2-Methylpentanedioic acid dimethyl ester supplier

Name
2-Methylpentanedioic acid dimethyl ester
EINECS 251-552-6
CAS No. 14035-94-0
Article Data21
CAS DataBase
Density 1.037 g/cm³
Solubility
Melting Point
Formula C₈H₁₄O₄
Boiling Point 204.4 °C at 760 mmHg
Molecular Weight 174.197
Flash Point 90.8 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Dimethyl 2-methylpentanedioate;Pentanedioic acid, 2-methyl-, dimethyl ester;Dimethyl 2-Methylglutarate;Rhodiasolv IRIS;
PSA 52.60000
LogP 0.74870

Synthetic route

: 67-56-1
methanol

: 18069-17-5
2-methylglutaric acid

: C6H11NO3

: 14035-94-0
dimethyl 2-methylglutarate

Conditions

Conditions	Yield
With sulfuric acid In water at 60℃; for 3h; Temperature; Inert atmosphere;	86.1%

...Expand

: 6203-89-0
2,6-dimethyl-1-cyclohexen-1-yl acetate

A: 14035-94-0
dimethyl 2-methylglutarate

B: 79664-96-3
methyl 2-methyl-5-oxopentanoate

C: 2570-90-3
6-oxo-2-methyl-heptanoic acid methyl ester

Conditions

Conditions	Yield
With lithium perchlorate In methanol; acetic acid at 2 - 3℃; electrolysis; Yield given;	A n/a B n/a C 72%

...Expand

: 67-56-1
methanol

: 201230-82-2
carbon monoxide

: 106-99-0
buta-1,3-diene

A: 627-93-0
hexanedioic acid dimethyl ester

B: 14035-94-0
dimethyl 2-methylglutarate

C: 69665-13-0
dimethyl 2-propylmaleate

Conditions

Conditions	Yield
2-6-dimethoxybenzoic acid; palladium diacetate In methoxybenzene at 170℃; under 30003 Torr; for 10h; Product distribution / selectivity;	A 59% B 19% C 13%

...Expand

: 67-56-1
methanol

: 26682-69-9
4-Diethylcarbamoyl-pentanoic acid methyl ester

: 14035-94-0
dimethyl 2-methylglutarate

Conditions

Conditions	Yield
With toluene-4-sulfonic acid

: 554-12-1
propanoic acid methyl ester

: 292638-85-8
acrylic acid methyl ester

: 14035-94-0
dimethyl 2-methylglutarate

Conditions

Conditions	Yield
With sodium methylate

: 108-05-4
vinyl acetate

: 554-12-1
propanoic acid methyl ester

A: 14035-94-0
dimethyl 2-methylglutarate

B: 100316-11-8
hexane-1,3,5-tricarboxylic acid trimethyl ester

C: 3,5-Bis-methoxycarbonyl-2,3-dimethyl-octanedioic acid dimethyl ester

D: 4,6-Bis-methoxycarbonyl-4-methyl-nonanedioic acid dimethyl ester

Conditions

Conditions	Yield
With di-tert-butyl peroxide at 135 - 140℃; for 3h; Yield given. Further byproducts given. Yields of byproduct given;

...Expand

: 108-05-4
vinyl acetate

: 554-12-1
propanoic acid methyl ester

A: 14035-94-0
dimethyl 2-methylglutarate

B: 100316-11-8
hexane-1,3,5-tricarboxylic acid trimethyl ester

C: 3,5-Bis-methoxycarbonyl-2,3-dimethyl-octanedioic acid dimethyl ester

D: 4,6-Bis-methoxycarbonyl-2-methyl-nonanedioic acid dimethyl ester

Conditions

Conditions	Yield
With di-tert-butyl peroxide at 135 - 140℃; for 3h; Yield given. Further byproducts given. Yields of byproduct given;

...Expand

: 108-05-4
vinyl acetate

: 554-12-1
propanoic acid methyl ester

A: 14035-94-0
dimethyl 2-methylglutarate

B: 100316-11-8
hexane-1,3,5-tricarboxylic acid trimethyl ester

C: 4,6-Bis-methoxycarbonyl-4-methyl-nonanedioic acid dimethyl ester

D: 4,6-Bis-methoxycarbonyl-2-methyl-nonanedioic acid dimethyl ester

Conditions

Conditions	Yield
With di-tert-butyl peroxide at 135 - 140℃; for 3h; Yield given. Further byproducts given. Yields of byproduct given;

