79-27-6

Basic information

• Product Name: 1,1,2,2-Tetrabromoethane
• Synonyms: 1,1,2,2-Tetrabromoethylene;Acetylene tetrabromide;Muthmann's liquid;NSC406889;TBE
• CAS NO: 79-27-6
• Molecular Formula: C₂H₂Br₄
• Molecular Weight: 345.65328
• EINECS: 201-191-5
• Mol File: 79-27-6.mol
• Article Data: 5

Chemical Properties

• Melting Point: -2℃
• Boiling Point: 243.5 °C at 760 mmHg
• Flash Point: 97 °C
• Appearance: yellowish heavy liquid
• Density: 3.004 g/cm³
• Vapor Density: 11.9 (vs air)
• Vapor Pressure: 0.0499mmHg at 25°C
• Refractive Index: 1.653
• Water Solubility: 0.63 g/L (20℃)
• CAS DataBase Reference: 1,1,2,2-Tetrabromoethane(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1,2,2-Tetrabromoethane(79-27-6)
• EPA Substance Registry System: 1,1,2,2-Tetrabromoethane(79-27-6)

Safety Data

• Hazard Codes: T+:Very toxic
• Statements: R26:; R36:; R52/53:
• Safety Statements: S1/2:; S24:; S27:; S45:; S61:
• RIDADR: 2504
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 79-27-6(Hazardous Substances Data)

Usage

General Description

1,1,2,2-Tetrabromoethane, also known as acetylene tetrabromide, is a chemical compound that consists of four bromine atoms attached to a central ethane molecule. It is a colorless liquid with a sweet, chloroform-like odor, and is insoluble in water. 1,1,2,2-Tetrabromoethane was commonly used as a solvent, flame retardant, and in the production of gasoline additives. However, it has since been phased out of many uses due to its environmental and health risks, including its classification as a potential human carcinogen. Exposure to 1,1,2,2-Tetrabromoethane can cause irritation of the skin, eyes, and respiratory system, as well as central nervous system depression. It is important to handle and dispose of this chemical with caution in order to minimize its potential harm to human health and the environment.

InChI:InChI=1/C2H2Br4/c3-1(4)2(5)6/h1-2H

Synthetic route

cis+trans-dibromoethylene (540-49-8) → 1,1,2,2-tetrabromoethane (79-27-6) + C2H2BrF5S + C2H2BrF5S

Conditions	Yield
With pentafluorosulfanyl bromide at 20℃; for 24h; Irradiation;	A n/a B n/a C 97.1%

cis+trans-dibromoethylene (540-49-8) → 1,1,2,2-tetrabromoethane (79-27-6)

Conditions	Yield
With bromine

ethylene dibromide (106-93-4) → 1,1,2,2-tetrabromoethane (79-27-6)

Conditions	Yield
With aluminum tri-bromide; bromine at 105 - 110℃;

acetylene (74-86-2) → 1,1,2,2-tetrabromoethane (79-27-6)

Conditions	Yield
With water; bromine
With water; bromine; potassium bromide at 22℃; Electrolysis.unter langsamem Hindurchleiten von Acetylen;

1,1,2,2-tetrachloroethane (79-34-5) → 1,1,2,2-tetrabromoethane (79-27-6)

Conditions	Yield
With aluminum tri-bromide

Trichloroethylene (79-01-6) → 1,1,2,2-tetrabromoethane (79-27-6) + 1,1,2-tribromo-1,2,2-trichloro-ethane (594-78-5)

Conditions	Yield
With bromine Irradiation;

2-ethoxy-1,3-dioxolane (4544-20-1) + Bromoform (75-25-2) → 1,1,2,2-tetrabromoethane (79-27-6)

Conditions	Yield
dibenzoyl peroxide at 100℃; for 2h; Rate constant; Product distribution; other temperature, other time;

2-ethoxy-1,3-dioxane (76508-46-8) + Bromoform (75-25-2) → 1,1,2,2-tetrabromoethane (79-27-6)

Conditions	Yield
dibenzoyl peroxide at 100℃; for 2h; Rate constant; Product distribution; other temperature;

