Home Cart Sign in  
Chemical Structure| 623-50-7 Chemical Structure| 623-50-7
Chemical Structure| 623-50-7

*Storage: Sealed in dry,Room Temperature.

*Shipping: Normal

Ethyl Glycolate

CAS No.: 623-50-7

4.5 *For research use only!

Cat. No.: A305055 Purity: 97%

Change View

Size Price

USA Stock *0-1 Day

Global Stock *5-7 Days

In Stock
1g łÇÊ¶Ê In Stock In Stock Login
5g łÇË¶Ê In Stock In Stock Login
10g łÇÿ¶Ê In Stock In Stock Login
25g łÇó¶Ê In Stock In Stock Login
100g łËÿ¶Ê In Stock In Stock Login
500g łòò¶Ê In Stock In Stock Login
1kg łÇÇî¶Ê In Stock In Stock Login

Please Login or Create an Account to: See VIP prices and availability

  • 1g

    łÇʶÊ

  • 5g

    łÇ˶Ê

  • 10g

    łÇÿ¶Ê

  • 25g

    łÇó¶Ê

  • 100g

    łËÿ¶Ê

  • 500g

    łòò¶Ê

  • 1kg

    łÇÇî¶Ê

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

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

Product Details of [ 623-50-7 ]

CAS No. :623-50-7
Formula : C4H8O3
Linear Structure Formula :HOCH2COOCH2CH3
M.W : 104.11
MDL No. :MFCD00021970
InChI Key :ZANNOFHADGWOLI-UHFFFAOYSA-N
Pubchem ID :12184

Safety of [ 623-50-7 ]

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

Calculated chemistry of [ 623-50-7 ] Show Less

Physicochemical Properties

Num. heavy atoms 7
Num. arom. heavy atoms 0
Fraction Csp3 0.75
Num. rotatable bonds 3
Num. H-bond acceptors 3.0
Num. H-bond donors 1.0
Molar Refractivity 23.79
TPSA ?

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

46.53 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.36
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

-0.17
Log Po/w (WLOGP)?

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

-0.46
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.

-0.39
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

-0.17
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.03

Water Solubility

Log S (ESOL):?

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

-0.18
Solubility 68.7 mg/ml ; 0.66 mol/l
Class?

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

Very soluble
Log S (Ali)?

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

-0.35
Solubility 46.3 mg/ml ; 0.445 mol/l
Class?

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

Very 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

-0.12
Solubility 79.2 mg/ml ; 0.76 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

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.

-7.06 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

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)

1.2

Application In Synthesis [ 623-50-7 ]

* 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 [ 623-50-7 ]
  • Downstream synthetic route of [ 623-50-7 ]

