20485-44-3

Basic information

• Product Name: 2,3-Diamino-2,3-dimethylbutane
• Synonyms: 2,3-Diamino-2,3-dimethylbutane;2,3-ButanediaMine, 2,3-diMethyl-;2,3-Dimethyl-2,3-butanediamine;2,3-Dimethyl-2,3-diaminobutane;2,3-dimethylbutane-2,3-diamine
• CAS NO: 20485-44-3
• Molecular Formula: C₆H₁₆N₂
• Molecular Weight: 116
• Mol File: 20485-44-3.mol
• Article Data: 12

Chemical Properties

• Melting Point: 97-98 °C
• Boiling Point: 157.2 °C at 760 mmHg
• Flash Point: 43.4 °C
• Appearance: /
• Density: 0.86 g/cm³
• Vapor Pressure: 2.79mmHg at 25°C
• Refractive Index: 1.458
• PKA: 10.06±0.25(Predicted)
• CAS DataBase Reference: 2,3-Diamino-2,3-dimethylbutane(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-Diamino-2,3-dimethylbutane(20485-44-3)
• EPA Substance Registry System: 2,3-Diamino-2,3-dimethylbutane(20485-44-3)

Safety Data

• Hazardous Substances Data: 20485-44-3(Hazardous Substances Data)

Usage

General Description

2,3-Diamino-2,3-dimethylbutane is an organic compound and a specific type of diamine, a class of chemicals featuring two amino functional groups. It has a branched, aliphatic structure, with two tertiary amines and two methyl groups attached to a central carbon-carbon bond. The formula for this compound is C6H16N2 and it is solid under normal conditions. Its properties, such as boiling point, melting point, or apparent solubility, depend on intermolecular interactions and can be influenced by factors like sterical hindrance due to its bulky, branched structure. As with all amines, it can act as a base, is capable of forming salts with acids, and it may display high reactivity.

InChI:InChI=1/C6H16N2/c1-5(2,7)6(3,4)8/h7-8H2,1-4H3

Synthetic route

2,3-dimethyl-2,3-dinitrobutane (3964-18-9) → 2,3-dimethyl-2,3-diaminobutane (20485-44-3)

Conditions	Yield
With hydrogenchloride; tin for 3h; Heating;	81%
With hydrogenchloride; tin	75%
With hydrogenchloride; tin In water at 105℃; for 4h;	60%

2,3-Dimethyl-2-butene (563-79-1) → 2,3-dimethyl-2,3-diaminobutane (20485-44-3)

Conditions	Yield
With lithium aluminium tetrahydride; 2; nitrogen(II) oxide 1) THF, 0 deg C, 85 min; 2) THF, -70 deg C, room temperature (overnight), reflux (1 h); Yield given. Multistep reaction;
Multi-step reaction with 2 steps 1: diethyl ether; dinitrogen tetraoxide / -20 - -16 °C 2: platinum; glacial acetic acid / Hydrogenation View Scheme

isopropylamine (75-31-0) → 2,3-dimethyl-2,3-diaminobutane (20485-44-3)

{Co(tmen)3}(3+) (131611-95-5) → 2,3-dimethyl-2,3-diaminobutane (20485-44-3) + cobalt(II)

Conditions	Yield
With V(2+)aq. In perchloric acid Kinetics; reduction with V(2+)aq. at 25°C in 1M HClO4; monitored spectrophotometrically;
With Cr(2+)aq. In further solvent(s) Kinetics; reduction with Cr(2+)aq. at 25°C in 1M CF3SO3Na + 0.1M CF3SO3H; monitored spectrophotometrically;
With Eu(2+)aq. In perchloric acid Kinetics; redution with Eu(2+)aq. at 25°C in 1M HClO4; monitored spectrophotometrically;

{Co(tmen)3}(3+) (131611-95-5) + Co(sep)(2+) (82796-47-2, 63218-22-4, 82837-80-7) → 2,3-dimethyl-2,3-diaminobutane (20485-44-3) + cobalt(II)

Conditions	Yield
In further solvent(s) Kinetics; reduction at 25°C in 0.2 M NaCl; monitored spectrophotometrically;

{Co(tmen)3}(3+) (131611-95-5) + hexaaquaruthenium(II) (30251-71-9) → 2,3-dimethyl-2,3-diaminobutane (20485-44-3) + cobalt(II)

Conditions	Yield
In further solvent(s) Kinetics; at 25°C in 1M CF3SO3Na + 0.1M CF3SO3H; monitored spectrophotometrically;