2-phenyl-1,3-oxathiolane (5721-88-0) → 1,1,2,2-tetrabromoethane (79-27-6) + S-(2-bromoethyl) benzothioate (81110-22-7) + 1,2-dibromomethane (74-95-3)

Conditions	Yield
With Bromoform; di-tert-butyl peroxide at 130℃; for 4.5h; Yields of byproduct given;	A n/a B 16 % Turnov. C n/a

2-propyl-1,3-oxathiolan (27001-65-6) → 1,1,2,2-tetrabromoethane (79-27-6) + 2-bromoethyl thiobutyrate (83124-63-4) + 1,2-dibromomethane (74-95-3)

Conditions	Yield
With Bromoform; di-tert-butyl peroxide at 130℃; for 4.5h; Yields of byproduct given;	A n/a B 14 % Turnov. C n/a

2-ethyl-[1,3]oxathiolane (16048-04-7) → 1,1,2,2-tetrabromoethane (79-27-6) + 2-bromoethyl thiopropionate (83124-62-3) + 1,2-dibromomethane (74-95-3)

Conditions	Yield
With Bromoform; di-tert-butyl peroxide at 130℃; for 4.5h; Yields of byproduct given;	A n/a B 18 % Turnov. C n/a

Bromoform (75-25-2) + 2-(hexyloxy)-1,3-dioxolane (83498-70-8) → 1,1,2,2-tetrabromoethane (79-27-6)

Conditions	Yield
dibenzoyl peroxide at 100℃; for 2h; Rate constant; Product distribution; other temperature;

Bromoform (75-25-2) + 2-(hexyloxy)-m-dioxane → 1,1,2,2-tetrabromoethane (79-27-6)

Conditions	Yield
dibenzoyl peroxide at 100℃; for 2h; Rate constant; Product distribution; other temperature;

Bromoform (75-25-2) → 1,1,2,2-tetrabromoethane (79-27-6) + 2-bromoethyl thiopropionate (83124-62-3) + 1,2-dibromomethane (74-95-3)

Conditions	Yield
With 2-ethyl-[1,3]oxathiolane; di-tert-butyl peroxide at 130℃; for 4.5h;	A n/a B 18 % Turnov. C n/a

Bromoform (75-25-2) → 1,1,2,2-tetrabromoethane (79-27-6) + 2-bromoethyl thiobutyrate (83124-63-4) + 1,2-dibromomethane (74-95-3)

Conditions	Yield
With 2-propyl-1,3-oxathiolan; di-tert-butyl peroxide at 130℃; for 4.5h;	A n/a B 14 % Turnov. C n/a

Bromoform (75-25-2) → 1,1,2,2-tetrabromoethane (79-27-6) + S-(2-bromoethyl) benzothioate (81110-22-7) + 1,2-dibromomethane (74-95-3)

Conditions	Yield
With 2-phenyl-1,3-oxathiolane; di-tert-butyl peroxide at 130℃; for 4.5h;	A n/a B 16 % Turnov. C n/a

Bromotrichloromethane (75-62-7) + 2-(hexyloxy)-1,3-dioxolane (83498-70-8) → 1,1,2,2-tetrabromoethane (79-27-6)

Conditions	Yield
dibenzoyl peroxide at 90℃; for 2h; Rate constant; Product distribution; other temperature;

Bromoform (75-25-2) + 7,7-dimethyl-1,4,5,6-tetraphenyl-2,3-benzo-7-silanorbornadiene (18816-24-5) → 1,1,2,2-tetrabromoethane (79-27-6) + dimethyldibromosilane (4095-10-7) + 1,2,3,4-tetraphenylnaphthalene (751-38-2) + 1,2-dibromomethane (74-95-3)

Conditions	Yield
In hexane at 22.9℃; Rate constant; Product distribution; Mechanism; Irradiation; laser pulse photolysis technique; investigated by UV and 1H NMR measurements;

ethane (74-84-0) → 1,1,2,2-tetrabromoethane (79-27-6) + ethyl bromide (74-96-4) + ethylene dibromide (106-93-4)

Conditions	Yield
With 2AlBr3*CBr4; bromine at 55 - 65℃; under 760 Torr; for 3h; Title compound not separated from byproducts;	A 53 % Turnov. B 3 % Turnov. C 17 % Turnov.

