(E)-1,4-Dibromobut-2-ene supplier

Name
(E)-1,4-Dibromobut-2-ene
EINECS 212-472-7
CAS No. 821-06-7
Article Data28
CAS DataBase
Density 1.867 g/cm³
Solubility slightly soluble in water
Melting Point 48-51 °C(lit.)
Formula C₄H₆Br₂
Boiling Point 203 °C at 760 mmHg
Molecular Weight 213.9
Flash Point 71.9 °C
Transport Information UN 2923 8/PG 2
Appearance white to light yellow crystal powder
Safety 26-36/37/39-45-28A
Risk Codes 34-23/25
Molecular Structure
Hazard Symbols
Synonyms 2-Butene,1,4-dibromo-, (E)- (8CI);2-Butene, 1,4-dibromo-, trans- (4CI);(2E)-1,4-Dibromo-2-butene;(E)-1,4-Dibromo-2-butene;1,4-Dibromo-(E)-2-butene;1,4-Dibromo-2-(E)-butene;1,4-Dibromo-trans-2-butene;trans-1,4-Dibromo-2-butene;(2E)-1,4-dibromobut-2-ene;
PSA 0.00000
LogP 2.33240

Synthetic route

: 106-99-0
buta-1,3-diene

: 821-06-7
(E)-1,4-dibromobutene

Conditions

Conditions	Yield
With bromine In chloroform at -78 - 23℃;	100%
With bromine In tetrachloromethane at -78 - 20℃; for 16h;	58%
With bromine In tetrachloromethane at -78 - 20℃; for 16h;	58%

: 106-95-6
allyl bromide

A: 18866-73-4
cis-1,4-dibromo-2-butene

B: 821-06-7
(E)-1,4-dibromobutene

C: 74-85-1
ethene

Conditions

Conditions	Yield
With Hoveyda-Grubbs catalyst second generation In acetone at 25℃; for 1h; Grubbs Olefin Metathesis; Flow reactor; Overall yield = > 95 %;	A n/a B 95% C n/a

...Expand

: 821-11-4
(E)-2-butene-1,4-diol

: 821-06-7
(E)-1,4-dibromobutene

Conditions

Conditions	Yield
With phosphorus tribromide	65%

: 78-76-2, 5787-31-5
s-butyl bromide

A: 4784-77-4, 29576-14-5, 39616-19-8
(E/Z)-crotyl bromide

B: 5408-86-6
2,3-dibromobutane

C: 821-06-7
(E)-1,4-dibromobutene

D: 50341-35-0
2,2-dibromobutane

Conditions

Conditions	Yield
With hydrogen bromide; bromine at 100℃; under 80 Torr; for 0.25h; Heating; Irradiation; Further byproducts given;	A 8.5% B 6.3% C 39.7% D 22.5%
With bromine at 100℃; under 80 Torr; for 0.25h; Heating; Irradiation; Further byproducts given;	A 20.3% B 3.9% C 31% D 34.6%

...Expand

: 78-76-2, 5787-31-5
s-butyl bromide

A: 4784-77-4, 29576-14-5, 39616-19-8
(E/Z)-crotyl bromide

B: 821-06-7
(E)-1,4-dibromobutene

C: 50341-35-0
2,2-dibromobutane

D: 107-80-2
1,3-dibromobutane

Conditions

Conditions	Yield
With hydrogen bromide; bromine at 100℃; under 80 Torr; for 0.25h; Heating; Irradiation; Further byproducts given;	A 14.6% B 39.1% C 21.6% D 2.5%

...Expand

: 6081-86-3
pyridine perbromide

: 106-99-0
buta-1,3-diene

A: 821-06-7
(E)-1,4-dibromobutene

B: 10463-48-6
3,4-dibromo-1-butene

C: 76665-61-7
N-(4-bromo-1-buten-3-yl)pyridinium bromide

Conditions

Conditions	Yield
In 1,2-dichloro-ethane at 20℃; for 0.5h; Yields of byproduct given;	A n/a B n/a C 35%

