626-23-3

Basic information

• Product Name: Di-sec-butylamine
• Synonyms: (sec-C4H9)2NH;1-Propanamine, 1-methyl, N-(1-methylpropyl);2-Butanamine,N-(1-methylpropyl)-;Bis(1-methylpropyl)amine;Bis(sec-butyl)amine;Di-2-butylamine;n-(1-methylpropyl)-2-butanamin;N-(Sec-butyl)-2-butanamine
• CAS NO: 626-23-3
• Molecular Formula: C₈H₁₉N
• Molecular Weight: 129.24
• EINECS: 210-937-9
• Product Categories: Amines;C8;Nitrogen Compounds;Building Blocks;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks
• Mol File: 626-23-3.mol
• Article Data: 12

Chemical Properties

• Melting Point: -70°C
• Boiling Point: 135 °C765 mm Hg(lit.)
• Flash Point: 69 °F
• Appearance: clear liquid
• Density: 0.753 g/mL at 25 °C(lit.)
• Vapor Pressure: 7.07mmHg at 25°C
• Refractive Index: n20/D 1.41(lit.)
• PKA: pK1:10.91(+1) (25°C)
• CAS DataBase Reference: Di-sec-butylamine(CAS DataBase Reference)
• NIST Chemistry Reference: Di-sec-butylamine(626-23-3)
• EPA Substance Registry System: Di-sec-butylamine(626-23-3)

Safety Data

• Hazard Codes: F,C,Xn
• Statements: 11-20/21/22-34-10
• Safety Statements: 16-26-27-33-36/37/39-45
• RIDADR: UN 2733 3/PG 2
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 626-23-3(Hazardous Substances Data)

Usage

Uses

Di-sec-butylamine is an aliphatic amine of research interest that has been studied for its properties to attach to carbon and metal surfaces, proton affinity, as well as hydrodesulfurization and hydrodenitrogenation in petroleum refining.

InChI:InChI=1/C8H19N/c1-5-7(3)9-8(4)6-2/h7-9H,5-6H2,1-4H3

Synthetic route

ethyl methyl ketone oxime (96-29-7) → SEC-BUTYLAMINE (33966-50-6) + Di-sec-butylamin (626-23-3)

Conditions	Yield
With hydrogen; copper
With hydrogen; nickel at 150 - 200℃;

N-2-butylidene-2-aminobutane (38836-40-7) → Di-sec-butylamin (626-23-3)

Conditions	Yield
With nickel at 100 - 150℃; under 11032.6 - 51485.6 Torr; Hydrogenation;

SEC-BUTYLAMINE (33966-50-6) + s-butyl bromide (78-76-2, 5787-31-5) → Di-sec-butylamin (626-23-3)

Conditions	Yield
With ethanol

butan-2-one phenylhydrazone (1129-62-0) → SEC-BUTYLAMINE (33966-50-6) + Di-sec-butylamin (626-23-3)

Conditions	Yield
With ethanol; aluminium amalgam

butanone (78-93-3) → Di-sec-butylamin (626-23-3)

Conditions	Yield
With ammonia Hydrogenation;

butanone (78-93-3) → Di-sec-butylamin (626-23-3) + iso-butanol (78-92-2, 15892-23-6)

Conditions	Yield
With Pt/Al2O3; colloid; ammonia; water at 25℃; under 2280 Torr; Hydrogenation.Ueberdruck;

N-2,6-Dimethylphenyl-N',N'-di-sec-butylharnstoff (51608-96-9) → Di-sec-butylamin (626-23-3) + 2,6-dimethylphenylisocyanate (28556-81-2)

Conditions	Yield
With methoxybenzene at 127℃; Equilibrium constant;

SEC-BUTYLAMINE (33966-50-6) + butanone (78-93-3) → Di-sec-butylamin (626-23-3)

Conditions	Yield
With hydrogenchloride; hydrogen; platinum(IV) oxide

N,N-Di-sek.-butyl-N'-phenyl-harnstoff (53463-31-3) + N-methylaniline (100-61-8) → Di-sec-butylamin (626-23-3) + 1-methyl-1,3-diphenylurea (612-01-1)

Conditions	Yield
In nitrobenzene at 120℃; Equilibrium constant;

1-butylene (106-98-9) → SEC-BUTYLAMINE (33966-50-6) + butene-2 (107-01-7) + Di-sec-butylamin (626-23-3)

