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Iodomethane 74-88-4
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Methyl 2-Chloropropionate used in herbicide
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74-88-4 Usage

Chemical Properties

light yellow to light pink liquid

Definition

ChEBI: A member of the class of iodomethanes that is methane in which one of the hydrogens is replaced by iodine.

Reactivity Profile

Halogenated aliphatic compounds, such as Iodomethane, are moderately or very reactive. Reactivity generally decreases with increased degree of substitution of halogen for hydrogen atoms. Low molecular weight haloalkanes are highly flammable and can react with some metals to form dangerous products. Materials in this group are incompatible with strong oxidizing and reducing agents. Also, they are incompatible with many amines, alkylphosphines, nitrides, azo/diazo compounds, alkali metals (sodium), and epoxides.

References

  1. K. R. Redeker; N.-Y. Wang; J. C. Low; A. McMillan; S. C. Tyler & R. J. Cicerone[2000]. "Emissions of Methyl Halides and Methane from Rice Paddies". Science. 290[5493]: 966–969. doi:10.1126/science.290.5493.966.
  2. https://www.sfgate.com/green/article/Methyl-iodide-gains-state-OK-for-use-on-crops-2455128.php
  3. https://www.mercurynews.com/2012/03/20/maker-of-methyl-iodide-scraps-controversial-pesticide/ https://sitem.herts.ac.uk/aeru/ppdb/en/Reports/1233.htm
  4. Keigwin, Richard P. "Iodomethane; Notice of Receipt of Request to Voluntarily Cancel Iodomethane Pesticide Registrations and Amend a Registration." Federal Register[2012].
  5. DPR. 2002a. Product chemistry #1. Volume No. 52875-4, Department of Pesticide Regulation, Registration Branch, Sacramento, California. 
  6. Meister, R.T., ed. 2004. Crop protection handbook. Meister Publishing Company, Willoughby. 
  7. O’Neil, M.J. 2001. The Merck index, 13th ed. Merck & Co., Whitehouse Station, New Jersey. 
  8. http://www.orgsyn.org/demo.aspx?prep=CV2P0399
  9. Sulikowski, Gary A., and M. M. Sulikowski. Iodomethane. e-EROS Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons, Ltd, 2005.
  10. Erk, B.; Boll, R., Trippel, S.; Anielski, D.; Foucar, L.; Rudek, B.; Rudenko, A. Imaging charge transfer in iodomethane upon x-ray photoabsorption. Science 2014, 345[6194], 288-291.
  11. Dong, Y.; Brooks, J. D.; Chen, T. L.; Mullins, D. R.; Cox, D. F. Reactions of methyl groups on a non-reducible metal oxide: The reaction of iodomethane on stoichiometric alpha-Cr 2 O 3[0001]. Surf. Sci. 2015, 641, 148-153.
  12. Bodewitz, H. W. J. J., et al. "The formation of grignard compounds—V: The reaction of iodomethane with magnesium in allyl phenyl ether. A second-order cidnp spectrum." Tetrahedron 34.16(1978]: 2523-2527.
  13. https://sitem.herts.ac.uk/aeru/ppdb/en/Reports/1233.htm
  14. G.D. Clayton and F.E. Clayton, Eds. Patty's Industrial Hygiene and Toxicology. Volume IIB. 3rd revised ed. John Wiley & Sons, New York. 1981.
  15. Ohr, H.D., J.J. Sims, N.M. Grech, J.O. Becker, and M.E. Mcgriffen. 1996. Methyl iodide, an ozone-safe alternative to methyl bromide as a soil fumigant. Plant Dis. 80(7]: 731-735.
  16. Sims, J.J., N.M. Grech, J.O. Becker, M.E. McGiffen, and H.D. Ohr. 1995. Methyl iodide: a potential alternative to methyl bromide. Page 46 in Proc. Of the Second Annual Int. Res. Conf. On Methyl Bromide Alternatives and Emissions Reductions, San Diego. 6-8 Nov. 1995. Methyl Bromide Alternative Outreach, Fresno, CA.
  17. U.S. Environmental Protection Agency. 1993. Protection of stratospheric ozone. RED. Reg. 58(51]:15014-15049.
  18. The United Nations Environmental Programmes. 1995. The Montreal protocol on substances that deplete the ozone layer. 1994 Report of the Methyl Bromide Technical Option Committee. UNEP, Nairobi, Kenya.
  19. http://www.epa.gov/pesticides/factsheets/iodomethane_fs.htm
  20. M. Sittig. Handbook of Toxic and Hazardous Chemicals and Carcinogens. 2nd ed. Noyes Publications, Park Ridge, NJ. 1985.
  21. The Merck Index. An Encyclopedia of Chemicals, Drugs, and Biologicals. 11th ed. Ed. S. Budavari. Merck and Co. Inc., Rahway, NJ. 1989.
  22. https://www.epa.gov/sites/production/files/2016-09/documents/methyl-iodide.pdf

Regulation

Methyl bromide is scheduled for elimination as a soil fumigant and iodomethane has been proposed as an alternative[15-18]. Based on the atmospheric lifetime, global warming potential, and ozone depletion potential, the U.S. Environmental Protection Agency(USEPA) has identified iodomethane as a reduced risk alternative to methyl bromide.
In October, 2007, the USEPA issued a one year time-limited registration of iodomethane. In April 2009, USEPA extended conditional registration of iodomethate without specifying any time limits. The USEPA website provides details of the registration[19]. An application for California registration is currently being evaluated by DPR. Due to its acute toxicity, proposed products containing iodomethane are labeled as restricted use pesticides.

