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Chemical Structure| 367-30-6 Chemical Structure| 367-30-6

Structure of 367-30-6

Chemical Structure| 367-30-6

2,5-Difluoroaniline

CAS No.: 367-30-6

4.5 *For Research Use Only !

Cat. No.: A168447 Purity: 98%

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Product Details of [ 367-30-6 ]

CAS No. :367-30-6
Formula : C6H5F2N
M.W : 129.11
SMILES Code : C1=C(F)C=CC(=C1N)F
MDL No. :MFCD00007651
InChI Key :YNOOQIUSYGWMSS-UHFFFAOYSA-N
Pubchem ID :67775

Safety of [ 367-30-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302+H312+H332-H317-H227
Precautionary Statements:P264-P270-P271-P272-P280-P301+P312+P330-P302+P352+P312-P304+P340+P312-P333+P313-P370+P378-P403+P235-P501

Computational Chemistry of [ 367-30-6 ] Show Less

Physicochemical Properties

Num. heavy atoms 9
Num. arom. heavy atoms 6
Fraction Csp3 0.0
Num. rotatable bonds 0
Num. H-bond acceptors 2.0
Num. H-bond donors 1.0
Molar Refractivity 30.76
TPSA ?

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

26.02 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.47
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

1.54
Log Po/w (WLOGP)?

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

2.4
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.

2.34
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

1.99
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.95

Water Solubility

Log S (ESOL):?

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

-2.1
Solubility 1.02 mg/ml ; 0.00787 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.

-1.7
Solubility 2.6 mg/ml ; 0.0202 mol/l
Class?

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

Very 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

-2.56
Solubility 0.357 mg/ml ; 0.00277 mol/l
Class?

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

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

No
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.

-5.99 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

2.0
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

1.0 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<1.0
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)

1.0

Application In Synthesis of [ 367-30-6 ]

* 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 [ 367-30-6 ]

