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[ CAS No. 456-55-3 ] {[proInfo.proName]}

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Type HazMat fee for 500 gram (Estimated)
Excepted Quantity USD 0.00
Limited Quantity USD 15-60
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Inaccessible (Haz class 6.1), International USD 150+
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3d Animation Molecule Structure of 456-55-3
Chemical Structure| 456-55-3
Chemical Structure| 456-55-3
Structure of 456-55-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 456-55-3 ]

CAS No. :456-55-3 MDL No. :MFCD00040832
Formula : C7H5F3O Boiling Point : -
Linear Structure Formula :- InChI Key :GQHWSLKNULCZGI-UHFFFAOYSA-N
M.W : 162.11 Pubchem ID :68010
Synonyms :

Calculated chemistry of [ 456-55-3 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 33.12
TPSA : 9.23 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) : -5.04 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.99
Log Po/w (XLOGP3) : 3.17
Log Po/w (WLOGP) : 3.85
Log Po/w (MLOGP) : 2.3
Log Po/w (SILICOS-IT) : 2.37
Consensus Log Po/w : 2.74

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.11
Solubility : 0.125 mg/ml ; 0.000769 mol/l
Class : Soluble
Log S (Ali) : -3.03
Solubility : 0.15 mg/ml ; 0.000924 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.01
Solubility : 0.157 mg/ml ; 0.000971 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.24

Safety of [ 456-55-3 ]

Signal Word:Danger Class:3
Precautionary Statements:P210-P261-P305+P351+P338 UN#:1993
Hazard Statements:H225-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 456-55-3 ]

* 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 [ 456-55-3 ]
  • Downstream synthetic route of [ 456-55-3 ]

