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Chemical Structure| 111-83-1 Chemical Structure| 111-83-1

Structure of 1-Bromooctane
CAS No.: 111-83-1

Chemical Structure| 111-83-1

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Product Citations

Product Citations

Lim, Taeho ; Ryoo, Jeong Yup ; Han, Min Su ;

Abstract: In this study, we developed a simple transition-metal-free borylation reaction of aryl bromides. Bis-boronic acid (BBA), was used, and the borylation reaction was performed using a simple procedure at a mild temperature. Under mild conditions, aryl bromides were converted to arylboronic acids directly without any deprotection steps and purified by conversion to trifluoroborate salts. The functional group tolerance was considerably high. The mechanism study suggested that this borylation reaction proceeds via a radical pathway.

Alternative Products

Product Details of [ 111-83-1 ]

CAS No. :111-83-1
Formula : C8H17Br
M.W : 193.12
SMILES Code : CCCCCCCCBr
MDL No. :MFCD00000276
InChI Key :VMKOFRJSULQZRM-UHFFFAOYSA-N
Pubchem ID :8140

Safety of [ 111-83-1 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H227-H315-H318-H335-H411
Precautionary Statements:P210-P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P310-P362+P364-P403+P233-P501
Class:9
UN#:3082
Packing Group:

Computational Chemistry of [ 111-83-1 ] Show Less

Physicochemical Properties

Num. heavy atoms 9
Num. arom. heavy atoms 0
Fraction Csp3 1.0
Num. rotatable bonds 6
Num. H-bond acceptors 0.0
Num. H-bond donors 0.0
Molar Refractivity 48.44
TPSA ?

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

0.0 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

3.06
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

4.89
Log Po/w (WLOGP)?

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

3.74
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.

3.76
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

3.3
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

3.75

Water Solubility

Log S (ESOL):?

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

-3.72
Solubility 0.0366 mg/ml ; 0.00019 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.

-4.63
Solubility 0.00457 mg/ml ; 0.0000237 mol/l
Class?

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

Moderately 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

-3.96
Solubility 0.0214 mg/ml ; 0.000111 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

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.

-4.01 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<2.0
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)

3.36

Application In Synthesis of [ 111-83-1 ]

* 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 [ 111-83-1 ]
  • Downstream synthetic route of [ 111-83-1 ]

[ 111-83-1 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 111-83-1 ]
  • [ 111-42-2 ]
  • [ 15520-05-5 ]
YieldReaction ConditionsOperation in experiment
91% With potassium carbonate In acetonitrile for 12 h; Inert atmosphere; Reflux 1 -bromooctane (3.0 g, 1.5 mmol), diethanolamine (2.4 g, 2.3 mmol), anhydrous potassium carbonate (4.28 g, 3.1 mmol) were taken in acetonitrile (40 mL) and the contents were refluxed for 12 h nitrogen atmosphere. After cooling reaction mixture was evaporated and extracted with dichloromethane and dried over anhy. Na2S04 removed under reduced pressure to get the crude productwhich was further purified by column chromatography using dichloromethane and methanol as eluentto obtain pure 2,2'-(octylazanediyl)bis(ethan-l-ol) as colorless oil (590 mg, 91 percent).1H NMR (CDC13): δ 4.22 (brs, 2H, OHCH2), 3.86 (t, 4H, JAB = 5 Hz, -CH2OH), 3.10 (t, 4H, JAB = 4.5 Hz, -CH2N), 2.94 (t, 2H, JAB = 8 Hz, -CH2N), 1.69-1.60 (m, 2H, -CH2), 1.30-1.25 (m, 10H, - CH2), 0.87 (t, 3H, JAB = 7 Hz, -CH3).
76.7% With potassium carbonate; potassium iodide In acetonitrile for 12 h; Inert atmosphere; Reflux (1) n-octyl bromide (6.0 g, 30 mmol), diethanolamine (4.73 g, 45 mmol),Anhydrous potassium carbonate (8.29 g, 60 mmol) and potassium iodide (1.0 g) were added to a 250 mL two-necked flask, 80 mL of acetonitrile was added and the nitrogen was bubbled through for 5 minutes to replace the air in the system and then refluxed for 12 h.(2) The reaction was stopped, acetonitrile was removed by steaming, 60 mL of dichloromethane and 60 mL of water were added, and the mixture was separated. The organic phase was washed twice with water to remove excess diethanolamine. The product has a certain solubility in water, washed, the water phase and then extracted twice with methylene chloride. The organic phase was separated and dried over anhydrous sodium sulfate.(3) steamed to remove methylene chloride to obtain a light yellow liquid 5.00g, yield 76.7percent JLC detection, ethyl acetate / petroleum ether = 1: 1 as the development agent, the target product than the value of Rf = 0.33 The(4) A 250 mL single-necked flask was charged with (3) the procedure to prepare 5.00 g (23 mmol) of octyldiethanolamine, bromopropyne3.56 g (30 mmo 1) and ethanol 1 OOmL, stirred and refluxed for 12 h under stirring.(5) The excess of bromopropyne and solvent ethanol were distilled off under reduced pressure to give 7.36 g of the crude product as brownish red viscous liquid,100percent. TLC detection, dichloromethane: methanol = 6: 1, the specific value of Rf = 0.50
References: [1] Patent: WO2018/42367, 2018, A2, . Location in patent: Page/Page column 95; 96-97.
[2] Molecular Crystals and Liquid Crystals (1969-1991), 1990, vol. 185, p. 131 - 140.
[3] Patent: CN106187790, 2016, A, . Location in patent: Paragraph 0044-0050.
[4] Patent: US2541088, 1946, , .
[5] European Journal of Medicinal Chemistry, 1976, vol. 11, p. 115 - 124.
 

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