[ CAS No. 10076-48-9 ] {[proInfo.proName]}

Name: 10076-48-9|Methyl 2,2-dimethoxypropanoate|98%
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SKU: A167678
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Quality Control of [ 10076-48-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 10076-48-9 ]

SDS Specification

Alternatived Products of [ 10076-48-9 ]

Product Details of [ 10076-48-9 ]

CAS No. :	10076-48-9	MDL No. :	MFCD00048066
Formula :	C₆H₁₂O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KHQQDBIXHUJARJ-UHFFFAOYSA-N
M.W :	148.16	Pubchem ID :	82339
Synonyms :

Calculated chemistry of [ 10076-48-9 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.83
Num. rotatable bonds :	4
Num. H-bond acceptors :	4.0
Num. H-bond donors :	0.0
Molar Refractivity :	34.45
TPSA :	44.76 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.08 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.17
Log Po/w (XLOGP3) :	0.17
Log Po/w (WLOGP) :	0.17
Log Po/w (MLOGP) :	-0.05
Log Po/w (SILICOS-IT) :	0.05
Consensus Log Po/w :	0.5

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-0.6
Solubility :	37.1 mg/ml ; 0.25 mol/l
Class :	Very soluble
Log S (Ali) :	-0.67
Solubility :	31.9 mg/ml ; 0.215 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.63
Solubility :	34.9 mg/ml ; 0.236 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.83

Safety of [ 10076-48-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 10076-48-9 ]

* 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.

Upstream synthesis route of [ 10076-48-9 ]
Downstream synthetic route of [ 10076-48-9 ]

[ 10076-48-9 ] Synthesis Path-Upstream 1~16

1
[ 600-22-6 ]
[ 149-73-5 ]
[ 10076-48-9 ]

Yield	Reaction Conditions	Operation in experiment
77%	With sulfuric acid In methanol for 4 h; Reflux	Methyl 2,2-dimethoxypropanoate 100 g (979 mmol) of methyl 2-oxopropanoate were admixed with 135 g (1273 mmol) of trimethyl orthoformate in 240 ml of methanol. After addition of 0.96 g (9.79 mmol) of concentrated H₂SO₄, the mixture was heated to reflux for 4 h. The solvent was distilled off within 2 h, and the crude product was cooled to 10° C. and added to a solution of 2.4 g of KOH in 1200 ml of water at 10° C. After repeated extraction with diethyl ether, the product was dried over Na₂SO₄, filtered and concentrated. The residue was distilled again. B.p. (10 mbar): 50-55° C. Yield: 118 g (77percent) ¹H NMR (CDCl₃): σ=1.53 (s, 3H,C-CH₃), 3.29 (s, 6H, CH₃-O-C-O-CH₃), 3.82 (s, 3H,COOCH₃).

Reference： [1] Journal of the American Chemical Society, 1983, vol. 105, # 7, p. 2021 - 2029
[2] Patent: US2015/245616, 2015, A1, . Location in patent: Paragraph 0189; 0190

2
[ 600-22-6 ]
[ 149-73-5 ]
[ 107-31-3 ]
[ 10076-48-9 ]

Reference： [1] Patent: WO2006/35915, 2006, A1, . Location in patent: Page/Page column 49-50

3
[ 67-56-1 ]
[ 600-22-6 ]
[ 149-73-5 ]
[ 10076-48-9 ]

Yield	Reaction Conditions	Operation in experiment
62%	for 4 h; Reflux	Svnthesis of S-Methoxy-pyrrolidine-S-carboxylic acid methyl ester Step 1 : Preparation of methyl α, α-dimethoxypropionate The procedure by Ernest Wenkert, et al. (JACS, 1983, 705, 2021 -2029) was followed. A solution of methyl pyruvate (44g), trimethyl orthoformate (62 ml), concentrated H₂SO₄ (0.2 ml) in MeOH (120 ml) was reluxed for 4 hours. In the next one hour period, solvent (about 80 ml) was distilled out. The reaction mixture was cooled to 10 ⁰C, poured into a KOH solution (1 .2 g KOH in 600 ml water), and extracted with ether (3x). Combined ether extracts were washed with brine and dried (MgSO₄). After concentration, the residue was distilled under vacuum to provide the acetal (8BH) (4Og, 62percent, 40-43C/1 torr).

