chloro-trimethyl-silane
iodoform
A
diiodomethane
B
trimethylsilyltriiodomethane
Conditions | Yield |
---|---|
With hexaethylphosphoric triamide In diethyl ether at 20℃; for 1h; | A n/a B 40% |
iodoform
A
diiodomethane
B
dichloroiodomethane
C
chlorodiiodomethane
Conditions | Yield |
---|---|
With mercury dichloride at 130℃; for 2h; Substitution; Title compound not separated from byproducts; | A 1% B 1% C 30% |
chloro-trimethyl-silane
iodoform
A
diiodomethane
B
(E)-1,2-bis(trimethylsilyl)ethene
C
(diiodomethyl)trimethylsilane
Conditions | Yield |
---|---|
With manganese In tetrahydrofuran at 25℃; for 1h; Product distribution; Further Variations:; Solvents; | A 3% B 3% C 21% |
diazomethane
diiodomethane
Conditions | Yield |
---|---|
With diethyl ether; iodine |
iodoform
sodium ethanolate
A
diiodomethane
B
2-ethoxypropionic acid
C
acrylic acid
Conditions | Yield |
---|---|
With ethanol |
Conditions | Yield |
---|---|
at 140 - 150℃; | |
With iodine at 140 - 150℃; | |
With sodium ethanolate |
Conditions | Yield |
---|---|
With acetone; sodium iodide | |
With sodium iodide; benzyl alcohol at 125℃; |
Conditions | Yield |
---|---|
With hydrogen iodide at 125℃; |
Conditions | Yield |
---|---|
Electrolysis; | |
With potassium peroxomonosulphate; water at 85℃; |
Conditions | Yield |
---|---|
at 135 - 150℃; |
methyl iodide
A
diiodomethane
B
iodoform
C
methane
D
ethane
Conditions | Yield |
---|---|
bei der Einwirkung von UV-Licht der Wellenlaengen 253.7 nm; Prod.5.:Aethylen, Prod.6.:Jod; |
Conditions | Yield |
---|---|
Photolysis; |
Methylenedioxybenzene
acetyl chloride
A
1-(benzo[d][1,3]dioxol-6-yl)ethanone
B
diiodomethane
C
dimethyl phthalate
D
3,4-diacetoxyacetophenone
Conditions | Yield |
---|---|
With sodium iodide In acetonitrile for 6h; Product distribution; Ambient temperature; | A n/a B 40 % Chromat. C 43 % Chromat. D n/a |
piperonal
acetyl chloride
A
diiodomethane
B
3,4-diacetoxybenzaldehyde
Conditions | Yield |
---|---|
With sodium iodide In acetonitrile for 15h; Product distribution; Ambient temperature; | A 38 % Chromat. B 40 % Chromat. C n/a |
iodoform
sodium thioethylate
A
diiodomethane
B
bis(ethylthio)methane
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide |
iodoform
A
diiodomethane
B
deuteriated methylene diiodide
C
diiodomethane-d2
Conditions | Yield |
---|---|
With water; water-d2 |
1,3-benzoxathiole
acetyl chloride
A
diiodomethane
B
2-hydroxythiophenol diacetic ester
Conditions | Yield |
---|---|
With sodium iodide In acetonitrile for 12h; Product distribution; Heating; | A 42 % Chromat. B 42 % Chromat. C n/a |
Conditions | Yield |
---|---|
neutral alumina 90 + Bu4P(1+)I(1-) In gas at 195℃; under 760 Torr; for 1.25h; | A 36 % Spectr. B 50 % Spectr. |
neutral alumina 90 + Bu4P(1+)I(1-) In gas at 195℃; under 760 Torr; | A 9 % Spectr. B 34 % Spectr. |
methyl iodide
A
diiodomethane
B
iodoform
C
methane
D
ethane
E
ethyl iodide
Conditions | Yield |
---|---|
With silver at -173.1℃; Product distribution; Irradiation; 248 nm photochemistry; |
diethyl ether
iodoform
diisopropyl hydrogenphosphonate
ammonia
diiodomethane
Conditions | Yield |
---|---|
