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Chemical Structure| 15012-36-9 Chemical Structure| 15012-36-9
Chemical Structure| 15012-36-9

Methyl 2,3-dimethylbenzoate

CAS No.: 15012-36-9

4.5 *For Research Use Only !

Cat. No.: A518470 Purity: 97%

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Product Details of [ 15012-36-9 ]

CAS No. :15012-36-9
Formula : C10H12O2
M.W : 164.20
SMILES Code : O=C(OC)C1=CC=CC(C)=C1C
MDL No. :MFCD06203773
InChI Key :RQTXEJYGOHZSIW-UHFFFAOYSA-N
Pubchem ID :27000

Safety of [ 15012-36-9 ]

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

Calculated chemistry of [ 15012-36-9 ] Show Less

Physicochemical Properties

Num. heavy atoms 12
Num. arom. heavy atoms 6
Fraction Csp3 0.3
Num. rotatable bonds 2
Num. H-bond acceptors 2.0
Num. H-bond donors 0.0
Molar Refractivity 47.65
TPSA ?

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

26.3 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.34
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

3.11
Log Po/w (WLOGP)?

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

2.09
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.

2.55
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

2.64
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.55

Water Solubility

Log S (ESOL):?

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

-3.06
Solubility 0.145 mg/ml ; 0.00088 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.

-3.33
Solubility 0.0767 mg/ml ; 0.000467 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

-3.24
Solubility 0.0947 mg/ml ; 0.000577 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.

-5.09 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

0.0 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)

1.46

Application In Synthesis of [ 15012-36-9 ]

* 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 [ 15012-36-9 ]

[ 15012-36-9 ] Synthesis Path-Downstream   1~29

  • 3
  • C10H13O2(1+) [ No CAS ]
  • [ 15012-36-9 ]
  • 4
  • [ 15012-36-9 ]
  • [ 13651-14-4 ]
  • 5
  • [ 15012-36-9 ]
  • [ 127168-91-6 ]
YieldReaction ConditionsOperation in experiment
100% With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; at 80℃; for 16h; Step a. To a solution of <strong>[15012-36-9]methyl 2,3-dimethylbenzoate</strong> (CAS Number 15012-36-9, available from Accela Chembio) (5 g, 30.48 mmol) in CC14 (40 ml) were added NBS (10.8 g, 61 mmol) and AIBN (0.2 g, 0.91 mmol) at rt. The reaction mixture was heated at 80C for 16 h. The reaction mixture was filtered and evaporate to yield methyl 2,3-bis(bromomethyl)benzoate (10.1 g, quantitative). This material was used directly for the next step without further purification.
96% With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; for 2h;Heating / reflux; Compound 5 (53.3 g; 0.32 mol) was dissolved in carbon tetrachloride (850 mL), under nitrogen. To the solution was added N-bromosuccinimide (115.5 g; 0.65 mol) and 2,2'-azobis(2-methyl-propionitrile (1.6 g; 0.010 mol). The reaction mixture was stirred at reflux for approximately 2 hours and the colour of this mixture changed from yellow to colorless. It was allowed to cool to room temperature and filtered off. The filtrate was evaporated in vacuo to give compound 6 (98.7 g; 96%) as a yellow liquid.1H-NMR (300 MHz, CDCI3): delta 3.95 (s, 3H), 4.68 (s, 2H), 5.14 (s, 2H), 7.36 (t, 1H), 7.55 (dd, 1 H), 7.90 (dd, 1 H). GC-MS m/z = 322.
94% With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; for 4h;Reflux; [0506] Preparation of compound 3 (Scheme 13): To a solution of 2 (2.1 g, 13.3 mmol, 1.0 eq) in Cd4 (30 mL) was added NBS (4.7 g, 26.6 mmol, 2.0 eq) and BPO (0.2 g). The mixture was heated to reflux for 4h. The reaction was diluted with DCM (30 mL), washed by water (2 x 30 mL), dried over Na2SO4, concentrated to give a crude product, which was purified by column chromatography to give compound 3; methyl 2,3-bis(bromomethyl)benzoate (4.0 g, 94%).
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane;Heating / reflux; To a stirred solution of <strong>[15012-36-9]methyl 2,3-dimethylbenzoate</strong> (1.75 g, 10.7 mmol) in carbon tetrachloride (35 mL) under argon was added freshly recrystallized N-bromosuccinimide (3.90 g, 21.9 mmol) and AIBN (50 mg). The reaction mixture was heated to reflux under argon for 4 h and then cooled and filtered. Evaporation gave a yellow oil, 3.53 g, predominantly methyl 2,3-bis(bromomethyl)benzoate.

