557-91-5

Basic information

• Product Name: 1,1-Dibromoethane
• Synonyms: 1,1-Dibromoethane ,98.5% [stabilized];1,1-DibroMoethane, stabilized, 99% 100GR;1,1-DibroMoethane, 99%, stabilized, stabilized;1,1-Dibromethan;1,1-dibromo-ethan;CH3CHBr2;Ethane,1,1-dibromo-;Ethylidene dibromide
• CAS NO: 557-91-5
• Molecular Formula: C₂H₄Br₂
• Molecular Weight: 187.86
• EINECS: 209-184-9
• Mol File: 557-91-5.mol
• Article Data: 7

Chemical Properties

• Melting Point: -63°C
• Boiling Point: 107 °C
• Flash Point: °C
• Appearance: Clear colorless to brown/Liquid
• Density: 2.06
• Vapor Pressure: 35.4mmHg at 25°C
• Refractive Index: 1.509-1.512
• Water Solubility: Insoluble in water
• CAS DataBase Reference: 1,1-Dibromoethane(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1-Dibromoethane(557-91-5)
• EPA Substance Registry System: 1,1-Dibromoethane(557-91-5)

Safety Data

• Hazard Codes: Xn
• Statements: 40-20/21/22
• Safety Statements: 45-36/37
• RIDADR: 2810
• RTECS: KH9000000
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 557-91-5(Hazardous Substances Data)

Usage

Chemical Properties

clear colourless to brownish liquid

InChI:InChI=1/C2H4Br2/c1-2(3)4/h2H,1H3

Synthetic route

methyl iodide (74-88-4) + 1,2-dibromomethane (74-95-3) → 1,1-Dibromoethane (557-91-5) + H2

Conditions	Yield
With tetraethylammonium chloride In acetonitrile Ambient temperature; electrochemical conditions (Fe cathode);	A 55.9% B n/a

ethyl bromide (74-96-4) → 1,1-Dibromoethane (557-91-5)

Conditions	Yield
With chloroethane; bromine at 40 - 100℃; under 37 Torr; Irradiation; temperature dependence of the relative rate constants;
With bromine at 170℃;
With bromine at 198℃; unter Belichtung bei Abwesenheit von Eisen;

Vinyl bromide (593-60-2) → 1,1-Dibromoethane (557-91-5)

Conditions	Yield
With hydrogen bromide
With water; hydrogen bromide
With hydrogen bromide; acetic acid

Vinyl bromide (593-60-2) → 1,1-Dibromoethane (557-91-5) + ethylene dibromide (106-93-4)

Conditions	Yield
With magnesium hydrosilicate; hydrogen bromide

1,1-dichloroethane (75-34-3) → 1,1-Dibromoethane (557-91-5)

Conditions	Yield
With aluminum tri-bromide

2-bromo-propionic acid amide (5875-25-2) → 1,1-Dibromoethane (557-91-5)

Conditions	Yield
With sodium hypobromide

acetaldehyde (75-07-0) → 1,1-Dibromoethane (557-91-5)

Conditions	Yield
With phosphorus trichloride dibromide

ethylene dibromide (106-93-4) → 1,1-Dibromoethane (557-91-5)

Conditions	Yield
at 300 - 315℃;
at 300℃;

2-Bromopropionic acid (598-72-1) → 1,1-Dibromoethane (557-91-5)

Conditions	Yield
With potassium hydroxide; platinum Electrolysis;

paracetaldehyde (123-63-7) → 1,1-Dibromoethane (557-91-5)

Conditions	Yield
With phosphorus trichloride dibromide

acetylene (74-86-2) → Vinyl bromide (593-60-2) + 1,1-Dibromoethane (557-91-5)

Conditions	Yield
With mercury bromide; hydrogen bromide at 200℃;

acetylene (74-86-2) → 1,1-Dibromoethane (557-91-5)

Conditions	Yield
With hydrogen bromide

ethyl bromide (74-96-4) → Vinyl bromide (593-60-2) + 1,1-Dibromoethane (557-91-5) + ethane (74-84-0) + ethene (74-85-1) + n-butane (106-97-8)

