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72657-23-9

Basic Information
CAS No.: 72657-23-9
Name: Propanoic acid,3-hydroxy-2-methyl-, methyl ester, (2R)-
Molecular Structure:
Molecular Structure of 72657-23-9 (Propanoic acid,3-hydroxy-2-methyl-, methyl ester, (2R)-)
Formula: C5H10 O3
Molecular Weight: 118.13
Synonyms: Propanoic acid,3-hydroxy-2-methyl-, methyl ester, (R)-; (-)-Methyl b-hydroxyisobutyrate; (2R)-3-Hydroxy-2-methylpropionicacid methyl ester; (R)-(-)-3-Hydroxy-2-methylpropionic acid methyl ester;(R)-3-Hydroxy-2-methylpropionic acid methyl ester;(R)-3-Hydroxy-2-methylpropionic acid methyl ester; Methyl(2R)-3-hydroxy-2-methylpropanoate; Methyl (2R)-3-hydroxy-2-methylpropionate;Methyl (R)-(-)-3-hydroxy-2-methylpropionate; Methyl(R)-(-)-3-hydroxy-2-methylpropionate; Methyl (R)-3-hydroxy-2-methylpropanoate;Methyl (R)-3-hydroxy-2-methylpropionate; Methyl (R)-3-hydroxyisobutanoate;Methyl (R)-b-hydroxyisobutyrate; R-(-)-Rocheester
EINECS:
Density: 1.066
Melting Point:
Boiling Point: 76-77 °C12 mm Hg(lit.)
Flash Point: 80 ºC
Solubility:
Appearance: Clear Colorless Oil
Hazard Symbols: R10:;
Risk Codes: R10   
Safety:
Risk Statements 10
Safety Statements 16
WGK Germany 3
Transport Information:
PSA: 46.53000
LogP: -0.21220
Synthetic route

C16H24O3Si

72657-23-9

methyl (R)-3-hydroxy-2-methylpropionate

Conditions
ConditionsYield
With hydrogen; palladium 10% on activated carbon88%
1910-47-0

(2R)-3-hydroxy-2-methylpropanoic acid

72657-23-9

methyl (R)-3-hydroxy-2-methylpropionate

Conditions
ConditionsYield
In diethyl ether86%
56850-58-9, 59965-24-1, 74924-27-9, 112068-34-5

methyl (2R)-3-(benzyloxy)-2-methylpropanoate

72657-23-9

methyl (R)-3-hydroxy-2-methylpropionate

Conditions
ConditionsYield
With palladium on activated charcoal; hydrogen In methanol at 50℃; Industrial scale;84%
212051-35-9

(R)-methyl 3-((4-methoxybenzyl)oxy)-2-methylpropanoate

72657-23-9

methyl (R)-3-hydroxy-2-methylpropionate

Conditions
ConditionsYield
With t-butyl bromide In acetonitrile for 0.833333h; Reflux; chemoselective reaction;72%
15484-46-5

methyl 2-hydroxymethylacrylate

72657-23-9

methyl (R)-3-hydroxy-2-methylpropionate

Conditions
ConditionsYield
With glucose dehydrogenase; potassium phosphate; D-glucose; ene reductase YqjM wild type enzyme; NADPH In 2-methyltetrahydrofuran; aq. phosphate buffer at 30℃; pH=7.5; Reagent/catalyst; Inert atmosphere; Enzymatic reaction; enantioselective reaction;58%
With bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; (Rc,Ra)-THNAPhos; hydrogen In dichloromethane at 20℃; under 7500.75 Torr; for 24h; optical yield given as %ee;
With bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; 1-(3-(diphenylphosphanyl)phenyl)urea; (2S)-methyl (S)-2-(3,5-dioxa-4-phosphacyclohepta[2,1-a;3,4-a']dinaphthalen-4-ylamino)-2-isobutylethanoate; hydrogen In dichloromethane at 24.84℃; under 7500.75 Torr; for 16h;

methyl (2R,5S,E)-5-((tert-butoxycarbonyl)amino)-2-methyl-5-phenylpent-3-enoate

72657-23-9

methyl (R)-3-hydroxy-2-methylpropionate

Conditions
ConditionsYield
Stage #1: methyl (2R,5S,E)-5-((tert-butoxycarbonyl)amino)-2-methyl-5-phenylpent-3-enoate With ozone In methanol at -78℃;
Stage #2: With sodium tetrahydroborate In methanol at 0 - 20℃;
48%

