654636-62-1

Basic information

• Product Name: 3,7-Dioxa-4-aza-6-phosphanonanoic acid, 4,5-bis(1,1-dimethylethyl)-6-ethoxy-2,2-dimethyl-, 6-oxide
• Synonyms: 2-([tert-butyl[1-(diethoxyphosphoryl)-2,2-dimethylpropyl]amino]oxy)-2-methylpropionic acid;BlocBuilder MA;BlocBuilder.(R).;2-({tert-butyl[1-(diethoxyphosphoryl)-2,2-dimethylpropyl]amino}oxy)-2-methylpropionic acid;MAMA-SG1;N-(2-methylpropyl)-N-(1-diethylphosphono-2,2-dimethylpropyl)-O-(2-carboxyprop-2-yl)hydroxylamine
• CAS NO: 654636-62-1
• Molecular Formula: C17H36NO6P
• Molecular Weight: 381.45
• Mol File: 654636-62-1.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 3,7-Dioxa-4-aza-6-phosphanonanoic acid, 4,5-bis(1,1-dimethylethyl)-6-ethoxy-2,2-dimethyl-, 6-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: 3,7-Dioxa-4-aza-6-phosphanonanoic acid, 4,5-bis(1,1-dimethylethyl)-6-ethoxy-2,2-dimethyl-, 6-oxide(654636-62-1)
• EPA Substance Registry System: 3,7-Dioxa-4-aza-6-phosphanonanoic acid, 4,5-bis(1,1-dimethylethyl)-6-ethoxy-2,2-dimethyl-, 6-oxide(654636-62-1)

Safety Data

• Hazardous Substances Data: 654636-62-1(Hazardous Substances Data)

Usage

General Description

3,7-Dioxa-4-aza-6-phosphanonanoic acid, 4,5-bis(1,1-dimethylethyl)-6-ethoxy-2,2-dimethyl-, 6-oxide is a chemical compound with multiple functional groups. It contains a phosphorus atom, a nitrogen atom, and two oxygen atoms in its structure. The compound also has tert-butyl and ethoxy groups, as well as a dimethyl group. It is likely to be a complex and potentially versatile compound with the ability to interact with a variety of other molecules and functional groups, potentially making it suitable for use in diverse chemical reactions or applications.

Synthetic route

N,N-diethyl-S-(α,α-dimethyl-α-acetic acid)dithiocarbamate (548761-51-9) + N-(2-methyl-2-propyl)-N-(1-diethylphosphono-2,2-dimethylpropyl)aminoxyl (188526-94-5) → N-(2-methyl-2-propyl)-N-(1-diethylphosphono-2,2-dimethylpropyl)-O-(2-carboxyprop-2-yl)hydroxylamide (654636-62-1)

Conditions	Yield
In ethanol at 10℃; for 4.5h; UV-irradiation;	95%

2,2'-azobis(isobutyric acid) disodium salt + N-(2-methyl-2-propyl)-N-(1-diethylphosphono-2,2-dimethylpropyl)aminoxyl (188526-94-5) → N-(2-methyl-2-propyl)-N-(1-diethylphosphono-2,2-dimethylpropyl)-O-(2-carboxyprop-2-yl)hydroxylamide (654636-62-1)

Conditions	Yield
In methanol; water at 10℃; for 4.5h; UV-irradiation;	93%

N,N-diethyl-S-(α,α-dimethyl-α-acetic acid)dithiocarbamate (548761-51-9) + N-(2-methyl-2-propyl)-N-(1-diethylphosphono-2,2-dimethylpropyl)aminoxyl (188526-94-5) → disulfiram (97-77-8) + N-(2-methyl-2-propyl)-N-(1-diethylphosphono-2,2-dimethylpropyl)-O-(2-carboxyprop-2-yl)hydroxylamide (654636-62-1)

Conditions	Yield
In ethanol at 20℃; for 4h; Product distribution / selectivity; Inert atmosphere; Photolysis;	A n/a B 90%

2-bromo-2-methylpropionic acid (2052-01-9) + N-(2-methyl-2-propyl)-N-(1-diethylphosphono-2,2-dimethylpropyl)aminoxyl (188526-94-5) → N-(2-methyl-2-propyl)-N-(1-diethylphosphono-2,2-dimethylpropyl)-O-(2-carboxyprop-2-yl)hydroxylamide (654636-62-1)

