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1,2-Epoxybutane (also known as 1,2-butene oxide) is an epoxide that participates in regioselective ring-opening reactions, particularly when promoted by Lewis acids like TiCl4 or Grignard reagents. These reactions typically target the less hindered carbon of the epoxide ring, enabling the synthesis of functionalized phosphonates, such as γ-hydroxy-α,α-difluoromethylenephosphonates. Its reactivity makes it a valuable intermediate for producing biologically relevant phosphate ester analogues and enzyme substrates.

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  • 106-88-7 Structure
  • Basic information

    1. Product Name: 1,2-EPOXYBUTANE
    2. Synonyms: (R,S)-2-Ethyl-oxirane;1,2-Butene oxide;1,2-buteneoxide;1,2-butyleneepoxide;1,2-butyleneoxide,stabilized;1,2-epoxy;1,2-epoxy-butan;1,2-epoxybutane(1,2-butyleneoxide)
    3. CAS NO:106-88-7
    4. Molecular Formula: C4H8O
    5. Molecular Weight: 72.10572
    6. EINECS: 203-438-2
    7. Product Categories: Industrial/Fine Chemicals;Organics;Oxiranes;Simple 3-Membered Ring Compounds
    8. Mol File: 106-88-7.mol
  • Chemical Properties

    1. Melting Point: -129.28°C
    2. Boiling Point: 63 °C(lit.)
    3. Flash Point: 10 °F
    4. Appearance: colourless liquid with an unpleasant smell
    5. Density: 0.829 g/mL at 20 °C(lit.)
    6. Vapor Density: 2.2 (vs air)
    7. Vapor Pressure: 140 mm Hg ( 20 °C)
    8. Refractive Index: n20/D 1.384
    9. Storage Temp.: Store below +30°C.
    10. Solubility: 86.8g/l
    11. Explosive Limit: 1.7-19%(V)
    12. Water Solubility: 86.8g/L at 25℃
    13. Stability: Stable, but prone to polymerization - stabilizer may be added to neat liquid. Highly flammable. Incompatible with strong oxidizi
    14. BRN: 102411
    15. CAS DataBase Reference: 1,2-EPOXYBUTANE(CAS DataBase Reference)
    16. NIST Chemistry Reference: 1,2-EPOXYBUTANE(106-88-7)
    17. EPA Substance Registry System: 1,2-EPOXYBUTANE(106-88-7)
  • Safety Data

    1. Hazard Codes: F,Xn
    2. Statements: 11-20/21/22-36/37/38-40-52/53
    3. Safety Statements: 9-16-29-36/37-61-19
    4. RIDADR: UN 3022 3/PG 2
    5. WGK Germany: 2
    6. RTECS: EK3675000
    7. TSCA: Yes
    8. HazardClass: 3.1
    9. PackingGroup: II
    10. Hazardous Substances Data: 106-88-7(Hazardous Substances Data)

106-88-7 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 106-88-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 6 respectively; the second part has 2 digits, 8 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 106-88:
(5*1)+(4*0)+(3*6)+(2*8)+(1*8)=47
47 % 10 = 7
So 106-88-7 is a valid CAS Registry Number.
InChI:InChI=1/C4H8O/c1-2-4-3-5-4/h4H,2-3H2,1H3/t4-/m1/s1

106-88-7 Well-known Company Product Price

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  • Aldrich

  • (109975)  1,2-Epoxybutane  99%

  • 106-88-7

  • 109975-250ML

  • 596.70CNY

  • Detail
  • Aldrich

  • (109975)  1,2-Epoxybutane  99%

  • 106-88-7

  • 109975-1L

  • 916.11CNY

  • Detail

106-88-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 1,2-Epoxybutane

1.2 Other means of identification

Product number -
Other names Ethylethylene Oxide

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. The primary use of 1,2-epoxybutane is as a stabilizer in chlorinated hydrocarbon solvents. 1,2-Epoxybutane is used in the production of the corresponding butylene glycols and their derivatives. It is also used to make butanolamines, surface-active agents, and gasoline additives.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:106-88-7 SDS

