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Chemical Structure| 106-91-2 Chemical Structure| 106-91-2

Structure of Glycidyl methacrylate
CAS No.: 106-91-2

Chemical Structure| 106-91-2

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CAS No.: 106-91-2

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Product Details of [ 106-91-2 ]

CAS No. :106-91-2
Formula : C7H10O3
M.W : 142.15
SMILES Code : CC(C(OCC1OC1)=O)=C
MDL No. :MFCD00005137
InChI Key :VOZRXNHHFUQHIL-UHFFFAOYSA-N
Pubchem ID :7837

Safety of [ 106-91-2 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H227-H302-H311-H314-H317-H335-H341-H350-H360-H372-H401
Precautionary Statements:P201-P202-P210-P260-P264-P270-P271-P272-P273-P280-P301+P312+P330-P301+P330+P331-P303+P361+P353-P304+P340+P310-P305+P351+P338+P310-P308+P313-P333+P313-P361+P364-P370+P378-P403+P233-P403+P235-P405-P501
Class:8(6.1)
UN#:2922
Packing Group:Ⅱ

Computational Chemistry of [ 106-91-2 ] Show Less

Physicochemical Properties

Num. heavy atoms 10
Num. arom. heavy atoms 0
Fraction Csp3 0.57
Num. rotatable bonds 4
Num. H-bond acceptors 3.0
Num. H-bond donors 0.0
Molar Refractivity 35.55
TPSA ?

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

38.83 ?2

Lipophilicity

Log Po/w (iLOGP)?

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

2.11
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

0.77
Log Po/w (WLOGP)?

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

0.5
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.

0.25
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

1.43
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.01

Water Solubility

Log S (ESOL):?

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

-0.94
Solubility 16.2 mg/ml ; 0.114 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.

-1.17
Solubility 9.71 mg/ml ; 0.0683 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

-0.84
Solubility 20.4 mg/ml ; 0.144 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.

-6.62 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

2.0 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)

 2.6

Application In Synthesis of [ 106-91-2 ]

* 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 [ 106-91-2 ]

