3-Methyl-2-buten-1-OL

Base Information

• Chemical Name: 3-Methyl-2-buten-1-OL
• CAS No.: 556-82-1
• Deprecated CAS: 135146-66-6
• Molecular Formula: C5H10O
• Molecular Weight: 86.1338
• Hs Code.: 29052990
• European Community (EC) Number: 209-141-4
• ICSC Number: 1760
• NSC Number: 158709
• UN Number: 1987
• UNII: 55MY0HM445
• DSSTox Substance ID: DTXSID2027206
• Nikkaji Number: J11.528B
• Wikipedia: Prenol
• Wikidata: Q425512
• Metabolomics Workbench ID: 3196
• ChEMBL ID: CHEMBL3184952
• Mol file: 556-82-1.mol

Synonyms:3-methyl-2-buten-1-ol;3-methylbut-2-en-1-ol;prenol

Chemical Property of 3-Methyl-2-buten-1-OL

Chemical Property:

• Appearance/Colour: colorless liquid with fruity odor
• Vapor Pressure: 1.4 mm Hg ( 20 °C)
• Melting Point: -86oC
• Refractive Index: n20/D 1.443(lit.)
• Boiling Point: 141.5 °C at 760 mmHg
• PKA: 14.83±0.10(Predicted)
• Flash Point: 43.3 °C
• PSA: 20.23000
• Density: 0.844 g/cm³
• LogP: 0.94490
• Storage Temp.: Flammables area
• Solubility.: 64g/l
• Water Solubility.: 170 g/L (20 ºC)
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 86.073164938
• Heavy Atom Count: 6
• Complexity: 51

Purity/Quality:

99% ^*data from raw suppliers

3-Methyl-2-buten-1-ol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 10-22-36/37/38-38-21/22
• Safety Statements: 26-36-37-23-16

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Alcohols and Polyols, Other
• Canonical SMILES: CC(=CCO)C
• Inhalation Risk: No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
• Effects of Short Term Exposure: The substance is severely irritating to the skin and eyes.
• Description: 3-Methyl-2-buten-l-ol has a phenolic, metallic odor bearing a resemblance to iron gallate ink. May be synthesized from isoprene by hydration via prenyl acetate or by rearrangement of 3-methyll-buten-3-ol.
• Uses: 3-Methyl-2-buten-1-ol is used as a reagent for protection of carboxylic acids as their 3-methyl-2-buten-1-yl (Prenyl) esters. It is also used in perfumery. 3-Methyl-2-buten-1-ol was used as starting reagent during asymmetric total syntheses of (R)-(+)- and (S)-(-)-umbelactone via Sharpless asymmetric epoxidation reaction.

Technology Process of 3-Methyl-2-buten-1-OL

There total 94 articles about 3-Methyl-2-buten-1-OL 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: 99.0%

3,3-dimethyl acrylaldehyde (107-86-8) → 3-methyl-2-buten-1-ol (556-82-1)

Guidance literature:

With acetylacetonatodicarbonylrhodium(l); trifluorormethanesulfonic acid; carbon monoxide; N-(5-diphenylphosphanylpyrrole-2-carbonyl)guanidine; hydrogen; In dichloromethane; at 40 ℃; for 20h; under 15001.5 Torr; Autoclave;

DOI:10.1002/anie.200903620

Reference yield: 97.0%

2-methyl-1-buten-4-ol (763-32-6) → 3-methyl-2-buten-1-ol (556-82-1)

Guidance literature:

With lithium hexafluorophosphate; at 0 ℃; for 8h; Reagent/catalyst; Temperature; Irradiation; Inert atmosphere;

Reference yield: 95.0%

prenyl bromide (870-63-3) → 3-methyl-2-buten-1-ol (556-82-1)

Guidance literature:

With Amberlyst A 26; carbonate form; In tetrahydrofuran; for 1h; Heating;

DOI:10.1055/s-1981-29597

upstream raw materials:

2-methyl-1-buten-4-ol

sodium acetate

dichloro-acetic acid

2-methyl-3-buten-2-ol

Downstream raw materials:

6-methyl-3,5-heptadien-2-one

2-methyl-3-buten-2-ol

formiate de methyl-3 butene-2 ol-1

formiate de methyl-2 butene-3 ol-2

Refernces

• 1、 Miller et al.. "". . p. 1683. Retrieved 1971.
• 2、 Chen, Manyu,Cui, Kai,Hou, Zhenshan,Peng, Qingpo,Wang, Jiajia,Wei, Xinjia,Zhao, Xiuge. "Cationic Ru complexes anchored on POM via non-covalent interaction towards efficient transfer hydrogenation catalysis". . . Retrieved 2021/12/22.
• 3、 Chen, Yurong,Li, Guangqin,Li, Yinle,Liu, Qian,Liu, Qinghua,Liu, Qinglin,Su, Hui. "Ir nanoclusters confined within hollow MIL-101(Fe) for selective hydrogenation of α,β-unsaturated aldehyde". supporting information. . Retrieved 2021/08/13.