105-83-9

Basic information

• Product Name: 1,3-Propanediamine,N1-(3-aminopropyl)-N1-methyl-
• Synonyms: Dipropylamine, 3,3'-diamino-N-methyl-(6CI,7CI,8CI);(7-Amino-4-methyl-4-azaheptyl)amine;1,7-Diamino-4-methyl-4-azaheptane;3,3'-Diamino-N-methyldipropylamine;4-Aza-4-methylheptane-1,7-diamine;5-Methyl-1,5,9-triazanonane;5-Methyldipropylenetriamine;Bis(3-aminopropyl)methylamine;Bis(w-aminopropyl)methylamine;Di(g-aminopropyl)methylamine;Methylbis(3-aminopropyl)amine;Methyliminobispropylamine;N,N'-Bis(3-aminopropyl)methylamine;N-(3-Aminopropyl)-N-methyl-1,3-propanediamine;N-Methyl-N,N-bis(3-aminopropyl)amine;N'-Methyl-3,3'-diaminodipropylamine
• CAS NO: 105-83-9
• Molecular Formula: C₇H₁₉N₃
• Molecular Weight: 145.25
• EINECS: 203-336-8
• Product Categories: Nitrogen Compounds;Organic Building Blocks;Polyamines;Pharmaceutical Raw Materials
• Mol File: 105-83-9.mol
• Article Data: 2

Chemical Properties

• Melting Point: -30--28°C
• Boiling Point: 252.9 °C at 760 mmHg
• Flash Point: 102.8 °C
• Appearance: /
• Density: 0.915 g/cm³
• Vapor Pressure: 6 mm Hg ( 110 °C)
• Refractive Index: n20/D 1.4725(lit.)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: Completely miscible in water
• PKA: pK1:6.32(＋3);pK2:9.19(＋2);pK3:10.33(＋1) (30°C)
• Water Solubility: 1000g/L at 20℃
• CAS DataBase Reference: 1,3-Propanediamine,N1-(3-aminopropyl)-N1-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Propanediamine,N1-(3-aminopropyl)-N1-methyl-(105-83-9)
• EPA Substance Registry System: 1,3-Propanediamine,N1-(3-aminopropyl)-N1-methyl-(105-83-9)

Safety Data

• Hazard Codes: T
• Statements: 22-23/24-34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 2810 6.1/PG 2
• WGK Germany: 1
• RTECS: JL9625000
• HazardClass: 6.1(a)
• PackingGroup: II
• Hazardous Substances Data: 105-83-9(Hazardous Substances Data)

Usage

Uses

3,3′-Diamino-N-methyldipropylamine was used in the synthesis of:new bischromone derivatives, potential anticancer drugspolyamine derivatives containing dimeric quinolone, cinnoline and phthalimide moieties3-(2,4-dinitroanilino)-3′-amino-N-methyldipropylamine

Flammability and Explosibility

Nonflammable

Safety Profile

Poison by inhalation and skincontact. Moderately toxic by ingestion. A skin and severeeye irritant. Combustible whenexposed to heat or flame. To fight fire, use foam, fog, drychemical. When heated to decomposition it emits toxicfumes of NOx.

Synthetic route

Bis(2-cyanoethyl)methylamine (1555-58-4) → 3,3'-Diamino-N-methyldipropylamine (105-83-9)

Conditions	Yield
With hydrogen; sodium hydroxide In ethanol at 90℃; under 15001.5 Torr; Autoclave; Green chemistry;	85%
With sodium; butan-1-ol
With ammonia; nickel at 100℃; under 73550.8 Torr; Hydrogenation;

Bis(2-cyanoethyl)methylamine (1555-58-4) → 1-methyl-[1,5]diazocane (4318-36-9) + 3,3'-Diamino-N-methyldipropylamine (105-83-9)

Conditions	Yield
With ammonia; nickel at 90 - 100℃; under 73550.8 Torr; Hydrogenation;

3,3'-Diamino-N-methyldipropylamine (105-83-9) + 1-methyl-4-nitro-2-trichloroacetylpyrrole (120122-47-6) → 1-methyl-N-[3-[methyl-[3-[(1-methyl-4-nitro-pyrrole-2-carbonyl)amino]propyl]amino]propyl]-4-nitro-pyrrole-2-carboxamide (158551-29-2)

Conditions	Yield
In tetrahydrofuran at 20℃;	100%

N-(Benzyloxycarbonyloxy)succinimide (13139-17-8) + 3,3'-Diamino-N-methyldipropylamine (105-83-9) → C23H31N3O4 (1307864-23-8)

