Product Name

  • Name

    Diiodomethane

  • EINECS 200-841-5
  • CAS No. 75-11-6
  • Article Data67
  • CAS DataBase
  • Density 3.238 g/cm3
  • Solubility water: 14 g/L (20 °C)
  • Melting Point 6 °C
  • Formula CH2I2
  • Boiling Point 182 °C at 760 mmHg
  • Molecular Weight 267.836
  • Flash Point 76.6 °C
  • Transport Information
  • Appearance light yellow or gold liquid with chloroform-like odour
  • Safety 26-37/39
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 75-11-6 (Diiodomethane)
  • Hazard Symbols IrritantXi
  • Synonyms Methylene diiodide;Methylene iodide;NSC 35804;
  • PSA 0.00000
  • LogP 1.81390

Synthetic route

chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

iodoform
75-47-8

iodoform

A

diiodomethane
75-11-6

diiodomethane

B

trimethylsilyltriiodomethane
128530-64-3

trimethylsilyltriiodomethane

Conditions
ConditionsYield
With hexaethylphosphoric triamide In diethyl ether at 20℃; for 1h;A n/a
B 40%
iodoform
75-47-8

iodoform

A

diiodomethane
75-11-6

diiodomethane

B

dichloroiodomethane
594-04-7

dichloroiodomethane

C

chlorodiiodomethane
638-73-3

chlorodiiodomethane

Conditions
ConditionsYield
With mercury dichloride at 130℃; for 2h; Substitution; Title compound not separated from byproducts;A 1%
B 1%
C 30%
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

iodoform
75-47-8

iodoform

A

diiodomethane
75-11-6

diiodomethane

B

(E)-1,2-bis(trimethylsilyl)ethene
18178-59-1

(E)-1,2-bis(trimethylsilyl)ethene

C

(diiodomethyl)trimethylsilane
29955-07-5

(diiodomethyl)trimethylsilane

Conditions
ConditionsYield
With manganese In tetrahydrofuran at 25℃; for 1h; Product distribution; Further Variations:; Solvents;A 3%
B 3%
C 21%
diiodomethane
75-11-6

diiodomethane

Conditions
ConditionsYield
With diethyl ether; iodine
iodoform
75-47-8

iodoform

sodium ethanolate
141-52-6

sodium ethanolate

A

diiodomethane
75-11-6

diiodomethane

B

2-ethoxypropionic acid
53103-75-6

2-ethoxypropionic acid

C

acrylic acid
79-10-7

acrylic acid

iodoform
75-47-8

iodoform

sodium acetate
127-09-3

sodium acetate

diiodomethane
75-11-6

diiodomethane

Conditions
ConditionsYield
With ethanol
iodoform
75-47-8

iodoform

diiodomethane
75-11-6

diiodomethane

Conditions
ConditionsYield
at 140 - 150℃;
With iodine at 140 - 150℃;
With sodium ethanolate
dichloromethane
75-09-2

dichloromethane

diiodomethane
75-11-6

diiodomethane

Conditions
ConditionsYield
With acetone; sodium iodide
With sodium iodide; benzyl alcohol at 125℃;
chloroform
67-66-3

chloroform

diiodomethane
75-11-6

diiodomethane

Conditions
ConditionsYield
With hydrogen iodide at 125℃;
Iodoacetic acid
64-69-7

Iodoacetic acid

diiodomethane
75-11-6

diiodomethane

Conditions
ConditionsYield
Electrolysis;
With potassium peroxomonosulphate; water at 85℃;
iodoform
75-47-8

iodoform

acetone
67-64-1

acetone

diiodomethane
75-11-6

diiodomethane

Conditions
ConditionsYield
at 135 - 150℃;
methyl iodide
74-88-4

methyl iodide

A

diiodomethane
75-11-6

diiodomethane

B

iodoform
75-47-8

iodoform

C

methane
34557-54-5

methane

D

ethane
74-84-0

ethane

Conditions
ConditionsYield
bei der Einwirkung von UV-Licht der Wellenlaengen 253.7 nm; Prod.5.:Aethylen, Prod.6.:Jod;
methyl iodide
74-88-4

