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Cas Database

100-40-3

100-40-3

Identification

  • Product Name:4-Vinyl-1-cyclohexene

  • CAS Number: 100-40-3

  • EINECS:202-848-9C6H9CH=CH2

  • Molecular Weight:108.183

  • Molecular Formula: C8H12

  • HS Code:29021900

  • Mol File:100-40-3.mol

Synonyms:Cyclohexene,4-vinyl- (8CI);1-Vinyl-3-cyclohexene;4-Ethenyl-1-cyclohexene;4-Ethenylcyclohexene;4-VCH;4-Vinyl-1-cyclohexene;4-Vinylcyclohexene;NSC15760;Vinylcyclohexene;

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Safety information and MSDS view more

  • Pictogram(s):3.1 UN NO.

  • Hazard Codes:F,Xn

  • Signal Word:Warning

  • Hazard Statement:H351 Suspected of causing cancer

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Remove contaminated clothes. Rinse skin with plenty of water or shower. In case of eye contact First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention. If swallowed Refer for medical attention . Exposure can cause irritation of eyes, nose and throat. High concentrations have a narcotic effect. (USCG, 1999) Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Aliphatic hydrocarbons and related compounds/

  • Fire-fighting measures: Suitable extinguishing media To fight fire, use foam, CO2, dry chemical. Special Hazards of Combustion Products: Irritating vapors and toxic gases, such as carbon dioxide and carbon monoxide, may be formed when involved in fire. Behavior in Fire: Vapors can flow along surfaces to distant ignition source and flash back. (USCG, 1999) Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in dry sand or inert absorbent. Then store and dispose of according to local regulations. Do NOT wash away into sewer. PRECAUTIONS FOR "CARCINOGENS": A high-efficiency particulate arrestor (HEPA) or charcoal filters can be used to minimize amt of carcinogen in exhausted air ventilated safety cabinets, lab hoods, glove boxes or animal rooms ... Filter housing that is designed so that used filters can be transferred into plastic bag without contaminating maintenance staff is avail commercially. Filters should be placed in plastic bags immediately after removal ... The plastic bag should be sealed immediately ... The sealed bag should be labelled properly ... Waste liquids ... should be placed or collected in proper containers for disposal. The lid should be secured & the bottles properly labelled. Once filled, bottles should be placed in plastic bag, so that outer surface ... is not contaminated ... The plastic bag should also be sealed & labelled. ... Broken glassware ... should be decontaminated by solvent extraction, by chemical destruction, or in specially designed incinerators. /Chemical Carcinogens/

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Fireproof. Separated from oxidants. Cool. Store only if stabilized.PRECAUTIONS FOR "CARCINOGENS": Storage site should be as close as practical to lab in which carcinogens are to be used, so that only small quantities required for ... expt need to be carried. Carcinogens should be kept in only one section of cupboard, an explosion-proof refrigerator or freezer (depending on chemicophysical properties ...) that bears appropriate label. An inventory ... should be kept, showing quantity of carcinogen & date it was acquired ... Facilities for dispensing ... should be contiguous to storage area. /Chemical Carcinogens/

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price view more

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  • Manufacture/Brand:TRC
  • Product Description:4-Vinyl-1-cyclohexene
  • Packaging:10ml
  • Price:$ 65
  • Delivery:In stock
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  • Manufacture/Brand:TRC
  • Product Description:4-Vinyl-1-cyclohexene
  • Packaging:5ml
  • Price:$ 50
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  • Manufacture/Brand:TRC
  • Product Description:4-Vinyl-1-cyclohexene
  • Packaging:1ml
  • Price:$ 40
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  • Manufacture/Brand:TCI Chemical
  • Product Description:4-Vinyl-1-cyclohexene (stabilized with BHT) >95.0%(GC)
  • Packaging:100mL
  • Price:$ 112
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  • Manufacture/Brand:TCI Chemical
  • Product Description:4-Vinyl-1-cyclohexene (stabilized with BHT) >95.0%(GC)
  • Packaging:25mL
  • Price:$ 32
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:4-Vinyl-1-cyclohexene analytical standard
  • Packaging:5ml
  • Price:$ 52.3
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:4-Vinyl-1-cyclohexene analytical standard
  • Packaging:25ml
  • Price:$ 213
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:4-Vinylcyclohex-1-ene 95+%
  • Packaging:1g
  • Price:$ 1092
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:4-Vinylcyclohex-1-ene 95+%
  • Packaging:250mg
  • Price:$ 492
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Relevant articles and documentsAll total 96 Articles be found

Hidai et al.

