# Latest **URL:** https://chemdotes.discourse.group/latest.md [Latest](https://chemdotes.discourse.group/latest.md) · [Categories](https://chemdotes.discourse.group/categories.md) · [Tags](https://chemdotes.discourse.group/tags.md) --- ## [Welcome to ChemDotes Synthetic Companion! 👋](https://chemdotes.discourse.group/t/welcome-to-chemdotes-synthetic-companion/5)
**Author:** [@system](https://chemdotes.discourse.group/u/system)\ **Replies:** 0\ **Last updated:** [July 6, 2023, 8:19pm UTC](https://chemdotes.discourse.group/t/welcome-to-chemdotes-synthetic-companion/5 "2023-07-06T20:19:51Z")
We are so glad you joined us. ChemDotes Synthetic Companion A place for consulting and discussing reliable synthetic protocols Here are some things you can do to get started: :speaking\_head: Introduce yourself by ad… --- ## [Silicontetrabromide (SiBr4)](https://chemdotes.discourse.group/t/silicontetrabromide-sibr4/79)
**Author:** [@Oussama](https://chemdotes.discourse.group/u/Oussama)\ **Replies:** 0\ **Last updated:** [August 27, 2025, 3:06pm UTC](https://chemdotes.discourse.group/t/silicontetrabromide-sibr4/79 "2025-08-27T15:06:41Z")
Silicon tetrabromide is a versatile starting compound, particularly for synthesising different silylenes. Although it is expensive to purchase directly, it can be easily prepared in small quantities. Traditional large-sc… --- ## [N-(2,6-diisopropylphenyl)imidazole](https://chemdotes.discourse.group/t/n-2-6-diisopropylphenyl-imidazole/29)
**Author:** [@bmpuerta](https://chemdotes.discourse.group/u/bmpuerta)\ **Replies:** 0\ **Last updated:** [February 23, 2024, 2:45am UTC](https://chemdotes.discourse.group/t/n-2-6-diisopropylphenyl-imidazole/29 "2024-02-23T02:45:12Z")
N-(2,6-diisopropylphenyl)imidazole can be synthesized on multigram scales via the four-step sequence below, which is adapted from a literature procedure:\[1\] Synthesis of N-(2,6-diisopropylphenyl)isothiocyanate.\[2\] To a … --- ## [1,3-Bis(2,6-diisopropylphenyl)imidazolium salts (IPrHX) (250285-32-6)](https://chemdotes.discourse.group/t/1-3-bis-2-6-diisopropylphenyl-imidazolium-salts-iprhx-250285-32-6/73)
**Author:** [@bmpuerta](https://chemdotes.discourse.group/u/bmpuerta)\ **Replies:** 0\ **Last updated:** [April 12, 2024, 11:06pm UTC](https://chemdotes.discourse.group/t/1-3-bis-2-6-diisopropylphenyl-imidazolium-salts-iprhx-250285-32-6/73 "2024-04-12T23:06:08Z")
N-heterocyclic carbenes are sources of divalent carbon that have made tremendous impact in many areas of synthetic chemistry since their first report in 1991 by Arduengo and colleagues.\[1\] These compounds can be convenie… --- ## [Na2\[Fe(CO)4\] (Collman's reagent) (14878-31-0)](https://chemdotes.discourse.group/t/na2-fe-co-4-collmans-reagent-14878-31-0/72)
**Author:** [@bmpuerta](https://chemdotes.discourse.group/u/bmpuerta)\ **Replies:** 0\ **Last updated:** [April 11, 2024, 3:03am UTC](https://chemdotes.discourse.group/t/na2-fe-co-4-collmans-reagent-14878-31-0/72 "2024-04-11T03:03:37Z")
Sodium tetracarbonylferrate, better known as Collman’s reagent, is an electron-rich iron complex that has found use in organic synthesis. Namely, in the conversion of alkyl halides/sulfonates to carbonyl-containing compo… --- ## [Phosphatrioxa-adamantane (CgPH) (26088-25-5)](https://chemdotes.discourse.group/t/phosphatrioxa-adamantane-cgph-26088-25-5/71)
