Bromoform
trimethylsilyl bromide
A
trimethyl-tribromomethyl-silane
B
1,2-dibromomethane
Conditions | Yield |
---|---|
With hexaethylphosphoric triamide In diethyl ether at 20℃; for 1h; | A 82% B n/a |
Conditions | Yield |
---|---|
Stage #1: bis(thiocyanato)methane; sodium thiocyanide In methanol; water at 74 - 75℃; for 5h; Stage #2: With sodium hydrogencarbonate In methanol; water pH=6.3; Concentration; Solvent; | 79.3% |
Conditions | Yield |
---|---|
With bromine at 18 - 500℃; for 0.0166667h; Gas phase; | A 70.6% B 24.7% |
With hydrogen bromide; oxygen; Mg/Ru/SiO2 In water at 580℃; Conversion of starting material; | |
With hydrogen bromide; oxygen; Ba/Bi/Ru/SiO2 In water at 580 - 600℃; Conversion of starting material; |
Conditions | Yield |
---|---|
With calcium bromide; tetrahexylammonium bromide at 110℃; for 24h; | A 30% B 62% |
With ethyl bromide; aluminum oxide; tetrabutyl phosphonium bromide at 170℃; | A 49 % Spectr. B 25 % Spectr. |
With ethyl bromide at 170℃; Product distribution; var. of catalyst, reagent; | A 50 % Spectr. B 24 % Spectr. |
With ethyl bromide; aluminum oxide at 170℃; | A 66 % Spectr. B 14 % Spectr. |
2-ethoxy-1,3-dioxane
Bromoform
A
trimethylene carbonate
B
ethyl bromide
C
3-Brompropylformiat
D
acetaldehyde
F
1,2-dibromomethane
Conditions | Yield |
---|---|
dibenzoyl peroxide at 100℃; for 2h; Rate constant; Product distribution; other temperature; | A n/a B n/a C n/a D n/a E 60% F n/a |
Bromoform
2-(hexyloxy)-1,3-dioxolane
A
[1,3]-dioxolan-2-one
B
1-bromo-hexane
C
formic acid-(2-bromo-ethyl ester)
D
hexanal
F
1,2-dibromomethane
Conditions | Yield |
---|---|
dibenzoyl peroxide at 100℃; for 2h; Rate constant; Product distribution; other temperature; | A n/a B n/a C n/a D n/a E 60% F n/a |
chloro-trimethyl-silane
Bromoform
A
trimethyl-tribromomethyl-silane
B
1,2-dibromomethane
Conditions | Yield |
---|---|
With hexaethylphosphoric triamide In diethyl ether at 20℃; for 1h; | A 56% B n/a |
Bromoform
A
trimethylene carbonate
B
1-bromo-hexane
C
3-Brompropylformiat
D
hexanal
F
1,2-dibromomethane
Conditions | Yield |
---|---|
dibenzoyl peroxide at 100℃; for 2h; Rate constant; Product distribution; other temperature; | A n/a B n/a C n/a D n/a E 56% F n/a |
methane
A
methyl bromide
B
Bromoform
C
carbon tetrabromide
D
1,2-dibromomethane
Conditions | Yield |
---|---|
With bromine at 500℃; Product distribution; Further Variations:; Temperatures; Bromination; | A 17.4% B 0.48% C 2.5% D 5% |
Conditions | Yield |
---|---|
With bromine at 250℃; |
Conditions | Yield |
---|---|
at -50℃; |
methylene
dibromodichloromethane
A
1,1-Dichloroethylene
B
1,2-dibromomethane
Conditions | Yield |
---|---|
Tetrabrommethan,Bromoform und Jodoform reagieren analog; |
Conditions | Yield |
---|---|
With water; bromine | |
With bromine |
Conditions | Yield |
---|---|
With bromine at 400℃; |
Conditions | Yield |
---|---|
With aluminum tri-bromide | |
With aluminum tri-bromide; hydrogen bromide | |
With bromine; aluminium |
Conditions | Yield |
---|---|
With bromine; aluminium |
Bromoform
ethylmagnesium bromide
A
ethyl bromide
