(2R)-2-hydroxy-2-methylbutanoic acid

Base Information

• Chemical Name: (2R)-2-hydroxy-2-methylbutanoic acid
• CAS No.: 37505-02-5
• Molecular Formula: C5H10O3
• Molecular Weight: 118.13
• Hs Code.: 2918199090
• DSSTox Substance ID: DTXSID20426960
• Nikkaji Number: J1.300.861B
• Wikidata: Q82239736
• Mol file: 37505-02-5.mol

Synonyms:37505-02-5;(R)-2-Hydroxy-2-methylbutyric acid;(2R)-2-hydroxy-2-methylbutanoic acid;SCHEMBL2327762;DTXSID20426960;(R)-2-Hydroxy-2-methylbutanoic acid;(R)-2-HYDROXY-2-METHYLBUTYRICACID;D78566

Chemical Property of (2R)-2-hydroxy-2-methylbutanoic acid

Chemical Property:

• Boiling Point: 237.6 °C at 760 mmHg
• Flash Point: 111.8 °C
• PSA: 57.53000
• Density: 1.144 g/cm³
• LogP: 0.23200
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 118.062994177
• Heavy Atom Count: 8
• Complexity: 99.8

Purity/Quality:

99% ^*data from raw suppliers

(R)-(-)-2-Hydroxy-2-methylbutyricAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C)(C(=O)O)O
• Isomeric SMILES: CC[C@](C)(C(=O)O)O
• Uses: (R)-(-)-2-Hydroxy-2-methylbutyric Acid is derived from (S)-(-)-1-(1-Naphthyl)ethylamine (N368460), which is used in the asymmetric synthesis of α-cyanocarboxylates. Also used in the synthesis of chiral imadazolin-2-ylidene ligands used in organometallic catalysis. Chiral/Asymmetric synthesis.

Technology Process of (2R)-2-hydroxy-2-methylbutanoic acid

There total 13 articles about (2R)-2-hydroxy-2-methylbutanoic acid 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: 98.0%

(3S,8aS)-3-ethyl-3-methyl-1,4-dioxo-3,4,6,7,8,8a-hexahydro-1H-pyrrolo<2,1-c><1,4>oxazine (63742-11-0) → (R)-(-)-2-hydroxy-2-methylbutyric acid (37505-02-5)

Guidance literature:

With potassium hydroxide; for 11h; Heating;

Reference yield: 97.0%

(1S,2S,5'R)-N,N-diisopropyl [2-spiro-2'-(5'-ethyl-5'-methyl-1',3'-dioxolane-4'-one)-7,7-dimethylbicyclo[2.2.1]hept-1-yl]methanesulfonamide (256393-12-1) → (R)-(-)-2-hydroxy-2-methylbutyric acid (37505-02-5) + (1S)-(+)-N,N-diisopropyl-10-camphorsulfonamide (96323-05-6)

Guidance literature:

With sodium hydroxide; In methanol; at 60 ℃; for 4h;

DOI:10.1021/ol9910666

Reference yield:

(R)-3-methyl-1-pentyn-3-ol hydrogen phthalate (39939-14-5) → (R)-(-)-2-hydroxy-2-methylbutyric acid (37505-02-5)

Guidance literature:

Multi-step reaction with 2 steps

1: HgO, CF₃CO₂H, BF₃-Et₂O

2: (i) TsOH, aq. dioxane, (ii) NaOBr

With boron trifluoride diethyl etherate; trifluoroacetic acid; mercury(II) oxide;

DOI:10.1021/ja00783a040

upstream raw materials:

2-hydroxy-2-methylbutyric acid

1-((E)-2-methyl-but-2-enoyl)-L-proline

(R)-2,2-dimethoxy-3-methyl-pentan-3-ol

(3S,8aS)-3-ethyl-3-methyl-1,4-dioxo-3,4,6,7,8,8a-hexahydro-1H-pyrrolo<2,1-c><1,4>oxazine

Downstream raw materials:

R-2-(4-nitro-phenoxy)-2-methylbutanoic acid

(R)-2-benzyloxy-2-methylbutanoic acid

(R)-2-Methyl-1,1-diphenyl-butane-1,2-diol

2-Hydroxy-N-[2-(2-hydroxy-2-methyl-butyrylamino)-phenyl]-2-methyl-butyramide

Refernces

• 1、 Cabirol, Fabien L.,Pei, Loo Tan,Tay, Benson,Cheng, Shiryn,Hanefeld, Ulf,Sheldon, Roger A.. "Linum usitatissimum hydroxynitrile lyase cross-linked enzyme aggregates: A recyclable enantioselective catalyst". experimental part. p. 2329 - 2338. Retrieved 2009/10/23.
• 2、 Chang, Jia-Wen,Jang, Der-Pin,Uang, Biing-Jiun,Liao, Fen-Ling,Wang, Sue-Lein. "Enantioselective synthesis of α-hydroxy acids employing (1S)-(+)-N,N-diisopropyl-10-camphorsulfonamide as chiral auxiliary". . p. 2061 - 2063. Retrieved 2008/02/09.