Home Cart 0 Sign in  
X

[ CAS No. 67137-56-8 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 67137-56-8
Chemical Structure| 67137-56-8
Chemical Structure| 67137-56-8
Structure of 67137-56-8 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

* Shipping: {[proInfo.prShipping]}

Quality Control of [ 67137-56-8 ]

Related Doc. of [ 67137-56-8 ]

Alternatived Products of [ 67137-56-8 ]
Product Citations

Product Details of [ 67137-56-8 ]

CAS No. :67137-56-8 MDL No. :MFCD19354070
Formula : C7H7BrO2S Boiling Point : -
Linear Structure Formula :- InChI Key :KEYPHZZYKZVXLU-UHFFFAOYSA-N
M.W : 235.10 Pubchem ID :12403315
Synonyms :

Calculated chemistry of [ 67137-56-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.29
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 47.88
TPSA : 54.54 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.99 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.39
Log Po/w (XLOGP3) : 2.45
Log Po/w (WLOGP) : 2.23
Log Po/w (MLOGP) : 1.75
Log Po/w (SILICOS-IT) : 3.36
Consensus Log Po/w : 2.43

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.98
Solubility : 0.246 mg/ml ; 0.00105 mol/l
Class : Soluble
Log S (Ali) : -3.24
Solubility : 0.136 mg/ml ; 0.000577 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.01
Solubility : 0.231 mg/ml ; 0.000984 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.43

Safety of [ 67137-56-8 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 67137-56-8 ]

* 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 [ 67137-56-8 ]