at 200℃; |
Conditions | Yield |
---|---|
das aus der thermischen Zersetzung von Keten erhaltene Methylen reagiert; |
Conditions | Yield |
---|---|
das aus der thermischen Zersetzung von Keten erhaltene Methylen reagiert; |
Conditions | Yield |
---|---|
In acetonitrile at 28℃; under 3750300 Torr; for 19h; | 100% |
92% | |
With hydroquinone In ethyl acetate at 20℃; for 48h; Alkylation; | 47.7% |
With ethanol at 100℃; im geschlossenen Rohr; |
diiodomethane
ethyl 6-ethoxymethylene-2-methylcyclohex-2-enecarboxylate
1-ethoxy-4-ethoxycarbonyl-5-methylspiro<2.5>oct-5-ene
Conditions | Yield |
---|---|
With zinc copper; iodine In diethyl ether for 24.5h; Heating; | 100% |
With zinc In diethyl ether |
Quinuclidine
diiodomethane
1-Iodomethyl-1-azonia-bicyclo[2.2.2]octane; iodide
Conditions | Yield |
---|---|
In methanol at 28℃; under 3750300 Torr; for 2h; | 100% |
diiodomethane
7-methylenedispiro<2.0.2.1>heptane
trispiro<2.0.2.0.2.0>nonane
Conditions | Yield |
---|---|
With silver; zinc | 100% |
With copper; zinc Yield given; |
diiodomethane
5,10,15-trimethylenetrispiro<3.1.3.1.3.1>pentadecane
hexaspiro<2.0.3.0.2.0.3.0.2.0.3.0>heneicosane
Conditions | Yield |
---|---|
With silver; zinc In diethyl ether at 60℃; for 1h; | 100% |
Conditions | Yield |
---|---|
With samarium diiodide; Isopropanol-d1 In tetrahydrofuran at 0℃; with Sm or MeOD; | 100% |
diiodomethane
1-phenyl-3,4-dihydronaphthalene
7b-Phenyl-1a,2,3,7b-tetrahydro-1H-cyclopropanaphthalin
Conditions | Yield |
---|---|
With diethylzinc; N-[(Phenylmethoxy)carbonyl]-L-valyl-L-proline methyl ester In dichloromethane at 0℃; for 16h; Product distribution / selectivity; Simmons-Smith Reaction; | 100% |
With C26H30N2O5; diethylzinc In dichloromethane at 0℃; for 16h; Product distribution / selectivity; Simmons-Smith Reaction; | 100% |
With C19H34N2O7; diethylzinc In dichloromethane at 0℃; for 16h; Product distribution / selectivity; Simmons-Smith Reaction; | 97% |
Conditions | Yield |
---|---|
With trimethylaluminum In dichloromethane for 10h; Heating; | 100% |
With diethylzinc In 1,2-dichloro-ethane; toluene at 20℃; | 40% |
Stage #1: diiodomethane With diethylzinc; trifluoroacetic acid In n-heptane; dichloromethane at -10 - 10℃; for 1h; Stage #2: 5-Hexen-1-ol In n-heptane; dichloromethane at 0 - 20℃; for 1.5h; | |
With diethylzinc; trifluoroacetic acid In hexane; dichloromethane at 0 - 20℃; for 24h; Inert atmosphere; | |
With trimethylaluminum In hexane; dichloromethane at 20 - 40℃; |
diiodomethane
methyl (Z)-vaccenate
Conditions | Yield |
---|---|
With diethylzinc In benzene at 65℃; for 6h; | 100% |
diiodomethane
(E)-6-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)hex-2-en-1-ol
{(1S,2R)-2-[3-(tert-butyldiphenylsilanyloxy)propyl]cyclopropyl}methanol
Conditions | Yield |
---|---|
With (R,R)-tartaric acid deriv.-B-n-butyl dioxaborolane; diethylzinc In 1,2-dimethoxyethane; dichloromethane at -15℃; for 2h; Charette asymmetric cyclopropanation; | 100% |
diiodomethane
(+/-)-(1RS,4SR)acetic acid 4-acetylamido-cyclopent-2-enyl-methyl ester
Conditions | Yield |
---|---|
With diethylzinc In dichloromethane at 0 - 20℃; for 19h; Simmons-Smith reaction; | 100% |