...Expand

: 6203-89-0
2,6-dimethyl-1-cyclohexen-1-yl acetate

A: 14035-94-0
dimethyl 2-methylglutarate

B: 79664-96-3
methyl 2-methyl-5-oxopentanoate

C: 2570-90-3
6-oxo-2-methyl-heptanoic acid methyl ester

D: 40790-56-5
2,6-dimethyl-2-cyclohexen-1-one

E: 79664-90-7
2,6-dimethyl-2-methoxycyclohexanone

Conditions

Conditions	Yield
With lithium perchlorate In methanol; acetic acid Product distribution; Mechanism; var. electrolysis conditions, other cycloalkanone enol acetates, var. 2-oxocycloalkan-1-ols;

...Expand

: 201230-82-2
carbon monoxide

: 292638-85-8
acrylic acid methyl ester

A: 53358-17-1
1,3-bis(methoxycarbonyl)-1-butene

B: 554-12-1
propanoic acid methyl ester

C: 13865-19-5
4-oxobutanoic acid methyl ester

D: 14035-94-0
dimethyl 2-methylglutarate

E: 22634-92-0
4-oxo-heptanedioic acid dimethyl ester

Conditions

Conditions	Yield
With water; Co(CO)8-diphos at 135℃; under 76000 Torr; for 10h; Product distribution; Mechanism; var. solvents; var. time, pressure and temperature; also acrylonitrile;	A 1.3 mmol B 0.15 mmol C 0.20 mmol D 0.20 mmol E 32.7 mmol

...Expand

: 201230-82-2
carbon monoxide

: 292638-85-8
acrylic acid methyl ester

A: 53358-17-1
1,3-bis(methoxycarbonyl)-1-butene

B: 13865-19-5
4-oxobutanoic acid methyl ester

C: 14035-94-0
dimethyl 2-methylglutarate

D: 22634-92-0
4-oxo-heptanedioic acid dimethyl ester

Conditions

Conditions	Yield
With water; dicobalt octacarbonyl; 1,2-bis-(diphenylphosphino)ethane In 1,4-dioxane at 135℃; under 76000 Torr; for 10h; Further byproducts given;	A 1.3 mmol B 0.20 mmol C 0.20 mmol D 32.7 mmol

...Expand

: 72658-09-4
(E)-(1-methoxyprop-1-enyloxy)trimethylsilane

: 292638-85-8
acrylic acid methyl ester

: 14035-94-0
dimethyl 2-methylglutarate

Conditions

Conditions	Yield
With hydrogenchloride; aluminum ion-exchanged montmorillonite 1.) -78 deg C, 1 h, CH2Cl2, 2.) r.t.; Yield given. Multistep reaction;

: 35299-08-2
2-Methoxycarbonyl-4-methyl-pentanedioic acid dimethyl ester

: 14035-94-0
dimethyl 2-methylglutarate

Conditions

Conditions	Yield
Stage #1: 2-Methoxycarbonyl-4-methyl-pentanedioic acid dimethyl ester With potassium hydroxide Stage #2: With hydrogenchloride

: 80-62-6
methacrylic acid methyl ester

divinylbenzene: divinylbenzene

: 14035-94-0
dimethyl 2-methylglutarate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: NaOMe / methanol 2.1: KOH 2.2: HCl View Scheme

: 2-diethylamino-6-methoxy-3-methyl-4H-pyran

: 14035-94-0
dimethyl 2-methylglutarate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. HCl 2: TsOH View Scheme

: 67-56-1
methanol

: 18069-17-5
2-methylglutaric acid

A: 14035-94-0
dimethyl 2-methylglutarate

B: 34927-41-8
4-methoxycarbonylpentanoic acid

C: 62115-18-8
4-methoxycarbonyl-2-R-methylbutyric acid

Conditions

Conditions	Yield
at 60℃; for 1h;