methyl iodide

A

diiodomethane
75-11-6

diiodomethane

B

methane
34557-54-5

methane

C

ethane
74-84-0

ethane

Conditions
ConditionsYield
Photolysis;
methylene
2465-56-7

methylene

iodoform
75-47-8

iodoform

benzene
71-43-2

benzene

A

diiodomethane
75-11-6

diiodomethane

B

vinyliodide
593-66-8

vinyliodide

Methylenedioxybenzene
274-09-9

Methylenedioxybenzene

acetyl chloride
75-36-5

acetyl chloride

A

1-(benzo[d][1,3]dioxol-6-yl)ethanone
3162-29-6

1-(benzo[d][1,3]dioxol-6-yl)ethanone

B

diiodomethane
75-11-6

diiodomethane

C

dimethyl phthalate
635-67-6

dimethyl phthalate

D

3,4-diacetoxyacetophenone
72712-21-1

3,4-diacetoxyacetophenone

Conditions
ConditionsYield
With sodium iodide In acetonitrile for 6h; Product distribution; Ambient temperature;A n/a
B 40 % Chromat.
C 43 % Chromat.
D n/a
piperonal
120-57-0

piperonal

acetyl chloride
75-36-5

acetyl chloride

A

diiodomethane
75-11-6

diiodomethane

B

3,4-diacetoxybenzaldehyde
67727-64-4

3,4-diacetoxybenzaldehyde

C

Acetic acid 2-acetoxy-4-acetyl-5-formyl-phenyl ester

Acetic acid 2-acetoxy-4-acetyl-5-formyl-phenyl ester

Conditions
ConditionsYield
With sodium iodide In acetonitrile for 15h; Product distribution; Ambient temperature;A 38 % Chromat.
B 40 % Chromat.
C n/a
iodoform
75-47-8

iodoform

sodium thioethylate
811-51-8

sodium thioethylate

A

diiodomethane
75-11-6

diiodomethane

B

bis(ethylthio)methane
4396-19-4

bis(ethylthio)methane

Conditions
ConditionsYield
In N,N-dimethyl-formamide
iodoform
75-47-8

iodoform

A

diiodomethane
75-11-6

diiodomethane

B

deuteriated methylene diiodide
2253-85-2

deuteriated methylene diiodide

C

diiodomethane-d2
15729-58-5

diiodomethane-d2

Conditions
ConditionsYield
With water; water-d2
1,3-benzoxathiole
274-26-0

1,3-benzoxathiole

acetyl chloride
75-36-5

acetyl chloride

A

diiodomethane
75-11-6

diiodomethane

B

2-hydroxythiophenol diacetic ester
73726-60-0

2-hydroxythiophenol diacetic ester

C

Acetic acid 4-acetyl-2-acetylsulfanyl-phenyl ester

Acetic acid 4-acetyl-2-acetylsulfanyl-phenyl ester

Conditions
ConditionsYield
With sodium iodide In acetonitrile for 12h; Product distribution; Heating;A 42 % Chromat.
B 42 % Chromat.
C n/a
dichloromethane
75-09-2

dichloromethane

methyl iodide
74-88-4

methyl iodide

A

diiodomethane
75-11-6

diiodomethane

B

Chloroiodomethane
593-71-5

Chloroiodomethane

Conditions
ConditionsYield
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.
iodine
7553-56-2

iodine

A

diiodomethane
75-11-6

diiodomethane

B

nitrogen

nitrogen

methyl iodide
74-88-4

methyl iodide

A

diiodomethane
75-11-6

diiodomethane

B

iodoform
75-47-8

iodoform

C

methane
34557-54-5

methane

D

ethane
74-84-0

ethane

E

ethyl iodide
75-03-6

ethyl iodide

F

I2

I2

Conditions
ConditionsYield
With silver at -173.1℃; Product distribution; Irradiation; 248 nm photochemistry;
diethyl ether
60-29-7