[ 623-50-7 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 110-87-2 ]
  • [ 623-50-7 ]
  • [ 61675-94-3 ]
YieldReaction ConditionsOperation in experiment
99% With toluene-4-sulfonic acid In toluene at 25℃; for 1 h; To a solution of ethyl glycolate (10 g, 0.0961 mol) in toluene (100 mL) was added 3,4- dihydro-2H-pyran ( 8 g, 0.096 1 mol) followed by catalytic amount of pTSA (30 mg) and stirred at 25 °C for 1 h. After completion of the reaction, the reaction mixture was washed with water and brine solution. The organic layer was dried over anhydrous Na2504, filtered and concentrated under reduced pressure to get 18 g (99 percent) ethyl 2-((tetrahydro-2H-pyran-2- yl)oxy)acetate, 2, as colorless liquid
94.7% at 20℃; Industrial scale Example 1.2Ethyl(tetrahydropyran-2-yloxy)-acetate (B) 100.00 kg (960.52 mol) ethyl glycolate (A) were dissolved in 180.0 L toluene and 365.22 g (1.92 mol) 4-toluenesulphonic acid monohydrate were added. At 20° C. a solution of 80.80 kg (960.52 mol) 3,4-dihydro-2H-pyran was added dropwise to the reaction mixture obtained and then the mixture was washed with 20.0 L toluene. The reaction mixture was stirred for 1 hour at 20° C. and after the reaction was complete it was combined with 100.0 L water and 6.53 kg (96.05 mol) ammonia solution (25percent). After phase separation the organic phase was washed with 100.0 L water and then the solvent was distilled off completely in vacuo.Yield: 188.4 kg (94.7percent of theory)
91.5% at 20℃; To a stirred solution of ethyl glycolate (35.3 g, 0.339 mol) containing a few crystals of p-toluene sulfonic acid, 3,4-dihydropyran (30.0 g, 0.357 mol) was added dropwise (15 g over one hour followed by 15 g over 30 min). After stirring overnight at room temperature, the mixture was diluted with diethyl ether (80 mL) and washed with a NaHCO3 solution (from 30 mL sat. NaHCO3 and 10 mL water). The organic layer was separated and dried (Na2504) followed by evaporation of the ether. The residue was distilled under high vacuum to give 58.4 g (91.5percent) of 28 as a clear liquid. 1H NMR (CDCl3, 400 MHz)δ: 1.29 (t, 3H, J=7.1 Hz, CH3), 1.53-1.95 (m, 6H, 3,4,5-THP-CH2's), 3.50-3.55 (m, 1H, 6-THP-CH2), 3.83-3.89 (m, 1H, 6-THP-CH2), 4.19 (s, 2H, OCH2CO2R), 4.20 (t, 2H, J=7.1 Hz, CH2Me), 4.75 (m, 1H, THP-CH). 13C NMR (CDCl3, 100 MHz) δ: 14.1, 18.7, 25.2, 30.0, 60.7, 61.9, 63.8, 170.4.
91.5% at 20℃; (1) Preparation of tetrahydropyran-2-yloxy-acetic acid ethyl ester (Formula 28, Scheme 4)[0378] To a stirred solution of ethyl glycolate (35.3g, 0.339mol) containing a few crystals of />toluene sulfonic acid, 3,4-dihydropyran (30.Og, 0.357mol) was added1 1 <n="113"/>dropwise (15g over one hour followed by 15g over 30min). After stirring overnight at room temperature, the mixture was diluted with diethyl ether (8OmL) and washed with a NaHCO3 solution (from 3OmL sat. NaHCO3 and 1OmL water). The organic layer was separated and dried (Na2SO4) followed by evaporation of the ether. The residue was distilled under high vacuum to give 58.4g (91.5percent) of 28 as a clear liquid. 1H NMR (CDCL3, 400MHz)δ: 1.29 (t, 3H, J = 7.1 Hz, CH3), 1.53 -1.95 (m, 6H, 3,4,5-THP-CH2's), 3.50-3.55 (m, IH, 6-THP-CH2), 3.83 - 3.89 (m, IH, 6-THP-CH2), 4.19 (s, 2H, OCH2CO2R), 4.20 (t, 2H, J = 7.1 Hz, CH2Me), 4.75 (m, IH, THP-CH). 13C NMR (CDCl3, 100MHz) δ: 14.1, 18.7, 25.2, 30.0, 60.7, 61.9, 63.8, 170.4.
81% With pyridinium p-toluenesulfonate In dichloromethane Step 1) ethyl 2-(tetrahydro-2H-pyran-2-yloxy)acetate
To a mixture of ethyl 2-hydroxyacetate (2 g, 20 mmol, Aldrich) and 3,4-dihydro-2H-pyran (3.2 g, 40 mmol, Alfa) in 40 mL of CH2Cl2 was added PPTS (500 mg, 2 mmol) slowly at rt.
The mixture was stirred at rt for 4 hours, and then the mixture was washed with brine (20 mL*2), the combined organic phases were dried over Na2SO4 and concentrated in vacuo.
The residue was purified by a silica gel column chromatography (PE: EtOAc=20:1) to give colorless oil (3.01 g, 81percent).
1H NMR (400 MHz, CDCl3): δ 1.22-1.38 (m, 4H), 1.55-1.63 (m, 3H), 1.69-1.88 (m, 3H), 3.50-3.53 (m, 1H), 3.82-3.88 (m, 1H), 4.18-4.23 (m, 4H), 4.73-4.74 (t, J=4 Hz, 1H).
81% With pyridinium p-toluenesulfonate In dichloromethane at 20℃; for 4 h; To a mixture of ethyl 2-hydroxyacetate (2 g, 20 mmol, Aldrich) and 3,4-dihydro-2H-pyran (3.2 g, 40 mmol, Alfa) in 40 mL of CH2Cl2 was added PPTS (500 mg, 2 mmol) slowly at rt.
The mixture was stirred at rt for 4 hours, and then the mixture was washed with brine (20 mLx2), the combined organic phases were dried over Na2SO4 and concentrated in vacuo.
The residure was purified by a silica gel column chromatography (PE: EtOAc =20:1) to give colorless oil (3.01 g, 81 percent).
1H NMR (400MHz, CDCl3): δ 1.22 - 1.38 (m, 4H), 1.55 - 1.63 (m, 3H), 1.69 - 1.88 (m, 3H), 3.50 - 3.53 (m, 1H), 3.82 - 3.88 (m, 1H), 4.18 - 4.23 (m, 4H), 4.73 - 4.74 (t, J=4Hz, 1H).
81% With pyridinium p-toluenesulfonate In dichloromethane at 20℃; for 4 h; Inert atmosphere To a mixture of ethyl 2 -hydroxy acetate (2 g, 20 mmol, TCI) and 3,4- dihydro-2H-pyran (3.2 g, 40 mmol, Alfa) in 40 mL Of CH2Cl2 was added PPTS (500 mg, 2 mmol, Aldrich) in portions at rt. The mixture was stirred at rt for 4 hours. The reaction mixture was then washed with brine, and the organic layer was separated and the combined organic phases were dried over Na2SO4, concentrated in vacuo. The residue was purified by a silica gel column chromatography (20: 1 (v/v) petroleum ether / EtOAc) to give the desired compound as colorless oil (3.01 g, 81 percent ).1H NMR (400MHz, CDCl3): δ 1.25 - 1.32 (m, 3H), 1.55 - 1.63 (m, 3H), 1.69 - 1.88 (m, 3H), 3.50 - 3.53 (m, IH), 3.82 - 3.88 (m, IH), 4.18 - 4.23 (m, 4H), 4.73 (t, J=3.2Hz, IH).
58% With toluene-4-sulfonic acid In toluene at 20℃; Step 1
Preparation of ethyl 2-(tetrahydro-2H-pyran-2-yloxy)acetate
A mixture of 3,4-dihydro-2H-pyran (20.4 g, 242.3 mmol), ethyl 2-hydroxyacetate (24.0 g, 230.8 mmol) and TsOH (0.794 g, 4.6 mmol) in toluene (150 mL) was stirred at room temperature overnight.
The resulting mixture was concentrated in vacuo and the residue was purified by column chromatography on silica gel (2percent EtOAc in petroleum ether) to afford ethyl 2-(tetrahydro-2H-pyran-2-yloxy)acetate (25.2 g, 58percent) as a colorless oil.

