H) , 6.13-6.11 (m, 1H) , 5.66-5.64 (m, 2H) , 5.30-5.27 (m, 2H).
75%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.75 h; Inert atmosphere
Stage #2: With diethyl chlorophosphate In tetrahydrofuran; hexane at 0℃; for 0.5 h;
Stage #3: at -78℃; for 2 h;
3-((Phenylsulfonyl)methylene)oxetane
To an oven-dried vial was added (methylsulfonyl)benzene (0.570 g, 3.65 mmol) and the vial was evacuated with argon 3 times.
The dry THF (17 mL) was added and the reaction was cooled to 0° C. The 2.5 M BuLi in hexanes (3.21 mL, 8.03 mmol) was added dropwise and the reaction began to stir at 0° C. and stirred for 45 minutes.
The diethyl chlorophosphate (0.528 mL, 3.65 mmol) was then added at 0° C. and the reaction stirred for 30 minutes.
The reaction was then cooled to -78° C. and the oxetan-3-one (0.330 mL, 5.15 mmol) was then added dropwise and the reaction stirred for 2 h.
The reaction was then warmed to rt and filtered through a silica plug.
The reaction was then concentrated onto silica and purified by MPLC (20 min, 0-40percent EtOAc:hex) to provide pure 3-((phenylsulfonyl)methylene)oxetane (0.579 g, 2.75 mmol, 75percent yield).
1H NMR (400 MHz, CDCl3): δ 7.91-7.87 (m, 2H), 7.69-7.64 (m, 1H), 7.60-7.55 (m, 2H), 6.12 (quintet, J=2.3 Hz, 1H), 5.66-5.63 (m, 2H), 5.30-5.27 (m, 2H).
Reference: [1] Patent: WO2018/137619, 2018, A1, . Location in patent: Page/Page column 54; 55
[2] Journal of Medicinal Chemistry, 2010, vol. 53, # 8, p. 3227 - 3246
[3] Journal of Medicinal Chemistry, 2014, vol. 57, # 20, p. 8540 - 8562
[4] Patent: US2015/238473, 2015, A1, . Location in patent: Paragraph 0271
[5] Patent: WO2013/16197, 2013, A1, . Location in patent: Page/Page column 92
[6] Patent: WO2013/188856, 2013, A1, . Location in patent: Paragraph 0275
Same Skeleton Products
Historical Records

Similar Product of
[ 3112-85-4 ]

Chemical Structure| 125562-53-0

A1268001[ 125562-53-0 ]

(Methylsulfonyl)benzene-13C2

Reason: Stable Isotope

Related Functional Groups of
[ 3112-85-4 ]

Aryls

Chemical Structure| 5535-48-8

[ 5535-48-8 ]

(Vinylsulfonyl)benzene

Similarity: 0.98

Chemical Structure| 127-63-9

[ 127-63-9 ]

Sulfonyldibenzene

Similarity: 0.95

Chemical Structure| 3185-99-7

[ 3185-99-7 ]

1-Methyl-4-(methylsulfonyl)benzene

Similarity: 0.89

Chemical Structure| 1424-51-7

[ 1424-51-7 ]

3-(Phenylsulfonyl)acrylonitrile

Similarity: 0.87

Chemical Structure| 945-51-7

[ 945-51-7 ]

Sulfinyldibenzene

Similarity: 0.86

Sulfones

Chemical Structure| 5535-48-8

[ 5535-48-8 ]

(Vinylsulfonyl)benzene

Similarity: 0.98

Chemical Structure| 127-63-9

[ 127-63-9 ]

Sulfonyldibenzene

Similarity: 0.95

Chemical Structure| 3185-99-7

[ 3185-99-7 ]

1-Methyl-4-(methylsulfonyl)benzene

Similarity: 0.89

Chemical Structure| 1424-51-7

[ 1424-51-7 ]

3-(Phenylsulfonyl)acrylonitrile

Similarity: 0.87

Chemical Structure| 3406-02-8

[ 3406-02-8 ]

Bis(phenylsulfonyl)methane

Similarity: 0.83