Conditions	Yield
Stage #1: 2-bromo-2-methylpropionic acid; N-(2-methyl-2-propyl)-N-(1-diethylphosphono-2,2-dimethylpropyl)aminoxyl With N,N,N',N'',N'''-pentamethyldiethylenetriamine; copper; copper(I) bromide In methanol at 20℃; for 4h; Inert atmosphere; Stage #2: With hydrogenchloride In methanol; water at 12℃; pH=1.5; Product distribution / selectivity;	86%
With N,N,N',N'',N'''-pentamethyldiethylenetriamine; copper; copper(I) bromide In benzene at 20℃; for 3h;	75%
With N,N,N',N'',N'''-pentamethyldiethylenetriamine; copper; copper(I) bromide In toluene at 20℃; for 1.5h;	60%

2-methyl-2-[N-(diethoxyphosphoryl-2,2-dimethylpropyl)aminoxy]propionic acid, sodium salt + water (7732-18-5) → N-(2-methyl-2-propyl)-N-(1-diethylphosphono-2,2-dimethylpropyl)-O-(2-carboxyprop-2-yl)hydroxylamide (654636-62-1)

Conditions	Yield
With hydrogenchloride In methanol; water

N-(2-methyl-2-propyl)-N-(1-diethylphosphono-2,2-dimethylpropyl)-O-(2-carboxyprop-2-yl)hydroxylamide (654636-62-1) → C24H43N2O6P

Conditions	Yield
In tetrahydrofuran at 100℃; for 1h; Schlenk technique; Inert atmosphere;	85%

ethyl iodide (75-03-6) + N-(2-methyl-2-propyl)-N-(1-diethylphosphono-2,2-dimethylpropyl)-O-(2-carboxyprop-2-yl)hydroxylamide (654636-62-1) → ethyl 2-((tert-butyl(1-(diethoxyphosphoryl)-2,2-dimethylpropyl)amino)oxy)-2-methylpropanoate (1034132-98-3)

Conditions	Yield
Stage #1: N-(2-methyl-2-propyl)-N-(1-diethylphosphono-2,2-dimethylpropyl)-O-(2-carboxyprop-2-yl)hydroxylamide With 1,8-diazabicyclo[5.4.0]undec-7-ene In benzene Inert atmosphere; Stage #2: ethyl iodide In benzene at 20℃; for 24h; Inert atmosphere;	78%

methyl iodide (74-88-4) + N-(2-methyl-2-propyl)-N-(1-diethylphosphono-2,2-dimethylpropyl)-O-(2-carboxyprop-2-yl)hydroxylamide (654636-62-1) → methyl 2-methyl-2-[N-tert-butyl-N-(1-diethoxyphosphoryl-2,2-dimethylpropyl)aminoxy]propionate

Conditions	Yield
Stage #1: N-(2-methyl-2-propyl)-N-(1-diethylphosphono-2,2-dimethylpropyl)-O-(2-carboxyprop-2-yl)hydroxylamide With 1,8-diazabicyclo[5.4.0]undec-7-ene In benzene Inert atmosphere; Stage #2: methyl iodide In benzene at 20℃; for 24h; Inert atmosphere;	77%

2-propenoic acid 1,2 ethanediylbis(oxy-2,1-ethanediyl) ester (1680-21-3) + N-(2-methyl-2-propyl)-N-(1-diethylphosphono-2,2-dimethylpropyl)-O-(2-carboxyprop-2-yl)hydroxylamide (654636-62-1) → C46H90O18N2P2 (871982-25-1)

Conditions	Yield
In tert-butyl alcohol at 100℃; for 1h;	70%

acrylic acid n-butyl ester (141-32-2) + N-(2-methyl-2-propyl)-N-(1-diethylphosphono-2,2-dimethylpropyl)-O-(2-carboxyprop-2-yl)hydroxylamide (654636-62-1) → 2,2-dimethyl-4-[N-tert-butyl-N-(1-diethoxyphosphoryl-2,2-dimethylpropyl)aminoxy]-4-n-butoxycarbonylbutanoic acid

Conditions	Yield
In tert-butyl alcohol at 80℃; for 6h;	65%
In tert-butyl alcohol at 100℃; for 1.25h; Inert atmosphere;	45%

