O-(3-Butenyl)-N,N-bis(2-chloroethyl)phosphorodiamidate

Base Information

• Chemical Name: O-(3-Butenyl)-N,N-bis(2-chloroethyl)phosphorodiamidate
• CAS No.: 39800-29-8
• Molecular Formula: C8H17 Cl2 N2 O2 P
• Molecular Weight: 275.115
• Mol file: 39800-29-8.mol

Synonyms:Phosphorodiamidic acid, N,N-bis(2-chloroethyl)-,3-butenyl ester (9CI); 3-Butenyl N,N-bis(2-chloroethyl)phosphorodiamidate; NSC 154039; O-(3-Butenyl)-N,N-bis(2-chloroethyl)phosphorodiamidate

Chemical Property of O-(3-Butenyl)-N,N-bis(2-chloroethyl)phosphorodiamidate

Chemical Property:

• Vapor Pressure: 2.97E-05mmHg at 25°C
• Boiling Point: 356.2°Cat760mmHg
• Flash Point: 169.2°C
• PSA: 65.37000
• Density: 1.251g/cm³
• LogP: 3.12580
• Solubility.: Chloroform (Slightly), Methanol (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

O-(3-Butenyl)-N,N-bis(2-chloroethyl)phosphorodiamidate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: An antitumor agent

Technology Process of O-(3-Butenyl)-N,N-bis(2-chloroethyl)phosphorodiamidate

There total 3 articles about O-(3-Butenyl)-N,N-bis(2-chloroethyl)phosphorodiamidate 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:

O-(3-Butenyl)-N,N-bis(2-chlorethyl)-phosphoramidoylchlorid (64968-62-3) → O-3-buten-1-yl N,N-bis(2-chloroethyl)phosphorodiamidate (39800-29-8)

Guidance literature:

With ammonia; In tetrahydrofuran; for 2h; Yield given; Ambient temperature;

DOI:10.1021/jm00114a014

Reference yield:

homoalylic alcohol (627-27-0) + bis-(2-chloroethyl)amine hydrochloride (821-48-7) → O-3-buten-1-yl N,N-bis(2-chloroethyl)phosphorodiamidate (39800-29-8)

Guidance literature:

Multistep reaction; (i) POCl₃, CH₂Cl₂, (ii) /BRN= 3550356/, Et₃N, (iii) NH₃;

DOI:10.1021/ja00784a092 DOI:10.1021/jm00238a011

Reference yield:

N,N-di(2-chloroethyl)amidophosphoric acid dichloride (127-88-8) + homoalylic alcohol (627-27-0) → O-3-buten-1-yl N,N-bis(2-chloroethyl)phosphorodiamidate (39800-29-8)

Guidance literature:

With n-butyllithium; ammonia; Yield given. Multistep reaction;

DOI:10.1021/jm00370a008

upstream raw materials:

homoalylic alcohol

bis-(2-chloroethyl)amine hydrochloride

N,N-di(2-chloroethyl)amidophosphoric acid dichloride

O-(3-Butenyl)-N,N-bis(2-chlorethyl)-phosphoramidoylchlorid

Downstream raw materials:

trans-4-hydroperoxycyclophosphamide

cis-4-hydroxycyclophosphamide

4-(S-ethanol)-sulfido-cyclophosphamide

C₁₃H₂₇Cl₂N₂O₅P

Refernces

• 1、 Borch,Hoye,Swanson. "In situ preparation and fate of cis-4-hydroxycyclophosphamide and aldophosphamide: 1H and 31P NMR evidence for equilibration of cis- and trans-4-hydroxycyclophosphamide with aldophosphamide and its hydrate in aqueous solution". . p. 490 - 494. Retrieved 2007/10/02.