Conditions	Yield
In chloroform at 20℃; for 16h;	100%
In chloroform at 20℃; for 16h;
In chloroform at 20℃; for 16h;

3,3'-Diamino-N-methyldipropylamine (105-83-9) + phenyl isothiocyanate (103-72-0) → C21H29N5S2 (1229624-20-7)

Conditions	Yield
In tetrahydrofuran at 20℃;	100%

3,3'-Diamino-N-methyldipropylamine (105-83-9) + 2-chloro-3-methyl-4-quinolinecarboxylic acid chloride (431078-96-5) → C29H31Cl2N5O2 (1620066-15-0)

Conditions	Yield
With triethylamine In chloroform at 20℃; for 48h;	98%

3,3'-Diamino-N-methyldipropylamine (105-83-9) + 3-(8-methoxypyrrolo[1,2-a]quinoxalin-4-yl)benzaldehyde → bis{N-[3-(8-methoxypyrrolo[1,2-a]quinoxalin-4-yl)benzylidene]-3-aminopropyl}methylamine

Conditions	Yield
In ethanol for 5h; Reflux;	98%

3,3'-Diamino-N-methyldipropylamine (105-83-9) + 2-(4-formylphenyl)-1,10-phenanthroline → bis{N-[4-(1,10-phenanthrolin-2-yl)benzylidene]-3-aminopropyl}methylamine

Conditions	Yield
In ethanol for 5h; Reflux;	98%

3,3'-Diamino-N-methyldipropylamine (105-83-9) + (1,1-dimethyl-2-phenylethyl) hydrogen benzene-1,2-dicarboxylate (170233-80-4) → C43H51N3O6

Conditions	Yield
With TEA; chloroformic acid ethyl ester In dichloromethane	97%

copper(II) perchlorate hexahydrate + 3,3'-Diamino-N-methyldipropylamine (105-83-9) + sodium nitrite (7632-00-0) → [Cu(3,3'-diamino-N-methyldipropylamine)(ONO)(H2O)]ClO4 (890850-35-8)

Conditions	Yield
In methanol soln. of Cu salt added to soln. of org. compd., hot soln. of NaNO2 addeddropwise, heated for 10 min; hot filtered, allowed to crystallize at room temp., filtered, washed with ether, air-dried; elem. anal.;	97%

ethanol (64-17-5) + 3,3'-Diamino-N-methyldipropylamine (105-83-9) + 1,2-bis(4-tert-butyl-2,6-diformylphenylsulfanyl)ethane (255367-21-6) → C40H68N6S2*0.5C2H6O

Conditions	Yield
Stage #1: ethanol; 3,3'-Diamino-N-methyldipropylamine; 1,2-bis(4-tert-butyl-2,6-diformylphenylsulfanyl)ethane In dichloromethane at 0 - 20℃; for 18h; Stage #2: With sodium tetrahydroborate at 20℃; for 4h;	97%

3,3'-Diamino-N-methyldipropylamine (105-83-9) + 4-(3-ethoxypyrrolo[1,2-a]quinoxalin-4-yl)benzaldehyde → bis{N-[4-(3-ethoxypyrrolo[1,2-a]quinoxalin-4-yl)benzylidene]-3-aminopropyl}methylamine

Conditions	Yield
In ethanol for 5h; Reflux;	97%

3,3'-Diamino-N-methyldipropylamine (105-83-9) + 3-(pyrrolo[1,2-a]quinoxalin-4-yl)benzaldehyde → bis{N-[3-(pyrrolo[1,2-a]quinoxalin-4-yl)benzylidene]-3-aminopropyl}methylamine

Conditions	Yield
In ethanol for 5h; Reflux;	97%

3,3'-Diamino-N-methyldipropylamine (105-83-9) + di-tert-butyl dicarbonate (24424-99-5) → N-(3-aminopropyl)-N-(3-tert-butyloxycarbonyl-aminopropyl)-N-methylamine (87530-14-1)

Conditions	Yield
In tetrahydrofuran	96%
In tetrahydrofuran	96%
In tetrahydrofuran	83%

3,3'-Diamino-N-methyldipropylamine (105-83-9) + (E,E)-5-(3,4,5-trimethoxyphenyl)-2,4-pentadienoic acid (28010-23-3) → N,N-bis[N-[5-(3,4,5-trimethoxyphenyl)penta-(2E,4E)-dienoyl]-3-aminopropyl]methylamine

Conditions	Yield
	96%

ammonium thiocyanate + copper(II) perchlorate hexahydrate + 3,3'-Diamino-N-methyldipropylamine (105-83-9) → [Cu2(3,3'-diamino-N-methyldipropylamine)2(μN,S-NCS)2](ClO4)2

