Conditions | Yield |
---|---|
With 1,2,3-Benzotriazole; thionyl chloride In dichloromethane at 20℃; Substitution; | 94% |
With thionyl chloride at 20℃; for 16h; Cooling with ice; | 84% |
With thionyl chloride at 20℃; for 16.66h; Cooling with ice; Inert atmosphere; | 84% |
(Z)-but-2-ene-1,4-diyl dimethanesulfonate
Z-1,4-dichlorobutene
Conditions | Yield |
---|---|
With calcium chloride In dimethyl sulfoxide for 3h; Ambient temperature; | 60% |
Conditions | Yield |
---|---|
With thionyl chloride; zinc(II) chloride at 80 - 85℃; | |
With hydrogenchloride at 90℃; for 4h; | 4.2 g |
buta-1,3-diene
A
Z-1,4-dichlorobutene
B
trans-1,4-dichlorobut-2-ene
C
3,4-dichlorobut-1-ene
Conditions | Yield |
---|---|
With iodine; copper dichloride In benzene at 70℃; for 2h; | |
With copper dichloride In acetonitrile at 60℃; for 2h; |
Conditions | Yield |
---|---|
at 99.9℃; Kinetics; Thermodynamic data; Equilibrium constant; activation parameters; |
Conditions | Yield |
---|---|
With borane; acetic acid Product distribution; multistep reaction, stereospecificity, various alkenes; |
3,4-dichlorobut-1-ene
A
Z-1,4-dichlorobutene
B
trans-1,4-dichlorobut-2-ene
Conditions | Yield |
---|---|
With poly(p-xylylene); palladium In toluene at 99.85℃; Product distribution; | |
With oxygen at 100℃; |
2,5-dihydrofuran
thionyl chloride
(E)-3-Ureido-but-2-enoic acid ethyl ester
Z-1,4-dichlorobutene
Conditions | Yield |
---|---|
at 40℃; |
Z-1,4-dichlorobutene
hexamethylenetetramine
1-<(Z)-4-Chloro-2-butenyl>-1-azonia-3,5,7-triazatricyclo<3.3.1.1.3,7>decane chloride
Conditions | Yield |
---|---|
In dichloromethane for 5h; Reflux; Large scale reaction; | 100% |
In ethanol; chloroform for 4h; Heating; | 99% |
In chloroform at 60℃; for 4h; | 94% |
In chloroform for 4h; Heating; | 91% |
In chloroform for 4h; Reflux; | 91% |
Z-1,4-dichlorobutene
triethyl 5-chloro-cis-pent-3-ene-1,1,1-tricarboxylate
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide; toluene at 80℃; Alkylation; | 100% |
Z-1,4-dichlorobutene
1-(benzenesulfonyl)-2,5-dihydro-1H-pyrrole
Conditions | Yield |
---|---|
Stage #1: benzenesulfonamide With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #2: Z-1,4-dichlorobutene In N,N-dimethyl-formamide at 20℃; for 20h; | 100% |
Z-1,4-dichlorobutene
phenylsulfenyl bromide
(2-Bromo-3-chloro-1-chloromethyl-propylsulfanyl)-benzene
Conditions | Yield |
---|---|
In dichloromethane for 9h; Ambient temperature; | 99% |
Z-1,4-dichlorobutene
malonic acid dimethyl ester
Dimethyl 3-cyclopentene-1,1-dicarboxylate
Conditions | Yield |
---|---|
Stage #1: malonic acid dimethyl ester With lithium hydride In N,N-dimethyl-formamide at 0℃; for 4h; Stage #2: Z-1,4-dichlorobutene In N,N-dimethyl-formamide at 0 - 20℃; | 99% |
Stage #1: malonic acid dimethyl ester With lithium hydride In N,N-dimethyl-formamide at 0℃; for 2h; Inert atmosphere; Stage #2: Z-1,4-dichlorobutene In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere; | 87% |
Stage #1: malonic acid dimethyl ester With lithium hydride In N,N-dimethyl-formamide at 0℃; for 2h; Stage #2: Z-1,4-dichlorobutene In N,N-dimethyl-formamide at 0 - 25℃; for 72h; | 84% |
Z-1,4-dichlorobutene
N1,N4-bis(mesitylenesulfonyl)-N4-ethyl-1,4-diaminobutane
N3,N8-bis(mesitylenesulfonyl)-12-chloro-3,8-diaza-(10Z)-dodecane
Conditions | Yield |
---|---|
Stage #1: N1,N4-bis(mesitylenesulfonyl)-N4-ethyl-1,4-diaminobutane With sodium hydride In N,N-dimethyl-formamide at 20℃; for 2h; Stage #2: Z-1,4-dichlorobutene In N,N-dimethyl-formamide at 50℃; for 18h; Further stages.; | 99% |