2,3-dimethyl-2,3-diaminobutane (20485-44-3) + benzaldehyde (100-52-7) → 2-Phenyl-4,4,5,5-tetramethylimidazolidine (351902-03-9)

Conditions	Yield
In diethyl ether ice cooling;	99%

butyl-hydroxy-toluene + 2,3-dimethyl-2,3-diaminobutane (20485-44-3) + potassium methacrylate (6900-35-2) + 1-Chloro-4-(chloromethyl)benzene (104-83-6)

Conditions	Yield
In toluene	98.2%

+ 2,3-dimethyl-2,3-diaminobutane (20485-44-3) + potassium methacrylate (6900-35-2)

Conditions	Yield
In toluene	97.4%

2,3-dimethyl-2,3-diaminobutane + salicylaldehyde (90-02-8) → N,N'-(1,1,2,2-tetramethylethylene)bis(salicylideneimine) (60306-02-7)

Conditions	Yield
	96%
With ethanol

1-acetyl-4-piperidinone (32161-06-1) + 2,3-dimethyl-2,3-diaminobutane (20485-44-3) → 8-acetyl-2,2,3,3-tetramethyl-1,4,8-triazaspiro<4.5>decane (113646-69-8)

Conditions	Yield
With potassium carbonate; toluene-4-sulfonic acid In benzene for 48h; Heating;	95%

3-pyridinecarboxaldehyde (500-22-1) + 2,3-dimethyl-2,3-diaminobutane (20485-44-3) → 3-(4,4,5,5-tetramethyl-imidazolidin-2-yl)-pyridine (351902-05-1)

Conditions	Yield
In diethyl ether ice cooling;	95%

2,3-dimethyl-2,3-diaminobutane (20485-44-3) + pivalaldehyde (630-19-3) → 2-tert-butyl-4,4,5,5-tetramethyl-imidazolidine (351902-08-4)

Conditions	Yield
In diethyl ether ice cooling;	95%

2,3-dimethyl-2,3-diaminobutane (20485-44-3) + 4-nitrobenzaldehdye (555-16-8) → 4,4,5,5-tetramethyl-2-(4-nitro-phenyl)-imidazolidine (351902-04-0)

Conditions	Yield
In diethyl ether ice cooling;	92%

2,3-dimethyl-2,3-diaminobutane (20485-44-3) + (4S)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (102308-32-7) → tert-butyl (4R)-2,2-bimethyl-4-(4,4,5,5-tetramethylimidazolidine-2-yl)-1,3-oxazolidine-3-carboxylate (1571095-85-6)

Conditions	Yield
In dichloromethane for 19h; Reflux; Molecular sieve;	92%

Conditions	Yield
In ethanol OsCl3*3H2O reacting with excess base in EtOH at 50°C for 10 min; pptn.; elem. anal.;	90%

+ 2,3-dimethyl-2,3-diaminobutane + sodium iodide → Os(NHC(CH3)2C(CH3)2NH2)2(NH2C(CH3)2C(CH3)2NH2)(2+)*2I(1-)*H2O={Os(NHC(CH3)2C(CH3)2NH2)2(NH2C(CH3)2C(CH3)2NH2)}I2*H2O

Conditions	Yield
In water addn. of Os-salt to excess base in H2O; keeping at 40°C for 30 min, addn. of NaI; brown ppt.; filtration; washing (ice-cold H2O, EtOH; ether); recrystn. (H2O); elem. anal.;	90%

diammonium hexachloroosmate(IV) + 2,3-dimethyl-2,3-diaminobutane (20485-44-3) + sodium iodide (7681-82-5) → Os(NHC(CH3)2C(CH3)2NH2)2(NH2C(CH3)2C(CH3)2NH2)(2+)*2I(1-)*H2O={Os(NHC(CH3)2C(CH3)2NH2)2(NH2C(CH3)2C(CH3)2NH2)}I2*H2O

Conditions	Yield
In water addn. of Os-salt to excess base in H2O; keeping at 40°C for 30 min, addn. of NaI; brown ppt.; filtration; washing (ice-cold H2O, EtOH; ether); recrystn. (H2O); elem. anal.;	90%

2,3-dimethyl-2,3-diaminobutane (20485-44-3) + 1-bromo-2-(2-methoxyethoxy)ethane (54149-17-6) + bis(4-hydroxyphenyl) sulfoxide (1774-34-1) → 4,4'-sulfinylbis((2-(2-methoxyethoxy)ethoxy)benzene) (1379476-07-9)