, p. 1243,1244 (1965)

Dehydrogenative Vacuum Pyrolysis: a Novel Synthetic Technique. Conversion of Cyclo-octa-1,5-diene into Styrene and Related Reactions

Buchan, Caroline M.,Cadogan, J. I. G.,Gosney, Ian,Hamill, Brendan J.,Newlands, Stephen F.,Whan, David A.

, p. 725 - 726 (1983)

Vacuum pyrolysis in the presence of palladium on charcoal of the 3,3-dioxide (1) of 3-thiabicyclo-heptane-6,7-dicarboxylic anhydride gave, without undesirable disproportionation, phthalic anhydride, also obtained from cis-2,3-divinylsuccinic anhydride (2) and cis-1,2,3,6-tetrahydrophthalic anhydride (5), while cyclo-octa-1,5-diene (7) and the disulphone (6) each gave styrene.

Precursor effect on the property and catalytic behavior of Fe-TS-1 in butadiene epoxidation

Wu, Mei,Zhao, Huahua,Yang, Jian,Zhao, Jun,Song, Huanling,Chou, Lingjun

, p. 2103 - 2109 (2017)

The effect of iron precursor on the property and catalytic behavior of iron modified titanium silicalite molecular sieve (Fe-TS-1) catalysts in butadiene selective epoxidation has been studied. Three Fe-TS-1 catalysts were prepared, using iron nitrate, iron chloride and iron sulfate as precursors, which played an important role in adjusting the textural properties and chemical states of TS-1. Of the prepared Fe-TS-1 catalysts, those modified by iron nitrate (FN-TS-1) exhibited a significant enhanced performance in butadiene selective epoxidation compared to those derived from iron sulfate (FS-TS-1) or iron chloride (FC-TS-1) precursors. To obtain a deep understanding of their structure-performance relationship, X-ray diffraction (XRD), X-ray photoelectron spectroscopy (XPS), Temperature programmed desorption of NH3 (NH3-TPD), Diffuse reflectance UV–Vis spectra (DR UV–Vis), Fourier transformed infrared spectra (FT-IR) and thermal gravimetric analysis (TGA) were conducted to characterize Fe-TS-1 catalysts. Experimental results indicated that textural structures and acid sites of modified catalysts as well as the type of Fe species influenced by the precursors were all responsible for the activity and product distribution.

Nickel(0) and palladium(0) complexes with 1,3,5-triaza-7-phosphaadamantane. Catalysis of buta-1,3-diene oligomerization or telomerization in an aqueous biphasic system

Cermak, Jan,Kvicalova, Magdalena,Blechta, Vratislav

, p. 355 - 363 (1997)

New homoleptic nickel(0) and palladium(0) complexes with a water-soluble ligand, 1,3,5-triaza-7-phosphaadamantane, were prepared and characterized by 1H, 13C, and 31P NMR spectra. The complexes, together with the known ana

The positive role of cadmium in TS-1 catalyst for butadiene epoxidation

Wu, Mei,Song, Huanling,Wang, Fang,Chou, Lingjun

, p. 207 - 212 (2013)

A series of Cd modified titanium silicalite 1 catalysts with different Cd content (xCd-TS-1, x = 1-15) were successfully prepared by ultrasound impregnation. Epoxidation of butadiene over these catalysts were investigated using hydrogen peroxide as oxidant, which indicated that Cd greatly improve the catalytic performance of TS-1 and the selectivity of epoxide. Various characterization methods including quantum chemical calculation were employed to explore the specific roles of Cd in promoting TS-1 catalytic activity. Theoretical calculation consistently suggested TiO bond were weakened owing to the introduction of Cd, which resulted in the structure of Cd-TS-1 becoming more relaxant. As a consequence, it is favorable to methanol solvent and H 2O2 interacting with the Ti active site to form five-member transition state during reaction. It was observed that catalysts modified with 1-5 wt% Cd presented both high catalytic activity and good reusability. The highest yield of 0.63 mol/L of vinyloxirane (VO) was obtained, while turnover number (TON, determined as the molar VO obtained per molar Ti atom) could reach to 1466.