A

80657-57-4

3-hydroxy-(2S)-methylpropionate

B

72657-23-9

methyl (R)-3-hydroxy-2-methylpropionate

Conditions
ConditionsYield
In diethyl ether Yield given. Yields of byproduct given. Title compound not separated from byproducts;
15484-46-5

methyl 2-hydroxymethylacrylate

A

80657-57-4

3-hydroxy-(2S)-methylpropionate

B

72657-23-9

methyl (R)-3-hydroxy-2-methylpropionate

Conditions
ConditionsYield
With hydrogen; {(-)-1,2-bis(2R,5R)-2,5-dimethylphospholanobenzene(cyclooctadiene)rhodium(l)} triflate In methanol at 30℃; under 3000.3 Torr; Product distribution; Further Variations:; Catalysts;
With hydrogen; Ru(cod)(η3-methylallyl)2/(R)-SYNPHOS/HBF4 In methanol at 50℃; under 15001.5 Torr; for 23h; Title compound not separated from byproducts.;
With hydrogen; p-benzoquinone; [RuH(η6-cycloocta-1,3,5-triene)(S)-SYNPHOS]BF4 In methanol at 15℃; under 15001.5 Torr; for 23h; Title compound not separated from byproducts.;
64809-29-6

methyl 3-hydroxy-2-methylpropanoate

A

80657-57-4

3-hydroxy-(2S)-methylpropionate

B

72657-23-9

methyl (R)-3-hydroxy-2-methylpropionate

Conditions
ConditionsYield
With [Rh(dppb)(COD)]BF4; hydrogen In methanol at 20℃; under 45004.5 Torr; for 20h;
With capillary column subsequently coated with 1) Co(d-Cam)1/2(bdc)1/2(tmdpy) (d-Cam=d-camphoric acid,bdc=1,4-benzenedicarboxylic acid, tmdpy=4,4’-trimethylenedipyridine), 2) peramylated β-cyclodextrin at 93℃; Reagent/catalyst; Resolution of racemate;
110-87-2

3,4-dihydro-2H-pyran

72657-23-9

methyl (R)-3-hydroxy-2-methylpropionate

88557-53-3

(R)-2-Methyl-3-(tetrahydro-pyran-2-yloxy)-propionic acid methyl ester

Conditions
ConditionsYield
With toluene-4-sulfonic acid In tetrahydrofuran Ambient temperature;100%
With pyridinium p-toluenesulfonate In dichloromethane at 20℃; Inert atmosphere;100%
With toluene-4-sulfonic acid In diethyl ether at 20℃;99%
72657-23-9

methyl (R)-3-hydroxy-2-methylpropionate

18162-48-6

tert-butyldimethylsilyl chloride

105859-44-7

methyl (R)-2-methyl-3-[(tert-butyldimethylsilyl)oxy]propionate

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 5℃; Etherification; silylation;100%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 3h;100%
With 1H-imidazole; dmap In dichloromethane at 0 - 20℃; Inert atmosphere;100%
72657-23-9

methyl (R)-3-hydroxy-2-methylpropionate

882-33-7

diphenyldisulfane

121783-48-0

(S)-2-methyl-3-(phenylsulfanyl)propanoic acid methyl ester

Conditions
ConditionsYield
With tributylphosphine In acetonitrile for 4.5h; Ambient temperature;100%
With tributylphosphine In N,N-dimethyl-formamide at 0 - 20℃; for 4h;95%
72657-23-9

