Home Cart Sign in  
Chemical Structure| 112-89-0 Chemical Structure| 112-89-0

Structure of 112-89-0

Chemical Structure| 112-89-0

*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 [ 112-89-0 ]

CAS No. :112-89-0
Formula : C18H37Br
M.W : 333.39
SMILES Code : CCCCCCCCCCCCCCCCCCBr
MDL No. :MFCD00000231
InChI Key :WSULSMOGMLRGKU-UHFFFAOYSA-N
Pubchem ID :8218

Safety of [ 112-89-0 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H304
Precautionary Statements:P301+P310-P331-P405-P501

Computational Chemistry of [ 112-89-0 ] Show Less

Physicochemical Properties

Num. heavy atoms 19
Num. arom. heavy atoms 0
Fraction Csp3 1.0
Num. rotatable bonds 16
Num. H-bond acceptors 0.0
Num. H-bond donors 0.0
Molar Refractivity 96.51
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.

5.38
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

10.31
Log Po/w (WLOGP)?

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

7.64
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.

6.35
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

7.69
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

7.47

Water Solubility

Log S (ESOL):?

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

-7.35
Solubility 0.000015 mg/ml ; 0.000000045 mol/l
Class?

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

Poorly soluble
Log S (Ali)?

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

-10.25
Solubility 0.0000000188 mg/ml ; 0.0000000001 mol/l
Class?

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

Insoluble
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

-7.97
Solubility 0.00000356 mg/ml ; 0.0000000107 mol/l
Class?

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

Poorly 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

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.

-1.01 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

1.0
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

1.0
Egan?

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

1.0
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

3.0
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)

4.43

Application In Synthesis of [ 112-89-0 ]

* 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 [ 112-89-0 ]