Conditions	Yield
at 24.9℃; Quantum yield; Irradiation; dependence of the product quantum yields on ethyl bromide pressure, photolysios time and additives (as N2, CF4, NO).;

ethyl bromide (74-96-4) → 1,1-Dibromoethane (557-91-5) + 2,3-dibromobutane (5408-86-6) + ethane (74-84-0) + ethene (74-85-1) + n-butane (106-97-8)

Conditions	Yield
With nitrogen(II) oxide under 1.1 Torr; Quantum yield; Product distribution; Ambient temperature; Irradiation; var. pressure; effect of inert gas, radical scavenger;

1-bromo-1-chloroethane (593-96-4) → 1,1-dichloroethane (75-34-3) + 1,1-Dibromoethane (557-91-5)

Conditions	Yield
copper and nickel chlorides at 170℃; Equilibrium constant; Thermodynamic data; 200 - 250 deg C, ΔH(excit.), ΔS(excit).;

acetaldehyde (75-07-0) + PCl3Br2 → 1,1-Dibromoethane (557-91-5)

water (7732-18-5) + 2-Bromopropionic acid (598-72-1) + platinum electrodes → 1,1-Dibromoethane (557-91-5)

Conditions	Yield
des Kalium-Salzes.Electrolysis;

water (7732-18-5) + hydrogen bromide (10035-10-6, 12258-64-9) + acetylene (74-86-2) + mercury (II)-bromide → Vinyl bromide (593-60-2) + 1,1-Dibromoethane (557-91-5)

Conditions	Yield
at 100℃; under 80 - 240 Torr; Kinetics;

3-bromo-3-methyldiazirine (4222-23-5) → Vinyl bromide (593-60-2) + 1,1-Dibromoethane (557-91-5) + ethene (74-85-1) + ethylene dibromide (106-93-4) + acetylene (74-86-2) + 1,2-dibromomethane (74-95-3) + tribromoethane, N2

Conditions	Yield
With (Z)-2-Butene Product distribution; Mechanism; Ambient temperature; Irradiation; gas phase photolysis; further additives, different conditions;

Vinyl bromide (593-60-2) + water (7732-18-5) + hydrogen bromide (10035-10-6, 12258-64-9) → 1,1-Dibromoethane (557-91-5)

ethyl bromide (74-96-4) + bromine (7726-95-6) → 1,1-Dibromoethane (557-91-5)

Conditions	Yield
at 198℃; unter Belichtung;
at 230℃; unter Belichtung;

Vinyl bromide (593-60-2) + hydrogen bromide (10035-10-6, 12258-64-9) + acetic acid (64-19-7) → 1,1-Dibromoethane (557-91-5)

Conditions	Yield
at 100℃;
at 50℃;

Vinyl bromide (593-60-2) + hydrogen bromide (10035-10-6, 12258-64-9) + aluminium bromide (7727-15-3) + acetic acid (64-19-7) → 1,1-Dibromoethane (557-91-5)

Conditions	Yield
at 50℃;
at 100℃;

Vinyl bromide (593-60-2) + hydrogen bromide (10035-10-6, 12258-64-9) + acetic acid (64-19-7) + BiBr3 → 1,1-Dibromoethane (557-91-5)

Conditions	Yield
at 50℃;
at 100℃;

Vinyl bromide (593-60-2) + hydrogen bromide (10035-10-6, 12258-64-9) + bismuth bromide → 1,1-Dibromoethane (557-91-5)

Conditions	Yield
at 100 - 200℃;

Vinyl bromide (593-60-2) + hydrogen bromide (10035-10-6, 12258-64-9) + acetic acid (64-19-7) + FeBr3 → 1,1-Dibromoethane (557-91-5)

Conditions	Yield
at 50℃;
at 100℃;

Vinyl bromide (593-60-2) + hydrogen bromide (10035-10-6, 12258-64-9) + acetic acid (64-19-7) + HgBr2 → 1,1-Dibromoethane (557-91-5)