Reference: [1] Patent: WO2017/83431, 2017, A2, . Location in patent: Paragraph 00216; 00217
[2] Patent: US2011/87021, 2011, A1, . Location in patent: Page/Page column 11
[3] Patent: US2005/8570, 2005, A1, . Location in patent: Page/Page column 45
[4] Patent: WO2007/121453, 2007, A2, . Location in patent: Page/Page column 111; 112
[5] Patent: US2010/239576, 2010, A1,
[6] Patent: EP2408300, 2016, B1, . Location in patent: Paragraph 0343
[7] Patent: WO2010/45095, 2010, A1, . Location in patent: Page/Page column 76
[8] Patent: US2016/168090, 2016, A1, . Location in patent: Paragraph 0348-0349
[9] Journal of the Chemical Society, 1956, p. 2124,2126
[10] Journal of the Chemical Society, 1956, p. 4665
[11] Patent: WO2008/128961, 2008, A1, . Location in patent: Page/Page column 107
  • 2
  • [ 142-68-7 ]
  • [ 623-50-7 ]
  • [ 61675-94-3 ]
YieldReaction ConditionsOperation in experiment
32 g at 20℃; EXAMPLE 1422-((l-(2-(3-Fluoro-6-methoxy-l,5-naphthyridin-4-yl)ethyl)-2- oxabicyclo[2.2.2]octan-4-ylamino)methyl)-6H-pyrimido[5,4-b][l,4]oxazin-7(8H)-oneStep 1Ethyl 2-(Tetrahydro-2H-pyran-2-yloxy)acetateTo a stirred solution of ethyl hydroxyacetate (35.3 g) containing a few crystals of p-toluene sulfonic acid, dihydropyran (30.0 g) was added dropwise. After stirring overnight at room temperature, the mixture was diluted with dichloromethane (200 mL) and washed with a sodium hydrogencarbonate solution. The organic layer was separated and dried followed by evaporation of the dichloromethane. The residue was distilled under high vacuum to give the title compound (32 g) as a clear liquid.1H NMR (CDC13): δ 1.20-1.32 (m, 3H), 1.50-1.58 (m, 3H), 1.70-1.92 (m, 3H), 3.45-3.55 (m, 1H), 3.80-3.90 (m, 1H), 4.16-4.24 (m, 4H), 4.70-4.79 (m, 1H).
Reference: [1] Patent: WO2013/3383, 2013, A1, . Location in patent: Page/Page column 287-288
  • 3
  • [ 13754-19-3 ]
  • [ 623-50-7 ]
  • [ 934-33-8 ]
Reference: [1] Patent: US5624935, 1997, A,
  • 4
  • [ 623-50-7 ]
  • [ 74877-08-0 ]
  • [ 74877-08-0 ]
  • [ 176707-77-0 ]
Reference: [1] Tetrahedron Asymmetry, 2007, vol. 18, # 11, p. 1330 - 1337
  • 5
  • [ 623-50-7 ]
  • [ 105942-08-3 ]
  • [ 887250-14-8 ]
Reference: [1] Patent: EP1849465, 2007, A1, . Location in patent: Page/Page column 70
 