Purification Methods

Methyl iodide deteriorates rapidly with liberation of iodine if exposed to light. It is usually purified by shaking with dilute aqueous Na2S2O3 or NaHSO3 until colourless, then washing with water, dilute aqueous Na2CO3, and more water, drying with CaCl2 and distilling. It is stored in a brown bottle away from sunlight in contact with a small amount of mercury, powdered silver or copper. (Prolonged exposure of mercury to methyl iodide forms methylmercuric iodide.) Methyl iodide can be dried further using CaSO4 or P2O5. An alternative purification is by percolation through a column of silica gel or activated alumina, then distillation. The solution can be degassed by using a repeated freeze-pump-thaw cycle. [Beilstein 1 IV 87.]

Application

Iodomethane is a useful methylating agent that mediates the alkylation of carbon, oxygen, sulfur, nitrogen and phosphorus nucleophiles[9, 10]. For example, phenol reacts with methyl iodide to give anisole. In the Monsanto process, the in situ formed iodomethane reacts with carbon monoxide in the presence of a rhodium complex to give acetyl iodide, which on hydrolysis yields acetic acid[11]. It reacts with magnesium to form the Grignard reagent, methyl-magnesium iodide used in organic synthesis[12]. It also finds applications as an intermediate in the manufacture of pharmaceuticals and in phase-transfer catalysts.
Methyl iodide can also be used as a kind of pesticide used to control insects, plant parasitic nematodes, soil borne pathogens, and weed seeds in vegetables. It can be used in the field growing strawberries, peppers, nut crops, tomatoes, grape vines, ornamentals and turf and nursery growing strawberries, stone fruits, tree nuts, and conifer trees. Its fumigant action is thought to be via the nucleophilic displacement(SN2) reaction in various amino acids and peptides within target organisms. It can also be used as a fire extinguisher[4, 5, 13, 14].

Uses

Methylating agent; in microscopy because of its high refractive index; as imbedding material for examining diatoms; in testing for pyridine. Light sensitive etching agent for electronic circuits; component in fire extinguishers.

Air & Water Reactions

Soluble in water. Sinks and slowly decomposes in water forming poisonous vapor cloud of HI.

Synthesis

Iodomethane can be synthesized by the following several methods[8]:
I. The reaction between methanol with phosphorus triiodide
II. The reaction of dimethyl sulfate with potassium iodide in the presence of calcium carbonate
III. The reaction of methanol with aqueous hydrogen iodide.
IV. The reaction of iodoform with potassium hydroxide and dimethyl sulfate in the presence of ethanol.

Uses

.Iodomethane is an approved pesticide used to control insects, plant parasitic nematodes, soil borne pathogens and weed seeds.

General Description

A colorless liquid that turns brown on exposure to light. Denser than water. Contact may irritate skin, eyes and mucous membranes. Very toxic by ingestion, inhalation and skin absorption.

Physicochemical properties

Iodomethane, an alkyl halide, is a colorless to pale yellow liquid with an acrid odor. It is stable at room temperature in sealed containers, non-corrosive to metals, and incompatible with strong oxidizing and reducing agents. On exposure to light and moisture, the color turns yellow, red or brown due to decomposition and the liberation of free iodine. When heated to decomposition in air at 270 degree, toxic iodine vapors are emitted. Iodomethane is soluble in water, and is miscible with alcohol and ether[5-7].

Overview

Iodomethane is also commonly called methyl iodide. It is a volatile liquid related to methane by replacement of hydrogen. Iodomethane is miscible with common organic solvents. It is colourless, although upon exposure to light, samples develop a purplish tinge. Iodomethane (methyl iodide) is widely used in organic synthesis to deliver a methyl group, via the transformation called methylation.[1]
Iodomethane(also known as methyl iodide), is a kind of alkyl halide. It is naturally emitted by rice plantations in small amounts. Algae are a great natural producer of it with annual output of being greater than 214,000 tons. Therefore, it exists in ocean in large amount. Terrestrial fungi and bacteria also produce certain amount of iodomethane[2, 3]. It is used in organic synthesis as a source of methyl groups.
Methyl iodide had been approved for use as a pesticide by the United States Environmental Protection Agency in 2007 as a pre-plant biocide used to control insects, plant parasitic nematodes, soil borne pathogens, and weed seeds in vegetables such as. It was registered for use as a pre-plant soil treatment for field grown strawberries, peppers, nut crops, tomatoes, grape vines, ornamentals and turf and nursery grown strawberries, stone fruits, tree nuts, and conifer trees. After the discovery phase in a consumer lawsuit, the manufacturer withdrew the fumigant citing its lack of market viability[4].

Health Hazard

Inhalation of vapor causes lung congestion and pulmonary edema. Higher concentrations causes rapid narcosis and death. Contact with liquid irritates eyes and burns skin.