Conditions	Yield
In methanol soln. of NH4CNS added dropwise to mixt. of soln. of Cu salt and of org. compd., heated for 5 min; hot filtered, allowed to crystallize at room temp., filtered, washed with ether, air-dried; elem. anal.;	96%

3,3'-Diamino-N-methyldipropylamine (105-83-9) + 4-(9-methoxypyrrolo[1,2-a]quinoxalin-4-yl)benzaldehyde → bis{N-[4-(9-methoxypyrrolo[1,2-a]quinoxalin-4-yl)benzylidene]-3-aminopropyl}methylamine

Conditions	Yield
In ethanol for 5h; Reflux;	96%

3,3'-Diamino-N-methyldipropylamine (105-83-9) + C19H14N2O2 → bis{N-[4-(7-methoxypyrrolo[1,2-a]quinoxalin-4-yl)benzylidene]-3-aminopropyl}methylamine

Conditions	Yield
In ethanol for 5h; Reflux;	96%

3,3'-Diamino-N-methyldipropylamine (105-83-9) + C19H14N2O2 → bis{N-[4-(8-methoxypyrrolo[1,2-a]quinoxalin-4-yl)benzylidene]-3-aminopropyl}methylamine

Conditions	Yield
In ethanol for 5h; Reflux;	96%

(E)-3-(5,6-dimethoxy-1,1-dimethyl-2-indenyl)-2-propenoic acid (203722-25-2) + 3,3'-Diamino-N-methyldipropylamine (105-83-9) → N,N-bis[N-[3-(5,6-dimethoxy-1,1-dimethyl-2-indenyl)prop-(2E)-enoyl]-3-aminopropyl]methylamine

Conditions	Yield
	95%

3,3'-Diamino-N-methyldipropylamine (105-83-9) + Co(OCHOC6H2Cl2)2 (49860-79-9) → Co((CH2)3NCHC6H2Cl2O)2NCH3 (38625-76-2)

Conditions	Yield
In methanol under N2 soln. was refluxed for 30 min; soln. was concd. in vac., allowed to stand at room temp., prisms were collected by suction, washed with methanol, dried in vac. dessicator; elem. anal.;	95%

3,3'-Diamino-N-methyldipropylamine (105-83-9) + molybdenum hexacarbonyl (13939-06-5, 199620-15-0) → fac-[(H2N(CH2)3NMe(CH2)3NH2)Mo(CO)3] (161334-73-2)

Conditions	Yield
In dibutyl ether N2-atmosphere; slight excess metal carbonyl, refluxing for 2 h (returning sublimed hexacarbonyl into reaction vessel); cooling to room temp., collection of ppt., washing (hexane), drying (vac., 50°C);	95%

3,3'-Diamino-N-methyldipropylamine (105-83-9) + C17H13ClNO2(1+)*I(1-) → 11-((3-((3-aminopropyl)(methyl)amino)propyl)amino)-7-methoxy-5-methylbenzofuro[3,2-b]quinolin-5-ium iodide (1587729-29-0)

Conditions	Yield
at 120℃; for 0.5h;	95%
In 2-methoxy-ethanol at 120℃; for 0.5h;	1.36 g

3,3'-Diamino-N-methyldipropylamine (105-83-9) + 3,5-di-tert-butyl-2-hydroxybenzaldehyde (37942-07-7) → N,N′-bis(3,5-di-tert-butyl-2-hydroxybenzyliden)-1,7-diamino-4-methyl-4-azaheptane

Conditions	Yield
In methanol at 20℃; for 2h; Inert atmosphere; Schlenk technique;	94%
In ethanol for 1h; Heating;
In ethanol Reflux;

3,3'-Diamino-N-methyldipropylamine (105-83-9) + 3,4-diethoxy-3-cyclobuten-1,2-dione (5231-87-8) → 3,3'-[N,N'-[(methylimino)di-3,1-propanediyldiimino]]bis(4-ethoxy-3-cyclobutene-1,2-dione) (679427-49-7)

Conditions	Yield
In diethyl ether at 20℃; for 12h;	94%
In diethyl ether at 20℃;	74%
In diethyl ether
In diethyl ether at 20℃;
In diethyl ether at 20℃; for 12h; Inert atmosphere;

3,3'-Diamino-N-methyldipropylamine (105-83-9) → C33H35N3O6

Conditions	Yield
In ethanol	94%

1-chloro-7-methoxy-4-nitro-10H-acridin-9-one (21814-48-2) + 3,3'-Diamino-N-methyldipropylamine (105-83-9) → 1,1'-<(methylimino)bis(3,1-propanediylimino)>bis<7-methoxy-4-nitro-9(10H)-acridinone>

