[2-(Hydroxymethyl)oxolan-2-yl]methanol

Base Information

• Chemical Name: [2-(Hydroxymethyl)oxolan-2-yl]methanol
• CAS No.: 13386-57-7
• Molecular Formula: C6H12O3
• Molecular Weight: 132.1577
• European Community (EC) Number: 829-498-5
• NSC Number: 97504
• DSSTox Substance ID: DTXSID30294632
• Nikkaji Number: J324.685J
• Wikidata: Q82034017
• Mol file: 13386-57-7.mol

Synonyms:[2-(hydroxymethyl)oxolan-2-yl]methanol;13386-57-7;(Tetrahydrofuran-2,2-diyl)dimethanol;tetrahydrofuran-2,2-diyldimethanol;2,2-bis(hydroxymethyl)-tetrahydrofuran;NSC97504;SCHEMBL38417;bis(hydroxymethyl) tetrahydrofuran;DTXSID30294632;DDUCSZMYPQLRNL-UHFFFAOYSA-N;2,2-bishydroxymethyl tetrahydrofuran;NSC-97504;2,2-bis(hydroxymethyl)tetrahydrofuran;CS-0444829;(2-Hydroxymethyltetrahydrofuran-2-yl)methanol;EN300-2934156;Z1726051641

Chemical Property of [2-(Hydroxymethyl)oxolan-2-yl]methanol

Chemical Property:

• Vapor Pressure: 0.00289mmHg at 25°C
• Boiling Point: 253.1°Cat760mmHg
• Flash Point: 106.9°C
• Density: 1.145g/cm³
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 132.078644241
• Heavy Atom Count: 9
• Complexity: 88.3

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(OC1)(CO)CO

Technology Process of [2-(Hydroxymethyl)oxolan-2-yl]methanol

There total 5 articles about [2-(Hydroxymethyl)oxolan-2-yl]methanol 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: 97.0%

2,2-bis((tert-butyldimethylsilyloxy)methyl)tetrahydrofuran (898252-58-9) → 2,2-bis(hydroxymethyl)-tetrahydrofuran (13386-57-7)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 2.5h; cooling;

DOI:10.1021/ol0608350

Reference yield: 31.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + formic acid (64-18-6) → 2,2-bis(hydroxymethyl)-tetrahydrofuran (13386-57-7)

Guidance literature:

methyl tetrahydrofuran-2-carboxylate; With diisobutylaluminium hydride; In tetrahydrofuran; toluene; at -78 - -65 ℃; for 1.5h;

With methanol; In tetrahydrofuran; toluene; at -78 - 5 ℃;

formaldehyd; formic acid; With sodium hydroxide; water; In tetrahydrofuran; toluene; at 5 - 65 ℃;

Reference yield:

5-(tert-butyl-dimethyl-silanyloxy)-4-(tert-butyl-dimethyl-silanyloxymethyl)-pentane-1,4-diol → 2,2-bis(hydroxymethyl)-tetrahydrofuran (13386-57-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylamine; 4-(dimethylamino)pyridine; tosyl chloride / CH₂Cl₂ / 48 h / 20 °C

1.2: 83 percent / potassium hexamethyldisilazide / toluene / 1 h

2.1: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2.5 h

With dmap; tetrabutyl ammonium fluoride; triethylamine; p-toluenesulfonyl chloride; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo0708238

upstream raw materials:

2,2-bis((tert-butyldimethylsilyloxy)methyl)tetrahydrofuran

formaldehyd

formic acid

Downstream raw materials:

(S)-tetrahydro-2-((octadecyloxy)methyl)-2-<<<1(e)-allyl-2(e)-isopropyl-5(e)-methylcyclohexanyl>oxy>methyl>furan

(R)-tetrahydro-2-<<<1(e)-allyl-2(e)-isopropyl-5(e)-methylcyclohexanyl>oxy>methyl>-2-furanmethanol

(S)-tetrahydro-2-<<<1(e)-allyl-2(e)-isopropyl-5(e)-methylcyclohexanyl>oxy>methyl>-2-furanmethanol

Decyl-carbamic acid 2-hydroxymethyl-tetrahydro-furan-2-ylmethyl ester