Methyl (R)-(-)-3-hydroxybutyrate

Base Information

• Chemical Name: Methyl (R)-(-)-3-hydroxybutyrate
• CAS No.: 3976-69-0
• Molecular Formula: C5H10O3
• Molecular Weight: 118.133
• Hs Code.: 29181990
• European Community (EC) Number: 223-610-0
• UNII: CL06316S38
• Nikkaji Number: J57.251I
• Wikidata: Q27275514
• Mol file: 3976-69-0.mol

Synonyms:3976-69-0;Methyl (R)-(-)-3-hydroxybutyrate;(R)-Methyl 3-Hydroxybutanoate;methyl (3R)-3-hydroxybutanoate;Methyl (R)-3-hydroxybutyrate;Methyl (R)-3-hydroxybutanoate;Methyl 3-hydroxybutyrate, (-)-;Butanoic acid, 3-hydroxy-, methyl ester, (3R)-;(r)-methyl 3-hydroxybutyrate;UNII-CL06316S38;Methyl 3-hydroxybutyrate, (R)-;Butanoic acid, 3-hydroxy-, methyl ester, (R)-;EINECS 223-610-0;CL06316S38;MFCD00063289;Methyl(R)-(-)-3-hydroxybutyrate;(R)-3-hydroxybutyric acid methyl ester;(R)-(-)-3-Hydroxybutyric Acid Methyl Ester;(R)-(-)-Methyl 3-hydroxybutyrate;methyl 3(R)-hydroxybutyrate;(R)-(-)-3-Hydroxy-n-butyric acid methyl ester;Methyl(R)-3-hydroxybutyrate;methyl 3(R)-hydroxybutanoate;Methyl 3-(R)-hydroxybutyrate;methyl 3-(R)-hydroxybutanoate;methyl (3R)-3-hydroxybutyrate;methyl (R)-3-hydroxy-butyrate;SCHEMBL2544991;methyl (R)-beta-hydroxybutyrate;METHYL 3R-HYDROXYBUTYRATE;(R)-3HB;(R)-3-Hydroxybutyric acid methyl;3-hydroxy-butyric acid methyl ester;BCP15245;AC7720;BBL102284;STL556083;Methyl (R)-3-hydroxybutyrate, 99%;AKOS005137981;AKOS015920086;CS-W011223;GS-3453;HY-W010507;METHYL (-)-3-HYDROXYBUTANOATE;Methyl 3-hydroxybutanoate, (R)-(-)-;AC-25565;FEMA NO. 4450, (-)-;(R)-3-Hydroxy-n-butyric Acid methyl Ester;A6637;AM20100049;H0705;EN300-135784;(|R|)-(-)-3-Hydroxybutyric acid methyl ester;(3R)-3-HYDROXYBUTANOIC ACID METHYL ESTER;W-106405;(-)-(3R)-3-HYDROXYBUTANOIC ACID METHYL ESTER;Q27275514;BUTYRIC ACID, 3-HYDROXY-, METHYL ESTER, D-(-)-;Methyl (R)-3-hydroxybutyrate, puriss., >=99.0% (sum of enantiomers, GC)

Chemical Property of Methyl (R)-(-)-3-hydroxybutyrate

Chemical Property:

• Appearance/Colour: clear colorless liquid
• Vapor Pressure: 0.768mmHg at 25°C
• Refractive Index: n20/D 1.421(lit.)
• Boiling Point: 161.9 °C at 760 mmHg
• PKA: 13.95±0.20(Predicted)
• Flash Point: 71.7 °C
• PSA: 46.53000
• Density: 1.05 g/cm³
• LogP: -0.06970
• Storage Temp.: 0-6°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: Slightly soluble in water.
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 118.062994177
• Heavy Atom Count: 8
• Complexity: 79.7

Purity/Quality:

99% ^*data from raw suppliers

Methyl (R)-(-)-3-Hydroxybutyrate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37-24/25-23

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(CC(=O)OC)O
• Isomeric SMILES: C[C@H](CC(=O)OC)O
• Uses: Methyl (R)-3-hydroxybutyrate may be used in the preparation of (R)-(-)-3-hydroxybutanoic acid and poly-(R)-(-)-3-hydroxybutyrate.