...Expand

: 78-76-2, 5787-31-5
s-butyl bromide

A: 5408-86-6
2,3-dibromobutane

B: 821-06-7
(E)-1,4-dibromobutene

C: 50341-35-0
2,2-dibromobutane

D: 1529-68-6
1,2,3,4-tetrabromobutane

Conditions

Conditions	Yield
With bromine at 100℃; under 80 Torr; for 0.25h; Heating; Irradiation; Further byproducts given;	A 10.2% B 24% C 24% D 9%

...Expand

: 78-76-2, 5787-31-5
s-butyl bromide

A: 5408-86-6
2,3-dibromobutane

B: 821-06-7
(E)-1,4-dibromobutene

C: 50341-35-0
2,2-dibromobutane

D: 632-05-3
1,2,3-tribromobutane

Conditions

Conditions	Yield
With hydrogen bromide; bromine at 100℃; under 80 Torr; for 0.25h; Heating; Irradiation; Further byproducts given;	A 13.7% B 19.2% C 23.8% D 12.5%

...Expand

: 106-95-6
allyl bromide

: 821-06-7
(E)-1,4-dibromobutene

Conditions

Conditions	Yield
With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane for 0.183333h; Inert atmosphere;	15%

: 124-18-5
decane

: 10463-48-6
3,4-dibromo-1-butene

: 821-06-7
(E)-1,4-dibromobutene

Conditions

Conditions	Yield
at 61 - 100℃; Kinetics;
at 61 - 100℃; Mechanism;

: 18866-73-4
cis-1,4-dibromo-2-butene

: 821-06-7
(E)-1,4-dibromobutene

Conditions

Conditions	Yield
in der Waerme;
at 120℃;

: 10463-48-6
3,4-dibromo-1-butene

: 821-06-7
(E)-1,4-dibromobutene

Conditions

Conditions	Yield
at 85 - 90℃;

: 106-99-0
buta-1,3-diene

A: 6974-12-5
1,4-dibromo-2-butene

B: 821-06-7
(E)-1,4-dibromobutene

Conditions

Conditions	Yield
With bromine liquid 1,4-dibromo-butene-(2);
With chloroform; bromine

: 106-99-0
buta-1,3-diene

A: 821-06-7
(E)-1,4-dibromobutene

B: 10463-48-6
3,4-dibromo-1-butene

Conditions

Conditions	Yield
With bromine In 1,2-dichloro-ethane at 25℃; for 0.333333h; Mechanism; Product distribution; Rate constant; other solvent and other brominating agent;
With hexane; bromine at -30 - -15℃;

: 821-11-4, 6117-80-2, 110-64-5
1,4-butenediol

A: 18866-73-4
cis-1,4-dibromo-2-butene

B: 821-06-7
(E)-1,4-dibromobutene

Conditions

Conditions	Yield
With phosphorus tribromide In tetrachloromethane

: 110-86-1
pyridine

: 106-99-0
buta-1,3-diene

A: 821-06-7
(E)-1,4-dibromobutene

B: 10463-48-6
3,4-dibromo-1-butene

C: 76665-61-7
N-(4-bromo-1-buten-3-yl)pyridinium bromide

Conditions

Conditions	Yield
With bromine In 1,2-dichloro-ethane at 25℃; for 0.5h; Mechanism; Product distribution; Rate constant; other solvent, other brominating agent;

...Expand

: 7726-95-6
bromine

: 106-99-0
buta-1,3-diene

: 821-06-7
(E)-1,4-dibromobutene

Conditions

Conditions	Yield
in der Gasphase bei Verduennung mit Stickstoff;

: 67-66-3
chloroform

: 7726-95-6
bromine

: 106-99-0
buta-1,3-diene

: 821-06-7
(E)-1,4-dibromobutene

Conditions

Conditions	Yield
at -30 - -15℃;

