15521-18-3

Basic information

• Product Name: DL-2-DIMETHYLAMINO-1-PROPANOL
• Synonyms: DL-2-DIMETHYLAMINO-1-PROPANOL;2-(dimethylamino)propan-1-ol;2-(Dimethylamino)-1-propanol
• CAS NO: 15521-18-3
• Molecular Formula: C₅H₁₃NO
• Molecular Weight: 103.16
• EINECS: 239-558-7
• Mol File: 15521-18-3.mol
• Article Data: 2

Chemical Properties

• Melting Point: 29.84°C (estimate)
• Boiling Point: 193.43°C (rough estimate)
• Flash Point: 32.1 °C
• Appearance: /
• Density: 0.8820
• Vapor Pressure: 3.62mmHg at 25°C
• Refractive Index: 1.4435 (estimate)
• PKA: 14.69±0.10(Predicted)
• CAS DataBase Reference: DL-2-DIMETHYLAMINO-1-PROPANOL(CAS DataBase Reference)
• NIST Chemistry Reference: DL-2-DIMETHYLAMINO-1-PROPANOL(15521-18-3)
• EPA Substance Registry System: DL-2-DIMETHYLAMINO-1-PROPANOL(15521-18-3)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 15521-18-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C5H13NO/c1-5(4-7)6(2)3/h5,7H,4H2,1-3H3/t5-/m0/s1

Synthetic route

formaldehyd (50-00-0) + 2-Amino-1-propanol (6168-72-5) → 2-(dimethylamino)propan-1-ol (15521-18-3)

Conditions	Yield
With formic acid
With ethanol; water; sodium acetate Hydrieren des Reaktionsgemisches in Gegenwart von Raney-Nickel bei 65grad/70 at;
With formic acid

2-chloro-1-dimethylaminopropane (108-14-5) → 2-(dimethylamino)propan-1-ol (15521-18-3)

Conditions	Yield
With silver(l) oxide

ethyl 2-(N,N-dimethylamino)-propionate (82614-49-1) → 2-(dimethylamino)propan-1-ol (15521-18-3)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether

dimethyl amine (124-40-3) + 2-Bromopropionic acid (598-72-1) → 2-(dimethylamino)propan-1-ol (15521-18-3)

Conditions	Yield
(i) H2O, (ii) EtOH, HCl, (iii) LiAlH4, Et2O; Multistep reaction;

dimethyl amine (124-40-3) + Ethyl 2-bromopropionate (535-11-5, 41978-69-2) → 2-(dimethylamino)propan-1-ol (15521-18-3)

Conditions	Yield
(i) Et2O, (ii) LiAlH4; Multistep reaction;

C59H104N2O15 → 2-(dimethylamino)propan-1-ol (15521-18-3) + 2-dimethylamino-3-methoxypropanol + (2E,4E,14E,20E)-(23S,24R,25S,26S,29R,30S,31R,32R)-13,19,34,34-Tetramethoxy-8,10,14,17,24,26,30,32-octamethyl-tetratriaconta-2,4,14,20-tetraene-1,7,9,23,25,29,31-heptaol

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether at 23℃;

α-dimethylamino-propionic acid ethyl ester → 2-(dimethylamino)propan-1-ol (15521-18-3)

Conditions	Yield
With ethanol; sodium

2-chloro-1-dimethylaminopropane (108-14-5) + moist silver oxide → 2-(dimethylamino)propan-1-ol (15521-18-3)

sodium thiocyanide (540-72-7) + copper(II) acetate monohydrate (6046-93-1) + 2-(dimethylamino)propan-1-ol (15521-18-3) → [Cu((CH3)3NCHCH2O)(NCS)]2 (59451-06-8, 500314-74-9)

Conditions	Yield
In methanol MeOH soln. of NaNCS was added to MeOH soln. of Cu(OAc)2*H2O and ligand, allowed to stand at 25°C for several ds; filtered, dried in vacuo; elem. anal.;	90%