[ 367-30-6 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 367-30-6 ]
  • [ 108-24-7 ]
  • [ 398-90-3 ]
YieldReaction ConditionsOperation in experiment
100% In dichloromethane; at 20.0℃; Example 1 Synthesis of N-(2,5-difluorophenyl)acetamide 11 To a solution of 2,5-difluoroaniline 10 (30.72 g, 238 mmol) in 100 ml of dichloromethane was added acetic anhydride (29.15 g, 285 mmol) at room temperature. The resulting mixture was stirred at room temperature overnight. The volatile solvent was evaporated, and water (200 ml) was added. A white solid was collected by filtration and dried in vacuum, giving the desired product 11 as a white solid, 40 g (100%). 1H NMR (300 MHZ, CDCl3) δ 8.16 (m, 1H), 7.42 (brs, 1H), 7.01 (m, 1H), 6.72 (m, 1H), 2.22 (s, 3H).
92.8% In dichloromethane; at 20.0℃; for 16.0h; To a solution of compound 3.1 (10.0 g, 77.46 mmol, 1 equiv) in dichloromethane (35 mL) was added AC2O (9.47 g, 92.75 mmol, 8.69 mL, 1.20 equiv) in portions at 20 C. After addition was complete, the reaction mixture was stirred at 20 C for 16 hr. LC-MS showed compound 1 consumed, and the main product was compound 3.2 (r.t. = 0.626 min, [M+H]+ = 171.8). The reaction mixture was concentrated under reduced pressure. Then water (80 mL) was added to the residue and an off-white solid was collected by filtration and dried under vacuum to give compound 3.2 (12.3 g, 71.87 mmol, 92.8% yield). NMR (400 MHz, CDCb) d 8.23 - 8.12 (m, 1H), 7.46 (br s, 1H), 7.03 (dt, J = 4.8, 9.8 Hz, 1H), 6.72 (br t, J = 8.2 Hz, 1H), 2.24 (s, 3H).
  • 2
  • [ 367-30-6 ]
  • [ 140-89-6 ]
  • [ 155559-81-2 ]
YieldReaction ConditionsOperation in experiment
76.5% In N,N-dimethyl-formamide; at 120℃; for 10h; Step 1) Synthesis of 5-fluorobenzo [d] thiazole-2-thiol 2, 5-Difluoroaniline (1.00 g, 7.75 mmol) and potassium ethylxanthate (2.73 g, 17.05 mmol) were added into N, N-dimethylformamide (50 mL) in turn, the mixture was heated at 120 ? for 10 h. After the reaction is complete, the mixture was cooled to rt and diluted with water (100 mL) . The resulting mixture was adjusted with hydrochloric acid (1 M) to pH 4 to 5. Some solid precipitated, the mixture was filtered by suction. The solid was dried at 50 ? under a vacuum to give the title compound as a white solid (1.11 g, 76.5%) .MS (ESI, pos. ion) m/z: 185.00 [M+H] +; and1H NMR (DMSO-d6, 600 MHz) ? (ppm) : 13.98 (s, 1H) , 7.55 (d, J = 8.2 Hz, 1H) , 7.36~7.31 (m, 2H) .
67% In N,N-dimethyl-formamide; at 120℃; for 0.25h;microwave; A mixture of 2,5-difluoro-phenylamine (129 mg, 1 mmol) and potassium o-ethyl dithiocarbonate (352 mg, 2.2 mmol) in DMF (5 mL) was heated to 120C for 15 min in microwave. The reaction mixture was cooled, diluted with 10 mL of ice water, and acidified with 3 mL of HCI solution (1 mol/L). Then the mixture was extracted with EtOAc (3 x 50 mL), washed with brine and dried over Na2SO/i. The dried organic layers were concentrated to give 5- fluorobenzo[d]thiazole-2-thiol (120 mg, 0.67 mmol, 67%). ESI-MS (M+l): 185 calc. for
40% In N,N-dimethyl-formamide; for 4h;Inert atmosphere; Heating; General procedure: GP3-1: A solution of 2-halo substituted aniline (1.0 eq), potassium ethyl xanthate (1.2 eq or 2.2 eq,typically 2.2 eq) in 10 volume of anhydrous DMF was heated at 100 0Cor 120 0C for 4 hours under nitrogen. TLC monitored the progress ofreaction. After completion, the reaction mixture was cooled to room temperature,diluted with water (10 volume) and neutralized by 1 M HCl solution to pH 5. Theformed precipitate was collected by filtration, rinsed with water, firstlydried by rotavapor, and then dried by oil pump to afford 2-mercaptobenzothiazole.GP3-2: 2-mercaptobenzothiazole in 10 volume ofanhydrous DCM, was added by sulfuryl chloride (SO2Cl2, 1volume) under ice-cooled condition. The mixture was stirred at rt for 1 hour,which was monitored by TLC. After consumption of starting material, the mixturewas diluted by 30 volume of ether, following quenching carefully by addingwater. Stirring was kept for 1 hour to make sure the SO2Cl2was totally consumed and product was released. Organic layer was collected,neutralized by saturated NaHCO3, dried over Na2SO4and purified by silica gel chromatograph to give the pure product, which wasfinally characterized by LC-MS and NMR.
  • 3
  • [ 367-30-6 ]
  • [ 398-90-3 ]
YieldReaction ConditionsOperation in experiment
With acetic anhydride; In benzene; REFERENCE EXAMPLE 14 Preparation of 2,5-difluoro-4-nitroacetanilide STR43 20.5 g of 2,5-difluoroaniline was dissolved in 68 ml of benzene, and 17.8 g of acetic anhydride was dropwise added. Fifteen hours later, benzene was distilled off, and the residue was washed with ethyl ether to obtain 25.6 g of 2,5-difluoroacetanilide as white crystals.
  • 4
  • [ 367-30-6 ]
  • [ 75-36-5 ]
  • [ 398-90-3 ]
  • 6
  • [ 21512-16-3 ]
  • [ 367-30-6 ]
  • C12H8F2N2S [ No CAS ]
 

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