methyl (R)-3-hydroxy-2-methylpropionate

58479-61-1

tert-butylchlorodiphenylsilane

95514-03-7

(R)-methyl 3-(tert-butyl(diphenyl)silyloxy)-2-methylpropanoate

Conditions
ConditionsYield
With 1H-imidazole In dichloromethane Ambient temperature;100%
With 1H-imidazole In dichloromethane100%
With 1H-imidazole In N,N-dimethyl-formamide Alkylation;100%
72657-23-9

methyl (R)-3-hydroxy-2-methylpropionate

89238-99-3

O-(4-methoxybenzyl)-trichloroacetimidate

212051-35-9

(R)-methyl 3-((4-methoxybenzyl)oxy)-2-methylpropanoate

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate In dichloromethane at 20℃;100%
With camphor-10-sulfonic acid In dichloromethane for 16h;98%
With camphor-10-sulfonic acid In hexane; dichloromethane at 20℃; for 12h; Inert atmosphere;96%
13154-24-0

triisopropylsilyl chloride

72657-23-9

methyl (R)-3-hydroxy-2-methylpropionate

232280-22-7

methyl (2R)-2-methyl-3-[(1,1,1-triisopropylsilyl)oxy]propanoate

Conditions
ConditionsYield
With 1H-imidazole; dmap In N,N-dimethyl-formamide at 20℃; for 72h; silylation;100%
With 1H-imidazole; dmap In dichloromethane at 20℃;100%
With 1H-imidazole In N,N-dimethyl-formamide Ambient temperature;99%
72657-23-9

methyl (R)-3-hydroxy-2-methylpropionate

40615-36-9

4,4'-dimethoxytrityl chloride

286458-65-9

(R)-3-[Bis-(4-methoxy-phenyl)-phenyl-methoxy]-2-methyl-propionic acid methyl ester

Conditions
ConditionsYield
With 2,3,5-trimethyl-pyridine In dichloromethane at 25℃; Substitution;100%
With pyridine at 20℃; for 4h;
With 2,4,6-trimethyl-pyridine In dichloromethane at 0℃;
994-30-9

triethylsilyl chloride

72657-23-9

methyl (R)-3-hydroxy-2-methylpropionate

343764-58-9

methyl (R)-2-methyl-3-(triethylsilyl)oxypropanoate

Conditions
ConditionsYield
With 1H-imidazole; dmap In dichloromethane at 0 - 20℃; Inert atmosphere;100%
With 1H-imidazole; dmap99%
With 1H-imidazole; dmap In dichloromethane at 0 - 20℃; for 4h;
With 1H-imidazole Inert atmosphere;
72657-23-9

methyl (R)-3-hydroxy-2-methylpropionate

76-83-5

trityl chloride

methyl (R)-(-)-3-trityloxy-2-methylpropionate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;100%
With dmap; triethylamine In dichloromethane at 20℃; for 18h; Inert atmosphere; Cooling with ice;90%
With dmap; triethylamine In dichloromethane at 20℃;63%
72657-23-9

methyl (R)-3-hydroxy-2-methylpropionate

3019-71-4

Trichloroacetyl isocyanate

(R)-2-Methyl-3-(2,2,2-trichloro-acetylcarbamoyloxy)-propionic acid methyl ester

Conditions
ConditionsYield
In dichloromethane at 20℃; for 1h;100%
In dichloromethane at 20℃; for 1h;
72657-23-9

methyl (R)-3-hydroxy-2-methylpropionate

149-30-4

2-Mercaptobenzothiazole

(S)-3-(Benzothiazol-2-ylsulfanyl)-2-methyl-propionic acid methyl ester

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran Mitsunobu reaction;100%
72657-23-9

methyl (R)-3-hydroxy-2-methylpropionate

212051-35-9

(R)-methyl 3-((4-methoxybenzyl)oxy)-2-methylpropanoate

Conditions
ConditionsYield
With trifluorormethanesulfonic acid In diethyl ether at 20℃; for 18h; Inert atmosphere;100%
110-87-2