...Expand

: 75-15-0
carbon disulfide

: 7726-95-6
bromine

: 106-99-0
buta-1,3-diene

A: 821-06-7
(E)-1,4-dibromobutene

B: 10463-48-6
3,4-dibromo-1-butene

Conditions

Conditions	Yield
das Mengenverhaeltnis der Reaktionsprodukte ist vom Loesungsmittel unabhaengig;

...Expand

: 56-23-5
tetrachloromethane

: 7726-95-6
bromine

: 106-99-0
buta-1,3-diene

A: 821-06-7
(E)-1,4-dibromobutene

B: 10463-48-6
3,4-dibromo-1-butene

Conditions

Conditions	Yield
das Mengenverhaeltnis der Reaktionsprodukte ist vom Loesungsmittel unabhaengig;

...Expand

: 110-54-3
hexane

: 7726-95-6
bromine

: 106-99-0
buta-1,3-diene

A: 821-06-7
(E)-1,4-dibromobutene

B: 10463-48-6
3,4-dibromo-1-butene

Conditions

Conditions	Yield
das Mengenverhaeltnis der Reaktionsprodukte ist vom Loesungsmittel unabhaengig;

...Expand

: 67-66-3
chloroform

: 7726-95-6
bromine

: 106-99-0
buta-1,3-diene

A: 821-06-7
(E)-1,4-dibromobutene

B: 10463-48-6
3,4-dibromo-1-butene

Conditions

Conditions	Yield
das Mengenverhaeltnis der Reaktionsprodukte ist vom Loesungsmittel unabhaengig;

...Expand

: 79-01-6
Trichloroethylene

: 7726-95-6
bromine

: 106-99-0
buta-1,3-diene

A: 821-06-7
(E)-1,4-dibromobutene

B: 10463-48-6
3,4-dibromo-1-butene

Conditions

Conditions	Yield
das Mengenverhaeltnis der Reaktionsprodukte ist vom Loesungsmittel unabhaengig;

...Expand

: 344397-18-8
cis-butene-1,4-diol

: 821-06-7
(E)-1,4-dibromobutene

Conditions

Conditions	Yield
With pyridine; phosphorus tribromide; iodine In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; dichloromethane

: 106-95-6
allyl bromide

A: 18866-73-4
cis-1,4-dibromo-2-butene

B: 821-06-7
(E)-1,4-dibromobutene

Conditions

Conditions	Yield
With Hoveyda-Grubbs catalyst second generation In dichloromethane Inert atmosphere; Overall yield = 15 percent; Overall yield = 1.7 g;	A n/a B n/a

: 103-83-3
N,N'-dimethylbenzylamine

: 821-06-7
(E)-1,4-dibromobutene

: 100186-76-3
C22H32N2(2+)*2Br(1-)

Conditions

Conditions	Yield
In acetonitrile for 0.5h; Heating;	100%

: 23003-22-7
3-hydroxypyridine-2-thione

: 821-06-7
(E)-1,4-dibromobutene

: 3-hydroxy-2-(4-bromo-2-buten-1-ylthio)pyridine hydrobromide

Conditions

Conditions	Yield
In acetone at 20℃; for 20h;	100%

: 821-06-7
(E)-1,4-dibromobutene

: 1187455-33-9
(S)-3-((2-hydroxynaphthalen-1-yl)methyleneamino)-4-isopropyl-2-oxazolidinone

: 1187455-06-6
(S)-3-(((2-(E)-4-bromobut-2-enyloxy)naphthalen-1-yl)methyleneamino)-4-isopropyl-2-oxazolidinone

Conditions

Conditions	Yield
With potassium carbonate In acetone at 20℃; for 10h; Inert atmosphere;	100%

: 821-06-7
(E)-1,4-dibromobutene

: 1187455-34-0
(R)-3-((2-hydroxynaphthalen-1-yl)methyleneamino)-4-isopropyl-2-oxazolidinone

: 1187455-07-7
(R)-3-(((2-(E)-4-bromobut-2-enyloxy)naphthalen-1-yl)methyleneamino)-4-isopropyl-2-oxazolidinone

Conditions

Conditions	Yield
With potassium carbonate In acetone at 20℃; for 10h; Inert atmosphere;	100%