Warning and toxicity

Iodomethane may have certain toxicity when exposure to human and animals[20-22]. In humans, acute[short-term] exposure when inhaling iodomethane may depress the central nervous system(CNS), irritate the lungs and skin, and affect the kidneys[20]. Massive acute inhalation exposure to methyl iodide has led to pulmonary edema. Acute inhalation exposure of humans to methyl iodide has resulted in nausea, vomiting, vertigo, ataxia, slurred speech, drowsiness, skin blistering, and eye irritation[20, 21]. Chronic(long-term) exposure of humans to methyl iodide by inhalation may affect the CNS and cause skin burns in animals and humans. EPA has not classified methyl iodide for potential carcinogenicity[20-22].
InChI:InChI=1/CH3I/c1-2/h1H3

74-88-4 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
Sigma-Aldrich (456756)  Iodomethanesolution  2.0 M in tert-butyl methyl ether, contains copper as stabilizer 74-88-4 456756-100ML 1,199.25CNY Detail
TCI America (I0060)  Iodomethane (stabilized with Copper chip)  >99.5%(GC) 74-88-4 300mL 1,290.00CNY Detail
TCI America (I0060)  Iodomethane (stabilized with Copper chip)  >99.5%(GC) 74-88-4 100mL 490.00CNY Detail
TCI America (I0060)  Iodomethane (stabilized with Copper chip)  >99.5%(GC) 74-88-4 10mL 190.00CNY Detail

74-88-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name iodomethane

1.2 Other means of identification

Product number -
Other names methyl iodide

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Methyl iodide is used as an intermediate in the manufacture of some pharmaceuticals and pesticides. It is also used in methylation processes and in the field of microscopy. Proposed uses of methyl iodide are as a fire extinguisher and as an insecticidal fumigant.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:74-88-4 SDS

74-88-4Synthetic route

methyl n-nonyl ether
7289-51-2

methyl n-nonyl ether

A

methyl iodide
74-88-4

methyl iodide

B

nonyl alcohol
143-08-8

nonyl alcohol

Conditions
ConditionsYield
With Methyltrichlorosilane; sodium iodide In acetonitrile at 25℃; for 9h;A n/a
B 100%
methyl p-toluene sulfonate
80-48-8

methyl p-toluene sulfonate

methylphosphinobis(triethylammonium iodide)

methylphosphinobis(triethylammonium iodide)

A

C13H33N2P(2+)*2C7H7O3S(1-)

C13H33N2P(2+)*2C7H7O3S(1-)

B

methyl iodide
74-88-4

methyl iodide

Conditions
ConditionsYield
A 100%
B n/a
trans-(CH3)2Co(11-hydroxy-2,3,9,10-tetramethyl-1,4,8,11-tetraazaundeca-1,3,8,10-tetraen-1-olate)

trans-(CH3)2Co(11-hydroxy-2,3,9,10-tetramethyl-1,4,8,11-tetraazaundeca-1,3,8,10-tetraen-1-olate)

iodine
7553-56-2

iodine

A

methane
34557-54-5

methane

B

ethane
74-84-0

ethane

C

methyl iodide
74-88-4

methyl iodide

Conditions
ConditionsYield
In tetrachloromethane Irradiation (UV/VIS); Irradiation at 509 nm in CCl4; Estimation of the quantum yield of the photochemical reaction. Yield of the products estimated by g.l.c.;A 0.02%
B <1
C 100%
trans-(CH3)2Co(11-hydroxy-2,3,9,10-tetramethyl-1,4,8,11-tetraazaundeca-1,3,8,10-tetraen-1-olate)

trans-(CH3)2Co(11-hydroxy-2,3,9,10-tetramethyl-1,4,8,11-tetraazaundeca-1,3,8,10-tetraen-1-olate)

iodine
7553-56-2

iodine

trans-methyl iodo cobalt (III) 3,9-dimethyl-4,8-diazaundecane-3,8-diene-2,10-dione dioximate

trans-methyl iodo cobalt (III) 3,9-dimethyl-4,8-diazaundecane-3,8-diene-2,10-dione dioximate

B

methyl iodide
74-88-4

methyl iodide

Conditions
ConditionsYield
In tetrachloromethane Kinetics; byproducts: C2H6, CH4; Irradiation (UV/VIS); Kinetics of the reaction of Co(CH3)2(H3CCNOHC(CH3)NC3H6NC(CH3)CNOCH3) with I2 under irradiation with light at 517 nm is investigated.; MeI and Co(CH3)I(H3CCNOHC(CH3)NC3H6NC(CH3)CNOCH3) are the main products, C2H6 and CH4 are byproducts.;A n/a
B 100%
CoMe(pyridine)(dimethylglyoxime(-1H))2
23642-14-0

CoMe(pyridine)(dimethylglyoxime(-1H))2

iodine
7553-56-2

iodine

A

iodobisdimethylglyoximepyridine cobalt(III)

iodobisdimethylglyoximepyridine cobalt(III)

B

methyl iodide
74-88-4

methyl iodide

Conditions
ConditionsYield
In tetrachloromethane Kinetics; Irradiation (UV/VIS); Kinetics of the reaction of Co(CH3)(H3CCNOHONCCH3)2(C5H5N) with I2 under irradiation with light at 517 nm is investigated.; MeI and CoI(H3CCNOHONCCH3)2(C5H5N) are the products.;A n/a
B 100%
CoMe(pyridine)(dimethylglyoxime(-1H))2
23642-14-0

CoMe(pyridine)(dimethylglyoxime(-1H))2

methyl iodide
74-88-4

methyl iodide

Conditions
ConditionsYield
With iodine In acetonitrile Kinetics; byproducts: {Co(bis(dimethylglyoximato))py(I)}; one-electron oxidn. of Co complex by I2 at 298 K; monitored by (1)H-NMR and UV spect. (361 nm);100%
C10H8I3InO2

