66688-32-2

Usage

Uses

Used in Pharmaceutical Industry:
Butane, 1,4-diiodo-2-methylis used as a reagent in the synthesis of various pharmaceutical compounds. Its unique structure and reactivity make it a valuable intermediate in the production of drugs with specific therapeutic properties.
Used in Agrochemical Industry:
In the agrochemical industry, Butane, 1,4-diiodo-2-methylis utilized as a reagent for the synthesis of agrochemicals, such as pesticides and herbicides. Its ability to undergo various chemical reactions contributes to the development of effective and targeted agrochemical products.
Used in Chemical Industry:
Butane, 1,4-diiodo-2-methylis employed in the chemical industry for a wide range of applications, including the synthesis of various organic compounds and materials. Its versatility and reactivity make it a valuable component in the development of new chemical products and processes.
It is important to handle Butane, 1,4-diiodo-2-methylwith caution due to its potential health and environmental hazards. Proper safety measures should be taken during its production, storage, and use to minimize risks.

Synthetic route

1,4-dibromo-2-methyl-butane (54462-66-7) → 1,4-diiodo-2-methylbutane (66688-32-2)

Conditions	Yield
With sodium iodide In acetone Ambient temperature;	99%

3-methyltetrahydrofuran (13423-15-9) → 1,4-diiodo-2-methylbutane (66688-32-2)

Conditions	Yield
With O-phenyl phosphorodichloridate; sodium iodide for 40h; Heating;	85%

Diethyl difluoromethylphosphonate (1478-53-1) + 1,4-diiodo-2-methylbutane (66688-32-2) → diethyl 1,1-difluoro-5-iodo-4-methylpentylphosphonate (876938-99-7) + [6-(diethoxy-phosphoryl)-1,1,6,6-tetrafluoro-4-methyl-hexyl]-phosphonic acid diethyl ester

Conditions	Yield
Stage #1: Diethyl difluoromethylphosphonate With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1.16667h; Stage #2: 2-methyl-1,4-diiodobutane In tetrahydrofuran at -78℃; for 4h;	A 30% B 7%

tert-butyl (trimethylsilyl)acetate (41108-81-0) + 1,4-diiodo-2-methylbutane (66688-32-2) → tert-butyl 1-(trimethylsilyl)-3-methylcyclopentanecarboxylate (119880-33-0)

Conditions	Yield
With lithium diisopropyl amide 1.) THF, -78 deg C, 15 min, 2.) a) -30 deg C, 3 h, b) 20 deg C, overnight; Yield given. Multistep reaction;

1,4-diiodo-2-methylbutane (66688-32-2) → 3-methyltetrahydrothiophene (4740-00-5)

Conditions	Yield
With sodium sulfide In ethanol; water for 6h; Heating; Yield given;

1,4-diiodo-2-methylbutane (66688-32-2) → [5-(6-chloro-purin-9-yl)-1,1-difluoro-4-methyl-pentyl]-phosphonic acid

Conditions	Yield
Multi-step reaction with 3 steps 1.1: lithium diisopropylamide / tetrahydrofuran / 1.17 h / -78 °C 1.2: 30 percent / tetrahydrofuran / 4 h / -78 °C 2.1: 52 percent / potassium carbonate / dimethylformamide / 20 °C 3.1: bromotrimethylsilane / CH2Cl2 / 44 h / 20 °C View Scheme

1,4-diiodo-2-methylbutane (66688-32-2) → [1,1-difluoro-4-methyl-5-(6-oxo-1,6-dihydro-purin-9-yl)-pentyl]-phosphonic acid

Conditions	Yield
Multi-step reaction with 4 steps 1.1: lithium diisopropylamide / tetrahydrofuran / 1.17 h / -78 °C 1.2: 30 percent / tetrahydrofuran / 4 h / -78 °C 2.1: 52 percent / potassium carbonate / dimethylformamide / 20 °C 3.1: bromotrimethylsilane / CH2Cl2 / 44 h / 20 °C 4.1: hydrochloric acid / Heating View Scheme