aluminium bromide (7727-15-3) + ethylene dibromide (106-93-4) → 1,1,2,2-tetrabromoethane (79-27-6)

aluminium bromide (7727-15-3) + 1,1,2,2-tetrachloroethane (79-34-5) → 1,1,2,2-tetrabromoethane (79-27-6)

Conditions	Yield
unterhalb des Siedepunktes;

cis+trans-dibromoethylene (540-49-8) + benzene (71-43-2) + thiocyanato → 1,1,2,2-tetrabromoethane (79-27-6) + 1,2,2-tribromo-ethyl thiocyanate + <β-bromo-ethyl>-thiocyanate + α.β-dirhodan-ethylene

Conditions	Yield
im Sonnenlicht; bei manchen Versuchen auch Prod.5: 1.2-Dibrom-1.2-dirhodan-aethan; cis-trans-mixture;

1,1,2,2-tetrabromoethane (79-27-6) → cis+trans-dibromoethylene (540-49-8)

Conditions	Yield
With iron In N,N-dimethyl-formamide	93%
With ethanol; zinc
With aluminium amalgam

1,1,2,2-tetrabromoethane (79-27-6) → 1,1,2-tribromoethylene (598-16-3)

Conditions	Yield
With sodium hydroxide; Katamin AB In water at 25 - 30℃; for 2h;	90%
With diethyl ether; sodium ethanolate
With diethyl ether; sodium

4-iodopyrazole (3469-69-0) + 1,1,2,2-tetrabromoethane (79-27-6) → 1,1,2,2-tetrakis(4-iodo-1H-pyrazol-1-yl)ethane (1073267-96-5)

Conditions	Yield
Stage #1: 4-iodopyrazole With potassium hydroxide In dimethyl sulfoxide at 80℃; for 0.5h; Stage #2: 1,1,2,2-tetrabromoethane In dimethyl sulfoxide for 2h;	86.7%

1,1,2,2-tetrabromoethane (79-27-6) + Diethyl methylphosphonate (683-08-9) → ethyl bromide (74-96-4) + 1,1,2-tribromoethylene (598-16-3) + ethyl methylphosphonic acid (1832-53-7)

Conditions	Yield
at 180℃; for 10h;	A 15% B 79% C 37%

1,1,2,2-tetrabromoethane (79-27-6) + t-butyldimethylsiloxy-3,5-dimethoxybenzene-4-lithio (96700-97-9) → t-butyldimethylsiloxy-4-bromo-3,5-dimethoxybenzene (96701-00-7)

Conditions	Yield
In toluene Ambient temperature;	77%

1,1,2,2-tetrabromoethane (79-27-6) + (R)-N-ferrocenylmethyl-2-methoxymethylpyrrolidine → (R,R(p))-1-bromo-2-[(2-methoxymethylpyrrolidin-1-yl)methyl]ferrocene

Conditions

Yield

With s-C4H9Li In diethyl ether; cyclohexane (Ar); using Schlenk techniques; addn. dropwise s-BuLi/C6H12 to CpFeC5H4CH2C4H7NCH2OMe/Et2O at -78°C; stirring for 1.5 h at -78°C and 1.5 h at -30°C; addn. of C2H2Br4/Et2O at -78°C for 0.5 h; stirring for 0.5 h and 16h at r.t.; quenching(H2O); sepn.; extn. aq. phase with CH2Cl2; washing of aq. phases with aq. Na2S2O5 and brine; extn. of org. phase with aq. citric acid; extn. of cobined aq. phase with Et2O; addn. NaOH to pH=9 at 0°C; extn. with Et2O; drying; chromy.Al2O3;

74%

1,1,2,2-tetrabromoethane (79-27-6) → 1,1-dibromo-2,2-difluoroethane (359-19-3)

Conditions	Yield
With chlorine monofluoride	72%
With mercury(II) fluoride at 150 - 160℃;
With hydrogen fluoride; mercury(II) oxide at 40 - 50℃;
With silver(II) fluoride at 80℃; Substitution;