3,4-dihydro-2H-pyran

72657-23-9

methyl (R)-3-hydroxy-2-methylpropionate

methyl (R)-(-)-3-hydroxy-2-methylpropionate THP ether

Conditions
ConditionsYield
With toluene-4-sulfonic acid In diethyl ether Ambient temperature;99%
72657-23-9

methyl (R)-3-hydroxy-2-methylpropionate

75-16-1

methylmagnesium bromide

73295-16-6

(R)-2,3-dimethyl-1,3-butanediol

Conditions
ConditionsYield
In diethyl ether at 0 - 25℃; for 1.5h;99%
In tetrahydrofuran at -10℃; for 3h; Grignard Reaction; Inert atmosphere;77%
In diethyl ether at 0 - 20℃; for 3h;72%
In tetrahydrofuran; diethyl ether57%
In tetrahydrofuran; diethyl ether at 0℃; for 2h;57%
72657-23-9

methyl (R)-3-hydroxy-2-methylpropionate

107-30-2

chloromethyl methyl ether

112763-36-7

(R)-(-)-methyl 3-(methoxymethoxy)-2-methylpropionate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane for 3h; Ambient temperature;99%
With N-ethyl-N,N-diisopropylamine In dichloromethane for 3h; Ambient temperature;99%
With diisopropylamine In dichloromethane for 16h; Ambient temperature;99%
72657-23-9

methyl (R)-3-hydroxy-2-methylpropionate

98-59-9

p-toluenesulfonyl chloride

84341-94-6

methyl (R)-2-methyl-3-[(4'-toluenesulfonyl)oxy]propionate

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 20℃; for 1h;99%
With dmap; triethylamine In dichloromethane at 20℃; for 12h; Cooling with ice;98%
With triethylamine In dichloromethane at 20℃; for 12h;98%
72657-23-9

methyl (R)-3-hydroxy-2-methylpropionate

108-24-7

acetic anhydride

73295-10-0, 96641-50-8

Methyl (R)(-)-3-acetoxy-2-methylpropanoate

Conditions
ConditionsYield
With 2,6-di-tert-butyl-pyridine; sodium tetracarbonyl cobaltate In acetonitrile for 12h;99%
72657-23-9

methyl (R)-3-hydroxy-2-methylpropionate

1,3-diallyl-6-[4-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)-benzyloxy]-1,3,5-triazine-2,4(1H,3H)-dione

methyl (2R)-3-[4-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)-benzyloxy]-2-methylpropionate

Conditions
ConditionsYield
With 2,6-di-tert-butylpyridin-1-ium trifluoromethanesulfonate In 1,4-dioxane at 20℃; for 4h; Molecular sieve;99%
72657-23-9

methyl (R)-3-hydroxy-2-methylpropionate

109-92-2

ethyl vinyl ether

910131-57-6

methyl (R)-3-(1'-ethoxyethoxy)-2-methylpropanoate

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate In dichloromethane for 4h; Ambient temperature;98.1%
With toluene-4-sulfonic acid In diethyl ether at 20℃; for 2h;93%
With pyridinium p-toluenesulfonate In dichloromethane for 0.25h; Ambient temperature;
With pyridinium p-toluenesulfonate
With pyridinium p-toluenesulfonate In dichloromethane at 20℃;
72657-23-9

methyl (R)-3-hydroxy-2-methylpropionate

212051-23-5

3,4-dimethoxybenzyl 2,2,3,3,3-pentafluoropropionimidate

212051-39-3

methyl 3-(3,4-dimethoxy-benzyloxy)-2-(R)-methyl-propionate

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate In dichloromethane at 20℃; for 1h;98%
72657-23-9

methyl (R)-3-hydroxy-2-methylpropionate

86-93-1

1-Phenyl-1H-tetrazole-5-thiol

845734-61-4

(2S)-methyl-3-(1-phenyl-1H-tetrazol-5-ylsulfanyl)propionic acid methyl ester

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 5h;98%
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃;98%