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide	90%

5-bromo-2-dimethylaminopyridine (26163-07-5) + 2,3-dimethyl-2,3-diaminobutane (20485-44-3) → 6-(dimethylamino)nicotine-3-carboxaldehyde (149805-92-5)

Conditions	Yield
In diethyl ether; N,N-dimethyl-formamide	89.6%

formaldehyd (50-00-0) + 2,3-dimethyl-2,3-diaminobutane (20485-44-3) → 4,4,5,5-tetramethyl-imidazolidine (351902-06-2)

Conditions	Yield
In diethyl ether ice cooling;	89%

nickel(II) chloride hexahydrate + 2,3-dimethyl-2,3-diaminobutane (20485-44-3) + 5-(azidomethyl)-2-hydroxybenzaldehyde (714916-55-9) → C22H24N8NiO2 (1427467-70-6)

Conditions	Yield
Stage #1: 2,3-dimethyl-2,3-diaminobutane; 5-(azidomethyl)-2-hydroxybenzaldehyde In ethanol Inert atmosphere; Schlenk technique; Stage #2: nickel(II) chloride hexahydrate With triethylamine In ethanol Inert atmosphere; Schlenk technique;	88%

2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9) + 2,3-dimethyl-2,3-diaminobutane (20485-44-3) → 2-(4',4',5',5'-tetramethylimidazolidine-2'-yl)-2-methylpropanol (1309974-80-8)

Conditions	Yield
In chloroform for 24h; Molecular sieve; Reflux;	87%

2,3-dimethyl-2,3-diaminobutane (20485-44-3) + disodium 3-(2-methoxyethoxy)salicylaldehyde-5-sulfonate + nickel(II) acetate tetrahydrate (6018-89-9) → C26H32N2NiO12S2(2-)*2Na(1+)

Conditions	Yield
In water at 20℃; for 1h;	86.5%

(2-furyl)diphenylphosphane (40927-82-0) + 2,3-dimethyl-2,3-diaminobutane (20485-44-3) → sodium 5-(diphenylphosphanyl)-furyl-2-carboxylate

Conditions	Yield
With hydrogenchloride; sodium hydroxide; n-butyllithium; nitrogen In diethyl ether; water; sodium hydrogencarbonate	85%

ammonium hexafluorophosphate + trichloro(2,2'-bipyridine)ruthenium (69141-04-4) + 2,3-dimethyl-2,3-diaminobutane (20485-44-3) + zinc (7440-66-6) → [Ru(II)(2,2'-bipyridine)(2,3-diamino-2,3-dimethylbutane)2](PF6)2

Conditions	Yield
In ethanol refluxing Ru-complex, ligand and Zn-dust for 6 h, cooling, filtration, addn. of satd. NH4PF6; concn. (reduced pressure), collection, washing (water, Et2O); elem. anal.;	85%

2,3-dimethyl-2,3-diaminobutane (20485-44-3) + di-tert-butyl dicarbonate (24424-99-5) → N-tert-butoxycarbonyl-2,3-dimethyl-2,3-diaminobutane (1306610-31-0)

Conditions	Yield
In dichloromethane at 20℃; for 7h; Inert atmosphere;	85%

2,3-dimethyl-2,3-diaminobutane (20485-44-3) + diethyl malonate (105-53-3) → 5-carbethoxy-2,2,3,3-tetramethyl-2,3-dihydropyrazin-6-one (92958-09-3)

Conditions	Yield
In ethanol 1) r.t, 45 h, 2) reflux, 7.5 h;	83%

4-(trifluoromethyl)phenyl 2-tetrahydropyranyl ether + tert-butyl methyl ether (1634-04-4) + 2,3-dimethyl-2,3-diaminobutane (20485-44-3) + diphenyldisulfane (882-33-7) → 2-[2-(phenylsulfanyl)-4-(trifluoromethyl)phenoxy]tetrahydro-2H-pyran

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane; water	82.7%

2,3-dimethyl-2,3-diaminobutane (20485-44-3) + chromium(III) chloride (10025-73-7) → tris(2,3-diamino-2,3-dimethylbutane)chromium(III)(Cl)3

