Benzenemethanol,α-[2-(dimethylamino)ethyl]- supplier

Name
3-dimethylamino-1-phenyl-propan-1-ol
EINECS
CAS No. 5554-64-3
Article Data37
CAS DataBase
Density 1.011 g/cm³
Solubility
Melting Point 47-48℃
Formula C₁₁H₁₇NO
Boiling Point 284.4 °C at 760 mmHg
Molecular Weight 179.262
Flash Point 99.8 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Benzylalcohol,α-[2-(dimethylamino)ethyl]-(6CI,7CI,8CI);3-Dimethylamino-1-phenyl-1-propanol;N,N-Dimethyl-3-hydroxy-3-phenylpropylamine;N,N-Dimethyl-3-phenyl-3-hydroxypropylamine;
PSA 23.47000
LogP 1.67170

Synthetic route

: 879-72-1
3-(dimethylamino)propiophenone hydrochloride

: 5554-64-3
N,N-dimethyl-3-hydroxy-3-phenylpropylamine

Conditions

Conditions	Yield
With methanol; sodium tetrahydroborate; sodium hydroxide at 20℃; for 1h; pH=12 - 13; Cooling with ice;	96%
Stage #1: 3-(dimethylamino)propiophenone hydrochloride With potassium hydroxide In water Stage #2: With methanol; sodium tetrahydroborate; potassium hydroxide at 0 - 22℃; for 1.5h;	95%
With diisobutylaluminium hydride In tetrahydrofuran; dichloromethane for 2h; Ambient temperature;	92%

: 3506-36-3
3-dimethylaminopropiophenone

: 5554-64-3
N,N-dimethyl-3-hydroxy-3-phenylpropylamine

Conditions

Conditions	Yield
With sodium tetrahydroborate In water at 0 - 20℃;	91%
With lithium aluminium tetrahydride
With aluminium trichloride; aluminum isopropoxide; isopropyl alcohol

: 87968-05-6
N,N-Dimethyl-α-chlorobenzoylacetamide

A: 5554-64-3
N,N-dimethyl-3-hydroxy-3-phenylpropylamine

: 1201-56-5
(+/-)-N-methylephedrine

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether for 20h; Heating;	A n/a B 24%

: 18776-12-0
3-chloro-1-phenyl-propan-1-ol

: 124-40-3
dimethyl amine

: 5554-64-3
N,N-dimethyl-3-hydroxy-3-phenylpropylamine

: 292638-84-7
styrene

: 30438-74-5
N-(chloromethyl)dimethylamine

A: 30457-88-6
2-benzyl-2-propenal

B: 5554-64-3
N,N-dimethyl-3-hydroxy-3-phenylpropylamine

C: 23580-89-4
methyl-(3-phenyl-propyl)-amine

D: 93948-20-0
bis-(3-phenyl-propyl)-amine

Conditions

Conditions	Yield
In acetonitrile for 12h; Heating; Yield given. Further byproducts given. Yields of byproduct given;

...Expand

: 60-29-7
diethyl ether

: 7732-18-5
water

: 3506-36-3
3-dimethylaminopropiophenone

activated aluminium: activated aluminium

A: 5554-64-3
N,N-dimethyl-3-hydroxy-3-phenylpropylamine

B 1.6-bis-dimethylamino-3.4-diphenyl-hexanediol-(3.4): 1.6-bis-dimethylamino-3.4-diphenyl-hexanediol-(3.4)

...Expand

β-dimethylamino-propiophenone hydrochloride: β-dimethylamino-propiophenone hydrochloride

: 5554-64-3
N,N-dimethyl-3-hydroxy-3-phenylpropylamine

Conditions

Conditions	Yield
With water; palladium Hydrogenation;

3-dimethylamino-1-phenyl-propanone-(1)-hydrochloride: 3-dimethylamino-1-phenyl-propanone-(1)-hydrochloride

: 5554-64-3
N,N-dimethyl-3-hydroxy-3-phenylpropylamine

Conditions

Conditions	Yield
With water; nickel Hydrogenation;