C10H8I3InO2

A

C9H5I2InO2

C9H5I2InO2

B

methyl iodide
74-88-4

methyl iodide

Conditions
ConditionsYield
In toluene at 50℃; for 10h;A 100%
B n/a
methanol
67-56-1

methanol

methyl iodide
74-88-4

methyl iodide

Conditions
ConditionsYield
With iron; sodium iodide In water at 70℃; Reagent/catalyst; Temperature; Inert atmosphere;99.6%
With hydrogen iodide at 120℃; for 2h;76%
With hydrogen iodide
cis-{(CH3)2Co(2,2'-bipyridine)}(ClO4)

cis-{(CH3)2Co(2,2'-bipyridine)}(ClO4)

iodine
7553-56-2

iodine

cis-methyl iodo bis(2,2'-bipyridyl) cobalt(II) perchlorate

cis-methyl iodo bis(2,2'-bipyridyl) cobalt(II) perchlorate

B

methyl iodide
74-88-4

methyl iodide

Conditions
ConditionsYield
In tetrachloromethane Kinetics; byproducts: C2H6, CH4; Irradiation (UV/VIS); Kinetics of the reaction of Co(CH3)2(bipy)2ClO4 with I2 under irradiation with light at 517 nm is investigated.; MeI and Co(CH3)I(bipy)2ClO4 are the main products, C2H6 and CH4 are byproducts.;A n/a
B 99%
cis-{(CH3)2Co(2,2'-bipyridine)}(ClO4)

cis-{(CH3)2Co(2,2'-bipyridine)}(ClO4)

A

methane
34557-54-5

methane

B

ethane
74-84-0

ethane

C

methyl iodide
74-88-4

methyl iodide

Conditions
ConditionsYield
With iodine In acetonitrile Kinetics; byproducts: I3(1-), (CH3Co(2,2'-bipyridine)2I)(1+); one-electron oxidn. of cis-Co complex by I2 at 298 K; monitored by (1)H-NMR and UV spect. (361 nm);A <1
B 0.6%
C 99%
cis-{Me2Co(2,2'-bipyridine)2}(1+)

cis-{Me2Co(2,2'-bipyridine)2}(1+)

iodine
7553-56-2

iodine

A

methane
34557-54-5

methane

B

ethane
74-84-0

ethane

C

methyl iodide
74-88-4

methyl iodide

Conditions
ConditionsYield
In tetrachloromethane Irradiation (UV/VIS); Irradiation at 509 nm in CCl4; Estimation of the quantum yield of the photochemical reaction. Yield of the products are estimated by g.l.c.;A <1
B 0.9%
C 99%
trans-(CH3)2Co(11-hydroxy-2,3,9,10-tetramethyl-1,4,8,11-tetraazaundeca-1,3,8,10-tetraen-1-olate)

trans-(CH3)2Co(11-hydroxy-2,3,9,10-tetramethyl-1,4,8,11-tetraazaundeca-1,3,8,10-tetraen-1-olate)

A

methane
34557-54-5

methane

B

ethane
74-84-0

ethane

C

methyl iodide
74-88-4

methyl iodide

Conditions
ConditionsYield
With iodine In acetonitrile Kinetics; byproducts: I3(1-); one-electron oxidn. of trans-Co complex by I2 at 298 K; monitored by (1)H-NMR and UV spect. (361 nm);A 0.34%
B 0.06%
C 99%
4-methoxy-3-(3,4,5-trimethoxyphenyl)ethynylcoumarin
1279109-19-1

4-methoxy-3-(3,4,5-trimethoxyphenyl)ethynylcoumarin

A

3-iodo-2-(3,4,5-trimethoxy)phenyl-4H-furo[2,3-b]benzopyran-4-one
1279109-09-9

3-iodo-2-(3,4,5-trimethoxy)phenyl-4H-furo[2,3-b]benzopyran-4-one

B

methyl iodide
74-88-4

methyl iodide

Conditions
ConditionsYield
With iodine In 1,2-dichloro-ethane for 0.5h; Reflux;A 98%
B n/a
(5S,8R,9S,10S,13R,14S,17R)-17-((1R,4R)-4-Ethyl-1,5-dimethyl-hexyl)-3-methoxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthrene
78371-06-9, 82863-11-4, 103881-30-7, 139894-64-7

(5S,8R,9S,10S,13R,14S,17R)-17-((1R,4R)-4-Ethyl-1,5-dimethyl-hexyl)-3-methoxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthrene

A

sitostanol
204638-28-8

sitostanol

B

methyl iodide
74-88-4

methyl iodide

Conditions
ConditionsYield
With Methyltrichlorosilane; sodium iodide In acetonitrile at 25℃; for 16h;A 97%
B n/a
(CH3)3Sn(CH2)4C6H5
34232-10-5

(CH3)3Sn(CH2)4C6H5

iodine
7553-56-2

iodine

methyl iodide
74-88-4

methyl iodide

Conditions
ConditionsYield
In acetonitrile96%
In acetonitrile96%
4-methoxy-3-(4-methoxy)phenylethynylcoumarin
1192179-68-2