106-88-7Synthetic route

1-butylene
106-98-9

1-butylene

Cumene hydroperoxide
80-15-9

Cumene hydroperoxide

A

ethyloxirane
106-88-7

ethyloxirane

B

1-methyl-1-phenylethyl alcohol
617-94-7

1-methyl-1-phenylethyl alcohol

Conditions
ConditionsYield
With Ti-HMS at 95℃; under 26252.6 Torr;A 98.6%
B n/a
1-butylene
106-98-9

1-butylene

ethyloxirane
106-88-7

ethyloxirane

Conditions
ConditionsYield
With phosphotungstic acid; phosphoric acid tributyl ester; dihydrogen peroxide In toluene at 70℃; under 3750.38 Torr; for 5h; Temperature; Pressure;96.8%
With tert.-butylhydroperoxide; 2C13H10N3O2(1-)*MoO2(2+) In methanol; dichloromethane for 1h; Catalytic behavior; Reagent/catalyst;91%
With dihydrogen peroxide; teterabutylammonium In acetonitrile at 31.85℃; for 8h;88%
1-chloro-butan-2-ol
1873-25-2

1-chloro-butan-2-ol

ethyloxirane
106-88-7

ethyloxirane

Conditions
ConditionsYield
With Ph4SbOMe In dichloromethane at 40℃; for 3h;64%
With potassium hydroxide
With Ph4SbOMe In dichloromethane at 40℃; for 4h;75 % Chromat.
2-chloro-1-butanol
26106-95-6

2-chloro-1-butanol

ethyloxirane
106-88-7

ethyloxirane

Conditions
ConditionsYield
With Ph4SbOMe In dichloromethane at 40℃; for 3h;10%
1-butylene
106-98-9

1-butylene

A

ethyloxirane
106-88-7

ethyloxirane

B

1-Hydroxy-2-butanone
5077-67-8

1-Hydroxy-2-butanone

Conditions
ConditionsYield
With oxygen at 500℃; under 5148.6 Torr;
1-bromo-2-butanol
2482-57-7

1-bromo-2-butanol

ethyloxirane
106-88-7

ethyloxirane

Conditions
ConditionsYield
With potassium hydroxide
1-butylene
106-98-9

1-butylene

acetylperoxy radical
36709-10-1

acetylperoxy radical

ethyloxirane
106-88-7

ethyloxirane

Conditions
ConditionsYield
at 83.4 - 137℃; Kinetics; further compounds;
epoxybutene
930-22-3

epoxybutene

A

ethyloxirane
106-88-7

ethyloxirane

B

homoalylic alcohol
627-27-0

homoalylic alcohol

C

(E/Z)-2-buten-1-ol
6117-91-5

(E/Z)-2-buten-1-ol

D

butyraldehyde
123-72-8

butyraldehyde

E

crotonaldehyde
123-73-9

crotonaldehyde

F

butan-1-ol
71-36-3

butan-1-ol

Conditions
ConditionsYield
With hydrogen; at 30℃; under 760 Torr; for 8h; Product distribution; Mechanism; catalytic hydrogenation of the title compound in the presence of various catalysts (cationic rhodium complexes); influence of the type of catalyst's ligand, reaction time and pressure on the activity of catalysts;A 2.1 % Chromat.
B 16.5 % Chromat.
C 11.7 % Chromat.
D 4.4 % Chromat.
E 44.3 % Chromat.
F 1.7 % Chromat.
With hydrogen at 80℃; under 16274.9 Torr; Autoclave;
2-bromo-1-butanol
24068-63-1

