136802-85-2

Basic information

• Product Name: BIS(3,5-DIMETHYL-4-METHOXYPHENYL)CHLOROPHOSPHINE
• Synonyms: BIS(3,5-DIMETHYL-4-METHOXYPHENYL)CHLOROPHOSPHINE;Chlorobis(3,5-dimethyl-4-methoxyphenyl)phosphine, 98+%;Bis(3,5-diMethyl-4-Methoxyphenyl)chlorophosphine,Min.98%;chloro-bis(4-methoxy-3,5-dimethylphenyl)phosphane
• CAS NO: 136802-85-2
• Molecular Formula: C₁₈H₂₂ClO₂P
• Molecular Weight: 336.79
• Product Categories: organophosphine ligand
• Mol File: 136802-85-2.mol

Chemical Properties

• Boiling Point: 451.7°C at 760 mmHg
• Flash Point: >110℃
• Appearance: colorless, viscous/liquid
• Density: 1.141 g/cm 3 at 25 °C
• Vapor Pressure: 6.37E-08mmHg at 25°C
• Refractive Index: n20/D1.597
• Sensitive: Moisture Sensitive
• CAS DataBase Reference: BIS(3,5-DIMETHYL-4-METHOXYPHENYL)CHLOROPHOSPHINE(CAS DataBase Reference)
• NIST Chemistry Reference: BIS(3,5-DIMETHYL-4-METHOXYPHENYL)CHLOROPHOSPHINE(136802-85-2)
• EPA Substance Registry System: BIS(3,5-DIMETHYL-4-METHOXYPHENYL)CHLOROPHOSPHINE(136802-85-2)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-43-45
• RIDADR: UN3265
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 136802-85-2(Hazardous Substances Data)

Usage

Uses

Used in Asymmetric Organocatalytic Electrophilic Phosphination:
BIS(3,5-DIMETHYL-4-METHOXYPHENYL)CHLOROPHOSPHINE is used as a reagent for asymmetric organocatalytic electrophilic phosphination. Its unique structure allows for selective phosphination reactions, leading to the formation of chiral phosphines with high enantioselectivity.
Used in Asymmetric Hydroformulation using Taddol-based Chiral Phosphine-Phosphite Ligands:
In the field of asymmetric hydroformulation, BIS(3,5-DIMETHYL-4-METHOXYPHENYL)CHLOROPHOSPHINE serves as a key component in the synthesis of Taddol-based chiral phosphine-phosphite ligands. These ligands are crucial for the selective formation of aldehydes with high enantiomeric excess in hydroformulation reactions.
Used in Synthesis of Ferrocene-based Chiral Diphosphines:
BIS(3,5-DIMETHYL-4-METHOXYPHENYL)CHLOROPHOSPHINE is utilized as a starting material in the synthesis of ferrocene-based chiral diphosphines. These diphosphines are valuable catalysts in various homogeneous catalytic reactions, such as hydrogenation and hydroformylation, due to their unique electronic and steric properties.
Used in Alcoholysis of Phosphane-Boranes:
BIS(3,5-DIMETHYL-4-METHOXYPHENYL)CHLOROPHOSPHINE is also employed as a reactant in the alcoholysis of phosphane-boranes. The reaction results in the formation of phosphine-borane adducts, which are useful intermediates in the synthesis of various phosphorus-containing compounds.
Used in Asymmetric Hydrogenations of Bifep-type Biferrocenes:
BIS(3,5-DIMETHYL-4-METHOXYPHENYL)CHLOROPHOSPHINE is used as a catalyst in asymmetric hydrogenations of bifep-type biferrocenes. The compound's unique structure enables the selective reduction of prochiral substrates, leading to the formation of chiral products with high enantioselectivity.

