Conditions | Yield |
---|---|
100% | |
50% |
1,1,2,2-tetrachloroethylene
A
cis-1,2-Dichloroethylene
B
trans-1,2-dichloroethylene
C
Trichloroethylene
Conditions | Yield |
---|---|
With methanol at 20℃; Inert atmosphere; UV-irradiation; | A n/a B n/a C 43% |
With Desulfomonile tiedjei DCB-1 In water at 35℃; Kinetics; Further Variations:; Reagents; time; concentration; Dehalogenation; |
Conditions | Yield |
---|---|
at 100 - 250℃; Gleichgewicht der photochemischen Isomerisierung in der Gasphase im UV-Licht; | |
at 300℃; Gleichgewicht der thermischen Isomerisierung; | |
at 350℃; Gleichgewicht der thermischen Isomerisierung; |
Conditions | Yield |
---|---|
With oxygen; chlorine; copper(II) oxide at 375 - 425℃; |
1,1,2-trichloroethane
A
cis-1,2-Dichloroethylene
B
trans-1,2-dichloroethylene
Conditions | Yield |
---|---|
With copper chloride +pumice stone at 400 - 450℃; | |
With copper chloride; pumice stone at 400 - 450℃; |
1,1,2-trichloroethane
A
cis-1,2-Dichloroethylene
B
trans-1,2-dichloroethylene
C
1,1-Dichloroethylene
Conditions | Yield |
---|---|
at 500℃; bei der thermischen Zersetzung; | |
at 500℃; Geschwindigkeit dieser Spaltung bei verschiedenen Temperaturen und Beschleunigung der Pyrolyse durch geringe Mengen Sauerstoff oder Chlor; |
Conditions | Yield |
---|---|
With chlorine In solid at -213.1℃; Product distribution; Quantum yield; Mechanism; Irradiation; various temperatures; | |
With antimonypentachloride | |
With nitrosylchloride at 350℃; |
Conditions | Yield |
---|---|
With aqueous CuCl2+CuCl+NH4Cl at 50 - 85℃; | |
With iron(III) chloride; ammonium chloride; copper(l) chloride at 50 - 85℃; | |
With hydrogenchloride; water; copper(l) chloride at 80 - 110℃; |
Conditions | Yield |
---|---|
With chlorine; pyrographite at 40℃; | |
With chlorine; copper dichloride at 200 - 240℃; |
1,1,2,2-tetrachloroethane
A
cis-1,2-Dichloroethylene
B
trans-1,2-dichloroethylene
Conditions | Yield |
---|---|
With sodium amalgam; water | |
With hydrogen; copper at 370 - 440℃; | |
With zinc In ethanol |
1,1,2-trichloroethane
A
cis-1,2-Dichloroethylene
B
trans-1,2-dichloroethylene
C
chloroethylene
D
chloroacetylene
E
1,1-Dichloroethylene
F
acetylene
Conditions | Yield |
---|---|
under 0.2 Torr; Product distribution; Mechanism; Irradiation; laser photolysis, var. pressure, var. pulse energy, presence of var. gases; |
1,1-Dichloroethylene
A
cis-1,2-Dichloroethylene
B
trans-1,2-dichloroethylene
C
Ethyne; compound with chlorine
D
Chloro-ethyne; hydrochloride
Conditions | Yield |
---|---|
With in Xe matrix at -261.2℃; Product distribution; Thermodynamic data; Irradiation; or with 1,1-dichloroethene-d2; |
1,1-Dichloroethylene
A
cis-1,2-Dichloroethylene
B
trans-1,2-dichloroethylene
C
Chloro-ethyne; hydrochloride
Conditions | Yield |
---|---|
With in Kr matrix at -261.2℃; Product distribution; Thermodynamic data; Irradiation; |
acetylene
A
cis-1,2-Dichloroethylene
B
trans-1,2-dichloroethylene
C
1,1,2,2-tetrachloroethane
Conditions | Yield |
---|---|
With chlorine at 21.9℃; under 700 Torr; for 0.00277778h; Product distribution; Mechanism; Irradiation; FTIR spectroscopic studies; |
1,1,2-trichloroethane
A
cis-1,2-Dichloroethylene
B
trans-1,2-dichloroethylene
C
chloroethylene
D
chloroacetylene
E
1,1-Dichloroethylene
Conditions | Yield |
