Conditions | Yield |
---|---|
With sodium methylate at 60℃; for 8h; | 99% |
With sodium methylate; 4-methoxy-phenol at 40 - 60℃; for 6h; Temperature; Reagent/catalyst; | 99% |
With triethylamine at 20℃; for 8h; Temperature; Reagent/catalyst; Large scale; | 98% |
sodium methylate
acrylic acid methyl ester
methyl 3-methoxypropionate
Conditions | Yield |
---|---|
With 4-methoxy-phenol In methanol at 40 - 60℃; for 6h; Reagent/catalyst; | 99% |
In methanol for 24h; Heating; | 54% |
lithium methanolate
acrylic acid methyl ester
methyl 3-methoxypropionate
Conditions | Yield |
---|---|
With hydroquinone In methanol at 40℃; for 20h; | 88% |
methanol
A
Methyl 3-bromopropionate
B
methyl 3-methoxypropionate
C
ethylene dibromide
D
2-Bromoethyl methyl ether
Conditions | Yield |
---|---|
With bromine at -80℃; temperature up to 30 deg C; | A 67% B n/a C n/a D n/a |
acrylic acid methyl ester
B
methyl 3-methoxypropionate
Conditions | Yield |
---|---|
With sodium methylate In methanol | A 65% B n/a |
acrylic acid methyl ester
cyclohexanol
A
methyl 3-methoxypropionate
B
cyclohexyl acrylate
C
3-Methoxy-propionic acid cyclohexyl ester
Conditions | Yield |
---|---|
With n-butyllithium; bis(acetylacetonate)nickel(II) In benzene at 90℃; for 5h; Product distribution; | A 22% B 23% C 52% |
2-pentanol
acrylic acid methyl ester
A
methyl 3-methoxypropionate
B
3-pentyl acrylate
C
3-Methoxy-propionic acid 1-ethyl-propyl ester
Conditions | Yield |
---|---|
With n-butyllithium; bis(acetylacetonate)nickel(II) In benzene at 90℃; for 5h; Product distribution; other temp., other time; | A 19% B 25% C 48% |
acrylic acid methyl ester
isopropyl alcohol
A
methyl 3-methoxypropionate
B
isopropyl acrylate
C
isopropyl 3-methoxypropionate
D
3-isopropoxy-propionic acid isopropyl ester
Conditions | Yield |
---|---|
With n-butyllithium; bis(acetylacetonate)nickel(II) In benzene at 90℃; for 5h; Product distribution; other temp, other time; | A 17% B 15% C 42% D 26% |
acrylic acid methyl ester
iso-butanol
A
methyl 3-methoxypropionate
B
sec-butyl acrylate
C
3-methoxy-propionic acid sec-butyl ester
D
3-sec-butoxy-propionic acid sec-butyl ester
Conditions | Yield |
---|---|
With n-butyllithium; bis(acetylacetonate)nickel(II) In benzene at 90℃; for 5h; Product distribution; | A 27% B 28% C 33% D 6% |
acrylic acid methyl ester
tert-butyl alcohol
A
tert-Butyl acrylate
B
methyl 3-methoxypropionate
C
3-tert.-Butoxypropionsaeuremethylester
D
3-Methoxy-propionic acid tert-butyl ester
E
tert-butyl β-tert-butoxypropionate
Conditions | Yield |
---|---|
With n-butyllithium; bis(acetylacetonate)nickel(II) In benzene at 90℃; for 5h; Product distribution; other time, other temp.; | A 33% B 26% C 9% D 32% E 3% |
(1S,2R,5S)-(+)-menthol
acrylic acid methyl ester
A
methyl 3-methoxypropionate
B
(1S,2R,5S)‐2‐isopropyl‐5‐methylcyclohexyl acrylate
Conditions | Yield |
---|---|
With n-butyllithium; bis(acetylacetonate)nickel(II) In benzene at 90℃; for 5h; Product distribution; | A 22% B 23% |
methanol
levulinic acid methyl ester
A
methyl 3,3-dimethoxypropionate
B
acetic acid methyl ester
C
methyl 3-methoxypropionate
D
malonic acid dimethyl ester
E
Dimethyl succinate
Conditions | Yield |
---|---|
With dihydrogen peroxide; toluene-4-sulfonic acid In water at 80℃; for 6h; Reagent/catalyst; Solvent; Baeyer-Villiger Ketone Oxidation; Overall yield = 22 %; | A 13% B n/a C n/a D 8% E n/a |
Conditions | Yield |
---|---|