diethyl ether

iodoform
75-47-8

iodoform

diisopropyl hydrogenphosphonate
1809-20-7

diisopropyl hydrogenphosphonate

ammonia
7664-41-7

ammonia

diiodomethane
75-11-6

diiodomethane

chloroform
67-66-3

chloroform

hydrogen iodide
10034-85-2

hydrogen iodide

diiodomethane
75-11-6

diiodomethane

dichloromethane
75-09-2

dichloromethane

iodine
7553-56-2

iodine

diiodomethane
75-11-6

diiodomethane

Conditions
ConditionsYield
at 200℃;
methylene
2465-56-7

methylene

chloroform
67-66-3

chloroform

iodine
7553-56-2

iodine

diiodomethane
75-11-6

diiodomethane

Conditions
ConditionsYield
das aus der thermischen Zersetzung von Keten erhaltene Methylen reagiert;
methylene
2465-56-7

methylene

iodine
7553-56-2

iodine

acetone
67-64-1

acetone

diiodomethane
75-11-6

diiodomethane

Conditions
ConditionsYield
das aus der thermischen Zersetzung von Keten erhaltene Methylen reagiert;
iodo(iodomethoxy)methane
60833-52-5

iodo(iodomethoxy)methane

AlI3

AlI3

diiodomethane
75-11-6

diiodomethane

iodoform
75-47-8

iodoform

aqueous Na3AsO3

aqueous Na3AsO3

diiodomethane
75-11-6

diiodomethane

diiodomethane
75-11-6

diiodomethane

triethylamine
121-44-8

triethylamine

1-iodo-N,N,N-triethylmethaniminium iodide
104304-17-8

1-iodo-N,N,N-triethylmethaniminium iodide

Conditions
ConditionsYield
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
75-11-6

diiodomethane

ethyl 6-ethoxymethylene-2-methylcyclohex-2-enecarboxylate
79236-19-4, 79236-25-2

ethyl 6-ethoxymethylene-2-methylcyclohex-2-enecarboxylate

1-ethoxy-4-ethoxycarbonyl-5-methylspiro<2.5>oct-5-ene
37850-36-5

1-ethoxy-4-ethoxycarbonyl-5-methylspiro<2.5>oct-5-ene

Conditions
ConditionsYield
With zinc copper; iodine In diethyl ether for 24.5h; Heating;100%
With zinc In diethyl ether
Quinuclidine
100-76-5

Quinuclidine

diiodomethane
75-11-6

diiodomethane

1-Iodomethyl-1-azonia-bicyclo[2.2.2]octane; iodide
104304-18-9

1-Iodomethyl-1-azonia-bicyclo[2.2.2]octane; iodide

Conditions
ConditionsYield
In methanol at 28℃; under 3750300 Torr; for 2h;100%
diiodomethane
75-11-6

diiodomethane

7-methylenedispiro<2.0.2.1>heptane
50874-25-4

7-methylenedispiro<2.0.2.1>heptane

trispiro<2.0.2.0.2.0>nonane
31561-59-8

trispiro<2.0.2.0.2.0>nonane

Conditions
ConditionsYield
With silver; zinc100%
With copper; zinc Yield given;
diiodomethane
75-11-6

diiodomethane

5,10,15-trimethylenetrispiro<3.1.3.1.3.1>pentadecane
94834-84-1

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
94834-85-2

hexaspiro<2.0.3.0.2.0.3.0.2.0.3.0>heneicosane

Conditions
ConditionsYield
With silver; zinc In diethyl ether at 60℃; for 1h;100%
diiodomethane
75-11-6

diiodomethane

<2H1>methyl iodide
992-96-1

<2H1>methyl iodide

Conditions
ConditionsYield
With samarium diiodide; Isopropanol-d1 In tetrahydrofuran at 0℃; with Sm or MeOD;100%
diiodomethane
75-11-6

diiodomethane

1-phenyl-3,4-dihydronaphthalene
7469-40-1

1-phenyl-3,4-dihydronaphthalene

7b-Phenyl-1a,2,3,7b-tetrahydro-1H-cyclopropanaphthalin
34566-29-5

7b-Phenyl-1a,2,3,7b-tetrahydro-1H-cyclopropanaphthalin

Conditions
ConditionsYield
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%
5-Hexen-1-ol
821-41-0

