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Chemical Structure| 125652-55-3 Chemical Structure| 125652-55-3
Chemical Structure| 125652-55-3

1-Butyl-3-methylpyridinium Chloride

CAS No.: 125652-55-3

4.5 *For Research Use Only !

Cat. No.: A287216 Purity: 98%

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Product Details of [ 125652-55-3 ]

CAS No. :125652-55-3
Formula : C10H16ClN
M.W : 185.69
SMILES Code : CC1=C[N+](CCCC)=CC=C1.[Cl-]
MDL No. :MFCD08458942
InChI Key :PHCASOSWUQOQAG-UHFFFAOYSA-M
Pubchem ID :19876500

Safety of [ 125652-55-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319
Precautionary Statements:P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313

Calculated chemistry of [ 125652-55-3 ] Show Less

Physicochemical Properties

Num. heavy atoms 12
Num. arom. heavy atoms 6
Fraction Csp3 0.5
Num. rotatable bonds 3
Num. H-bond acceptors 0.0
Num. H-bond donors 0.0
Molar Refractivity 55.27
TPSA ?

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

3.88 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

3.33
Log Po/w (WLOGP)?

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

-0.91
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.

2.39
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

2.44
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.14

Water Solubility

Log S (ESOL):?

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

-3.26
Solubility 0.102 mg/ml ; 0.000548 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.

-3.09
Solubility 0.152 mg/ml ; 0.000816 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

-3.17
Solubility 0.125 mg/ml ; 0.000671 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

Low
BBB permeant?

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

No
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.

-5.07 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)

1.29

Application In Synthesis of [ 125652-55-3 ]

* 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.

  • Downstream synthetic route of [ 125652-55-3 ]