: 17252-51-6
1,3-di(4-pyridyl)propane

: 821-06-7
(E)-1,4-dibromobutene

: C30H34N4(2+)*2Br(1-)

Conditions

Conditions	Yield
In acetone at 20℃;	100%

: 821-06-7
(E)-1,4-dibromobutene

: 123-54-6
acetylacetone

: 75822-61-6, 115580-34-2
1-(2-methyl-5-vinyl-4,5-dihydrofuran-3-yl)ethan-1-one

Conditions

Conditions	Yield
Stage #1: acetylacetone With caesium carbonate In dimethyl sulfoxide at 20℃; for 0.333333h; Claisen Rearrangement; Inert atmosphere; Stage #2: (E)-1,4-dibromobutene In dimethyl sulfoxide at 100℃; for 12h; Inert atmosphere;	100%

: 821-06-7
(E)-1,4-dibromobutene

: 1‐octyl‐1,4‐diazabicyclo[2.2.2]octan‐1‐ium bromide

: C32H64N4(4+)*4Br(1-)

Conditions

Conditions	Yield
In N,N-dimethyl-formamide for 48h; Heating;	100%

: 821-06-7
(E)-1,4-dibromobutene

: 4271-27-6
diethyllaurylamine

: 100186-80-9, 110282-54-7
C36H76N2(2+)*2Br(1-)

Conditions

Conditions	Yield
In acetonitrile for 0.5h; Heating;	99%

: 821-06-7
(E)-1,4-dibromobutene

: 335004-12-1
N-(tert-butyloxycarbonyl)(2,4,6-triisopropylphenyl)sulfonamide

: 335004-20-1
(E)-N,N'-bis(tert-butyloxycarbonyl)-N,N'-bis[(2,4,6-triisopropylphenyl)sulfonyl]-2-butene-1,4-diamine

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile Heating;	99%

: 821-06-7
(E)-1,4-dibromobutene

: 122-52-1
triethyl phosphite

: 1112-96-5, 16626-80-5, 56727-14-1
tetraethyl (E)-2-butene-1,4-diphosphonate

Conditions

Conditions	Yield
for 5h; Reflux;	99%
for 5h; Reflux;	99%
Arbuzov reaction;

: 3978-81-2
4-tert-butylpyridine

: 821-06-7
(E)-1,4-dibromobutene

: 1,4-bis(4-tert-butylpyridinium)-but-(2E)-ene-1,4-diyl dibromide

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 70℃;	99%
In N,N-dimethyl-formamide at 70℃;	66%

: 821-06-7
(E)-1,4-dibromobutene

: 112-69-6
N,N-dimethylhexadecylamine

: 87673-96-9, 94941-64-7, 94941-68-1
C40H84N2(2+)*2Br(1-)

Conditions

Conditions	Yield
In acetonitrile for 0.5h; Heating;	98%

: 821-06-7
(E)-1,4-dibromobutene

: 124603-50-5, 124603-57-2
trans-6-(4-methylphenylsulfonyl)amino-4-methyl-1-triisopropyl-silyl(oxy)-cyclohex-1-ene

: E-6-N,N'-<(4-methylphenylsulfonyl)-(4-bromo-2-butene)>amino-4-methyl-1-triisopropylsilyl(oxy)-cyclohex-1-ene

Conditions

Conditions	Yield
With sodium hydride In tetrahydrofuran for 1h; Heating;	98%

: 696-54-8
pyridine-4-aldoxime

: 821-06-7
(E)-1,4-dibromobutene

: (E)-1-(4-bromobut-2-enyl)-4-((hydroxyimino)methyl)pyridinium bromide

Conditions

Conditions	Yield
In chloroform for 3h; Inert atmosphere; Reflux;	98%
In acetone for 1.5h; Heating;	95%
In acetone for 2h; Heating;	95%
In acetone for 2h; Reflux;	95%