---|---|
With chloroethane; silicon tetrafluoride at 856.9 - 1076.9℃; Kinetics; Mechanism; Product distribution; Irradiation; also pyrolysis of 1,1,1-trichloroethane; | A 15.6 % Chromat. B 13.3 % Chromat. C 1.58 % Chromat. D 0.4 % Chromat. E 0.44 % Chromat. |
2,3-Dimethyl-2-butene
A
cis-1,2-Dichloroethylene
B
trans-1,2-dichloroethylene
Conditions | Yield |
---|---|
at 30℃; Product distribution; Mechanism; Rate constant; Irradiation; other diazirines; var. temp.; also without irradiation; energy data: ΔHT; |
Conditions | Yield |
---|---|
With sodium chloride; zinc at 23℃; Kinetics; Reduction; anaerobic; |
Conditions | Yield |
---|---|
With sodium chloride; zinc at 23℃; Kinetics; Dehalogenation; anaerobic; |
1,1,2,2-tetrachloroethylene
A
trans-1,2-dichloroethylene
B
ethene
C
chloroethylene
D
acetylene
Conditions | Yield |
---|---|
With titanium(III) citrate; water; cyanocobalamin at 20℃; for 240h; Kinetics; Further Variations:; Reagents; Dehalogenation; β-elimination; |
Trichloroethylene
A
cis-1,2-Dichloroethylene
B
trans-1,2-dichloroethylene
C
ethene
D
1,1-Dichloroethylene
Conditions | Yield |
---|---|
iron In water for 0.866667h; Dehalogenation; |
Trichloroethylene
A
cis-1,2-Dichloroethylene
B
trans-1,2-dichloroethylene
C
ethene
D
acetylene
Conditions | Yield |
---|---|
With vitamin B-12; titanium(III) citrate In water at 35℃; pH=7.05; Kinetics; Further Variations:; pH-values; Reagents; Reduction; dehalogenation; |
Trichloroethylene
A
cis-1,2-Dichloroethylene
B
trans-1,2-dichloroethylene
C
1,1-Dichloroethylene
D
acetylene
Conditions | Yield |
---|---|
With titanium(III) citrate; water; cyanocobalamin at 20℃; for 280h; Kinetics; Further Variations:; Reagents; Dehalogenation; β-elimination; |
1,1,2,2-tetrachloroethane
A
cis-1,2-Dichloroethylene
B
trans-1,2-dichloroethylene
C
Trichloroethylene
D
acetylene
Conditions | Yield |
---|---|
With iron sulfide In water at 25℃; pH=8.3; Kinetics; Dehydrochlorination; dechlorination; |
Conditions | Yield |
---|---|
Kinetics; auch in Gegenwart von Antimonbromid; |
Conditions | Yield |
---|---|
at 185℃; Gleichgewicht der Isomerisierung in der Gasphase; | |
at 275℃; Gleichgewicht der Isomerisierung in der Gasphase; | |
at 150℃; under 7355.08 Torr; Rate constant; Isomerisierung; |
cis-1,2-Dichloroethylene
iodine
benzene
trans-1,2-dichloroethylene
Conditions | Yield |
---|---|
at 100 - 120℃; Kinetics; photochemische Isomerisierung; |
Conditions | Yield |
---|---|
at 180℃; Kinetics; Isomerisierung in der Gasphase; |
water
1,1,2,2-tetrachloroethane
A
cis-1,2-Dichloroethylene
B
trans-1,2-dichloroethylene
acetylene
1,1,2,2-tetrachloroethane
A
cis-1,2-Dichloroethylene
B
trans-1,2-dichloroethylene
C
Trichloroethylene
Conditions | Yield |
---|---|
at 350℃; | |
at 350℃; |
trans-1,2-dichloroethylene
Chlorine(I) trifluoromethanesulfonate
Trifluoro-methanesulfonic acid 1,2,2-trichloro-ethyl ester
Conditions | Yield |
---|---|
In Dichlorodifluoromethane at -111 - -70℃; for 6h; | 100% |
-111 to -70°C, 6 h; | |
-111 to -70°C, 6 h; |
trans-1,2-dichloroethylene
Bromine(I) trifluoromethanesulfonate
Trifluoro-methanesulfonic acid 2-bromo-1,2-dichloro-ethyl ester
Conditions | Yield |
---|---|
In Dichlorodifluoromethane at -111 - -100℃; for 1h; | 99% |
trans-1,2-dichloroethylene