B
methane
C
3-ethylpentane
D
1,2-dibromomethane
Conditions | Yield |
---|---|
Produkt: Aethan, Acetylen; |
Conditions | Yield |
---|---|
With alkali sulfite | |
With phenylhydrazine | |
With alkaline potassium arsenite man destilliert das Reaktionsprodukt mit Wasserdampf; |
2,2,5,5-tetrabromo-1,6-diphenyl-hexane-1,3,4,6-tetraone
A
oxalic acid
B
benzoic acid
C
1,2-dibromomethane
Conditions | Yield |
---|---|
With bromine; pyrographite at 300℃; |
Conditions | Yield |
---|---|
Electrolysis; |
methylene
dibromodichloromethane
chlorobenzene
A
1,1-Dichloroethylene
B
1,2-dibromomethane
methylene
carbon tetrabromide
chlorobenzene
A
vinylidene dibromide
B
1,2-dibromomethane
2-ethoxy-1,3-dioxolane
Bromoform
A
[1,3]-dioxolan-2-one
B
ethyl bromide
C
formic acid-(2-bromo-ethyl ester)
D
2-bromoethyl ethyl carbonate
E
acetaldehyde
F
1,2-dibromomethane
Conditions | Yield |
---|---|
With dibenzoyl peroxide at 90℃; for 0.5h; Product distribution; | |
dibenzoyl peroxide at 100℃; for 2h; Rate constant; Product distribution; other temperature, other time; |
1-bromo-butane
dichloromethane
A
chlorobromomethane
B
n-Butyl chloride
C
1,2-dibromomethane
Conditions | Yield |
---|---|
aluminum oxide; tetrabutyl phosphonium bromide In gas at 150℃; Product distribution; effect of catalytic bed; |
2-phenyl-1,3-oxathiolane
A
1,1,2,2-tetrabromoethane
B
S-(2-bromoethyl) benzothioate
C
1,2-dibromomethane
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 |
ethyl bromide
dichloromethane
A
chloroethane
B
chlorobromomethane
C
1,2-dibromomethane
Conditions | Yield |
---|---|
aluminum oxide; tetrabutyl phosphonium bromide In gas at 150℃; Product distribution; effect of catalytic bed; |
Conditions | Yield |
---|---|
Stage #1: 1,2-dibromomethane With 2,2,6,6-tetramethylpiperidinylmagnesium chloride lithium chloride complex In tetrahydrofuran; toluene at -78℃; for 0.5h; Inert atmosphere; Stage #2: carbon dioxide In tetrahydrofuran; toluene at -78℃; for 3h; | 100% |
(i) nBuLi, CH2Cl2, THF, (ii) /BRN= 1900390/; Multistep reaction; |
Quinuclidine
1,2-dibromomethane
1-Bromomethyl-1-azonia-bicyclo[2.2.2]octane; bromide
Conditions | Yield |
---|---|
In acetonitrile at 30℃; under 750.06 Torr; for 3h; | 100% |
2-tert-butylcyclopentanone
1,2-dibromomethane
1-tert-butyl-2-methylene-cyclopentane
Conditions | Yield |
---|---|
With titanium tetrachloride; zinc In dichloromethane | 100% |
(S)-1,2,3,10,11,12-Hexamethoxy-7-methyl-7,8-dihydro-5H-dibenzo[a,c]cycloocten-6-one
1,2-dibromomethane
(S)-1,2,3,10,11,12-Hexamethoxy-6-methyl-7-methylene-5,6,7,8-tetrahydro-dibenzo[a,c]cyclooctene
Conditions | Yield |
---|---|
With titanium tetrachloride; zinc In dichloromethane for 0.25h; Ambient temperature; | 100% |
(4aR,6S,7R,8aS)-4-(4-methoxybenzyloxy)butyric acid 2,2-di(tert-butyl)-6-methyl-6-(2-methylallyl)-4,4a,6,7,8,8a-hexahydro-1,3,5-trioxa-2-silanaphthalen-7-yl ester
1,2-dibromomethane
(4aR,6S,7R,8aS)-2,2-di(tert-butyl)-7-{1-[3-(4-methoxybenzyloxy)propyl]vinyloxy}-6-methyl-6-(2-methylallyl)-4,4a,6,7,8,8a-hexahydro-1,3,5-trioxa-2-silanaphthalene
Conditions | Yield |