InChI:InChI=1/C18H22ClO2P/c1-11-7-15(8-12(2)17(11)20-5)22(19)16-9-13(3)18(21-6)14(4)10-16/h7-10H,1-6H3

Upstream product

• 14804-38-7 5-bromo-2-methoxy-1,3-dimethylbenzene 
• 125653-55-6 bis(4-methoxy-3,5-dimethylphenyl)phosphine oxide 

Downstream Products

• 358721-83-2 (S,S(p),S(p))-2-bis(3,5-dimethyl-4-methoxyphenyl)phosphino-2''-(4-methylphenyl)sulfinyl-1,1''-biferrocene 
• 1365531-93-6 (R)-2,2’-bis[bis(4-methoxyl-3,5-dimethylphenyl)phosphino]-,4’,6,6’,tetramethoxylbiphenyl 
• 1365320-24-6 (R,S)-(4,4',6,6'-tetramethoxybiphenyl-2,2'-diyl)bis(bis(4-methoxy-3,5-dimethylphenyl)phosphineoxide) 
• 1365320-22-4 (2-bromo-3,5-dimethoxyphenyl)bis(4-methoxy-3,5-dimethylphenyl)phosphine oxide 
• 1157863-54-1 o-bromophenylbis(3,5-dimethyl-4-methoxyphenyl)phosphine 
• 1015074-86-8 C₅₀H₅₈Br₂FeO₄P₂ 

Relevant articles and documents

Asymmetric hydrogenation reactions mediated by a new class of bicyclic bisphosphinites

The bicyclic alcohol (-)-4 was prepared from (-)-bicyclo[3.2.0]hept-2- en-6-one (-)-1 in 50% yield. The diol (-)-4 was coupled to selected chlorophosphines 6-12 to produce a series of bisphosphinites 13-19 in 89-95% yield. From these bisphosphinites were prepared the rhodium complexes 20-26 which were characterised by 31P NMR and used in situ for the asymmetric hydrogenation of α-enamides 27-29. Complexes 21, 23-25 proved to be the superior catalysts for the production of (R)-N-acetylphenylalanine (91, 84, 90 and 87.5% ee) from 27 and (S)-N-acetylalanine methyl ester (70, 72, 68 and 71% ee) from 28.

Asymmetric Hydrogenation of Cationic Intermediates for the Synthesis of Chiral N,O-Acetals

For over half a century, transition-metal-catalyzed homogeneous hydrogenation has been mainly focused on neutral and readily prepared unsaturated substrates. Although the addition of molecular hydrogen to C=C, C=N, and C=O bonds represents a well-studied paradigm, the asymmetric hydrogenation of cationic species remains an underdeveloped area. In this study, we were seeking a breakthrough in asymmetric hydrogenation, with cationic intermediates as targets, and thereby anticipating applying this powerful tool to the construction of challenging chiral molecules. Under acidic conditions, both N- or O-acetylsalicylamides underwent cyclization to generate cationic intermediates, which were subsequently reduced by an iridium or rhodium hydride complex. The resulting N,O-acetals were synthesized with remarkably high enantioselectivity. This catalytic strategy exhibited high efficiency (turnover number of up to 4400) and high chemoselectivity. Mechanistic studies supported the hypothesis that a cationic intermediate was formed in situ and hydrogenated afterwards. A catalytic cycle has been proposed with hydride transfer from the iridium complex to the cationic sp2 carbon atom being the rate-determining step. A steric map of the catalyst has been created to illustrate the chiral environment, and a quantitative structure–selectivity relationship analysis showed how enantiomeric induction was achieved in this chemical transformation.

Chiral phosphorus-based ligands

A chiral phosphorus-based ligand, in single enantiomer form, which is capable of complexing a transition metal atom and of acting as a ligand in asymmetric chemical catalysts, which comprises the partial structureR1R2P-O-C-X-Y-C-O-PR1R2(I)wherein each of

Selective asymmetric hydrogenation of dehydroamino acid derivatives using rhodium and iridium diphosphinite carbohydrate catalyst compositions

A process and catalyst composition are provided for the highly efficient enantioselective hydrogenation of dehydroamino acid derivatives. The catalyst composition comprises rhodium or iridium and a diphosphinite carbohydrate ligand, wherein the phosphorous atoms are attached to aromatic groups substituted with electron-donating substituents. Also provided is a means to selectively produce α amino acids in either the L or the D form, based upon use of a sugar in the ligand with phosphinites attached in an absolute Right-Left or Left-Right configuration, respectively.