**Author:** [@bmpuerta](https://chemdotes.discourse.group/u/bmpuerta)\ **Replies:** 0\ **Last updated:** [April 8, 2024, 6:46am UTC](https://chemdotes.discourse.group/t/phosphatrioxa-adamantane-cgph-26088-25-5/71 "2024-04-08T06:46:40Z")
The parent 6-phospha-2,4,8-trioxa-1,3,5,7-tetramethyladamantane (CgPH) is a phosphine with a rather esoteric structure. It was first reported in 1961 by the group of Buckler while investigating the reactions of PH3 with … --- ## [Fe(acetylacetonate)3 (14024-18-1)](https://chemdotes.discourse.group/t/fe-acetylacetonate-3-14024-18-1/70)
**Author:** [@bmpuerta](https://chemdotes.discourse.group/u/bmpuerta)\ **Replies:** 0\ **Last updated:** [April 3, 2024, 3:47pm UTC](https://chemdotes.discourse.group/t/fe-acetylacetonate-3-14024-18-1/70 "2024-04-03T15:47:08Z")
Among all iron catalysts employed in organic synthesis, tris(acetylacetonato)iron(III) or Fe(acac)3 is one the most popular. This is, in part, because it is air stable, easy to make, and soluble in organic solvents. It h… --- ## [RhCl(PPh3)3 (Wilkinson's catalyst) (14694-95-2)](https://chemdotes.discourse.group/t/rhcl-pph3-3-wilkinsons-catalyst-14694-95-2/69)
**Author:** [@bmpuerta](https://chemdotes.discourse.group/u/bmpuerta)\ **Replies:** 0\ **Last updated:** [March 30, 2024, 11:37pm UTC](https://chemdotes.discourse.group/t/rhcl-pph3-3-wilkinsons-catalyst-14694-95-2/69 "2024-03-30T23:37:43Z")
Wilkinson’s catalyst is a burgundy-colored solid featuring a central rhodium(I) in a 16-electron, square-planar coordination environment. First reported by Osborn and Wilkinson in 1966,\[1\] the complex became a centerpiec… --- ## [Pd2(dibenzylideneacetone)3 (51364-51-3)](https://chemdotes.discourse.group/t/pd2-dibenzylideneacetone-3-51364-51-3/67)
**Author:** [@bmpuerta](https://chemdotes.discourse.group/u/bmpuerta)\ **Replies:** 0\ **Last updated:** [March 29, 2024, 3:49am UTC](https://chemdotes.discourse.group/t/pd2-dibenzylideneacetone-3-51364-51-3/67 "2024-03-29T03:49:39Z")
Palladium-based complexes comprise some of the most important catalysts in synthetic chemistry. Its ability to reliably and cyclically effect two-electron bond-forming and bond-breaking processes has made palladium the g… --- ## [Tricyclohexylphosphine (PCy3) (2622-14-2)](https://chemdotes.discourse.group/t/tricyclohexylphosphine-pcy3-2622-14-2/66)
**Author:** [@bmpuerta](https://chemdotes.discourse.group/u/bmpuerta)\ **Replies:** 0\ **Last updated:** [March 28, 2024, 5:33am UTC](https://chemdotes.discourse.group/t/tricyclohexylphosphine-pcy3-2622-14-2/66 "2024-03-28T05:33:46Z")
Tertiary phosphines are some of the most well known ligands employed in transition metal reactivity and catalysis. Many of the best performing homogeneous catalysts are stabilized by phosphines. For example, Wilkinson’s … --- ## [Crystalline hydrogen peroxide solvates (peroxosolvates)](https://chemdotes.discourse.group/t/crystalline-hydrogen-peroxide-solvates-peroxosolvates/65)
**Author:** [@bmpuerta](https://chemdotes.discourse.group/u/bmpuerta)\ **Replies:** 0\ **Last updated:** [March 27, 2024, 6:02am UTC](https://chemdotes.discourse.group/t/crystalline-hydrogen-peroxide-solvates-peroxosolvates/65 "2024-03-27T06:02:26Z")
While hydrogen peroxide is a ubiquitous chemical routinely used in oxidative chemistry, it is purchased as an aqueous solution.\[1\] This is due to the inherent dangers associated with its concentrated form. In addition, i… --- ## [Cu(acetonitrile)4 tetrafluoroborate (15418-29-8)](https://chemdotes.discourse.group/t/cu-acetonitrile-4-tetrafluoroborate-15418-29-8/63)