diiodomethane
Conditions | Yield |
---|---|
With diethylzinc In tetrahydrofuran Simmons-Smith cyclopropanation; | 100% |
Stage #1: (5SR,7aSR)-7a-prop-2'-ynyl-2,3,5,6,7,7a-hexahydro-1H-inden-5-ol With diethylzinc In diethyl ether; hexane at 0℃; for 0.0833333h; Stage #2: diiodomethane In diethyl ether; hexane at 20℃; | 100% |
diiodomethane
methyl 2,6-di-O-benzyl-4-deoxy-α-L-threo-hex-4-enopyranoside
Conditions | Yield |
---|---|
With diethylzinc In diethyl ether Simmons-Smith reaction; | 100% |
With diethylzinc In diethyl ether; hexane at 40℃; for 2h; | 97% |
1-(tetrahydropyran-2'-yloxy)tetradec-10-(Z)-en-12-ol
diiodomethane
Conditions | Yield |
---|---|
With diethylzinc; trifluoroacetic acid In dichloromethane at 0℃; for 1h; Simmons-Smith cyclopropanation; | 100% |
Conditions | Yield |
---|---|
With diethylzinc; trifluoroacetic acid In dichloromethane at 0℃; for 1h; Simmons-Smith cyclopropanation; | 100% |
diiodomethane
Conditions | Yield |
---|---|
Stage #1: (5SR,7aSR)-7a-allyl-2,3,5,6,7,7a-hexahydro-1H-inden-5-ol With diethylzinc In diethyl ether; hexane at 0℃; for 0.0833333h; Stage #2: diiodomethane In diethyl ether; hexane at 20℃; | 100% |
diiodomethane
Conditions | Yield |
---|---|
Stage #1: (5SR,7aRS)-7a-but-3'-ynyl-2,3,5,6,7,7a-hexahydro-1H-inden-5-ol With diethylzinc In diethyl ether; hexane at 0℃; for 0.0833333h; Stage #2: diiodomethane In diethyl ether; hexane at 20℃; | 100% |
Conditions | Yield |
---|---|
With diethylzinc; trifluoroacetic acid In dichloromethane at 0 - 20℃; for 48.67h; | 100% |
6-methoxy-3-pyridinecarboxaldehyde
diiodomethane
2-methoxy-5-oxiranyl-pyridine
Conditions | Yield |
---|---|
With methyllithium lithium bromide In tetrahydrofuran; diethyl ether at 0 - 25℃; for 2h; | 100% |
methyl 2-[1-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)vinyl]phenylcarboxylate
diiodomethane
Methyl 2-[1-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)cyclopropyl]benzoate
Conditions | Yield |
---|---|
In n-heptane; dichloromethane | 100% |
methyl 3-[1-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)vinyl]phenylcarboxylate
diiodomethane
Methyl 3-[1-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)cyclopropyl]benzoate
Conditions | Yield |
---|---|
In n-heptane; dichloromethane | 100% |
diiodomethane
E-1-tributylstannyl-3-hydroxy-1-octene
Conditions | Yield |
---|---|
With diethylzinc In toluene under Ar; | 100% |
diiodomethane
3-naphthalen-2-yl-cyclopent-2-enol
5-naphthalen-2-yl-bicyclo[3.1.0]hexan-2-ol
Conditions | Yield |
---|---|
Stage #1: 3-naphthalen-2-yl-cyclopent-2-enol With diethylzinc In dichloromethane for 0.166667h; Stage #2: diiodomethane In dichloromethane at 0 - 20℃; for 2.16667h; | 100% |
Conditions | Yield |
---|---|
Stage #1: diiodomethane With diethylzinc; trifluoroacetic acid In dichloromethane at 0℃; for 0.666667h; Stage #2: 3-bromobut-3-en-1-ol In dichloromethane at 0 - 20℃; for 4h; | 100% |
diiodomethane
(S,E)-5-(tert-butyldimethylsilyloxy)-5-(1,2-dimethyl-1H-benzo[d]imidazol-5-yl)pent-2-en-1-ol
(1R,2S)-2-((S)-2-(tert-butyldimethylsilyloxy)-2-(1,2-dimethyl-1H-benzo[d]imidazol-5-yl)ethyl)cyclopropanemethanol