Conditions	Yield
at 50℃;
at 100℃;

Vinyl bromide (593-60-2) + hydrogen bromide (10035-10-6, 12258-64-9) + iron (III)-bromide → 1,1-Dibromoethane (557-91-5)

Conditions	Yield
at 100 - 200℃;

Vinyl bromide (593-60-2) + hydrogen bromide (10035-10-6, 12258-64-9) + silicic acid-gel → 1,1-Dibromoethane (557-91-5)

Conditions	Yield
at 100 - 200℃;

Vinyl bromide (593-60-2) + hydrogen bromide (10035-10-6, 12258-64-9) → 1,1-Dibromoethane (557-91-5) + ethylene dibromide (106-93-4)

Conditions	Yield
Produkt 2. entsteht nur bei Gegenwart von Diphenylamin;
Produkt 2. entsteht nur bei Gegenwart von Dimethylanilin;
Produkt 2. entsteht nur bei Gegenwart von Thiophenol+MgCl2;

1,1-Dibromoethane (557-91-5) + phenylacetonitrile (140-29-4) → 1-cyano-1-phenylcyclopropane (935-44-4)

Conditions	Yield
With nitrogen In N-methyl-acetamide; water; mineral oil	100%

styrene (292638-84-7) + 1,1-Dibromoethane (557-91-5) → (2-methylcyclopropyl)benzene (3145-76-4)

Conditions	Yield
With lanthanum; iodine In tetrahydrofuran at 67℃; for 5h;	98%

magnesium dihydride (7439-95-4) + 7-Bromo-1-[(S)-2-(tert-butyldimethyl-silanyloxy)-propyl]-6-oxiranylmethoxy-1H-indazole (478132-37-5) + 1,1-Dibromoethane (557-91-5) → 1-Bromo-3-[7-bromo-1-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-propyl]-1H-indazol-6-yloxy]-propan-2-ol (478132-38-6)

Conditions	Yield
With ammonium chloride In tetrahydrofuran	95%

1,1-Dibromoethane (557-91-5) + C64H88O12Si (1236055-59-6) → C62H84O11Si (1236055-60-9)

Conditions	Yield
Stage #1: With N,N,N,N,-tetramethylethylenediamine; titanium tetrachloride In tetrahydrofuran; dichloromethane at 0 - 25℃; for 0.666667h; Inert atmosphere; Stage #2: With lead(II) chloride; zinc In tetrahydrofuran; dichloromethane at 25℃; for 0.333333h; Inert atmosphere; Stage #3: 1,1-Dibromoethane; C64H88O12Si In tetrahydrofuran; dichloromethane for 1h; Inert atmosphere; Reflux;	93%

1,1-Dibromoethane (557-91-5) + 2,2-dimethylpropionic acid 3,5,5-trimethylcyclohex-2-enyl ester → 3-((Z)-1-tert-butylpropenyloxy)-1,5,5-trimethylcyclohexene

Conditions	Yield
With N,N,N,N,-tetramethylethylenediamine; zinc; titanium tetrachloride In tetrahydrofuran; dichloromethane	91%

1,1-Dibromoethane (557-91-5) + 2a; R1=R2=C6H5 → 2-Methyl-4,5-diphenyl-cyclopent-4-ene-1,3-dione (59345-70-9)

Conditions	Yield
In toluene at 50℃; for 5h;	90%

1,1-Dibromoethane (557-91-5) + isopropyl benzoate (939-48-0) → ((Z)-1-Isopropoxy-propenyl)-benzene (14093-66-4)

Conditions	Yield
With N,N,N,N,-tetramethylethylenediamine; titanium tetrachloride; zinc In tetrahydrofuran at 25℃; for 2h;	88%

1,1-Dibromoethane (557-91-5) + Butyric acid ((E)-2-propenyl)-phenyl ester → 1-[1-Eth-(E)-ylidene-butoxy]-2-((E)-propenyl)-benzene