**Author:** [@bmpuerta](https://chemdotes.discourse.group/u/bmpuerta)\ **Replies:** 0\ **Last updated:** [March 26, 2024, 5:08am UTC](https://chemdotes.discourse.group/t/cu-acetonitrile-4-tetrafluoroborate-15418-29-8/63 "2024-03-26T05:08:01Z")
Copper(I) halide complexes such as CuI are routinely used in catalytic and material applications, such as catalysts in the Ullmann coupling and as p-type semiconductors, respectively.\[1\] However, these compounds typicall… --- ## [ThCl4(dimethoxyethane)2 (639084-65-4)](https://chemdotes.discourse.group/t/thcl4-dimethoxyethane-2-639084-65-4/61)
**Author:** [@bmpuerta](https://chemdotes.discourse.group/u/bmpuerta)\ **Replies:** 0\ **Last updated:** [March 25, 2024, 4:42am UTC](https://chemdotes.discourse.group/t/thcl4-dimethoxyethane-2-639084-65-4/61 "2024-03-25T04:42:17Z")
Among the actinides, uranium and thorium are the most abundant in the earth’s crust due their long-lived isotopes (thorium-232 and uranium-238). These tend to be found in the form of oxides such as thoria (ThO2) and uran… --- ## [FeBr2(dimethoxyethane) (99611-53-7)](https://chemdotes.discourse.group/t/febr2-dimethoxyethane-99611-53-7/60)
**Author:** [@bmpuerta](https://chemdotes.discourse.group/u/bmpuerta)\ **Replies:** 0\ **Last updated:** [March 24, 2024, 12:12am UTC](https://chemdotes.discourse.group/t/febr2-dimethoxyethane-99611-53-7/60 "2024-03-24T00:12:03Z")
Dihalide complexes of iron(II) have found use as a starting platform to more eleborate Fe(II) complexes, and as a catalyst in cross-coupling reactions.\[1\] A source of soluble iron(II) dihalide, FeBr2(dme) can be easily s… --- ## [RhCl(1,5-cyclooctadiene) dimer (12092-47-6)](https://chemdotes.discourse.group/t/rhcl-1-5-cyclooctadiene-dimer-12092-47-6/41)
**Author:** [@bmpuerta](https://chemdotes.discourse.group/u/bmpuerta)\ **Replies:** 0\ **Last updated:** [March 12, 2024, 12:20am UTC](https://chemdotes.discourse.group/t/rhcl-1-5-cyclooctadiene-dimer-12092-47-6/41 "2024-03-12T00:20:08Z")
RhCl(1,5-cyclooctadiene) dimer is a tremendously useful Rh(I) source due to its solubility in organic solvents and easy removal of the cyclooctadiene ligand for further derivatization. It is largely used for catalytic hy… --- ## [PtCl2(1,5-cyclooctadiene) (12080-32-9)](https://chemdotes.discourse.group/t/ptcl2-1-5-cyclooctadiene-12080-32-9/40)
**Author:** [@bmpuerta](https://chemdotes.discourse.group/u/bmpuerta)\ **Replies:** 0\ **Last updated:** [March 8, 2024, 7:19pm UTC](https://chemdotes.discourse.group/t/ptcl2-1-5-cyclooctadiene-12080-32-9/40 "2024-03-08T19:19:41Z")
Dichloro(1,5-cyclooctadiene)platinum(II) can be conveniently synthesized via the procedure from Holst et al.\[1\] Procedure: In air, a 100mL round-bottom flask was charged with a magnetic stir bar, potassium tetrachloropl… --- ## [FeCl2(pyridine)4 (Yellow salt) (15138-92-8)](https://chemdotes.discourse.group/t/fecl2-pyridine-4-yellow-salt-15138-92-8/49)
**Author:** [@bmpuerta](https://chemdotes.discourse.group/u/bmpuerta)\ **Replies:** 0\ **Last updated:** [March 19, 2024, 7:31pm UTC](https://chemdotes.discourse.group/t/fecl2-pyridine-4-yellow-salt-15138-92-8/49 "2024-03-19T19:31:48Z")
Soluble iron(II) dihalide complexes with labile ligands are useful sources of iron for a large number of applications: Catalytic reactions such as hydrogenation and hydroformylation, mechanistic studies, studies of trans… --- ## [NiCl2(dimethoxyethane) (29046-78-4)](https://chemdotes.discourse.group/t/nicl2-dimethoxyethane-29046-78-4/37)
**Author:** [@bmpuerta](https://chemdotes.discourse.group/u/bmpuerta)\ **Replies:** 0\ **Last updated:** [March 5, 2024, 5:03pm UTC](https://chemdotes.discourse.group/t/nicl2-dimethoxyethane-29046-78-4/37 "2024-03-05T17:03:11Z")
The most common source of nickel dihalide reagents are the hexahydrates, which tend to be poorly soluble in organic solvents. Furthermore, the use of nickel complexes in synthetic applications often requires anhydrous co… --- ## [NiBr2(dimethoxyethane) (28923-39-9)](https://chemdotes.discourse.group/t/nibr2-dimethoxyethane-28923-39-9/48)
