Home Cart Sign in  
Chemical Structure| 877131-92-5 Chemical Structure| 877131-92-5

Structure of 877131-92-5

Chemical Structure| 877131-92-5

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 877131-92-5 ]

CAS No. :877131-92-5
Formula : C9H5BrF3N
M.W : 264.04
SMILES Code : N#CCC1=CC=C(Br)C=C1C(F)(F)F
MDL No. :MFCD13185431
InChI Key :DSDNDRQVAPPETF-UHFFFAOYSA-N
Pubchem ID :58488407

Safety of [ 877131-92-5 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 877131-92-5 ] Show Less

Physicochemical Properties

Num. heavy atoms 14
Num. arom. heavy atoms 6
Fraction Csp3 0.22
Num. rotatable bonds 2
Num. H-bond acceptors 4.0
Num. H-bond donors 0.0
Molar Refractivity 48.67
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

23.79 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

2.11
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

3.15
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

4.69
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

3.51
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

3.85
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

3.46

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-3.65
Solubility 0.0596 mg/ml ; 0.000226 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-3.32
Solubility 0.127 mg/ml ; 0.000479 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-4.63
Solubility 0.0062 mg/ml ; 0.0000235 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Moderately soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

Yes
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

Yes
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-5.67 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

1.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

0.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<0.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

1.83

Application In Synthesis of [ 877131-92-5 ]

* 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.

  • Downstream synthetic route of [ 877131-92-5 ]