2-benzyloxy-1-methylpyridinium triflate

72657-23-9

methyl (R)-3-hydroxy-2-methylpropionate

56850-58-9, 59965-24-1, 74924-27-9, 112068-34-5

methyl (2R)-3-(benzyloxy)-2-methylpropanoate

Conditions
ConditionsYield
In α,α,α-trifluorotoluene at 120℃; for 0.333333h; Microwave irradiation;98%
With magnesium oxide In α,α,α-trifluorotoluene at 80℃; for 24h;85%
With magnesium oxide at 83℃; for 24h; Inert atmosphere;82%
With magnesium oxide In 1,2-dichloro-ethane Heating;72%
3587-60-8

Benzyloxymethyl chloride

72657-23-9

methyl (R)-3-hydroxy-2-methylpropionate

116021-11-5

(2R)-3-benzyloxymethoxy-2-methylpropionic acid methyl ester

Conditions
ConditionsYield
Stage #1: Benzyloxymethyl chloride; methyl (R)-3-hydroxy-2-methylpropionate With N-ethyl-N,N-diisopropylamine In dichloromethane at -78 - 20℃; for 16h;
Stage #2: With tetra-(n-butyl)ammonium iodide In dichloromethane at 20℃; for 3h;
97%
Stage #1: Benzyloxymethyl chloride; methyl (R)-3-hydroxy-2-methylpropionate With N-ethyl-N,N-diisopropylamine In dichloromethane at -78 - 20℃;
Stage #2: With tetra-(n-butyl)ammonium iodide at 20℃; for 3h;
97%
With N-ethyl-N,N-diisopropylamine In dichloromethane for 44h; Ambient temperature;
72657-23-9

methyl (R)-3-hydroxy-2-methylpropionate

149093-02-7

methyl (S)-3-iodo-2-methylpropanoate

Conditions
ConditionsYield
With 1H-imidazole; iodine; triphenylphosphine In diethyl ether; acetonitrile at 0 - 20℃; for 2.5h;97%
Stage #1: methyl (R)-3-hydroxy-2-methylpropionate With dmap; triethylamine; p-toluenesulfonyl chloride In dichloromethane at 0 - 20℃; for 2.5h;
Stage #2: With sodium iodide In acetonitrile at 70℃; for 16h;
72%
1.) tosylation; 2.) iodination; Multistep reaction;

4-methoxybenzyl trichloroacetimidate

72657-23-9

methyl (R)-3-hydroxy-2-methylpropionate

212051-35-9

(R)-methyl 3-((4-methoxybenzyl)oxy)-2-methylpropanoate

Conditions
ConditionsYield
With lanthanum(lll) triflate In toluene at 0 - 20℃; for 16h; Inert atmosphere;97%
470662-82-9

(R)-3,4-dihydro-2H-benzo[b][1,4]oxathiepin-3-amine

72657-23-9

methyl (R)-3-hydroxy-2-methylpropionate

1169760-41-1

N-[3,4-dihydro-1,5-benzoxathiepin-3-yl]-(R)-(3-hydroxy-2-(R)-methyl)propionamide

Conditions
ConditionsYield
Stage #1: (R)-3,4-dihydro-2H-benzo[b][1,4]oxathiepin-3-amine With diisobutylaluminium hydride In tetrahydrofuran at 10 - 20℃; Inert atmosphere;
Stage #2: methyl (R)-3-hydroxy-2-methylpropionate In tetrahydrofuran at -10 - 50℃;
Stage #3: With water; Rochelle's salt In tetrahydrofuran for 2h; Inert atmosphere;
96.8%
72657-23-9

methyl (R)-3-hydroxy-2-methylpropionate

4-(4,6-diphenoxy-1,3,5-triazine-2-yl)-4-benzylmorpholinium trifluoromethanesulfonate