**Author:** [@bmpuerta](https://chemdotes.discourse.group/u/bmpuerta)\ **Replies:** 0\ **Last updated:** [March 19, 2024, 5:49am UTC](https://chemdotes.discourse.group/t/nibr2-dimethoxyethane-28923-39-9/48 "2024-03-19T05:49:20Z")
Although simple nickel dihalides may seem as attractive Ni(II) sources in organometallic/transition-metal chemistry, they exhibit poor solubility in organic solvents. Furthermore, the use of nickel complexes in synthetic… --- ## [CoBr2(dimethoxyethane) (18346-57-1)](https://chemdotes.discourse.group/t/cobr2-dimethoxyethane-18346-57-1/51)
**Author:** [@bmpuerta](https://chemdotes.discourse.group/u/bmpuerta)\ **Replies:** 0\ **Last updated:** [March 21, 2024, 4:35pm UTC](https://chemdotes.discourse.group/t/cobr2-dimethoxyethane-18346-57-1/51 "2024-03-21T16:35:36Z")
Dihalide complexes of cobalt(II) have found use as catalysts in a variety of organic transformations. For example, C-N and C-C cross coupling reactions (Buchwald-Hartwig, Susuki, Kumada, Heck), functional group transfor… --- ## [NbCl3(dimethoxyethane) (110615-13-9)](https://chemdotes.discourse.group/t/nbcl3-dimethoxyethane-110615-13-9/43)
**Author:** [@bmpuerta](https://chemdotes.discourse.group/u/bmpuerta)\ **Replies:** 0\ **Last updated:** [March 13, 2024, 3:34am UTC](https://chemdotes.discourse.group/t/nbcl3-dimethoxyethane-110615-13-9/43 "2024-03-13T03:34:49Z")
NbCl3(dme) provides a convenient gateway into niobium(III) complexes. Due to its d2 configuration, it tends to exhibit Lewis basic behavior towards pi-ligands such as olefins. These types of complexes have found use in … --- ## [NbCl4(tetrahydrofuran)2 (61247-57-2)](https://chemdotes.discourse.group/t/nbcl4-tetrahydrofuran-2-61247-57-2/44)
**Author:** [@bmpuerta](https://chemdotes.discourse.group/u/bmpuerta)\ **Replies:** 0\ **Last updated:** [March 13, 2024, 6:47pm UTC](https://chemdotes.discourse.group/t/nbcl4-tetrahydrofuran-2-61247-57-2/44 "2024-03-13T18:47:36Z")
NbCl4(thf)2 provides a convenient gateway into niobium(IV) complexes due to its easily displaced THF ligands. While the chemistry of these types of complexes is underexplored, Nb(IV) has found use in reductive homocoupli… --- ## [NbCl2(pyridine)4 (168701-43-7)](https://chemdotes.discourse.group/t/nbcl2-pyridine-4-168701-43-7/45)
**Author:** [@bmpuerta](https://chemdotes.discourse.group/u/bmpuerta)\ **Replies:** 0\ **Last updated:** [March 14, 2024, 4:53pm UTC](https://chemdotes.discourse.group/t/nbcl2-pyridine-4-168701-43-7/45 "2024-03-14T16:53:19Z")
NbCl2(pyridine)4 provides a practical gateway into niobium(II) chemistry, a very rare oxidation state for the element. It can be synthesized via reduction according to the procedure of Cotton and Murillo.\[1\] Procedure: … --- ## [Nb(mesitylene)2 (68088-96-0)](https://chemdotes.discourse.group/t/nb-mesitylene-2-68088-96-0/46)
**Author:** [@bmpuerta](https://chemdotes.discourse.group/u/bmpuerta)\ **Replies:** 0\ **Last updated:** [March 15, 2024, 7:50pm UTC](https://chemdotes.discourse.group/t/nb-mesitylene-2-68088-96-0/46 "2024-03-15T19:50:43Z")
Nb(mesitylene)2 is a rare instance of niobium(0). This deep red, paramagnetic, 17 valence-electron complex has been used in the materials community as a source of niobium atoms for the synthesis of Nb-chalcogenide solids… --- ## [Cyclopentadienylthallium (CpTl) (34822-90-7)](https://chemdotes.discourse.group/t/cyclopentadienylthallium-cptl-34822-90-7/52)