5-Hexen-1-ol

diiodomethane
75-11-6

diiodomethane

4-cyclopropylbutan-1-ol
5687-83-2

4-cyclopropylbutan-1-ol

Conditions
ConditionsYield
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
75-11-6

diiodomethane

methyl (Z)-vaccenate
6198-58-9, 52380-33-3, 1937-63-9

methyl (Z)-vaccenate

Methyl cis-11,12-methyleneoctadecanoate

Methyl cis-11,12-methyleneoctadecanoate

Conditions
ConditionsYield
With diethylzinc In benzene at 65℃; for 6h;100%
diiodomethane
75-11-6

diiodomethane

(E)-6-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)hex-2-en-1-ol
111649-71-9

(E)-6-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)hex-2-en-1-ol

{(1S,2R)-2-[3-(tert-butyldiphenylsilanyloxy)propyl]cyclopropyl}methanol
392336-20-8

{(1S,2R)-2-[3-(tert-butyldiphenylsilanyloxy)propyl]cyclopropyl}methanol

Conditions
ConditionsYield
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
75-11-6

diiodomethane

(+/-)-(1RS,4SR)acetic acid 4-acetylamido-cyclopent-2-enyl-methyl ester
61865-50-7

(+/-)-(1RS,4SR)acetic acid 4-acetylamido-cyclopent-2-enyl-methyl ester

(+/-)-cis-endo-acetic acid 4-acetylamino-bicyclo[3.1.0]hex-2-yl methyl ester

(+/-)-cis-endo-acetic acid 4-acetylamino-bicyclo[3.1.0]hex-2-yl methyl ester

Conditions
ConditionsYield
With diethylzinc In dichloromethane at 0 - 20℃; for 19h; Simmons-Smith reaction;100%
diiodomethane
75-11-6

diiodomethane

(5SR,7aSR)-7a-prop-2'-ynyl-2,3,5,6,7,7a-hexahydro-1H-inden-5-ol

(5SR,7aSR)-7a-prop-2'-ynyl-2,3,5,6,7,7a-hexahydro-1H-inden-5-ol

(1aRS,2SR,4aSR,7aSR)-4a-prop-2'-ynyloctahydro-1H-cyclopropa[d]inden-2-ol

(1aRS,2SR,4aSR,7aSR)-4a-prop-2'-ynyloctahydro-1H-cyclopropa[d]inden-2-ol

Conditions
ConditionsYield
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
75-11-6

diiodomethane

methyl 2,6-di-O-benzyl-4-deoxy-α-L-threo-hex-4-enopyranoside
134039-06-8

methyl 2,6-di-O-benzyl-4-deoxy-α-L-threo-hex-4-enopyranoside

(1R,3R,4R,5S,6R)-4-(benzyloxy)-1-[(benzyloxy)methyl]-3-methoxy-2-oxabicyclo[4.1.0]heptan-5-ol

(1R,3R,4R,5S,6R)-4-(benzyloxy)-1-[(benzyloxy)methyl]-3-methoxy-2-oxabicyclo[4.1.0]heptan-5-ol

Conditions
ConditionsYield
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
850722-93-9

1-(tetrahydropyran-2'-yloxy)tetradec-10-(Z)-en-12-ol

diiodomethane
75-11-6

diiodomethane

9-(2-(1-hydroxypropyl)cyclopropyl)-1-(tetrahydropyran-2'-yloxy)nonane

9-(2-(1-hydroxypropyl)cyclopropyl)-1-(tetrahydropyran-2'-yloxy)nonane

Conditions
ConditionsYield
With diethylzinc; trifluoroacetic acid In dichloromethane at 0℃; for 1h; Simmons-Smith cyclopropanation;100%
diiodomethane
75-11-6

diiodomethane

(E)-10-tetradecene-1-ol
64437-35-0

(E)-10-tetradecene-1-ol

9-(2-propylcyclopropyl)nonan-1-ol

9-(2-propylcyclopropyl)nonan-1-ol

Conditions
ConditionsYield
With diethylzinc; trifluoroacetic acid In dichloromethane at 0℃; for 1h; Simmons-Smith cyclopropanation;100%
(5SR,7aSR)-7a-allyl-2,3,5,6,7,7a-hexahydro-1H-inden-5-ol