N-(2-methyl-2-propyl)-N-(1-diethylphosphono-2,2-dimethylpropyl)-O-(2-carboxyprop-2-yl)hydroxylamide (654636-62-1) + 2-{[(4-bromo-benzenesulfonyl)-phenyl-amino]-methyl}-acrylic acid ethyl ester (647018-77-7) → 1-(4-bromo-benzenesulfonyl)-3-(2-carboxy-2-methyl-propyl)-2,3-dihydro-1H-indole-3-carboxylic acid ethyl ester

Conditions	Yield
In tert-butyl alcohol at 70℃; for 12h;	62%

N-(4-benzoylphenyl)acrylamide (22421-62-1) + N-(2-methyl-2-propyl)-N-(1-diethylphosphono-2,2-dimethylpropyl)-O-(2-carboxyprop-2-yl)hydroxylamide (654636-62-1) → C33H49N2O8P (1304668-93-6)

Conditions	Yield
In tetrahydrofuran at 100℃; for 1h; Inert atmosphere;	60%

N-(2-methyl-2-propyl)-N-(1-diethylphosphono-2,2-dimethylpropyl)-O-(2-carboxyprop-2-yl)hydroxylamide (654636-62-1) + 2-{[tert-butoxycarbonyl-(4-nitro-phenyl)-amino]-methyl}-acrylic acid ethyl ester → 3-(2-carboxy-2-methyl-propyl)-5-nitro-2,3-dihydro-indole-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester

Conditions	Yield
In tert-butyl alcohol at 70℃; for 12h;	58%

allyl bromide (106-95-6) + N-(2-methyl-2-propyl)-N-(1-diethylphosphono-2,2-dimethylpropyl)-O-(2-carboxyprop-2-yl)hydroxylamide (654636-62-1) → allyl 2-((tert-butyl(1-(diethoxyphosphoryl)-2,2-dimethylpropyl)amino)oxy)-2-methylpropanoate (1393670-68-2)

Conditions	Yield
Stage #1: N-(2-methyl-2-propyl)-N-(1-diethylphosphono-2,2-dimethylpropyl)-O-(2-carboxyprop-2-yl)hydroxylamide With 1,8-diazabicyclo[5.4.0]undec-7-ene In benzene Inert atmosphere; Stage #2: allyl bromide In benzene at 20℃; for 24h; Inert atmosphere;	57%

4-acryloylbenzophenone + N-(2-methyl-2-propyl)-N-(1-diethylphosphono-2,2-dimethylpropyl)-O-(2-carboxyprop-2-yl)hydroxylamide (654636-62-1) → C33H48NO9P (1304668-94-7)

Conditions	Yield
In tetrahydrofuran at 100℃; for 1h; Inert atmosphere;	55%

N-(2-methyl-2-propyl)-N-(1-diethylphosphono-2,2-dimethylpropyl)-O-(2-carboxyprop-2-yl)hydroxylamide (654636-62-1) + 2-{[(4-bromo-benzenesulfonyl)-(4-methoxy-phenyl)-amino]-methyl}-acrylic acid ethyl ester (647018-78-8) → 1-(4-bromo-benzenesulfonyl)-3-(2-carboxy-2-methyl-propyl)-5-methoxy-2,3-dihydro-1H-indole-3-carboxylic acid ethyl ester

Conditions	Yield
In tert-butyl alcohol at 70℃; for 18h;	54%

2-{[tert-butoxycarbonyl-(4-methoxy-phenyl)-amino]-methyl}-acrylic acid ethyl ester (647018-76-6) + N-(2-methyl-2-propyl)-N-(1-diethylphosphono-2,2-dimethylpropyl)-O-(2-carboxyprop-2-yl)hydroxylamide (654636-62-1) → 3-(2-carboxy-2-methyl-propyl)-5-methoxy-2,3-dihydro-indole-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester

Conditions	Yield
In tert-butyl alcohol at 70℃; for 18h;	48%

2-[(methyl-phenyl-amino)-methyl]-acrylic acid ethyl ester (647018-73-3) + N-(2-methyl-2-propyl)-N-(1-diethylphosphono-2,2-dimethylpropyl)-O-(2-carboxyprop-2-yl)hydroxylamide (654636-62-1) → 3-(2-carboxy-2-methyl-propyl)-1-methyl-2,3-dihydro-1H-indole-3-carboxylic acid ethyl ester