Conditions	Yield
With ammonia; HY2.5 zeolite at 317.9℃; under 30002.4 Torr; Rate constant; Thermodynamic data; other catalysts, var. temp.; other butene; E(excit.);

ethanol (64-17-5) + butan-2-one phenylhydrazone (1129-62-0) + amalgamated aluminium → SEC-BUTYLAMINE (33966-50-6) + Di-sec-butylamin (626-23-3) + aniline (62-53-3)

ammonium hydroxide + butanone (78-93-3) + platinum → Di-sec-butylamin (626-23-3) + iso-butanol (78-92-2, 15892-23-6)

Conditions	Yield
under 2280 Torr; Hydrogenation;

ethyl methyl ketone oxime (96-29-7) + hydrogen + copper → SEC-BUTYLAMINE (33966-50-6) + Di-sec-butylamin (626-23-3)

ethyl methyl ketone oxime (96-29-7) + hydrogen + nickel → SEC-BUTYLAMINE (33966-50-6) + Di-sec-butylamin (626-23-3)

Conditions	Yield
at 150 - 200℃;

sec. butyl magnesium iodide (14753-38-9) + NCl3 → SEC-BUTYLAMINE (33966-50-6) + Di-sec-butylamin (626-23-3) + NH3

sec-butylmagnesium bromide (671795-46-3) + NCl3 → SEC-BUTYLAMINE (33966-50-6) + Di-sec-butylamin (626-23-3) + NH3

sec-butyl magnesium (1+); chloride + NCl3 → SEC-BUTYLAMINE (33966-50-6) + Di-sec-butylamin (626-23-3) + NH3

sec-butyl magnesium (1+); chloride + NHBr2 → SEC-BUTYLAMINE (33966-50-6) + Di-sec-butylamin (626-23-3) + nitrogen + NH3

N,N-Di-sek.-butyl-N'-phenyl-harnstoff (53463-31-3) → Di-sec-butylamin (626-23-3) + aniline (62-53-3)

Conditions	Yield
With sulfuric acid In methanol; water at 80 - 90℃; Kinetics; Further Variations:; Temperatures;

SEC-BUTYLAMINE (33966-50-6) → Di-sec-butylamin (626-23-3) + butanone (78-93-3)

Conditions	Yield
With aluminium; platinum on activated charcoal In water for 0.166667h; microwave irradiation;	A 37 % Chromat. B 58 % Chromat.
With water; palladium on activated charcoal at 170℃; for 9h; Title compound not separated from byproducts;

butanone (78-93-3) → SEC-BUTYLAMINE (33966-50-6) + Di-sec-butylamin (626-23-3) + iso-butanol (78-92-2, 15892-23-6)

Conditions	Yield
With ammonia; hydrogen; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 2,2'-bis[[bis(3-sulfophenyl)phosphino]methyl]-4,4',7,7'-tetrasulfo-1,1'-binaphthyl octasodium salt In water at 130℃; under 82508.3 Torr; for 5h; Product distribution / selectivity;

tetrakis(di-sec-butylammonium) decaselenidotetrastannanate dihydrate → tin(II) selenide + tin diselenide + Di-sec-butylamin (626-23-3) + water (7732-18-5) + hydrogen selenide (13940-22-2)

Conditions	Yield
In neat (no solvent) thermal decomp. up to 700 °C, Se was also formed;

SEC-BUTYLAMINE (33966-50-6) → Di-sec-butylamin (626-23-3) + iso-butanol (78-92-2, 15892-23-6)

Conditions	Yield
With 5% Rh/C; aluminium In water at 120℃; for 3h; Sealed tube;	A 60 %Chromat. B 24 %Chromat.
With Ru/C; aluminium In water at 120℃; for 3h; Sealed tube;	A 21 %Chromat. B 66 %Chromat.

iso-butanol (78-92-2, 15892-23-6) → Di-sec-butylamin (626-23-3)

Conditions	Yield
With ammonium carbonate In 5,5-dimethyl-1,3-cyclohexadiene for 24h; Inert atmosphere; Sealed tube; Reflux;	73 %Chromat.