---|---|
With N,N,N,N,-tetramethylethylenediamine; titanium tetrachloride; zinc; lead(II) chloride In tetrahydrofuran; dichloromethane for 2h; Heating; | 100% |
Conditions | Yield |
---|---|
In tetrahydrofuran at 100℃; | 100% |
Inert atmosphere; Schlenk technique; | 99% |
at 70 - 80℃; | 81% |
5,5,9-trimethylspiro<5.5>undec-8-en-1-one
1,2-dibromomethane
3,7,7-trimethyl-11-methylenespiro[5.5]undec-2-ene
Conditions | Yield |
---|---|
With titanium tetrachloride; zinc In dichloromethane at 0 - 20℃; for 3h; | 100% |
5,5-dimethoxypentanoic acid 2,2-di-tert-butyl-6-methyl-6-(2-methylallyl)-hexahydro-1,3,5-trioxa-2-sila-naphthalen-7-yl ester
1,2-dibromomethane
C27H50O6Si
Conditions | Yield |
---|---|
With N,N,N,N,-tetramethylethylenediamine; titanium tetrachloride; zinc; lead(II) chloride In tetrahydrofuran; dichloromethane for 2h; | 100% |
4-[5-(3-benzyloxy-1-methylpropyl)-4-methyl-tetrahydro-furan-2-yl]-3-triisopropylsilanyloxy-butyric acid 2-but-3-enyl-10a,11a-dimethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-3-yl ester
1,2-dibromomethane
Conditions | Yield |
---|---|
With N,N,N,N,-tetramethylethylenediamine; titanium tetrachloride; zinc; lead(II) chloride In dichloromethane at 65℃; | 100% |
Conditions | Yield |
---|---|
In tetrahydrofuran at 100℃; | 100% |
Inert atmosphere; Schlenk technique; | 89% |
In tetrahydrofuran at 20 - 80℃; for 192h; | 87.6% |
In acetonitrile for 96h; Reflux; |
Conditions | Yield |
---|---|
Stage #1: C18H25BO3; 1,2-dibromomethane With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: With zinc(II) chloride In tetrahydrofuran; diethyl ether at -78 - 20℃; Inert atmosphere; enantioselective reaction; | 100% |
Conditions | Yield |
---|---|
In ethyl acetate for 120h; Reflux; | 100% |
Conditions | Yield |
---|---|
With caesium carbonate In N,N-dimethyl-formamide at 20℃; Inert atmosphere; | 100% |
3-formylphenyl acetate
3-acetylbenzaldehyde
1,2-dibromomethane
3-vinylphenyl acetate
Conditions | Yield |
---|---|
With acetic anhydride | 99.7% |
chloro-trimethyl-silane
1,2-dibromomethane
dibromobis(trimethylsilyl)methane
Conditions | Yield |
---|---|
With lithium diisopropyl amide In tetrahydrofuran; hexane; pentane 1.) -110 deg C, 20 min, 2.) -110 deg C to r.t., 12 h; | 99% |
With lithium diisopropyl amide In tetrahydrofuran at -78 - 20℃; | 88% |
With lithium diisopropyl amide In tetrahydrofuran at -100℃; | 60% |
(+)-(2,3-endo)-tert-butyldimethylsilyl 3-(1-oxopropyl)bicyclo<2.2.1>hept-5-ene-2-carboxylate
1,2-dibromomethane
(+)-(2,3-endo)-tert-butyldimethylsilyl 3-(1-methenylpropyl)bicyclo<2.2.1>hept-5-ene-2-carboxylate
Conditions | Yield |
---|---|
With titanium tetrachloride; zinc In tetrahydrofuran; dichloromethane at 20℃; for 0.5h; | 99% |
5'-(O-tert-butyl(dimethyl)silyl)-3'-ketothymidine
1,2-dibromomethane
1-[(2R,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-methylene-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione
Conditions | Yield |
---|---|
With titanium tetrachloride; zinc In tetrahydrofuran; dichloromethane for 2h; Ambient temperature; | 99% |
