Home Cart Sign in  
Chemical Structure| 660845-30-7 Chemical Structure| 660845-30-7

Structure of 660845-30-7

Chemical Structure| 660845-30-7

*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 [ 660845-30-7 ]

CAS No. :660845-30-7
Formula : C6H5ClF2N2O
M.W : 194.57
SMILES Code : O=CC1=C(Cl)N(C)N=C1C(F)F
MDL No. :MFCD12827692
InChI Key :NMYPMEAFQUDCSC-UHFFFAOYSA-N
Pubchem ID :19754692

Safety of [ 660845-30-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P261-P280-P305+P351+P338

Computational Chemistry of [ 660845-30-7 ] Show Less

Physicochemical Properties

Num. heavy atoms 12
Num. arom. heavy atoms 5
Fraction Csp3 0.33
Num. rotatable bonds 2
Num. H-bond acceptors 4.0
Num. H-bond donors 0.0
Molar Refractivity 38.95
TPSA ?

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

34.89 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.56
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

1.31
Log Po/w (WLOGP)?

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

2.34
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.

0.97
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

2.03
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.64

Water Solubility

Log S (ESOL):?

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

-2.05
Solubility 1.74 mg/ml ; 0.00895 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.

-1.64
Solubility 4.42 mg/ml ; 0.0227 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

-1.97
Solubility 2.07 mg/ml ; 0.0106 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

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.

-6.56 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

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)

1.89

Application In Synthesis of [ 660845-30-7 ]

* 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 [ 660845-30-7 ]

[ 660845-30-7 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 660845-30-7 ]
  • [ 1202993-11-0 ]
YieldReaction ConditionsOperation in experiment
3.2 g With dihydrogen peroxide; sodium hydroxide In water; toluene at 37 - 50℃; for 7 h; In a 500 ml flask, 6.0 g (31 mmol) of 5-chloro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbaldehyde are added to 30 ml of toluene. A solution of 2.4 g (62 mmol) of sodium hydroxide in 6 ml of water is added to the reaction mixture, followed by 103 ml of a 30percent solution of hydrogen peroxide in water, whilst keeping the temperature below 37° C. After the end of the addition, the reaction mixture is stirred at 50° C. for 7 hours. Once the reaction mixture is back to room temperature, the two phases are separated and the organic phase is extracted with 100 ml of water. The combined aqueous phases are acidified to pH 2 with aqueous hydrochloric acid. The resulting white precipitate is filtered, washed twice with 20 ml of water, and dried to yield 3.2 g of 5-chloro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm: 3.78 (s, 3H); 7.12 (t, 1H, JHF=53.60 Hz); 13.19 (s, 1H); IR (KBr): 1688 cm-1 (C=O); 2200-3200 cm-1 broad (hydrogen bond).
40 g With copper(II) oxide; sodium hydroxide In water at 25 - 30℃; for 15 h; In 1000 mL reaction flask, 38.9g 3- difluoromethyl-1-methyl-5-chloro-4-carbaldehyde and 390ml of water, 8.4g of sodium hydroxide was added, followed by stirring, 1g of nano copper oxide, control of the reaction temperature is 25-30 ° C, air through an oxidation reaction 15 hours, starting material HPLC i.e.3- difluoromethyl-1-methyl-5-chloro-4-carbaldehyde , less than the total amount of an amount of 0.2percent; the reaction was stopped by filtration, recovery of copper catalyst. The reaction mixture was cooled to below 10 ° C, add 31percent hydrochloric acid to a pH of 1-2, the precipitated solid was filtered; the solid was washed with a small amount of water; and dried to give the product 3-methyl-5-fluoro-1- chloro-pyrazole-4-carboxylic acid 40g, HPLC content 99percent; LC-MS: m / e = 210.
References: [1] Patent: EP2251331, 2010, A1, . Location in patent: Page/Page column 24.
[2] Patent: WO2011/151369, 2011, A1, . Location in patent: Page/Page column 63.
[3] Patent: WO2011/151370, 2011, A1, . Location in patent: Page/Page column 90.
[4] Patent: WO2012/52491, 2012, A2, . Location in patent: Page/Page column 43.
[5] Patent: WO2012/52490, 2012, A1, . Location in patent: Page/Page column 68.
[6] Patent: WO2012/59497, 2012, A1, . Location in patent: Page/Page column 63.
[7] Patent: WO2012/65945, 2012, A1, . Location in patent: Page/Page column 57-58.
[8] Patent: WO2012/65932, 2012, A1, . Location in patent: Page/Page column 24.
[9] Patent: WO2012/65944, 2012, A1, . Location in patent: Page/Page column 55.
[10] Patent: WO2012/65947, 2012, A1, . Location in patent: Page/Page column 61-62.
[11] Patent: US2013/210864, 2013, A1, . Location in patent: Paragraph 0314.
[12] Patent: CN103787977, 2016, B, . Location in patent: Paragraph 0015; 0016.
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 660845-30-7 ]