Conditions	Yield
With N,N,N,N,-tetramethylethylenediamine; titanium tetrachloride; zinc; lead(II) chloride In tetrahydrofuran at 20℃; for 5h;	88%

3-thiophene carboxaldehyde (498-62-4) + 1,1-Dibromoethane (557-91-5) + ammonium chloride + isopropylmagnesium chloride (1068-55-9) + 1-chloro-3-hydroxypropane (627-30-5) → 1-(3-Thienyl)-1,4-butanediol (357444-08-7)

Conditions	Yield
With magnesium In tetrahydrofuran	88%

allyl 6β-[(methoxycarbonyl)acetamido]-2,2-dimethylpenam-3-carboxylate + 1,1-Dibromoethane (557-91-5) → allyl 6β-[(1,3-dithiolan-2-ylidene)(methoxycarbonyl)acetamido]-2,2-dimethylpenam-3-carboxylate

Conditions	Yield
With carbon disulfide In N-methyl-acetamide	88%

1,1-Dibromoethane (557-91-5) + ethyl cysteinate hydrochloride (868-59-7, 7319-36-0, 75521-14-1, 93964-73-9) → thiomorpholinecarboxylic acid ethyl ester (152009-44-4)

Conditions	Yield
With triethylamine In tetrahydrofuran	87%

benzoic acid methyl ester (93-58-3) + 1,1-Dibromoethane (557-91-5) → (1-methoxyprop-1-en-1-yl)benzene (4518-65-4, 4541-69-9, 79342-00-0)

Conditions	Yield
With N,N,N,N,-tetramethylethylenediamine; titanium tetrachloride; zinc In tetrahydrofuran at 25℃; for 2h;	86%

magnesium dihydride (7439-95-4) + 7-Bromo-1-[2-(tert-butyldimethyl-silanyloxy)-propyl]-6-oxiranylmethoxy-1H-indazole (478132-27-3) + 1,1-Dibromoethane (557-91-5) → 1-Bromo-3-[7-bromo-1-[2-(tert-butyl-dimethyl-silanyloxy)-propyl]-1H-indazol-6-yloxy]-propan-2-ol (478132-28-4)

Conditions	Yield
With ammonium chloride In tetrahydrofuran	86%

1,1-Dibromoethane (557-91-5) + cyclopent-3-enol (14320-38-8) → exo-6-Methyl-cis-bicyclo<3.1.0>hexan-3-ol (23038-07-5)

Conditions	Yield
With diethylzinc; copper; zinc In diethyl ether for 12h; Ambient temperature;	85%

3-(4-chlorophenyl)-4-(4-hydroxybenzyl)-7-methoxychromen-2-one (601513-40-0) + 1,1-Dibromoethane (557-91-5) → 3-(4-chlorophenyl)-4-(4-(2-bromoethoxy)benzyl)-7-methoxychromen-2-one (601513-41-1)

Conditions	Yield
With potassium carbonate In acetone	83%
With potassium carbonate In acetone	83%

N-(cyclohexanecarbonyl)piperidine (7103-46-0) + 1,1-Dibromoethane (557-91-5) → 1-((E)-1-Cyclohexyl-propenyl)-piperidine (121782-18-1, 121782-22-7)

Conditions	Yield
With N,N,N,N,-tetramethylethylenediamine; titanium tetrachloride; zinc In tetrahydrofuran at 25℃; for 18h;	82%

1,1-Dibromoethane (557-91-5) + bis(pinacol)diborane (73183-34-3) → 2,2'-(ethane-1,1-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

Conditions	Yield
With copper(l) iodide; lithium methanolate In N,N-dimethyl-formamide at 40℃; for 24h; Schlenk technique; Inert atmosphere;	82%
With lithium tert-butoxide In N,N-dimethyl-formamide at 30℃; under 760.051 Torr; for 6h; Irradiation;	74%
With copper(l) iodide; lithium tert-butoxide In N,N-dimethyl-formamide at 40℃; for 24h; Inert atmosphere;	71%