: 584-13-4
4-amino-1,2,4-triazole

: 821-06-7
(E)-1,4-dibromobutene

: trans-1,4-di(4-amino-1,2,4-triazolium-1N)-2-butene dibromide

Conditions

Conditions	Yield
In acetonitrile for 6.5h; Reflux;	98%
In acetonitrile for 6.5h; Reflux;	98%

: N-(tert-butyloxycarbonyl)-3,4-bis(dodecyloxy)benzenesulfonamide

: 821-06-7
(E)-1,4-dibromobutene

: 1453119-87-3
C74H130N2O12S2

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile	98%

: 821-06-7
(E)-1,4-dibromobutene

: 767-00-0
4-cyanophenol

: 101716-60-3
(E)-4,4'-(but-2-ene-1,4-diylbis(oxy))dibenzonitrile

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile Reflux;	97%
With sodium ethanolate

: 821-06-7
(E)-1,4-dibromobutene

: 5675-43-4
Di-n-butyl-hexadecylamin

: 100200-26-8, 110282-57-0
C52H108N2(2+)*2Br(1-)

Conditions

Conditions	Yield
In acetonitrile for 0.5h; Heating;	97%

: 821-06-7
(E)-1,4-dibromobutene

: 1193-92-6
3-pyridinealdoxime

: (E)-1,4-bis(3-hydroxyiminomethylpyridinium)but-2-ene dibromide

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 100℃; for 2h;	97%

: 821-06-7
(E)-1,4-dibromobutene

: 7651-02-7
stearamidopropyl dimethylamine

: C50H102N4O2(2+)*2Br(1-)

Conditions

Conditions	Yield
With sodium hydroxide In isopropyl alcohol at 80℃; for 24h;	96.1%

: 821-06-7
(E)-1,4-dibromobutene

: 110452-14-7
2-phenylthiocyclohexanone

: (2S,3aR)-3a-Phenylsulfanyl-2-vinyl-2,3,3a,4,5,6-hexahydro-benzofuran

Conditions

Conditions	Yield
With potassium hydride In tetrahydrofuran Ambient temperature;	96%

: 821-06-7
(E)-1,4-dibromobutene

: N-(tert-butyloxycarbonyl)(2-thienyl)sulfonamide

: 335004-26-7
(E)-N,N'-bis(tert-butyloxycarbonyl)-N,N'-bis[(2-thienyl)sulfonyl]-2-butene-1,4-diamine

Conditions

Conditions	Yield
With potassium carbonate	96%

: 696-54-8
pyridine-4-aldoxime

: 821-06-7
(E)-1,4-dibromobutene

: (E)-1-(2-hydroxyiminomethylpyridinium)-4-(4-hydroxyiminomethylpyridinium)-but-2-ene dibrobide

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 100℃; for 4h;	96%
In N,N-dimethyl-formamide at 70℃;	95%
In N,N-dimethyl-formamide at 100℃; for 1.5h;	93%

: 821-06-7
(E)-1,4-dibromobutene

: 1453-82-3
isonicotinamide

: (E)-1-(4-bromobut-2-enyl)-4-carbamoylpyridinium bromide

Conditions

Conditions	Yield
In acetonitrile for 3h; Inert atmosphere; Reflux;	96%
In acetone for 2h; Heating;	93%
In acetone for 2h; Reflux;	93%

: 821-06-7
(E)-1,4-dibromobutene

: C4H6O6S2(2-)*2Na(1+)

Conditions

Conditions	Yield
With sodium sulfite In water; N,N-dimethyl-formamide at 100℃; for 11h;	96%
With sodium sulfite In water at 105 - 115℃;

: 7378-99-6
N,N-dimethyloctanamide

: 821-06-7
(E)-1,4-dibromobutene

: 56713-62-3, 110282-51-4
C24H52N2(2+)*2Br(1-)

Conditions

Conditions	Yield
In acetonitrile for 0.5h; Heating;	95%

: 112-18-5
N,N-dimethylaminododecane

: 821-06-7
(E)-1,4-dibromobutene

: 100186-75-2, 108574-07-8
trans-1,4-bis(dodecyldimethylammonio)-2-butylene dibromide

