(S)-3-Butene-1,2-diol

Base Information

• Chemical Name: (S)-3-Butene-1,2-diol
• CAS No.: 62214-39-5
• Molecular Formula: C4H8O2
• Molecular Weight: 88.1063
• European Community (EC) Number: 634-713-9
• UNII: N4142M4L8H
• DSSTox Substance ID: DTXSID201016476
• Nikkaji Number: J1.198.165H
• Wikidata: Q27284526
• Mol file: 62214-39-5.mol

Synonyms:(S)-3-Butene-1,2-diol;62214-39-5;(S)-But-3-ene-1,2-diol;(2S)-but-3-ene-1,2-diol;(2s)-3-butene-1,2-diol;3-Butene-1,2-diol, (S)-;N4142M4L8H;3-Butene-1,2-diol, (2S)-;UNII-N4142M4L8H;DTXSID201016476;MFCD00145261;CS-0170861;A23734;(S)-3-Butene-1,2-diol, >=97.0% (GC);Q27284526

Chemical Property of (S)-3-Butene-1,2-diol

Chemical Property:

• Vapor Pressure: 0.102mmHg at 25°C
• Refractive Index: n20/D 1.462
• Boiling Point: 196.5 °C at 760 mmHg
• PKA: 13.68±0.20(Predicted)
• Flash Point: 89.3 °C
• PSA: 40.46000
• Density: 1.053g/cm³
• LogP: -0.47440
• Storage Temp.: 2-8°C
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 88.052429494
• Heavy Atom Count: 6
• Complexity: 42.8

Purity/Quality:

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

(S)-3-Butene-1,2-diol ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn,Xi
• Statements: 36/37/38
• Safety Statements: 36-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=CC(CO)O
• Isomeric SMILES: C=C[C@@H](CO)O

Technology Process of (S)-3-Butene-1,2-diol

There total 17 articles about (S)-3-Butene-1,2-diol 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)-4-vinyl-1,3-dioxolan-2-one (205673-79-6) → (2S)-but-3-ene-1,2-diol (62214-39-5,86161-40-2)

Guidance literature:

With potassium carbonate; In methanol; at 60 ℃; for 2.5h; Inert atmosphere; Schlenk technique;

DOI:10.1002/jhet.2726

Reference yield: 65.0%

(S)-(+)-1,2-di-O-acetyl-3-butene-1,2-diol (233670-06-9) → (2S)-but-3-ene-1,2-diol (62214-39-5,86161-40-2)

Guidance literature:

With water; potassium carbonate; In methanol; for 1h;

DOI:10.1002/(SICI)1099-0690(199907)1999:7<1671::AID-EJOC1671>3.0.CO;2-Z

Reference yield: 46.0%

epoxybutene (930-22-3,62249-81-4) → (2S)-but-3-ene-1,2-diol (62214-39-5,86161-40-2) + (R)-2-vinyloxirane (930-22-3,62249-81-4) + (S)-(+)-3,4-epoxy-1-butene (62249-80-3,62249-81-4)

Guidance literature:

With chiral oligo-(salen)Co(OTs) complexes; lutidinium p-toluene sulfonate; water; In dichloromethane; acetonitrile; at 20 ℃; for 4h;

DOI:10.1021/ja005867b

upstream raw materials:

(S)-1,2-O-isopropylidene-but-3-ene-1,2-diol

(S)-(+)-3,4-epoxy-1-butene

3,4-butenediol

(2S)-1,2-O-cyclohexylidenebut-3-ene-1,2-diol

Downstream raw materials:

(S)-1-(benzyloxy)but-3-en-2-ol

(S)-1-(triphenylmethoxy)-3-buten-2-ol

1,2-dihydroxybutane

(2S)-1-O-(4,4'-dimethoxytrityl)but-3-ene-1,2-diol

Refernces

• 1、 Boaz, Neil W.,Falling, Stephen N.,Moore, Mary K.. "The preparation of enantiomerically pure 3,4-epoxy-1-butene and 3-butene-1,2-diol". . p. 1615 - 1617. Retrieved 2005.
• 2、 Alkattan, Mohammed,Prunet, Jo?lle,Shaver, Michael P.. "Functionalizable Stereocontrolled Cyclopolyethers by Ring-Closing Metathesis as Natural Polymer Mimics". supporting information. p. 12835 - 12839. Retrieved 2018/09/25.
• 3、 Chatterjee, Bhaskar,Mondal, Dhananjoy,Bera, Smritilekha. "Asymmetric synthesis of a 12-membered macrolactone core and a 6-epi analogue of amphidinolide W from 4-pentenoic acid". . p. 1170 - 1185,16. Retrieved 2020/09/09.