1,1-Dibromoethane (557-91-5) + (E)-(5R,7R,8R)-8-((benzyloxy)methoxy)-7-((4-methoxybenzyl)oxy)non-1-en-5-yl 5-((tert-butyldimethylsilyl)oxy)-2,2-dimethylpent-3-enoate (1261422-99-4) → (((E)-4-((S)-2-((2R,3R)-3-((benzyloxy)methoxy)-2-((4-methoxybenzyl)oxy)butyl)-3,4-dihydro-2H-pyran-6-yl)-4-methylpent-2-en-1-yl)oxy)(tert-butyl)dimethylsilane (1261423-01-1)

Conditions	Yield
With N,N,N,N,-tetramethylethylenediamine; titanium tetrachloride; lead(II) chloride; zinc In dichloromethane for 2h; Reflux;	82%

styrene (292638-84-7) + 1,1-Dibromoethane (557-91-5) → 1-bromo-1-methyl-2-phenylcyclopropane (81651-71-0)

Conditions	Yield
With sodium hexamethyldisilazane In toluene at 25℃; for 24h;	81.7%
With sodium hexamethyldisilazane In toluene at 0 - 25℃; for 24h; Inert atmosphere;	37%

1,1-Dibromoethane (557-91-5) + benzoic acid tert-butyl ester (774-65-2) → (1-tert-butoxypropenyl)-benzene (109585-91-3, 109585-92-4)

Conditions	Yield
With N,N,N,N,-tetramethylethylenediamine; titanium tetrachloride; zinc In tetrahydrofuran at 25℃; for 2h;	81%

1,1-Dibromoethane (557-91-5) + (E)-(2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-5-phenyl-pent-4-enoic acid ethyl ester → tert-Butyl-[(Z)-(1R,2S)-3-ethoxy-2-methyl-1-((E)-styryl)-pent-3-enyloxy]-dimethyl-silane

Conditions	Yield
With N,N,N,N,-tetramethylethylenediamine; titanium tetrachloride; zinc; lead(II) chloride In tetrahydrofuran at 20℃; for 14h; alkylidenation;	81%

1,1-Dibromoethane (557-91-5) + trimethylsilyl cyclohexanecarboxylate (69435-89-8) → (Z)-1-cyclohexyl-1-(trimethylsilyloxy)-1-propene (76436-98-1)

Conditions	Yield
With N,N,N,N,-tetramethylethylenediamine; titanium tetrachloride; zinc In tetrahydrofuran at 25℃; for 2h;	80%

1,1-Dibromoethane (557-91-5) + Phenyl-acetic acid ((E)-2-propenyl)-phenyl ester → 1-((E)-1-Benzyl-propenyloxy)-2-((E)-propenyl)-benzene

Conditions	Yield
With N,N,N,N,-tetramethylethylenediamine; titanium tetrachloride; zinc; lead(II) chloride In tetrahydrofuran at 20℃; for 5h;	79%

1,1-Dibromoethane (557-91-5) + cyclohexanecarboxylic acid 4-methoxybenzylic ester → 1-(1-cyclohexyl-propenyloxymethyl)-4-methoxybenzene

Conditions	Yield
With N,N,N,N,-tetramethylethylenediamine; zinc; titanium tetrachloride In tetrahydrofuran; dichloromethane	78%

benzoic acid phenyl ester (93-99-2) + 1,1-Dibromoethane (557-91-5) → C15H14O (76967-60-7)

Conditions	Yield
With N,N,N,N,-tetramethylethylenediamine; titanium tetrachloride; zinc In tetrahydrofuran at 25℃; for 3h;	76%

1,1-Dibromoethane (557-91-5) + methyl n-dodecanoate (111-82-0) → 3-methoxy-2-tetradecene (120387-78-2)

Conditions	Yield
With N,N,N,N,-tetramethylethylenediamine; titanium tetrachloride; zinc In tetrahydrofuran at 25℃; for 2h;	75%

1,1-Dibromoethane (557-91-5) + 2b; R1=C6H5, R2=H → Methyl-2 phenyl-4 cyclopenten-4 dion-1.3 (56542-38-2)