Conditions

Conditions	Yield
In acetonitrile for 0.5h; Heating;	95%

: 821-06-7
(E)-1,4-dibromobutene

: 41145-51-1
octyldibutylamine

: 100186-84-3, 110282-53-6
C36H76N2(2+)*2Br(1-)

Conditions

Conditions	Yield
In acetonitrile for 0.5h; Heating;	95%

: 821-06-7
(E)-1,4-dibromobutene

: 14396-64-6, 50477-73-1
trans-2,3-di(bromomethyl)oxirane

Conditions

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In chloroform for 20h; Heating;	95%

(E)-1,4-Dibromobut-2-ene Consensus Reports

Reported in EPA TSCA Inventory.

(E)-1,4-Dibromobut-2-ene Specification

The trans-1,4-Dibromobut-2-ene, with the CAS registry number 821-06-7 and EINECS registry number 212-472-7, has the systematic name and IUPAC name of (2E)-1,4-dibromobut-2-ene. It is a kind of white to light yellow crystal powder, and belongs to the following product categories: Alkenyl; Halogenated Hydrocarbons; Organic Building Blocks. And the molecular formula of this chemical is C₄H₆Br₂. What's more, it should be stored in the refrigerator.

The physical properties of trans-1,4-Dibromobut-2-ene are as following: (1)ACD/LogP: 2.41; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.41; (4)ACD/LogD (pH 7.4): 2.41; (5)ACD/BCF (pH 5.5): 39.68; (6)ACD/BCF (pH 7.4): 39.68; (7)ACD/KOC (pH 5.5): 485.15; (8)ACD/KOC (pH 7.4): 485.15; (9)#H bond acceptors: 0; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 0 Å²; (13)Index of Refraction: 1.542; (14)Molar Refractivity: 36.1 cm³; (15)Molar Volume: 114.5 cm³; (16)Polarizability: 14.31×10^-24cm³; (17)Surface Tension: 37.1 dyne/cm; (18)Density: 1.867 g/cm³; (19)Flash Point: 71.9 °C; (20)Enthalpy of Vaporization: 42.13 kJ/mol; (21)Boiling Point: 203 °C at 760 mmHg; (22)Vapour Pressure: 0.405 mmHg at 25°C.

Preparation and uses of trans-1,4-Dibromobut-2-ene: It can be prepared by 1,3-butadiene and bromine. Dissolve 126g liquid 1,3-butadiene with the 20mL carbon tetrachloride at -5°C to 15°C. Drop 76mL bromine into the solution with stirring in the presence of solvent carbon tetrachloride. By reduced pressure distillation, the carbon tetrachloride is evaporated, and add isopyknic sherwood oil and keep the temperature 60-90 °C. After filter and cool, it will separate out trans-1,4-Dibromobut-2-ene. What's more, it is usually used as intermediate in the organic synthesis.

You should be cautious while dealing with this chemical. It is toxic by inhalation and if swallowed, and it may also cause burns. Therefore, you had better take the following instructions: Wear suitable protective clothing, gloves and eye/face protection, and in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice; In case of accident or if you feel unwell, seek medical advice immediately (show label where possible); After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer).

You can still convert the following datas into molecular structure:
(1)SMILES: BrC/C=C/CBr
(2)InChI: InChI=1/C4H6Br2/c5-3-1-2-4-6/h1-2H,3-4H2/b2-1+
(3)InChIKey: RMXLHIUHKIVPAB-OWOJBTEDBG

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	oral	29mg/kg (29mg/kg)		Shell Chemical Company. Unpublished Report. Vol. -, Pg. 9, 1961.
rat	LD50	oral	62mg/kg (62mg/kg)		Shell Chemical Company. Unpublished Report. Vol. -, Pg. 9, 1961.

Product Name

(E)-1,4-Dibromobut-2-ene

Synthetic route

(E)-1,4-Dibromobut-2-ene Consensus Reports

(E)-1,4-Dibromobut-2-ene Specification

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