Reference： [1] Patent: WO2009/105500, 2009, A1, . Location in patent: Page/Page column 215
[2] Journal of the Chemical Society, 1942, p. 521

4
[ 600-22-6 ]
[ 10076-48-9 ]

Reference： [1] Patent: EP1798218, 2007, A1,

5
[ 67-56-1 ]
[ 127-17-3 ]
[ 10076-48-9 ]

Reference： [1] Synthesis, 1983, # 3, p. 201 - 203
[2] Green Chemistry, 2014, vol. 16, # 7, p. 3569 - 3579

6
[ 127-17-3 ]
[ 149-73-5 ]
[ 10076-48-9 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1982, # 8, p. 1897 - 1904
[2] Journal of Heterocyclic Chemistry, 1990, vol. 27, # 3, p. 815 - 817
[3] Tetrahedron Letters, 2003, vol. 44, # 15, p. 3081 - 3084

7
[ 67-56-1 ]
[ 600-22-6 ]
[ 10076-48-9 ]

Reference： [1] Synthesis, 1983, # 3, p. 201 - 203

8
[ 7001-18-5 ]
[ 10076-48-9 ]

Reference： [1] Journal of the Chemical Society, 1947, p. 1033

9
[ 67-56-1 ]
[ 127-17-3 ]
[ 77-76-9 ]
[ 10076-48-9 ]

Reference： [1] Journal of Organic Chemistry, 1967, vol. 32, p. 1615 - 1617

10
[ 1069-12-1 ]
[ 553-90-2 ]
[ 10076-48-9 ]

Reference： [1] Tetrahedron Letters, 1985, vol. 26, # 16, p. 1931 - 1934

11
[ 1069-12-1 ]
[ 10076-48-9 ]

Reference： [1] Chemische Berichte, 1966, vol. 99, p. 1892 - 1898

12
[ 67-56-1 ]
[ 127-17-3 ]
[ 600-22-6 ]
[ 10076-48-9 ]

Reference： [1] Tetrahedron Letters, 1998, vol. 39, # 47, p. 8563 - 8566

13
[ 89-91-8 ]
[ 74-88-4 ]
[ 10076-48-9 ]

Reference： [1] Synthesis, 1979, p. 33 - 34

14
[ 67-56-1 ]
[ 683-70-5 ]
[ 553-90-2 ]
[ 96-35-5 ]
[ 79-20-9 ]
[ 10076-48-9 ]
[ 96-34-4 ]

Reference： [1] Chemische Berichte, 1987, vol. 120, p. 1573 - 1580

15
[ 67-56-1 ]
[ 1809-02-5 ]
[ 600-22-6 ]
[ 109-87-5 ]
[ 79-20-9 ]
[ 10076-48-9 ]
[ 80-62-6 ]
[ 108365-85-1 ]

Reference： [1] Chemische Berichte, 1987, vol. 120, p. 1573 - 1580

16
[ 7647-01-0 ]
[ 7001-18-5 ]
[ 10076-48-9 ]

Reference： [1] Journal of the Chemical Society, 1947, p. 1053

[ 10076-48-9 ] Synthesis Path-Downstream 1~63

1
[ 7001-18-5 ]
[ 10076-48-9 ]

Reference： [1]Journal of the Chemical Society,1947,p. 1033

2
[ 10076-48-9 ]
2,2-dimethoxy-propionic acid amide [ No CAS ]

Reference： [1]Journal of the Chemical Society,1942,p. 521

3
[ 67-56-1 ]
[ 600-22-6 ]
[ 149-73-5 ]
[ 10076-48-9 ]

Yield	Reaction Conditions	Operation in experiment
62%	With sulfuric acid; for 4h;Reflux;	Svnthesis of S-Methoxy-pyrrolidine-S-carboxylic acid methyl ester Step 1 : Preparation of methyl alpha, alpha-dimethoxypropionate The procedure by Ernest Wenkert, et al. (JACS, 1983, 705, 2021 -2029) was followed. A solution of methyl pyruvate (44g), trimethyl orthoformate (62 ml), concentrated H2SO4 (0.2 ml) in MeOH (120 ml) was reluxed for 4 hours. In the next one hour period, solvent (about 80 ml) was distilled out. The reaction mixture was cooled to 10 0C, poured into a KOH solution (1 .2 g KOH in 600 ml water), and extracted with ether (3x). Combined ether extracts were washed with brine and dried (MgSO4). After concentration, the residue was distilled under vacuum to provide the acetal (8BH) (4Og, 62%, 40-43C/1 torr).