NH-pyrazole (288-13-1) + 1,1,2,2-tetrabromoethane (79-27-6) → 1,1,2,2-tetrakis(1H-pyrazol-1-yl)ethane

Conditions	Yield
Stage #1: NH-pyrazole With potassium hydroxide In dimethyl sulfoxide at 80℃; for 1h; Stage #2: 1,1,2,2-tetrabromoethane In dimethyl sulfoxide for 5h;	71.4%
Stage #1: NH-pyrazole With potassium hydroxide In dimethyl sulfoxide at 80℃; for 0.5h; Stage #2: 1,1,2,2-tetrabromoethane In dimethyl sulfoxide at 80℃; for 5h; Further stages.;	57%

1,1,2,2-tetrabromoethane (79-27-6) + 1,1'-dilithioferrocene N,N,N'N'-tetramethylethylenediamine → 1,1'-dibromoferrocene (1293-65-8)

Conditions	Yield
With H2O In diethyl ether 1,1,2,2-tetrabromoethane in Et2O was added slowly to suspn. FcLi2(TMEDA) in Et2O at -60°C, soln. was allowed to warm to room temp., stired for 10 h and hydrolyzed with H2O and stired for 10 min; organic layer was separated and evapd., residue was extd. with Et2O andfiltered, solvent was removed and residue was crystd. from MeOH;	71%

1,1,2,2-tetrabromoethane (79-27-6) → 1,1-dibromo-2,2-difluoroethane (359-19-3) + 1,1,2-tribromo-2-fluoroethane (598-67-4)

Conditions	Yield
With chlorine monofluoride	A 12% B 70%
With bromine; antimony(III) fluoride at 120 - 125℃; for 23h;	A 19% B 11%
With bromine; antimony(III) fluoride at 120 - 125℃; for 23h;

1,1,2,2-tetrabromoethane (79-27-6) + 1,2-dibromoferrocene (238413-86-0) → 1,2,3-tribromoferrocene (1145715-22-5)

Conditions

Yield

With lithium tetramethylpiperidinide In tetrahydrofuran; hexane Schlenk techniques used under N2 or Ar, THF soln. of 2 (8.99 mmol) addedto freshly prepd. (from hexane soln. of nBuLi (8.96 mmol) and TMP (8.96 mmol) in THF) soln. of LiTMP and stirred for 3 h at -30°C, C2H2B r4 (8.96 mmol) added at -70°C; allowed to warm to room temp. for 18 h, H2O added, extracted with Et2O, dried over MgSO4, filtered, solvent removed under vac., petroleum ether added, filtered through alumina plug, partial evaporated, cooled to 4°C; XRD;

69%

1,1,2,2-tetrabromoethane (79-27-6) + ferrocene (102-54-5) → 1,1'-dibromoferrocene (1293-65-8)

Conditions	Yield
Stage #1: ferrocene With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In hexane Inert atmosphere; Stage #2: 1,1,2,2-tetrabromoethane In diethyl ether; hexane at -78℃; for 4h;	67%
Stage #1: ferrocene With n-butyllithium; N,N,N,N,-tetramethylethylenediamine Stage #2: 1,1,2,2-tetrabromoethane at -78℃;

1,1,2,2-tetrabromoethane (79-27-6) + C136H152O24 → C136H152O24*C2H2Br4

Conditions	Yield
at 105℃; for 36h; complexation;	65%

1,1,2,2-tetrabromoethane (79-27-6) + N,N-dimethylaminomethylferrocene (1271-86-9) → rac-2-(N,N-dimethylaminomethyl)bromoferrocene (245740-46-9, 12110-60-0, 245740-45-8)

Conditions

Yield

With n-butyllithium In tetrahydrofuran; diethyl ether all manipulations under inert atm. (Ar or N2); soln. of Fe compd. in Et2O cooled to 0°C, Li compd. added slowly, stirred at ambient temp.for 24 h, THF added, cooled to -78°C, Br compd. added, allowed t o warm to room temp., stirred at; ambient temp. overnight, water added, aq. phase extd. with ether, combined org. phase dried with anhydr. MgSO4, filtered, concd., chromy. (alumina, Et2O/Et2NH 95:5); elem. anal.;