at -80 - 10℃; in Gegenwart von sauren Katalysatoren; | |
With boron trifluoride at -80℃; |
Conditions | Yield |
---|---|
With sulfuric acid at 65℃; |
methanol
acrylic acid methyl ester
A
3-Methoxypropionic acid
B
methyl 3-methoxypropionate
Conditions | Yield |
---|---|
With sodium |
Conditions | Yield |
---|---|
beim nachfolgendes Kochen; |
methanol
3-(N-Nitroso-methoxycarbonylamino)-propionsaeure-methylester
methyl 3-methoxypropionate
Conditions | Yield |
---|---|
With potassium carbonate |
Conditions | Yield |
---|---|
In diethyl ether |
Conditions | Yield |
---|---|
In methanol |
methyl vinyl ketone
acrylic acid methyl ester
A
1-methoxybutan-3-one
B
methyl 3-methoxypropionate
Conditions | Yield |
---|---|
With sodium hydroxide; cetyltrimethylammonim bromide In dichloromethane | A 28 % Chromat. B 10 % Chromat. |
thiophenol
acrylic acid methyl ester
A
methyl 3-methoxypropionate
B
methyl 3-phenylthiopropanoate
Conditions | Yield |
---|---|
With sodium 1.) methanol; 2.) reflux, 1 h; Yield given. Multistep reaction. Yields of byproduct given; |
methanol
acrylic acid methyl ester
A
methyl 3-methoxypropionate
B
methyl 3-phenylthiopropanoate
Conditions | Yield |
---|---|
With sodium; thiophenol 1.) methanol; 2.) reflux, 1 h; Yield given. Multistep reaction. Yields of byproduct given; |
methanol
acrylic acid
A
methyl 3-methoxypropionate
B
acrylic acid methyl ester
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid at 111.1℃; for 0.25h; Product distribution; Kinetics; other times, temp.; |
methanol
acrylic acid methyl ester
A
methyl 3,3-dimethoxypropionate
B
methyl (2E)-3-methoxy-2-propenoate
C
methyl 3-methoxypropionate
Conditions | Yield |
---|---|
With supercritical CO2; oxygen; copper dichloride; palladium dichloride at 40℃; for 12h; Product distribution; various catalysts and temperatures; | |
With supercritical CO2; oxygen; copper dichloride; palladium dichloride at 40℃; for 12h; | A 91.7 % Chromat. B 1.2 % Chromat. C 2.0 % Chromat. |
With supercritical CO2; oxygen; dichloro bis(acetonitrile) palladium(II); copper dichloride at 50℃; for 12h; | A 81.1 % Chromat. B 8.8 % Chromat. C 3.5 % Chromat. |
With supercritical CO2; oxygen; copper dichloride; palladium dichloride at 50℃; for 12h; | A 42.9 % Chromat. B 3.1 % Chromat. C 6.6 % Chromat. |
Ketene
Dimethoxymethane
sulfuric acid
methyl 3-methoxypropionate
Conditions | Yield |
---|---|
at 4℃; |
Ketene
Dimethoxymethane
boron trifluoride
methyl 3-methoxypropionate
Conditions | Yield |
---|---|
at -80℃; |
Conditions | Yield |
---|---|
at 4℃; |
methyl 3-methoxypropionate
dimethyl amine
β-methoxy-N,N-dimethylpropionic acid amide
Conditions | Yield |
---|---|
With zinc(II) trifluoroacetate at 0 - 40℃; for 8h; Reagent/catalyst; Autoclave; | 99% |
With sodium methylate; glycerol at 60℃; for 6h; Autoclave; | 86% |
With potassium tert-butylate at 20℃; under 600.06 Torr; for 4h; Product distribution / selectivity; Autoclave; | |
With sodium methylate; ethylene glycol at 60℃; for 8h; Product distribution / selectivity; Autoclave; |
methyl 3-methoxypropionate
(RS)-1-methyl-3-phenylpropylamine
(R)-3-methoxy-N-(4-phenylbutan-2-yl)propanamide
Conditions | Yield |
---|---|
With Candida antarctica lipase B; Octanethiol; [Ir(2-phenylpyridine)2(4,4′-di-tert-butyl-2,2′-bipyridine)](PF6) In acetonitrile at 38℃; for 24h; Concentration; Schlenk technique; Molecular sieve; Inert atmosphere; Irradiation; Enzymatic reaction; enantioselective reaction; | 98% |
