Home Cart Sign in  
Chemical Structure| 603-79-2 Chemical Structure| 603-79-2
Chemical Structure| 603-79-2

2,3-Dimethylbenzoic acid

CAS No.: 603-79-2

4.5 *For Research Use Only !

Cat. No.: A101265 Purity: 97%

Change View

Size Price

US Stock

Global Stock

In Stock
1g łÇʶÊÊ Inquiry Inquiry
5g łÇ˶ÊÊ Inquiry Inquiry
10g łÇÿ¶ÊÊ Inquiry Inquiry
25g łËǶÊÊ Inquiry Inquiry
100g łÿî¶ÊÊ Inquiry Inquiry
500g łËîͶÊÊ Inquiry Inquiry

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1g

    łÇʶÊÊ

  • 5g

    łÇ˶ÊÊ

  • 10g

    łÇÿ¶ÊÊ

  • 25g

    łËǶÊÊ

  • 100g

    łÿî¶ÊÊ

  • 500g

    łËîͶÊÊ

In Stock

- +

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support Online Technical Q&A
Product Citations

Alternative Products

Product Details of [ 603-79-2 ]

CAS No. :603-79-2
Formula : C9H10O2
M.W : 150.17
SMILES Code : C1=CC=C(C(=C1C(O)=O)C)C
MDL No. :MFCD00002479
InChI Key :RIZUCYSQUWMQLX-UHFFFAOYSA-N
Pubchem ID :11782

Safety of [ 603-79-2 ]

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

Calculated chemistry of [ 603-79-2 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 6
Fraction Csp3 0.22
Num. rotatable bonds 1
Num. H-bond acceptors 2.0
Num. H-bond donors 1.0
Molar Refractivity 43.33
TPSA ?

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

37.3 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.57
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

2.82
Log Po/w (WLOGP)?

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

2.0
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.

2.25
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

2.14
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.16

Water Solubility

Log S (ESOL):?

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

-2.89
Solubility 0.196 mg/ml ; 0.0013 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.

-3.26
Solubility 0.0824 mg/ml ; 0.000549 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

-2.53
Solubility 0.446 mg/ml ; 0.00297 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

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.

-5.21 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.

0.56

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)

1.0

Application In Synthesis of [ 603-79-2 ]

* 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 [ 603-79-2 ]

