14384-45-3

Basic information

• Product Name: N,N'-DIHYDROXY-2,3-DIMETHYL-2,3-BUTANEDIAMINE
• Synonyms: N,N'-DIHYDROXY-2,3-DIMETHYL-2,3-BUTANEDIAMINE;2,3-Bis(hydroxyamino)-2,3-dimethylbutane;2,3-Dimethyl-2,3-bis(hydroxyamino)butane;N,N'-(1,1,2,2-Tetramethylethylene)bis(hydroxylamine);N,N'-(2,3-Dimethylbutane-2,3-diyl)di(hydroxylamine);N,N'-Dihydroxy-2,3-dimethylbutane-2,3-diamine;N-[3-(hydroxyamino)-2,3-dimethylbutan-2-yl]hydroxylamine
• CAS NO: 14384-45-3
• Molecular Formula: C₆H₁₆N₂O₂
• Molecular Weight: 148.2
• Product Categories: pharmacetical
• Mol File: 14384-45-3.mol
• Article Data: 34

Chemical Properties

• Melting Point: 157-159 °C
• Boiling Point: 274.6 °C at 760 mmHg
• Flash Point: 123.1 °C
• Appearance: /
• Density: 1.056
• PKA: 14.04±0.50(Predicted)
• CAS DataBase Reference: N,N'-DIHYDROXY-2,3-DIMETHYL-2,3-BUTANEDIAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: N,N'-DIHYDROXY-2,3-DIMETHYL-2,3-BUTANEDIAMINE(14384-45-3)
• EPA Substance Registry System: N,N'-DIHYDROXY-2,3-DIMETHYL-2,3-BUTANEDIAMINE(14384-45-3)

Safety Data

• Hazardous Substances Data: 14384-45-3(Hazardous Substances Data)

Usage

Uses

N,N''-Dihydroxy-2,3-dimethyl-2,3-butanediamine is a reactant in the preparation of pthalocyanine derivatives as well as heterospin complexes.

Synthetic route

2,3-bis(hydroxyamino)-2,3-dimethylbutane monosulfate (14538-51-3, 78375-92-5) → N,N'-dihydroxy-2,3-dimethylbutane-2,3-diamine (14384-45-3)

Conditions	Yield
With sodium hydroxide In methanol for 2h; Cooling with ice; Inert atmosphere;	79.1%

2,3-dimethyl-2,3-dinitrobutane (3964-18-9) → N,N'-dihydroxy-2,3-dimethylbutane-2,3-diamine (14384-45-3)

Conditions	Yield
With aluminum amalgam In tetrahydrofuran; water at -7 - -2℃; for 0.75h;	79%
With aluminum amalgam In tetrahydrofuran; water at 0℃; for 0.333333h;	76%
With ammonium chloride; zinc In tetrahydrofuran at 4 - 6℃; for 16.5h;	68%

N,N'-dihydroxy-2,3-dimethylbutane-2,3-diamine (14384-45-3) + 4,4'-diformylbiphenyl (66-98-8) → 2,2'-(biphenyl-4,4'-diyl)bis(4,4,5,5-tetramethylimidazolidine-1,3-diol) (1227255-67-5)

Conditions	Yield
In toluene for 3h; Reflux; Inert atmosphere;	100%
In toluene Inert atmosphere; Reflux;	95%

diethyl 3-formyl-1H-pyrazole-4,5-dicarboxylate (925687-30-5) + N,N'-dihydroxy-2,3-dimethylbutane-2,3-diamine (14384-45-3) → diethyl 3-(1,3-dihydroxy-4,4,5,5-tetramethylimidazolidin-2-yl)-1H-pyrazole-4,5-dicarboxylate (925687-32-7)

