Home Cart 0 Sign in  

[ CAS No. 440122-66-7 ] {[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| 440122-66-7
Chemical Structure| 440122-66-7
Structure of 440122-66-7 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 440122-66-7 ]

Related Doc. of [ 440122-66-7 ]

Alternatived Products of [ 440122-66-7 ]

Product Details of [ 440122-66-7 ]

CAS No. :440122-66-7 MDL No. :MFCD16618385
Formula : C13H8BrNO3 Boiling Point : -
Linear Structure Formula :- InChI Key :BAAILVWEAXFTSF-UHFFFAOYSA-N
M.W : 306.11 Pubchem ID :135418373
Synonyms :
WAY-00005

Calculated chemistry of [ 440122-66-7 ]

Physicochemical Properties

Num. heavy atoms : 18
Num. arom. heavy atoms : 15
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 71.19
TPSA : 66.49 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -5.75 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.22
Log Po/w (XLOGP3) : 3.41
Log Po/w (WLOGP) : 3.67
Log Po/w (MLOGP) : 2.28
Log Po/w (SILICOS-IT) : 3.08
Consensus Log Po/w : 2.93

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.44
Solubility : 0.0112 mg/ml ; 0.0000366 mol/l
Class : Moderately soluble
Log S (Ali) : -4.49
Solubility : 0.01 mg/ml ; 0.0000327 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -5.12
Solubility : 0.00232 mg/ml ; 0.00000759 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.72

Safety of [ 440122-66-7 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P301+P310-P305+P351+P338 UN#:2811
Hazard Statements:H301-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 440122-66-7 ]

* 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 [ 440122-66-7 ]
  • Downstream synthetic route of [ 440122-66-7 ]

[ 440122-66-7 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 67-56-1 ]
  • [ 440123-20-6 ]
  • [ 440122-66-7 ]
YieldReaction ConditionsOperation in experiment
92% With boron tribromide In dichloromethane Step e) 7-Bromo-2-(4-hydroxyphenyl)-1,3-benzoxazol-5-ol
Route a)
Boron tribromide (1M, 89.9 mL, 89.8 mmol) was added dropwise into a cold (-70° C.) suspension of 7-bromo-5-methoxy-2-(4-methoxyphenyl)-1,3-benzoxazole (10.0 g, 29.94 mmol) and CH2Cl2 (50 mL).
The mixture was allowed to warm up to room temperature.
During the warming up period the suspension turned into a dark solution.
The mixture was stirred at room temperature for 2 days and then poured slowly into cold (0° C.) ethyl ether (1000 mL).
Methyl alcohol (200 mL) was added slowly into the new mixture over a 20 min period.
The mixture was then poured into water (1.5 l).
The organic layer was washed three times with water, and dried over MgSO4.
Evaporation and crystallization from acetone/ethyl ether/hexanes gave an off-white solid (8.4 g, 92percent yield, m.p. 298-299° C.); MS m/e 306 (M+H)+.
Reference: [1] Patent: US2003/199562, 2003, A1,
  • 2
  • [ 440123-20-6 ]
  • [ 440122-66-7 ]
YieldReaction ConditionsOperation in experiment
92%
Stage #1: With boron tribromide In dichloromethane at -70 - 20℃; for 48 h;
Stage #2: With water In methanol; diethyl ether; dichloromethane at 0℃;
Boron tribromide (1M, 89.9 mL, 89.8 mmol) was added dropwise into a cold (-70° C.) suspension of 7-bromo-5-methoxy-2-(4-methoxyphenyl)-1,3-benzoxazole (10.0 g, 29.94 mmol) and CH2Cl2 (50 mL). The reaction mixture was allowed to warm up to room temperature. During the warming up period, the suspension turned into a dark solution. The reaction mixture was stirred at room temperature for 2 days and then poured slowly into cold (0° C.) ethyl ether (1000 mL). Methyl alcohol (200 mL) was added slowly into the new reaction mixture over a 20 mins. period. The reaction mixture was then poured into water (1.5 l). The organic layer was washed three times with water, and dried over MgSO4. Evaporation and crystallization from acetone/ethyl ether/hexanes gave an off-white solid (8.4 g, 92percent yield, m.p. 298-299° C.); MS m/e 306 (M+H)+. Analysis for: C13H8BrNO3 Calc'd: C, 51.01; H, 2.63; N, 4.58 Found: C, 50.96; H, 2.30; N, 4.42
86%
Stage #1: With boron tribromide In dichloromethane at -78 - 20℃; for 1 h;
Stage #2: With water In dichloromethane
Boron tribromide (0.25 mL, 2.7 mmol) was added dropwise into a cold (-78° C.) mixture of 7-bromo-5-methoxy-2-(4-methoxyphenyl)-1,3-benzoxazole (130 mg, 0.39 mmol), and dichloromethane (1.5 mL). The reaction mixture was allowed to come gradually to room temperature and stirred for 1 hour. The reaction mixture was poured into ice and extracted with EtOAc. The organic extracts were washed with brine and dried over MgSO4. Evaporation and flash chromatography (30percent-40percent EtOAc/petroleum ether) gave (102 mg, 86percent yield) of the product as a light pink solid, m.p. 295-298° C.; MS m/e 304 (M-H)+. Analysis for: C13H8BrNO3 Calc'd: C, 51.01; H, 2.63; N, 4.58 Found: C, 51.06; H, 2.77; N, 4.36.
Reference: [1] Patent: US2006/46968, 2006, A1, . Location in patent: Page/Page column 28
[2] Patent: US2006/46968, 2006, A1, . Location in patent: Page/Page column 28
  • 3
  • [ 1568-70-3 ]
  • [ 115929-59-4 ]
  • [ 440122-66-7 ]
YieldReaction ConditionsOperation in experiment
60% With hydrogenchloride; CH3CO2Na; bromine In acetic acid; ethyl acetate 7-Bromo-2-(4-hydroxy-phenyl)-benzooxazol-5-ol
Synthetic Method J:
Synthesis of 2-bromo-4-methoxy-6-nitro-phenol
4-Methoxy-2-nitro-phenol (10 g) was dissolved in glacial acetic acid (60 mL) and CH3CO2Na (8.2 g) was added.
Next, bromine (3 mL) dissolved in glacial acetic acid (12 mL) was added drop wise to the stirring solution at room temperature.
After complete addition of bromine, the mixture was stirred for 30 min at room temperature and then placed in an oil bath at 75° C. for 2 h.
After reaction mixture cooled to room temperature, concentrated HCl (500 mL) was slowly added to the mixture followed by addition of ethyl acetate (500 mL).
The layers were separated and the organic layer was washed with water, brine, dried (Na2SO4).
Flash chromatography on silica gel eluding with 5percent ethyl acetate-hexane afforded 8.8 g (60percent) of the title compound as a solid. MS: 218 (MH+-30), HPLC tR: 2.40 min.
According to synthetic methods F, G, H (except the reaction mixture was heated in an oil bath at 85° C. for 2 h), and I was obtained 7-bromo-2-(4-hydroxy-phenyl)-benzooxazol-5-ol. MS: 308 (Mob), HPLC tR: 2.29 min. NMR (DMSO-d6): 10.34 (s, 1M), 9.82 (s, 1H), 7.99 (d, 2H, J=8.4 Hz), 6.95-7.04 (m, 4H).
Reference: [1] Patent: US2004/102435, 2004, A1,
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 440122-66-7 ]