(5SR,7aSR)-7a-allyl-2,3,5,6,7,7a-hexahydro-1H-inden-5-ol

diiodomethane
75-11-6

diiodomethane

(1aRS,2SR,4aSR,7aSR)-4a-allyloctahydro-1H-cyclopropa[d]inden-2-ol

(1aRS,2SR,4aSR,7aSR)-4a-allyloctahydro-1H-cyclopropa[d]inden-2-ol

Conditions
ConditionsYield
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%
(5SR,7aRS)-7a-but-3'-ynyl-2,3,5,6,7,7a-hexahydro-1H-inden-5-ol

(5SR,7aRS)-7a-but-3'-ynyl-2,3,5,6,7,7a-hexahydro-1H-inden-5-ol

diiodomethane
75-11-6

diiodomethane

(1aRS,2SR,4aRS,7aSR)-4a-but-3'-ynyloctahydro-1H-cyclopropa[d]inden-2-ol

(1aRS,2SR,4aRS,7aSR)-4a-but-3'-ynyloctahydro-1H-cyclopropa[d]inden-2-ol

Conditions
ConditionsYield
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%
C19H22F3NO5
1000894-33-6

C19H22F3NO5

diiodomethane
75-11-6

diiodomethane

C20H24F3NO5
1000894-56-3

C20H24F3NO5

Conditions
ConditionsYield
With diethylzinc; trifluoroacetic acid In dichloromethane at 0 - 20℃; for 48.67h;100%
6-methoxy-3-pyridinecarboxaldehyde
65873-72-5

6-methoxy-3-pyridinecarboxaldehyde

diiodomethane
75-11-6

diiodomethane

2-methoxy-5-oxiranyl-pyridine
890037-92-0

2-methoxy-5-oxiranyl-pyridine

Conditions
ConditionsYield
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
208186-22-5

methyl 2-[1-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)vinyl]phenylcarboxylate

diiodomethane
75-11-6

diiodomethane

Methyl 2-[1-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)cyclopropyl]benzoate
208186-35-0

Methyl 2-[1-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)cyclopropyl]benzoate

Conditions
ConditionsYield
In n-heptane; dichloromethane100%
methyl 3-[1-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)vinyl]phenylcarboxylate
208186-25-8

methyl 3-[1-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)vinyl]phenylcarboxylate

diiodomethane
75-11-6

diiodomethane

Methyl 3-[1-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)cyclopropyl]benzoate
208186-37-2

Methyl 3-[1-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)cyclopropyl]benzoate

Conditions
ConditionsYield
In n-heptane; dichloromethane100%
diiodomethane
75-11-6

diiodomethane

E-1-tributylstannyl-3-hydroxy-1-octene
79970-81-3, 79970-82-4, 150199-03-4

E-1-tributylstannyl-3-hydroxy-1-octene

(1RS)-1-[(1RS,2SR)-2-(tributylstannyl)cyclopropyl]hexan-1-ol

(1RS)-1-[(1RS,2SR)-2-(tributylstannyl)cyclopropyl]hexan-1-ol

Conditions
ConditionsYield
With diethylzinc In toluene under Ar;100%
diiodomethane
75-11-6

diiodomethane

3-naphthalen-2-yl-cyclopent-2-enol
1026667-70-8

3-naphthalen-2-yl-cyclopent-2-enol

5-naphthalen-2-yl-bicyclo[3.1.0]hexan-2-ol
1026667-71-9

5-naphthalen-2-yl-bicyclo[3.1.0]hexan-2-ol

Conditions
ConditionsYield
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%
diiodomethane
75-11-6

diiodomethane

3-bromobut-3-en-1-ol
76334-36-6

3-bromobut-3-en-1-ol

2-(1-bromocyclopropyl)-ethanol
923032-63-7

2-(1-bromocyclopropyl)-ethanol

Conditions
ConditionsYield
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
75-11-6

diiodomethane

(S,E)-5-(tert-butyldimethylsilyloxy)-5-(1,2-dimethyl-1H-benzo[d]imidazol-5-yl)pent-2-en-1-ol
1016895-49-0