5-(2-Chloro-phenyl)-2-methylsulfonyl-pyrimidine-4-carboxylic acid (3,5-bis-trifluoromethyl-benzyl)-methyl-amide (311334-77-7) + 2-(dimethylamino)propan-1-ol (15521-18-3) → 5-(2-chloro-phenyl)-2-(3-dimethylamino-propoxy)-pyrimidine-4-carboxylic acid (3,5-bis-trifluoromethyl-benzyl)-methyl-amide (311334-83-5)

Conditions	Yield
With caesium carbonate In acetonitrile for 16h;	77%

2-(dimethylamino)propan-1-ol (15521-18-3) → N,N-dimethyl acetamide (127-19-5)

Conditions	Yield
With potassium hydroxide; air In diethyl ether at 20℃; for 90h;	73%

diphenylacetic acid chloride (1871-76-7) + 2-(dimethylamino)propan-1-ol (15521-18-3) → diphenyl-acetic acid-(2-dimethylamino-propyl ester)

Conditions	Yield
With benzene

3,3-diphenylpropanoyl chloride (37089-77-3) + 2-(dimethylamino)propan-1-ol (15521-18-3) → 3,3-diphenyl-propionic acid-(2-dimethylamino-propyl ester)

N,N-dicyclohexylcarbamoyl chloride (6292-88-2) + 2-(dimethylamino)propan-1-ol (15521-18-3) → dicyclohexyl-carbamic acid-(2-dimethylamino-propyl ester)

Conditions	Yield
With toluene

2-(dimethylamino)propan-1-ol (15521-18-3) + acetic anhydride (108-24-7) → (β-acetoxy-isopropyl)-trimethyl-ammonium; iodide (26290-68-6)

Conditions	Yield
Umsetzung des Reaktionsprodukts mit Methyljodid;

2-(dimethylamino)propan-1-ol (15521-18-3) + succinoyl dichloride (543-20-4) → succinic acid bis-(2-dimethylamino-propyl ester) (96434-49-0)

Conditions	Yield
With hydrogenchloride; chloroform

2-(dimethylamino)propan-1-ol (15521-18-3) + acryloyl chloride (814-68-6) → acrylic acid-(2-dimethylamino-propyl ester) (99969-68-3)

Conditions	Yield
With benzene

2-(dimethylamino)propan-1-ol (15521-18-3) + methyl iodide (74-88-4) → (β-hydroxy-isopropyl)-trimethyl-ammonium; hydroxide (3645-02-1)

Conditions	Yield
With ethanol und nachfolgendem Behandeln des entstandenen Jodids mit Silberoxyd;

2-(dimethylamino)propan-1-ol (15521-18-3) + methyl iodide (74-88-4) → (β-hydroxy-isopropyl)-trimethyl-ammonium; iodide (4188-22-1)

Conditions	Yield
With ethanol

2-(dimethylamino)propan-1-ol (15521-18-3) → 2-(dimethyl-amino)-1-methylethylchloride hydrochloride (17256-39-2)

Conditions	Yield
With thionyl chloride; chloroform
With thionyl chloride; benzene zuletzt bei Siedepemperatur;
With thionyl chloride In chloroform at -60 - 60℃;

2-(dimethylamino)propan-1-ol (15521-18-3) → 2-chloro-1-dimethylaminopropane (108-14-5)

Conditions	Yield
With thionyl chloride; benzene

styrene oxide (96-09-3) + 2-(dimethylamino)propan-1-ol (15521-18-3) → 2-(2-Dimethylamino-propyloxy)-1-phenyl-ethanol-(1) (93309-65-0)

Conditions	Yield
(i) Na, (ii) /BRN= 108582/; Multistep reaction;

methyl benzilate (76-89-1) + 2-(dimethylamino)propan-1-ol (15521-18-3) → benzilic acid-(2-dimethylamino-propyl ester) (94914-83-7)

Conditions	Yield
With sodium In benzene

ethyl 2-cyclohexyl-2-hydroxy-2-phenylacetate (31197-69-0) + 2-(dimethylamino)propan-1-ol (15521-18-3) → Cyclohexyl-phenyl-glykolsaeure-<2-dimethylamino-propylester> (94439-61-9)