Conditions | Yield |
---|---|
With iron(II) triflate In N,N-dimethyl-formamide at 80℃; for 2h; | 98% |
methyl 3-methoxypropionate
2-amino-1-phenylpropane
(R)-3-methoxy-N-(1-phenylpropan-2-yl)propanamide
Conditions | Yield |
---|---|
With Candida antarctica lipase B; Octanethiol; [Ir(2-phenylpyridine)2(4,4′-di-tert-butyl-2,2′-bipyridine)](PF6) In acetonitrile at 38℃; for 72h; Schlenk technique; Molecular sieve; Inert atmosphere; Irradiation; Enzymatic reaction; enantioselective reaction; | 97% |
methyl 3-methoxypropionate
Conditions | Yield |
---|---|
With Candida antarctica lipase B; Octanethiol; [Ir(2-phenylpyridine)2(4,4′-di-tert-butyl-2,2′-bipyridine)](PF6) In acetonitrile at 38℃; for 72h; Schlenk technique; Molecular sieve; Inert atmosphere; Irradiation; Enzymatic reaction; enantioselective reaction; | 96% |
methyl 3-methoxypropionate
Conditions | Yield |
---|---|
With Candida antarctica lipase B; Octanethiol; [Ir(2-phenylpyridine)2(4,4′-di-tert-butyl-2,2′-bipyridine)](PF6) In acetonitrile at 38℃; for 72h; Schlenk technique; Molecular sieve; Inert atmosphere; Irradiation; Enzymatic reaction; enantioselective reaction; | 95% |
Conditions | Yield |
---|---|
With Candida antarctica lipase B; Octanethiol; [Ir(2-phenylpyridine)2(4,4′-di-tert-butyl-2,2′-bipyridine)](PF6) In acetonitrile at 38℃; for 72h; Schlenk technique; Molecular sieve; Inert atmosphere; Irradiation; Enzymatic reaction; enantioselective reaction; | 95% |
Conditions | Yield |
---|---|
With Candida antarctica lipase B; Octanethiol; [Ir(2-phenylpyridine)2(4,4′-di-tert-butyl-2,2′-bipyridine)](PF6) In acetonitrile at 38℃; for 72h; Schlenk technique; Molecular sieve; Inert atmosphere; Irradiation; Enzymatic reaction; enantioselective reaction; | 94% |
Conditions | Yield |
---|---|
With Candida antarctica lipase B; Octanethiol; [Ir(2-phenylpyridine)2(4,4′-di-tert-butyl-2,2′-bipyridine)](PF6) In acetonitrile at 38℃; for 72h; Schlenk technique; Molecular sieve; Inert atmosphere; Irradiation; Enzymatic reaction; enantioselective reaction; | 94% |
methyl 3-methoxypropionate
Conditions | Yield |
---|---|
With lithium deuteride In diethyl ether for 1h; Heating; | 91% |
With lithium aluminium deuteride | 54% |
With lithium aluminium deuteride | 1.82 g |
methyl 3-methoxypropionate
Conditions | Yield |
---|---|
With Candida antarctica lipase B; Octanethiol; [Ir(2-phenylpyridine)2(4,4′-di-tert-butyl-2,2′-bipyridine)](PF6) In acetonitrile at 38℃; for 72h; Schlenk technique; Molecular sieve; Inert atmosphere; Irradiation; Enzymatic reaction; enantioselective reaction; | 87% |
methyl 3-methoxypropionate
1-methyl-3-p-tolyl-propylamine
Conditions | Yield |
---|---|
With Candida antarctica lipase B; Octanethiol; [Ir(2-phenylpyridine)2(4,4′-di-tert-butyl-2,2′-bipyridine)](PF6) In acetonitrile at 38℃; for 72h; Schlenk technique; Molecular sieve; Inert atmosphere; Irradiation; Enzymatic reaction; enantioselective reaction; | 85% |
methyl 3-methoxypropionate
1-cyclohexylethylamine
Conditions | Yield |
---|---|
With Candida antarctica lipase B; Octanethiol; [Ir(2-phenylpyridine)2(4,4′-di-tert-butyl-2,2′-bipyridine)](PF6) In acetonitrile at 38℃; for 72h; Schlenk technique; Molecular sieve; Inert atmosphere; Irradiation; Enzymatic reaction; enantioselective reaction; | 84% |
Conditions | Yield |
---|---|
