3-Buten-1-ol

Base Information

• Chemical Name: 3-Buten-1-ol
• CAS No.: 627-27-0
• Deprecated CAS: 2382877-29-2
• Molecular Formula: C4H8O
• Molecular Weight: 72.1069
• Hs Code.: 29052990
• European Community (EC) Number: 210-991-3
• NSC Number: 60194
• UNII: 3DB2KRM1I9
• DSSTox Substance ID: DTXSID2060836
• Nikkaji Number: J134.573G,J2.040.003J
• Wikidata: Q27257071
• Metabolomics Workbench ID: 44820
• Mol file: 627-27-0.mol

Synonyms:3-Buten-1-ol;627-27-0;but-3-en-1-ol;Allylcarbinol;3-Butenyl alcohol;1-Buten-4-ol;Vinylethyl alcohol;3-Butene-1-OL;CH2=CHCH2CH2OH;BUTEN-(3)-O1-(L);3-Buten-1-O1;NSC 60194;UNII-3DB2KRM1I9;3DB2KRM1I9;EINECS 210-991-3;NSC-60194;AI3-30545;Homoallyl Alcohol;1-Hydroxy-3-butene;3-butenol;hydroxy-3-butene;3-butene-ol;3-buten-ol;MFCD00002959;3-Buten-1-ol, 96%;CH2=CH(CH2)2OH;DTXSID2060836;4-Hydroxybutane-1,2-diylradical;CHEBI:193941;AMY14291;BCP23015;NSC60194;AKOS000121865;AB00288;3-Buten-1-ol, purum, >=98.0% (GC);B0236;CS-0008447;FT-0615263;EN300-28907;P16638;Q27257071;F0001-1684

Chemical Property of 3-Buten-1-ol

Chemical Property:

• Appearance/Colour: Clear colorless liquid
• Vapor Pressure: 10.6mmHg at 25°C
• Melting Point: 193ºC
• Refractive Index: n20/D 1.421(lit.)
• Boiling Point: 113.5 °C at 760 mmHg
• PKA: 15.04±0.10(Predicted)
• Flash Point: 32.2 °C
• PSA: 20.23000
• Density: 0.827 g/cm³
• LogP: 0.55480
• Storage Temp.: Flammables area
• Water Solubility.: SOLUBLE
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 72.057514874
• Heavy Atom Count: 5
• Complexity: 24.8

Purity/Quality:

99.0%Min ^*data from raw suppliers

3-Buten-1-ol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 16-26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Alcohols and Polyols, Other
• Canonical SMILES: C=CCCO
• Description: 3-Buten-1-ol is an unsaturated alcohol with the structural formula CH2=CHCH2CH2OH. Research into the production of 1,3-butadiene from biomass-derived C4 alcohols, including 3-buten-1-ol, has gained attention as a sustainable alternative to petroleum-based feedstocks.
• Uses and Mechanism of Action: 3-Buten-1-ol serves as an important intermediate in the production of 1,3-butadiene from biomass-derived C4 alcohols. It is formed as an intermediate during the dehydration of 1,3-butanediol and subsequent dehydration reactions. Various catalysts, such as ceria and modified ZrO2 catalysts, have been investigated for the selective production of 3-buten-1-ol from 1,4-butanediol. These catalysts facilitate the dehydration reactions, leading to the formation of 3-buten-1-ol.
• Production Methods: 3-Buten-1-ol is primarily produced through the dehydration of 1,4-butanediol using catalysts such as ceria and modified ZrO2. The dehydration reactions typically occur at elevated temperatures in the vapor phase.
• References: [1] Comparative Kinetics of the 3-Buten-1-ol and 1-Butene Reactions with OH Radicals: A Density Functional Theory/RRKM Investigation; DOI 10.1021/jp512544x; [2] Vapor-phase catalytic dehydration of 1,4-butanediol to 3-buten-1-ol over modified ZrO2 catalysts; DOI 10.1016/j.apcata.2017.01.024; [3] Synthesis of 3-buten-1-ol from 1,4-butanediol over ZrO2 catalyst; DOI 10.1016/j.molcata.2005.08.017; [4] Dehydration of 1,4-butanediol into 3-buten-1-ol catalyzed by ceria; DOI 10.1016/j.catcom.2004.05.006

Technology Process of 3-Buten-1-ol

There total 121 articles about 3-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: 69.9%

Butane-1,4-diol (110-63-4) → tetrahydrofuran (109-99-9,24979-97-3,77392-70-2) + homoalylic alcohol (627-27-0) + (E/Z)-2-buten-1-ol (6117-91-5,542-72-3)

Guidance literature:

With hydrogen; at 350 ℃; for 0.6h; Reagent/catalyst; Flow reactor;

DOI:10.1016/j.apcata.2017.01.024

Reference yield:

C10H11NO3S (130436-11-2) → formaldehyd (50-00-0,30525-89-4,61233-19-0) + homoalylic alcohol (627-27-0) + 1,5-Hexadien (592-42-7) + 3-butenal (7319-38-2) + di(p-nitrophenyl) disulfide (100-32-3) + allyl 4-nitrophenyl sulfide (32894-70-5)

Guidance literature:

In benzene; Product distribution; Irradiation;

DOI:10.1021/jo00310a008

Reference yield:

(4-Hydroxy-butyl)-trimethyl-ammonium; hydroxide (58390-09-3) → tetrahydrofuran (109-99-9,24979-97-3,77392-70-2) + homoalylic alcohol (627-27-0) + methoxy-1 butene-3 (4696-30-4) + 4-dimethylamino-1-butanol (13330-96-6) + dimethylamino-1 methoxy-4 butane (33962-95-7)

Guidance literature:

at 110 - 120 ℃; Product distribution;

upstream raw materials:

oxirane

tetrahydrofuran

vinyl magnesium bromide

vinylmagnesium chloride

Downstream raw materials:

2-phenyltetrahydro-2H-pyran-4-ol

(2S,4S)-4-hydroxy-2-methyltetrahydropyran

1,1-Di-(3-butenoxy)-methan

phenyl di(but-3-en-1-yl) phosphate

Refernces

• 1、 Matsuda, Asami,Matsumura, Yoshitaka,Sato, Satoshi,Yamada, Yasuhiro. "Vapor-phase dehydration of 1,4-butanediol to 1,3-butadiene over Y2Zr2O7 catalyst". . . Retrieved 2021/09/16.
• 2、 Faria, Jimmy,Komarneni, Mallik R.,Li, Gengnan,Pham, Tu,Resasco, Daniel E.,Ruiz, Maria P.,Santhanaraj, Daniel. "Synthesis of α,β- and β-Unsaturated Acids and Hydroxy Acids by Tandem Oxidation, Epoxidation, and Hydrolysis/Hydrogenation of Bioethanol Derivatives". supporting information. p. 7456 - 7460. Retrieved 2020/03/23.