Home Cart 0 Sign in  
X

[ CAS No. 401-78-5 ] {[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+
3d Animation Molecule Structure of 401-78-5
Chemical Structure| 401-78-5
Chemical Structure| 401-78-5
Structure of 401-78-5 * 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 [ 401-78-5 ]

Related Doc. of [ 401-78-5 ]

Alternatived Products of [ 401-78-5 ]
Product Citations

Product Citations

Keyes, Robert F. ; McAllister, Donna ; Dwinell, Michael B. , et al. DOI: PubMed ID:

Abstract: Triphenylphosphonium (TPP+) compounds like mito-metformin (MMe) target cancer cells by exploiting their hyperpolarized mitochondrial membrane potential. Here, we present a protocol for synthesizing TPP+ analogs with selectivity for mammalian cancer cells, reduced toxicity, and quantifiability using fluorine-19 NMR (19F-NMR). We describe steps for treating mammalian cells with mitochondria-targeted compounds, treating and preparing mouse tissue with these compounds, and 19F-NMR detection of MMe analogs in cells and tissue. TPP+-conjugated metformin analogs include para-methoxy (pMeO-MMe) and para-trifluoromethyl MMe (pCF3-MMe) and meta-trifluoromethyl MMe (mCF3-MMe).

Purchased from AmBeed: ; ; ;

Product Details of [ 401-78-5 ]

CAS No. :401-78-5 MDL No. :MFCD00000380
Formula : C7H4BrF3 Boiling Point : -
Linear Structure Formula :- InChI Key :NNMBNYHMJRJUBC-UHFFFAOYSA-N
M.W : 225.01 Pubchem ID :9817
Synonyms :

Calculated chemistry of [ 401-78-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 39.14
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.07 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.25
Log Po/w (XLOGP3) : 3.66
Log Po/w (WLOGP) : 4.62
Log Po/w (MLOGP) : 4.1
Log Po/w (SILICOS-IT) : 3.51
Consensus Log Po/w : 3.63

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.88
Solubility : 0.0298 mg/ml ; 0.000132 mol/l
Class : Soluble
Log S (Ali) : -3.35
Solubility : 0.101 mg/ml ; 0.000448 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.14
Solubility : 0.0162 mg/ml ; 0.0000719 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 1.36

Safety of [ 401-78-5 ]

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

Application In Synthesis of [ 401-78-5 ]

* 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 [ 401-78-5 ]
  • Downstream synthetic route of [ 401-78-5 ]

