(r)-5-(Hydroxymethyl)dihydrofuran-2(3h)-one

Base Information

• Chemical Name: (r)-5-(Hydroxymethyl)dihydrofuran-2(3h)-one
• CAS No.: 52813-63-5
• Molecular Formula: C5H8O3
• Molecular Weight: 116.117
• Hs Code.: 2932209090
• European Community (EC) Number: 801-118-2
• DSSTox Substance ID: DTXSID201254377
• Nikkaji Number: J881.984J
• Mol file: 52813-63-5.mol

Synonyms:52813-63-5;(r)-5-(hydroxymethyl)dihydrofuran-2(3h)-one;(5R)-5-(hydroxymethyl)oxolan-2-one;(R)-5-Hydroxymethyldihydrofuran-2-one;(r)-5-hydroxymethyl-dihydro-furan-2-one;(R)-(-)-Dihydro-5-(hydroxymethyl)-2(3H)-furanone;(r)-gamma-hydroxymethyl-gamma-butyro-lactone;(r)-5-(hydroxymethyl)-dihydrofuran-2(3h)-one;2(3H)-Furanone, dihydro-5-(hydroxymethyl)-, (5R)-;SCHEMBL931042;NSISJFFVIMQBRN-SCSAIBSYSA-N;DTXSID201254377;BCP23214;MFCD00040528;AKOS016842835;AC-6629;(R)-4-(hydroxymethyl)-4-butyrolactone;AS-37602;(r)-(-)-g-hydroxymethyl- g-butyrolactone;5alpha-(Hydroxymethyl)tetrahydrofuran-2-one;AM20090484;CS-0046919;EN300-99298;(5R)-5-(hydroxymethyl)dihydrofuran-2(3H)-one;(r)-(-)-gamma-hydroxymethyl-gamma-butyrolactone;(5R)-Dihydro-5-(hydroxymethyl)-2(3H)-furanone;A847751;(c)zR(c){-Gamma-hydroxymethyl-gamma-butyro-lactone;l-dihydro-5-(hydroxymethyl)-2(3h)-furanone (r-);Q-103495;(r)-(+)-dihydro-5-(hydroxymethyl)-2(3h)-furanone;R)-(-)-DIHYDRO-5-(HYDROXYMETHYL)-2(3H)-;(R)-(-)-Dihydro-5-(hydroxymethyl)-2(3H)-furanone, 97%;5-Hydroxymethyl-dihydro-furan-2-one;(R)-5-(Hydroxymethyl)dihydrofuran-2(3H)-one

Chemical Property of (r)-5-(Hydroxymethyl)dihydrofuran-2(3h)-one

Chemical Property:

• Vapor Pressure: 6.02E-05mmHg at 25°C
• Refractive Index: n20/D 1.471
• Boiling Point: 308.9 °C at 760 mmHg
• Flash Point: 146 °C
• PSA: 46.53000
• Density: 1.224 g/cm³
• LogP: -0.31570
• Storage Temp.: 2-8°C
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 116.047344113
• Heavy Atom Count: 8
• Complexity: 99.8

Purity/Quality:

97% ^*data from raw suppliers

(R)-(?)-Dihydro-5-(hydroxymethyl)-2(3H)-furanone 97% ^*data from reagent suppliers

Safty Information:

• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(=O)OC1CO
• Isomeric SMILES: C1CC(=O)O[C@H]1CO
• Uses: Versatile chiral synthon used in the synthesis of natural and unnatural products.

Technology Process of (r)-5-(Hydroxymethyl)dihydrofuran-2(3h)-one

There total 4 articles about (r)-5-(Hydroxymethyl)dihydrofuran-2(3h)-one 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: 43.0%

ethyl 3-(oxiran-2-yl)propanoate (73697-60-6) → (5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran (32780-06-6) + (5R)-2,3,4,5-tetrahydro-5-hydroxymethyl-2-furanone (52813-63-5) + (S)-ethyl 3-(oxiran-2-yl)propanoate (128969-94-8)

Guidance literature:

With (S,S)-[N,N-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexane-diamino]cobalt(III) acetate; In water; at 20 ℃; for 30h; Title compound not separated from byproducts;

DOI:10.1039/b003793l

Reference yield:

(5-oxotetrahydrofuran-2-yl)methyl acetate (5904-80-3,79580-69-1,112607-21-3,112709-12-3) → (5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran (32780-06-6) + (5R)-2,3,4,5-tetrahydro-5-hydroxymethyl-2-furanone (52813-63-5) + (S)-(+)-dihydro-5-(hydroxymethyl)-2(3H)-furanone acetate (79580-69-1) + (R)-(-)-dihydro-5-(hydroxymethyl)-2(3H)-furanone acetate

Guidance literature:

With lipase SP; water; In acetone; at 35 ℃; for 0.2h; Title compound not separated from byproducts; pH 7.2, phosphate buffer;

DOI:10.1021/jo981184r

Reference yield:

(5-oxotetrahydrofuran-2-yl)methyl acetate (5904-80-3,79580-69-1,112607-21-3,112709-12-3) → (5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran (32780-06-6) + (5R)-2,3,4,5-tetrahydro-5-hydroxymethyl-2-furanone (52813-63-5)

Guidance literature:

With Chromobacterium Viscosum lipase; sodium hydroxide; In aq. phosphate buffer; acetone; at 35 ℃; pH=7.2;

DOI:10.1002/adsc.201400510

upstream raw materials:

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran

(5-oxotetrahydrofuran-2-yl)methyl acetate

ethyl 3-(oxiran-2-yl)propanoate

Downstream raw materials:

(5R)-phenylseleno-5-methyldihydro-2(3H)-furanone

(R)-(-)-γ-benzyloxymethyl-γ-butyrolactone

(R)-tetrahydro-5-oxo-2-furancarbaldehyde

(S)-(-)-Tetrahydro-5-oxo-2-furancarboxaldehyde