4-methoxy-3-(4-methoxy)phenylethynylcoumarin

A

3-iodo-2-(4-methoxy)phenyl-4H-furo[2,3-b]benzopyran-4-one
1279109-08-8

3-iodo-2-(4-methoxy)phenyl-4H-furo[2,3-b]benzopyran-4-one

B

methyl iodide
74-88-4

methyl iodide

Conditions
ConditionsYield
With iodine In 1,2-dichloro-ethane for 0.5h; Reflux;A 92%
B n/a
tetraethylammonium iodide
68-05-3

tetraethylammonium iodide

A

Dimethyl ether
115-10-6

Dimethyl ether

B

tetraethylammonium pyrosulfate

tetraethylammonium pyrosulfate

C

methyl iodide
74-88-4

methyl iodide

Conditions
ConditionsYield
With dimethyl sulfate at 130℃; for 0.5h; Product distribution;A n/a
B 90%
C n/a
With dimethyl sulfate at 130℃; for 0.5h;A n/a
B 90%
C n/a
4-methoxy-6-methyl-3-phenylethynylcoumarin
1279109-21-5

4-methoxy-6-methyl-3-phenylethynylcoumarin

A

3-iodo-6-methyl-2-phenyl-4H-furo[2,3-b]benzopyran-4-one
1279109-11-3

3-iodo-6-methyl-2-phenyl-4H-furo[2,3-b]benzopyran-4-one

B

methyl iodide
74-88-4

methyl iodide

Conditions
ConditionsYield
With iodine In 1,2-dichloro-ethane for 6h; Reflux;A 89%
B n/a
4-methoxy-3-(4-fluorophenyl)ethynylcoumarin
1279109-18-0

4-methoxy-3-(4-fluorophenyl)ethynylcoumarin

A

3-iodo-2-(4-fluoro)phenyl-4H-furo[2,3-b]benzopyran-4-one
1279109-06-6

3-iodo-2-(4-fluoro)phenyl-4H-furo[2,3-b]benzopyran-4-one

B

methyl iodide
74-88-4

methyl iodide

Conditions
ConditionsYield
With iodine In 1,2-dichloro-ethane for 6h; Reflux;A 89%
B n/a
iodobenzene
591-50-4

iodobenzene

metyhyl chlorodifluoroacetate
1514-87-0

metyhyl chlorodifluoroacetate

A

α,α,α-trifluorotoluene
98-08-8

α,α,α-trifluorotoluene

B

methyl iodide
74-88-4

methyl iodide

Conditions
ConditionsYield
With potassium fluoride; copper(l) iodide In N,N-dimethyl-formamide at 100 - 120℃; for 8h; Product distribution; Mechanism; other solvent; other organic halides;A 88%
B n/a
6-chloro-4-methoxy-3-phenylethynylcoumarin
1279109-20-4

6-chloro-4-methoxy-3-phenylethynylcoumarin

A

6-chloro-3-iodo-2-phenyl-4H-furo[2,3-b]benzopyran-4-one
1279109-10-2

6-chloro-3-iodo-2-phenyl-4H-furo[2,3-b]benzopyran-4-one

B

methyl iodide
74-88-4

methyl iodide

Conditions
ConditionsYield
With iodine In 1,2-dichloro-ethane for 72h; Reflux;A 88%
B n/a
4-methoxyoctane
77067-56-2

4-methoxyoctane

A

octan-4-ol
589-62-8

octan-4-ol

B

methyl iodide
74-88-4

methyl iodide

Conditions
ConditionsYield
With Methyltrichlorosilane; sodium iodide In acetonitrile at 25℃; for 10h;A 85%
B n/a
4-methoxy-3-phenylethynylcoumarin
1073128-26-3

4-methoxy-3-phenylethynylcoumarin

A

3-iodo-2-phenyl-4H-furo[2,3-b][1]benzopyran-4-one
1192179-80-8

3-iodo-2-phenyl-4H-furo[2,3-b][1]benzopyran-4-one

B

methyl iodide
74-88-4

methyl iodide

Conditions
ConditionsYield
With iodine In 1,2-dichloro-ethane for 5h; Reflux;A 85%
B n/a
octamethylcyclotetrasiloxane
556-67-2

octamethylcyclotetrasiloxane

A

trimethylsilyl iodide
16029-98-4

trimethylsilyl iodide

B

Hexamethyldisiloxane
107-46-0

Hexamethyldisiloxane

C

methyl iodide
74-88-4

methyl iodide

Conditions
ConditionsYield
With aluminium(III) iodide at 140 - 170℃; for 5h;A n/a
B 83.5%
C n/a
2,3-dimethylnaphtho<1,2-d>thiazolium methyl sulfate
64415-17-4

2,3-dimethylnaphtho<1,2-d>thiazolium methyl sulfate

A

ethene
74-85-1

ethene

B

Dimethyl ether
115-10-6

Dimethyl ether

C

2,3-dimethylnaphtho<1,2-d>thiazolium bisulfate

2,3-dimethylnaphtho<1,2-d>thiazolium bisulfate

D

methyl iodide
74-88-4

methyl iodide

Conditions
ConditionsYield
With dimethyl sulfate at 130℃; for 0.666667h;A n/a
B n/a
C 82%
D n/a
iodine
7553-56-2

iodine

n-butyltrimethyltin
1527-99-7

n-butyltrimethyltin

methyl iodide
74-88-4

methyl iodide

Conditions
ConditionsYield
In acetonitrile at room temp.;;82%
In acetonitrile at room temp.;;82%
2-methoxycyclohexane
931-56-6