[ 106-91-2 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 106-91-2 ]
  • [ 79-10-7 ]
  • [ 1709-71-3 ]
YieldReaction ConditionsOperation in experiment
2,6-di-tert-butyl-4-methyl-phenol; triethylamine; at 80℃; for 48h;Product distribution / selectivity; 13.27 g of glycidyl methacrylate, 0.02 g of 2,6-ditert.-butyl-4-methylphenol, 6.78 g of acrylic acid and 0.10 g of one of the catalysts set forth in Table 1 were reacted each time at 80 C. in a glass vessel with a small opening and with magnetic stirring. The acid value was determined after 24 and 48 hours. If it was greater than 4 mg KOH/g after 48 hours, the batch was discarded without further analysis. The catalysts in comparison examples C2 to C6 exhibit, for a given weight, much lower activity, and those in C7 and C8 a lower activity, than the catalyst in example 9 according to the invention. The reaction product was at least equal to the comparison products according to the acid value, hydroxyl value and purity (GPC analysis).
2,6-di-tert-butyl-4-methyl-phenol; triphenylphosphine; at 80℃; for 48h;Product distribution / selectivity; 13.27 g of glycidyl methacrylate, 0.02 g of 2,6-ditert.-butyl-4-methylphenol, 6.78 g of acrylic acid and 0.10 g of one of the catalysts set forth in Table 1 were reacted each time at 80 C. in a glass vessel with a small opening and with magnetic stirring. The acid value was determined after 24 and 48 hours. If it was greater than 4 mg KOH/g after 48 hours, the batch was discarded without further analysis. The catalysts in comparison examples C2 to C6 exhibit, for a given weight, much lower activity, and those in C7 and C8 a lower activity, than the catalyst in example 9 according to the invention. The reaction product was at least equal to the comparison products according to the acid value, hydroxyl value and purity (GPC analysis).
1,4-diaza-bicyclo[2.2.2]octane; 2,6-di-tert-butyl-4-methyl-phenol; at 80℃; for 48h;Product distribution / selectivity; 13.27 g of glycidyl methacrylate, 0.02 g of 2,6-ditert.-butyl-4-methylphenol, 6.78 g of acrylic acid and 0.10 g of one of the catalysts set forth in Table 1 were reacted each time at 80 C. in a glass vessel with a small opening and with magnetic stirring. The acid value was determined after 24 and 48 hours. If it was greater than 4 mg KOH/g after 48 hours, the batch was discarded without further analysis. The catalysts in comparison examples C2 to C6 exhibit, for a given weight, much lower activity, and those in C7 and C8 a lower activity, than the catalyst in example 9 according to the invention. The reaction product was at least equal to the comparison products according to the acid value, hydroxyl value and purity (GPC analysis).
2,6-di-tert-butyl-4-methyl-phenol; N-benzyl-N,N,N-triethylammonium chloride; at 80℃; for 48h;Product distribution / selectivity; 13.27 g of glycidyl methacrylate, 0.02 g of 2,6-ditert.-butyl-4-methylphenol, 6.78 g of acrylic acid and 0.10 g of one of the catalysts set forth in Table 1 were reacted each time at 80 C. in a glass vessel with a small opening and with magnetic stirring. The acid value was determined after 24 and 48 hours. If it was greater than 4 mg KOH/g after 48 hours, the batch was discarded without further analysis. The catalysts in comparison examples C2 to C6 exhibit, for a given weight, much lower activity, and those in C7 and C8 a lower activity, than the catalyst in example 9 according to the invention. The reaction product was at least equal to the comparison products according to the acid value, hydroxyl value and purity (GPC analysis).
2,6-di-tert-butyl-4-methyl-phenol; dibutyltin dilaurate; at 80℃; for 48h;Product distribution / selectivity; 13.27 g of glycidyl methacrylate, 0.02 g of 2,6-ditert.-butyl-4-methylphenol, 6.78 g of acrylic acid and 0.10 g of one of the catalysts set forth in Table 1 were reacted each time at 80 C. in a glass vessel with a small opening and with magnetic stirring. The acid value was determined after 24 and 48 hours. If it was greater than 4 mg KOH/g after 48 hours, the batch was discarded without further analysis. The catalysts in comparison examples C2 to C6 exhibit, for a given weight, much lower activity, and those in C7 and C8 a lower activity, than the catalyst in example 9 according to the invention. The reaction product was at least equal to the comparison products according to the acid value, hydroxyl value and purity (GPC analysis).
2,2'-thiobis-ethanol; 2,6-di-tert-butyl-4-methyl-phenol; at 80℃; for 48h;Product distribution / selectivity; 13.27 g of glycidyl methacrylate, 0.02 g of 2,6-ditert.-butyl-4-methylphenol, 6.78 g of acrylic acid and 0.10 g of one of the catalysts set forth in Table 1 were reacted each time at 80 C. in a glass vessel with a small opening and with magnetic stirring. The acid value was determined after 24 and 48 hours. If it was greater than 4 mg KOH/g after 48 hours, the batch was discarded without further analysis. The catalysts in comparison examples C2 to C6 exhibit, for a given weight, much lower activity, and those in C7 and C8 a lower activity, than the catalyst in example 9 according to the invention. The reaction product was at least equal to the comparison products according to the acid value, hydroxyl value and purity (GPC analysis).