...Expand

: 5621-44-3
dimethyl 2-methylenepentanedioate

: 14035-94-0
dimethyl 2-methylglutarate

Conditions

Conditions	Yield
With bis(norbornadiene)rhodium(l)tetrafluoroborate; C61H52N2O2P2; (S)-(phenylcarbamoyl)-N-valine; hydrogen; N-ethyl-N,N-diisopropylamine In dichloromethane at 25℃; under 7500.75 Torr; for 16h; Inert atmosphere; Autoclave;

: 1191-95-3
cyclobutanone

: 616-38-6
carbonic acid dimethyl ester

A: 1119-40-0
Dimethyl glutarate

B: 14035-94-0
dimethyl 2-methylglutarate

C: 1517-15-3
2-methylcyclobutanone

D: 52903-53-4
methyl cyclobutane-2-one-1-carboxylate

E: 10432-55-0
2-Cyclobutylidenecyclobutanone

Conditions

Conditions	Yield
With magnesium oxide at 260℃; for 5h; Autoclave;

...Expand

: 1191-95-3
cyclobutanone

: 616-38-6
carbonic acid dimethyl ester

A: 1119-40-0
Dimethyl glutarate

B: 14035-94-0
dimethyl 2-methylglutarate

C: 1517-15-3
2-methylcyclobutanone

D: 10432-55-0
2-Cyclobutylidenecyclobutanone

Conditions

Conditions	Yield
With magnesium oxide at 260℃; for 5h; Autoclave;

...Expand

: 1191-95-3
cyclobutanone

: 616-38-6
carbonic acid dimethyl ester

A: 1119-40-0
Dimethyl glutarate

B: 14035-94-0
dimethyl 2-methylglutarate

C: 52903-53-4
methyl cyclobutane-2-one-1-carboxylate

D: 10432-55-0
2-Cyclobutylidenecyclobutanone

Conditions

Conditions	Yield
With magnesium oxide at 260℃; for 5h; Autoclave;

...Expand

: 67-56-1
methanol

: 91912-46-8
rac-homocitrato γ-lactone acid

A: 627-93-0
hexanedioic acid dimethyl ester

B: 4339-27-9, 64591-19-1
1,2,4-butanetricarboxylic acid trimethyl ester

C: 14035-95-1
ethylbutanedioic acid dimethyl ester

D: 14035-94-0
dimethyl 2-methylglutarate

Conditions

Conditions	Yield
With 5%-palladium/activated carbon; hydrogen In water at 150℃; under 10343.2 Torr; for 4h; Temperature; Reagent/catalyst;

...Expand

: 67-56-1
methanol

: 20515-19-9, 36781-66-5, 818-58-6
methyl 3-pentenoate

: 201230-82-2
carbon monoxide

A: 627-93-0
hexanedioic acid dimethyl ester

B: 14035-94-0
dimethyl 2-methylglutarate

Conditions

Conditions	Yield
With platinum(II) bis(acetylacetonate); C28H36P2; toluene-4-sulfonic acid at 120℃; under 30402 Torr; for 20h; Sealed tube; Inert atmosphere; Autoclave; Overall yield = 98 percent;

...Expand

: 939403-19-7
methyl 1-{[(benzyloxy)carbonyl]amino}-2-methylpropylphosphinate

: 14035-94-0
dimethyl 2-methylglutarate

: 939403-21-1
dimethyl 2-{[(1-{[(benzyloxy)carbonyl]amino}-2-methylpropyl)(methoxy)phosphoryl]methyl}pentanedioate

Conditions

Conditions	Yield
With sodium methylate In methanol at 20℃;	39.2%

: 939403-20-0
methyl 1-{[(benzyloxy)carbonyl]amino}-2-methylbutylphosphinate

: 14035-94-0
dimethyl 2-methylglutarate

: 939403-22-2
dimethyl 2-{[(1-{[(benzyloxy)carbonyl]amino}-2-methylbutyl)(methoxy)phosphoryl]methyl}pentanedioate

Conditions

Conditions	Yield
With sodium methylate In methanol at 20℃;	34.2%

: 14035-94-0
dimethyl 2-methylglutarate

: 18069-17-5
2-methylglutaric acid

Conditions

Conditions	Yield
(hydrolysis);