Conditions	Yield
In methanol for 5h;	98%

N,N'-dihydroxy-2,3-dimethylbutane-2,3-diamine (14384-45-3) + 4-hydroxy-3-nitrobenzaldehyde (3011-34-5) → 2-(4-hydroxy-3-nitrophenyl)-4,4,5,5-tetramethylimidazolidine-1,3-diol (1169932-83-5)

Conditions	Yield
In methanol at 20℃; for 3h;	98%

N,N'-dihydroxy-2,3-dimethylbutane-2,3-diamine (14384-45-3) + tolan-4,4'-dicarbaldehyde (84907-55-1) → 2-(4-{2-[4-(1,3-dihydroxy-4,4,5,5-tetramethyl-imidazolidine-2-yl)phenyl]ethynyl}phenyl)-4,4,5,5-tetramethylimidazolidine-1,3-diol

Conditions	Yield
In toluene at 110℃; Inert atmosphere;	98%
In toluene Inert atmosphere; Reflux;	98%

N,N'-dihydroxy-2,3-dimethylbutane-2,3-diamine (14384-45-3) + 5′-(3-(tert-butyl)-4,5-dihydroxyphenyl)-[2,2′-bithiophene]-5-carboxaldehyde → 2-(5′-(3-(tert-butyl)-4,5-dihydroxyphenyl)-[2,2′-bithiophen]-5-yl)-4,4,5,5-tetramethylimidazolidine-1,3-diol

Conditions	Yield
In methanol at 20℃; for 48h; Sealed tube; Schlenk technique; Inert atmosphere; Darkness;	97%

N,N'-dihydroxy-2,3-dimethylbutane-2,3-diamine (14384-45-3) + 4,4'-(buta-1,3-diyne-1,4-diyl)dibenzaldehyde (127653-16-1) → 2-(4-{4-[4-(1,3-dihydroxy-4,4,5,5-tetramethylimidazolidine-2-yl)phenyl]buta-1,3-diyn-1-yl}phenyl)-4,4,5,5-tetramethylimidazolidine-1,3-diol

Conditions	Yield
In toluene at 110℃; for 3h; Inert atmosphere;	97%

N,N'-dihydroxy-2,3-dimethylbutane-2,3-diamine (14384-45-3) + 4-[4-(4-formylmethyl)-2,5-dimethoxyphenyl]benzaldehyde → 2-(4-{4-[4-(1,3-dihydroxy-4,4,5,5-tetramethylimidazolidine-2-yl)phenyl]-2,5-dimethoxyphenyl}phenyl)-4,4,5,5-tetramethylimidazolidine-1,3-diol

Conditions	Yield
In toluene at 110℃; Inert atmosphere;	97%

N,N'-dihydroxy-2,3-dimethylbutane-2,3-diamine (14384-45-3) + 5-formyl-2-hydroxybenzaldehyde (3328-70-9) → C20H34N4O5

Conditions	Yield
In benzene for 21h; Heating;	96%

N,N'-dihydroxy-2,3-dimethylbutane-2,3-diamine (14384-45-3) + benzaldehyde (100-52-7) → 1,3-dihydroxyl-2-phenyl-4,4,5,5-tetramethylimidazolidine (18389-99-6)

Conditions	Yield
With toluene-4-sulfonic acid In methanol at 20℃; for 48h;	96%
In methanol at 20℃; for 1h;	85%
In methanol at 20℃; for 16h;	85%

N,N'-dihydroxy-2,3-dimethylbutane-2,3-diamine (14384-45-3) + o-carboxybenzaldehyde (119-67-5) → 2-(1,3-dihydroxy-4,4,5,5-tetramethyl-imidazolidin-2-yl)-benzoic acid

Conditions	Yield
In methanol at 20℃; for 24h; Cycloaddition;	95%

N,N'-dihydroxy-2,3-dimethylbutane-2,3-diamine (14384-45-3) + 5-bromobenzene-1,3-dicarbaldehyde (120173-41-3) → 1,3-bis(1,3-dihydroxy-4,4,5,5-tetramethylimidazolin-2-yl)-5-bromobenzene (263746-67-4)