Conditions	Yield
In tert-butyl alcohol at 70℃; for 12h;	47%

2-[(tert-butoxycarbonyl-phenyl-amino)-methyl]-acrylic acid ethyl ester (647018-75-5) + N-(2-methyl-2-propyl)-N-(1-diethylphosphono-2,2-dimethylpropyl)-O-(2-carboxyprop-2-yl)hydroxylamide (654636-62-1) → 3-(2-carboxy-2-methyl-propyl)-2,3-dihydro-indole-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester

Conditions	Yield
In tert-butyl alcohol at 70℃; for 12h;	45%

glycinamide hydrochloride (1668-10-6) + N-(2-methyl-2-propyl)-N-(1-diethylphosphono-2,2-dimethylpropyl)-O-(2-carboxyprop-2-yl)hydroxylamide (654636-62-1) → C19H40N3O6P (1228178-48-0)

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 1.5h; Inert atmosphere;	45%

2-{[(4-methoxy-phenyl)-methyl-amino]-methyl}-acrylic acid ethyl ester (647018-74-4) + N-(2-methyl-2-propyl)-N-(1-diethylphosphono-2,2-dimethylpropyl)-O-(2-carboxyprop-2-yl)hydroxylamide (654636-62-1) → 3-(2-carboxy-2-methyl-propyl)-5-methoxy-1-methyl-2,3-dihydro-1H-indole-3-carboxylic acid ethyl ester

Conditions	Yield
In tert-butyl alcohol at 70℃; for 12h;	38%

C52H83N12O13Pol + C9H14N4O4 (1563177-07-0) + N-(2-methyl-2-propyl)-N-(1-diethylphosphono-2,2-dimethylpropyl)-O-(2-carboxyprop-2-yl)hydroxylamide (654636-62-1) → C64H108N17O18P (1563177-09-2)

Conditions

Yield

Stage #1: C52H83N12O13Pol; N-(2-methyl-2-propyl)-N-(1-diethylphosphono-2,2-dimethylpropyl)-O-(2-carboxyprop-2-yl)hydroxylamide With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one fluorenylmethoxycarbonyl (Fmoc) amide resin; Stage #2: C9H14N4O4 In N,N-dimethyl-formamide at 20 - 70℃; for 72.5h; fluorenylmethoxycarbonyl (Fmoc) amide resin; Inert atmosphere; Stage #3: With trifluoroacetic acid In water for 1.83333h; fluorenylmethoxycarbonyl (Fmoc) amide resin;

35%

C52H83N12O13Pol + C21H37N9O7 (1563177-08-1) + N-(2-methyl-2-propyl)-N-(1-diethylphosphono-2,2-dimethylpropyl)-O-(2-carboxyprop-2-yl)hydroxylamide (654636-62-1) → C76H131N22O21P (1563177-10-5)

Conditions

Yield

Stage #1: C52H83N12O13Pol; N-(2-methyl-2-propyl)-N-(1-diethylphosphono-2,2-dimethylpropyl)-O-(2-carboxyprop-2-yl)hydroxylamide With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one fluorenylmethoxycarbonyl (Fmoc) amide resin; Stage #2: C21H37N9O7 In N,N-dimethyl-formamide at 20 - 70℃; fluorenylmethoxycarbonyl (Fmoc) amide resin; Inert atmosphere; Stage #3: With trifluoroacetic acid In water for 1.83333h; fluorenylmethoxycarbonyl (Fmoc) amide resin; chemoselective reaction;

30%

C52H83N12O13Pol + C15H26N6O5 + N-(2-methyl-2-propyl)-N-(1-diethylphosphono-2,2-dimethylpropyl)-O-(2-carboxyprop-2-yl)hydroxylamide (654636-62-1) → C70H120N19O19P (1563177-12-7)

Conditions

Yield

Stage #1: C52H83N12O13Pol; N-(2-methyl-2-propyl)-N-(1-diethylphosphono-2,2-dimethylpropyl)-O-(2-carboxyprop-2-yl)hydroxylamide With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one fluorenylmethoxycarbonyl (Fmoc) amide resin; Stage #2: C15H26N6O5 In N,N-dimethyl-formamide at 20 - 70℃; fluorenylmethoxycarbonyl (Fmoc) amide resin; Inert atmosphere; Stage #3: With trifluoroacetic acid In water for 1.83333h; fluorenylmethoxycarbonyl (Fmoc) amide resin; Temperature; Time;