Technology Process of Methyl (R)-(-)-3-hydroxybutyrate

There total 45 articles about Methyl (R)-(-)-3-hydroxybutyrate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

acetoacetic acid methyl ester (105-45-3) → (S)-3-hydroxybutyric acid methyl ester (53562-86-0) + Methyl (R)-3-hydroxybutyrate (3976-69-0)

Guidance literature:

With Ru₂Cl₄-(S)-(2,2'-bis(diphenylphosphino)-1,1'-binaphthyl)2*NEt₃; hydrogen; In methanol; at 35 ℃; for 48h; under 76000.1 Torr; Title compound not separated from byproducts;

DOI:10.1016/0022-328X(92)83466-U

Reference yield: 100.0%

acetoacetic acid methyl ester (105-45-3) → Methyl (R)-3-hydroxybutyrate (3976-69-0)

Guidance literature:

With cat; hydrogen; In methanol; dichloromethane; at 25 ℃; for 48h; under 77572.2 Torr;

DOI:10.1016/S0957-4166(00)86109-1

Reference yield: 100.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + (R)-3-hydroxybutyric acid (625-72-9,26063-00-3,29435-48-1) → Methyl (R)-3-hydroxybutyrate (3976-69-0)

Guidance literature:

In diethyl ether;

DOI:10.1021/ja00395a044

upstream raw materials:

diazomethane

(R)-3-hydroxybutyric acid

3-Hydroxybutyric acid

methanol

Downstream raw materials:

(R)-methyl 3-((4-methoxybenzyl)oxy)butanoate

(R)-4-Triphenylsilanyloxy-butan-2-ol

(2R,3R)-methyl 2-[(benzyloxy)methyl]-3-hydroxybutyrate

methanol

Refernces

• 1、 Sugimura, Takashi,Nakagawa, Satoshi,Kamata, Naoya,Tei, Takahiro,Tajiri, Takashi,Tsukiyama, Ryo-Ichi,Okuyama, Tadashi,Okamoto, Yasuaki. "Ligand-acceleration by a chiral modifier in the enantioselective hydrogenation of methyl acetoacetate on a raney nickel catalyst: Effect of a modifier configuration". . p. 271 - 276. Retrieved 2015.
• 2、 Bartek, Lukas,Kluson, Petr,Cerveny, Libor. "In situ chiral modification of nickel catalysts for enantioselective hydrogenation of methyl acetoacetate". . p. 1642 - 1652. Retrieved 2005.
• 3、 Harada, Tadao,Yamamoto, Mihoko,Onaka, Shinji,Imaida, Motomasa,Ozaki, Hiroshi,et al.. "The Enantioface-differentiating (Asymmetric) Hydrogenation of the C=O Double Bond with Modified Raney Nickel. XXXVI. The Development of Modified Nickel Catalysts with High Enantioface-differentiating Abilities". . p. 2323 - 2329. Retrieved 1981.
• 4、 Saluzzo, Christine,Lamouille, Thierry,Le Guyader, Frederic,Lemaire, Marc. "Synthesis and studies of 6,6′-BINAP derivatives for the heterogeneous asymmetric hydrogenation of methyl acetoacetate". . p. 1141 - 1146. Retrieved 2002.
• 5、 Chen, Hangning,Li, Rong,Wang, Huanling,Yin, Liang,Wang, Fushan,Ma, Jiantai. "Highly efficient enantio-selective hydrogenation of methyl acetoacetate over an improved tartaric acid-modified raney nickel catalyst". . p. 910 - 911. Retrieved 2006.
• 6、 Osawa, Tsutomu,Ando, Masashi,Harada, Tadao,Takayasu, Osamu. "Specific acceleration of the hydrogenation of methyl acetoacetate on enantio-differentiating sites of a tartaric acid-modified nickel catalyst by the addition of acetic acid to the reaction media". . p. 1371 - 1372. Retrieved 2005.
• 7、 Brunner, Henri,Muschiol, Manfred,Wischert, Thomas,Wiehl, Juergen. "ENANTIOSELECTIVE CATALYSIS. 54. HYDROGENATION OF METHYL ACETOACETATE USING NICKEL POWDER MODIFIED WITH NaBr/(R,R)-TARTARIC ACID". . p. 159 - 162. Retrieved 1990.
• 8、 Barbaro, Pierluigi,Bianchini, Claudio,Giambastiani, Giuliano,Oberhauser, Werner,Bonzi, Laura Morassi,Rossi, Filippo,Dal Santo, Vladimiro. "Recycling asymmetric hydrogenation catalysts by their immobilisation onto ion-exchange resins". . p. 1783 - 1784. Retrieved 2004.
• 9、 Reis, Joel S.,Andrade, Leandro H.. "Lipase-catalyzed kinetic resolution of β-borylated carboxylic esters". . p. 1294 - 1300. Retrieved 2012.
• 10、 Tai, Akira,Imachi, Yoshimi,Harada, Tadao,Izumi, Yoshiharu. "EMBEDDED NICKEL CATALYST IN POLYMER". . p. 1651 - 1652. Retrieved 1981.