bis[bis(trimethylsilyl)methyl]germanium(II)
[CHGeCl(CH(Si(CH3)3)2)2]2
Conditions | Yield |
---|---|
In toluene 2 equiv. alkene, refluxing for 24 h; chromy. (SiO2, hexane); elem. anal.; | 99% |
Conditions | Yield |
---|---|
98% | |
With triethylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In benzene at 20℃; for 6h; | 94% |
trans-1,2-dichloroethylene
1-Phenyl-2-propyn-1-ol
(1E)-1-chloro-5-phenylpent-1-en-3-yn-5-ol
Conditions | Yield |
---|---|
With piperidine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran for 1h; Ambient temperature; | 98% |
trans-1,2-dichloroethylene
tris-iso-propylsilyl acetylene
(E)-(4-chlorobut-3-en-1-yn-1-yl)triisopropylsilane
Conditions | Yield |
---|---|
With piperidine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In diethyl ether at 20℃; for 5h; Inert atmosphere; Darkness; | 97% |
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 20℃; for 2h; | 91% |
Conditions | Yield |
---|---|
With iodine; N-butylamine; tetrakis(triphenylphosphine) palladium(0) In benzene for 6h; Ambient temperature; | 95% |
With piperidine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In benzene at 20℃; for 2h; | 92% |
With piperidine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In diethyl ether for 4h; Ambient temperature; | 82% |
Conditions | Yield |
---|---|
With copper(l) iodide; N-butylamine; tetrakis(triphenylphosphine) palladium(0) In benzene for 5h; Ambient temperature; | 95% |
trans-1,2-dichloroethylene
methyl propargyl sulphide
(Z)-1-Chloro-5-methylsulfanyl-pent-1-en-3-yne
Conditions | Yield |
---|---|
With copper(l) iodide; N-butylamine; tetrakis(triphenylphosphine) palladium(0) In benzene for 5h; Ambient temperature; | 95% |
trans-1,2-dichloroethylene
sodium isopropanethiolate
2-{[(E)-2-(propan-2-ylsulfanyl)ethenyl]sulfanyl}propane
Conditions | Yield |
---|---|
In N,N,N,N,N,N-hexamethylphosphoric triamide for 1h; Ambient temperature; | 95% |
trans-1,2-dichloroethylene
3-(tetrahydropyran-2'-yloxy)propyne
(Z)-1-choro-5-<(2-tetrahydropyranyl)oxy>-1-penten-3-yne
Conditions | Yield |
---|---|
With copper(l) iodide; N-butylamine; tetrakis(triphenylphosphine) palladium(0) In benzene for 5h; Ambient temperature; | 95% |
trans-1,2-dichloroethylene
Conditions | Yield |
---|---|
In benzene Irradiation; | 95% |
trans-1,2-dichloroethylene
(3aS,6aR)-3,5,5-Trimethyl-1-oxo-1,3a,4,5,6,6a-hexahydro-pentalene-2-carboxylic acid methyl ester
(2aR,2bS,5aR,6aR)-1,2-Dichloro-2a,4,4-trimethyl-6-oxo-octahydro-cyclobuta[a]pentalene-6a-carboxylic acid methyl ester
Conditions | Yield |
---|---|
In cyclohexane at 20℃; for 6h; Irradiation; | 95% |
Conditions | Yield |
---|---|
With C56H65F5MoN2O In toluene; paraffin oil at 50℃; for 4h; diastereoselective reaction; | 95% |
Conditions | Yield |
---|---|
With 2,3-dimethylbutane In benzene at 20℃; Irradiation; | 94% |
With chlorine at 80 - 95℃; unter Ausschluss von Sauerstoff; |
trans-1,2-dichloroethylene
Conditions | Yield |
---|---|
With pyrex In cyclohexane Irradiation; | 94% |
trans-1,2-dichloroethylene
(E)-1-octen-1-ylboronic acid
(1E,3E)-1-chloro-1,3-decadiene
Conditions | Yield |
---|---|
With cesium fluoride; tris-(dibenzylideneacetone)dipalladium(0); XPhos In 1,4-dioxane at 100℃; Suzuki coupling; | 94% |
trans-1,2-dichloroethylene