Conditions | Yield |
---|---|
Stage #1: phenol With potassium hydroxide In ethanol for 0.5h; Schlenk technique; Inert atmosphere; Reflux; Stage #2: Z-1,4-dichlorobutene In ethanol at 0 - 20℃; Schlenk technique; Inert atmosphere; Reflux; | 98% |
Stage #1: phenol With potassium hydroxide In ethanol for 0.25h; Heating; Stage #2: Z-1,4-dichlorobutene at 20℃; for 15h; | 75% |
(i) NaOH, MeOH, (ii) /BRN= 1719692/; Multistep reaction; |
Z-1,4-dichlorobutene
(2R)-2,5-dihydro-2-isopropyl-3,6-dimethoxypyrazine
(Z)-1,4-bis((2S,5R)-5-isopropyl-3,6-dimethoxy-2,5-dihydropyrazin-2-yl)but-2-ene
Conditions | Yield |
---|---|
Stage #1: (2R)-2,5-dihydro-2-isopropyl-3,6-dimethoxypyrazine With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere; Stage #2: Z-1,4-dichlorobutene In tetrahydrofuran at 20℃; for 10h; Inert atmosphere; | 97.5% |
Z-1,4-dichlorobutene
N1,N4-bis(mesitylenesulfonyl)-N4-ethyl-1,4-diamino-2-butene
N3,N8-bis(mesitylenesulfonyl)-12-chloro-3,8-diaza-(5Z,10Z)-dodecadiene
Conditions | Yield |
---|---|
Stage #1: N1,N4-bis(mesitylenesulfonyl)-N4-ethyl-1,4-diamino-2-butene With sodium hydride In N,N-dimethyl-formamide at 20℃; for 2h; Stage #2: Z-1,4-dichlorobutene In N,N-dimethyl-formamide at 50℃; for 18h; Further stages.; | 97% |
Z-1,4-dichlorobutene
N,N'-(1,2-phenylene)bis(4-methoxybenzenesulfonamide)
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile for 24h; Reflux; | 97% |
Z-1,4-dichlorobutene
bis(phenylsulfonyl)methane
1,1-bis(phenylsulfonyl)-3-cyclopentene
Conditions | Yield |
---|---|
With sodium hydroxide; tetrabutyl ammonium fluoride In toluene for 20h; Ambient temperature; | 96% |
Z-1,4-dichlorobutene
(2Z)-4-chloro-2-butenyl 2-hydroxy-1-naphthoate
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 25℃; for 17h; | 95% |
Conditions | Yield |
---|---|
In tetrahydrofuran for 24h; Ambient temperature; | 95% |
4-nitro-phenol
Z-1,4-dichlorobutene
(Z)-1,4-bis(4-nitrophenoxy)but-2-ene
Conditions | Yield |
---|---|
Stage #1: 4-nitro-phenol With potassium hydroxide; 18-crown-6 ether In acetone for 0.25h; Heating; Stage #2: Z-1,4-dichlorobutene for 24h; Heating; | 95% |
Z-1,4-dichlorobutene
Conditions | Yield |
---|---|
With potassium carbonate In ethanol (under Ar); addn. of K2CO3 and the dihalogenide to a soln. of the Pd complex in EtOH, stirring at room temp. for 12 h; filtn., washing the ppt. with EtOH, evapn. of the solvent under vac. at 40°C, recrystn. from EtOH at -20°C; | 95% |
Z-1,4-dichlorobutene
(11aS)-8-hydroxy-7-methoxy-1,2,3,11a-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one
Conditions | Yield |
---|---|
Stage #1: (11aS)-8-hydroxy-7-methoxy-1,2,3,11a-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one With potassium carbonate In butanone for 0.5h; Stage #2: Z-1,4-dichlorobutene In butanone for 4h; Reflux; | 95% |
Z-1,4-dichlorobutene
4-cyanomethyl-2-cyclopentyloxy-1-methoxybenzene
1-[3-(cyclopentyloxy)-4-methoxyphenyl]cyclopen-3-ene-1-carbonitrile
Conditions | Yield |
---|---|
Stage #1: 4-cyanomethyl-2-cyclopentyloxy-1-methoxybenzene With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 1h; Stage #2: Z-1,4-dichlorobutene In tetrahydrofuran at -78℃; for 1.5h; | 94% |
With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; | 73% |
Conditions | Yield |
---|---|
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane for 12h; Heating; | 93% |
Z-1,4-dichlorobutene
2-(3-(benzyloxy)-4-methoxyphenyl)acetonitrile