[ 877131-92-5 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 335013-18-8 ]
  • [ 151-50-8 ]
  • [ 877131-92-5 ]
YieldReaction ConditionsOperation in experiment
In methanol; at 80.0℃; for 0.333333h;Microwave irradiation; Step 2: r4-bromo-2-(trifluoromethyl)phenyH acetonitrile; A mixture of the benzyl bromide (1 eq.) from step 1 and KCN (1.1 eq.) in MeOH (0.32M) was subjected microwave (Smith Creator; Personal Chemistry),) for 20min at 8O0C. The mixture was cooled down to room temperature, concentrated and purification by column chromatography on silica gel, eluting with Hex/EtOAc 5%, afforded the title compound III.2 as an off-white solid.
  • 2
  • [ 877131-92-5 ]
  • [ 107-04-0 ]
  • [ 877131-96-9 ]
YieldReaction ConditionsOperation in experiment
86% To a stirred solution of <strong>[877131-92-5](4-bromo-2-trifluoromethyl-phenyl)-acetonitrile</strong> (3.33 g, 12.61 mmol) from step 2 of example A(141), benzyltriethylammoniym chloride (0.057 g, 0.25 mmol) and 1-bromo-2-chloroethane (1.57 g, 10.94 mmol), was added dropwise a solution of NaOH 40% ( 3 ml_). The reaction mixture was stirred 6 hours at 50 C. After this time the reaction was quenched with 1 N HCI (30 ml) and extracted with EtOAC (3 x 30 ml_). The organic phase was dried over Na2SO4 and evaporated. The crude organic product was purified by flash column chromatography (10% EtOAc in hexanes) to give the product (3.1 g, 86%) as a clear oil. 1H NMR (400 MHz, CDCI3) 6 1.4-1.44 (m, 2H), 1.76-1.80 (m, 2H), 7.44 (d, J=8.3 Hz, 1 H), 7.69 (dd,J=8.3, 2 Hz, 1 H), 7.84 (d, J=2 Hz, 1 H).
  • 3
  • [ 86845-27-4 ]
  • [ 151-50-8 ]
  • [ 877131-92-5 ]
YieldReaction ConditionsOperation in experiment
54% With tetrabutylammomium bromide; In dichloromethane; water; at 20.0℃; for 4.0h; A mixture of 4-methyl-3-trifluorobromobenzene (33.26 g, 104.261 mmol) from step 1 above , KCN (20.43 g, 313.67 mmol) and tetrabutylammonium bromide (3.37 g, 10.45 mmol) in CH2CI2/H2O 1:1 (300 mL) was stirred at room temperature for 4 hours. The layers were separated and the organic layer washed with H2O (100 ml_) 1N HCI (100 ml_), brine, dried over Na2SO4 and then concentrated to a brown oil which was purified by flash column chromatography (0% to 20% EtOAc in hexanes) to give the product as a clear oil (14.9 g, 54%). 1H NMR (400 MHz, CDCI3) 6 3.91 (s, 2H), 7.57 (d, J=8.3 Hz, 1 H), 7.75 (dd, J=8.3, 2 Hz, 1 H), 7.84 (d, J=2 Hz, 1 H).
  • 4
  • [ 877131-92-5 ]
  • methyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(trifluoromethyl)phenyl)acetate [ No CAS ]
  • 5
  • [ 877131-92-5 ]
  • methyl 2-(4-bromo-2-(trifluoromethyl)phenyl)acetate [ No CAS ]
  • 6
  • [ 877131-92-5 ]
  • 2-(4-bromo-2-(trifluoromethyl)phenyl)acetic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
89.5% With hydrogenchloride; acetic acid; at 100.0℃; for 2.0h;Inert atmosphere; Add hydrochloric acid (2 mL, 12M) to a solution of 2-[ 4-bromo-2(trifluoromethyl)phenyl]acetonitrile (600 mg, 2.25 mmol) in acetic acid (2 mL), the mixture is stirred at 100 C for 2 h under nitrogen. The reaction mixture is concentrated to afford title 5 compound (600 mg, 89.5%) as colorless oil. 1H NMR (400MHz, CD3Cl) () = 7.82 (d, J = 1.6 Hz, 1H), 7.67 (dd, J = 1.6, 8.4 Hz, 1H), 7.29 (s, 1H), 3.83 (s, 2H).
With sulfuric acid; acetic acid; In water; at 110.0℃;Inert atmosphere; A mixture of <strong>[877131-92-5]2-(4-bromo-2-(trifluoromethyl)phenyl)acetonitrile</strong> (2.385 g, 9.03 mmol), water (8.5 mL), 95%sulfuric acid (9.5 mL) and acetic acid (6.5 mL) is heated to 110C, under nitrogen, overnight. The RM isallowed to cool to RT and is poured onto ice/water. The mixture is extracted three times with DCM and the combined organic layers are washed with brine, dried over anh. MgSO4, filtered and concentrated under reduced pressure affording crude 2-(4-bromo-2-(trifluoromethyl)phenyl)acetic acid as a light yellow solid (2.694 g, quantitative). LC-MS B: tR = 0.85 mm; no ionization.
  • 7
  • [ 773837-37-9 ]
  • [ 1214350-42-1 ]
  • [ 877131-92-5 ]
YieldReaction ConditionsOperation in experiment
92% In water; acetonitrile; at 80.0℃;Inert atmosphere; A solution of 4-bromo-1-(chloromethyl)-2-(trifluoromethyl)benzene (2.707 g, 9.81 mmol) in MeCN (32 mL) and water (4 mL) is treated with sodium cyanide (0.651 g, 12.80 mmol) and the mixture is heated to 80C, under nitrogen, overnight. The RM is allowed to cool to RT and is diluted with water. Acetonitrile is removedunder reduced pressure and the mixture is extracted twice with DCM. The combined organic layers are dried over anh. MgSO4, filtered and concentrated under reduced pressure. Purification by FC (from heptane to heptane/EtOAc = 7/3) affords 2-(4-bromo-2-(trifluoromethyl)phenyl)acetonitrile as a light yellow solid (2.385 g, 92%). LC-MS B: tR = 0.95 mm; no ionization.
  • 8
  • (4-bromo-2-(trifluoromethyl)phenyl)methanol [ No CAS ]
  • [ 877131-92-5 ]
  • 9
  • [ 877131-92-5 ]
  • ethyl 1-[4-bromo-2-(trifluoromethyl)phenyl]cyclopropanecarboxylate [ No CAS ]
  • 10
  • [ 877131-92-5 ]
  • ethyl 1-[4-[6-(5-amino-1-methyl-pyrazol-4-yl)-3-pyridyl]-2-(trifluoromethyl)phenyl]cyclopropanecarboxylate [ No CAS ]
  • 11
  • [ 877131-92-5 ]
  • ethyl 1-[4-[6-[5-[[6-(cyclopropoxy)pyrazin-2-yl]amino]-1-methyl-pyrazol-4-yl]-3-pyridyl]-2-(trifluoromethyl)phenyl]cyclopropanecarboxylate [ No CAS ]
  • 12
  • [ 877131-92-5 ]
  • ethyl 2-[4-bromo-2-(trifluoromethyl)phenyl]acetate [ No CAS ]
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 877131-92-5 ]