Conditions	Yield
With sodium In benzene

2-(dimethylamino)propan-1-ol (15521-18-3) + ethyl iodide (75-03-6) + succinoyl dichloride (543-20-4) → C18H38N2O4(2+)*2I(1-)

Conditions	Yield
(i) HCl, CHCl3, (ii) /BRN= 505934/, EtOH; Multistep reaction;

2-(dimethylamino)propan-1-ol (15521-18-3) + ethyl iodide (75-03-6) + succinoyl dichloride (543-20-4) → C18H38N2O4(2+)*2I(1-)

Conditions	Yield
(i) HCl, CHCl3, (ii) /BRN= 505934/, EtOH; Multistep reaction;

2-(dimethylamino)propan-1-ol (15521-18-3) + allyl bromide (106-95-6) → 2-Dimethylamino-1-allyloxy-propan (13388-32-4)

Conditions	Yield
(i) NaH, toluene, (ii) /BRN= 605308/; Multistep reaction;

2-(dimethylamino)propan-1-ol (15521-18-3) + ethyl vinyl ether (109-92-2) → Dimethyl-(1-methyl-2-vinyloxy-ethyl)-amine (59276-18-5)

Conditions	Yield
With mercury(II) diacetate Heating;

2-(dimethylamino)propan-1-ol (15521-18-3) + 4-chlorobenzoyl chloride (586-75-4) → 4-Bromo-benzoic acid 2-dimethylamino-propyl ester

Conditions	Yield
With pyridine at 23℃;

2-(dimethylamino)propan-1-ol (15521-18-3) + N,N-Dimethylcarbamoyl chloride (79-44-7) → (RS)-2-dimethylamino-1-propyl N,N-dimethylcarbamate

Conditions	Yield
With sodium hydride In toluene for 24h; Ambient temperature; Yield given;

Upstream product

• 108-14-5 2-chloro-1-dimethylaminopropane 
• 124-40-3 dimethyl amine 
• 598-72-1 2-Bromopropionic acid 
• 535-11-5 Ethyl 2-bromopropionate 
• 82614-49-1 ethyl 2-(N,N-dimethylamino)-propionate 
• 50-00-0 formaldehyd 
• 6168-72-5 2-Amino-1-propanol 

Downstream Products

• 26290-68-6 1-Acetoxy-2-dimethylaminopropan-methiodid 
• 4188-22-1 (β-hydroxy-isopropyl)-trimethyl-ammonium; iodide 
• 17256-39-2 2-(dimethyl-amino)-1-methylethylchloride hydrochloride 
• 108-14-5 2-chloro-1-dimethylaminopropane 
• 94914-83-7 benzilic acid-(2-dimethylamino-propyl ester) 
• 94439-61-9 Cyclohexyl-phenyl-glykolsaeure-<2-dimethylamino-propylester> 
• 127-19-5 N,N-dimethyl acetamide 
• 109478-13-9 3-(ethyl-dimethyl-ammonio)-propionic acid-[2-(ethyl-dimethyl-ammonio)-propylester]; diiodide 
• 311334-83-5 5-(2-chloro-phenyl)-2-(3-dimethylamino-propoxy)-pyrimidine-4-carboxylic acid (3,5-bis-trifluoromethyl-benzyl)-methyl-amide 
• 93309-65-0 2-(2-Dimethylamino-propyloxy)-1-phenyl-ethanol-(1) 

Relevant articles and documents

Futher Studies on Aplyronine A, an Antitumor Substance Isolated from the Sea Hare Aplysia kurodai

By a series of reactions aplyronine A (1) an antitumor substance of marine origin was transformed into six fragments, and their structures were characterized by spectroscopic methods.Relative stereochemistry of four contiguous chiral centers (C29-C32) in 1 was established and that of three contiguous chiral centers (C23-C25) in 1 was deduced on the basis of the 1H NMR spectral analysis of the fragment 8 and the derived acetonide 9, respectively.