Home Cart 0 Sign in  

[ CAS No. 55453-87-7 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
HazMat Fee +

There will be a HazMat fee per item when shipping a dangerous goods. The HazMat fee will be charged to your UPS/DHL/FedEx collect account or added to the invoice unless the package is shipped via Ground service. Ship by air in Excepted Quantity (each bottle), which is up to 1g/1mL for class 6.1 packing group I or II, and up to 25g/25ml for all other HazMat items.

Type HazMat fee for 500 gram (Estimated)
Excepted Quantity USD 0.00
Limited Quantity USD 15-60
Inaccessible (Haz class 6.1), Domestic USD 80+
Inaccessible (Haz class 6.1), International USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic USD 100+
Accessible (Haz class 3, 4, 5 or 8), International USD 200+
Chemical Structure| 55453-87-7
Chemical Structure| 55453-87-7
Structure of 55453-87-7 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 55453-87-7 ]

Related Doc. of [ 55453-87-7 ]

Alternatived Products of [ 55453-87-7 ]

Product Details of [ 55453-87-7 ]

CAS No. :55453-87-7 MDL No. :
Formula : C16H12O4 Boiling Point : -
Linear Structure Formula :- InChI Key :QFGMXJOBTNZHEL-UHFFFAOYSA-N
M.W : 268.26 Pubchem ID :41448
Synonyms :
HP 549

Calculated chemistry of [ 55453-87-7 ]

Physicochemical Properties

Num. heavy atoms : 20
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.12
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 72.4
TPSA : 63.6 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) : -6.21 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.99
Log Po/w (XLOGP3) : 2.43
Log Po/w (WLOGP) : 2.29
Log Po/w (MLOGP) : 1.72
Log Po/w (SILICOS-IT) : 3.23
Consensus Log Po/w : 2.33

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -3.35
Solubility : 0.121 mg/ml ; 0.000451 mol/l
Class : Soluble
Log S (Ali) : -3.41
Solubility : 0.105 mg/ml ; 0.00039 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.87
Solubility : 0.00359 mg/ml ; 0.0000134 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 3.13

Safety of [ 55453-87-7 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P201-P202-P260-P264-P270-P280-P301+P310+P330-P308+P313-P405-P501 UN#:2811
Hazard Statements:H301-H361-H372 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 55453-87-7 ]

* 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 [ 55453-87-7 ]
  • Downstream synthetic route of [ 55453-87-7 ]

[ 55453-87-7 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 55453-89-9 ]
  • [ 55453-87-7 ]
YieldReaction ConditionsOperation in experiment
96.4%
Stage #1: With trifluoroacetic anhydride In chlorobenzene at 20℃; for 4 h;
Stage #2: at -10 - 0℃; for 0.666667 h;
The whole quantity of the 2-(4-carboxymethylphenoxymethyl)benzoic acid obtained in the above Step 4 and 200 ml of chlorobenzene were charged into a 500-ml four-necked flask, 75.0 g (0.3753 mol) of trifluoroacetic anhydride was added thereto, and the mixture was stirred at about 20°C for 4 hours. Subsequently, 2.3 g (0.0162 mol) of BF3-etherate complex was added dropwise thereto at -10 to 0°C over 10 minutes, then the mixture was stirred for 30 minutes. An aqueous phase was then separated, and the organic layer was washed with 200 ml of water. The washed organic layer was added to a solution of 7.2g of sodium hydroxide dissolved in 300 ml of water, and stirred for 30 minutes. An aqueous phase was then separated. To the separated aqueous layer, 2.0 g of activated carbon was added, stirred for 30 minutes, and filtered though a Buchner funnel to separate activated carbon. The activated carbon was washed on a Buchner funnel with 10 ml of water. A mixture of the filtrate and the cleaning solution was maintained at about 40°C, and a mixed solution of 11.3 g (0.1876 mol) of acetic acid and 50 ml of water was added dropwise thereto over 30 minutes. After the dropwise addition was completed, the mixture was cooled to 0 to 10°C, filtered through a Buchner funnel to collect crystals, and washed with 200 ml of water. The washed crystals were dried under reduced pressure to obtain 42.0 g of the title compound, (11-oxo-6,11-dihydrodibenz[b,e]oxepin-2-acetic acid). The yield (yield from 2-(4-carboxymethylphenoxymethyl)benzoic acid) was 96.4percent, and the purity as measured by HPLC was 99.9percent.(HPLC conditions) Column: Inertsil ODS-5 μm (4.6 mm ID x 15 cm)Mobile Phase: 0.02percent trifluoroacetic acid aqueous solution/acetonitrile = 5/5 --> 3/7 (30 minutes)Detection Wavelength: UV 254 nm(Physical Property Data) 1H NMR (400 MHz, DMSOd6) δ 3.63 (s, 2H), 5.30 (s, 2H), 7.07 (d, J = 8.0 Hz, 2H), 7.48 (t, J = 3.6 Hz, 1H), 7.55 (d-d, J = 7.9 Hz, 2H), 7.67 (t, J = 7.6 Hz, 1H), 7.78 (d, J = 7.6 Hz, 1H), 7.97 (d, J = 2.0 Hz, 1H)
71.3%
Stage #1: With trifluorormethanesulfonic acid; trifluoroacetic anhydride In toluene at 20 - 35℃; for 1 h;
Stage #2: With water In toluene
Example 2; Synthesis of the Intermediate 6,11-dihydro-11-oxo-dibenz[b,e]oxepin-2-acetic acid (Olo-IM2) To a suspension of 4-(2-carboxybenzyloxy)phenylacetic acid (Olo-IM1) (300.09 g, 1.04 mol; assay: 99.0percent) and trifluoromethane sulfonic acid (4.77 g, 0.03 mol; assay: 98.0percent) in toluene (1122 g) was added slowly trifluoroacetic anhydride (255.18 g, 1.20 mol; assay: 99.0percent) at 20-35° C. The brown solution was stirred after complete addition of trifluoroacetic anhydride for 1 hour at 20-25° C. and the mixture was then hydrolyzed with water (99.0 g). Afterwards, the mixture was distilled under normal pressure until the steam temperature was 105-110° C. (1191 g two-phase distillate). The residue was diluted with toluene (261 g) and the suspension was heated to reflux. The dark solution was then cooled to 75° C. and seeded with crystals of 6,11-dihydro-11-oxo-dibenz[b,e]oxepin-2-acetic acid (Olo-IM2). The suspension was stirred after cooling to 20-25° C. for additional 1-2 hours at this temperature. The product was filtered off, washed with cyclohexane (600 g) and water (390 g) and dried under vacuum (20 h, 50° C.) to give 6,11-dihydro-11-oxo-dibenz[b,e]oxepin-2-acetic acid (Olo-IM2) (yield: 203.21 g, 0.76 mol, 73.0percent; HPLC assay >99.5percent, HPLC purity: 99.62percent). This product was then recrystallized from a mixture of cyclohexane (700 g) and toluene (1892 g). After filtration the wet product was washed with cyclohexane (466 g) and dried under vacuum (15 h, 70° C.) to give slightly gray colored 6,11-dihydro-11-oxo-dibenz[b,e]oxepin-2-acetic acid (Olo-IM2) (yield: 198.4 g, 0.74 mol, 97.6percent; HPLC assay >99.5percent, HPLC purity: 99.90percent; overall yield: 71.3percent).
69.9% at 80 - 90℃; for 2 h; Large scale The 10 kg acetic anhydride heated to 70-80°C, batch by adding 2 kg intermediate II, after adding to 80-90 °C stirring 2h, cooling to room temperature, to the reaction solution slowly and 40L water, precipitating a large amount of the yellow solid, stirring for 30 min, filtration, recrystallization with isopropanol/water, shall be intermediate III1.31kg, yield: 69.9percent, purity of 99.1percent.
0.8 kg With acetic acid In cyclohexane at 70 - 85℃; 15 mg of HAClL, cyclohexane 0. 5 L and 4- (2-hydroxybenzyloxy) phenylacetic acid were charged into a reaction vessel, stirred and the reaction was stirred at 70-85 ° C for 2-4 hours. Stir under the conditions of adding appropriate amount of drinking water, stirring, filtering, drinking water to wash the solid.