[ 401-78-5 ] Synthesis Path-Upstream   1~31

  • 1
  • [ 110-85-0 ]
  • [ 401-78-5 ]
  • [ 15532-75-9 ]
YieldReaction ConditionsOperation in experiment
77% With potassium phosphate; johnphos In toluene for 16 h; A mixture of piperidine (3.54g, 41.0 MMOL), 3-BROMOBENZOTRIFLUORIDE (4.60 g, 20.6 mmol), potassium phosphate (6.10 g, 28.8 mmol), 2-di-tert-butylphosphinobiphenyl (0. 835G, 2.80 MMOL), tris (dibenzylideneacetone) dipalladium (1. 28G, 1.4 MMOL), and toluene (42 mL) were stirred for 16 h. The mixture was then filtered through celite and the filtrate washed with water (2 x 50 mL) and brine (1 x 50 mL), dried (NaS04), and concentrated to a solid. Chromatography of this material on silica gel using Hexanes/Ethyl Acetate (2: 3) yielded 1 (3.63 g, 15.8 mmol, 77percent, m/z + = 231).
Reference: [1] Patent: WO2005/5382, 2005, A2, . Location in patent: Page 57; 58
  • 2
  • [ 110-85-0 ]
  • [ 401-78-5 ]
  • [ 98-08-8 ]
  • [ 15532-75-9 ]
Reference: [1] Tetrahedron Letters, 1998, vol. 39, # 7, p. 617 - 620
  • 3
  • [ 401-78-5 ]
  • [ 15532-75-9 ]
Reference: [1] Tetrahedron Letters, 2006, vol. 47, # 15, p. 2549 - 2552
  • 4
  • [ 401-78-5 ]
  • [ 2338-76-3 ]
Reference: [1] Chemistry Letters, 1983, p. 193 - 194
  • 5
  • [ 401-78-5 ]
  • [ 62-53-3 ]
  • [ 101-23-5 ]
Reference: [1] New Journal of Chemistry, 2017, vol. 41, # 17, p. 9414 - 9423
  • 6
  • [ 401-78-5 ]
  • [ 7657-08-1 ]
Reference: [1] Journal of Organic Chemistry, 2006, vol. 71, # 5, p. 2188 - 2191
  • 7
  • [ 98-08-8 ]
  • [ 401-78-5 ]
  • [ 7657-08-1 ]
Reference: [1] Journal of the American Chemical Society, 1943, vol. 65, p. 389,390
  • 8
  • [ 98-08-8 ]
  • [ 401-78-5 ]
  • [ 7657-08-1 ]
  • [ 401-84-3 ]
  • [ 7657-09-2 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1991, vol. 27, # 1.2, p. 108 - 112[2] Zhurnal Organicheskoi Khimii, 1991, vol. 27, # 1, p. 125 - 129
  • 9
  • [ 401-78-5 ]
  • [ 77287-34-4 ]
  • [ 1801-10-1 ]
Reference: [1] Journal of Organic Chemistry, 2002, vol. 67, # 2, p. 594 - 597
  • 10
  • [ 401-78-5 ]
  • [ 201230-82-2 ]
  • [ 77287-34-4 ]
  • [ 1801-10-1 ]
Reference: [1] Journal of Organic Chemistry, 2002, vol. 67, # 2, p. 594 - 597
  • 11
  • [ 401-78-5 ]
  • [ 201230-82-2 ]
  • [ 1801-10-1 ]
Reference: [1] Journal of Organic Chemistry, 2001, vol. 66, # 12, p. 4311 - 4315
[2] ChemCatChem, 2017, vol. 9, # 22, p. 4206 - 4211
  • 12
  • [ 288-32-4 ]
  • [ 401-78-5 ]
  • [ 60-29-7 ]
  • [ 1801-10-1 ]
Reference: [1] Patent: US6441233, 2002, B1,
  • 13
  • [ 98-08-8 ]
  • [ 401-78-5 ]
  • [ 7657-08-1 ]
  • [ 401-84-3 ]
  • [ 7657-09-2 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1991, vol. 27, # 1.2, p. 108 - 112[2] Zhurnal Organicheskoi Khimii, 1991, vol. 27, # 1, p. 125 - 129
  • 14
  • [ 401-78-5 ]
  • [ 445-02-3 ]
Reference: [1] Journal of the American Chemical Society, 1951, vol. 73, p. 3932
[2] Journal of the American Chemical Society, 1947, vol. 69, p. 2022
  • 15
  • [ 98-08-8 ]
  • [ 401-78-5 ]
  • [ 7657-08-1 ]
  • [ 401-84-3 ]
  • [ 7657-09-2 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1991, vol. 27, # 1.2, p. 108 - 112[2] Zhurnal Organicheskoi Khimii, 1991, vol. 27, # 1, p. 125 - 129
  • 16
  • [ 401-78-5 ]
  • [ 96-34-4 ]
  • [ 62451-84-7 ]
Reference: [1] Tetrahedron, 2007, vol. 63, # 5, p. 1146 - 1153
  • 17
  • [ 401-78-5 ]
  • [ 344-38-7 ]
Reference: [1] Journal of the American Chemical Society, 1951, vol. 73, p. 3932
  • 18
  • [ 401-78-5 ]
  • [ 777-44-6 ]
Reference: [1] Synthesis, 1986, # 10, p. 852 - 854
  • 19
  • [ 401-78-5 ]
  • [ 78573-45-2 ]
Reference: [1] Patent: EP2327684, 2011, A1,
[2] Patent: US2011/124917, 2011, A1,