[ 67137-56-8 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 19432-68-9 ]
  • [ 67137-56-8 ]
YieldReaction ConditionsOperation in experiment
81% With N-Bromosuccinimide; acetic acid; In chloroform; at 20℃; for 72h; SCHEME 7Step 1: (The following reaction is carried out in an anhydrous N2 atmosphere.) Dissolve thiophene-2-yl-acetic acid methyl ester (42) (2.0 g, 12.8 mmol) in anhydrous chloroform (9.0 mL) and glacial acetic acid (9.0 mL), add iV-bromosuccinimide (2.3 g, 13.0 mmol) in portions and stir the mixture for 3 d at rt. Add water to the reaction mixture, separate layers and extract the aqu. layer with dichloromethane. Wash combined organic layer several times with a 1 M aqu. NaOH and water and once with brine and dry it with Na2SO4. Purify the crude product by preparative radial chromatography (CyH/EtOAc 5+1] to obtain (5- bromo-thiophen-2-yl)-acetic acid methyl ester (43) as a yellow oil (2.46 g, 81%) which is used without any further purification. 1H NMR (400 MHz, CDCl3): 3.71 (s, 3 H); 3.75 (s, 2 H); 6.67 (d, 1 H, J= 3.8 Hz); 6.88 (d, 1 H, J= 3.8 Hz).
81% With N-Bromosuccinimide; In chloroform; acetic acid; at 20℃; for 72h; Step 1: (The following reaction is carried out in an anhydrous N2 atmosphere.) Dissolve thiophene-2-yl-acetic acid methyl ester (42) (2.0 g, 12.8 mmol) in anhydrous chloroform (9.0 mL) and glacial acetic acid (9.0 mL), add N-bromosuccinimide (2.3 g, 13.0 mmol) in portions and stir the mixture for 3 d at rt. Add water to the reaction mixture, separate layers and extract the aqu. layer with dichloromethane. Wash combined organic layer several times with a 1 M aqu. NaOH and water and once with brine and dry it with Na2SO4. Purify the crude product by preparative radial chromatography (CyH/EtOAc 5+1] to obtain (5-bromo-thiophen-2-yl)-acetic acid methyl ester (43) as a yellow oil (2.46 g, 81%) which is used without any further purification. 1H NMR (400 MHz, CDCl3): 3.71 (s, 3H); 3.75 (s, 2H); 6.67 (d, 1H, J=3.8 Hz); 6.88 (d, 1H, J=3.8 Hz).
80% With bromine; In dichloromethane; at 0℃; for 0.5h; Acetyl chloride (2.43 ml, 34.1 mmol) was added to a solution of the 2-thiopheneacetic acid (1.94 g, 13.7 mmol) in MeOH (100 ml) at 0C. The reaction was then stirred at r.t. over night and the solvent was removed in vacuo. The crude material was dissolved in Et20 (-50 ml) and washed with diluted K2CO3. The organic phase was dried over MgS04 and removed in vacuo. Yield: 1.81g (85%). LC-MS: m/z = 174 (M + 1). Br2 (0.333 ml, 6.47 mmol) in DCM (3 ml) was added to a solution of the ester from above (1.01 g, 6.47 mmol) in DCM (20 ml) at 0C. The reaction was stirred at this temp for 30 min. DCM (-10 ml) was added and the mixture was washed with saturated Na2S203 and diluted Na2C03. The organic phase was dried over MgS04 and removed in vacuo. The crude product was dissolved in DCM and run though a plug of silica with 5% EtOAc in iso-hexane as eluent. Yield: 1.21 g (80%) as a pale yellow oil. ¾ NMR (400 MHz, CDC13): delta 3.74 (s, 3H), 3.78 (s, 2H), 6.70 (d, J 3.8 Hz, 1H), 6.91 (d, J 3.8 Hz, 1H). Argon was bubbled through a stirred mixture of bromide from above (274 mg, 1.16 mmol), 2,5- thiopenediboronic acid (80 mg, 0.466 mmol), KF (162 mg, 2.79 mmol), MeOH (3 ml) and toluene (3 ml) for 10 min. PEPPSI-iPr(13.6 mg, 0.019 mmol) was added and the reaction was heated at 55C for 3 hours. The mixture was concentrated and added water and DCM (~4 ml). The DCM mixture was purified by flash chromatography (2.5% EtOAc in toluene, 12g Redisep silica). The solid was dissolved in dioxane (2 ml) and water (1 ml) and 1 M NaOH (0,600 ml) were added. The reaction was heated at 75C for 30 min. The solvents were removed in vacuo and the crude was dissolved in water with some NH4HCO3. The mixture was filtered and purified by prep-HPLC (5-40% MeCN, in 50 mM NH3/NH4HCO3 buffer). The combined pure fractions were concentrated to dryness. Water and HCl were added and the mixture extracted with EtOAc. The organic phase was dried over MgS04 and removed in vacuo. Yield: 30 mg (52%) as a pale yellow solid. 1H NMR (400 MHz, DMSO-i/6): delta 3.84 (s, 4H), 6.91 (d, J3.5 Hz, 2H), 7.16 (d, J3.5 Hz, 2H), 7.20 (s, 2H), 12.63 (br. s., 2H). HPLC: Rt = 1.48 min, 100% (254 nm, 10-40% MeCN in 10 mM buffer, XBndge) and Rt = 1.45 min, 100% (400 nm, 10-40% MeCN in 10 mM buffer, XBndge). LC-MS: m/z = 365 (M + 1).
80% With bromine; In dichloromethane; at 0℃; for 0.5h; Br2 (0.333 ml, 6.47 mmol) in DCM (3 ml) was added to a solution of the ester from above (1.01 g, 6.47 mmol) in DCM (20 ml) at 0C. The reaction was stirred at this temp for 30 min. DCM (-10 ml) was added and the mixture was washed with saturated Na2S203 and diluted Na2C03. The organic phase was dried over MgS04 and removed in vacuo. The crude product was dissolved in DCM and run though a plug of silica with 5% EtOAc in iso-hexane as eluent. Yield: 1.21 g (80%) as a pale yellow oil. 1H NMR (400 MHz, CDC13): delta 3.74 (s, 3H), 3.78 (s, 2H), 6.70 (d, J 3.8 Hz, 1H), 6.91 (d, J3.8 Hz, 1H).