N-sec-butylidene-sec-butylamine (38836-40-7) → Di-sec-butylamin (626-23-3)

Conditions	Yield
With sodium tetrahydroborate In methanol at 0℃; for 1h; Inert atmosphere;

s-butyl bromide (78-76-2, 5787-31-5) → SEC-BUTYLAMINE (33966-50-6) + Di-sec-butylamin (626-23-3)

Conditions	Yield
With 5-methyl-1,3,4-thiadiazol-2-amine; potassium carbonate In ethanol; water at 25℃; for 1h; Overall yield = 78 %;

Di-sec-butylamin (626-23-3) + trimethyl indium (3385-78-2) → In(CH3)3(HN(CH3CHCH2CH3)2)

Conditions	Yield
In pentane (N2); filtn., stirring; solvent removal (vac.);	99%

Di-sec-butylamin (626-23-3) + Heptanoic acid chloride (2528-61-2) → Heptanoic acid di-sec-butyl-amide (53463-20-0)

Conditions	Yield
With triethylamine	97.6%

Di-sec-butylamin (626-23-3) + 3-phenylbutanoyl chloride (51552-98-8) → N,N-Di-sec-butyl-3-phenyl-butyramide (91424-88-3)

Conditions	Yield
With triethylamine	94.24%

Di-sec-butylamin (626-23-3) + isovaleraldehyde (590-86-3) → Di-sec-butyl-((E)-3-methyl-but-1-enyl)-amine

Conditions	Yield
In benzene for 12h; Heating;	93%

Di-sec-butylamin (626-23-3) + boron trichloride (10294-34-5) → dichlorodi-sec.-butylaminoborane (81121-54-2)

Conditions	Yield
	92%
	92%

carbon disulfide (75-15-0) + Di-sec-butylamin (626-23-3) + 2-(2-naphthyloxy)-1-chloroethane (3383-79-7) → C21H29NOS2

Conditions	Yield
Stage #1: carbon disulfide; Di-sec-butylamin With triton-B In dimethyl sulfoxide at 20℃; for 1h; Inert atmosphere; Stage #2: 2-(2-naphthyloxy)-1-chloroethane In dimethyl sulfoxide for 0.5h; Inert atmosphere;	90.2%

carbon disulfide (75-15-0) + Di-sec-butylamin (626-23-3) + 4-(2-naphthyloxy)-1-chlorobutane (653573-32-1) → C23H33NOS2

Conditions	Yield
Stage #1: carbon disulfide; Di-sec-butylamin With triton-B In dimethyl sulfoxide at 20℃; for 1h; Inert atmosphere; Stage #2: 4-(2-naphthyloxy)-1-chlorobutane In dimethyl sulfoxide for 0.583333h; Inert atmosphere;	90.2%

carbon disulfide (75-15-0) + Di-sec-butylamin (626-23-3) + 1-chloro-3-(2-naphthyloxy)propane (56231-42-6) → C22H31NOS2

Conditions	Yield
Stage #1: carbon disulfide; Di-sec-butylamin With triton-B In dimethyl sulfoxide at 20℃; for 1h; Inert atmosphere; Stage #2: 3-(2-naphthyloxy)-1-chloropropane In dimethyl sulfoxide for 0.416667h; Inert atmosphere;	90.2%

Di-sec-butylamin (626-23-3) + triethylamine-borane (1722-26-5) → bis(sec-butyl)aminoborane (22093-00-1) + hydrogen (1333-74-0) + triethylamine (121-44-8)

Conditions	Yield
equimolar amounts of educts, 150-160°C;;	A 90% B n/a C n/a
equimolar amounts of educts, 150-160°C;;	A 90% B n/a C n/a

Di-sec-butylamin (626-23-3) + trimethyl gallium (1445-79-0) → Ga(CH3)3(HN(CH3CHCH2CH3)2)

Conditions	Yield
(N2); -70°C, warming to 25°C;	90%

ethylenebis(triphenylphosphine)platinum(0) (12120-15-9) + Di-sec-butylamin (626-23-3) + 3-phenylprop-2-ynyl 4-methylbenzenesulfonate (21541-60-6) → (PPh3)2Pt(η3-CH2C(N(sec-Bu)2)CHPh)TOf (539848-02-7)

Conditions	Yield
In dichloromethane ligand was added to stirred soln. of Pt-complex in CH2Cl2 at 0°C,warmed to room temp., amine was introduced, stirred for 30 min under Ar; volatiles were removed under reduced pressure, washed with hexane, driedunder vac. for several d;	90%

Di-sec-butylamin (626-23-3) + trimethylaluminum (75-24-1) → [(CH3)2AlN(CH(CH3)C2H5)2]2

