[ CAS No. 109-54-6 ] {[proInfo.proName]}

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Quality Control of [ 109-54-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 109-54-6 ]

SDS Specification

Alternatived Products of [ 109-54-6 ]

Product Citations

Compounds with Chelating 3-Dimethylamino-1-propyl Ligands as Chemical Vapor Deposition Precursors. Synthesis and Characterization of M [(CH2) 3NMe2] 2 Complexes of Nickel (II), Palladium (II), and Platinum (II)

Lastowski, R Joseph ; Flores, Vincent J ; Souqui, Laurent , et al. Organometallics,2024,43(20):2548-2556. DOI: 10.1021/acs.organomet.4c00186

Abstract: We describe the synthesis and characterization of three new square-planar compounds of stoichiometry M-[(CH2)3NMe2]2, where M = Ni, Pd, or Pt, each of which contains two chelating 3-dimethylamino-1-propyl ligands. The nickel(II) and palladium(II) compounds decompose above -78 and 0 °C, respectively, but the platinum(II) compound has a thermolysis onset temperature of 130 °C. The Pd and Pt complexes are dynamic in solution: they undergo ring inversion with small free energies of activation of ΔG? = 7.9 ± 0.1 and 8.3 ± 0.1 kcal mol-1, respectively, at 298 K. The Pt complex sublimes at 40 °C and 5 mTorr. In benzene solution, the Pt compound thermolyzes primarily through β-hydrogen elimination; 80 ± 10% of the hydrogen atoms and 75 ± 5% of the carbon atoms from the precursor can be accounted for in the byproducts. The thermolysis of the Pt complex in C6D6 follows first-order kinetics, with an activation free energy ΔG? of 29.9 ± 0.1 kcal mol?1 at 110 °C. Under CVD conditions, thin films grown of the Pt complex at 200 °C contain nanocrystalline Pt; analysis of the film growth byproducts suggest that the main decomposition pathway involves β-hydrogen elimination and reductive elimination steps, as seen in solution.

Purchased from AmBeed: 109-54-6

Product Details of [ 109-54-6 ]

CAS No. :	109-54-6	MDL No. :	MFCD00044496
Formula :	C₅H₁₂ClN	Boiling Point :	-
Linear Structure Formula :	(CH₃)₂N(CH₂)₃Cl	InChI Key :	NYYRRBOMNHUCLB-UHFFFAOYSA-N
M.W :	121.61	Pubchem ID :	66960
Synonyms :		Chemical Name :	3-Chloro-N,N-dimethylpropan-1-amine

Calculated chemistry of [ 109-54-6 ] Expand+

Physicochemical Properties

Num. heavy atoms :	7
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	3
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	33.84
TPSA :	3.24 ?2

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.18 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.04
Log Po/w (XLOGP3) :	1.21
Log Po/w (WLOGP) :	1.18
Log Po/w (MLOGP) :	1.53
Log Po/w (SILICOS-IT) :	0.87
Consensus Log Po/w :	1.37

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.16
Solubility :	8.45 mg/ml ; 0.0695 mol/l
Class :	Very soluble
Log S (Ali) :	-0.87
Solubility :	16.2 mg/ml ; 0.133 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.77
Solubility :	2.05 mg/ml ; 0.0168 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.34

Safety of [ 109-54-6 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P422-P411-P280-P305+P351+P338	UN#:
Hazard Statements:	H317-H319	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 109-54-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 109-54-6 ]
Downstream synthetic route of [ 109-54-6 ]

[ 109-54-6 ] Synthesis Path-Upstream 1~1

1
[ 109-54-6 ]
[ 103146-26-5 ]