[ 125652-55-3 ] Synthesis Path-Downstream   1~19

  • 1
  • [ 108-99-6 ]
  • [ 109-69-3 ]
  • [ 125652-55-3 ]
YieldReaction ConditionsOperation in experiment
In toluene; at 20 - 130℃;Inert atmosphere; General procedure: The used method was modified to increase the product yield: alkyl halide (0.2000 mol) was added into two-neck round-bottom flask with the solution of 3-substituted pyridine (0.1665 mol) in toluene (20 ml). The solution was then stirred using a magnetic stirrer under a nitrogen atmosphere for 1 h at room temperature. After that the reaction mixture has been stirred at 110-130 C for 24-48 h to reflux condenser plant without access to nitrogen. After the reaction completion the obtained product delaminated; the dense layer of ionic liquid was decanted from the toluene layer. The product was washed with toluene. Recrystallization was carried out by dissolution in acetonitrile followed by precipitation in excess of diethyl ether. Volatile organic compounds have been removed for 6-8 h using the rotary evaporator (Rotavapor R-215, Buechi), at pressure gradual decrease from atmospheric one to 20-120 mbar, and temperature rise from 60 C to 90-140 C.
  • 2
  • [ 125652-55-3 ]
  • [ 1934-75-4 ]
  • [ 712355-12-9 ]
YieldReaction ConditionsOperation in experiment
, wherein said salt is selected from the group consisting of: ... 1-decyl-3-methylimidazolium bromide, 1-dodecyl-3-methylimidazolium chloride, 1-methyl-3-tetradecylimidazolium chloride, 4-methyl-N-butylpyridinium chloride, 3-methyl-N-butylpyridinium chloride, 4-methyl-N-hexylpyridinium chloride, 1-ethyl-3-methylimidazolium tetrafluoroborate, 1-butyl-3-methylimidazolium tetrafluoroborate, ...
  • 4
  • [ 125652-55-3 ]
  • [ 847448-65-1 ]
  • [ 1323126-07-3 ]
  • 5
  • [ 125652-55-3 ]
  • [ 1274452-24-2 ]
  • [ 1331734-78-1 ]
  • 6
  • [ 125652-55-3 ]
  • [ 32586-90-6 ]
  • [ 1331734-68-9 ]
  • 7
  • [ 125652-55-3 ]
  • [ 34723-47-2 ]
  • [ 7646-79-9 ]
  • (N-butyl-3-methylpyridinium)2 Co(dicyanamido)4 [ No CAS ]
  • 8
  • [ 125652-55-3 ]
  • K[HB(CN)3] [ No CAS ]
  • [ 1415416-96-4 ]
  • potassium chloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With water; 8.08 g (62.7 mmol) K[BH(CN)3] dissolved in 35 cm3 of water and 11.63 g (62.6 mmol) of <strong>[125652-55-3]1-butyl-3-methylpyridinium chloride</strong>, [BMPy]CI, dissolved in 18 cm3 of water are mixed together at room temperature. The product, 1- butyl-3-methylpyridinium tricyanohydridoborate is extracted with dichloromethane (100 + 50 + 50 cm3 of CH2CI2). The organic phase is washed two times with water (50 + 50 cm3) and dried with Na2S0 . The solvent is distilled off and the residue is dried in vacuum at ca. 40 C for one day. The yield of liquid at room temperature1-butyl-3-methylpyridinium tricyanohydridoborate, [BMPy] [BH(CN)3], is 13.64 g (91%).1H-NMR (Solvent: Aceton-D6): delta, ppm = 0.991 (CH3> 3H), 3JH,H = 7.5 Hz; 1.45 m (CH2l 2H); 1.74 d (1 H, BH), 1JH.B = 97 Hz; 2.09 m (CH2, 2H); 2.63 s (CH3, 3H), 4.72 t (CH2, 2H), 3JH,H = 7.6 Hz; 8.10 d,d (CH, 1H), 3JH,H = 7.0 Hz; 8.50 d (CH, 1H), 3JH,H = 8.0 Hz; 8.88 d (CH, 1H), 3JH,H = 6.1 Hz; 8.94 s (CH. 1 H).11B-NMR (Solvent: Aceton-D6): o~, ppm = -40.1 d, 1JB,H = 97 Hz.
  • 9
  • [ 125652-55-3 ]
  • [ 88503-36-0 ]
  • [ 1415022-39-7 ]
YieldReaction ConditionsOperation in experiment