Aryls

Chemical Structure| 13676-47-6

[ 13676-47-6 ]

2-(4-Aminophenyl)benzo[d]oxazol-5-amine

Similarity: 0.87

Chemical Structure| 544704-73-6

[ 544704-73-6 ]

7-Bromo-2-(3-fluoro-4-hydroxyphenyl)benzo[d]oxazol-5-ol

Similarity: 0.86

Chemical Structure| 1367920-70-4

[ 1367920-70-4 ]

(2-Phenylbenzo[d]oxazol-6-yl)methanamine

Similarity: 0.83

Chemical Structure| 16707-41-8

[ 16707-41-8 ]

1-(4-(Benzo[d]oxazol-2-yl)phenyl)-1H-pyrrole-2,5-dione

Similarity: 0.75

Chemical Structure| 654655-69-3

[ 654655-69-3 ]

3-Benzyl-6-bromo-2-methoxyquinoline

Similarity: 0.74

Bromides

Chemical Structure| 544704-73-6

[ 544704-73-6 ]

7-Bromo-2-(3-fluoro-4-hydroxyphenyl)benzo[d]oxazol-5-ol

Similarity: 0.86

Chemical Structure| 5676-56-2

[ 5676-56-2 ]

5-Bromo-2-methyl-1,3-benzoxazole

Similarity: 0.81

Chemical Structure| 938458-80-1

[ 938458-80-1 ]

5-Bromo-2-ethylbenzo[d]oxazole

Similarity: 0.75

Chemical Structure| 654655-69-3

[ 654655-69-3 ]

3-Benzyl-6-bromo-2-methoxyquinoline

Similarity: 0.74

Chemical Structure| 132244-31-6

[ 132244-31-6 ]

5-Bromobenzo[d]oxazole

Similarity: 0.73

Alcohols

Chemical Structure| 544704-73-6

[ 544704-73-6 ]

7-Bromo-2-(3-fluoro-4-hydroxyphenyl)benzo[d]oxazol-5-ol

Similarity: 0.86

Chemical Structure| 136663-38-2

[ 136663-38-2 ]

(2-Methylbenzo[d]oxazol-5-yl)methanol

Similarity: 0.77

Chemical Structure| 1261677-80-8

[ 1261677-80-8 ]

7-Bromoquinolin-5-ol

Similarity: 0.70

Chemical Structure| 89446-19-5

[ 89446-19-5 ]

6-Bromo-4-methylquinolin-2-ol

Similarity: 0.67

Chemical Structure| 122794-99-4

[ 122794-99-4 ]

Ethyl 6-bromo-4-hydroxyquinoline-3-carboxylate

Similarity: 0.66

Related Parent Nucleus of
[ 440122-66-7 ]

Benzoxazoles

Chemical Structure| 13676-47-6

[ 13676-47-6 ]

2-(4-Aminophenyl)benzo[d]oxazol-5-amine

Similarity: 0.87

Chemical Structure| 544704-73-6

[ 544704-73-6 ]

7-Bromo-2-(3-fluoro-4-hydroxyphenyl)benzo[d]oxazol-5-ol

Similarity: 0.86

Chemical Structure| 1367920-70-4

[ 1367920-70-4 ]

(2-Phenylbenzo[d]oxazol-6-yl)methanamine

Similarity: 0.83

Chemical Structure| 5676-56-2

[ 5676-56-2 ]

5-Bromo-2-methyl-1,3-benzoxazole

Similarity: 0.81

Chemical Structure| 136663-38-2

[ 136663-38-2 ]

(2-Methylbenzo[d]oxazol-5-yl)methanol

Similarity: 0.77