  • 2
  • [ 67137-56-8 ]
  • [ 171364-83-3 ]
  • [ 934176-66-6 ]
  • 3
  • Thiophene acetic acid [ No CAS ]
  • [ 19432-68-9 ]
  • [ 67137-56-8 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid; In methanol; Methyl 2-(thiophen-2-yl)acetate. Thiophene acetic acid (27.3 g, 192 mmol) was treated with a solution of H2SO4 (5.76 mL, 108 mmol) in MeOH (384 mL) at reflux for one hour. The reaction was then cooled to room temperature, concentrated by rotovap, diluted with ether, washed with 5% sodium bicarbonate and brine. The organic phase was then dried with magnesium sulfate and concentrated by rotovap to yield the product as a yellow oil (27.4 g, 176 mmol, 91%), which was used without further purification. The product matches data for commercially available methyl 2-(thiophen-2-yl)acetate (CAS No. 19432-68-9). Methyl 2-(5-bromothiophen-2-yl)acetate (D).
  • 4
  • [ 67137-56-8 ]
  • [ 26076-46-0 ]
  • [ 1235583-29-5 ]
YieldReaction ConditionsOperation in experiment
With potassium fluoride; [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride; In methanol; toluene; at 55℃; for 3h;Inert atmosphere; Acetyl chloride (2.43 ml, 34.1 mmol) was added to a solution of the 2-thiopheneacetic acid (1.94 g, 13.7 mmol) in MeOH (100 ml) at 0°C. The reaction was then stirred at r.t. over night and the solvent was removed in vacuo. The crude material was dissolved in Et20 (-50 ml) and washed with diluted K2CO3. The organic phase was dried over MgS04 and removed in vacuo. Yield: 1.81g (85percent). LC-MS: m/z = 174 (M + 1). Br2 (0.333 ml, 6.47 mmol) in DCM (3 ml) was added to a solution of the ester from above (1.01 g, 6.47 mmol) in DCM (20 ml) at 0°C. The reaction was stirred at this temp for 30 min. DCM (-10 ml) was added and the mixture was washed with saturated Na2S203 and diluted Na2C03. The organic phase was dried over MgS04 and removed in vacuo. The crude product was dissolved in DCM and run though a plug of silica with 5percent EtOAc in iso-hexane as eluent. Yield: 1.21 g (80percent) as a pale yellow oil. ¾ NMR (400 MHz, CDC13): delta 3.74 (s, 3H), 3.78 (s, 2H), 6.70 (d, J 3.8 Hz, 1H), 6.91 (d, J 3.8 Hz, 1H). Argon was bubbled through a stirred mixture of bromide from above (274 mg, 1.16 mmol), 2,5- thiopenediboronic acid (80 mg, 0.466 mmol), KF (162 mg, 2.79 mmol), MeOH (3 ml) and toluene (3 ml) for 10 min. PEPPSI-iPr?(13.6 mg, 0.019 mmol) was added and the reaction was heated at 55°C for 3 hours. The mixture was concentrated and added water and DCM (~4 ml). The DCM mixture was purified by flash chromatography (2.5percent EtOAc in toluene, 12g Redisep silica). The solid was dissolved in dioxane (2 ml) and water (1 ml) and 1 M NaOH (0,600 ml) were added. The reaction was heated at 75°C for 30 min. The solvents were removed in vacuo and the crude was dissolved in water with some NH4HCO3. The mixture was filtered and purified by prep-HPLC (5-40percent MeCN, in 50 mM NH3/NH4HCO3 buffer). The combined pure fractions were concentrated to dryness. Water and HCl were added and the mixture extracted with EtOAc. The organic phase was dried over MgS04 and removed in vacuo. Yield: 30 mg (52percent) as a pale yellow solid. 1H NMR (400 MHz, DMSO-i/6): delta 3.84 (s, 4H), 6.91 (d, J3.5 Hz, 2H), 7.16 (d, J3.5 Hz, 2H), 7.20 (s, 2H), 12.63 (br. s., 2H). HPLC: Rt = 1.48 min, 100percent (254 nm, 10-40percent MeCN in 10 mM buffer, XBndge) and Rt = 1.45 min, 100percent (400 nm, 10-40percent MeCN in 10 mM buffer, XBndge). LC-MS: m/z = 365 (M + 1).