90% In water; Example 91-Butyl-3-methylpyridinium dicyanodihydridoborate-[BMPy][BH2(CN)2]4.09 g (46.6 mmol) of sodium dicyanodihydridoborate, Na[BH2(CN)2], and 8.63 g (46.5 mmol) of <strong>[125652-55-3]1-butyl-3-methylpyridinium chloride</strong>, [BMPy]Cl, are each dissolved in 20 ml of water and mixed. The product, 1-butyl-3-methylpyridinium dicyanodihydridoborate, [BMPy][BH2(CN)2], is extracted with 100+100+50 ml of CH2Cl2. The combined organic phases are washed with 50+50 ml of water, dried using Na2SO4, and the solvent is distilled off. [BMPy][BH2(CN)2] is dried at about 40 C. in vacuo for one day with stirring. The yield of 1-butyl-3-methylpyridinium dicyanodihydridoborate is 9.0 g (41.8 mol, 90%). 1H{11B}-NMR (solvent: acetone-D6; reference: TMS): delta, ppm=0.97 t (CH3, 3H), 3JH,H=7.5 Hz; 1.02 s (2H, BH2); 1.44 m (CH2, 2H); 2.08 m (CH2, 2H); 2.63 s (CH3, 3H), 4.71 t (CH2, 2H), 3JH,H=7.6 Hz; 8.08 d, d (CH, 1H), 3JH,H=7.0 Hz; 8.50 d (CH, 1H), 3JH,H=8.1 Hz; 8.88 d (CH, 1H), 3JH,H=6.1 Hz; 8.95 s (CH, 1H). 11B{1H}NMR (solvent: acetone-D6; reference: Et2O.BF3): delta, ppm=-41.7 s
With sodium sulfate; In water; Example 9 1-Butyl-3-methylpyridinium dicyanodihydridoborate-[BMPy][BH2(CN)2] 4.09 g (46.6 mmol) of sodium dicyanodihydridoborate, Na[BH2(CN)2], and 8.63 g (46.5 mmol) of <strong>[125652-55-3]1-butyl-3-methylpyridinium chloride</strong>, [BMPy]Cl, are each dissolved in 20 ml of water and mixed. The product, 1-butyl-3-methylpyridinium dicyanodihydridoborate, [BMPy][BH2(CN)2], is extracted with 100+100+50 ml of CH2Cl2. The combined organic phases are washed with 50+50 ml of water, dried using Na2SO4, and the solvent is distilled off. [BMPy][BH2(CN)2] is dried at about 40 C. in vacuo for one day with stirring. The yield of 1-butyl-3-methylpyridinium dicyanodihydridoborate is 9.0 g (41.8 mol, 90%). 1H{11B}-NMR (solvent: acetone-D6; reference: TMS): delta, ppm=0.97 t (CH3, 3H), 3JH,H=7.5 Hz; 1.02 s (2H, BH2); 1.44 m (CH2, 2H); 2.08 m (CH2, 2H); 2.63 s (CH3, 3H), 4.71 t (CH2, 2H), 3JH,H=7.6 Hz; 8.08 d, d (CH, 1H), 3JH,H=7.0 Hz; 8.50 d (CH, 1H), 3JH,H=8.1 Hz; 8.88 d (CH, 1H), 3JH,H=6.1 Hz; 8.95 s (CH, 1H).
  • 10
  • [ 125652-55-3 ]
  • 1-butyl-3-methyl-pyridinium dichloroiodate [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With Iodine monochloride; In dichloromethane; water; at 0 - 20℃; for 1.0h; A black solution of ICl (3.14g, 19.39 mmol) in dichloromethane (35ml) was added drop wise to an ice cold solution of <strong>[125652-55-3]1-butyl-3-methylpyridinium chloride</strong> (3.0g, 16.16 mmol) in water (16ml) under stirring and then left to attain room temperature. After the reaction mixture was stirred for 1 hour, the dichloromethane layer was separated and dried with sodium sulfate and then evaporated under vacuum to afford water soluble dark reddish brown ionic liquid 1-butyl-3-methylpyridinium dichloroiodate (BMPDCI) in quantitative yields (5.5g, 98%). This ionic liquid was stable and stored in dark at 10 C (in refrigerator) for several months without any change in colour, loss of reactivity and degradation (checked by NMR). 1H NMR (200 MHz, DMSO-d6 delta/ppm): 9.03 (s, 1H, Ar-H), 8.97 (d, 1H, 7=5.94 Hz, Ar-H), 8.51 (d, 1H, 7=7.96 Hz, Ar-H), 8.10 (dd, 1H, 7=1.37 Hz, 8.42 Hz, Ar-H), 4.59 (t, 2H, CH2), 2.56 (s, 3H, Ar-CH3), 2.03-1.88 (m, 2H, -CH2-CH2), 1.40-1.29 (m, 2H, CH2-CH3) 0.97 (t, 3H,CH3). 13C NMR (50 MHz, CDCl3+DMS0-d6): 12.23, 17.50, 18.13, 32.17, 60.56, 126.69, 138.72, 140.57, 142.91, 144.88.
  • 11
  • [ 125652-55-3 ]
  • 1-butyl-3-methyl-pyridinium chlorodiiodide [ No CAS ]
  • 12
  • [ 125652-55-3 ]
  • [ 7646-85-7 ]
  • 1-butyl-3-methylpyridinium zinc(II) chloride [ No CAS ]
  • 13
  • [ 125652-55-3 ]
  • [ 7646-85-7 ]
  • 1-butyl-3-methylpyridinium zinc(II) chloride [ No CAS ]
  • 14
  • [ 125652-55-3 ]
  • [ 7646-85-7 ]
  • 1-butyl-3-methylpyridinium zinc(II) chloride [ No CAS ]
  • 15
  • [ 125652-55-3 ]
  • [ 7646-85-7 ]