62%

1,1,2,2-tetrabromoethane (79-27-6) + bromoferrocene (1273-73-0) + 1,2-dibromoferrocene (238413-86-0) + 1,2,3-tribromoferrocene (1145715-22-5) + 1,2,3,4-tetrabromoferrocene → 1,2,3,4,5-pentabromoferrocene (1145715-26-9)

Conditions

Yield

With lithium tetramethylpiperidinide In tetrahydrofuran Schlenk techniques used under N2 or Ar, mixt.(10.8 mmol) of 1 (51%), 2 (24%), 4 (18%) and 5 (7%) in THF added to LiTMP (100 mmol) in THF and stirred for 5 h at -30°C, C2H2Br4 (100 mmol) added at -78°C, warmed to room temp. for >16 h; quenched with H2O, extracted with CH2Cl2, organic layer washed with aq. 1M HCl and H2O, dried over MgSO4, solvent removed under vac., chromd. (neutral alumina, hexane), concentrated, allowed to stand at 5°C for 16 h; elem.anal., XRD;

57%

1,1,2,2-tetrabromoethane (79-27-6) + chlorogermane (13637-65-5) + methyllithium (917-54-4) → digermylacetylene (68196-77-0)

Conditions	Yield
In diethyl ether byproducts: LiBr, CH4, MeBr; absence of air and moisture; treatment of C2H2Br4 with 4 equiv. of MeLi (room temp., 1 h), evapn. (vac., 1 h), condensation of 2 equiv. of ClGeH3, warming to room temp. (5 min); fractional low-temp. distn. (condensing at 206 K);	50%

NH-pyrazole (288-13-1) + 1,1,2,2-tetrabromoethane (79-27-6) → 1,1,2,2-tetrakis(1H-pyrazol-1-yl)ethane + 1,1,2-tris(pyrazol-1-yl)ethene + (Z)-1,2-bis(1H-pyrazol-1-yl)ethylene (1313194-68-1)

Conditions	Yield
Stage #1: NH-pyrazole With potassium hydroxide In dimethyl sulfoxide at 80℃; for 0.5h; Stage #2: 1,1,2,2-tetrabromoethane In dimethyl sulfoxide at 80℃; for 24h;	A 47% B n/a C n/a

trimethyl phosphite (512-56-1) + 1,1,2,2-tetrabromoethane (79-27-6) → dimethylphosphoric acid (813-78-5) + 1,1,2-tribromoethylene (598-16-3)

Conditions	Yield
at 180℃; for 20h;	A 31% B 45%

1,1,2,2-tetrabromoethane (79-27-6) + 1,2,3-tribromoferrocene (1145715-22-5) → 1,2,3,4-tetrabromoferrocene + 1,2,3,4,5-pentabromoferrocene (1145715-26-9)

Conditions

Yield

With lithium tetramethylpiperidinide In tetrahydrofuran; hexane Schlenk techniques used under N2 or Ar, THF soln. of 4 (6.34 mmol) addedto freshly prepd. (from hexane soln. of nBuLi (15.8 mmol) and TMP (15.8 mmol) in THF) soln. of LiTMP and stirred for 3 h at -30°C, C2H2B r4 (15.8 mmol) added at -70°C; alloed to warm to room temp. for 18 h, H2O added, extracted with Et2O, dried over MgSO4, filtered, solvent removed under vac., recrystd. from petroleum ether/Et2O at 4°C; elem. anal.;

A 44% B 18%

1,1,2,2-tetrabromoethane (79-27-6) + 2,3,4-triferrocenylthiophene → 2-bromo-3,4,5-triferrocenylthiophene (1362991-84-1)

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane (under Ar, Schlenk); Fe-complex dissolved in THF, cooled to -40°C, Li-salt in hexane added dropwise, warmed to -25°C for 35 min, cooled to -40°C, ligand added, warmed to ambient temp., stirred for 3 h; volatiles removed, alumina column chromy. with hexane:toluene 3:1, collected, solvent evapd., crystd. from n-hexane/toluene 5:1; elem. anal.;	40%

1,1,2,2-tetrabromoethane (79-27-6) + 1,1'-dibromoferrocene (1293-65-8) → ferrocene (102-54-5) + 1,2-dibromoferrocene (238413-86-0)