With Candida antarctica lipase B; Octanethiol; [Ir(2-phenylpyridine)2(4,4′-di-tert-butyl-2,2′-bipyridine)](PF6) In acetonitrile at 38℃; for 60h; Schlenk technique; Molecular sieve; Inert atmosphere; Irradiation; Enzymatic reaction; enantioselective reaction; | 81% |
Conditions | Yield |
---|---|
With iron(II) triflate In N,N-dimethyl-formamide at 0 - 90℃; for 1h; Autoclave; | 79% |
Conditions | Yield |
---|---|
With iron(II) triflate at 0 - 40℃; under 760.051 Torr; for 1h; Autoclave; | 79% |
rac-2-aminooctane
methyl 3-methoxypropionate
(R)-3-methoxy-N-(octan-2-yl) propanamide
Conditions | Yield |
---|---|
With Candida antarctica lipase B; Octanethiol; [Ir(2-phenylpyridine)2(4,4′-di-tert-butyl-2,2′-bipyridine)](PF6) In acetonitrile at 38℃; for 72h; Schlenk technique; Molecular sieve; Inert atmosphere; Irradiation; Enzymatic reaction; enantioselective reaction; | 79% |
With novozyme 435 In cyclohexane at 70℃; under 7500.75 Torr; for 24h; Resolution of racemate; Inert atmosphere; Autoclave; Enzymatic reaction; |
Conditions | Yield |
---|---|
With Candida antarctica lipase B; Octanethiol; [Ir(2-phenylpyridine)2(4,4′-di-tert-butyl-2,2′-bipyridine)](PF6) In acetonitrile at 38℃; for 72h; Schlenk technique; Molecular sieve; Inert atmosphere; Irradiation; Enzymatic reaction; enantioselective reaction; | 78% |
methyl 3-methoxypropionate
diethylamine
3-methoxy-N,N-diethylpropionic acid amide
Conditions | Yield |
---|---|
With iron(II) triflate at 0 - 100℃; for 1h; Autoclave; | 76% |
Conditions | Yield |
---|---|
With iron(II) triflate at 0 - 50℃; under 760.051 Torr; for 1h; Autoclave; | 75% |
1,5-dimethylhexylamine
methyl 3-methoxypropionate
(R)-3-methoxy-N-(6-methylheptan-2-yl) propanamide
Conditions | Yield |
---|---|
With Candida antarctica lipase B; Octanethiol; [Ir(2-phenylpyridine)2(4,4′-di-tert-butyl-2,2′-bipyridine)](PF6) In acetonitrile at 38℃; for 48h; Schlenk technique; Molecular sieve; Inert atmosphere; Irradiation; Enzymatic reaction; enantioselective reaction; | 74% |
Conditions | Yield |
---|---|
With Candida antarctica lipase B; Octanethiol; [Ir(2-phenylpyridine)2(4,4′-di-tert-butyl-2,2′-bipyridine)](PF6) In acetonitrile at 38℃; for 72h; Schlenk technique; Molecular sieve; Inert atmosphere; Irradiation; Enzymatic reaction; enantioselective reaction; | 72% |
methyl 3-methoxypropionate
4-iodo-N,N-dimethyl-1H-imidazole-1-sulfonamide
4,4'-(1-hydroxy-3-methoxypropane-1,1-diyl)bis(N,N-dimethyl-1H-imidazole-1-sulfonamide)
Conditions | Yield |
---|---|
Stage #1: 4-iodo-N,N-dimethyl-1H-imidazole-1-sulfonamide With ethylmagnesium bromide In diethyl ether; dichloromethane at 20℃; for 2h; Double Grignard reaction; Inert atmosphere; Stage #2: methyl 3-methoxypropionate In diethyl ether; dichloromethane at 20℃; for 48h; Double Grignard reaction; Inert atmosphere; Stage #3: With water; ammonium chloride In diethyl ether; dichloromethane | 71% |
N-ethylhexylamine
methyl 3-methoxypropionate
Conditions | Yield |
---|---|
With iron(II) triflate at 0 - 25℃; under 760.051 Torr; for 1h; Autoclave; | 66% |
methyl 3-methoxypropionate
(+)-(R)-1-Methyl-3-(4-methoxyphenyl)-1-propylamine
Conditions | Yield |
---|---|
With Candida antarctica lipase B; Octanethiol; [Ir(2-phenylpyridine)2(4,4′-di-tert-butyl-2,2′-bipyridine)](PF6) In acetonitrile at 38℃; for 72h; Schlenk technique; Molecular sieve; Inert atmosphere; Irradiation; Enzymatic reaction; enantioselective reaction; | 64% |
Reported in EPA TSCA Inventory.