Reference: [1] Patent: EP2072507, 2009, A1, . Location in patent: Page/Page column 10-11
[2] Patent: US2007/232814, 2007, A1, . Location in patent: Page/Page column 23-24
[3] Patent: CN104262318, 2016, B, . Location in patent: Paragraph 0055; 0056
[4] Journal of Medicinal Chemistry, 1996, vol. 39, # 1, p. 246 - 252
[5] Patent: US4585788, 1986, A,
[6] Patent: WO2011/128911, 2011, A2, . Location in patent: Page/Page column 21-22
[7] Patent: CN106518833, 2017, A, . Location in patent: Paragraph 0008-0009
  • 2
  • [ 156-38-7 ]
  • [ 85888-81-9 ]
  • [ 55453-87-7 ]
YieldReaction ConditionsOperation in experiment
79.3%
Stage #1: With potassium hydroxide In methanol at 20℃; for 1 h;
Stage #2: Reflux
Stage #3: at 80℃; for 2 h;
Reaction flask was added p-hydroxyphenyl acetic acid (150mmol) 22.67g, potassium hydroxide (200mmol) 11.22g, 90ml of methanol, stirred for 1 hour at room temperature, was added 2- (chloromethyl) benzoic acid (100mmol) 17.06g, heated at reflux The reaction, after the reaction was monitored by TLC, the solvent was distilled off under reduced pressure, 200ml of dichloromethane was added to dissolve, washed with water, dried, concentrated, Eaton reagent was added 7.5percent (mass concentration) 200ml, was heated to 80 deg.] C, stirred for 2 hours, the reaction was completed after addition of saturated sodium carbonate solution, filtration, and recrystallized from ethanol to give Isoxepac (79.3mmol) 21.27g, yield 79.3percent, HPLC purity of 99.9percent.
Reference: [1] Patent: CN105693685, 2016, A, . Location in patent: Paragraph 0050; 0051
  • 3
  • [ 69031-39-6 ]
  • [ 55453-87-7 ]
Reference: [1] Patent: US4118401, 1978, A,
  • 4
  • [ 2417-73-4 ]
  • [ 55453-87-7 ]
Reference: [1] Journal of Medicinal Chemistry, 1996, vol. 39, # 1, p. 246 - 252
  • 5
  • [ 17138-28-2 ]
  • [ 55453-87-7 ]
Reference: [1] Journal of Medicinal Chemistry, 1996, vol. 39, # 1, p. 246 - 252
  • 6
  • [ 156-38-7 ]
  • [ 55453-87-7 ]
Reference: [1] Patent: WO2011/128911, 2011, A2,
  • 7
  • [ 87-41-2 ]
  • [ 55453-87-7 ]
Reference: [1] Patent: WO2011/128911, 2011, A2,
  • 8
  • [ 1009378-92-0 ]
  • [ 55453-87-7 ]
Reference: [1] Patent: CN104262318, 2016, B,
  • 9
  • [ 34040-62-5 ]
  • [ 55453-87-7 ]
Reference: [1] Patent: CN104262318, 2016, B,
  • 10
  • [ 14199-15-6 ]
  • [ 55453-87-7 ]
Reference: [1] Patent: CN104262318, 2016, B,
Same Skeleton Products
Historical Records