  • 1-butyl-3-methylpyridinium zinc(II) chloride [ No CAS ]
  • 16
  • [ 125652-55-3 ]
  • 1-butyl-3-methylpyridinium chlodiiodide [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With iodine; In dichloromethane; water; at 0 - 20℃; for 24.0h; A solution of iodine (0.3 g, 1.18 mmol) in dichloromethane (35ml) was added drop wise to an ice cold solution of <strong>[125652-55-3]1-butyl-3-methylpyridinium chloride</strong> (0.2g, 1.0 mmol) in water (16ml) under stirring and then left at room temperature. After the reaction mixture was stirred for 24 hours at room temperature, the dichloromethane layer was separated and dried with sodium sulfate and then evaporated under vacuum to afford water soluble dark reddish brown ionic liquid 1-butyl-3-methylpyridinium chlorodiiodide (BMPCDI) in quantitative yields (0.4 g, 95%). 1H NMR (200 MHz, DMSO-d6 delta/ppm): 8.97 (s, 1H, Ar-H), 8.89 (d, =4.67 Hz, 1H, Ar-H), 8.32 (d, 1H, =7.6 Hz), 7.97 (t, 1H, Ar-H), 4.60 (t, 2H, CH2), 2.57 (s, 3H, Ar-CH3), 1.94 (m, 2H, -CH2-CH2-), 1.37 (m, 2H, -CH2-CH3), 0.94 (t, 3H,CH3). 13C NMR (125 MHz, CDCl3+DMSO-d6): 11.66, 16.60, 17.33, 31.38, 59.35, 125.94, 137.60, 140.21, 142.43, 144.17.
  • 17
  • [ 125652-55-3 ]
  • 1-butyl-3-methylpyridinium trichloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% With chlorine; In methanol; at 0 - 20℃; for 3.0h; To an ice cooled solution of <strong>[125652-55-3]1-butyl-3-methylpyridinium chloride</strong> (1.0 g, 5.3 mmol) in methanol (10 ml) was bubbled chlorine gas through a balloon in a closed system for 3 hours at 0 C. The ice bath was removed and the reaction mixture was left overnight at room temperature. The reaction was monitored by TLC. The excess of chlorine gas was removed under vacuum, to afford quantitative yield (1.3 g) of BMPTC as a bright yellow liquid. 1H NMR (200 MHz, DMSO-d6 delta/ppm): 9.05 (s, 1H, Ar-H), 8.94 (s, 1H, Ar-H), 8.34(d, 1H, J=6.19 Hz, Ar-H), 7.96 (s, 1H, Ar-H), 4.50 (t, 2H, CH2), 2.40 (s, 3H, Ar-CH3), 1.80 (m, 2H, - CH2-CH2-), 1.16 (m, 2H, -CH2-CH3), 0.80 (t, 3H,CH3). 13C NMR (100 MHz, CDCl3+DMSO-d6): 12.84, 18.02, 18.58, 32.93, 60.79, 127.29, 138.83, 141.66, 143.82, 145.16.
  • 18
  • [ 125652-55-3 ]
  • [ 1984-06-1 ]
  • 1-butyl-3-methylpyridinium octanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% In water; at 40℃;Flow reactor; 0.2 g (0.001 mole) of <strong>[125652-55-3]1-butyl-3-methylpyridinium chloride</strong> was dissolved in 10 g of water, and 150 mul / min of sodium octanoate (0.001 mole) was dissolved in 10 g of water to make 150 mul / min. A microreactor controlled at 80 C was connected to a silander pump I sent it away. The solution passed through the microreactor was collected and concentrated under reduced pressure to obtain 1-butyl- To obtain 0.279 g (96%) of 3-methylpyridinium octanoate. The analysis results of the obtained ionic liquid are as follows
  • 19
  • [ 125652-55-3 ]
  • [ 156-54-7 ]
  • 1-butyl-3-methylpyridinium butanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% In water; at 40℃;Flow reactor; 5.0 g (0.027 mol) of <strong>[125652-55-3]1-butyl-3-methylpyridinium chloride</strong> was dissolved in 20 g of water at a rate of 300 mul / min, and sodium butanoate 3.10 g (0.028 mol) of the compound was dissolved in 20 g of water to prepare a microreactor controlled at 40 C. at a rate of 293 mul / min. I sent it away. The solution passed through the microreactor was collected and concentrated under reduced pressure to obtain 1-butyl-3-methyltilpyridinium butanoate 5.84 g (91%) of tilpyridinium butanoate was obtained. The analysis
 

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