Jenkins,R.L. et al.

, p. 347 - 357 (1975)

Synthesis of p-(Cyclohexene-3-yl-ethyl)phenol and Characteristics of its Phosphatization with Phosphorous Trichloride

Mirzoev,Rasulov,Gasanov,Manafov

, p. 762 - 766 (2018)

Cycloalkenylation of phenol with 4-vinylcyclohexene was studied in the presence of zeolite-Y catalyst, saturated by orthophosphoric acid on the batch unit. Phenol and 4-vinylcyclohexene were used as initial products for the realization of cycloalkenylatio

Epoxidation of butadiene over nickel modified TS-1 catalyst

Wu, Mei,Chou, Lingjun,Song, Huanling

, p. 627 - 636 (2012)

Nickel modified Titanium silicalite 1 (TS-1) catalysts provided an environmentally benign and effective method for butadiene epoxidation. Certain loading of modified Ni in our system significantly promoted TS-1 catalytic activity. The product vinyloxirane

-

Bartlett,P.D.,Schueller,K.E.

, p. 6071 - 6077 (1968)

-

Hidai,M. et al.

, p. 1357 - 1364 (1966)

-

Rowley,Steiner

, p. 198,204,206 (1951)

-

Dimerization of 1,3-butadiene on highly characterized hydroxylated surfaces of ultrathin films of γ-Al2O3 [3]

Ivey,Allen,Avoyan,Martin,Hemminger

, p. 10980 - 10981 (1998)

-

Srinivasan,Sonntag

, p. 3778 (1965)

Srinivasan,Levi

, p. 3756,3758 (1964)

-

Duncan,Janz

, p. 1644 (1952)

-

Seed-mediated Growth of Alloyed Ag-Pd Shells toward Alkyne Semi-hydrogenation Reactions under Mild Conditions?

Zheng, Yuqin,Tan, Taixing,Wang, Cheng

, p. 3071 - 3078 (2021)

Ag@Ag-Pdx core-shell nanocomposites with various Ag/Pd ratio were deposited on Ag nanoplates using a seed growth method. When physically loaded on C3N4, Ag@Ag-Pd0.077/C3N4 with optimized Ag/Pd ratio could accomplish high catalytic performance for the semi-hydrogenation of phenylacetylene as well as other aliphatic (both terminal and internal alkynes) alkynes and phenylcycloalkynes containing functional groups (such as ester, hydroxyl, ethyl groups) under room temperature and 1 atm H2. The alloying and ensemble effects are used to interpret such catalytic performance.

Mechanistic Insight into High-Spin Iron(I)-Catalyzed Butadiene Dimerization

Lee, Heejun,Campbell, Michael G.,Hernández Sánchez, Raúl,B?rgel, Jonas,Raynaud, Jean,Parker, Sarah E.,Ritter, Tobias

, p. 2923 - 2929 (2016)

Iron complexes are commonly used in catalysis, but the identity of the active catalyst is often unknown, which prevents a detailed understanding of structure-reactivity relationships for catalyst design. Here we report the isolation and electronic structure determination of a well-defined, low-valent iron complex that is an active catalyst in the synthesis of cis,cis-1,5-cyclooctadiene (COD) from 1,3-butadiene. Spectroscopic and magnetic characterization establishes a high-spin Fe(I) center, which is supported by DFT studies, where partial metal-ligand antibonding orbital population is proposed to allow for facile ligand exchange during catalysis.

?-Arene Complexes of Nickel(II). Synthesis (from Metal Atoms) of (?-Arene)bis(pentafluorophenyl)nickel(II). Properties, ?-Arene Lability, and Chemistry

Gastinger, Robert G.,Anderson, Bruce B.,Klabunde, Kenneth J.