1,4-diiodo-2-methylbutane (66688-32-2) → diethyl 5-(6-chloro-9H-purin-9-yl)-1,1-difluoro-4-methylpentylphosphonate (876939-01-4)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: lithium diisopropylamide / tetrahydrofuran / 1.17 h / -78 °C 1.2: 30 percent / tetrahydrofuran / 4 h / -78 °C 2.1: 52 percent / potassium carbonate / dimethylformamide / 20 °C View Scheme

1,4-diiodo-2-methylbutane (66688-32-2) → [5-(2-amino-6-chloro-purin-9-yl)-1,1-difluoro-4-methyl-pentyl]-phosphonic acid

Conditions	Yield
Multi-step reaction with 3 steps 1.1: lithium diisopropylamide / tetrahydrofuran / 1.17 h / -78 °C 1.2: 30 percent / tetrahydrofuran / 4 h / -78 °C 2.1: 37 percent / potassium carbonate / dimethylformamide / 23 h / 20 °C 3.1: bromotrimethylsilane / CH2Cl2 / 44 h / 20 °C View Scheme

1,4-diiodo-2-methylbutane (66688-32-2) → 9-(2'-methyl-5',5'-difluoro-5'-phosphonopentyl)guanine

Conditions	Yield
Multi-step reaction with 4 steps 1.1: lithium diisopropylamide / tetrahydrofuran / 1.17 h / -78 °C 1.2: 30 percent / tetrahydrofuran / 4 h / -78 °C 2.1: 37 percent / potassium carbonate / dimethylformamide / 23 h / 20 °C 3.1: bromotrimethylsilane / CH2Cl2 / 44 h / 20 °C 4.1: 388 mg / hydrochloric acid / Heating View Scheme

1,4-diiodo-2-methylbutane (66688-32-2) → diethyl 5-(2-amino-6-chloro-9H-purin-9-yl)-1,1-difluoro-4-methylpentylphosphonate (876939-00-3)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: lithium diisopropylamide / tetrahydrofuran / 1.17 h / -78 °C 1.2: 30 percent / tetrahydrofuran / 4 h / -78 °C 2.1: 37 percent / potassium carbonate / dimethylformamide / 23 h / 20 °C View Scheme

1,4-diiodo-2-methylbutane (66688-32-2) → 3-methyl-thiolane-1-oxide (93111-02-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: Na2S*9H2O / ethanol; H2O / 6 h / Heating 2: 51 percent / NaIO4 / H2O / 0 °C View Scheme

1,4-diiodo-2-methylbutane (66688-32-2) → Trimethyl-((1R,3R)-3-methyl-cyclopentyl)-silane (17939-99-0, 119880-40-9, 119880-41-0)

Conditions	Yield
Multi-step reaction with 6 steps 1: 1.) LDA / 1.) THF, -78 deg C, 15 min, 2.) a) -30 deg C, 3 h, b) 20 deg C, overnight 2: 1.29 g / Dibal-H / CH2Cl2; hexane / 4 h / -10 - 0 °C 3: 83 percent / Ag2CO3, Celite / benzene / 7 h / Heating 4: 1.89 g / diethyl ether / 0.33 h / -78 °C 5: CrO3, pyridine / CH2Cl2 / 0.67 h 6: NaNH2 / benzene / 2 h / Ambient temperature View Scheme

1,4-diiodo-2-methylbutane (66688-32-2) → Trimethyl-((1R,3S)-3-methyl-cyclopentyl)-silane (17939-99-0, 119880-40-9, 119880-41-0)

Conditions	Yield
Multi-step reaction with 6 steps 1: 1.) LDA / 1.) THF, -78 deg C, 15 min, 2.) a) -30 deg C, 3 h, b) 20 deg C, overnight 2: 1.29 g / Dibal-H / CH2Cl2; hexane / 4 h / -10 - 0 °C 3: 83 percent / Ag2CO3, Celite / benzene / 7 h / Heating 4: 1.89 g / diethyl ether / 0.33 h / -78 °C 5: CrO3, pyridine / CH2Cl2 / 0.67 h 6: NaNH2 / benzene / 2 h / Ambient temperature View Scheme