[ 456-55-3 ] Synthesis Path-Upstream   1~25

  • 1
  • [ 456-55-3 ]
  • [ 32858-93-8 ]
Reference: [1] European Journal of Organic Chemistry, 2001, # 4, p. 691 - 695
  • 2
  • [ 456-55-3 ]
  • [ 828-27-3 ]
Reference: [1] Patent: WO2016/125185, 2016, A2,
  • 3
  • [ 456-55-3 ]
  • [ 450-96-4 ]
  • [ 461-81-4 ]
  • [ 772-49-6 ]
Reference: [1] Journal of the American Chemical Society, 1987, vol. 109, p. 3708
  • 4
  • [ 456-55-3 ]
  • [ 64115-88-4 ]
Reference: [1] European Journal of Organic Chemistry, 2001, # 4, p. 691 - 695
  • 5
  • [ 456-55-3 ]
  • [ 64115-88-4 ]
  • [ 407-14-7 ]
Reference: [1] Journal of the American Chemical Society, 1987, vol. 109, p. 3708
  • 6
  • [ 1035797-66-0 ]
  • [ 88284-48-4 ]
  • [ 64115-88-4 ]
  • [ 456-55-3 ]
Reference: [1] Journal of the American Chemical Society, 2018, vol. 140, # 22, p. 6801 - 6805
  • 7
  • [ 456-55-3 ]
  • [ 713-65-5 ]
YieldReaction ConditionsOperation in experiment
85% With sulfuric acid; nitric acid In dichloromethane at 0 - 30℃; for 2 h; Trifloromethoxybenzene is nitrated with concentrated Sulphuric acid + concentrated nitric acid at OOc (Nitration mixture) to 35°C.The reaction produces mixture of isomers having close boiling points. Between ortho and para isomer, para isomer was formed as major and is about 90percent. And the by-product formed during the reaction is Sulphuric acid and water. The crude product isolated by using DCM layer separation followed by the evaporation of DCM solvent.Trifluoromethoxy benzene(1 18g) and dichloromethane(590g) are charged in glass round bottomed flask and cooled to about 0°C. The nitration mixture (HNO3 (58.24g) +H2504(174.24g)) was added from top at temperature in the range of 5° to 10°C for about 1 hour. The temperature of the mixture was raised slowly to 30°C and maintained for additional 1 hour. After the completion of the reaction, the reaction mass was quenched into ice cold water and solvent layers were separated. The aqueous layers so extracted with the solvent were combined with the solvent layers,dried and evaporated to obtain 1-Nitro-4-trifluoromethoxy-benzene (135g)
Reference: [1] Patent: WO2016/125185, 2016, A2, . Location in patent: Page/Page column 7; 8
  • 8
  • [ 456-55-3 ]
  • [ 713-65-5 ]
  • [ 1644-88-8 ]
Reference: [1] Journal of the American Chemical Society, 1987, vol. 109, p. 3708
[2] Organic Process Research and Development, 2017, vol. 21, # 11, p. 1843 - 1850
  • 9
  • [ 24210-45-5 ]
  • [ 866632-64-6 ]
  • [ 456-55-3 ]
  • [ 461-81-4 ]
  • [ 587-18-8 ]
Reference: [1] Organic Letters, 2016, vol. 18, # 15, p. 3754 - 3757
  • 10
  • [ 456-55-3 ]
  • [ 450-96-4 ]
  • [ 461-81-4 ]
  • [ 772-49-6 ]
Reference: [1] Journal of the American Chemical Society, 1987, vol. 109, p. 3708
  • 11
  • [ 456-55-3 ]
  • [ 407-14-7 ]
YieldReaction ConditionsOperation in experiment
83.8% at 100℃; for 16 h; Step 2
1-bromo-4-(trifluoromethoxy)benzene
Trifluoromethoxybenzene 6c (11.35 g, 70 mmol) was dissolved in 3.57 mL liquid bromine, followed by addition of iron (0.24 g).
The reaction mixture was stirred for 16 hours at 100° C. 450 mL of dichloromethane were added and the organic extract was washed with 6 M hydrochloric acid (140 mL), 10percent sodium hydrogen sulfite solution (140 mL) and saturated sodium chloride solution (140 mL), combined, dried over anhydrous magnesium sulfate, and filtered.
The filtrate was concentrated under reduced pressure to obtain the title compound 1-bromo-4-(trifluoromethoxy)benzene 6d (14.1 g, yellow solid), yield: 83.8percent. 1H NMR (400 MHz, CDCl3): δ 7.54-7.50 (m, 2H), 7.11-7.09 (m, 2H).
Reference: [1] Patent: US2013/130997, 2013, A1, . Location in patent: Paragraph 0150
  • 12
  • [ 456-55-3 ]
  • [ 107713-64-4 ]
  • [ 407-14-7 ]
Reference: [1] Patent: US5225607, 1993, A,
[2] Patent: US4891450, 1990, A,
  • 13
  • [ 456-55-3 ]
  • [ 64115-88-4 ]
  • [ 407-14-7 ]
Reference: [1] Journal of the American Chemical Society, 1987, vol. 109, p. 3708
  • 14
  • [ 456-55-3 ]
  • [ 461-82-5 ]
Reference: [1] Patent: WO2016/125185, 2016, A2,
  • 15
  • [ 456-55-3 ]
  • [ 50824-05-0 ]
YieldReaction ConditionsOperation in experiment
60% With sodium bromide; sulfuric acid; paraformaldehyde In tert-butyl methyl ether; water; acetic acid Example 1
4-Bromomethyl-1-trifluoromethoxybenzene
300 g of trifluoromethoxybenzene, 111 g of paraformaldehyde, 456 g of sodium bromide, and 900 ml of glacial acetic acid were initially charged and heated at 90° C.
To release hydrogen bromide, a mixture of 450 ml of glacial acetic acid and 678 g of concentrated sulfuric acid was then added dropwise.
After the addition had ended, the reaction mixture was stirred at 90° C. for 20 hours.
The reaction mixture was then poured onto 1,000 g of ice and extracted twice with in each case 300 ml of methyl tert-butyl ether.
The combined organic extracts were washed with 100 ml of water and concentrated.
The residue was distilled at 20 hPa in a spinning band column.
This gave 324.3 g of 4-bromomethyl-1-trifluoromethoxybenzene as a colorless liquid (60percent of theory) of b.p. 82-83° C.
Reference: [1] Patent: US2002/82454, 2002, A1,
  • 16
  • [ 456-55-3 ]
  • [ 450-96-4 ]
  • [ 461-81-4 ]
  • [ 772-49-6 ]
Reference: [1] Journal of the American Chemical Society, 1987, vol. 109, p. 3708
  • 17
  • [ 456-55-3 ]
  • [ 713-65-5 ]
  • [ 1644-88-8 ]
Reference: [1] Journal of the American Chemical Society, 1987, vol. 109, p. 3708
[2] Organic Process Research and Development, 2017, vol. 21, # 11, p. 1843 - 1850
  • 18
  • [ 124-38-9 ]
  • [ 456-55-3 ]
  • [ 1979-29-9 ]
Reference: [1] European Journal of Organic Chemistry, 2001, # 4, p. 691 - 695
  • 19
  • [ 456-55-3 ]
  • [ 75-36-5 ]
  • [ 85013-98-5 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1986, # 6, p. 885 - 890
[2] Bulletin de la Societe Chimique de France, 1986, # 6, p. 885 - 890
[3] Journal of the American Chemical Society, 1987, vol. 109, p. 3708
  • 20
  • [ 456-55-3 ]
  • [ 108-24-7 ]
  • [ 85013-98-5 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 13, p. 2668 - 2674
  • 21
  • [ 456-55-3 ]
  • [ 75-36-5 ]
  • [ 34888-05-6 ]
  • [ 85013-98-5 ]
Reference: [1] Synthetic Communications, 2002, vol. 32, # 5, p. 799 - 801
  • 22
  • [ 456-55-3 ]
  • [ 68-12-2 ]
  • [ 94651-33-9 ]
Reference: [1] European Journal of Organic Chemistry, 2001, # 4, p. 691 - 695
  • 23
  • [ 456-55-3 ]
  • [ 175278-00-9 ]
Reference: [1] Tetrahedron Letters, 2008, vol. 49, # 41, p. 6013 - 6015
  • 24
  • [ 456-55-3 ]
  • [ 1130-90-1 ]
  • [ 63968-85-4 ]
Reference: [1] European Journal of Organic Chemistry, 2001, # 4, p. 691 - 695
  • 25
  • [ 456-55-3 ]
  • [ 175676-65-0 ]
Reference: [1] European Journal of Organic Chemistry, 2001, # 4, p. 691 - 695
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