With potassium fluoride; [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride; In methanol; toluene; at 55℃; for 3.16667h;Inert atmosphere; Argon was bubbled through a stirred mixture of bromide from above (274 mg, 1.16 mmol), 2,5-thiopenediboronic acid (80 mg, 0.466 mmol), KF (162 mg, 2.79 mmol), MeOH (3 ml) and toluene (3 ml) for 10 min. PEPPSI-iPr?(13.6 mg, 0.019 mmol) was added and the reaction was heated at 55°C for 3 hours. The mixture was concentrated and added water and DCM (~4 ml). The DCM mixture was purified by flash chromatography (2.5percent EtOAc in toluene, 12g Redisep silica). The solid was dissolved in dioxane (2 ml) and water (1 ml) and 1 M NaOH (0,600 ml) were added. The reaction was heated at 75°C for 30 min. The solvents were removed in vacuo and the crude was dissolved in water with some H4HCO3. The mixture was filtered and purified by prep-HPLC (5-40percent MeCN, in 50 mM H3/NH4HCO3 buffer). The combined pure fractions were concentrated to dryness. Water and HC1 were added and the mixture extracted with EtOAc. The organic phase was dried over MgS04 and removed in vacuo. Yield: 30 mg (52percent) as a pale yellow solid. 1H NMR (400 MHz, DMSO- d6): delta 3.84 (s, 4H), 6.91 (d, J3.5 Hz, 2H), 7.16 (d, J3.5 Hz, 2H), 7.20 (s, 2H), 12.63 (br. s., 2H). HPLC: Rt = 1.48 min, 100percent (254 nm, 10-40percent MeCN in 10 mM buffer, XBridge) and Rt = 1.45 min, 100percent (400 nm, 10-40percent MeCN in 10 mM buffer, XBridge). LC-MS: m/z = 365 (M + 1).
  • 5
  • [ 67137-56-8 ]
  • [ 103986-53-4 ]
  • methyl 2-[5-(4-methylnaphthalen-1-yl)thiophen-2-yl]acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% With potassium carbonate; bis(dibenzylideneacetone)-palladium(0); In ethanol; water; at 50℃; In a 100 ml three-neck flask, compound 3''' (12 mmol, 2.23 g) and methyl 2-(5-bromothiophen-2-yl)acetate (10 mmol, 2.35 g), potassium carbonate (10 mmol, 1.38 g), 50 ml of an 80% aqueous solution of ethanol, Pd(dba)2 (1.0 mol%, 0.09 g), reacted at 50C, and the reaction was completed by TLC. The organic solvent was concentrated, cooled to room temperature, added with 30 ml of water, and extracted with ethyl acetate (50 ml*3). The combined organic layers were washed with saturated brine (100 ml*3), dried over anhydrous sodium sulfate, and purified by column chromatography to give Compound 2 ''' (6.7 mmol, 1.99 g, 67%).
  • 6
  • [ 67137-56-8 ]
  • [ 103986-53-4 ]
  • 2-[5-(4-methylnaphthalen-1-yl)thiophen-2-yl]acetic acid [ No CAS ]
  • 7
  • [ 67137-56-8 ]
  • [ 355386-94-6 ]
  • C16H13NO2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
64% With potassium carbonate; bis(dibenzylideneacetone)-palladium(0); In ethanol; water; at 50℃; Into a 100 ml three-necked flask were added compound 5 (12 mmol, 2.07 g), compound 3 (10 mmol, 2.35 g), potassium carbonate (10 mmol, 1.38 g), 80% aqueous solution of ethanol 50 ml, Pd(dba) 2 (1.0 mol%, 0.09 g), reaction at 50C, TLC detection to completion of the reaction. The organic solvent was concentrated, cooled to room temperature, added with 30 ml of water, and extracted with ethyl acetate (50 ml*3). The combined organic layers were washed with saturated brine (100 ml*3), dried over anhydrous sodium sulfate, and purified by column chromatography to give Compound 2 (6.4 mmol, 1.81 g, 64%).
  • 8
  • [ 67137-56-8 ]
  • [ 355386-94-6 ]
  • 2-[5-(quinolin-5-yl)thiophen-2-yl]acetic acid [ No CAS ]
Recommend Products
Same Skeleton Products
Historical Records