Related Products

Technical Information

Categories

Related Functional Groups of
[ 623-50-7 ]

Aliphatic Chain Hydrocarbons

Chemical Structure| 817-95-8

A909993[ 817-95-8 ]

Ethyl 2-ethoxyacetate

Similarity: 0.95

Chemical Structure| 96-35-5

A152116[ 96-35-5 ]

Methyl 2-hydroxyacetate

Similarity: 0.89

Chemical Structure| 623-61-0

A177242[ 623-61-0 ]

Isopropyl glycolate

Similarity: 0.86

Chemical Structure| 617-37-8

A260606[ 617-37-8 ]

2-Ethoxy-2-oxoacetic acid

Similarity: 0.86

Chemical Structure| 7397-62-8

A108539[ 7397-62-8 ]

Butyl 2-hydroxyacetate

Similarity: 0.82

Alcohols

Chemical Structure| 96-35-5

A152116[ 96-35-5 ]

Methyl 2-hydroxyacetate

Similarity: 0.89

Chemical Structure| 623-61-0

A177242[ 623-61-0 ]

Isopropyl glycolate

Similarity: 0.86

Chemical Structure| 7397-62-8

A108539[ 7397-62-8 ]

Butyl 2-hydroxyacetate

Similarity: 0.82

Chemical Structure| 50595-15-8

A200188[ 50595-15-8 ]

tert-Butyl 2-hydroxyacetate

Similarity: 0.78

Chemical Structure| 169751-72-8

A114623[ 169751-72-8 ]

tert-Butyl 14-hydroxy-3,6,9,12-tetraoxatetradecan-1-oate

Similarity: 0.75

Esters

Chemical Structure| 817-95-8

A909993[ 817-95-8 ]

Ethyl 2-ethoxyacetate

Similarity: 0.95

Chemical Structure| 96-35-5

A152116[ 96-35-5 ]

Methyl 2-hydroxyacetate

Similarity: 0.89

Chemical Structure| 623-61-0

A177242[ 623-61-0 ]

Isopropyl glycolate

Similarity: 0.86

Chemical Structure| 617-37-8

A260606[ 617-37-8 ]

2-Ethoxy-2-oxoacetic acid

Similarity: 0.86

Chemical Structure| 7397-62-8

A108539[ 7397-62-8 ]

Butyl 2-hydroxyacetate

Similarity: 0.82