Diethyl (trichloromethyl)phosphonate

Base Information

• Chemical Name: Diethyl (trichloromethyl)phosphonate
• CAS No.: 866-23-9
• Molecular Formula: C5H10 Cl3 O3 P
• Molecular Weight: 255.465
• Hs Code.: 29319000
• European Community (EC) Number: 622-785-4
• NSC Number: 46567
• DSSTox Substance ID: DTXSID50235688
• Nikkaji Number: J7.147A
• Wikidata: Q83117575
• Mol file: 866-23-9.mol

Synonyms:866-23-9;Diethyl (trichloromethyl)phosphonate;Diethyl trichloromethylphosphonate;Diethyltrichloromethylphosphonate;1-[ethoxy(trichloromethyl)phosphoryl]oxyethane;Ro 3-0658;Phosphonic acid, trichloromethyl-, diethyl ester;NSC 46567;Phosphonic acid, (trichloromethyl)-, diethyl ester;BRN 1210640;AI3-18556;Methanephosphonic acid, trichloro-, diethyl ester;4-03-00-00262 (Beilstein Handbook Reference);C5H10Cl3O3P;WLN: GXGGPO&O2&O2;SCHEMBL3131911;INGENOL3,20-DIBENZOATE;C5-H10-Cl3-O3-P;DTXSID50235688;NSC46567;MFCD00013666;NSC-46567;Trichloromethylphosphonic acid diethyl;AKOS015848630;AS-64095;Diethyl (trichloromethyl)phosphonate, 97%;LS-106808;trichloromethanephosphonic acid diethyl ester;CS-0151420;D4607;FT-0624864;trichloromethyl-phosphonic acid diethyl ester;(Trichloromethyl)phosphonic Acid Diethyl Ester;D90306;EN300-7867510;Diethyl (trichloromethyl)phosphonate, purum, >=97.0% (GC)

Chemical Property of Diethyl (trichloromethyl)phosphonate

Chemical Property:

• Vapor Pressure: 0.0204mmHg at 25°C
• Refractive Index: n20/D 1.463(lit.)
• Boiling Point: 130-131 °C14 mm Hg(lit.)
• Flash Point: >230 °F
• PSA: 45.34000
• Density: 1.362 g/mL at 25 °C(lit.)
• LogP: 3.58020
• Storage Temp.: 2-8°C
• Water Solubility.: 4.5g/L(25 oC)
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 253.943314
• Heavy Atom Count: 12
• Complexity: 169

Purity/Quality:

99.0% ^*data from raw suppliers

Diethyl (Trichloromethyl)phosphonate ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38-22
• Safety Statements: 26-36-60-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOP(=O)(C(Cl)(Cl)Cl)OCC
• Uses: Diethyl (trichloromethyl)phosphonate may be used in the synthesis of chlorovinyl phosphonates via reaction with aldehydes and ketones.

Technology Process of Diethyl (trichloromethyl)phosphonate

There total 7 articles about Diethyl (trichloromethyl)phosphonate 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: 70.0%

diethylamine (109-89-7) + triethyl phosphite (122-52-1) → diethyl (trichloromethyl)phosphonate (866-23-9) + triethyl phosphate (78-40-0) + diethyl-amidophosphoric acid diethyl ester (3167-69-9) + C3H5Cl3O3P(1-) (44864-93-9)

Guidance literature:

With tetrachloromethane; trimethylamine hydrochloride; In acetonitrile; at 45 - 50 ℃; for 3h; Yields of byproduct given;

Reference yield: 46.0%

tetrachloromethane (56-23-5) + 1-adamantyl diethyl phosphite (77075-13-9) → diethyl (trichloromethyl)phosphonate (866-23-9) + 1-chloroadamantane (935-56-8) + 1-adamantyl ethyl (trichloromethyl)phosphonate (91453-40-6) + 1-adamantyl ethyl phosphorochloridate

Guidance literature:

for 3h; Heating;

Reference yield: 19.7%

tetrachloromethane (56-23-5) + diethyl trimethylsilyl phosphite (13716-45-5) → 1,1,3,3-tetramethyl-1,3-disiletane (1627-98-1) + chloro-trimethyl-silane (75-77-4) + diethyl (trichloromethyl)phosphonate (866-23-9) + chloroform (67-66-3,8013-54-5) + diethyl chlorophosphate (814-49-3)

Guidance literature:

at 45 - 55 ℃; for 3h; Product distribution;

DOI:10.1007/BF00959203

upstream raw materials:

tetrachloromethane

diphosphorous acid tetraethyl ester

1-adamantyl diethyl phosphite

diethylamine

Downstream raw materials:

(trichloromethyl)phosphonic acid

phenyl-hydrazine; salt of trichloromethyl-phosphonic acid monoethyl ester

1,1-dichloro-2,2-diphenylethene

(Z)-2-chloro-4,4-dimethyl-1-phenylpent-1-en-3-one

Refernces

• 1、 Le Menn, J.C.,Sarrazin, J.. "Qualitative investigation of the Wittig-Horner reaction by means of electrogenerated bases". . p. 781 - 786. Retrieved 2007/10/02.
• 2、 Yurchenko, R. I.,Klepa, T. I.. "QUESTION OF THE OUTGOING GROUP IN THE ARBUZOV REACTION OF 1-ADAMANTYL DIETHYL PHOSPHITE". . p. 632 - 633. Retrieved 2007/10/02.