(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
1016895-50-3

(1R,2S)-2-((S)-2-(tert-butyldimethylsilyloxy)-2-(1,2-dimethyl-1H-benzo[d]imidazol-5-yl)ethyl)cyclopropanemethanol

Conditions
ConditionsYield
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
4630-82-4

methyl cyclohexylcarboxylate

diiodomethane
75-11-6

diiodomethane

Methyl 1-iodomethylcyclohexanecarboxylate
374931-25-6

Methyl 1-iodomethylcyclohexanecarboxylate

Conditions
ConditionsYield
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
75-11-6

diiodomethane

4,4-diphenylcyclohex-1-ene
21544-98-9

4,4-diphenylcyclohex-1-ene

(1RS,6RS)-3,3-diphenylbicyclo[4.1.0]heptane

(1RS,6RS)-3,3-diphenylbicyclo[4.1.0]heptane

Conditions
ConditionsYield
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%
diiodomethane
75-11-6

diiodomethane

(RS)-N-(cyclohex-2-en-1-yl)benzamide
4654-36-8

(RS)-N-(cyclohex-2-en-1-yl)benzamide

(1RS,2SR,6SR)-N-(bicyclo[4.1.0]hept-2-yl)benzamide

(1RS,2SR,6SR)-N-(bicyclo[4.1.0]hept-2-yl)benzamide

Conditions
ConditionsYield
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
75-11-6

diiodomethane

methyl ((4-vinyloxy)methyl)benzoate

methyl ((4-vinyloxy)methyl)benzoate

methyl 4-[(cyclopropyloxy)methyl]benzoate
1190044-74-6

methyl 4-[(cyclopropyloxy)methyl]benzoate

Conditions
ConditionsYield
With diethylzinc In dichloromethane at 15 - 30℃; for 3h;100%
diiodomethane
75-11-6

diiodomethane

2,2-difluoro-4-pentenoic acid ethyl ester
110482-96-7

2,2-difluoro-4-pentenoic acid ethyl ester

ethyl 3-cyclopropyl-2,2-difluoropropanoate
1267593-90-7

ethyl 3-cyclopropyl-2,2-difluoropropanoate

Conditions
ConditionsYield
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 Chemical Properties

Diiodomethane's Molecular formula: CH2I2
Molar mass: 267.84 g/mol
Appearance: Light yellow to gold liquid with chloroform-like odour
Density: 3.325 g/cm3
Melting point: 6 °C, 279 K, 43 °F
Boiling point: 181 °C (358 °F)
Solubility in water: 14 g/l at 20 °C
Flash point: 113 °C
Diiodomethane is light yellow to gold  liquid halomethane soluble in ether and alcohol, but insoluble in water.
Diiodomethane has a relatively high refractive index of 1.741. Fresh diiodomethane is a colorless liquid. However, exposure to light causes it to slowly decompose and liberate iodine, which colours it brownish.

DIIODOMETHANE Uses

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 Production

Diiodomethane is commercially available. It may also be prepared by reducing iodoform with sodium arsenite:
        CHI3 + Na3AsO3 + NaOH → CH2I2 + NaI + Na3AsO4

DIIODOMETHANE Toxicity Data With Reference

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.

DIIODOMETHANE Consensus Reports

Reported in EPA TSCA Inventory.

DIIODOMETHANE Safety Profile

Moderately toxic by intraperitoneal and subcutaneous routes. Probably an irritant and narcotic in high concentration. Human systemic effects: acute pulmonary edema, somnolence. Potentially explosive reaction with diethyl zinc + alkenes. Violent reaction with copper-zinc alloys + ether. Forms very shock-sensitive explosive mixtures with potassium, potassium-sodium alloys, and lithium. When heated to decomposition it emits toxic fumes of I. See also IODIDES.
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