Conditions | Yield |
---|---|
Stage #1: diiodomethane With diethylzinc In hexane; dichloromethane at 0℃; for 0.166667h; Stage #2: (S,E)-5-(tert-butyldimethylsilyloxy)-5-(1,2-dimethyl-1H-benzo[d]imidazol-5-yl)pent-2-en-1-ol With (4S,5S)-2-butyl-N4,N4,N5,N5-tetramethyl-1,3,2-dioxaborolane-4,5-dicarboxamide In hexane; dichloromethane at 0 - 20℃; Charette cyclopropanation; stereoselective reaction; | 100% |
With diethylzinc; (4S,5S)-2-butyl-N4,N4,N5,N5-tetramethyl-1,3,2-dioxaborolane-4,5-dicarboxamide In dichloromethane at 0 - 20℃; | 100% |
methyl cyclohexylcarboxylate
diiodomethane
Methyl 1-iodomethylcyclohexanecarboxylate
Conditions | Yield |
---|---|
Stage #1: methyl cyclohexylcarboxylate With lithium diisopropyl amide In tetrahydrofuran at -78℃; Stage #2: diiodomethane In tetrahydrofuran at -10 - 20℃; for 18h; | 100% |
Stage #1: methyl cyclohexylcarboxylate With lithium diisopropyl amide Stage #2: diiodomethane | 65% |
diiodomethane
4,4-diphenylcyclohex-1-ene
Conditions | Yield |
---|---|
Stage #1: diiodomethane With diethylzinc In hexane; dichloromethane at -78 - 0℃; for 0.25h; Stage #2: With trifluoroacetic acid In hexane; dichloromethane at 0℃; for 0.25h; Stage #3: 4,4-diphenylcyclohex-1-ene In hexane; dichloromethane at 20℃; for 1h; Simmons-Smith reaction; diastereoselective reaction; | 100% |
Conditions | Yield |
---|---|
Stage #1: diiodomethane With diethylzinc In hexane; dichloromethane at -78 - 0℃; for 0.25h; Stage #2: (RS)-N-(cyclohex-2-en-1-yl)benzamide In hexane; dichloromethane at 20℃; for 1h; Simmons-Smith reaction; diastereoselective reaction; | 100% |
diiodomethane
methyl 4-[(cyclopropyloxy)methyl]benzoate
Conditions | Yield |
---|---|
With diethylzinc In dichloromethane at 15 - 30℃; for 3h; | 100% |
diiodomethane
2,2-difluoro-4-pentenoic acid ethyl ester
ethyl 3-cyclopropyl-2,2-difluoropropanoate
Conditions | Yield |
---|---|
Stage #1: diiodomethane With diethylzinc; trifluoroacetic acid In hexane; dichloromethane at -5 - 0℃; for 0.833333h; Stage #2: 2,2-difluoro-4-pentenoic acid ethyl ester In hexane; dichloromethane for 16.42h; Product distribution / selectivity; Cooling; Reflux; | 100% |
Diiodomethane is used with its high specific gravity for the separation of minerals or for determination of specific gravity of mineral particles.
Diiodomethane is also used as a solvent and can be a reaction intermediate in the Simmons-Smith reaction, ect.
Diiodomethane is commercially available. It may also be prepared by reducing iodoform with sodium arsenite:
CHI3 + Na3AsO3 + NaOH → CH2I2 + NaI + Na3AsO4
1. | orl-cld LDLo:2778 µL/kg:BAH,PUL | AEMED3 Annals of Emergency Medicine. 19 (1990),1171. | ||
2. | ipr-rat LD50:403 mg/kg | 34ZIAG Toxicology of Drugs and Chemicals ,Deichmann, W.B.,New York, NY.: Academic Press, Inc.,1969,756. | ||
3. | ipr-mus LD50:467 mg/kg | 34ZIAG Toxicology of Drugs and Chemicals ,Deichmann, W.B.,New York, NY.: Academic Press, Inc.,1969,756. | ||
4. | scu-mus LD50:830 mg/kg | TXAPA9 Toxicology and Applied Pharmacology. 4 (1962),354. |
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