2-bromo-1-butanol

ethyloxirane
106-88-7

ethyloxirane

Conditions
ConditionsYield
With potassium carbonate In 1,4-dioxane at 25℃; for 120h; Yield given;
allyl t-butyl peroxide
39972-78-6

allyl t-butyl peroxide

ethyloxirane
106-88-7

ethyloxirane

Conditions
ConditionsYield
With tert-butyl peroxyacetate at 110℃; under 0.001 Torr; for 12h;
epoxybutene
930-22-3

epoxybutene

A

ethyloxirane
106-88-7

ethyloxirane

B

trans-Crotonaldehyde
123-73-9

trans-Crotonaldehyde

C

methyl propyl ether
557-17-5

methyl propyl ether

D

methylallylether
627-40-7

methylallylether

E

butyraldehyde
123-72-8

butyraldehyde

F

n-butane
106-97-8

n-butane

Conditions
ConditionsYield
With hydrogen; silica gel; palladium at -0.15℃; under 150.012 Torr; Product distribution; Mechanism; also ethyloxirane; also with duterium; also over Pt-SiO2; var. temp. and time;
1-butylene
106-98-9

1-butylene

oxygen

oxygen

A

ethyloxirane
106-88-7

ethyloxirane

B

1-Hydroxy-2-butanone
5077-67-8

1-Hydroxy-2-butanone

Conditions
ConditionsYield
at 340 - 510℃; under 5148.6 Torr;
1-butylene
106-98-9

1-butylene

atomic oxygen

atomic oxygen

A

ethyloxirane
106-88-7

ethyloxirane

B

butyraldehyde
123-72-8

butyraldehyde

C

butanone
78-93-3

butanone

n-butane
106-97-8

n-butane

A

ethyloxirane
106-88-7

ethyloxirane

C

nitromethane
75-52-5

nitromethane

D

ethanol
64-17-5

ethanol

E

butanone
78-93-3

butanone

F

iso-butanol
78-92-2, 15892-23-6

iso-butanol

G

CO, CO2

CO, CO2

Conditions
ConditionsYield
With oxygen; dimethyl amine at 291℃; under 123 Torr; Product distribution; study of the oxidation of butane in the presence of primary and secondary amines; variation of pressure and time; mechanism for the formation of nitromethane is proposed;
buta-1,3-diene
106-99-0

buta-1,3-diene

ethyloxirane
106-88-7

ethyloxirane

Conditions
ConditionsYield
0.1% gold/titanium/silicon catalyst Product distribution / selectivity;
epoxybutene
930-22-3

epoxybutene

A

ethyloxirane
106-88-7

ethyloxirane

B

homoalylic alcohol
627-27-0

homoalylic alcohol

C

(E/Z)-2-buten-1-ol
6117-91-5

(E/Z)-2-buten-1-ol

D

crotonaldehyde
123-73-9

crotonaldehyde

Conditions
ConditionsYield
With hydrogen; Ag-Pt/SiO2 Kinetics; Product distribution; Further Variations:; Catalysts; effect of Ag addition;
1-butylene
106-98-9

1-butylene

1-hexene
592-41-6

1-hexene

A

ethyloxirane
106-88-7

ethyloxirane

B

1,2-Epoxyhexane
1436-34-6

1,2-Epoxyhexane

Conditions
ConditionsYield
With dihydrogen peroxide In water; acetonitrile at 59.84℃; under 1824.12 Torr; for 12h;A 72 %Chromat.
B 27 %Chromat.
1,2-Epoxydecane
2404-44-6

1,2-Epoxydecane

C6H14OS
872313-01-4

C6H14OS

A

ethyloxirane
106-88-7

ethyloxirane

B

2-hydroxybutyl n-octyl sulfide
100392-70-9

2-hydroxybutyl n-octyl sulfide

Conditions
ConditionsYield
In chlorobenzene Kinetics;
styrene oxide
96-09-3

styrene oxide

C6H14OS
872313-01-4

C6H14OS

A

ethyloxirane
106-88-7

ethyloxirane

B

(±)-1-(phenylthio)butan-2-ol
67210-33-7, 67210-38-2, 136656-75-2, 79345-23-6

(±)-1-(phenylthio)butan-2-ol

Conditions
ConditionsYield
In chlorobenzene Kinetics;

106-88-7Related news

Polymer paperPhotopolymerization of 1,2-epoxypropane and 1,2-EPOXYBUTANE (cas 106-88-7) by arenediazonium salts: evidence for anion dependence of the extent of polymerization08/26/2019