15%

10-Undecen-1-ol (112-43-6) + N-(2-methyl-2-propyl)-N-(1-diethylphosphono-2,2-dimethylpropyl)-O-(2-carboxyprop-2-yl)hydroxylamide (654636-62-1) → undec-10-en-1-yl 2-((tert-butyl(1-(diethoxyphosphoryl)-2,2-dimethylpropyl)amino)oxy)-2-methylpropanoate (1393670-66-0)

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0℃; Mitsunobu reaction;	11%

N-(2-methyl-2-propyl)-N-(1-diethylphosphono-2,2-dimethylpropyl)-O-(2-carboxyprop-2-yl)hydroxylamide (654636-62-1) → N-(2-methyl-2-propyl)-N-(1-diethylphosphono-2,2-dimethylpropyl)aminoxyl (188526-94-5)

Conditions	Yield
With oxygen at 120℃; Kinetics;

N-(2-methyl-2-propyl)-N-(1-diethylphosphono-2,2-dimethylpropyl)-O-(2-carboxyprop-2-yl)hydroxylamide (654636-62-1) → C17H35ClNO5P

Conditions	Yield
With thionyl chloride In dichloromethane at 20℃; for 2h;

sodium 4-styrenesulfonate (2695-37-6) + N-(2-methyl-2-propyl)-N-(1-diethylphosphono-2,2-dimethylpropyl)-O-(2-carboxyprop-2-yl)hydroxylamide (654636-62-1) → C25H43NO9PS(1-)*Na(1+) (947705-50-2)

Conditions	Yield
In ethanol; water at 70℃; for 6h; Inert atmosphere;

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + N-(2-methyl-2-propyl)-N-(1-diethylphosphono-2,2-dimethylpropyl)-O-(2-carboxyprop-2-yl)hydroxylamide (654636-62-1) → 2-methyl-2-[N-tert-butyl-N-(1-diethoxyphosphoryl-2,2-dimethylpropyl)aminoxy]-N-propionyloxysuccinimide (1068449-32-0)

Conditions	Yield
With dicyclohexyl-carbodiimide In tetrahydrofuran at 0℃; for 1.5h;
With dicyclohexyl-carbodiimide In tetrahydrofuran at 5℃;

Upstream product

• 2052-01-9 2-bromo-2-methylpropionic acid 
• 188526-94-5 N-(2-methyl-2-propyl)-N-(1-diethylphosphono-2,2-dimethylpropyl)aminoxyl 
• 548761-51-9 N,N-diethyl-S-(α,α-dimethyl-α-acetic acid)dithiocarbamate 
• 7732-18-5 water 

Downstream Products

• 947705-50-2 C₂₅H₄₃NO₉PS^(1-)*Na⁽¹⁺⁾ 
• 762-04-9 Diethyl phosphonate 
• 79-31-2 isobutyric Acid 
• 227000-10-4 diethyl 2,2-dimethyl-1-(1,1-dimethylethylamino)propylphosphonate 
• 1304668-93-6 C₃₃H₄₉N₂O₈P 
• 1304668-94-7 C₃₃H₄₈NO₉P 

Relevant articles and documents

Polar, steric, and stabilization effects in alkoxyamines C-ON bond homolysis: A multiparameter analysis

We present measurements of the rate constants (kd) of the C-ON bond cleavage in new alkoxyamine models containing the N-(2-methyl-2-propyl)-N-diethylphosphono-2,2-dimethylpropyl)-N-oxyl (SG1) moiety. The homolysis rate constants of 2,2,6,6-tetramethylpiperidinyl-1-oxyl (TEMPO)-and SG1-based alkoxyamines are analyzed in terms of polar inductive/field (σU), steric (σv), and radical stabilization (σRS) contributions of the leaving alkyl radicals, using a multiparameter equation, i.e., log(kd/k d,0) = ρUσU + δv + ρ RSσRS. The rate constants increase with increasing electron withdrawing, steric, and stabilization demands of the leaving alkyl radicals. Good correlations are found for TEMPO (log(kd/k d,0) = 13.6σU + 6.6v + 13.9σRS) and SG1 (log(kd/kd,0) = 19.5σU + 7.0v + 15.3σRS) derivatives, highlighting the polar sensitivity of the leaving alkyl radical to the nitroxyl moiety. Such correlations should facilitate the design of new alkoxyamines as initiators/regulators and help to improve the tuning of NMP experiments.

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