The 3-Methoxypropionic acid methyl ester with CAS registry number of 3852-09-3 is also known as Propanoic acid,3-methoxy-, methyl ester. The IUPAC name is Methyl 3-methoxypropionate. It belongs to product categories of Aromatic Propionic Acids; C2 to C5; Carbonyl Compounds; Esters. Its EINECS registry number is 223-358-1. In addition, the formula is C5H10O3 and the molecular weight is 118.13. This chemical is a clear colorless liquid that may cause inflammation to the skin or other mucous membranes. It should be sealed in ventilated and dry without light at roon temperature. What's more, this chemical can be used as pharmaceutical intermediate.
Physical properties about 3-Methoxypropionic acid methyl ester are: (1)ACD/LogP: 0.19; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.19; (4)ACD/LogD (pH 7.4): 0.19; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 30.11; (8)ACD/KOC (pH 7.4): 30.11; (9)#H bond acceptors: 3; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 4; (12)Index of Refraction: 1.391; (13)Molar Refractivity: 28.73 cm3; (14)Molar Volume: 120.9 cm3; (15)Surface Tension: 26.9 dyne/cm; (16)Density: 0.976 g/cm3; (17)Flash Point: 43.5 °C; (18)Enthalpy of Vaporization: 38.07 kJ/mol; (19)Boiling Point: 143.6 °C at 760 mmHg; (20)Vapour Pressure: 5.3 mmHg at 25 °C.
Preparation of 3-Methoxypropionic acid methyl ester: it is prepared by reaction of acrylic acid methyl ester with methanol; sodium salt. The reaction needs reagent methanol with other condition of heating for 24 hours. The yield is about 54%.
Uses of 3-Methoxypropionic acid methyl ester: it is used to produce 4-methoxy-2-methyl-butan-2-ol by reaction with methylmagnesium iodide. The reaction occurs with reagent diethyl ether at 20 °C for 18 hours. The yield is about 59%.
When you are using this chemical, please be cautious about it. As a chemical, it is irritating to eyes, respiratory system and skin. Besides, it is flammable. During using it, wear suitable protective clothing, gloves and eye/face protection. If contact with eyes accidently, rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
1. Canonical SMILES: COCCC(=O)OC
2. InChI: InChI=1S/C5H10O3/c1-7-4-3-5(6)8-2/h3-4H2,1-2H3
3. InChIKey: BDJSOPWXYLFTNW-UHFFFAOYSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LC50 | inhalation | 40gm/m3 (40000mg/m3) | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 18(3), Pg. 48, 1974. | |
rat | LCLo | inhalation | 3656ppm/6H (3656ppm) | BEHAVIORAL: MUSCLE WEAKNESS BEHAVIORAL: ATAXIA | United States Environmental Protection Agency, Office of Pesticides and Toxic Substances. Vol. 8EHQ-0486-0599, |
rat | LDLo | oral | 1700mg/kg (1700mg/kg) | BEHAVIORAL: MUSCLE WEAKNESS BEHAVIORAL: ATAXIA | United States Environmental Protection Agency, Office of Pesticides and Toxic Substances. Vol. 8EHQ-0486-0599, |
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