Conditions | Yield |
---|---|
With C56H65F5MoN2O In benzene at 22℃; for 0.25h; Glovebox; Inert atmosphere; | 94% |
trans-1,2-dichloroethylene
Conditions | Yield |
---|---|
at 30℃; for 16h; Temperature; Sealed tube; | 94% |
trans-1,2-dichloroethylene
1-butyn-4-ol
(5E)-6-chlorohex-5-en-3-yn-1-ol
Conditions | Yield |
---|---|
With piperidine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In diethyl ether at 15 - 20℃; for 4h; | 93% |
1-Octyn-3-ol
trans-1,2-dichloroethylene
(1E)-1-chloro-5-hydroxy-dec-1-en-3-yne
Conditions | Yield |
---|---|
With piperidine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In benzene at 20℃; for 2h; | 92% |
With piperidine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In diethyl ether for 4h; Ambient temperature; | 85% |
copper; palladium | |
With copper(l) iodide; N-butylamine; tetrakis(triphenylphosphine) palladium(0) In benzene for 4h; Ambient temperature; |
trans-1,2-dichloroethylene
1,4,1',4'-tetrahydro-1,4:1',4'-di-o-benzeno-2,2'-binaphthyl
6,7-dichloro-5,6,7,8,13,14-hexahydro-5,14:8,13-di-o-benzenopentaphene
Conditions | Yield |
---|---|
at 190 - 195℃; for 24h; | 91% |
trans-1,2-dichloroethylene
Acetate de non-8-ynyle
Acetate de (E)-11-chloroundec-10-en-8-ynyle
Conditions | Yield |
---|---|
copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); N-butylamine In benzene Ambient temperature; | 91% |
trans-1,2-dichloroethylene
diphenylphosphane
trans-1,2-bis(diphenylphosphino)ethylene
Conditions | Yield |
---|---|
With triethylamine; bis(triphenylphosphine)nickel(II) chloride In N,N-dimethyl-formamide at 120℃; for 7h; | 91% |
With potassium hydroxide In dimethyl sulfoxide at 60℃; for 1h; | 68.5% |
trans-1,2-dichloroethylene
1-octyn-3-ol
(S)-(E)-1-chlorodec-1-en-3-yn-5-ol
Conditions | Yield |
---|---|
With piperidine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In benzene at 20℃; for 3h; cross-coupling; | 91% |
Stage #1: trans-1,2-dichloroethylene With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In benzene at 20℃; for 0.05h; Schlenk technique; Inert atmosphere; Stage #2: 1-octyn-3-ol With triethylamine at 20℃; Schlenk technique; Inert atmosphere; | 85% |
With piperidine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In benzene at 0 - 20℃; for 6h; Inert atmosphere; | 85% |
Conditions | Yield |
---|---|
With piperidine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 20℃; | 91% |
trans-1,2-dichloroethylene
trimethylsilyl trifluoromethanesulfonate
benzaldehyde
1-phenyl-3-trimethylsilylprop-2-yn-1-ol
Conditions | Yield |
---|---|
Stage #1: trans-1,2-dichloroethylene With n-butyllithium In tetrahydrofuran; hexane at 0℃; Stage #2: benzaldehyde In tetrahydrofuran; hexane at 0℃; Stage #3: trimethylsilyl trifluoromethanesulfonate Further stages; | 91% |
trans-1,2-dichloroethylene
anthracene
trans-7,8-dichloro-2,3:5,6-dibenzobicyclo<2.2.2>octa-2,5-diene
Conditions | Yield |
---|---|
at 215℃; for 30h; | 90% |
at 198 - 202℃; |
trans-1,2-dichloroethylene
Bicyclo [5.3.1]undec-10-en-9-one
(1S,4S,7S)-2,3-Dichloro-tricyclo[5.5.1.01,4]tridecan-5-one
Conditions | Yield |
---|---|
for 19h; Irradiation; | 90% |
IUPAC Name: (E)-1,2-Dichloroethene
Molecular Weight: 96.94328 g/mol
Molecular Formula: C2H2Cl2
Density: 1.243 g/cm3
Melting Point: −57 °C(lit.)