Conditions

Yield

With tetramethylpiperidine; n-butyl lithium In tetrahydrofuran; hexane Schlenk techniques used under N2 or Ar, THF soln. of (BrC5H4)2Fe (25.0 mmol) treated at -70°C with soln. of nBuLi (25.0 mmol), after 30 min TMP (25.0 mmol) added, stirred for 3 h at -30--40°C, C2H2Br4 (25.0 mmol) added at -70°C; allowed to warm to ambient temp. for >18 h, H2O added, aq. phase separated, extracted with Et2O, dried over MgSO4, evaporated, chromd. (neutral alumina, hexane), FcH removed by sublimation; NMR;

A n/a B 36%

1,1,2,2-tetrabromoethane (79-27-6) + 5-bromo-2,9-di(undecan-6-yl)anthra[2,1,9-def:6,5,10-d'e'f']diisoquinoline-1,3,8,10(2H,9H)-tetraone (1309387-42-5) → helical PDI (1610377-74-6)

Conditions	Yield
With potassium acetate; palladium diacetate; potassium hydrogencarbonate In 1,4-dioxane; isopropyl alcohol at 110℃; for 10h; Schlenk technique; Inert atmosphere; Sealed tube;	30%

NH-pyrazole (288-13-1) + 1,1,2,2-tetrabromoethane (79-27-6) → 1,1,2,2-tetrakis(1H-pyrazol-1-yl)ethane + 1,1,2-tris(pyrazol-1-yl)ethene + (Z)-1,2-bis(1H-pyrazol-1-yl)ethylene (1313194-68-1) + 1,1-bis(pyrazol-1-yl)-2-bromoethene (1313194-72-7)

Conditions	Yield
Stage #1: NH-pyrazole With potassium hydroxide In dimethyl sulfoxide at 80℃; for 0.5h; Stage #2: 1,1,2,2-tetrabromoethane In dimethyl sulfoxide at 80℃; for 24h;	A 22% B n/a C n/a D n/a

1,1,2,2-tetrabromoethane (79-27-6) + bromoferrocene (1273-73-0) + 1,2-dibromoferrocene (238413-86-0) → 1,2,3-tribromoferrocene (1145715-22-5) + 1,2,3,4-tetrabromoferrocene

Conditions

Yield

With lithium tetramethylpiperidinide In tetrahydrofuran Schlenk techniques used under N2 or Ar, THF soln. of mixt. (12.0 mmol) of 1 (52%) and 2 (48%) added to LiTMP (6.00 mmol) in THF and stirred for 4 h at -30°C, C2H2Br4 (6.09 mmol) added at -78°C, allowed to warm to room temp. for >16 h; quenched with H2O, extracted with CH2Cl2, organic layer washed with H2O,dried over MgSO4, solvent removed under vac., chromd. (neutral alumina, hexane); not isolated, detected by NMR;

A 18% B 7%

1,1,2,2-tetrabromoethane (79-27-6) + bromoferrocene (1273-73-0) → 1,2-dibromoferrocene (238413-86-0) + 1,2,3,4,5-pentabromoferrocene (1145715-26-9)

Conditions

Yield

With lithium tetramethylpiperidinide In tetrahydrofuran Schlenk techniques used under N2 or Ar, THF soln. of 1 (4.76 mmol) addedto LiTMP (47.5 mmol) in THF and stirred for 5 h at -30°C, C2H2Br 4 (47.5 mmol) added at -78°C, allowed to warm to room temp. for >16 h; quenched with H2O, extracted with CH2Cl2, organic layer washed with aq. 1M HCl and H2O, dried over MgSO4, solvent removed under vac., chromd. (neutral alumina, hexane), concentrated, allowed to stand at 5°C for 16 h; elem.anal., XRD;

A n/a B 11%

pyridine (110-86-1) + 1,1,2,2-tetrabromoethane (79-27-6) → Pyridine hydrobromide (18820-82-1)

Conditions	Yield
With diethyl ether Irradiation.mit Sonnenlicht;