Conditions	Yield
In methanol at 20℃; for 72h; Condensation;	95%
In methanol for 72h;	94%

2-(4,5-dibromo-[1,3]dithiol-2-ylidene)-1,3-benzodithiol-5-carbaldehyde (1220993-12-3) + N,N'-dihydroxy-2,3-dimethylbutane-2,3-diamine (14384-45-3) + 2,3-bis(hydroxyamino)-2,3-dimethylbutane monosulfate (14538-51-3, 78375-92-5) → 2-[2-(4,5-dibromo-[1,3]dithiol-2-ylidene)-1,3-benzodithiol-5-yl]-4,4,5,5-tetramethylimidazolidine-1,3-diol (1220993-13-4)

Conditions	Yield
In methanol; benzene for 3h; Inert atmosphere; Reflux;	95%

N,N'-dihydroxy-2,3-dimethylbutane-2,3-diamine (14384-45-3) + 3,6-di-(6-carboxyaldehyde-2-pyridyl)-pyridazine → 3,6-bis[6-(3'-oxide-1'-oxyl-4',4',5',5'-tetramethylimidazolin-2'-yl)-2-pyridyl]pyridazine

Conditions	Yield
With sodium periodate In dichloromethane; water at 0℃;	94%

N,N'-dihydroxy-2,3-dimethylbutane-2,3-diamine (14384-45-3) + 4-chloro-benzoyl chloride (122-01-0) → N,N'-(1,1,2,2-Tetramethylethylen)-bis (73395-03-6)

Conditions	Yield
With triethylamine In benzene at 50℃; for 1h;	94%

N,N'-dihydroxy-2,3-dimethylbutane-2,3-diamine (14384-45-3) + 4-dimethylamino-benzaldehyde (100-10-7) → 1,3-dihydroxy-2-(4'-N,N-dimethylaminophenyl)-4,4,5,5-tetramethylimidazolidine (38577-53-6)

Conditions	Yield
With 2,3-bis(hydroxyamino)-2,3-dimethylbutane monosulfate In ethanol Heating;	94%
With toluene-4-sulfonic acid at 25℃; for 48h;	73%
In methanol at 20℃; for 16h;	31%

m-iodobenzaldehyde (696-41-3) + N,N'-dihydroxy-2,3-dimethylbutane-2,3-diamine (14384-45-3) → 1,3-dihydroxy-2-(3-iodophenyl)-4,4,5,5-tetramethylimidazolidine (868528-73-8)

Conditions	Yield
In methanol at 20℃; for 120h;	94%

N,N'-dihydroxy-2,3-dimethylbutane-2,3-diamine (14384-45-3) + 4-(hydroxylmethyl)benzaldehyde (52010-97-6) → 2-[p-(hydroxymethyl)phenyl]-4,4,5,5-tetramethyl-3-oxylimidazoline 1-oxide

Conditions	Yield
Stage #1: N,N'-dihydroxy-2,3-dimethylbutane-2,3-diamine; 4-(hydroxylmethyl)benzaldehyde In water at 20℃; for 24h; Stage #2: With lead dioxide In water for 2h;	93%

N,N'-dihydroxy-2,3-dimethylbutane-2,3-diamine (14384-45-3) + phenyl isocyanate (103-71-9) → N,N'-(1,1,2,2-Tetramethylethylen)-bis(O-phenylcarbamoylhydroxylamin) (73395-05-8)

Conditions	Yield
In benzene for 0.166667h; Heating;	92%

N,N'-dihydroxy-2,3-dimethylbutane-2,3-diamine (14384-45-3) + 4-Ethynylbenzaldehyde (63697-96-1) → 4-ethynyl-1-(1,3-dihydroxy-4,4,5,5-tetramethylimidazolin-2-yl)benzene (124774-78-3)