stannous octoate; 2,6-di-tert-butyl-4-methyl-phenol; at 80℃; for 24h;Product distribution / selectivity; 13.27 g of glycidyl methacrylate, 0.02 g of 2,6-ditert.-butyl-4-methylphenol, 6.78 g of acrylic acid and 0.10 g of one of the catalysts set forth in Table 1 were reacted each time at 80 C. in a glass vessel with a small opening and with magnetic stirring. The acid value was determined after 24 and 48 hours. If it was greater than 4 mg KOH/g after 48 hours, the batch was discarded without further analysis. The catalysts in comparison examples C2 to C6 exhibit, for a given weight, much lower activity, and those in C7 and C8 a lower activity, than the catalyst in example 9 according to the invention. The reaction product was at least equal to the comparison products according to the acid value, hydroxyl value and purity (GPC analysis).
tris(dimethylamino)borane; 2,6-di-tert-butyl-4-methyl-phenol; at 80℃; for 48h;Product distribution / selectivity; 13.27 g of glycidyl methacrylate, 0.02 g of 2,6-ditert.-butyl-4-methylphenol, 6.78 g of acrylic acid and 0.10 g of one of the catalysts set forth in Table 1 were reacted each time at 80 C. in a glass vessel with a small opening and with magnetic stirring. The acid value was determined after 24 and 48 hours. If it was greater than 4 mg KOH/g after 48 hours, the batch was discarded without further analysis. The catalysts in comparison examples C2 to C6 exhibit, for a given weight, much lower activity, and those in C7 and C8 a lower activity, than the catalyst in example 9 according to the invention. The reaction product was at least equal to the comparison products according to the acid value, hydroxyl value and purity (GPC analysis).
With 10H-phenothiazine; triphenylphosphine; at 80 - 110℃; Example 2Synthesis of 3-acryloyloxy-2-hydroxypropyl methacrylate (GAMA); The apparatus from Example 1 is used. All of the chemicals used are available commercially, from Sigma Aldrich, for example.Reservoir 1 is charged with a GMA solution whose composition is as follows:Glycidyl methacrylate (GMA): 98.2% by weightTriphenylphosphine (TPP): 1.5% by weightPhenothiazine: 0.004% by weightDi-tert-butylmethylphenol (inhibitor KB) 0.22% by weightReservoir 2 is charged with acrylic acid.The reaction apparatus is heated to 80 C. empty. Reactant is metered in from reservoir 1 with a mass flow rate of 3.07 kg/h; from reservoir 2, reactant is metered in with a mass flow rate of 1.56 kg/h.The reactors are each thermally conditioned with a mass flow rate of 500 kg of thermostat oil (silicone oil) per hour (WK1, WK2).After the start of the metered feeds, the plant is slowly flooded. When the reactors of the first heating circuit (WK1) have been filled, the temperature in this circuit is slowly raised, in a number of steps, to a jacket temperature of 110 C. The same procedure at the same rate is carried out with the reactors of the second thermal conditioning circuit (WK2) when they are filled, the jacket temperature set here being 110 C. After a further 3 residence times, the product (GAMA) is obtained.Result: residual monomer content: 0.5% by weight acrylic acid, 0.48% by weight GMA
With tetramethlyammonium chloride; at 90℃; for 4h; (1) Weigh 64 g of glycidyl methacrylate, Adding tetramethylammonium chloride 3.0g, Hydroxyanisole 0.1g, In a three-necked flask, Stirring to 90 C, Using a constant pressure dropping funnel, 37.8 g of acrylic acid was added dropwise to the reaction system. After the addition is completed, The acid value was tested after 4 hours of reaction. When the acid value is less than 10 mg KOH / g, the reaction is stopped.
With tetramethlyammonium chloride; at 90℃; for 4h; A method for preparing a methacrylate monomer for a dental restorative material, comprising the following steps: (1) Weigh 64 g of glycidyl methacrylate, and add 3.0 g of tetramethylammonium chloride and 0.1 g of hydroxyanisole in a three-necked flask.The temperature was raised to 90 C, and 37.8 g of acrylic acid was added dropwise to the reaction system by a constant pressure dropping funnel. After the completion of the dropwise addition, the acid value was measured after the reaction was continued for 4 hours, and when the acid value was less than 10 mg KOH/g, the reaction was stopped

  • 2
  • [ 106-91-2 ]
  • [ 79-10-7 ]
  • [ 433937-38-3 ]
  • [ 1709-71-3 ]
  • 3
  • [ 36196-44-8 ]
  • [ 2530-85-0 ]
  • [ 106-91-2 ]
  • C42H67N3O20S3Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
at 90℃; for 8h;Inert atmosphere; General procedure: A separable four-necked flask was equipped with a thermometer and a reflux tube, and the inner part was made a nitrogen atmosphere. Into this four-necked flask, components A, B and C were charged in accordance with the following Table 1, and reacted at 90 C for 8 hours under the conditions shown in Table 1. The viscosity after the reaction is shown in Table 1
 

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