Tri(chloromethyl)phosphine oxide

Base Information

• Chemical Name: Tri(chloromethyl)phosphine oxide
• CAS No.: 4851-89-2
• Molecular Formula: C3H6Cl3OP
• Molecular Weight: 195.413
• NSC Number: 222442
• UNII: BL5AGC2ESB
• DSSTox Substance ID: DTXSID8063624
• Nikkaji Number: J421.742J
• Wikidata: Q81990878
• Mol file: 4851-89-2.mol

Synonyms:Tri(chloromethyl)phosphine oxide;Tris(chloromethyl)phosphine oxide;Phosphine oxide, tris(chloromethyl)-;4851-89-2;NSC 222442;NSC-222442;[bis(chloromethyl)phosphoryl](chloro)methane;Phosphine oxide, tris[chloromethyl]-;bis(chloromethyl)phosphoryl-chloromethane;BL5AGC2ESB;C3H6Cl3OP;SCHEMBL258515;C3-H6-Cl3-O-P;DTXSID8063624;NSC222442

Chemical Property of Tri(chloromethyl)phosphine oxide

Chemical Property:

• Vapor Pressure: 8.26E-05mmHg at 25°C
• Boiling Point: 351.6°Cat760mmHg
• Flash Point: 166.4°C
• PSA: 26.88000
• Density: 1.433g/cm³
• LogP: 2.93840
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 193.922185
• Heavy Atom Count: 8
• Complexity: 85.7

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C(P(=O)(CCl)CCl)Cl

Technology Process of Tri(chloromethyl)phosphine oxide

There total 4 articles about Tri(chloromethyl)phosphine oxide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

tris<(trimethylsiloxy)methyl>phosphine oxide (63245-88-5) → chloro-trimethyl-silane (75-77-4) + tris(chloromethyl)phosphine oxide (4851-89-2)

Guidance literature:

With phosphorus pentachloride; In benzene; at 0 ℃;

Reference yield: 96.5%

tris<(trimethylsiloxy)methyl>phosphine (63245-87-4) → chloro-trimethyl-silane (75-77-4) + tris(chloromethyl)phosphine oxide (4851-89-2)

Guidance literature:

With phosphorus pentachloride; In benzene; at 0 ℃;

Reference yield: 82.0%

tris(acetoxymethyl)phosphine oxide (4851-97-2) → tris(chloromethyl)phosphine oxide (4851-89-2) + acetic acid (64-19-7,77671-22-8)

Guidance literature:

With hydrogenchloride; at 180 - 200 ℃; for 5h;

DOI:10.1007/BF00949641

upstream raw materials:

tris(acetoxymethyl)phosphine oxide

tris<(trimethylsiloxy)methyl>phosphine

tris<(trimethylsiloxy)methyl>phosphine oxide

Downstream raw materials:

Tris-benzoyloxymethyl-phosphinoxid

Tris-(diphenyloxophosphinomethyl)-phosphinoxid

Tris-(O-n-butyl-phenylphosphinylmethyl)-phosphinoxid

Tri-phenoxymethyl-phosphinoxid

Refernces

Bowl-shaped C(3)-symmetric receptor with concave phosphine oxide with a remarkable selectivity for asparagine derivatives.

10.1021/ol034168b

The research focuses on the development of a bowl-shaped C3-symmetric receptor (1a) with a concave phosphine oxide functionality within its molecular bowl, designed to exhibit remarkable selectivity for asparagine (Asn) derivatives. The purpose of this study was to construct a host molecule with a rigidly defined cavity that could mimic the active site of enzymes, thereby functioning as a reaction or binding site with unique properties. The researchers synthesized 1a and 1b, starting with the trialkylation of tris(chloromethyl)phosphine oxide with dimethyl 5-mercaptoisophthalate, followed by an intermolecular macrolactamization process. The conclusions drawn from the study indicate that 1a showed a high residue selectivity for Asn alkyl amide against other amino acid derivatives like Gln, Glu, and Asp, which have similar H-bond donor/acceptor geometries. This selectivity was attributed to the cooperative hydrogen bonding between the phosphine oxide in the cavity of 1a and the guest molecules, along with subtle differences in the intermolecular hydrogen bonding mode within the cavity. The chemicals used in the synthesis process included tris(chloromethyl)phosphine oxide, dimethyl 5-mercaptoisophthalate, and (1R,2R)-diaminocyclohexane, among others.