The rates and extents of polymerization of 1,2-epoxypropane and 1,2-epoxybutane, induced by photolysis of dilute concentrations of salts of 2,5-diethoxy-4-tolylthiobenzenediazonium ion with various Lewis acids (SbF−6, PF−6, BF−4 etc.) have been determined by viscosity, 1H n.m.r. and polymer isol...detailed

Excess molar enthalpies of eight binary mixtures containing 1,2-EPOXYBUTANE (cas 106-88-7) + ethyl alkanoates at 298.15 K08/22/2019

Excess molar enthalpies, HEm, have been measured using a flow microcalorimeter at 298.15 K and at atmospheric pressure for the eight mixtures containing 1,2-epoxybutane with ethyl acetate, ethyl propanoate, ethyl butyrate, ethyl pentanoate, ethyl hexanoate, ethyl heptanoate, ethyl octanoate and ...detailed

Isomerization and hydrogenolysis of 1,2-EPOXYBUTANE (cas 106-88-7) on platinum08/20/2019

The transformation of 1,2-epoxybutane on PtCandPtCr2O3 catalysts in the presence of hydrogen has been studied in a flow apparatus at atmospheric pressure and in the temperature range 160–190 °C. Parallel formation of butanal, 2-butanone, 1-butanol, and 2-butanol has been observed. The selectiv...detailed

PaperStereospecific formation of 1,2-epoxypropane, 1,2-EPOXYBUTANE (cas 106-88-7) and 1-chloro-2,3-epoxypropane by alkene-utilizing bacteria08/18/2019

Resting cells of ethene grown Mycobacterium 2W produced 1,2-epoxypropane stereospecifically from propene as revealed by optical rotation, 1H n.m.r. using a chiral shift reagent, and also by complexation gas chromatography involving a glass capillary column coated with an optically active metal c...detailed

106-88-7Relevant articles and documents

Epoxidation of olefins at low temperature using m-chloroperbenzoic acid

Srinivasan,Chandrasekharam,Vani,Chida, A. Seema,Singh

, p. 1853 - 1858 (2002)

Epoxidation of olefins using m-chloroperbenzoic acid in dichloromethane without catalyst at low temperature is described.

Transformation of vinyloxirane on Pt-SiO2 and Pd-SiO2

Bartok, Mihaly,Fasi, Andras,Notheisz, Ferenc

, p. 40 - 47 (1998)

The transformation of vinyloxirane and ethyloxirane were studied on Pt-SiO2 and Pd-SiO2 catalysts at 273 and 301 K in a recirculation reactor, in the presence of hydrogen or deuterium. There are significant differences, not only in reaction rates, but also in reaction routes, depending upon the nature of the metal. The main reaction routes are: deoxygenation and hydrogen or deuterium addition on Pt-SiO2; isomerization and hydrogenolysis on Pd-SiO2. The reaction routes leading to the formation of the individual products are interpreted on the basis of the experimental results. In the case of the hydrogenolysis of oxiranes, Pd was shown to exhibit a special reactivity, unlike earlier observations described in the literature.

Synthesis, crystal structure, and catalytic property of a vanadium(V) complex with mixed ligands

Shen,Zhang,Shao,Lian,Liu

, p. 372 - 375 (2015)

With a tridentate hydrazone ligand N′-(3-bromo-2-hydroxybenzylidene)-2-methylbenzohy-drazide (H2L) and a bidentate ligand benzohydroxamic acid (HL′) with VO(Acac)2, a mononuclear vanadium(V) complex was prepared and characterized by elemental analysis, IR spectroscopy and X-ray structure determination (CIF file CCDC no. 1029909). The complex crystallizes in the monoclinic space group C2/c with unit cell dimensions a = 27.870(2), b = 11.4893(5), c = 18.467(2) ?, β = 131.444(1)°, V = 4432.6(6) ?3, Z = 8, R 1 = 0.0350, and wR 2 = 0.0749. Single crystal X-ray diffraction analysis reveals that the V atom is coordinated by the phenolate O, imino N and enolate O atoms of the hydrazone ligand, and the carbonyl O and hydroxy O atoms of benzohydroxamate ligand, and one oxo O group, in an octahedral coordination. Catalytic oxidation of the complex on some olefins was performed.