Yield	Reaction Conditions	Operation in experiment
76.9%	Stage #1: With iodine; magnesium In 2-methyltetrahydrofuran at 60℃; for 4.83333 h; Inert atmosphere Stage #2: at -20℃; for 17.6167 h; Inert atmosphere Stage #3: With hydrogen bromide In 2-methyltetrahydrofuran at 3℃; for 1 h;	Example 3 Preparation of N,N-dimethyl-3-chloromagnesiopropylamine Grignard reagent 2-methyl tetrahydrofuran as solvent: Reaction process: At room temperature, Mg (7.28 g, 300 mmol) and iodine granules (0.506 g, 2 mmol) were suspended in anhydrous 2-methyltetrahydrofuran (80 mL, moisture content: 0.016percent), the reaction mixture was purged with nitrogen for 6 times. The reaction mixture was heated to 60 deg. C and stirred for 15min, the mixture was orange-red. 3-chloro-N, N-dimethylpropylamine (CPA) (24.32 g, 200 mmol) was dissolved in anhydrous 2-methyltetrahydrofuran (120 mL) was added dropwise to the above reaction mixture, reaction liquid from milky white to gray-green, 110min dropwise additon was finished, reaction at 60 ° C for 3 h, the solution of N,N-dimethyl-3-chloromagnesiopropylamine Grignard reagent in 2-methyltetrahydrofuran was cooled to room temperature and was directly used in the next reaction. Example 4 Preparation of 4-(4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile hydrobromide 2-methyl tetrahydrofuran as solvent: Reaction process: To a solution of the Grignard reagent of formula (III) (200 mL, 200 mmol) in anhydrous 2-methyltetrahydrofuran (541 mL) was added dropwise a solution of 2-methyltetrahydrofuran (541 mL) of formula (II) (54.30 g, 151.50 mmol), the solution was added dropwise over 97 min and the reaction mixture was stirred at -20 ° C for 16 h under nitrogen. Reaction post-treatment: Samples were quenched with saturated NH4Cl solution, and 2-methyltetrahydrofuran was analyzed by HPLC. The reaction mixture was allowed to warm to 0 ° C, and a saturated NH4Cl solution (120 mL) was added dropwise to the reaction mixture to quench the reaction mixture. The temperature of the reaction solution was maintained at 10 ° C or less, the white viscous solid was removed by suction filtration, the filtrate was cooled to 3 ° C and hydrogen bromide (30.30 g, 48percent, 179.70 mmol) was added dropwise to the filtrate, the reaction mixture was stirred at 3 ° C for 1 hour. The filtrate was concentrated under reduced pressure to remove 2-methyltetrahydrofuran. The reaction mixture was stirred at room temperature with CH2Cl2 (500 mL) and H2O (250 mL). The reaction mixture was cooled to room temperature, was added to the mixture, a white solid precipitated from the mixture, the reaction mixture was stirred at 15 ° C for 6 h, filtered, the white filter cake was washed with CH2Cl2 (3 x 80 mL) and dried in vacuo at 60 ° C for 16 h to give a white solid (49.33 g, yield: 76.9percent, based on 5-cyanophthalocyanine).

Reference： [1] Patent: CN105294496, 2016, A, . Location in patent: Paragraph 0120-0125; 0141- 0147; 0155-0167

[ 109-54-6 ] Synthesis Path-Downstream 1~4

1
[ 1198-97-6 ]
[ 144-62-7 ]
[ 109-54-6 ]
1-(3-dimethylaminopropyl)-4-phenyl-2-pyrrolidinone oxalate [ No CAS ]

Reference： [1]Pharmaceutical Chemistry Journal,1996,vol. 30,p. 222 - 226

2
[ 55453-87-7 ]
[ 109-54-6 ]
[ 140462-76-6 ]

Yield	Reaction Conditions	Operation in experiment
		Example 14: Preparation of (Z)-ll-[3-(dimehylamino)propylidene]-6,ll- dihydrodibenz[b,e] oxepin-2-acetic acid hydrochlorideIodine (0.5 g) was added to a mixture of magnesium (43 g) and tetrahydrofuran (150 ml) under nitrogen condition. Heated the reaction mixture to reflux temperature. 3- dimethyl amino propyl chloride (5 ml) followed by 1,2-dibromo ethane (2 g) were added to the reaction mixture at same reflux temperature. A solution of 3 -dimethyl amino propyl chloride (225 g) in tetrahydrofuran (200 ml) was added drop wise to the reaction mixture at reflux temperature and stirred for 1 hour at the same temperature. Cooled the reaction mixture to 25-30°C, further cooled to 5-10°C. A solution of l l-oxo-6,11- dihydrobenz[b,e]oxepin-2-acetic acid (50 g) in tetrahydrofuran (150 ml) was added to the reaction mixture slowly at 5-10°C and stirred for 45 minutes at 5-10°C. Raised the temperature of the reaction mixture to 25-30°C and stirred the reaction mixture for 5 hours at same temperature. After completion of the reaction, the reaction mixture was quenched with aqueous acetic acid. Aqueous hydrochloric acid [hydrochloric acid (300 ml) in water (100 ml)] was added to the reaction mixture at a temperature below 25 °C and stirred for 10 minutes at 25-30°C. Toluene was added to the reaction mixture and stirred for 10 minutes. Both the toluene and aqueous layers were separated and the aqueous layer was washed with toluene. Both the toluene layers were combined and washed with hydrochloric acid. Both the aqueous layer and hydrochloric acid layers were combined. Heated the aqueous layer to 90-95 °C and stirred for 24 hours at same temperature Cooled the reaction mixture to 25-30°C and dichloromethane was added to the reaction mixture. Stirred the reaction mixture for 15 minutes at 25-30°C. Both the organic and aqueous layers were separated and the aqueous layer was extracted with dichloromethane. Both the dichloromethane layers were combined and then dried with sodium sulfate. Distilled off the solvent completely under reduced pressure and co- distilled with acetone. Acetone was added to the reaction mixture and stirred for 45 minutes at 25-30°C. Filtered the precipitated solid, washed with acetone and then dried to get the title compound.Yield: 30 grams; Purity by HPLC: 98.9percent (Z-isomer)