Conditions	Yield
In toluene at 70℃; for 8h;	75%

1,1-Dibromoethane (557-91-5) + 2-fluoro-4-nitrophenol (403-19-0) → 1-Bromo-2-(2-fluoro-5-nitrophenoxy)-ethane

Conditions	Yield
With potassium carbonate In hexane; ethyl acetate; N,N-dimethyl-formamide	75%

1,1-Dibromoethane (557-91-5) + cyclohexanecarboxylic acid 3,5,5-trimethylcyclohex-2-enyl ester → 3-((Z)-1-cyclohexylpropenyloxy)-1,5,5-trimethylcyclohexene

Conditions	Yield
With N,N,N,N,-tetramethylethylenediamine; zinc; titanium tetrachloride In tetrahydrofuran; dichloromethane	74%

1-(p-chlorophenyl)-2-cyclopropyl-2-methylethan-1-one (123989-29-7) + 1,1-Dibromoethane (557-91-5) → 2-(4-chlorophenyl)-2-(1-cyclopropylethyl)-3-methyloxirane (1615196-91-2)

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃;	73%

Upstream product

• 593-60-2 Vinyl bromide 
• 75-34-3 1,1-dichloroethane 
• 5875-25-2 2-bromo-propionic acid amide 
• 75-07-0 acetaldehyde 
• 106-93-4 ethylene dibromide 
• 598-72-1 2-Bromopropionic acid 
• 74-86-2 acetylene 
• 593-96-4 1-bromo-1-chloroethane 
• 7732-18-5 water 
• 10035-10-6 hydrogen bromide 
• 4222-23-5 3-bromo-3-methyldiazirine 
• 74-96-4 ethyl bromide 
• 7726-95-6 bromine 
• 64-19-7 acetic acid 

Downstream Products

• 593-60-2 Vinyl bromide 
• 74-86-2 acetylene 
• 4991-30-4 1,1-dibenzoylethane 
• 104-90-5 5-ethyl-2-methyl-pyridine 
• 75-37-6 1,1-difluoroethane 
• 78-74-0 1,1,2-tribromoethane 
• 106-93-4 ethylene dibromide 
• 75-07-0 acetaldehyde 
• 554-12-1 propanoic acid methyl ester 
• 4436-22-0 1-phenylpropylene oxide 
• 14661-79-1 dimethyl 3β-methylcyclopropane-1α,2α-dicarboxylate 
• 28363-79-3 methyl 3-methylcyclopropane-1α,2β-dicarboxylate 
• 87421-39-4 dimethyl 3α-methylcyclopropane-1α,2α-dicarboxylate 
• 106-65-0 Dimethyl succinate 

Relevant articles and documents

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CATHODIC CLEAVAGE OF THE C-H BOND. ELECTROCHEMICAL REDUCTION OF HALOGEN-CONTAINING ORGANIC COMPOUNDS ON TRANSITION METALS

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Photodecomposition of Gaseous Bromoethane at 163.4 nm

The 163.4-nm photolysis of gaseous C2H5Br has been investigated at 298 K over the pressure range 2-100 torr, using a bromine lamp.The effects of additives, N2,CF4, and NO, were also studied.In the pure system the observed reaction products and their respective quantum yields are C2H4 (ca.0.36), C2H6 (0.42-0.79), C2H3Br(0.1-0.24), CH3CHBr2 (0.24-0.32) and n-C4H10 (0.01), most yields increasing with substrate pressure.An opposite trend is observed with increasing pressure of inert gases.The addition of NO as a radical scavenger completely supresses the formation of C2H6, C2H3Br, CH3CHBr2, and n-C4H10, and partially reduces the yield of C2H4.The results are interpreted in terms of the initial formation of two electronically excited states which are linked by way of a pressure dependence, one of which yields C2H4 by molecular elimination of HBr, while the second decomposes by carbon-halogen bond fission.The kinetics of the secondary process are discussed in some detail.