1,4-diiodo-2-methylbutane (66688-32-2) → cis-1-(trimethylsilyl)-3-methylcyclopentanemethanol (119880-34-1, 119880-35-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) LDA / 1.) THF, -78 deg C, 15 min, 2.) a) -30 deg C, 3 h, b) 20 deg C, overnight 2: 1.40 g / Dibal-H / CH2Cl2; hexane / 4 h / -10 - 0 °C View Scheme

1,4-diiodo-2-methylbutane (66688-32-2) → trans-1-(trimethylsilyl)-3-methylcyclopentanemethanol (119880-34-1, 119880-35-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) LDA / 1.) THF, -78 deg C, 15 min, 2.) a) -30 deg C, 3 h, b) 20 deg C, overnight 2: 1.29 g / Dibal-H / CH2Cl2; hexane / 4 h / -10 - 0 °C View Scheme

1,4-diiodo-2-methylbutane (66688-32-2) → (1R,3R)-3-Methyl-1-trimethylsilanyl-cyclopentanecarbaldehyde (119880-36-3, 119880-39-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) LDA / 1.) THF, -78 deg C, 15 min, 2.) a) -30 deg C, 3 h, b) 20 deg C, overnight 2: 1.40 g / Dibal-H / CH2Cl2; hexane / 4 h / -10 - 0 °C 3: 85 percent / Ag2CO3, Celite / benzene / 7 h / Heating View Scheme

1,4-diiodo-2-methylbutane (66688-32-2) → (1R,3S)-3-Methyl-1-trimethylsilanyl-cyclopentanecarbaldehyde (119880-36-3, 119880-39-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) LDA / 1.) THF, -78 deg C, 15 min, 2.) a) -30 deg C, 3 h, b) 20 deg C, overnight 2: 1.29 g / Dibal-H / CH2Cl2; hexane / 4 h / -10 - 0 °C 3: 83 percent / Ag2CO3, Celite / benzene / 7 h / Heating View Scheme

1,4-diiodo-2-methylbutane (66688-32-2) → ((1S,3S)-3-Methyl-1-trimethylsilanyl-cyclopentyl)-phenyl-methanol

Conditions	Yield
Multi-step reaction with 4 steps 1: 1.) LDA / 1.) THF, -78 deg C, 15 min, 2.) a) -30 deg C, 3 h, b) 20 deg C, overnight 2: 1.40 g / Dibal-H / CH2Cl2; hexane / 4 h / -10 - 0 °C 3: 85 percent / Ag2CO3, Celite / benzene / 7 h / Heating 4: 2.10 g / diethyl ether / 0.33 h / -78 °C View Scheme

1,4-diiodo-2-methylbutane (66688-32-2) → ((1S,3R)-3-Methyl-1-trimethylsilanyl-cyclopentyl)-phenyl-methanol

Conditions	Yield
Multi-step reaction with 4 steps 1: 1.) LDA / 1.) THF, -78 deg C, 15 min, 2.) a) -30 deg C, 3 h, b) 20 deg C, overnight 2: 1.29 g / Dibal-H / CH2Cl2; hexane / 4 h / -10 - 0 °C 3: 83 percent / Ag2CO3, Celite / benzene / 7 h / Heating 4: 1.89 g / diethyl ether / 0.33 h / -78 °C View Scheme

1,4-diiodo-2-methylbutane (66688-32-2) → trans-1-benzoyl-1-(trimethylsilyl)-3-methylcyclopentane (119880-37-4, 119880-38-5)

Conditions	Yield
Multi-step reaction with 5 steps 1: 1.) LDA / 1.) THF, -78 deg C, 15 min, 2.) a) -30 deg C, 3 h, b) 20 deg C, overnight 2: 1.40 g / Dibal-H / CH2Cl2; hexane / 4 h / -10 - 0 °C 3: 85 percent / Ag2CO3, Celite / benzene / 7 h / Heating 4: 2.10 g / diethyl ether / 0.33 h / -78 °C 5: CrO3, pyridine / CH2Cl2 / 0.67 h View Scheme

1,4-diiodo-2-methylbutane (66688-32-2) → cis-1-benzoyl-1-(trimethylsilyl)-3-methylcyclopentane (119880-37-4, 119880-38-5)