Role of Recrystallization in Alkaline Treatment on the Catalytic Activity of 1-Butene Epoxidation

Zuo, Yi,Yang, Liqian,Jiang, Xiao,Ma, Mengtong,Wang, Yanli,Liu, Min,Song, Chunshan,Guo, Xinwen

, p. 6196 - 6204 (2020)

Two alkylol amines, which were ethanolamine (EOA) and triethanolamine (TEOA), were used to posttreat nanosized titanium silicalite-1 (TS-1) to improve its catalytic activity for 1-butene epoxidation. Comparative studies were conducted to clarify the influences of the EOA and TEOA concentrations on the physicochemical properties through detailed characterization. EOA treatment can dissolve the framework Si, [SiO4], on the external surface of TS-1, generating some macropores. TEOA serves as structure-directing agent to form MFI topology other than the dissolution of [SiO4], and promotes the recrystallization of [SiO4], forming new TS-1 particles over the external surface. The two treatments can both improve the catalytic activity of 1-butene epoxidation, but the samples treated with TEOA exhibit better catalytic stability. This can be attributed to the characteristic recrystallization of [SiO4] in the case of TEOA treatment, stabilizing the structure of TS-1 and maintaining more framework Ti and intercrystal space.

Characterization and evaluation of Ag-Pt/SiO2 catalysts prepared by electroless deposition

Schaal, Melanie T.,Pickerell, Anna C.,Williams, Christopher T.,Monnier, John R.

, p. 131 - 143 (2008)

A series of Ag-Pt/SiO2 catalysts have been prepared by the electroless deposition of Ag onto a Pt/SiO2 catalyst. Results indicate that Ag deposition does not readily occur on the SiO2 support, but is essentially restricted

Deboronation-assisted construction of defective Ti(OSi)3OH species in MWW-type titanosilicate and their enhanced catalytic performance

Chen, Zhen,He, Mingyuan,Liu, Haoxin,Liu, Wei,Liu, Yueming,Tang, Zhimou,Wang, Rui,Wu, Haihong,Yu, Yunkai

, p. 2905 - 2915 (2020)

A thorough investigation of the nature of the Ti species in the boron-containing Ti-MWW zeolite has been carried out. It was found that the inactive extra-framework TiO6 species can cover up the zeolite Lewis-acid property through the weak atomic binding forces between the Ti(iv) atom and O atom (TiO6 species). The nitric acid treatment could remove these TiO6 species easily from the as-synthesized Ti-MWW(P), followed by exposure of the zeolite Lewis acidity. Importantly, the formation of new Ti(OSi)3OH species with a strong Lewis-acid strength, is facilitated in the modification process. Thereby, the modified Ti-MWW zeolite has an improved catalytic activity in alkene epoxidation reactions. The removal of framework B(iv) species around the TiO4 species is an essential step because it can accelerate the transformation of perfect Ti(OSi)4 species to the defective Ti(OSi)3OH species in zeolites. Moreover, the strategy to construct Ti(OSi)3OH species was also applied successfully in boron-containing Ti-MCM-56 zeolites. Considering active species environment can be modulated effectively with the removal of framework tetra-coordinate boron, this strategy could also be beneficial for the preparation of other high-performance titanosilicates.