[3] Organic Letters, 2019, vol. 21, # 1, p. 65 - 69
  • 20
  • [ 401-78-5 ]
  • [ 124-38-9 ]
  • [ 328-89-2 ]
Reference: [1] Tetrahedron Letters, 1996, vol. 37, # 16, p. 2767 - 2770
  • 21
  • [ 401-78-5 ]
  • [ 21172-41-8 ]
Reference: [1] Patent: EP2327684, 2011, A1,
[2] Patent: US2011/124917, 2011, A1,
  • 22
  • [ 401-78-5 ]
  • [ 364-12-5 ]
Reference: [1] Journal of the American Chemical Society, 2008, vol. 130, # 2, p. 472 - 480
[2] Journal of the American Chemical Society, 1951, vol. 73, p. 3932
  • 23
  • [ 3984-22-3 ]
  • [ 401-78-5 ]
  • [ 585-50-2 ]
Reference: [1] Tetrahedron, 2004, vol. 60, # 50, p. 11533 - 11540
  • 24
  • [ 401-78-5 ]
  • [ 585-50-2 ]
Reference: [1] Journal of Organic Chemistry, 2011, vol. 76, # 7, p. 2187 - 2194
  • 25
  • [ 401-78-5 ]
  • [ 3107-33-3 ]
YieldReaction ConditionsOperation in experiment
70%
Stage #1: With potassium phosphate; N,N'-bis(2,5-dimethylpyrrol-1-yl)oxalamide; cetyltrimethylammonim bromide; copper(I) bromide In water at 110℃; for 0.166667 h; Sealed tube; Inert atmosphere
Stage #2: With hydrazine hydrate In water at 110℃; for 1 h; Sealed tube; Inert atmosphere
Stage #3: With hydrogenchloride In dichloromethane; water
General procedure: CuBr (36 mg, 0.25 mmol, 2.5 mol percent), L3 (110 mg, 0.4 mmol,4 mol percent), H2O (0.5 mL), and K3PO4 (254 mg, 1.2 mmol) were mixedin a 15 mL screw cap test tube. After STAC (110 mg, 0.3 mmol,3 mol percent) and aryl bromide (10 mmol) were added, the resulting mixture was stirred at 80-110° C (bath temperature) for 10 min.Then K3PO4 (2.29 g, 10.8 mmol) and N2H4*H2O (1 g, 20 mmol) were added and argon (flow rate 5-7 mL/min) was bubbled through thereaction mixture for 5 min.28 The reaction mixture was stirred ina closed test tube at 80-110° C (bath temperature) for 1-2 h until complete consumption of starting material was observed as monitoredby TLC (eluentehexane), then cooled to room temperatureand diluted with SH2Cl2 (50 mL). The resulting solutionwas filteredand washed with brine (225 mL). Aq HCl (37percent) was added to the CH2Cl2 solution dropwise until pH 3-4. The formed precipitate was filtered, washed with SH2Cl2 (15 mL) and dried atroom temperature. NMR spectra of certain synthesized aryl hydrazine hydrochlorides showed that they contained 1-5 mol percent of the corresponding aniline hydrochlorides as impurities (see Supplementary data). Analytical samples of aryl hydrazine hydrochlorides were purified via precipitation from methanol solution by adding 2-3 volumes of diethyl ether.
Reference: [1] Chinese Journal of Chemistry, 2018, vol. 36, # 11, p. 1003 - 1006
[2] Tetrahedron, 2014, vol. 70, # 26, p. 4043 - 4048
  • 26
  • [ 401-78-5 ]
  • [ 1423-26-3 ]
Reference: [1] Organic Letters, 2014, vol. 16, # 5, p. 1494 - 1497
  • 27
  • [ 401-78-5 ]
  • [ 124-38-9 ]
  • [ 177420-64-3 ]
Reference: [1] European Journal of Organic Chemistry, 2006, # 3, p. 729 - 734
  • 28
  • [ 401-78-5 ]
  • [ 481075-58-5 ]
Reference: [1] European Journal of Organic Chemistry, 2002, # 15, p. 2508 - 2517
[2] Journal of the American Chemical Society, 2002, vol. 124, # 29, p. 8514 - 8515
  • 29
  • [ 401-78-5 ]
  • [ 481075-59-6 ]
Reference: [1] European Journal of Organic Chemistry, 2002, # 15, p. 2508 - 2517
  • 30
  • [ 401-78-5 ]
  • [ 328-67-6 ]
Reference: [1] European Journal of Organic Chemistry, 2002, # 15, p. 2508 - 2517
  • 31
  • [ 401-78-5 ]
  • [ 1005450-55-4 ]
Reference: [1] Journal of Organic Chemistry, 2011, vol. 76, # 7, p. 2187 - 2194
[2] Journal of Organic Chemistry, 2011, vol. 76, # 7, p. 2187 - 2194
Recommend Products
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 401-78-5 ]

