(S)-1,2,4-Butanetriol

Base Information

• Chemical Name: (S)-1,2,4-Butanetriol
• CAS No.: 42890-76-6
• Molecular Formula: C4H10O3
• Molecular Weight: 106.122
• Hs Code.: 2905499000
• European Community (EC) Number: 610-080-4
• UNII: 03V2R7Y196
• Nikkaji Number: J181.757D
• Wikidata: Q27247589
• Mol file: 42890-76-6.mol

Synonyms:42890-76-6;(S)-(-)-1,2,4-Butanetriol;(S)-Butane-1,2,4-triol;(S)-1,2,4-Butanetriol;(2S)-butane-1,2,4-triol;(-)-1,2,4-Butanetriol;1,2,4-Butanetriol, (S)-;1,2,4-Butanetriol, (2S)-;(-)-(S)-1,2,4-Butanetriol;UNII-03V2R7Y196;03V2R7Y196;(2~{S})-butane-1,2,4-triol;MFCD00063213;(s)-(-)-butane-1,2,4-triol;(S)-1,2,4-butanentriol;(2s)-1,2,4-butanetriol;SCHEMBL705919;CHEBI:140438;(A+/-)-butane-1,2,4-triol;AMY14876;(2S)-(-)-Butane-1,2,4-triol;AKOS015901225;Butanetriol 1000 microg/mL in Pyridine;AC-13895;AS-36942;(S)-(-)-1,2,4-Butanetriol, 98%;B2404;CS-0000034;EN300-761227;A826053;Q27247589;(S)-(-)-1,2,4-BUTANETRIOL;(S)-(-)-1,2,4-Butanetriol, purum, >=95.0% (sum of enantiomers, GC);0V1

Chemical Property of (S)-1,2,4-Butanetriol

Chemical Property:

• Refractive Index: n20/D 1.475(lit.)
• 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.: 2-8°C
• Sensitive.: Hygroscopic
• Solubility.: Chloroform (Slightly), Methanol (Sparingly), Water (Slightly)
• Water Solubility.: soluble
• 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:

99.9% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s): F,Xn
• Hazard Codes: F,Xn
• Statements: 36/37/38-41-20/21/22-11
• Safety Statements: 23-24/25-39-26-16-36/37-28-33-29-9

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(CO)C(CO)O
• Isomeric SMILES: C(CO)[C@@H](CO)O
• Description: (S)-(-)-1,2,4-Butanetriol can be prepared via reduction of (S)-malic acid in the presence of borane-dimethyl sulfide. (S)-(-)-1,2,4-Butanetriol may be used as a starting material in the enantioselective total syntheses of (+)-azimine and (+)-carpaine.?It can also be used to prepare the organic building blocks?(+)-3,4-epoxy-1-butanol,?(2S,4S)-4-(hydroxymethyl)-2-ferrocenyl-1,3-dioxan,?(S)-1,2,4-triacetoxybutane via acetylation with acetic anhydride,?and (S)-1,2,4-tris-(3,5-dinitrobenzoy1oxy)butane via esterification with 3,5-dinitrobenzoyl chloride, and so on.
• Uses: Glycerophospholipids act as regulators of various enzyme activities, and can be used as biological markers to indicate pathological states.

Technology Process of (S)-1,2,4-Butanetriol

There total 34 articles about (S)-1,2,4-Butanetriol 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%

(S)-Malic acid (97-67-6,78644-42-5) → (S)-1,2,4-butanetriol (42890-76-6,6810-31-7)

Guidance literature:

With Trimethyl borate; dimethylsulfide borane complex; In tetrahydrofuran; at -5 ℃; for 51h;

DOI:10.1021/ja00164a024

Reference yield: 100.0%

dimethyl (S)-malate (617-55-0) → (S)-1,2,4-butanetriol (42890-76-6,6810-31-7)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 65 ℃; for 72h;

DOI:10.1016/S0040-4020(01)88223-5

Reference yield: 98.3%

(S)-1,4-dibenzyloxy-2-butanol (114818-97-2) → (S)-1,2,4-butanetriol (42890-76-6,6810-31-7)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethanol; at 60 ℃; for 30h; under 18751.9 Torr; Pressure; Autoclave;

upstream raw materials:

(S)-Malic acid

(2S,2'RS) 2-O-(Tetrahydro-2'-pyranyl)-1,2,4-butanetriol

dimethyl (S)-malate

Diethyl (S)-malate

Downstream raw materials:

(S)-1,4-bis-trityloxy-butan-2-ol

(2S)-1,2,4-butanetriol

(2S,4S)-4-hydroxymethyl-2-(p-methoxymethyl)-1,3-dioxane

(2S)-1,2,4-trimethanesulfonyloxybutane

Refernces

• 1、 Tandon, Vishnu K.,Leusen, Albert M. van,Wynberg, Hans. "Synthesis of Enantiomerically Pure (S)-(+)-3-Hydroxytetrahydrofuran and Its R Enantiomer from Malic or Tartaric Acid". . p. 2767 - 2769. Retrieved 1983.
• 2、 Wroblewski,Applequist,Takaya,Honzatko,Kim,Jacobson,Reitsma,Yeung,Verkade. "EXPERIMENTAL AND THEORETICAL STUDY OF THE STRUCTURES AND OPTICAL ROTATIONS OF CHIRAL BICYCLIC ORTHO ESTERS.". . p. 4144 - 4150. Retrieved 1988.
• 3、 Akimitsu, Kazuya,Guo, Yian,Hashimoto, Masaru,Kotani, Akari,Minami, Atsushi,Mochizuki, Susumu,Oikawa, Hideaki,Ozaki, Taro,Peng, Wenquan,Takino, Junya,Ye, Tao,Yu, Jie. "Biochemistry-Guided Prediction of the Absolute Configuration of Fungal Reduced Polyketides". supporting information. p. 23403 - 23411. Retrieved 2021/09/18.
• 4、 -. "Preparation method of (S)-1, 2, 4-butantriol[7]". Paragraph 0034; 0040-0043; 0049-0050. . Retrieved 2020/05/05.