Reference： [1]Patent: WO2009/105500,2009,A1 .Location in patent: Page/Page column 215
[2]Journal of the Chemical Society,1942,p. 521

4
[ 1069-12-1 ]
[ 10076-48-9 ]

Reference： [1]Chemische Berichte,1966,vol. 99,p. 1892 - 1898

5
[ 67-56-1 ]
[ 127-17-3 ]
[ 77-76-9 ]
[ 10076-48-9 ]

Reference： [1]Journal of Organic Chemistry,1967,vol. 32,p. 1615 - 1617

6
[ 89-91-8 ]
[ 74-88-4 ]
[ 10076-48-9 ]

Reference： [1]Synthesis,1979,p. 33 - 34

7
[ 505-23-7 ]
[ 10076-48-9 ]
[ 88791-31-5 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1983,p. 2979 - 2983

8
[ 67-56-1 ]
[ 600-22-6 ]
[ 10076-48-9 ]

Reference： [1]Synthesis,1983,p. 201 - 203

9
[ 67-56-1 ]
[ 1809-02-5 ]
[ 600-22-6 ]
[ 109-87-5 ]
[ 79-20-9 ]
[ 10076-48-9 ]
[ 80-62-6 ]
[ 108365-85-1 ]

Reference： [1]Chemische Berichte,1987,vol. 120,p. 1573 - 1580

10
[ 67-56-1 ]
[ 683-70-5 ]
[ 553-90-2 ]
[ 96-35-5 ]
[ 79-20-9 ]
[ 10076-48-9 ]
[ 96-34-4 ]

Reference： [1]Chemische Berichte,1987,vol. 120,p. 1573 - 1580

11
[ 1193-55-1 ]
[ 10076-48-9 ]
[ 87027-63-2 ]

Reference： [1]Tetrahedron Letters,1983,vol. 24,p. 2331 - 2334

12
[ 1069-12-1 ]
[ 553-90-2 ]
[ 10076-48-9 ]

Reference： [1]Tetrahedron Letters,1985,vol. 26,p. 1931 - 1934

13
[ 75-52-5 ]
[ 10076-48-9 ]
[ 144401-97-8 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1992,p. 1975 - 1980

14
[ 10076-48-9 ]
[ 100841-11-0 ]
ethyl 2-<1-<<1-methoxy-1-(methoxycarbonyl)ethyl>peroxy>ethyl>propenoate [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1994,vol. 59,p. 4765 - 4772

15
[ 10076-48-9 ]
[ 99573-19-0 ]
[ 154406-06-1 ]

Reference： [1]Journal of the Chemical Society. Chemical communications,1993,p. 1463 - 1464

16
[ 10076-48-9 ]
[ 6285-28-5 ]
[ 141763-09-9 ]
[ 141763-08-8 ]

Reference： [1]Synthesis,1992,p. 398 - 402
[2]Synthesis,1992,p. 398 - 402

17
[ 10076-48-9 ]
[ 7001-18-5 ]

Yield	Reaction Conditions	Operation in experiment
81%	With phosphorus pentoxide; In N,N-dimethyl-formamide; at 100℃; for 1h;	Methyl 2-methoxyacrylate 100 g (675 mmol) of <strong>[10076-48-9]methyl 2,2-dimethoxypropanoate</strong> were initially charged in 300 ml of DMF, 52.7 g (371 mmol) of P2O5 were added in portions while stirring and then the mixture was heated to 100 C. for 1 h. The reaction solution was then added to 1 l of a saturated NaHCO3 solution cooled to 10 C. This solution was extracted with diethyl ether, and the organic extracts were washed three times with saturated NaCl solution, dried over Na2SO4, filtered and concentrated. The product was used without further purification. Yield: 66.0 g (81%) 1H NMR (CDCl3): sigma=3.67 (s, 3H,C-CH3), 3.83 (s, 3H, COOCH3), 4.63 (d, 1H, J=3 Hz,C=CHH), 5.37 (d, 1H, J=3 Hz, C=CHH).
	With potassium hydroxide;	Then while still at 127 C., powdered potassium hydroxide (0.35 g, 0.006 mol) was added in one portion. There was an immediate exotherm to 135 C. In less than 40 minutes, conversion of <strong>[10076-48-9]methyl 2,2-dimethoxypropionate</strong> to methyl 2-methoxyacrylate was greater than 99%.
	With toluene-4-sulfonic acid; at 140 - 190℃;	Step 2: Preparation of 2-methoxyacrylate The procedure by Ernest Wenkert, et al. (JACS, 1983, 705, 2021 -2029) was followed. To a one neck flask was charged alpha, alpha-dimethoxypropionate (8BH) (150 g) and Tolunesulfonic acid monohydrate (3g) and a short path distillation head was attached. The mixture was heated at 140 0C (oil bath temperature) and methanol began to come out first. The product (76 g) of (9BH) was then distilled out later after oil bath temperature was raised over 190 0C.