Conditions	Yield
With triethylamine In dimethyl sulfoxide at 80℃; for 3h;	93%

3,3'-Diamino-N-methyldipropylamine (105-83-9) + 3,6-dichloro-O-anisic acid (1918-00-9) → C7H19N3*2C8H6Cl2O3

Conditions	Yield
In methanol at 25℃; under 759.826 Torr;	92%

3,3'-Diamino-N-methyldipropylamine (105-83-9) + mitomycin A (4055-39-4) → C37H49N9O10

Conditions	Yield
In methanol; N,N-dimethyl-formamide at 20℃; for 4h;	91%

sodium azide + copper(II) perchlorate hexahydrate + 3,3'-Diamino-N-methyldipropylamine (105-83-9) → [Cu2(μ1,3-N3)2(methyldipropylenetriamine)2](ClO4)2

Conditions	Yield
In methanol hot suspn. of NaN3 in methanol added dropwise to soln. of Cu salt and triamine in methanol; soln. quickly filtered, filtrate heated in steam bath for 5 min, soln. kept at room temp. for 1 h; crystals filtered off; washed with ether; air dried; elem. anal.;	91%
In water aq. soln. of NaN3 added dropwise to soln. of Cu salt and triamine in H2O; stirred for 10 min, left to crystallize at room temp.; crystals filtered off; washed with EtOH and ether; air dried; further crop of crystals from mother liquor which was kept at room temp. for 4 d;	86%

2,6-Bis(2-formylphenoxymethyl)pyridine (66433-95-2) + holmium(III) nitrate hydrate + 3,3'-Diamino-N-methyldipropylamine (105-83-9) → [Ho(15-methyl-3.27-dioxa-11.15.19.33-tetraazatetracyclo[27.3.1.O(4.9).O(21,26)]tritiaconta-1(32).4(9).5.7.10.19.21(26).22.24.29(33).30-nonaene)][NO3]3*4H2O

Conditions	Yield
In not given 2,6-bis(2-formylphenoxymethyl)pyridine and Ho(NO3)3*nH2O were dissolved in hot MeOH or EtOH, soln. N,N-bis(3-aminopropyl)methylamine in MeOH or EtOH was added dropwise and refluxed for 3-4 h; react. mixt. was allowed to cool to room temp. and concd., Et2O was added, ppt. was filtered and dried in vacuo; elem. anal.;	91%

sodium hexanitrocobaltate(III) + 3,3'-Diamino-N-methyldipropylamine (105-83-9) → [Co(5-methyl-1,5,9-triazanonane)(NO2)3] (312712-70-2)

Conditions	Yield
In water aq. soln. of ligand was added dropwise to hot aq. soln. of Co complex; filtered; heated on steam bath with stirring for 15 min; after 2 h filtered; washed (H2O, MeOH, ether); air-dried; elem. anal.;	91%

Upstream product

• 1555-58-4 Bis(2-cyanoethyl)methylamine 

Downstream Products

• 152273-34-2 (4,6-(MeO)2-SMDPTH₂) 
• 132953-33-4 abaMedpt 
• 95690-83-8 N,N-bis[3-(p-tolylsulfonyl)aminopropyl]methylamine 
• 416850-41-4 N-{3-[(3-amino-propyl)-methyl-amino]-propyl}-2-{4-[2'-(4-hydroxy-phenyl)-3H,3'H-[2,5']bibenzoimidazolyl-5-yl]-piperazin-1-yl}-acetamide 
• 956487-30-2 C₅₉H₅₉F₆N₉O₈ 
• 15391-24-9 N,N'-(3,3'-bis(propyl)methylamine)bis(salicylideneiminato)cobalt(II) 
• 956486-48-9 C₄₇H₃₉F₆N₉O₄ 
• 1186017-44-6 C₅₅H₆₉N₂₃O₉ 

Relevant articles and documents

An efficient synthesis of N,N,N′,N′,N″-pentamethyldipropylenetriamine

N,N,N′,N′,N″-Pentamethyldipropylenetriamine (PMDPTA) has for a long time been employed as an efficient catalyst in the production of polyurethane materials. A green and effective synthetic route to PMDPTA was successfully established from experiments described in this paper. PMDPTA was obtained from methylamine, acrylonitrile and formaldehyde via a Michael addition, catalytic hydrogenation and methylation in 65% overall yield. Furthermore, methanol was employed as the only solvent in all of the three steps, resulting in the convenient recovery of methanol. This route is thus suitable for industrial production.