, p. 4959 - 4966 (1980)

A new series of transition-metal-?-arene complexes has been prepared by a metal atom synthetic method.The deposition of Ni vapor, C6F5Br, and arenes has prodused high yields of (C6F5)2Ni-?-arene complexes.A variety of ?-arene ligands are η6 bound by the (C6F5)2Ni moiety, resulting in soluble highly labile materials, where the ?-arene ligand is exchangeble at room temperature.These complexes have not been isolable when ?-bonding ligands other then C6F5 have been employed.The formation of the ?-toluene complex proceeds through a pseudostable C6F5NiBr species that can be trapped at -80 deg C with R3P but decomposes by reductive elimination of CF5-CF5 in the absence of R3P or electron-rich arenes.It is likely that C6F5NiBr-?-arene is formed initially, which then disproportionates to (C6F5)2Ni-?-arene and NiBr2.Due to the high lability of the ?-arene ligand, these complexes possess a rich chemistry.Displacement of the ?-arene ligand can bee carried out cleanly and in high yield by P(Et)3, 1,5-cyclooctadiene, and THF to form (C6F5)2NiL2.Treatment of (?-toluene)bis(pentafluorophenyl)nickel (1) with norbornadiene at 0 deg C causes the formation of a high polymer of norbornadiene as well as (?-norbornadiene)bis(pentafluorophenyl)nickel, which appears to be either the active polymerization catalyst or its precursor.Similarly, treatment of 1 with 1,3-butadiene at 25 deg C and 1 atm causes the formation of new organometallic compound and the production of cyclic tetramers of 1,3-butadiene.When 1 was treated with cyclopentadiene at 0 deg C, a rapid production of C6F5H was observed with the subsequent formation of a dimeric nickel complex (C6F5)2(Cp)2Ni2(C5H6) where the Ni atoms appear to be bound together through a mutually ?-bonded cyclopentadiene (C5H6) ligand.Reductive elimination reactions have also been induced under mild conditions by addition of CO or C2H4.With CO a nearly quantitative production of C6F5C6F5 and Ni(CO)4 took place.Lastly, 1 served as a short-lived arene hydrogenation catalyst at room temperature.

Cardenas

, p. 264 (1970)

-

Janz,De Crescente

, p. 1470 (1959)

-

Catalytic conversion of butadiene to ethylbenzene over the nanoporous nickel(II) phosphate, VSB-1

Chang,Park,Gao,Ferey,Cheetham

, p. 859 - 860 (2001)

The large-pore nickel(II) phosphate, VSB-1, shows excellent selectivity (> 80%) for the dehydrocyclodimerization of butadiene to ethylbenzene at 400 °C; conversion to 4-vinylcyclohexene and oligomeric byproducts is 5% in each case.

Ballivet et al.

, p. L58 (1977)

Improving the performance of palladium-catalysed telomerization of 1,3-butadiene by metallocene-based phosphine ligand

Dong, Kaiwu,Shen, Chaoren,Tian, Xinxin,Xu, Zhengshuai,Zhang, Hongru

, (2021/09/24)

By replacing one planar phenyl group of PPh3 with bulkier ferrocenyl or ruthenocenyl group, the performance of resulted metallocene-based phosphine ligand in the telomerization of 1,3-butadiene with methanol has been largely elevated compared t

Process route upstream and downstream products

Process route

2,5-dihydrofuran
1708-29-8

2,5-dihydrofuran

cis-8-oxabicyclo<4.3.0>non-3-ene
3470-42-6,3471-41-8,4743-55-9,56000-18-1

cis-8-oxabicyclo<4.3.0>non-3-ene

4-ethenylcyclohexene
100-40-3

4-ethenylcyclohexene

Conditions
Conditions Yield
at 180 ℃;
1,5-cis,cis-cyclooctadiene
1552-12-1,111-78-4

1,5-cis,cis-cyclooctadiene

4-ethenylcyclohexene
100-40-3

4-ethenylcyclohexene

Conditions
Conditions Yield
at 430 ℃;
1-phenylethyl acetate
74454-29-8

1-phenylethyl acetate

4-ethenylcyclohexene
100-40-3

4-ethenylcyclohexene

Conditions
Conditions Yield
With quartz tube; at 400 - 450 ℃;
4-ethenylcyclohexene
100-40-3