: 75-77-4
chloro-trimethyl-silane

: 14035-94-0
dimethyl 2-methylglutarate

: 86554-38-3
2-Methyl-1,5-bis(trimethylsiloxy)-1,5-dimethoxypenta-1,4-diene

Conditions

Conditions	Yield
With lithium diisopropyl amide 1) THF, -78 deg C, 10 min, 2) -78 deg C - room temp.; Yield given. Multistep reaction;
With lithium diisopropyl amide 1.) THF, -78 deg C, 20 min, 2.) room temp, 2 h; Multistep reaction;

: 14035-94-0
dimethyl 2-methylglutarate

: 105-45-3
acetoacetic acid methyl ester

: 107182-00-3
methyl 8-hydroxy-7-(methoxycarbonyl)-2-methyl-1-oxo-1,2,3,4-tetrahydro-3-naphthylacetate

Conditions

Conditions	Yield
With n-butyllithium; calcium acetate; sodium hydride 1.) THF, hexane, 1 h, room temperature, 2.) MeOH, 2 h, reflux; Yield given. Multistep reaction;

: 14035-94-0
dimethyl 2-methylglutarate

: 10171-92-3
(S)-(+)-dimethyl-2-methylglutarate

: 14035-94-0
dimethyl 2-methylglutarate

: 80986-17-0
(R)-(-)-4-methylglutaric acid 1-monomethyl ester

Conditions

Conditions	Yield
With sodium hydroxide; phosphate buffer at 30℃; esterase from Pseudomonas putida MR-2068;
With sodium hydroxide; esterase from Pseudomonas putida MR-2068 In various solvent(s) at 30℃; pH=7.0;

: 50-00-0
formaldehyd

: 14035-94-0
dimethyl 2-methylglutarate

: 34019-71-1
dimethyl 2-methyl-4-methylenepentanedioate

Conditions

Conditions	Yield
With piperidine; pyridine Stetter reaction; Heating;

: 14035-94-0
dimethyl 2-methylglutarate

: 3290-56-0
2-methyl-4-methylenepentanedioic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine; piperidine / Heating 2: ethanolic KOH / 2 h / Heating View Scheme

: 14035-94-0
dimethyl 2-methylglutarate

: anti-dimethyl 2-ethyl-4-methylpentanedioate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: pyridine; piperidine / Heating 2.1: MgBr2*OEt2 / CH2Cl2; diethyl ether / 0.5 h / 20 °C 2.2: n-Bu3SnH; Et3B; O2 / CH2Cl2; diethyl ether; hexane / 4 h / 20 °C View Scheme

: 14035-94-0
dimethyl 2-methylglutarate

: syn-dimethyl 2-ethyl-4-methylpentanedioate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: pyridine; piperidine / Heating 2.1: MgBr2*OEt2 / CH2Cl2; diethyl ether / 0.5 h / 20 °C 2.2: n-Bu3SnH; Et3B; O2 / CH2Cl2; diethyl ether; hexane / 4 h / 20 °C View Scheme

: 14035-94-0
dimethyl 2-methylglutarate

: anti-dimethyl 2-methyl-4-propylpentanedioate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: pyridine; piperidine / Heating 2.1: MgBr2*OEt2 / CH2Cl2; diethyl ether / 0.5 h / 20 °C 2.2: n-Bu3SnH; Et3B; O2 / CH2Cl2; diethyl ether; hexane / 4 h / -78 °C View Scheme
Multi-step reaction with 2 steps 1.1: pyridine; piperidine / Heating 2.1: MgBr2*OEt2 / benzene; diethyl ether / 0.5 h / 20 °C 2.2: n-Bu3SnH; AIBN / benzene; diethyl ether; hexane / 4 h / 70 °C View Scheme

: 14035-94-0
dimethyl 2-methylglutarate

: syn-dimethyl 2-methyl-4-propylpentanedioate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: pyridine; piperidine / Heating 2.1: MgBr2*OEt2 / CH2Cl2; diethyl ether / 0.5 h / 20 °C 2.2: n-Bu3SnH; Et3B; O2 / CH2Cl2; diethyl ether; hexane / 4 h / -78 °C View Scheme
Multi-step reaction with 2 steps 1.1: pyridine; piperidine / Heating 2.1: MgBr2*OEt2 / benzene; diethyl ether / 0.5 h / 20 °C 2.2: n-Bu3SnH; AIBN / benzene; diethyl ether; hexane / 4 h / 70 °C View Scheme