Reference： [1]Patent: WO2011/128911,2011,A2 .Location in patent: Page/Page column 22-23

3
[ 33893-89-9 ]
[ 109-54-6 ]
N,N-dimethyl-3-(5-(pyridin-2-yl)-1H-tetrazol-1-yl)propan-1-amine [ No CAS ]
N,N-dimethyl-3-(5-(pyridin-2-yl)-2H-tetrazol-2-yl)propan-1-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
26%; 26%		To the compound L (1 g, 6.8 mmol) dissolved in acetonitrile (30 mL) was added potassium carbonate (4.6 g, 34 mmol). The resulting solution was refluxed for 0.5 h and to hot solution was added 3-chloro-N,N-dimethylpropan-1-amine (3.1 g, 22 mmol). The reaction mixture was then stirred at reflux temperature for a further 24 h. After cooling,the solvent was removed under reduced pressure to afford a white precipitate, which was purified by column chromatography on silica gel (ethyl acetate:hexane by the ratio of 20:80) to give isomers L1 and L3. L2: White brown solid (0.55 g, yield 26 %). m.p. 72-76 C.Anal. calcd. for C11H16N6 (232.28): C, 56.88; H, 6.94; N, 36.18;1H NMR (CDCl3, 300 MHz): delta 8.71 (d, 1H, J = 4.5 Hz, pyr-H), 8.37 (d, 1H, J = 8.1 Hz, pyr-H), 7.91 (dt, 1H, J = 7.8, 1.8Hz, pyr-H), 7.45 (dd, 1H, J = 7.5, 5.1 Hz, pyr-H), 5.12 (t, 2H,J = 6.9 Hz, CH2N), 2.88 (t, 2H, J = 6.9 Hz, CH2), 2.42(p, 2H,J = 6.9 Hz, CH2), 2.29 (s, 6H, N(CH3)2) ppm. 13C NMR (CDCl3,60 MHz): delta 150.45 (CN4), 148.53, 144.66, 137.16, 123.15,122.24, 48.24 (CH2N4), 43.56 (CH2N-(CH3)2), 26.82, ppm. L4: White brown solid (0.55 g, yield 26 %). m.p. 66-68 C.Anal. calcd. for C11H16N6 (232.28): C, 56.88; H, 6.94; N, 36.18;1H NMR (CDCl3, 300 MHz): delta 8.65 (d, 1H, J = 4.5 Hz, pyr-H), 8.28 (d, 1H, J = 8.1 Hz, pyr-H), 7.87 (dt, 1H, J = 7.8, 1.8Hz, pyr-H), 7.34 (t, 1H, J = 7.5, 5.1 Hz, pyr-H), 5.06 (t, 2H,J = 6.9 Hz, CH2N), 2.82 (t, 2H, J = 6.9 Hz, CH2), 2.42(p, 2H,J = 6.9 Hz, CH2), 2.27 (s, 6H, N(CH3)2) ppm. 13C NMR (CDCl3,60 MHz): delta 151.35 (CN4), 149.44, 145.36, 138.08, 124.64,122.12, 49.54 (CH2N4), 44.34 (CH2N-(CH3)2), 26.82, ppm.

Reference： [1]Asian Journal of Chemistry,2015,vol. 27,p. 4405 - 4410

4
[ 39607-90-4 ]
[ 109-54-6 ]
[ 303-49-1 ]

Reference： [1]ChemCatChem,2018,vol. 10,p. 4346 - 4352

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Isomers

Technical Information

? Alkyl Halide Occurrence ? Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions ? Chan-Lam Coupling Reaction ? General Reactivity ? Grignard Reaction ? Heat of Combustion ? Hiyama Cross-Coupling Reaction ? Hydride Reductions ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Leuckart-Wallach Reaction ? Mannich Reaction ? Petasis Reaction ? Preparation of Amines ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Specialized Acylation Reagents-Vilsmeier Reagent ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Ugi Reaction

Historical Records

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H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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[ CAS No. 109-54-6 ] {[proInfo.proName]}

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[ 109-54-6 ] Synthesis Path-Upstream 1~1

[ 109-54-6 ] Synthesis Path-Downstream 1~4

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Aliphatic Chain Hydrocarbons

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