[ 603-79-2 ] Synthesis Path-Downstream   1~14

  • 3
  • [ 64-19-7 ]
  • [ 603-79-2 ]
  • [ 2142-71-4 ]
  • 6
  • [ 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%).
  • 8
  • [ 603-79-2 ]
  • alkaline permanganate [ No CAS ]
  • [ 569-51-7 ]
  • 9
  • [ 526-73-8 ]
  • [ 5779-93-1 ]
  • [ 603-79-2 ]
  • 10
  • [ 186581-53-3 ]
  • [ 603-79-2 ]
  • [ 15012-36-9 ]
  • 12
  • [ 603-79-2 ]
  • [ 81093-21-2 ]
  • 13
  • [ 603-79-2 ]
  • [ 15012-36-9 ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride; In N,N-dimethyl-formamide; (1) To 160 ml of methanol cooled to -10 C. was dropwise added 46.4 ml of thionyl chloride while stirring. To the solution was added a mixture of 24 g of 2,3-dimethyl benzoic acid and 1 ml of DMF, and the mixture was stirred at room temperature for 4 days. After concentration, the residue was dissolved in ether. The solution was washed with water, 5% sodium carbonate, and water in this order. The solvent was evaporated and the residue was purified by vacuum distillation to obtain 25.1 g of methyl 2,3-dimethylbenzoate.
  • 14
  • [ 74-88-4 ]
  • [ 603-79-2 ]
  • [ 15012-36-9 ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate; In N,N-dimethyl-formamide; at 20℃; for 2h; 3-Aminomethyl-2-methyl-benzoic acid methyl ester: 2,3-Dimethylbenzoic acid (1.0 g, 6.66 mmol) was dissolved in DMF (15 mL) and then Cs2CO3 (1.5 equiv.) and MeI (1.2 equiv.) were added. The mixture was stirred for 2 h at room temperature then diluted with EtOAc and H2O. The organic layer was washed with H2O and a saturated LiCl solution, and then dried over MgSO4 and concentrated under reduced pressure to give sticky oil. The oil was dissolved in CCl4 (20 mL) and NBS (1.1 equiv.) and AIBN (0.1 equiv.) were added. The mixture was heated at reflux for 4 h then cooled to room temperature to give a white precipitate which was filtered off. The yellow solution was concentrated, the oil was dissolved in DMF (15 mL) and then NaN3 (1.2 equiv.) was added. The mixture was stirred for 2 h at room temperature then diluted with ethyl acetate and H2O. The organic layer was washed with H2O and a saturated lithium chloride solution, dried over MgSO4, and concentrated under reduced pressure to give sticky oil. The crude oil was dissolved in of CHCl3 (20 mL) and MeOH (20 mL), and then 10% Pd/C (0.20 g) and conc. HCl (1.5 mL) were added. The mixture was shaken under H2 gas (50 psi) for 16 h. The Pd/C was filtered through a pad of Celite and the pad was washed with a solution of 20% MeOH in CH2Cl2. The pale yellow solution was concentrated under reduced pressure, and the residual was dissolved in MeOH (10 mL) and diluted with Et2O (100 mL) to give a white precipitate. The precipitate was collected by filteration and dried to give the title compound (0.79 g, 55%).
With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; I-144: N2-(3,4-dimethyl-5-methoxycarbonyl)phenyl-5-methyl-N4-(2-oxo-2,3-dihydro-1,3-benzoxazol-5-yl)-2,4-pyrimidinediamine 2,3-Dimethylbenzoic acid (1 g) and K2CO3 (1.1 g, 1.2 eq.) were suspended in DMF (10 mL). To the reaction mixture, was added iodomethane (0.5 mL, 1.2 eq.). The reaction was stirred at rt overnight, then diluted with water (80 mL). The solution was extracted with ethyl acetate (80 mL) and evaporated to give the methyl ester. 1H NMR (300 MHz, DMSO) delta 7.49 (d, J=7.8 Hz, 1H), 7.33 (d, J=7.5 Hz, 1H), 7.15 (t, J=7.8 Hz, 1H), 3.79 (s, 3H), 2.33 (s, 3H), 2.26 (s, 3H).
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 603-79-2 ]

Aryls

Chemical Structure| 619-04-5

A235591 [619-04-5]

3,4-Dimethylbenzoic acid

Similarity: 1.00

Chemical Structure| 619-21-6

A104474 [619-21-6]

3-Formylbenzoic acid

Similarity: 0.97

Chemical Structure| 99-04-7

A964007 [99-04-7]

3-Methylbenzoic acid(Flakes or Chunks or Granular)

Similarity: 0.97

Chemical Structure| 619-66-9

A112685 [619-66-9]

4-Formylbenzoic acid

Similarity: 0.97

Chemical Structure| 99-94-5

A120071 [99-94-5]

4-Methylbenzoic acid

Similarity: 0.97

Carboxylic Acids

Chemical Structure| 619-04-5

A235591 [619-04-5]

3,4-Dimethylbenzoic acid

Similarity: 1.00

Chemical Structure| 619-21-6

A104474 [619-21-6]

3-Formylbenzoic acid

Similarity: 0.97

Chemical Structure| 99-04-7

A964007 [99-04-7]

3-Methylbenzoic acid(Flakes or Chunks or Granular)

Similarity: 0.97

Chemical Structure| 619-66-9

A112685 [619-66-9]

4-Formylbenzoic acid

Similarity: 0.97

Chemical Structure| 99-94-5

A120071 [99-94-5]

4-Methylbenzoic acid

Similarity: 0.97