(r)-Butane-1,2,4-triol

Base Information

• Chemical Name: (r)-Butane-1,2,4-triol
• CAS No.: 70005-88-8
• Molecular Formula: C4H10O3
• Molecular Weight: 106.122
• European Community (EC) Number: 626-148-1
• UNII: H270PVK464
• DSSTox Substance ID: DTXSID10426378
• Nikkaji Number: J181.756F
• Wikidata: Q27279543
• Mol file: 70005-88-8.mol

Synonyms:(r)-butane-1,2,4-triol;70005-88-8;(R)-(+)-1,2,4-Butanetriol;(2R)-butane-1,2,4-triol;(2R)-1,2,4-Butanetriol;1,2,4-Butanetriol, (2R)-;(R)-1,2,4-Butanetriol;(+)-1,2,4-butanetriol;1,2,4-Butanetriol, (R)-;R-(-)-1,2,4-Butanetriol;(R)-(+)-1,2,4-Triydroxybutane;UNII-H270PVK464;H270PVK464;MFCD00063212;BGQ;SCHEMBL709962;DTXSID10426378;ARXKVVRQIIOZGF-SCSAIBSYSA-N;[R,(+)]-1,2,4-Butanetriol;(r)-(+)-1,2,4-trihydroxybutane;AKOS016015974;AC-13918;AS-36943;(R)-(+)-1,2,4-Butanetriol, 98%;CS-0069613;A836731;Q27279543

Chemical Property of (r)-Butane-1,2,4-triol

Chemical Property:

• Refractive Index: n20/D 1.474
• Boiling Point: 303.9 °C at 760 mmHg
• PKA: 14.02±0.20(Predicted)
• Flash Point: 153.9 °C
• PSA: 60.69000
• Density: 1.213 g/cm³
• LogP: -1.27800
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Methanol (Sparingly), Water (Slightly)
• XLogP3: -1.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 106.062994177
• Heavy Atom Count: 7
• Complexity: 37.9

Purity/Quality:

98%,99%, ^*data from raw suppliers

(R)?-?(+?)?-?1,?2,?4-?Butanetriol ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(CO)C(CO)O
• Isomeric SMILES: C(CO)[C@H](CO)O
• Uses: (R)?-?(+?)?-?1,?2,?4-?Butanetriol is a reagent used in organic synthesis including the preparation of the steroid hormone 1α,?25-?dihydroxyvitamin D3 which is the most active metabolite of vitamin D3 exerting control over a plethora of biological processes. (R)-(+)-1,2,4-Butanetriol can be used as a reactant to prepare: Phenanthrene 9, 10 diacetal from phenanthrene 9, 10 quinone. (R)-1,2,4-Tris(benzoyloxy)butane by reacting with benzyl chloride in the presence of a base and DMAP.

Technology Process of (r)-Butane-1,2,4-triol

There total 26 articles about (r)-Butane-1,2,4-triol 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%

D-Malic acid (636-61-3,78644-42-5) → (R)-1,2,4-butanetriol (70005-88-8,6810-31-7)

Guidance literature:

With Trimethyl borate; dimethylsulfide borane complex; In tetrahydrofuran; Inert atmosphere;

DOI:10.1016/j.tet.2011.05.020

Reference yield: 99.0%

2-((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)ethanol (5754-34-7,32233-43-5,35396-36-2,70005-89-9) → (R)-1,2,4-butanetriol (70005-88-8,6810-31-7)

Guidance literature:

With indium(III) triflate; In tetrahydrofuran; water; at 100 ℃; for 0.0833333h; Microwave irradiation;

DOI:10.1016/j.tetlet.2010.05.116

Reference yield: 97.0%

(R)-1-O-benzyl-1,2,4-butanetriol (81096-93-7) → (R)-1,2,4-butanetriol (70005-88-8,6810-31-7)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; under 750.075 Torr;

DOI:10.1002/adsc.200900707

upstream raw materials:

(R)-dimethyl malate

2-(2-Tetrahydropyranyloxy)-1,4-butanediol

D-Malic acid

D,L-1,2,4-butanetriol

Downstream raw materials:

C₁₈H₂₀O₅S

(2R,4R)-2-phenyl-4-(tosyloxy)methyl-1,3-dioxane

(R)-1-O-benzyl-1,2,4-butanetriol

(-)-cis-4-hydroxymethyl-2-phenyl-1,3-dioxolane

Refernces

• 1、 Roushanbakhti, Ahria,Liu, Yifan,Winship, Paul C. M.,Tucker, Michael J.,Akhtar, Wasim M.,Walter, Daryl S.,Wrigley, Gail,Donohoe, Timothy J.. "Cobalt versus Osmium: Control of Both trans and cis Selectivity in Construction of the EFG Rings of Pectenotoxin 4". supporting information. p. 14883 - 14887. Retrieved 2017/10/24.
• 2、 Leahy, James W.,Brzezinski, Linda Joy. "A synthetic approach to the phorboxazoles—synthesis of the exocyclic fragment". . p. 4670 - 4672. Retrieved 2016/09/28.