2-methoxycyclohexane

A

cyclohexanol
108-93-0

cyclohexanol

B

methyl iodide
74-88-4

methyl iodide

Conditions
ConditionsYield
With Methyltrichlorosilane; sodium iodide In acetonitrile at 25℃; for 7h;A 81%
B n/a
Methyl methanesulfonate
66-27-3

Methyl methanesulfonate

trimethylsilyl iodide
16029-98-4

trimethylsilyl iodide

A

trimethylsilyl methanesulfonate
10090-05-8

trimethylsilyl methanesulfonate

B

methyl iodide
74-88-4

methyl iodide

Conditions
ConditionsYield
for 1h; Heating;A 79%
B 6.8 g
picoline
108-89-4

picoline

methyl iodide
74-88-4

methyl iodide

N-methyl-4-methylpyridinium iodide
2301-80-6

N-methyl-4-methylpyridinium iodide

Conditions
ConditionsYield
In diethyl ether at 20℃; for 120h; Methylation;100%
In acetone for 2h; Reflux;100%
In ethanol at 78℃; for 0.333333h;96%
1-methyl-1H-imidazole
616-47-7

1-methyl-1H-imidazole

methyl iodide
74-88-4

methyl iodide

1,3-dimethylimidazolim iodide
4333-62-4

1,3-dimethylimidazolim iodide

Conditions
ConditionsYield
In dichloromethane for 1h;100%
In dichloromethane at 0℃; for 3h;99%
at 60℃;98%
4-Methylthiazole
693-95-8

4-Methylthiazole

methyl iodide
74-88-4

methyl iodide

3,4-dimethylthiazolinium iodide
24300-70-7

3,4-dimethylthiazolinium iodide

Conditions
ConditionsYield
In tetrahydrofuran at 90℃; for 48h;100%
In methanol; ethyl acetate at 20℃; for 36h;61%
3,5-Lutidine
591-22-0

3,5-Lutidine

methyl iodide
74-88-4

methyl iodide

N-methyl-3,5-dimethylpyridinium iodide
22739-24-8

N-methyl-3,5-dimethylpyridinium iodide

Conditions
ConditionsYield
In dimethylsulfoxide-d6 at 20℃; for 0.75h; Schlenk technique; Inert atmosphere;100%
In acetone at 25℃; Rate constant; pKa value;
In acetonitrile at 25℃; Rate constant;
2,6-dimethylpyridine
108-48-5

2,6-dimethylpyridine

methyl iodide
74-88-4

methyl iodide

1,2,6-trimethylpyridinium iodide
2525-19-1

1,2,6-trimethylpyridinium iodide

Conditions
ConditionsYield
In dimethylsulfoxide-d6 at 20℃; for 120h; Schlenk technique; Inert atmosphere;100%
In sulfolane at 50℃; for 4h;95%
With sulfolane at 50℃; for 4h;95.3%
3-Bromopyridine
626-55-1

3-Bromopyridine

methyl iodide
74-88-4

methyl iodide

3-bromo-1-methylpyridinium iodide
32222-42-7

3-bromo-1-methylpyridinium iodide

Conditions
ConditionsYield
With ethanol at 92℃; for 16h; Inert atmosphere; Reflux;100%
In acetone at 20℃; for 144h;98%
In acetonitrile for 24h; Reflux;97%
3,4,5,6-tetrahydropyrimidine-2-thione
2055-46-1

3,4,5,6-tetrahydropyrimidine-2-thione

methyl iodide
74-88-4

methyl iodide

2-methylthio-1,4,5,6-tetrahydropyrimidine hydroiodide
5445-73-8

2-methylthio-1,4,5,6-tetrahydropyrimidine hydroiodide

Conditions
ConditionsYield
In methanol for 5h; Heating;100%
In ethanol at 20℃; for 6.08333h;100%
In methanol for 5h; Heating / reflux;100%
p-phenylpyridine
939-23-1

p-phenylpyridine

methyl iodide
74-88-4

methyl iodide

4-phenyl-N-methylpyridinium iodide
36913-39-0

4-phenyl-N-methylpyridinium iodide

Conditions
ConditionsYield
In acetonitrile at 80℃; for 24h; Sealed tube; Inert atmosphere;100%
In acetonitrile at 80℃; for 16h;96%
In acetone81%
at 20℃;
In acetonitrile at 20℃; for 12h;
C6H4NCH2CHCCH2
491-35-0

C6H4NCH2CHCCH2

methyl iodide
74-88-4

methyl iodide

1,4-dimethylquinolinium iodide
16859-86-2

1,4-dimethylquinolinium iodide

Conditions
ConditionsYield
In 1,4-dioxane at 101℃; for 1.5h; Inert atmosphere;100%
In benzene for 1h; Reflux;99%
In dichloromethane at 20℃; for 24h;98%
2-thiouracil
141-90-2

2-thiouracil

methyl iodide
74-88-4

methyl iodide

2-Methylthiouracil
5751-20-2

2-Methylthiouracil

Conditions
ConditionsYield
Stage #1: 2-thiouracil; methyl iodide With sodium hydroxide In water at 20℃; for 16h;
Stage #2: With acetic acid In water
100%
Stage #1: 2-thiouracil With sodium hydroxide In water at 60 - 70℃;
Stage #2: methyl iodide In ethanol; water at 30 - 60℃; for 0.333333h;
Stage #3: With acetic acid In ethanol; water at 20℃;
100%
With sodium hydroxide at 20℃; for 18h;99%
5-hydroxyethyl-4-methylthiazole
137-00-8