Conditions	Yield
In methanol at 20℃; Condensation;	91%
In methanol for 24h; Heating;	78%
In methanol for 12h; Reflux; Inert atmosphere;

N,N'-dihydroxy-2,3-dimethylbutane-2,3-diamine (14384-45-3) + 3-tert-butyl-4,5-dimethoxybenzaldehyde (333401-63-1) → 2-(3-tert-butyl-4,5-dimethoxy-phenyl)-4,4,5,5-tetramethyl-imidazolidine-1,3-diol (501912-09-0)

Conditions	Yield
In methanol for 12h; Heating;	91%

5,11,17,23-tetraformyl-25,26,27,28-tetrakis(2-methoxyethoxy)calix[4]arene + N,N'-dihydroxy-2,3-dimethylbutane-2,3-diamine (14384-45-3) → 5,11,17,23-tetrakis(1,3-dihydroxy-4,4,5,5-tetramethylimidazolidin-2-yl)-25,26,27,28-tetrakis(2-methoxyethoxy)calix[4]arene

Conditions	Yield
With toluene-4-sulfonic acid In methanol at 60 - 65℃;	91%

N,N'-dihydroxy-2,3-dimethylbutane-2,3-diamine (14384-45-3) + 5-formyl-2-nitrophenol (704-13-2) → 2-(3-hydroxy-4-nitrophenyl)-4,4,5,5-tetramethylimidazolidine-1,3-diol (1169932-82-4)

Conditions	Yield
In methanol at 20℃; for 3h;	91%

N,N'-dihydroxy-2,3-dimethylbutane-2,3-diamine (14384-45-3) + 4-[2-(5,6-dihydro-[1,3]dithiolo[4,5-b][1,4]dithiin-2-ylidene)-5-methylsulfanyl-[1,3]dithiol-4-yl]-benzaldehyde (241156-88-7) → 2-{4-[2-(5,6-dihydro-[1,3]dithiolo[4,5-b][1,4]dithiin-2-ylidene)-5-methylsulfanyl-[1,3]dithiol-4-yl]-phenyl}-4,4,5,5-tetramethyl-imidazolidine-1,3-diol (241156-91-2)

Conditions	Yield
With sulfuric acid In hexane; dichloromethane Cycloaddition; Heating;	90%

N,N'-dihydroxy-2,3-dimethylbutane-2,3-diamine (14384-45-3) + m,m'-bisformylbenzene-4-ethynyl-benzaldehyde (263746-71-0) → C35H52N6O6 (263746-68-5)

Conditions	Yield
In methanol at 20℃; for 72h; Condensation;	90%
In methanol for 72h;	90%

Isophthalaldehyde (626-19-7) + N,N'-dihydroxy-2,3-dimethylbutane-2,3-diamine (14384-45-3) → 1,3-Bis(1,3-dihydroxy-4,4,5,5-tetramethylimidazolin-2-yl)benzene

Conditions	Yield
In methanol at 20℃; for 24h;	90%

5,17-diformyl-11,23-dibromo-25,26,27,28-tetrakis(2-methoxyethoxy)calix[4]arene (955121-14-9) + N,N'-dihydroxy-2,3-dimethylbutane-2,3-diamine (14384-45-3) → 5,17-bis(1,3-dihydroxy-4,4,5,5-tetramethylimidazolidin-2-yl)-11,23-dibromo-25,26,27,28-tetrakis(2-methoxyethoxy)calix[4]arene (955121-16-1)

Conditions	Yield
With toluene-4-sulfonic acid In methanol at 55 - 60℃;	90%

N,N'-dihydroxy-2,3-dimethylbutane-2,3-diamine (14384-45-3) + Cyclohexyl isocyanate (3173-53-3) → N,N'-(1,1,2,2-Tetramethylethylen)-bis(O-cyclohexylcarbamoylhydroxylamin) (73433-44-0)