Conditions	Yield
In toluene absence of air and moisture; refluxing equimolar amts. for 3 d; concn. (vac.), crystn. (-15°C); elem. anal.;	85%

Di-sec-butylamin (626-23-3) + pyridinium tetrafluoroborate → pyridine (110-86-1) + di-i-butylammonium tetrafluoroborate (17251-80-8)

Conditions	Yield
In water taking C5H5NHBF4 in a beaker, cooling in an ice-bath, dropwise addn. of the amine, exothermic react., stirring the soln. at 0 - 5°C (30 min); extn. of pyridine with ether, pptn., filtration on suction, washing with ether until free from pyridine, drying over P2O5, elem. anal.;	A n/a B 84%

Di-sec-butylamin (626-23-3) + Cycloundecan-carbonsaeurechlorid (83224-26-4) → Cycloundecanecarboxylic acid di-sec-butyl-amide (91424-67-8)

Conditions	Yield
With triethylamine	83.37%

tetrachlorosilane (10026-04-7, 53609-55-5) + Di-sec-butylamin (626-23-3) → Trichlor(di-sek-butylamino)silan (73459-91-3)

Conditions	Yield
In hexane Heating;	83%

Di-sec-butylamin (626-23-3) + 4-cyclohexylbutyryl chloride (4441-67-2) → N,N-Di-sec-butyl-4-cyclohexyl-butyramide (91424-57-6)

Conditions	Yield
With triethylamine	83%

Di-sec-butylamin (626-23-3) + boron tribromide (10294-33-4) → dibromo(di-s-butylamino)borane (189264-87-7)

Conditions	Yield
With NEt3 In tetrachloromethane byproducts: [Et3NH]Br; N2-atmosphere; stirring (0°C, 2 h, refluxing, 4 h); filtering, evapn. (reduced pressure), distg.; elem. anal.;	81.1%

Di-sec-butylamin (626-23-3) + 4-bromo-o-xylene (583-71-1) → Di-sec-butyl-(3,4-dimethyl-phenyl)-amine (105336-44-5)

Conditions	Yield
With potassium amide for 5h; Heating;	81%

Di-sec-butylamin (626-23-3) + diglycolyl chloride (21062-20-4) → C20H40N2O3

Conditions	Yield
With sodium hydroxide In diethyl ether; water at 0 - 5℃; for 2.5h; Schotten-Baumann Reaction;	80%

1,2,3,4-tetrahydroquinoxaline (3476-89-9) + Di-sec-butylamin (626-23-3) → N2,N2,N6,N6-tetra-sec-butylquinoxaline-2,6-diamine

Conditions	Yield
With pyridine; N-hydroxyphthalimide; oxygen; copper dichloride In N,N-dimethyl-formamide at 30℃; for 2h; chemoselective reaction;	80%

Di-sec-butylamin (626-23-3) + perfluorobutanesulfonyl azide (65245-26-3) + phenylacetylene (536-74-3) → N,N-diisobutyl-N'-[(nonafluorobutyl)sulfonyl]-2-phenylacetamidine (1304126-63-3)

Conditions	Yield
With copper(l) iodide In tetrahydrofuran at 20℃; Inert atmosphere;	79%

Di-sec-butylamin (626-23-3) + 3-(1-(2-bromoacetyl)-5-(2-(trifluoromethyl)phenyl)-4,5-dihydro-1H-pyrazol-3-yl)-2H-chromen-2-one → C29H32F3N3O3

Conditions	Yield
With piperazine In acetone at 40 - 50℃;	79%

Di-sec-butylamin (626-23-3) + <2,6-bis(1-methylethyl)phenoxy>sulfonyl isocyanate (73748-46-6) → 2,6-bis(1-methylethyl)phenyl [(bis(1-methylpropyl)amino)carbonyl]sulfamate

Conditions	Yield
In diethyl ether for 16h; Ambient temperature;	78%

Di-sec-butylamin (626-23-3) + 3-cyclohexylpropionyl chloride (39098-75-4) → N,N-Di-sec-butyl-3-cyclohexyl-propionamide (91424-53-2)

Conditions	Yield
With triethylamine	77.6%

oxirane (75-21-8) + Di-sec-butylamin (626-23-3) → 2-di-sec-butylamino-ethanol (4535-71-1)

Conditions	Yield
In methanol at 40℃; for 65h;	77%
at 100℃;