With titanium tetrachloride; zinc In tetrahydrofuran; dichloromethane |
Conditions | Yield |
---|---|
In tetrahydrofuran at 130℃; for 24h; | 99% |
Inert atmosphere; Schlenk technique; | 99% |
for 18h; Reflux; | 96% |
1,2-dibromomethane
methyl 5,6-dihydroxy-2-thien-2-ylpyrimidine-4-carboxylate
5-thiophen-2-yl-[1,3]dioxolo[4,5-d]pyrimidine-7-carboxylic acid methyl ester
Conditions | Yield |
---|---|
With potassium fluoride In N,N-dimethyl-formamide at 120℃; | 99% |
3-(5-chloro-2-methoxy-benzenesulfonylamino)-4-hydroxy-benzoic acid methyl ester
1,2-dibromomethane
3-(5-chloro-2-methoxy-benzenesulfonyl)-2,3-dihydro-benzooxazole-5-carboxylic acid methyl ester
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 48h; | 99% |
Conditions | Yield |
---|---|
In dimethyl sulfoxide DMSO added to suspn. of InBr in CH2Br2 at ca. -80°C, allowed to reach room temp. with stirring, further stirred for 1 h; evapd. in vac., oil solidified on stirring with petroleum ether, solid washed with Et2O, dried in vac.; elem. anal.; | 99% |
(CoH(NC5H4CH2CH2NHCH(CH3)C(CH3)NO)2)(2+)
1,2-dibromomethane
((CH2)Co(NC5H4CH2CH2NHCH(CH3)C(CH3)NO)2)(1+)*ClO4(1-)=((CH2)Co(NC5H4CH2CH2NHCH(CH3)C(CH3)NO)2)ClO4
Conditions | Yield |
---|---|
With NaBH4; PdCl2; NaOH In methanol; water soln. NaOH was added to suspn. Co(III) complex in MeOH under Ar, NaBH4 in water was added, PdCl2 in aq. HCl was added, after 15 min CH2Br2 was added; | 99% |
[Rh(triphenylphosphine)(C5Me5)((2,4,6-tri-tert-butylphenyl)phosphinidene)]
1,2-dibromomethane
Conditions | Yield |
---|---|
In pentane byproducts: ((CH3)3C)3C6H2PCH2; (N2 or Ar); treatment of soln. of Rh(PPh3)(C5Me5)(PC6H2(t-Bu)3) in n-pentane with small excess of CH2Br2 at room temp. for 12 h; pptn., decanting, washing with n-pentane; | 99% |
Conditions | Yield |
---|---|
With lithium diisopropyl amide In tetrahydrofuran at -78 - 20℃; Inert atmosphere; | 99% |
With lithium diisopropyl amide In tetrahydrofuran at -78 - 20℃; | 99% |
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile for 4h; Reflux; | 99% |
1,2-dibromomethane
Conditions | Yield |
---|---|
With palladium diacetate; tetra-(n-butyl)ammonium iodide; potassium carbonate; triethylamine; tris-(o-tolyl)phosphine In N,N-dimethyl acetamide at 90℃; for 12h; Schlenk technique; Inert atmosphere; Sealed tube; | 99% |
1,2-dibromomethane
Conditions | Yield |
---|---|
With palladium diacetate; tetra-(n-butyl)ammonium iodide; potassium carbonate; triethylamine; tris-(o-tolyl)phosphine In N,N-dimethyl acetamide at 90℃; for 12h; Schlenk technique; Inert atmosphere; Sealed tube; | 99% |
ethoxyethoxyethanol
1,2-dibromomethane
1,13-diethoxy-3,6,8,11-tetraoxa-tridecane
Conditions | Yield |
---|---|
With potassium hydroxide; tetrabutylammomium bromide In water; chlorobenzene at 50℃; for 0.5h; | 98.58% |
methyl 3-methylbutanoate
1,2-dibromomethane
l-methyl dl-2,2-dimethylcyclopropane-1-carboxylate
Conditions | Yield |
---|---|
With acetyl chloride; copper(l) chloride In dichloromethane for 12h; Reagent/catalyst; Reflux; | 98.2% |
Conditions | Yield |
---|---|