Reference： [1]Patent: US2015/245616,2015,A1 .Location in patent: Paragraph 0191; 0192
[2]Journal of Medicinal Chemistry,2020
[3]Journal of the American Chemical Society,1983,vol. 105,p. 2021 - 2029
[4]Journal of the Chemical Society. Perkin transactions I,1982,p. 1897 - 1904
[5]Tetrahedron Letters,2003,vol. 44,p. 3081 - 3084
[6]Patent: US4304928,1981,A
[7]Patent: WO2009/105500,2009,A1 .Location in patent: Page/Page column 215

18
[ 10076-48-9 ]
[ 141-78-6 ]
[ 128883-38-5 ]

Reference： [1]Journal of Heterocyclic Chemistry,1990,vol. 27,p. 815 - 817

19
[ 67-56-1 ]
[ 127-17-3 ]
[ 10076-48-9 ]

Reference： [1]Synthesis,1983,p. 201 - 203
[2]Green Chemistry,2014,vol. 16,p. 3569 - 3579

20
[ 127-17-3 ]
[ 149-73-5 ]
[ 10076-48-9 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1982,p. 1897 - 1904
[2]Journal of Heterocyclic Chemistry,1990,vol. 27,p. 815 - 817
[3]Tetrahedron Letters,2003,vol. 44,p. 3081 - 3084

21
[ 10076-48-9 ]
[ 107-18-6 ]
[ 84012-01-1 ]

Reference： [1]Journal of Organic Chemistry,1983,vol. 48,p. 158 - 162

22
[ 10076-48-9 ]
[ 598-41-4 ]
[ 107378-23-4 ]

Reference： [1]Journal of Heterocyclic Chemistry,1986,vol. 23,p. 871 - 875

23
[ 600-22-6 ]
[ 149-73-5 ]
[ 10076-48-9 ]

Yield	Reaction Conditions	Operation in experiment
77%	With sulfuric acid; In methanol; for 4h;Reflux;	Methyl 2,2-dimethoxypropanoate 100 g (979 mmol) of methyl 2-oxopropanoate were admixed with 135 g (1273 mmol) of trimethyl orthoformate in 240 ml of methanol. After addition of 0.96 g (9.79 mmol) of concentrated H2SO4, the mixture was heated to reflux for 4 h. The solvent was distilled off within 2 h, and the crude product was cooled to 10 C. and added to a solution of 2.4 g of KOH in 1200 ml of water at 10 C. After repeated extraction with diethyl ether, the product was dried over Na2SO4, filtered and concentrated. The residue was distilled again. B.p. (10 mbar): 50-55 C. Yield: 118 g (77%) 1H NMR (CDCl3): sigma=1.53 (s, 3H,C-CH3), 3.29 (s, 6H, CH3-O-C-O-CH3), 3.82 (s, 3H,COOCH3).

Reference： [1]Journal of the American Chemical Society,1983,vol. 105,p. 2021 - 2029
[2]Patent: US2015/245616,2015,A1 .Location in patent: Paragraph 0189; 0190

24
[ 10076-48-9 ]
[ 4726-84-5 ]
[ 107378-25-6 ]

Reference： [1]Journal of Heterocyclic Chemistry,1986,vol. 23,p. 871 - 875

25
[ 10076-48-9 ]
nitromethane dianion [ No CAS ]
[ 144401-97-8 ]

Reference： [1]Journal of the Chemical Society. Chemical communications,1987,vol. No. 8,p. 567 - 568

26
[ 758-16-7 ]
[ 10076-48-9 ]
3,3-Dimethoxy-N,N-dimethyl-2-oxo-thiobutyramide [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1995,vol. 117,p. 5859 - 5860

27
[ 758-16-7 ]
[ 10076-48-9 ]
3-(1,1-Dimethoxy-ethyl)-3-hydroxy-1-methyl-azetidine-2-thione [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1995,vol. 117,p. 5859 - 5860

28
[ 67-56-1 ]
[ 127-17-3 ]
[ 600-22-6 ]
[ 10076-48-9 ]

Reference： [1]Tetrahedron Letters,1998,vol. 39,p. 8563 - 8566

29
[ 10076-48-9 ]
[ 99547-44-1 ]