Fluorinated Building Blocks

Chemical Structure| 401-84-3

[ 401-84-3 ]

1,3-Dibromo-5-(trifluoromethyl)benzene

Similarity: 0.98

Chemical Structure| 402-43-7

[ 402-43-7 ]

1-Bromo-4-(trifluoromethyl)benzene

Similarity: 0.98

Chemical Structure| 7657-08-1

[ 7657-08-1 ]

1,2-Dibromo-4-(trifluoromethyl)benzene

Similarity: 0.95

Chemical Structure| 7657-09-2

[ 7657-09-2 ]

1,4-Dibromo-2-(trifluoromethyl)benzene

Similarity: 0.95

Chemical Structure| 29848-59-7

[ 29848-59-7 ]

1-Bromo-3-(difluoromethyl)benzene

Similarity: 0.95

Aryls

Chemical Structure| 401-84-3

[ 401-84-3 ]

1,3-Dibromo-5-(trifluoromethyl)benzene

Similarity: 0.98

Chemical Structure| 402-43-7

[ 402-43-7 ]

1-Bromo-4-(trifluoromethyl)benzene

Similarity: 0.98

Chemical Structure| 7657-08-1

[ 7657-08-1 ]

1,2-Dibromo-4-(trifluoromethyl)benzene

Similarity: 0.95

Chemical Structure| 7657-09-2

[ 7657-09-2 ]

1,4-Dibromo-2-(trifluoromethyl)benzene

Similarity: 0.95

Chemical Structure| 29848-59-7

[ 29848-59-7 ]

1-Bromo-3-(difluoromethyl)benzene

Similarity: 0.95

Bromides

Chemical Structure| 401-84-3

[ 401-84-3 ]

1,3-Dibromo-5-(trifluoromethyl)benzene

Similarity: 0.98

Chemical Structure| 402-43-7

[ 402-43-7 ]

1-Bromo-4-(trifluoromethyl)benzene

Similarity: 0.98

Chemical Structure| 7657-08-1

[ 7657-08-1 ]

1,2-Dibromo-4-(trifluoromethyl)benzene

Similarity: 0.95

Chemical Structure| 7657-09-2

[ 7657-09-2 ]

1,4-Dibromo-2-(trifluoromethyl)benzene

Similarity: 0.95

Chemical Structure| 29848-59-7

[ 29848-59-7 ]

1-Bromo-3-(difluoromethyl)benzene

Similarity: 0.95

Trifluoromethyls

Chemical Structure| 401-84-3

[ 401-84-3 ]

1,3-Dibromo-5-(trifluoromethyl)benzene

Similarity: 0.98

Chemical Structure| 402-43-7

[ 402-43-7 ]

1-Bromo-4-(trifluoromethyl)benzene

Similarity: 0.98

Chemical Structure| 7657-08-1

[ 7657-08-1 ]

1,2-Dibromo-4-(trifluoromethyl)benzene

Similarity: 0.95

Chemical Structure| 7657-09-2

[ 7657-09-2 ]

1,4-Dibromo-2-(trifluoromethyl)benzene

Similarity: 0.95

Chemical Structure| 335013-18-8

[ 335013-18-8 ]

4-Bromo-1-(bromomethyl)-2-(trifluoromethyl)benzene

Similarity: 0.93