Synthesis, crystal structure and catalytic property of a dinuclear cobalt(III) complex derived from 2-ethyl-2-{[1-(2-hydroxy-5-methylphenyl)methylidene]amino}propane-1,3-diol

Qiu, Xiao-Yang

, p. 182 - 186 (2018)

With a tetradentate Schiff base ligand 2-ethyl-2-{[1-(2-hydroxy-5-methylphenyl)methylidene]amino}propane-1,3-diol (H3L) with cobalt nitrate and ammonium thiocyanate, a dinuclear cobalt(III) complex was prepared and characterized by elemental analysis, IR spectroscopy and X-ray structure determination. The complex crystallizes in the monoclinic space group P21/n with unit cell dimensions a = 17.682(2) ?, b = 22.652(2) ?, c = 18.617(2) ?, β = 99.546(2)°, V = 7,353.5(12) ?3, Z = 4, R1 = 0.0956, and wR2 = 0.2027. Single crystal X-ray diffraction analysis reveals that the asymmetric unit of the compound contains two dinuclear cobalt(III) complex molecules, three methanol molecules and one water molecule of crystallization. The Co???Co distances in the dinuclear cobalt(III) complex molecules are about 2.97 ?. The Co atoms are in octahedral coordination. The complex has effective property on the oxidation of various aliphatic and aromatic olefins.

Catalytic Asymmetric Cyclization of Some Bromohydrins with Chiral Cobalt Complex

Takeichi, Tsutomu,Takakura, Teruo,Ishimori, Michihiro,Tsuruta, Teiji

, p. 603 - 605 (1988)

Asymmetric cyclization of a variety of bromohydrins with base was examined in the presence of an optically active cobalt(salen) type complex.Optically active oxiranes of modest optical purities were obtained. erythro-3-Bromo-2-butanol and threo-3-bromo-2-butanol were cyclized similarly, and only trans-2,3-dimethyloxirane and cis-2,3-dimethyloxirane were obtained, respectively, indicating that the cyclization of bromohydrin proceeds by complete SN2 type reaction.

Structural and dynamical aspects of alkylammonium salts of a silicodecatungstate as heterogeneous epoxidation catalysts

Uchida, Sayaka,Kamata, Keigo,Ogasawara, Yoshiyuki,Fujita, Megumi,Mizuno, Noritaka

, p. 9979 - 9983 (2012)

The structural and dynamical aspects of alkylammonium salts of a silicodecatungstate [(CH3)4N]4[γ-SiW 10O34(H2O)2] [C1], [(n-C 3H7)4N]4[γ-SiW 10O34(H2O)2] [C3], [(n-C 4H9)4N]4[γ-SiW 10O34(H2O)2] [C4], and [(n-C 5H11)4N]4[γ-SiW 10O34(H2O)2] [C5] were investigated. The results of sorption isotherms, XRD analyses, and solid-state NMR spectroscopy show that facile sorption of solvent molecules, flexibility of structures, and high mobility of alkylammonium cations are crucial to the uniform distribution of reactant and oxidant molecules throughout the bulk solid, which are related to the high catalytic activities for epoxidation of alkenes.

Liquid- and vapor-phase hydrogenation of 1-epoxy-3-butene using self-assembled monolayer coated palladium and platinum catalysts

Kahsar, Karl R.,Schwartz, Daniel K.,Medlin, J. Will

, p. 102 - 106 (2012)

Alkanethiol self-assembled monolayers (SAMs) have recently been shown to be effective catalyst modifiers for increasing the selectivity of the hydrogenation of 1-epoxy-3-butene (EpB) to 1-epoxybutane in the gas phase. In the results reported here, we demonstrate that SAM coatings can similarly be applied to other supported metals (Pt) and in liquid-phase reaction environments. Coating a Pt/Al2O3 catalyst with n-octadecanethiol resulted in a large improvement in selectivity during vapor-phase EpB hydrogenation, similar to that observed for supported Pd. The liquid phase hydrogenation of EpB using SAM-coated catalysts showed similar selectivity trends in some cases, but interactions of the solvent with the SAM were also important in controlling selectivity. In particular, using a heptane solvent, epoxybutane selectivity increased from 36% with an uncoated Pd/Al 2O3 catalyst to 74% with a thioglycerol SAM-coated catalyst. SAM quality was shown to have a strong impact on the rate of reaction but little effect on selectivity. The results generally indicated that selectivity modification with thiol SAMs is extendable to other supported metals and a variety of reaction environments.

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