**Author:** [@bmpuerta](https://chemdotes.discourse.group/u/bmpuerta)\ **Replies:** 0\ **Last updated:** [March 22, 2024, 4:09pm UTC](https://chemdotes.discourse.group/t/cyclopentadienylthallium-cptl-34822-90-7/52 "2024-03-22T16:09:51Z")
As one of the most versatile ligands in an organometallic chemist’s toolkit, cyclopentadienyl (Cp) has yielded complexes with elements from every block of the periodic table (s, p, d, f). In this regard, Cp-transfer agen… --- ## [tert-Butyl Hypochlorite (tBuOCl) (507-40-4)](https://chemdotes.discourse.group/t/tert-butyl-hypochlorite-tbuocl-507-40-4/50)
**Author:** [@bmpuerta](https://chemdotes.discourse.group/u/bmpuerta)\ **Replies:** 0\ **Last updated:** [March 20, 2024, 6:07pm UTC](https://chemdotes.discourse.group/t/tert-butyl-hypochlorite-tbuocl-507-40-4/50 "2024-03-20T18:07:41Z")
tert-butyl hypochlorite is a useful oxidant due to its solubility in organic solvents and versatility. It is worth having in the toolkit as it mediates radical chlorination without the need for Cl2 gas, and transforms va… --- ## [Potassium graphite (KC8) (12081-88-8)](https://chemdotes.discourse.group/t/potassium-graphite-kc8-12081-88-8/20)
**Author:** [@bmpuerta](https://chemdotes.discourse.group/u/bmpuerta)\ **Replies:** 0\ **Last updated:** [July 7, 2023, 2:26pm UTC](https://chemdotes.discourse.group/t/potassium-graphite-kc8-12081-88-8/20 "2023-07-07T14:26:58Z")
This graphite-intercalation compound boasts increased reduction power in comparison to naked potassium due to both increased reagent surface area and electron delocalization along the graphene pi framework. The reduction… --- ## [Organic silyl diene reductants (Mashima's reagent)](https://chemdotes.discourse.group/t/organic-silyl-diene-reductants-mashimas-reagent/47)
**Author:** [@bmpuerta](https://chemdotes.discourse.group/u/bmpuerta)\ **Replies:** 0\ **Last updated:** [March 17, 2024, 12:04am UTC](https://chemdotes.discourse.group/t/organic-silyl-diene-reductants-mashimas-reagent/47 "2024-03-17T00:04:07Z")
Organic silyl diene reductants have gained traction as soluble, salt-free reducing agents in synthetic chemistry, particularly within transition-metal and main-group disciplines. They were developed by Tsurugi and Mashim… --- ## [1,2,3,4,5-pentamethylcyclopentadiene (4045-44-7)](https://chemdotes.discourse.group/t/1-2-3-4-5-pentamethylcyclopentadiene-4045-44-7/42)
**Author:** [@bmpuerta](https://chemdotes.discourse.group/u/bmpuerta)\ **Replies:** 0\ **Last updated:** [March 12, 2024, 5:26am UTC](https://chemdotes.discourse.group/t/1-2-3-4-5-pentamethylcyclopentadiene-4045-44-7/42 "2024-03-12T05:26:37Z")
1,2,3,4,5-pentamethylcyclopentadiene (Cp\*) is an organic molecule that serves as precursor to the well known Cp\* ligand in organometallic chemistry. It possesses an acidic proton that is typically removed with organolith… --- ## [Hydrogen bromide gas (10035-10-6)](https://chemdotes.discourse.group/t/hydrogen-bromide-gas-10035-10-6/39)
**Author:** [@bmpuerta](https://chemdotes.discourse.group/u/bmpuerta)\ **Replies:** 0\ **Last updated:** [March 8, 2024, 4:45am UTC](https://chemdotes.discourse.group/t/hydrogen-bromide-gas-10035-10-6/39 "2024-03-08T04:45:18Z")
Although there are several ways of making hydrogen bromide in the literature, I have successfully used the method below when I needed the reagent for anti-Markovnikov hydrobromination of alkenes. It has turned out to be … [Next page](https://chemdotes.discourse.group/latest.md?page=1)