4-ethenylcyclohexene

Conditions
Conditions Yield
at 418 - 650 ℃; Kinetics; Dimerisierung;
at 356.9 - 426.9 ℃; Equilibrium constant; experimentell;
at 476.9 - 676.9 ℃; Equilibrium constant; berechnet;
(1.5-COD)(5-ethylcyclohexenyl)Rh(I); Product distribution; Mechanism; further (η-cycloenyl)(η-1,5-cyclooctadiene)Rh(I)-complexes; oligomerization;
Na-ZSM-20; In hexane; at 250 ℃; rate of conversion; other non acidic zeolites; also carbon mol. sieves; other solvents and temperatures;
With hydroxylated γ-Al2O3 on NiAl(100); at -133.1 ℃; Product distribution; Mechanism; also non-hydroxylated Al2O3;
With copper naphthenate; at 160 ℃; under 29420.3 - 735508 Torr;
at 480 ℃; under 735.5 - 5148.6 Torr;
With hydroquinone; at 150 ℃;
bei der Waermepolymerisation;
at -120 ℃;
In neat (no solvent); at 175 ℃; for 6h; Time; Temperature; chemoselective reaction; High pressure;
at 70 ℃;
With copper on zeolite;
With hydroquinone; at 150 ℃;
4-ethenylcyclohexene
100-40-3

4-ethenylcyclohexene

trans-1,2-diethenylcyclobutane
6553-48-6

trans-1,2-diethenylcyclobutane

Conditions
Conditions Yield
at 150 ℃; under 73550.8 Torr;
4-ethenylcyclohexene
100-40-3

4-ethenylcyclohexene

cis-1,2-divinylcyclobutane
16177-46-1

cis-1,2-divinylcyclobutane

trans-1,2-diethenylcyclobutane
6553-48-6

trans-1,2-diethenylcyclobutane

Conditions
Conditions Yield
Irradiation;
piperidine
110-89-4

piperidine

(E)-1,3,7-octatriene
26198-79-8

(E)-1,3,7-octatriene

(E)-1-(octa-2,7-dien-1-yl)piperidine
67732-44-9

(E)-1-(octa-2,7-dien-1-yl)piperidine

2,5-divinyltetrahydropyran
25724-33-8

2,5-divinyltetrahydropyran

4-ethenylcyclohexene
100-40-3

4-ethenylcyclohexene

Conditions
Conditions Yield
With formaldehyd; Ps(acac)2; triethylaluminum; triphenylphosphine; In toluene;
piperidine
110-89-4

piperidine

3-piperidyl-1,7-octadiene
64579-51-7,78344-18-0,78344-19-1

3-piperidyl-1,7-octadiene

N-2,7-octadienylpiperidine
25017-07-6

N-2,7-octadienylpiperidine

4-ethenylcyclohexene
100-40-3

4-ethenylcyclohexene

Conditions
Conditions Yield
With bis(acetylacetonate)nickel(II); ((+)-menthyl)2PPh; triethylaluminum; In benzene; at -8 ℃; for 720h;
71%
17%
12%
1-piperidinomethanol
2494-10-2

1-piperidinomethanol

(E)-1,3,7-octatriene
26198-79-8

(E)-1,3,7-octatriene

(E)-1-(octa-2,7-dien-1-yl)piperidine
67732-44-9

(E)-1-(octa-2,7-dien-1-yl)piperidine

2,5-divinyltetrahydropyran
25724-33-8

2,5-divinyltetrahydropyran

4-ethenylcyclohexene
100-40-3

4-ethenylcyclohexene

N-2,6,8-nonatrienylpiperidine
74067-07-5

N-2,6,8-nonatrienylpiperidine

1,1'-piperidyl-3,8-nonadiene
74067-08-6

1,1'-piperidyl-3,8-nonadiene

Conditions
Conditions Yield
palladium(II) acetylacetonate; triethylaluminum; triphenylphosphine; In toluene; at 120 ℃; for 10h; Product distribution; telomerization of butadiene with N-hydroxymethylamines (N-hydroxymethylpiperidine and N-hydroxymethyldiethylamine) in the presence of Pd catalyst, mixed telomerization of butadiene with formaldehyde and secondary amines (piperidine and diethylamine);
1-piperidinomethanol
2494-10-2

1-piperidinomethanol

(E)-1-(octa-2,7-dien-1-yl)piperidine
67732-44-9

(E)-1-(octa-2,7-dien-1-yl)piperidine

4-ethenylcyclohexene
100-40-3

4-ethenylcyclohexene

N-2,6,8-nonatrienylpiperidine
74067-07-5

N-2,6,8-nonatrienylpiperidine

1,1'-piperidyl-3,8-nonadiene
74067-08-6

1,1'-piperidyl-3,8-nonadiene

Conditions
Conditions Yield
Ps(acac)2; triethylaluminum; triphenylphosphine; In toluene; at 120 ℃; for 10h; Yield given. Further byproducts given. Yields of byproduct given;

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