  • 6
  • [ 576-23-8 ]
  • [ 616-38-6 ]
  • [ 15012-36-9 ]
  • 7
  • [ 576-23-8 ]
  • [ 616-38-6 ]
  • [ 15012-36-9 ]
  • [ 1217-63-6 ]
  • 8
  • [ 15012-36-9 ]
  • [ 202719-50-4 ]
  • 9
  • [ 67-56-1 ]
  • [ 603-79-2 ]
  • [ 15012-36-9 ]
YieldReaction ConditionsOperation in experiment
98% With thionyl chloride;Heating / reflux; Step 1. To a solution of 2,3-dimethylbenzoic acid (50.2 g; 0.33 mol) in MeOH (1L) was added dropwise thionyl chloride (62 mL; 0.83 mol, exothermic). The reaction mixture was stirred at reflux overnight and allowed to cool to room temperature. Evaporation of the solvent in vacuo yielded compound 5 (53.3 g; 98%) as a yellow liquid.1H-NMR (300 MHz, CDCI3): delta 2.34 (s, 3H), 3.45 (s, 3H), 3.90 (s, 3H), 7.15 (t, 1H), 7.28 (d, 1H), 7.62 (d, 1H).
98% With thionyl chloride; for 3h;Reflux; [0505] Preparation of compound 2 (Scheme 13): To a solution of 1; 2,3- dimethylbenzoic acid (2.0 g, 13.3 mmol, 1.0 eq) in MeOH (30 mL) was added thionyl chloride (1.5 mL) and stirred at reflux for 3h. The mixture was concentrated, extracted with EA (30 mL). The organic layers were washed with water (2 x 30 mL),dried over Na2504, concentrated to give the desired product 2 without further purification (2.1 g, 98%).
  • 10
  • [ 62708-44-5 ]
  • [ 124-41-4 ]
  • [ 15012-36-9 ]
  • [ 40851-62-5 ]
  • 13
  • methyl 1-methyl-6-methylidenecyclohexa-2,4-diene-1-carboxylate [ No CAS ]
  • [ 15018-12-9 ]
  • [ 15012-36-9 ]
  • [ 14920-81-1 ]
  • 14
  • [ 186581-53-3 ]
  • [ 603-79-2 ]
  • [ 15012-36-9 ]
  • 15
  • [ 15012-36-9 ]
  • [ 107-30-2 ]
  • [ 745074-47-9 ]
YieldReaction ConditionsOperation in experiment
1.1 g With iron(III) chloride; thionyl chloride; In 1,2-dichloro-ethane; at 0 - 55℃; for 2h; To a stirred solution of <strong>[15012-36-9]methyl 2,3-dimethylbenzoate</strong> (2.0 g, 12.2 mmol) in 1,2-dichloroethane (10 mL) were added chloromethyl methyl ether (5 mL, 36.0 mmol), thionylchloride (0.36 mL, 5.0 mmol) and ferric chloride (0.4 g, 2.4 mmol) at 0 C. The resulting mixture was heated to 55 C for 2 h. After cooling to room temperature, the mixture was extracted with EtOAc (3 x 100 mL) and washed with water (20 mL) and brine (20 mL). The combined organic extracts were dried over anhydrous Mg504, filtered and concentrated.Silica gel chromatography (hexane:EtOAc) afforded the title compound (1.1 g). MS (ES) m/z 213 (M+H).
  • 16
  • [ 15012-36-9 ]
  • potassium; 2,3-dimethyl-benzoate [ No CAS ]
  • 17
  • [ 15012-36-9 ]
  • 2,3-dimethyl-benzoic acid allyl ester [ No CAS ]
  • 18
  • [ 15012-36-9 ]
  • 2,3-dimethyl-benzoic acid benzyl ester [ No CAS ]
  • 23
  • [ 15012-36-9 ]
  • BMS-488516 [ No CAS ]
  • 24
  • [ 15012-36-9 ]
  • <i>N</i>-{5-[3-(4-acetyl-piperazine-1-carbonyl)-4,5-dimethyl-benzylsulfanyl]-thiazol-2-yl}-4-[(1-hydroxymethyl-2-methyl-propylamino)-methyl]-benzamide [ No CAS ]
  • 25
  • [ 70588-24-8 ]
  • [ 15012-36-9 ]
  • 26
  • [ 15012-36-9 ]
  • (7S,8S)-8-Bromo-7-methoxy-bicyclo[4.2.0]octa-1(6),2,4-triene-2-carboxylic acid methyl ester [ No CAS ]
  • 27
  • [ 15012-36-9 ]
  • (5S,8R)-8-Bromo-6,6,7,7-tetracyano-5-methoxy-5,6,7,8-tetrahydro-naphthalene-1-carboxylic acid methyl ester [ No CAS ]
  • 28
  • [ 15012-36-9 ]
  • (7R,8S)-7,8-Dibromo-bicyclo[4.2.0]octa-1(6),2,4-triene-2-carboxylic acid methyl ester [ No CAS ]
  • 29
  • [ 15012-36-9 ]
  • [ 90484-24-5 ]
 

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