Boiling Point: 47.7 °C at 760 mmHg
Flash Point: 6.1 °C
Index of Refraction: 1.453
Molar Refractivity: 21.07 cm3
Molar Volume: 77.9 cm3
Surface Tension: 25.9 dyne/cm
Enthalpy of Vaporization: 27.93 kJ/mol
Vapour Pressure: 333 mmHg at 25 °C
Exact Mass: 95.953355
EINECS: 205-860-2
Properties: colourless liquid
Product categories: Organics ; Analytical Chemistry ; Standard Solution of Volatile Organic Compounds for Water , Soil Analysis ; Standard Solutions (VOC) ; Alpha Sort ; D ; DAlphabetic ; DIA - DIC ; Volatiles/ Semivolatiles
Mmolecular structure of trans-1,2-Dichloroethylene (CAS NO.156-60-5):
1. | skn-rbt 500 mg/24H MOD | JACTDZ Journal of the American College of Toxicology. 1 (1990),11. | ||
2. | eye-rbt 10 mg MOD | JACTDZ Journal of the American College of Toxicology. 1 (1990),11. | ||
3. | mma-smc 80 mmol/L | TCMUD8 Teratogenesis, Carcinogenesis, and Mutagenesis. 4 (1984),365. | ||
4. | ihl-rat TCLo:12,000 ppm/6H (female 7-16D post):REP | FAATDF Fundamental and Applied Toxicology. 20 (1993),225. | ||
5. | ihl-hmn TCLo:4800 mg/m3/10M:CNS | AHBAAM Archiv fuer Hygiene und Bakteriologie. 116 (1936),131. | ||
6. | orl-rat LD50:1235 mg/kg | TXCYAC Toxicology. 7 (1977),141. | ||
7. | ipr-rat LD50:7411 mg/kg | TXCYAC Toxicology. 7 (1977),141. | ||
8. | orl-mus LD50:2122 mg/kg | DCTODJ Drug and Chemical Toxicology. 8 (1985),373. | ||
9. | ipr-rat LD50:7536 mg/kg | TXCYAC Toxicology. 7 (2)(1977),141. | ||
10. | ihl-mus LCLo:75,000 mg/m3/2H | AHBAAM Archiv fuer Hygiene und Bakteriologie. 116 (1936),131. | ||
11. |
|
Reported in EPA TSCA Inventory.
Moderately toxic by ingestion. Mildly toxic by inhalation. Human systemic effects by inhalation: sleep, hallucinations, and distorted perceptions. Experimental reproductive effects. A skin and eye irritant. Mutation data reported. Exposure to high vapor concentration can cause nausea, vomiting, weakness, tremor, and cramps. Recovery is usually prompt following removal from exposure. Dermatitis may result from defatting action on skin. Dangerous fire hazard when exposed to heat, flame, or oxidizers. Moderate explosion hazard in the form of vapor when exposed to flame. Violent reaction with difluoromethylene dihypofluorite. Forms shock-sensitive explosive mixtures with dinitrogen tetraoxide. Reaction with solid caustic alkalies or their concentrated solutions produces chloracetylene gas that ignites spontaneously in air. Reacts violently with N2O4, KOH, Na, NaOH. Moderate explosion hazard in the form of vapor when exposed to flame. Can react vigorously with oxidizing materials. To fight fire, use water spray, foam, CO2, dry chemical. When heated to decomposition it emits toxic fumes of Cl−. See also CHLORIDES; CHLORINATED HYDROCARBONS, ALIPHATIC; and ACETYLENE COMPOUNDS and ALKYNES.
Hazard Codes: F, Xn, T
Risk Statements: 11-20-52/53-39/23/24/25-23/24/25
R11: Highly flammable.
R20: Harmful by inhalation.
R52/53: Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
R39: Danger of very serious irreversible effects.
R23/24/25: Toxic by inhalation, in contact with skin and if swallowed.
Safety Statements: 7-16-29-61-45-36/37
S7: Keep container tightly closed.
S16: Keep away from sources of ignition.
S29: Do not empty into drains.
S61: Avoid release to the environment. Refer to special instructions / safety data sheets.
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S36/37: Wear suitable protective clothing and gloves.
RIDADR: UN 1150 3/PG 2
WGK Germany: 2
RTECS: KV9400000
HazardClass: 3
PackingGroup: II
DFG MAK: 200 ppm (800 mg/m3)
The chemical synonyms of trans-1,2-Dichloroethylene (CAS NO.156-60-5) are (E)-1,2-Dichloroethene ; (E)-1,2-Dichloroethylene ; 4-01-00-00709 (Beilstein Handbook Reference) ; AI3-28786 ; BRN 1420761 ; CCRIS 2505 ; Ethylene, 1,2-dichloro-, trans- ; HCC 1130t ; HSDB 6361 ; NSC 60512 ; R 1130t ; RCRA waste number U079 ; trans-Acetylene dichloride ; trans-Dichloroethylene . It is highly flammable. Oxidizes in air to form unstable peroxides that may explode spontaneously. Avoid contact with copper and copper alloys. trans-1,2-Dichloroethylene reacts with alkalis, difluoromethylene, dihypofluorite, and nitrogen tetraoxide. Contact with solid alkalis or their concentrated solutions will cause formation of chloroacetylene, which ignites in air. Corrosive to metals unless an inhibitor has been added. Oxidation in the presence of concentrated sulfuric acid or a free radical initiator gives chloroacetyl chloride via epoxide intermediates. It is incompatible with organic peroxides.
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