5-hydroxyethyl-4-methylthiazole

methyl iodide
74-88-4

methyl iodide

3,4-dimethyl-5-(2-hydroxyethyl)thiazolium iodide
16311-69-6

3,4-dimethyl-5-(2-hydroxyethyl)thiazolium iodide

Conditions
ConditionsYield
at 60℃; for 3h; Autoclave;100%
for 2h; Reflux;96.3%
at 50℃; for 2h;96.2%
2-mercapto-5-nitropyridine
2127-09-5

2-mercapto-5-nitropyridine

methyl iodide
74-88-4

methyl iodide

3-nitro-6-(methylthio)pyridine
20885-21-6

3-nitro-6-(methylthio)pyridine

Conditions
ConditionsYield
With monosodium carbonate In ethanol; water at 20℃; for 1h;100%
With methanol
isonicotinic acid ethylester
1570-45-2

isonicotinic acid ethylester

methyl iodide
74-88-4

methyl iodide

1-methyl-4-ethoxycarbonylpyridinium iodide
10129-59-6

1-methyl-4-ethoxycarbonylpyridinium iodide

Conditions
ConditionsYield
In ethanol at 60℃;100%
Methylation;95%
In acetone for 20h;90%
6-hydroxy-4-oxo-4H-1-benzopyran
38445-24-8

6-hydroxy-4-oxo-4H-1-benzopyran

methyl iodide
74-88-4

methyl iodide

6-methoxy-chromen-4-one
59887-88-6

6-methoxy-chromen-4-one

Conditions
ConditionsYield
With potassium carbonate In acetone at 100℃; for 0.0833333h; Reflux;100%
With potassium carbonate; acetone
N-phenylnicotinamide
1752-96-1

N-phenylnicotinamide

methyl iodide
74-88-4

methyl iodide

1-mehtyl-3-phenylaminocarbonylpyridinium iodide
81795-18-8

1-mehtyl-3-phenylaminocarbonylpyridinium iodide

Conditions
ConditionsYield
In ethanol; acetone at 40℃;100%
In methanol at 60℃; for 6h;91%
for 24h; Ambient temperature;81%
at 100℃;
4,5-diphenyl-1H-imidazole
668-94-0

4,5-diphenyl-1H-imidazole

methyl iodide
74-88-4

methyl iodide

4,5-diphenyl-1-methyl-1H-imidazole
50609-88-6

4,5-diphenyl-1-methyl-1H-imidazole

Conditions
ConditionsYield
Stage #1: 4,5-diphenyl-1H-imidazole With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 1h; Inert atmosphere; Schlenk technique; Glovebox;
Stage #2: methyl iodide In tetrahydrofuran; mineral oil at 35℃; Inert atmosphere; Schlenk technique; Glovebox;
100%
Stage #1: 4,5-diphenyl-1H-imidazole With potassium tert-butylate In tetrahydrofuran at 0℃; for 1h; Inert atmosphere;
Stage #2: methyl iodide In tetrahydrofuran at 0 - 20℃; Inert atmosphere;
89%
Stage #1: 4,5-diphenyl-1H-imidazole With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; Inert atmosphere; Schlenk technique; Glovebox;
Stage #2: methyl iodide In tetrahydrofuran; mineral oil at 20℃; Inert atmosphere; Schlenk technique; Glovebox;
81%
benzbromarone
3562-84-3

benzbromarone

methyl iodide
74-88-4

methyl iodide

(3,5-dibromo-4-methoxy-phenyl)-(2-ethyl-benzofuran-3-yl)-methanone
51073-13-3

(3,5-dibromo-4-methoxy-phenyl)-(2-ethyl-benzofuran-3-yl)-methanone

Conditions
ConditionsYield
With potassium carbonate In acetone for 16h; Heating / reflux;100%
Stage #1: benzbromarone With potassium carbonate In tetrahydrofuran for 0.166667h;
Stage #2: methyl iodide In tetrahydrofuran at 40℃; for 16h;
22%
With potassium hydroxide
((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol
4099-85-8

((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol

methyl iodide
74-88-4

methyl iodide

(3AR,4R,6R,6AR)-4-Methoxy-6-(methoxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole
33985-44-3

(3AR,4R,6R,6AR)-4-Methoxy-6-(methoxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole

Conditions
ConditionsYield
With silver(l) oxide In N,N-dimethyl-formamide for 4h; Ambient temperature;100%
Stage #1: ((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃;
Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃; Further stages.;
97%
With sodium hydride In N,N-dimethyl-formamide Ambient temperature;90%
indole-2,3-dione
91-56-5

indole-2,3-dione

methyl iodide
74-88-4

methyl iodide

1-methyl-1H-indole-2,3-dione
2058-74-4

1-methyl-1H-indole-2,3-dione

Conditions
ConditionsYield
Stage #1: indole-2,3-dione With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.0833333h;
Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 25℃; for 12h;
100%
With potassium carbonate99%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 12h;98%
phenylacetonitrile
140-29-4

