Allyl tetraisopropylphosphorodiamidite

Base Information

• Chemical Name: Allyl tetraisopropylphosphorodiamidite
• CAS No.: 108554-72-9
• Molecular Formula: C15H33N2OP
• Molecular Weight: 288.414
• Hs Code.: 2931499090
• DSSTox Substance ID: DTXSID80399404
• Nikkaji Number: J1.461.982H
• Wikidata: Q82201945
• Mol file: 108554-72-9.mol

Synonyms:108554-72-9;ALLYL TETRAISOPROPYLPHOSPHORODIAMIDITE;1-(Allyloxy)-N,N,N',N'-tetraisopropylphosphinediamine;N-[[di(propan-2-yl)amino]-prop-2-enoxyphosphanyl]-N-propan-2-ylpropan-2-amine;Phosphorodiamidousacid, N,N,N',N'-tetrakis(1-methylethyl)-, 2-propen-1-yl ester;SCHEMBL1456272;DTXSID80399404;Allyl tetraisopropylphosphorodiamidite, 95%;CS-0459910;FT-0651136;3-[Bis(diisopropylamino)phosphinooxy]-1-propene;A909107;Phosphorodiamidousacid,N,N,N',N'-tetrakis(1-methylethyl)-,2-propen-1-yl ester

Chemical Property of Allyl tetraisopropylphosphorodiamidite

Chemical Property:

• Vapor Pressure: 0.000375mmHg at 25°C
• Refractive Index: n20/D 1.466(lit.)
• Boiling Point: 317.8 °C at 760 mmHg
• PKA: 7.71±0.70(Predicted)
• Flash Point: 146 °C
• PSA: 29.30000
• Density: 0.903 g/mL at 25 °C(lit.)
• LogP: 4.65350
• Storage Temp.: 2-8°C
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 9
• Exact Mass: 288.23305068
• Heavy Atom Count: 19
• Complexity: 219

Purity/Quality:

98%,99%, ^*data from raw suppliers

Allyl tetraisopropylphosphorodiamidite 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)N(C(C)C)P(N(C(C)C)C(C)C)OCC=C
• Uses: Allyl tetraisopropylphosphorodiamidite may be used in the total synthesis of (?)-tetrahydrolipstatin, dolabelide C, (-)-salicylihalamides A and B.

Technology Process of Allyl tetraisopropylphosphorodiamidite

There total 4 articles about Allyl tetraisopropylphosphorodiamidite 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: 52.0%

2-propenyloxydichlorophosphine (41003-33-2) + diisopropylamine (108-18-9) → (allyloxy)bis(diisopropylamino)phosphine (108554-72-9)

Guidance literature:

In diethyl ether; at 25 ℃; for 20h;

DOI:10.1021/ja00161a006

Reference yield:

Chlorphosphan (82614-82-2) + allyl alcohol (107-18-6) → (allyloxy)bis(diisopropylamino)phosphine (108554-72-9)

Guidance literature:

With phosphorus trichloride; In acetonitrile; at -20 - 20 ℃; for 20h;

DOI:10.1016/j.bmc.2012.07.047

Reference yield:

diisopropylamine (108-18-9) + allyl alcohol (107-18-6) → (allyloxy)bis(diisopropylamino)phosphine (108554-72-9)

Guidance literature:

With pyridine; phosphorus trichloride; Yield given. Multistep reaction; 1.) one equivalent 2-propen-1-ol, -78 deg C, 90 min, diethyl ether 2.) -10 deg C, 60 min;

DOI:10.1016/S0040-4039(01)80694-8

upstream raw materials:

2-propenyloxydichlorophosphine

diisopropylamine

allyl alcohol

Chlorphosphan

Downstream raw materials:

(3-{(2R,4S,5R)-4-(Allyloxy-diisopropylamino-phosphanyloxy)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-2-yl}-3H-purin-6-yl)-carbamic acid allyl ester

N⁶-[(allyloxy)carbonyl]-2'-O-(tert-butyldimethylsilyl)-5'-O-(p,p'-dimethoxytrityl)adenosine 3'-(allyl N,N'-diisopropylphosphoramidite)

N⁴-(allyloxycarbonyl)-3'-O-(p,p'-dimethoxytrityl)-2'-deoxyacytidine 5'-(allyl N,N-diisopropylphosphoramidite)

N⁶-(allyloxycarbonyl)-3'-O-(p,p'-dimethoxytrityl)-2'-deoxyadenosine 5'-(allyl N,N-diisopropylphosphoramidite)

Refernces

• 1、 Chen, Jian,Prestwich, Glenn D.. "Regioselective synthesis of photolabile P(1,2)- and P(4,5)-(o-nitrobenzyl) esters of myo-inositol 1,2,3,4,5,6-hexakisphosphate". . p. 969 - 972. Retrieved 2007/10/03.
• 2、 Hayakawa,Wakabayashi,Kato,Noyori. "The allylic protection method in solid-phase oligonucleotide synthesis. An efficient preparation of solid-anchored DNA oligomers". . p. 1691 - 1696. Retrieved 2007/10/02.