: 14035-94-0
dimethyl 2-methylglutarate

: anti-dimethyl 2-methyl-4-neopentylpentanedioate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: pyridine; piperidine / Heating 2.1: MgBr2*OEt2 / benzene; diethyl ether / 0.5 h / 20 °C 2.2: n-Bu3SnH; AIBN / benzene; diethyl ether; hexane / 3 h / 70 °C View Scheme

: 14035-94-0
dimethyl 2-methylglutarate

: syn-dimethyl 2-methyl-4-neopentylpentanedioate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: pyridine; piperidine / Heating 2.1: MgBr2*OEt2 / benzene; diethyl ether / 0.5 h / 20 °C 2.2: n-Bu3SnH; AIBN / benzene; diethyl ether; hexane / 3 h / 70 °C View Scheme
Multi-step reaction with 2 steps 1.1: pyridine; piperidine / Heating 2.1: MgBr2*OEt2 / CH2Cl2; diethyl ether / 0.5 h / 20 °C 2.2: 100 percent / n-Bu3SnH; Et3B; O2 / CH2Cl2; diethyl ether; hexane / 4 h / -78 °C View Scheme

: 14035-94-0
dimethyl 2-methylglutarate

: anti-dimethyl 2-(cyclohexylmethyl)-4-methylpentanedioate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: pyridine; piperidine / Heating 2.1: MgBr2*OEt2 / benzene; diethyl ether / 0.5 h / 20 °C 2.2: n-Bu3SnH; AIBN / benzene; diethyl ether; hexane / 4 h / 70 °C View Scheme
Multi-step reaction with 2 steps 1.1: pyridine; piperidine / Heating 2.1: MgBr2*OEt2 / CH2Cl2; diethyl ether / 0.5 h / 20 °C 2.2: n-Bu3SnH; Et3B; O2 / CH2Cl2; diethyl ether; hexane / 4 h / -20 °C View Scheme

2-Methylpentanedioic acid dimethyl ester Specification

The Pentanedioic acid, 2-methyl-, 1,5-dimethyl ester, with the CAS registry number 14035-94-0, is also known as Dimethyl 2-Methylglutarate. Its EINECS number is 251-552-6. This chemical's molecular formula is C₈H₁₄O₄ and molecular weight is 174.19. What's more, its systematic name is ethyl 4-chloro-3-oxopentanoate. Its classification codes are: (1)TSCA Flag E [Subject to the Section 5(e) Consent Order of TSCA]; (2)TSCA Flag P [A commenced PMN (Premanufacture Notice) substance].

Physical properties of Pentanedioic acid, 2-methyl-, 1,5-dimethyl ester are: (1)ACD/LogP: 0.97; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.97; (4)ACD/LogD (pH 7.4): 0.97; (5)ACD/BCF (pH 5.5): 3.2; (6)ACD/BCF (pH 7.4): 3.2; (7)ACD/KOC (pH 5.5): 80.02; (8)ACD/KOC (pH 7.4): 80.02; (9)#H bond acceptors: 4; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 6; (12)Polar Surface Area: 52.6 Å²; (13)Index of Refraction: 1.421; (14)Molar Refractivity: 42.62 cm³; (15)Molar Volume: 167.9 cm³; (16)Polarizability: 16.89×10^-24cm³; (17)Surface Tension: 31.3 dyne/cm; (18)Density: 1.037 g/cm³; (19)Flash Point: 90.8 °C; (20)Enthalpy of Vaporization: 44.06 kJ/mol; (21)Boiling Point: 204.4 °C at 760 mmHg; (22)Vapour Pressure: 0.264 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(OC)CCC(C(=O)OC)C
(2)Std. InChI: InChI=1S/C8H14O4/c1-6(8(10)12-3)4-5-7(9)11-2/h6H,4-5H2,1-3H3
(3)Std. InChIKey: ZWKKRUNHAVNSFW-UHFFFAOYSA-N

Product Name

2-Methylpentanedioic acid dimethyl ester

Synthetic route

2-Methylpentanedioic acid dimethyl ester Specification

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