With anion exchange resin for 5h; Heating; | 98% |
With sodium hydroxide |
IUPAC Name: Dibromomethane
Empirical Formula: CH2Br2
Molecular Weight: 173.8346
Canonical SMILES: C(Br)Br
InChI: InChI=1S/CH2Br2/c2-1-3/h1H2
InChIKey: FJBFPHVGVWTDIP-UHFFFAOYSA-N
EINECS: 200-824-2
Product Categories: Pharmaceutical Intermediates; Organics; alpha,omega-Bifunctional Alkanes; alpha,omega-Dibromoalkanes; Monofunctional & alpha,omega-Bifunctional Alkanes; Analytical Chemistry; Standard Solution of Volatile Organic Compounds for Water & Soil Analysis; Standard Solutions (VOC); Alpha Sort; BromoVolatiles/ Semivolatiles; Chemical Class; D; DAlphabetic; DIA - DIC; Halogenated
storage temp.: Refrigerator
Water Solubility: 0.1 g/100 mL (20 ºC)
Stability: Stable. Incompatible with strong oxidizing agents, aluminium, magnesium. Reacts violently with potassium.
Index of Refraction: 1.532
Molar Refractivity: 22.14 cm3
Molar Volume: 71.4 cm3
Surface Tension: 37 dyne/cm
Density: 2.434 g/cm3
Flash Point: 96-98 °C
Enthalpy of Vaporization: 32.92 kJ/mol
Boiling Point: 97 °C at 760 mmHg
Vapour Pressure: 48.7 mmHg at 25 °C
Appearance: colourless liquid
Melting Point: -52 °C
Classification Code of Dibromomethane (CAS NO.74-95-3): Mutagens; Mutation data; Noxae; TSCA Flag T [Subject to the Section 4 test rule under TSCA]
Dibromomethane (CAS NO.74-95-3) is used as a solvent, gage fluid and in organic synthesis.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | subcutaneous | 3738mg/kg (3738mg/kg) | Toxicology and Applied Pharmacology. Vol. 4, Pg. 354, 1962. | |
rabbit | LD50 | oral | 1gm/kg (1000mg/kg) | Dow Chemical Company Reports. Vol. MSD-472, | |
rabbit | LD50 | skin | > 4gm/kg (4000mg/kg) | Dow Chemical Company Reports. Vol. MSD-472, | |
rabbit | LDLo | rectal | 5gm/kg (5000mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION | Journal of Pharmacology and Experimental Therapeutics. Vol. 34, Pg. 223, 1928. |
rat | LC50 | inhalation | 40gm/m3/2H (40000mg/m3) | "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 83, 1982. | |
rat | LD50 | oral | 108mg/kg (108mg/kg) | National Technical Information Service. Vol. PB85-143766 |
Community Right-To-Know List. Reported in EPA TSCA Inventory.
Hazard Codes: Xn,T,F
Risk Statements: 20-52/53-39/23/24/25-23/24/25-11
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.
R11:Highly flammable.
Safety Statements: 24-61-45-36/37-16-7
S24:Avoid contact with skin.
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.
S16:Keep away from sources of ignition.
S7:Keep container tightly closed.
RIDADR:UN 2664 6.1/PG 3
WGK Germany: 2
RTECS: PA7350000
HazardClass: 6.1
PackingGroup: III
A poison. Moderately toxic by subcutaneous route. Mildly toxic by inhalation. Mutation data reported. Mixtures with potassium explode on light impact. When heated to decomposition it emits toxic fumes of Br−.
DOT Classification: 6.1; Label: KEEP AWAY FROM FOOD
Dibromomethane (CAS NO.74-95-3), its Synonyms are Methylene bromide ; Methane, dibromo- ; Methylene bromide ; Methylene dibromide .
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