phenylacetonitrile

methyl iodide
74-88-4

methyl iodide

2-methyl-2-phenylpropionitrile
1195-98-8

2-methyl-2-phenylpropionitrile

Conditions
ConditionsYield
With sodium hydroxide; dimethyl sulfoxide In water100%
Stage #1: phenylacetonitrile With sodium hydride In tetrahydrofuran at 0 - 20℃; for 1.5h; Inert atmosphere;
Stage #2: methyl iodide In tetrahydrofuran at 0℃; for 16h; Inert atmosphere;
100%
With potassium tert-butylate In tetrahydrofuran99.4%
ethyl 3-oxo-3-phenylpropionate
94-02-0

ethyl 3-oxo-3-phenylpropionate

methyl iodide
74-88-4

methyl iodide

ethyl 2-benzoylpropionate
10488-87-6

ethyl 2-benzoylpropionate

Conditions
ConditionsYield
Stage #1: ethyl 3-oxo-3-phenylpropionate With sodium hydride In tetrahydrofuran; mineral oil at 20℃; Inert atmosphere;
Stage #2: methyl iodide In tetrahydrofuran; mineral oil at 20℃; for 20h; Inert atmosphere;
100%
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 3h; Inert atmosphere;99%
With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 20h;99%
9H-carbazole
86-74-8

9H-carbazole

methyl iodide
74-88-4

methyl iodide

N-methylcarbazole
1484-12-4

N-methylcarbazole

Conditions
ConditionsYield
Stage #1: 9H-carbazole With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.5h;
Stage #2: methyl iodide In N,N-dimethyl-formamide
100%
With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃;96%
With sodium hydroxide In N,N-dimethyl-formamide at 2℃; for 4h;95%
1-(methyl)-thiourea
598-52-7

1-(methyl)-thiourea

methyl iodide
74-88-4

methyl iodide

N,S-dimethylisothiourea hydroiodide
41306-45-0

N,S-dimethylisothiourea hydroiodide

Conditions
ConditionsYield
In methanol for 1h;100%
In ethanol for 12h;100%
In acetone for 18h; Ambient temperature;43%
With ethanol Geschwindigkeit dieser Reaktion in absol.Alkohol,Isobutylalkohol und Aceton bei 25grad;
In acetonitrile Methylation; Heating;
1,1,3-trimethylthiourea
2489-77-2

1,1,3-trimethylthiourea

methyl iodide
74-88-4

methyl iodide

N,N’,N”-trimethyl-S-methylisothiuronium iodide
56043-32-4

N,N’,N”-trimethyl-S-methylisothiuronium iodide

Conditions
ConditionsYield
In ethanol at 20℃; for 12h;100%
In ethanol for 12h;100%
With ethanol Geschwindigkeit dieser Reaktion bei 25grad;
triethylamine
121-44-8

triethylamine

methyl iodide
74-88-4

methyl iodide

triethylmethylammonium iodide
994-29-6

triethylmethylammonium iodide

Conditions
ConditionsYield
With Hexamethyldisiloxane at 20℃; for 24h; Solvent; Green chemistry;100%
In butanone at 20℃; Menshutkin reaction;85%
In methanol; acetonitrile at 30℃; Thermodynamic data; Rate constant; ΔH(excit.), ΔS(excit.); ratio of solvents; transfer enthalpies of activated complex;
thiourea
17356-08-0

thiourea

methyl iodide
74-88-4

methyl iodide

S-methylthiouronium iodide
4338-95-8

S-methylthiouronium iodide

Conditions
ConditionsYield
In ethanol at 20℃; for 12h;100%
In ethanol for 12h;100%
In methanol at 65℃; for 1.5h;99%
phenylacetylene
536-74-3

phenylacetylene

methyl iodide
74-88-4

methyl iodide

1-Phenylprop-1-yne
673-32-5

1-Phenylprop-1-yne

Conditions
ConditionsYield
Stage #1: phenylacetylene With n-butyllithium In tetrahydrofuran; hexane Inert atmosphere;
Stage #2: methyl iodide In tetrahydrofuran; hexane at -20 - 20℃;
100%
Stage #1: phenylacetylene With lithium diisopropyl amide In tetrahydrofuran at -78℃;
Stage #2: methyl iodide
89%
With potassium hydroxide In dimethyl sulfoxide at 18℃; for 1.5h;80%
triphenylphosphine
603-35-0

triphenylphosphine

methyl iodide
74-88-4

methyl iodide

methyl-triphenylphosphonium iodide
2065-66-9

methyl-triphenylphosphonium iodide

Conditions
ConditionsYield
for 0.00833333h; Heating; microwave irradiation;100%
In toluene at 0℃; for 4h; Reflux;100%
In dichloromethane at 20℃; Inert atmosphere;100%
2,4-Xylenol
105-67-9

2,4-Xylenol

methyl iodide
74-88-4

methyl iodide

2,4-dimethylanisole
6738-23-4

2,4-dimethylanisole

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 5h; Methylation;100%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; Cooling with ice;85%
With potassium carbonate In water; N,N-dimethyl-formamide at 20℃; Cooling with ice;85%
5-hydroxyisoquinoline
2439-04-5

5-hydroxyisoquinoline

methyl iodide
74-88-4

methyl iodide

5-hydroxy-2-methylisoquinolinium iodide
20189-73-5

5-hydroxy-2-methylisoquinolinium iodide

Conditions
ConditionsYield
In methanol for 192h;100%
With ethanol

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