1-(3-benzyloxy-4-methoxyphenyl)cyclopen-3-ene-1-carbonitrile
Conditions | Yield |
---|---|
Stage #1: 2-(3-(benzyloxy)-4-methoxyphenyl)acetonitrile With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 1h; Stage #2: Z-1,4-dichlorobutene In tetrahydrofuran at -78℃; for 1.5h; | 93% |
Z-1,4-dichlorobutene
trifluoromethyl hypochlorite
1,2,4-Trichloro-3-trifluoromethoxy-butane
Conditions | Yield |
---|---|
In trichlorofluoromethane at -111 - 22℃; for 20h; | 92% |
Z-1,4-dichlorobutene
dimethyl 2-oxocyclopentane-1,3-dicarboxylate
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 70℃; for 24h; | 92% |
3-methylbenzyl cyanide
Z-1,4-dichlorobutene
1-m-tolyl-cyclopent-3-enecarbonitrile
Conditions | Yield |
---|---|
Stage #1: 3-methylbenzyl cyanide With sodium t-butanolate In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 0℃; for 0.5h; Inert atmosphere; Stage #2: Z-1,4-dichlorobutene In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 0 - 20℃; for 3h; Inert atmosphere; | 92% |
Conditions | Yield |
---|---|
In toluene at 110℃; for 48h; Substitution; | 91% |
Z-1,4-dichlorobutene
3-bromo-6-methylindolo<2,3-a>pyrrolo<3,4-c>carbazole-5,7-(6H)dione
Conditions | Yield |
---|---|
With caesium carbonate In N,N-dimethyl-formamide at 60℃; for 18h; | 91% |
Z-1,4-dichlorobutene
2-(2-bromophenyl)acetonitrile
Conditions | Yield |
---|---|
With 1-methyl-pyrrolidin-2-one; sodium t-butanolate In tetrahydrofuran at -10 - 20℃; | 91% |
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 40℃; for 5h; | 90% |
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 40℃; for 5h; | 90% |
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 40℃; for 5h; | 90% |
Z-1,4-dichlorobutene
[4-(3-Methyl-benzyloxy)-phenyl]-carbamic acid ethyl ester
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 40℃; for 5h; | 90% |
IUPAC Name: (Z)-1,4-Dichlorobut-2-ene
Synonyms : Cis-1,4-Dichloro-2-butene ; (2Z)-1,4-Dichloro-2-butene ; (2Z)-1,4-Dichlorobut-2-ene ; 2-Butene, 1,4-dichloro- ; 2-Butene, 1,4-dichloro-, (2Z)-
Molecular formula: C4H6Cl2
Molecular weight: 125.00
CAS NO: 1476-11-5
EINECS: 216-021-5
Index of Refraction: 1.459
Surface Tension: 28 dyne/cm
Molar Refractivity: 30.33 cm3
Molar Volume: 110.9 cm3
Density: 1.126 g/cm3
Flash Point: 54.4 °C
Enthalpy of Vaporization: 37.61 kJ/mol
Boiling Point: 155.5 °C at 760 mmHg
Vapour Pressure: 3.89 mmHg at 25 °C
Melting point : -48 ºC
Storage temp: 2-8 °C
Apperance of cis-1,4-Dichloro-2-butene (CAS NO.1476-11-5): Light-Yellow Clear Liquid
cis-1,4-Dichloro-2-butene (CAS NO.1476-11-5) is used for pyrophendane synthesis.
Hazard Codes:T+N
Risk Statements: 45-24-25-26-34-50/53
R45:May cause cancer.
R24:Toxic in contact with skin.
R25 :Toxic if swallowed.
R26:Very toxic by inhalation.
R34:Causes burns.
R50/53:Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
Safety Statements: 53-26-28-36/37/39-45-60-61
S53:Avoid exposure - obtain special instructions before use.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S28:After contact with skin, wash immediately with plenty of soap-suds.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S60:This material and its container must be disposed of as hazardous waste.
S61:Avoid release to the environment. Refer to special instructions / safety data sheets.
RIDADR: UN 3390 6.1/PG 1
WGK Germany: 3
RTECS: EM4900000
F: 8-21
HazardClass: 8
PackingGroup of cis-1,4-Dichloro-2-butene (CAS NO.1476-11-5): I
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