[ 112-89-0 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 6933-49-9 ]
  • [ 112-89-0 ]
  • [ 132901-69-0 ]
  • 2
  • [ 1190-39-2 ]
  • [ 112-89-0 ]
  • [ 124502-19-8 ]
  • 3
  • ethyl acetate n-hexane [ No CAS ]
  • [ 2150-46-1 ]
  • [ 112-89-0 ]
  • [ 53434-16-5 ]
YieldReaction ConditionsOperation in experiment
72% With potassium carbonate; In N,N-dimethyl-formamide; acetone; EXAMPLE 47 2-Hydroxy-5-(octadecyloxy)benzoic acid methyl ester A mixture of 1 g (5.95 mmol) of 2,5-dihydroxybenzoic acid methyl ester, 1.98 g (5.95 mmol) of 1-bromooctadecane and 0.825 g (5.95 mmol) of potassium carbonate in 20 ml of acetone and 1 ml of DMF was stirred at reflux for 20 hours. The usual workup followed by purification by HPLC using 1% ethyl acetate-hexane gave 1.8 (72% yield, mp 61-64) of 2-hydroxy-5-(octadecyloxy)benzoic acid methyl ester.
  • 4
  • [ 2150-46-1 ]
  • [ 112-89-0 ]
  • [ 53434-16-5 ]
YieldReaction ConditionsOperation in experiment
70% With potassium carbonate; In water; acetone; EXAMPLE 58 2-Hydroxy-5-(octadecyloxy)benzoic acid methyl ester A mixture of 2.0 g (11.9 mmol) of 2,5-dihydroxybenzoic acid methyl ester, 4.55 g (13.1 mmol) of 1-bromooctadecane and 1.9 g (13.7 mmol) of potassium carbonate in 50 ml of acetone was stirred at reflux for 24 hours. The solvent was removed at reduced pressure and the residue was treated with water. The product was extracted with ethyl acetate and the dried extract was concentrated to a solid which was recrystallized from ethyl acetate-hexane to give 3.5 g (70% yield, mp 53-54) of 2-hydroxy-5-(octadecyloxy)benzoic acid methyl ester. Anal. Calcd for C26 H44 O4: C, 74.24; H, 10.54. Found: C, 74.45; H, 10.89.
With sodium methylate; In methanol; EXAMPLE 14 2-Hydroxy-4-n-octadecoxy benzoic hydrazide hydrochloride Methyl-2,5-dihydroxy benzoate 16.8 g. (0.1 m.) was added to sodium methoxide (5.9 g. 0.11 m.) in methanol (100 ml.). 1-Octadecyl bromide (33.4 g., 0.1 m.) was added slowly, and the reaction mixture refluxed for 18 hours. The mixture was poured into water and shaken with ether. The ethereal extracts were washed with water, dried with magnesium sulphate, and the solvent was removed to give crude methyl 2-hydroxy-5-octadecoxy benzoate (41 g.). Distillation under reduced pressure gave the pure ester (10 g.) which had a boiling point of 232-242C at 0.07 mm. Hg. pressure, and a melting point of 62-63.5C after crystallisation from ethanol.
  • 5
  • [ 31191-08-9 ]
  • [ 112-89-0 ]
  • [ 135453-26-8 ]
  • 6
  • [ 605-32-3 ]
  • [ 112-89-0 ]
  • [ 1430074-45-5 ]
  • 7
  • [ 623-57-4 ]
  • [ 112-89-0 ]
  • [ 871258-14-9 ]
YieldReaction ConditionsOperation in experiment
65% Synthesis of DSDMA and DODMA: (0248) DSDMA and DODMA were synthesized using the respective alkyl bromides with methodology derived from that of a DOTMA precursor (Feigner et al, PNAS USA, 84, 7413-7417 (1987)). 3-(Dimethylamino)-1,2-propanediol (714 mg, 6 mmol) and 95percent sodium hydride (NaH, 1.26 g, 50 mmol) were stirred in benzene (30 mL) under argon for 30 minutes. The correct (either oleyl or stearyl) alkyl bromide (5.0 g, 15 mmol) was added and the reaction refluxed under argon for 18 hours. The reaction mixture was then cooled in an ice bath while quenching via the slow addition of ethanol. Following dilution with a further 150 mL of benzene, the mixture was washed with distilled water (2×150 mL) and brine (150 mL), using ethanol (20 mL) to aid phase separation if necessary. The organic phase was dried over magnesium sulphate and evaporated. The crude product was purified on a silica gel (Kiesel Gel 60) column eluted with chloroform containing 0-5percent methanol. Column fractions were analyzed by thin layer chromatography (TLC) (silica gel, chloroform/methanol 9:1 v/v, visualized with molybdate) and fractions containing pure product (Rf=0.5) were pooled and concentrated. The product was decolorized by stirring for 30 minutes in a suspension of activated charcoal (1 g) in ethanol (75 mL) at 60° C. The charcoal was removed by filtration through Celite, and the ethanol solution concentrated to typically yield 2.4 g (65percent) of pure product. 1H-NMR (DSDMA): deltaH 3.65-3.32 (m, 7H, OCH, 3×OCH2), 2.45-2.31 (m, 2H, NCH2), 2.27 (s, 6H, 2×NCH3), 1.61-1.45 (m, 4H, OCH2CH2), 1.40-1.17 (m, 60H, Hstearyl), 0.86 (t, 6H, CH2CH3). 1H-NMR (DODMA): deltaH 5.4-5.27 (m, 4H, 2×CH?CH), 3.65-3.35 (m, 7H, OCH, 3×OCH2), 2.47-2.33 (m, 2H, NCH2), 2.28 (s, 6H, 2×NCH3), 2.06-1.94 (m, 8H, 4×CH2CH?CH), 1.61-1.50 (m, 4H, OCH2CH2), 1.38-1.20 (m, 48H, Holeyl), 0.88 (t, 6H, CH2CH3).
  • 8
  • [ 33893-89-9 ]
  • [ 112-89-0 ]
  • C24H41N5 [ No CAS ]
  • C24H41N5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In acetonitrile; at 97℃; for 7.5h; 2-Pyridyl carbonitrile (12.5 g, 0.12 mol) was charged to a 2 L, three neck round bottomed flask equipped with condenser with attached N2 inlet-outlet, mechanical stirrer and thermocouple. Solid NH4Cl (6.4 g, 0.12 mol) was added. DMF (880 mL) then water (6.27 g) was added followed by sodium azide (7.8 g, 0.12 mol). The reaction was refluxed at approximately 137 C. overnight. A new very polar spot was seen by TLC but some starting material remained. NaN3 and NH4Cl, (each 0.05 mol/mol, based on the amount of substance of the 2-pyridyl carbonitrile) was added followed by a small amount of water. The reaction was complete after a total of about 65 h at 137 C. The mixture was carefully concentrated to remove DMF (CAUTION; a small amount of azide remains). The residue was dissolved in aqueous Na2CO3 (8 g, 0.075 mol in 0.3 L of aqueous solution). This aqueous layer was washed with ethyl acetate (2×200 mL). The aqueous layer was carefully brought to a pH of from 4 to 5 under good ventilation as traces of hydrazoic acid may form. The solid product (7 g) precipitated out of solution. The pH was then brought to between 1 and 2, and another batch of crystals was collected (3.8 g). These batches were shown to be the same substance by NMR. The resulting 2-pyridyl tetrazole (10.24 g, 0.07 mol) was allowed to react with bromooctadecane (25.2 g, 0.077 mol) and triethylamine (7.8 g, 0.077 mol) in acetonitrile (80 mL) at 97 C. for about 7.5 h. The solvent was removed under reduced pressure. The isomers were isolated by automated flash chromatography (120 g column; eluted with a gradient of from 0% to 25% ethyl acetate/hexanes over thirty minutes. The flow was 85 mL per minute.) The less polar spot had a mass of 8.3 g. The more polar spot had a mass of 13.6 g. The total yield of the reaction was 81%. HMBC NMR analysis led to the following structural assignments: (0184) Pyr-Ttz-1-C18: Less polar spot: 1H NMR (400 MHz, CDCl3) delta 8.7 (dd, 1H, ArH), 8.3 (d, 1H, ArH), 7.9 (t, 1H, ArH), 7.4 (m, 1H, ArH), 5.0 (t, 2H, NCH2), 1.9 (m, 2H, NCH2CH2), 1.4-1.2 (m, 28H, aliph), 0.85 (t, 3H, Me). Melting point: 67.6-68.9 C. Pyr-Ttz-2-C18: More polar spot: 1H NMR NMR (400 MHz, CDCl3) delta 8.8 (dd, 1H, ArH), 8.3 (d, 1H, ArH), 7.8 (t, 1H, ArH), 7.4 (m, 1H, ArH), 4.7 (t, 2H, NCH2), 2.1 (m, 2H, NCH2CH2), 1.4-1.2 (m, 28H, aliph), 0.9 (t, 3H, Me). Melting temperature was between 66.4 C. and 67.9 C.
 

Historical Records