Fluorinated Building Blocks

Chemical Structure| 320-29-6

A190590 [320-29-6]

4-Bromo-1,2-bis(trifluoromethyl)benzene

Similarity: 0.84

Chemical Structure| 691877-03-9

A152031 [691877-03-9]

3-Bromo-5-(trifluoromethyl)benzonitrile

Similarity: 0.83

Chemical Structure| 191165-13-6

A179986 [191165-13-6]

4-Bromo-2-(trifluoromethyl)benzonitrile

Similarity: 0.83

Chemical Structure| 69902-83-6

A446811 [69902-83-6]

1-Bromo-2-methyl-3-(trifluoromethyl)benzene

Similarity: 0.80

Chemical Structure| 1000994-95-5

A706627 [1000994-95-5]

1-Bromo-4-(1,1-difluoroethyl)benzene

Similarity: 0.80

Aryls

Chemical Structure| 320-29-6

A190590 [320-29-6]

4-Bromo-1,2-bis(trifluoromethyl)benzene

Similarity: 0.84

Chemical Structure| 691877-03-9

A152031 [691877-03-9]

3-Bromo-5-(trifluoromethyl)benzonitrile

Similarity: 0.83

Chemical Structure| 191165-13-6

A179986 [191165-13-6]

4-Bromo-2-(trifluoromethyl)benzonitrile

Similarity: 0.83

Chemical Structure| 69902-83-6

A446811 [69902-83-6]

1-Bromo-2-methyl-3-(trifluoromethyl)benzene

Similarity: 0.80

Chemical Structure| 1000994-95-5

A706627 [1000994-95-5]

1-Bromo-4-(1,1-difluoroethyl)benzene

Similarity: 0.80

Bromides

Chemical Structure| 320-29-6

A190590 [320-29-6]

4-Bromo-1,2-bis(trifluoromethyl)benzene

Similarity: 0.84

Chemical Structure| 691877-03-9

A152031 [691877-03-9]

3-Bromo-5-(trifluoromethyl)benzonitrile

Similarity: 0.83

Chemical Structure| 191165-13-6

A179986 [191165-13-6]

4-Bromo-2-(trifluoromethyl)benzonitrile

Similarity: 0.83

Chemical Structure| 69902-83-6

A446811 [69902-83-6]

1-Bromo-2-methyl-3-(trifluoromethyl)benzene

Similarity: 0.80

Chemical Structure| 1000994-95-5

A706627 [1000994-95-5]

1-Bromo-4-(1,1-difluoroethyl)benzene

Similarity: 0.80

Nitriles

Chemical Structure| 691877-03-9

A152031 [691877-03-9]

3-Bromo-5-(trifluoromethyl)benzonitrile

Similarity: 0.83

Chemical Structure| 191165-13-6

A179986 [191165-13-6]

4-Bromo-2-(trifluoromethyl)benzonitrile

Similarity: 0.83

Chemical Structure| 1735-53-1

A157462 [1735-53-1]

4-Bromo-3-(trifluoromethyl)benzonitrile

Similarity: 0.79

Chemical Structure| 1483-55-2

A288374 [1483-55-2]

2-Bromo-5-(trifluoromethyl)benzonitrile

Similarity: 0.79

Chemical Structure| 35764-15-9

A179463 [35764-15-9]

2-Bromo-4-(trifluoromethyl)benzonitrile

Similarity: 0.77

Trifluoromethyls

Chemical Structure| 320-29-6

A190590 [320-29-6]

4-Bromo-1,2-bis(trifluoromethyl)benzene

Similarity: 0.84

Chemical Structure| 691877-03-9

A152031 [691877-03-9]

3-Bromo-5-(trifluoromethyl)benzonitrile

Similarity: 0.83

Chemical Structure| 191165-13-6

A179986 [191165-13-6]

4-Bromo-2-(trifluoromethyl)benzonitrile

Similarity: 0.83

Chemical Structure| 69902-83-6

A446811 [69902-83-6]

1-Bromo-2-methyl-3-(trifluoromethyl)benzene

Similarity: 0.80

Chemical Structure| 402-43-7

A180575 [402-43-7]

1-Bromo-4-(trifluoromethyl)benzene

Similarity: 0.80