Conditions	Yield
Multi-step reaction with 5 steps 1: 1.) LDA / 1.) THF, -78 deg C, 15 min, 2.) a) -30 deg C, 3 h, b) 20 deg C, overnight 2: 1.29 g / Dibal-H / CH2Cl2; hexane / 4 h / -10 - 0 °C 3: 83 percent / Ag2CO3, Celite / benzene / 7 h / Heating 4: 1.89 g / diethyl ether / 0.33 h / -78 °C 5: CrO3, pyridine / CH2Cl2 / 0.67 h View Scheme

4-hydroxy-3,5-di-tert-butylthiophenol (950-59-4) + 4-amino-4'-ethyldiphenylamine + 1,4-diiodo-2-methylbutane (66688-32-2) + sulfur (7704-34-9) → C33H44N2OS2

Conditions	Yield
Stage #1: 4-hydroxy-3,5-di-tert-butylthiophenol; 4-amino-4'-ethyldiphenylamine; 2-methyl-1,4-diiodobutane With potassium carbonate In toluene at 90℃; for 3h; Inert atmosphere; Stage #2: sulfur With iodine In toluene at 20 - 150℃; for 8h; Inert atmosphere;

4-hydroxy-3,5-di-tert-butylthiophenol (950-59-4) + C14H14N2S + 1,4-diiodo-2-methylbutane (66688-32-2) → C33H44N2OS2

Conditions	Yield
With potassium carbonate In toluene at 90℃; for 3h; Inert atmosphere;

4-hydroxy-3,5-di-tert-butylthiophenol (950-59-4) + 4-amino-4'-ethyl-N,N-diphenylamine (60457-48-9) + 1,4-diiodo-2-methylbutane (66688-32-2) → C33H44N2OS2

Conditions	Yield
Stage #1: 4-hydroxy-3,5-di-tert-butylthiophenol; 4-amino-4'-ethyl-N,N-diphenylamine; 2-methyl-1,4-diiodobutane With potassium carbonate In toluene at 90℃; for 3h; Inert atmosphere; Stage #2: With iodine; sulfur In toluene at 150℃; for 8h; Inert atmosphere;

Upstream product

• 13423-15-9 3-methyltetrahydrofuran 
• 54462-66-7 1,4-dibromo-2-methyl-butane 

Downstream Products

• 876938-99-7 diethyl 1,1-difluoro-5-iodo-4-methylpentylphosphonate 
• 119880-37-4 trans-1-benzoyl-1-(trimethylsilyl)-3-methylcyclopentane 
• 119880-37-4 cis-1-benzoyl-1-(trimethylsilyl)-3-methylcyclopentane 

Relevant academic research and scientific papers

Cleavage of Carbon-Carbon Bonds with High Stereochemical Control. 7. Chiral α-Silyl Benzoylcycloalkanes Undergo Base-Catalysed Cleavage with Retention of Configuration When Not Sterically Congested

The cyclic phenyl ketone (-)-1 has been prepared in a manner that allows definition of its absolute configuration.On being heated with sodium and potassium amide in benzene, (-)-1 undergoes C-C bond cleavage with outstanding (96-98percent) levels of configurational retention.This conclusion required interconversion of (-)-1-(trimethylsilyl)-3-isopropylidenecyclopentane (2) with (S)-(-)-3-(trimethylsilyl)cyclopentene (3).The racemic ketones 21, 22, 36, and 37 have also been synthesized and subjected to the Haller-Bauer process.In each case, the resultant cyclic silanes were demonstrated to arise by virtually exclusive stereochemical retention.In the case of 28, an example where the benzoyl carbonyl group is sterically shielded, desilylation was the kinetically dominant reaction with these bases.These results are interpreted on the basis of initial α-silyl carbanion formation within a solvent shell that also encases benzamide.The benefits derived from these special solvational features are predicted not to be useful for extending stereocontrol to targets requiring the operation of intermediate energy-demanding steps.

A CONVENIENT METHOD FOR THE SYNTHESIS OF DIIODO COMPOUNDS. FACILE CLEAVAGE OF CYCLIC ETHERS BY PHENYL DICHLOROPHOSPHATE AND SODIUM IODIDE

Cyclic ethers were found to react readily with phenyl dichlorophosphate and sodium iodide to give diiodo compounds under mild reaction conditions.