1,1,2,2-tetrabromoethane (79-27-6) + diethyl ether (60-29-7) + sodium ethanolate (141-52-6) → 1,1,2-tribromoethylene (598-16-3)

1,1,2,2-tetrabromoethane (79-27-6) + ethanol (64-17-5) + potassium acetate (127-08-2) → 1,1,2-tribromoethylene (598-16-3)

Conditions	Yield
at 120 - 140℃;

1,1,2,2-tetrabromoethane (79-27-6) + ethanol (64-17-5) + sodium trithiocarbonate (534-18-9) → cis+trans-dibromoethylene (540-49-8)

Upstream product

• 74-86-2 acetylene 
• 79-01-6 Trichloroethylene 
• 27001-65-6 2-propyl-1,3-oxathiolan 
• 16048-04-7 2-ethyl-[1,3]oxathiolane 
• 75-25-2 Bromoform 
• 18816-24-5 7,7-dimethyl-1,4,5,6-tetraphenyl-2,3-benzo-7-silanorbornadiene 
• 540-49-8 cis+trans-dibromoethylene 
• 71-43-2 benzene 
• 7727-15-3 aluminium bromide 
• 79-34-5 1,1,2,2-tetrachloroethane 
• 106-93-4 ethylene dibromide 
• 74-84-0 ethane 
• 75-62-7 Bromotrichloromethane 
• 83498-70-8 2-(hexyloxy)-1,3-dioxolane 

Downstream Products

• 598-16-3 1,1,2-tribromoethylene 
• 101-61-1 4,4'-methylene-bis(N,N-dimethylaniline) 
• 108-86-1 bromobenzene 
• 612-00-0 1,1'-ethylidenebis-benzene 
• 120-12-7 anthracene 
• 2294-94-2 1,1,1,2-tetraphenylethane 
• 632-50-8 1,1,2,2-tetraphenylethane 
• 16244-38-5 N¹,N²-di-p-tolyl-N-p-tolylglycineamidine 
• 75-95-6 1,1,1,2,2-pentabromoethane 
• 359-35-3 1,1,2,2-tetrafluoroethane 
• 430-90-0 1-Bromo-1,2,2-trifluoroethane 
• 74-85-1 ethene 
• 540-49-8 cis+trans-dibromoethylene 
• 74-83-9 methyl bromide 

Relevant articles and documents

The reaction of SF5Br with select 1,2-dihaloethylenes

SF5Br reacts with 1,2-haloethylenes (F, Cl, Br) in distinct ways. In the case of F- and Cl-olefins, the expected addition occurs while with 1,2-dibromoethylene a metathetical reaction yielding in a clean reaction a 1:1 mixture of SF5CH{double bond, long}CHBr and CHBr2CHBr2 is found. The mechanism for this reaction is discussed.

Laser Pulse Photolysis of 7-Silanorbornadiene in Solution: Experimental and AM1 Studies of Complexation between Silylenes and CHBr3

The quantum yield (0.95 +/- 0.1) for the decomposition of 7,7-dimethyl-1,4,5,6-tetraphenyl-2,3-benzo-7-silanorbornadiene (Ib) in hexane at room temperature has been determined by the laser pulse photolysis technique.Reaction rate constants of the generated dimethylsilylene with bromoform (4.4 * 107 M-1 s-1) and Ib (5.7 * 109 M-1 s-1) have been measured.It is suggested that the reaction of Me2Si: with CHBr3 occurs via the formation of an intermediate complex (λmax = 338 nm, ε =1280 M-1 cm-1).The bimolecular rate constant for decay of the complex (2k = 1.61 * 109 M-1 s-1) has also been estimated.Semi-empirical PM3 calculations of the model reaction between the singlet SiH2 and CHBr3 show the formation at the first step of the reaction of a donor-acceptor complex stabilized by interactions between a vacant p-AO of SiH2 and a lone pair of one of the Br atoms.Such a complex should be rather stable both toward dissociation into the starting reagents (E = 23.3 kcal/mol) and further rearrangement into the insertion product, Br(H2)SiCHBr2 (E = 22.3 kcal/mol).

HOMOLYTIC TRANSFORMATIONS OF 1,3-OXATHIOLANES IN THE PRESENCE OF POLYHALOMETHANES

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