Di-sec-butylamin (626-23-3) → N-Nitroso-di-sec-butylamin (5350-17-4)

Conditions	Yield
Stage #1: Di-sec-butylamin With n-butyllithium In tetrahydrofuran Metallation; Stage #2: With nitrogen(II) oxide In tetrahydrofuran at -78℃; Nitrosation;	76%

Di-sec-butylamin (626-23-3) + 2-(5,7-diethyl-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyrimidin-3-yl)acetic acid → N,N-di-sec-butyl-2-(5,7-diethyl-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyrimidin-3-yl)acetamide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 150℃; for 0.75h; Microwave irradiation;	76%

Di-sec-butylamin (626-23-3) + hydrocinnamic acid chloride (645-45-4) → N,N-Di-sec-butyl-3-phenyl-propionamide (91424-74-7)

Conditions	Yield
With triethylamine	75%

Di-sec-butylamin (626-23-3) + [(PPh3)2Pd(η(3)-CH2CCPh)]OSO2C6H4CH3 (173539-36-1) → (PPh3)2Pd(η3-CH2C(N(sec-Bu)2)CHPh)TOf (539848-28-7)

Conditions	Yield
In dichloromethane amine was added to stirred soln. of Pd-complex in CH2Cl2 at room temp. under Ar, stirred for 10 min; solvent was removed under reduced pressure, washed with hexane, dried under vac. for several d;	75%

Di-sec-butylamin (626-23-3) + Cyclododecancarbonsaeurechlorid (92157-95-4) → Cyclododecanecarboxylic acid di-sec-butyl-amide (91424-69-0)

Conditions	Yield
With triethylamine	73.13%

Upstream product

• 96-29-7 ethyl methyl ketone oxime 
• 33966-50-6 SEC-BUTYLAMINE 
• 78-76-2 s-butyl bromide 
• 1129-62-0 butan-2-one phenylhydrazone 
• 78-93-3 butanone 
• 106-98-9 1-butylene 
• 64-17-5 ethanol 
• 14753-38-9 sec. butyl magnesium iodide 
• 671795-46-3 sec-butylmagnesium bromide 
• 78-92-2 iso-butanol 
• 513-49-5 (S)-2-aminobutane 
• 38836-40-7 N-sec-butylidene-sec-butylamine 
• 53463-31-3 N,N-Di-sek.-butyl-N'-phenyl-harnstoff 
• 100-61-8 N-methylaniline 

Downstream Products

• 53463-25-5 dichloro-acetic acid di-sec-butylamide 
• 102599-90-6 di-sec-butyl-amidophosphoric acid diphenyl ester 
• 53463-38-0 N,N-Di-sec-butyl-2-chloro-2-phenyl-acetamide 
• 53463-60-8 N,N-Di-sec-butyl-2-(4-chloro-phenyl)-acetamide 
• 53463-32-4 1,1-Di-sec-butyl-3-(3-chloro-phenyl)-urea 
• 573-56-8 2,6-dinitrophenol 
• 5350-17-4 N-Nitroso-di-sec-butylamin 
• 27922-74-3 3-chloro,4-methyl-N,N-di-sec.butyl-benzamide 
• 83491-91-2 di-s-butylaminodimethylaminophenylborane 
• 539848-02-7 (PPh3)2Pt(η3-CH2C(N(sec-Bu)2)CHPh)TOf 
• 67141-62-2 N,N-Di-sec-butyl-2-(2,4-dichloro-phenoxy)-acetamide 
• 53463-57-3 Octanoic acid di-sec-butyl-amide 
• 53598-65-5 1,1-Di-sec-butyl-3-(3,4-dichloro-phenyl)-urea 
• 32322-33-1 N,N-di-sec-butyl-2-chloro-acetamide 

Relevant articles and documents

An improved and one-pot procedure to the synthesis of symmetric amines by domino reactions of 5-methyl-1,3,4-thiadiazole-2-amine, a new nitrogen atom donor, and alkyl halides

Abstract: A new one-pot method has been introduced in this work for the synthesis of symmetrical primary, secondary, and tertiary alkyl amines from alkyl halides and 5-methyl-1,3,4-thiadiazole-2-amine as a nitrogen-transfer reagent. In this method, all three types of amines have been successfully prepared after changing the ratio of substrates and base control. In addition to the introduction of a new nitrogen-transfer reagent, other important features of this work include normal atmospheric conditions and excellent yields under mild reaction conditions.

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