12154-63-1

Basic information

• Product Name: TRICARBONYL(1,2,3,4-TETRAHYDRONAPHTHALENE)CHROMIUM
• Synonyms: TRICARBONYL(1,2,3,4-TETRAHYDRONAPHTHALENE)CHROMIUM;tricarbonyl(1,2,3,4-tetrahydronaphthalene) -chrom;tricarbonyl[(4a,5,6,7,8,8a-eta)-1,2,3,4-tetrahydronaphthalene]chromium;tricarbonyl(1,2,3,4-tetrahydronaphthalene)chromium(0);1,2,3,4-tetrahydronaphthalene chromium tricarbonyl;Einecs 235-274-2
• CAS NO: 12154-63-1
• Molecular Formula: C₁₃H₁₂CrO₃
• Molecular Weight: 268.23
• EINECS: 235-274-2
• Mol File: 12154-63-1.mol
• Article Data: 8

Chemical Properties

• Melting Point: 115-118 °C(lit.)
• Boiling Point: 210.3°Cat760mmHg
• Flash Point: 77.2°C
• Appearance: /
• Density: g/cm³
• Vapor Pressure: 0.281mmHg at 25°C
• CAS DataBase Reference: TRICARBONYL(1,2,3,4-TETRAHYDRONAPHTHALENE)CHROMIUM(CAS DataBase Reference)
• NIST Chemistry Reference: TRICARBONYL(1,2,3,4-TETRAHYDRONAPHTHALENE)CHROMIUM(12154-63-1)
• EPA Substance Registry System: TRICARBONYL(1,2,3,4-TETRAHYDRONAPHTHALENE)CHROMIUM(12154-63-1)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36
• RIDADR: 3282
• WGK Germany: 3
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 12154-63-1(Hazardous Substances Data)

Usage

General Description

TRICARBONYL(1,2,3,4-TETRAHYDRONAPHTHALENE)CHROMIUM is a compound that consists of a chromium atom bonded to a tetrahydronaphthalene molecule and three carbonyl groups. It is commonly used as a catalyst in organic chemistry reactions, particularly in hydrogenation and carbonylation reactions. The compound is known for its ability to selectively catalyze certain types of reactions, making it a valuable tool in synthetic chemistry. It is also used in the production of various organic compounds and materials. However, it is important to handle TRICARBONYL(1,2,3,4-TETRAHYDRONAPHTHALENE)CHROMIUM with care, as chromium compounds can be toxic and harmful if not handled properly.

InChI:InChI=1/C10H12.3CO.Cr/c1-2-6-10-8-4-3-7-9(10)5-1;3*1-2;/h1-2,5-6H,3-4,7-8H2;;;;

Upstream product

• 119-64-2 tetralin 
• 41371-94-2 tris(ammonia)chromium tricarbonyl 
• 130495-59-9 C₈H₆(O₂CH₂CH₂)Cr(CO)3 
• 624-49-7 dimethylfumarate 
• 199620-14-9 chromium⁽⁰⁾ hexacarbonyl 
• 91-20-3 naphthalene 
• 12129-27-0 (η6-p-xylene)tricarbonylchromium(0) 
• 108-90-7 chlorobenzene 
• 14044-65-6 borane-THF 
• 12110-40-6 (η(6)-1,2-dihydronaphthalene)chromium tricarbonyl 

Downstream Products

• 13577-40-7 1-(5,6,7,8-tetrahydro-naphthalen-1-yl)-ethanone 
• 1245715-12-1 Cr(CO)3(η6-C6H4C4H7(C6H4CH3)) 
• 1245715-13-2 Cr(CO)3(η6-C6H4C4H7(C6H4N(CH3)2)) 
• 157109-23-4 1-phenyl-(η(6)-1,2,3,4-tetrahydronaphthalene)chromiumtricarbonyl 
• 3160-17-6 2-(5,6,7,8-tetrahydronaphthalene-1-yl)acetonitrile 

Relevant articles and documents

Hydroboration, followed by water addition of benchrotrenic alkenes. Formal dihydrogen addition

The reaction of the BH3-THF reagent with benchrotrenic alkenes, followed by a water addition and the formation of hydrogenated products are described. This formation and the regioselectivity observed is a consequence of the electron withdrawing effect of the Cr(CO)3 group.

Palladium-catalyzed allylic substitution with (η6-Arene- CH2Z)Cr(CO)3-based nucleophiles

Although the palladium-catalyzed Tsuji-Trost allylic substitution reaction has been intensively studied, there is a lack of general methods to employ simple benzylic nucleophiles. Such a method would facilitate access to "α-2-propenyl benzyl" motifs, which are common structural motifs in bioactive compounds and natural products. We report herein the palladium-catalyzed allylation reaction of toluene-derived pronucleophiles activated by tricarbonylchromium. A variety of cyclic and acyclic allylic electrophiles can be employed with in situ generated (η6-C 6H5CHLiR)Cr(CO)3 nucleophiles. Catalyst identification was performed by high throughput experimentation (HTE) and led to the Xantphos/palladium hit, which proved to be a general catalyst for this class of reactions. In addition to η6-toluene complexes, benzyl amine and ether derivatives (η6-C6H5CH 2Z)Cr(CO)3 (Z = NR2, OR) are also viable pronucleophiles, allowing C-C bond-formation α to heteroatoms with excellent yields. Finally, a tandem allylic substitution/demetalation procedure is described that affords the corresponding metal-free allylic substitution products. This method will be a valuable complement to the existing arsenal of nucleophiles with applications in allylic substitution reactions.

Synthesis, Characterization, and Some Reactions of Tricarbonyl(cyclobutabenzene)chromium(0) Derivatives

The tricarbonyl(cyclobutabenzene)chromium(0) complexes 12-20, have been prepared from the free ligand and triammin-tricarbonylchromium(0) or hexacarbonylchromium(0).The complexes have been characterized by spectroscopic methods (IR, 1H NMR, 13C NMR) and mass spectrometry, and 1H-NMR signal assignments have been verified by an NOE experiment.Diastereomeric ratios have been determined by 1H NMR and the diasteromers of the 1-methyl derivative 16 separated by HPLC.A crystal-structure analysis is presented for exo-16.A photochemical ligand exchange takes place in 70percent yield for the 1-trimethylsilyl derivative 19.Metalation with n-butyllithium/tmeda at -78 deg C has been observed only for aromatic and not for the benzylic protons.