Conditions	Yield
With zinc In tetrahydrofuran A slurry of CrCl3, 2,3-diamino-2,3-dimethylbutane and a grain of zinc was boiled under reflux for 200 h. Moisture was excluded by means of a CaCl2 tube.; removing of the remaining zinc, centrifugation, washing with 2 M HCl, drying in vacuo;	80%

hydrogenchloride (7647-01-0) + trichloro(2,2'-bipyridine)ruthenium (69141-04-4) + 2,3-dimethyl-2,3-diaminobutane (20485-44-3) + zinc (7440-66-6) → [Ru(II)(2,2'-bipyridine)(2,3-diamino-2,3-dimethylbutane)2][ZnCl4] (177416-75-0)

Conditions	Yield
In ethanol refluxing Ru-complex, ligand and Zn-dust for 6 h, cooling, filtration, addn. of 0.2 M HCl; concn. (reduced pressure), collection, washing (water, Et2O); elem. anal.;	80%

ruthenium(III) chloride trihydrate + 2,3-dimethyl-2,3-diaminobutane (20485-44-3) + 2-[[(2-hydroxyphenyl)imino]methyl]phenol (1761-56-4) + water (7732-18-5) → aquotetramethylethylenediamine(2-hydroxyphenyl-2-salicylaldiminato)ruthenium(III)chloride (1239712-76-5)

Conditions	Yield
In methanol C6H16N2 added to MeOH soln. of C13H11NO2, then Ru salt added, mixt. refluxed for 8 h; ppt. sepd., filtered, washed (H2O, little MeOH), dried in desiccator over CaCl2; elem. anal.;	80%

2,3-dimethyl-2,3-diaminobutane (20485-44-3) + 2-hydroxy-2',4',5,6'-tetramethyl-[1,1'-biphenyl]-3-carbaldehyde (1448442-53-2) → 3,3''-((1E,1'E)-((2,3-dimethylbutane-2,3-diyl)bis(azanylylidene))bis(methanylylidene))bis(2',4',5,6'-tetramethyl-[1,1'-biphenyl]-2-ol) (1448442-60-1)

Conditions	Yield
With air In methanol at 65℃; for 7h;	80%

2,3-dimethyl-2,3-diaminobutane (20485-44-3) + 3,5-dimethylsalicylaldehyde (24623-61-8) → 6,6′-((1E,1′E)-((2,3-dimethylbutane-2,3-diyl)bis(azanylylidene))-bis(methanylylidene))bis(2,4-dimethylphenol)

Conditions	Yield
In methanol at 70℃; for 12h;	80%

aqueous Na2 CO3 + Trimethyl borate (121-43-7) + 2,3-dimethyl-2,3-diaminobutane (20485-44-3) + 2-trityl-5-phenyl-2H-tetrazole (87268-78-8)

Conditions	Yield
With sec.-butyllithium; Pd(PPh3)4 In tetrahydrofuran; benzene	79%

Upstream product

• 131611-95-5 {Co(tmen)3}⁽³⁺⁾ 
• 82796-47-2 Co(sep)⁽²⁺⁾ 
• 30251-71-9 hexaaquaruthenium(II) 
• 75-31-0 isopropylamine 
• 563-79-1 2,3-Dimethyl-2-butene 
• 3964-18-9 2,3-dimethyl-2,3-dinitrobutane 

Downstream Products

• 60306-02-7 N,N'-(1,1,2,2-tetramethylethylene)bis(salicylideneimine) 
• 351902-03-9 2-Phenyl-4,4,5,5-tetramethylimidazolidine 
• 5029-67-4 2-iodopyridine 
• 113975-32-9 2,2-dimethyl-N-(4-iodo-3-pyridinyl)propanamide 
• 358753-30-7 1,2,3,4,5,6,7,8-octapropylanthracene 
• 188396-79-4 1-benzyl-4-tributylstannyl-1,2,3,6-tetrahydropyridine 
• 181695-99-8 4-[3-[2-(4-chlorophenyl)-2-hydroxyethyl]-5-phenylisoxazol-4-yl]benzenesulfonamide 
• 91562-20-8 1-tert-butyl-4-iodo-2,5-dimethoxybenzene 
• 133742-77-5 2-aminosulfonyl-6-methoxy-N,N-diethylbenzamide 
• 145096-35-1 α-(pyridin-3-yl)-2,5-dimethoxy-4,6-dimethylbenzyl alcohol 
• 135217-58-2 6-ethyl-N,N-dimethyl-2-methoxy-benzamide 
• 177365-41-2 2-bromo-6-tert-butylthiophenol 

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