Fluorinated Building Blocks

Chemical Structure| 1202993-11-0

A170478 [1202993-11-0]

5-Chloro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid

Similarity: 0.89

Chemical Structure| 176969-34-9

A104307 [176969-34-9]

3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid

Similarity: 0.70

Chemical Structure| 1001020-14-9

A215484 [1001020-14-9]

3-(Trifluoromethyl)-1H-pyrazole-4-carbaldehyde

Similarity: 0.70

Chemical Structure| 113100-53-1

A112969 [113100-53-1]

1-Methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid

Similarity: 0.69

Chemical Structure| 141573-95-7

A197104 [141573-95-7]

Ethyl 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate

Similarity: 0.66

Chlorides

Chemical Structure| 1202993-11-0

A170478 [1202993-11-0]

5-Chloro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid

Similarity: 0.89

Chemical Structure| 27006-76-4

A120534 [27006-76-4]

5-Chloro-1,3-dimethyl-1H-pyrazole-4-carbaldehyde

Similarity: 0.84

Chemical Structure| 131797-35-8

A233804 [131797-35-8]

5-Chloro-3-(trifluoromethyl)-1H-pyrazole

Similarity: 0.65

Chemical Structure| 56984-32-8

A232392 [56984-32-8]

Ethyl 5-chloro-1-methyl-1H-pyrazole-4-carboxylate

Similarity: 0.63

Chemical Structure| 111493-52-8

A123018 [111493-52-8]

5-Chloro-1-methyl-1H-pyrazole-4-carbonitrile

Similarity: 0.58

Aldehydes

Chemical Structure| 27006-76-4

A120534 [27006-76-4]

5-Chloro-1,3-dimethyl-1H-pyrazole-4-carbaldehyde

Similarity: 0.84

Chemical Structure| 1001020-14-9

A215484 [1001020-14-9]

3-(Trifluoromethyl)-1H-pyrazole-4-carbaldehyde

Similarity: 0.70

Chemical Structure| 25016-12-0

A123145 [25016-12-0]

1,3-Dimethyl-1H-pyrazole-4-carbaldehyde

Similarity: 0.64

Chemical Structure| 2644-93-1

A108703 [2644-93-1]

1,3,5-Trimethyl-1H-pyrazole-4-carbaldehyde

Similarity: 0.57

Chemical Structure| 112758-40-4

A134380 [112758-40-4]

3-Methyl-1H-pyrazole-4-carbaldehyde

Similarity: 0.56

Difluoromethyls

Chemical Structure| 1202993-11-0

A170478 [1202993-11-0]

5-Chloro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid

Similarity: 0.89

Chemical Structure| 176969-34-9

A104307 [176969-34-9]

3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid

Similarity: 0.70

Chemical Structure| 141573-95-7

A197104 [141573-95-7]

Ethyl 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate

Similarity: 0.66

Chemical Structure| 1089212-38-3

A171677 [1089212-38-3]

4-Bromo-3-(difluoromethyl)-1-methyl-1H-pyrazole

Similarity: 0.53

Related Parent Nucleus of
[ 660845-30-7 ]

Pyrazoles

Chemical Structure| 1202993-11-0

A170478 [1202993-11-0]

5-Chloro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid

Similarity: 0.89

Chemical Structure| 27006-76-4

A120534 [27006-76-4]

5-Chloro-1,3-dimethyl-1H-pyrazole-4-carbaldehyde

Similarity: 0.84

Chemical Structure| 176969-34-9

A104307 [176969-34-9]

3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid

Similarity: 0.70

Chemical Structure| 1001020-14-9

A215484 [1001020-14-9]

3-(Trifluoromethyl)-1H-pyrazole-4-carbaldehyde

Similarity: 0.70

Chemical Structure| 113100-53-1

A112969 [113100-53-1]

1-Methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid

Similarity: 0.69