Conditions	Yield
In benzene for 0.166667h; Heating;	88%

2,5-Dihydroxybenzaldehyde (1194-98-5) + N,N'-dihydroxy-2,3-dimethylbutane-2,3-diamine (14384-45-3) → 2-(2,5-Dihydroxy-phenyl)-4,4,5,5-tetramethyl-imidazolidine-1,3-diol

Conditions	Yield
With 2,3-dimethyl-2,3-(dihydroxylaminium)butane sulfonate; 3 A molecular sieve In methanol; benzene for 96h;	88%

N,N'-dihydroxy-2,3-dimethylbutane-2,3-diamine (14384-45-3) + 2,2′-bipyridine-5,5′-dicarbaldehyde (135822-72-9) → 5,5'-bis(1,3-dihydroxy-4,4,5,5-tetramethylimidazolin-2-yl)-2,2'-bipyridine

Conditions	Yield
In toluene Inert atmosphere; Reflux;	88%
In methanol at 20℃; for 72h; Condensation;	85%

2-iodobenzaldehyde (26260-02-6) + N,N'-dihydroxy-2,3-dimethylbutane-2,3-diamine (14384-45-3) → 1,3-dihydroxy-2-(2-iodophenyl)-4,4,5,5-tetramethylimidazolidine (868528-72-7)

Conditions	Yield
In methanol at 20℃; for 120h;	88%

Upstream product

• 3964-18-9 2,3-dimethyl-2,3-dinitrobutane 
• 14538-51-3 2,3-bis(hydroxyamino)-2,3-dimethylbutane monosulfate 

Downstream Products

• 77667-29-9 4-(1,3-dihydroxy-4,4,5,5-tetramethylimidazolidin-2-yl)phenyl-2,3,4,6-tetra-O-acetyl β-D-galactopyranoside 
• 125520-16-3 C₂₇H₄₈N₆O₆ 
• 78375-91-4 1,3-dihydroxy-2--4,4,5,5-tetramethyl-2-imidazoline 
• 77667-30-2 4-(1,3-dihydroxy-4,4,5,5-tetramethylimidazolidin-2-yl)-2-nitrophenyl2,3,4-tri-O-acetyl-β-D-fucopyranoside 
• 77667-28-8 4-(1,3-dihydroxy-4,4,5,5-tetramethylimidazolidin-2-yl)-2-nitrophenyl-2,3,4,6-tetra-O-acetyl β-D-galactopyranoside 
• 127-06-0 acetone oxime 
• 34493-89-5 3,4-Dihydro-3,3,4,4-tetramethyl-1,2-diazete 1,2-dioxide 
• 73433-44-0 N,N'-(1,1,2,2-Tetramethylethylen)-bis(O-cyclohexylcarbamoylhydroxylamin) 
• 73393-96-1 N,N'-(1,1,2,2-Tetramethylethylen)-bis(N-cyclohexylcarbamoylhydroxylamin) 
• 73395-06-9 N,N'-(1,1,2,2-Tetramethylethylen)-bis 
• 1027018-97-8 1,3-bis[2-(1,3-hydroxy-4,4,5,5-tetramethylimidazolin-2-yl)imidazol-1-yl]benzene 
• 117566-79-7 2-(2-chlorophenyl)-4,5-dihydro-4,4,5,5-tetramethyl-3-oxido-1H-imidazol-3-ium-1-oxyl 
• 241156-89-8 2-(4-[2,2']bi[[1,3]dithiolylidene]-4-yl-phenyl)-4,4,5,5-tetramethyl-imidazolidine-1,3-diol 
• 241156-90-1 2-{4-[2-(5,6-dihydro-[1,3]dithiolo[4,5-b][1,4]dithiin-2-ylidene)-[1,3]dithiol-4-yl]-phenyl}-4,4,5,5-tetramethyl-imidazolidine-1,3-diol 

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Magnetic complex and preparation method thereof

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