56850-58-9, 59965-24-1, 74924-27-9, 112068-34-5

methyl (2R)-3-(benzyloxy)-2-methylpropanoate

Conditions
ConditionsYield
With magnesium oxide In 1,2-dimethoxyethane at 20℃; for 2h; Inert atmosphere;96%
72657-23-9

methyl (R)-3-hydroxy-2-methylpropionate

81927-55-1

O-benzyl 2,2,2-trichloroacetimidate

56850-58-9, 59965-24-1, 74924-27-9, 112068-34-5

methyl (2R)-3-(benzyloxy)-2-methylpropanoate

Conditions
ConditionsYield
With trifluoroacetic acid In tetrahydrofuran at 20℃; for 16h; Inert atmosphere;95%
With trifluorormethanesulfonic acid In dichloromethane at 0℃;91%
With trifluorormethanesulfonic acid In dichloromethane; cyclohexane at 20℃; for 3h;88%
72657-23-9

methyl (R)-3-hydroxy-2-methylpropionate

212051-26-8

3,4-dimethoxybenzyl 2,2,3,3,4,4,4-heptafluorobutyrimidate

212051-39-3

methyl 3-(3,4-dimethoxy-benzyloxy)-2-(R)-methyl-propionate

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate In dichloromethane at 20℃; for 1h;95%
72657-23-9

methyl (R)-3-hydroxy-2-methylpropionate

1,3-diallyl-6-(4-nitrobenzyloxy)-1,3,5-triazine-2,4(1H,3H)-dione

methyl (2R)-3-[(4-nitrobenzyl)oxy]-2-methylpropionate

Conditions
ConditionsYield
With trifluorormethanesulfonic acid In 1,4-dioxane at 50℃; for 4h; Molecular sieve;95%
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  • (R)-(-)-3-Hydroxyisobutyric acid methyl ester

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    72657-23-9

    (R)-(-)-3-Hydroxyisobutyric acid methyl ester

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  • (R)-(-)-3-hydroxy-2-methylpropionic acid methyl ester

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    72657-23-9

    (R)-(-)-3-hydroxy-2-methylpropionic acid methyl ester

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  • (r)-(-)-3-hydroxy-2-methylpropionic Acid Methyl Ester CAS NO.72657-23-9

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    72657-23-9

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    (r)-(-)-3-hydroxy-2-methylpropionic Acid Methyl Ester CAS NO.72657-23-9

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  • Methyl (R)-(-)-3-hydroxy-2-methylpropionate

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    72657-23-9

    Methyl (R)-(-)-3-hydroxy-2-methylpropionate

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  • (R)-(-)-3-Hydroxyisobutyric acid methyl ester

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    72657-23-9

    (R)-(-)-3-Hydroxyisobutyric acid methyl ester

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  • Methyl (R)-(-)-3-hydroxy-2-methylpropionate

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    72657-23-9

    Methyl (R)-(-)-3-hydroxy-2-methylpropionate

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Chemistry

Molecular structure of Methyl (R)-(-)-3-hydroxy-2-methylpropionate (CAS NO.72657-23-9) is:

Product Name: Methyl (R)-(-)-3-hydroxy-2-methylpropionate
CAS Registry Number: 72657-23-9
IUPAC Name: methyl 3-Hydroxy-2-methylpropanoate
Molecular Weight: 118.1311 [g/mol]
Molecular Formula: C5H10O3
XLogP3-AA: -0.1
H-Bond Donor: 1
H-Bond Acceptor: 3
Refractive index: n20/D 1.425
Storage temp.: 2-8 °C
Surface Tension: 33.218 dyne/cm
Density: 1.051 g/cm3
Flash Point: 81.111 °C
Enthalpy of Vaporization: 47.893 kJ/mol
Boiling Point: 175.048 °C at 760 mmHg
Vapour Pressure: 0.361 mmHg at 25 °C 

Uses

 Methyl (R)-(-)-3-hydroxy-2-methylpropionate (CAS NO.72657-23-9) can be used in chiral derivative of 3-Hydroxyisobutyrate.

Safety Profile

Safty information about Methyl (R)-(-)-3-hydroxy-2-methylpropionate (CAS NO.72657-23-9) is:
Risk Statements: 10 
R10:Flammable.
Safety Statements: 16 
S16:Keep away from sources of ignition.
WGK Germany: 3

Specification

 Methyl (R)-(-)-3-hydroxy-2-methylpropionate , its cas register number is 72657-23-9. It also can be called Propanoic acid,3-hydroxy-2-methyl-, methyl ester, (2R)- ; (-)-Methyl D-beta-hydroxyisobutyrate .It is a clear colorless oil.