125653-55-6

Basic information

• Product Name: (MOD)2P(O)H
• Synonyms: BIS(3,5-DIMETHYL-4-METHOXYPHENYL)PHOSPHINE OXIDE;(MOD)2P(O)H
• CAS NO: 125653-55-6
• Molecular Formula: C₁₈H₂₃O₃P
• Molecular Weight: 318.35
• Mol File: 125653-55-6.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (MOD)2P(O)H(CAS DataBase Reference)
• NIST Chemistry Reference: (MOD)2P(O)H(125653-55-6)
• EPA Substance Registry System: (MOD)2P(O)H(125653-55-6)

Safety Data

• Hazardous Substances Data: 125653-55-6(Hazardous Substances Data)

Usage

Uses

Used in Coordination Chemistry:
(MOD)2P(O)H is used as a ligand in coordination chemistry for [forming complexes with metal ions] due to [its ability to bind with metal ions, enhancing the stability and reactivity of the resulting complexes].
Used in the Production of Organophosphorus Compounds:
(MOD)2P(O)H is used as a precursor for [various organophosphorus compounds] for [its role in the synthesis of a wide range of phosphorus-containing molecules].
Used in Pesticide Production:
(MOD)2P(O)H is used in the production of pesticides for [its role in the synthesis of active ingredients] to [enhance the effectiveness of pesticides in controlling pests].
Used in Flame Retardants:
(MOD)2P(O)H is used in the production of flame retardants for [its ability to enhance the fire resistance of materials] to [improve the safety of various products].
Used in Plasticizers:
(MOD)2P(O)H is used in the production of plasticizers for [its ability to increase the flexibility and workability of plastics] to [enhance the properties of plastic materials].
Used in Organic Synthesis:
(MOD)2P(O)H is used in organic synthesis for [its role as a reagent or intermediate] to [facilitate various chemical reactions and the formation of desired products].
Used in Industrial Processes:
(MOD)2P(O)H is used as a reagent in industrial processes for [its versatility and reactivity] to [aid in the production of various chemicals and materials].

Upstream product

• 762-04-9 phosphonic acid diethyl ester 
• 185416-17-5 3,5-dimethyl-4-methoxyphenylmagnesium bromide 
• 762-04-9 Diethyl phosphonate 
• 14804-38-7 5-bromo-2-methoxy-1,3-dimethylbenzene 

Downstream Products

• 1262588-16-8 (R)-3-(bis(4-methoxy-3,5-dimethylphenyl)phosphoryl)-1,3-diphenylpropan-1-one 
• 1312366-27-0 C₂₀H₂₇O₃P 
• 136802-85-2 bis(3,5-dimethyl-4-methoxy-phenyl)chlorophosphine 
• 122708-97-8 bis(4-methoxy-3,5-dimethylphenyl)-phosphine 

Relevant articles and documents

Development of effective bidentate diphosphine ligands of ruthenium catalysts toward practical hydrogenation of carboxylic acids

Hydrogenation of carboxylic acids (CAs) to alcohols represents one of the most ideal reduction methods for utilizing abundant CAs as alternative carbon and energy sources. However, systematic studies on the effects of metal-to-ligand relationships on the catalytic activity of metal complex catalysts are scarce. We previously demonstrated a rational methodology for CA hydrogenation, in which CA-derived cationic metal carboxylate [(PP)M(OCOR)]+ (M = Ru and Re; P = one P coordination) served as the catalyst prototype for CA self-induced CA hydrogenation. Herein, we report systematic trial- and-error studies on how we could achieve higher catalytic activity by modifying the structure of bidentate diphosphine (PP) ligands of molecular Ru catalysts. Carbon chains connecting two P atoms as well as Ar groups substituted on the P atoms of PP ligands were intensively varied, and the induction of active Ru catalysts from precatalyst Ru(acac)3 was surveyed extensively. As a result, the activity and durability of the (PP)Ru catalyst substantially increased compared to those of other molecular Ru catalyst systems, including our original Ru catalysts. The results validate our approach for improving the catalyst performance, which would benefit further advancement of CA self-induced CA hydrogenation.

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.

Ruthenium-catalyzed regio- and enantioselective allylic substitution with water: Direct synthesis of chiral allylic alcohols

Less is more: A new route to access chiral allylic alcohols through the regio- and enantioselective substitution of monosubstituted allylic chlorides with water has been developed. The reaction is catalyzed effectively by planar-chiral cyclopentadienyl ruthenium complexes (see scheme). Copyright

PROCESS FOR PREPARATION OF DIPHOSPHINE COMPOUNDS AND INTERMEDIATES FOR THE PROCESS

A production method of a_compound represented by the formula wherein R1a, R1b, R1c, R1d, R1e, R1f, R2a, R2b, R2c R2d, R2e and R2f are the same or different and each is a hydrogen atom and the like, and R3, R4, R5, R6, R7, R8, R9 and R10 are the same or different and each is a hydrogen atom and the like, or a salt thereof, which comprises reacting a compound represented by the formula wherein X is a leaving group and other symbols are as defined above, or a salt thereof, with a phosphine-borane complex represented by the formula wherein the symbols are as defined above, or a salt thereof, in a solvent in the presence of an amine and a nickel catalyst, is provided.

Electronic and steric effects of ligands as control elements for rhodium-catalyzed asymmetric hydrogenation

Chiral diphosphine ligands analogous to bdpp have been synthesized and tested in order to study the effect of the electronic nature of the ligands in Rh-catalyzed asymmetric hydrogenation of some prochiral olefins. The results are compared with those obtained with the analogous unsubstituted ligand (bdpp). The rhodium-catalyzed asymmetric hydrogenation of olefins was influenced by ligand-based electronic effects, as well as substrate based ones. Excellent ee's (up to 98.3%) have been obtained in the rhodium-catalyzed hydrogenation of (Z)-α-acetamidocinnamic acids and esters.