: 879-72-1
3-(dimethylamino)propiophenone hydrochloride

: 7732-18-5
water

palladium/charcoal: palladium/charcoal

: 5554-64-3
N,N-dimethyl-3-hydroxy-3-phenylpropylamine

Conditions

Conditions	Yield
Hydrogenation;

...Expand

: 98-86-2
acetophenone

: 5554-64-3
N,N-dimethyl-3-hydroxy-3-phenylpropylamine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 83 percent / aq. HCl / ethanol / 2 h / Heating 2: 91 percent / NaBH4 / H2O / 0 - 20 °C View Scheme
Multi-step reaction with 2 steps 1: hydrogenchloride / ethanol; water / 3 h / Heating / reflux 2: sodium tetrahydroborate / ethanol / 0 - 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: hydrogenchloride / ethanol / 2 h / Reflux 2.1: potassium hydroxide / water 2.2: 1.5 h / 0 - 22 °C View Scheme

: 98-86-2
acetophenone

butadiynediyl-bis magnesium bromide: butadiynediyl-bis magnesium bromide

: 5554-64-3
N,N-dimethyl-3-hydroxy-3-phenylpropylamine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 84 percent / conc. aq. HCl / ethanol / 2 h / Heating 2: 92 percent / DIBAL-H / tetrahydrofuran; CH2Cl2 / 2 h / Ambient temperature View Scheme

: 18871-71-1
N,N-dimethyl 3-oxo-3-phenyl-propanamide

: 5554-64-3
N,N-dimethyl-3-hydroxy-3-phenylpropylamine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 81 percent / N-chlorosuccinimide / CCl4 / 4 h / Heating 2: LiAlH4 / diethyl ether / 20 h / Heating View Scheme

: 3-(N,N-dimethylamino)propiophenone

: 5554-64-3
N,N-dimethyl-3-hydroxy-3-phenylpropylamine

Conditions

Conditions	Yield
With sodium borohydrid In methanol; water; isopropyl alcohol	15.2 g (97%)

: 5554-64-3
N,N-dimethyl-3-hydroxy-3-phenylpropylamine

: 1011-59-2
3-(dimethylamino)-1-phenylpropyl chloride hydrochloride

Conditions

Conditions	Yield
Stage #1: N,N-dimethyl-3-hydroxy-3-phenylpropylamine With hydrogenchloride In diethyl ether Stage #2: With thionyl chloride Reflux;	96%
With hydrogenchloride; thionyl chloride In dichloromethane
With thionyl chloride In dichloromethane

: 53939-30-3
5-bromo-2-chloropyridine

: 5554-64-3
N,N-dimethyl-3-hydroxy-3-phenylpropylamine

: 1584114-08-8
3-((5-bromopyridin-2-yl)oxy)-N,N-dimethyl-3-phenylpropan-1-amine

Conditions

Conditions	Yield
Stage #1: N,N-dimethyl-3-hydroxy-3-phenylpropylamine With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 1h; Stage #2: 5-bromo-2-chloropyridine In N,N-dimethyl-formamide; mineral oil at 75℃; for 12h;	91%

: 2075-46-9
4-nitro-1H-pyrazole

: 5554-64-3
N,N-dimethyl-3-hydroxy-3-phenylpropylamine

: 1557241-82-3
N,N-dimethyl-3-(4-nitro-1H-pyrazol-1-yl)-3-phenylpropan-1-amine

Conditions

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃;	80%
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃; Mitsunobu Displacement;

: 100-02-7
4-nitro-phenol

: 5554-64-3
N,N-dimethyl-3-hydroxy-3-phenylpropylamine

: 72084-00-5
N,N-dimethyl-3-(4-nitrophenoxy)-3-phenylpropan-1-amine

Conditions

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 16h; Mitsunobu Displacement;	80%
With di-isopropyl azodicarboxylate; triphenylphosphine In dichloromethane at 20℃; for 48h; Mitsunobu Displacement;

: 5554-64-3
N,N-dimethyl-3-hydroxy-3-phenylpropylamine

: 1422982-35-1
6-[1-(tetrahydropyran-2-yl)-1H-pyrazol-4-yl]-1-(2-trimethylsilanylethoxymethyl)-1H-indazole-3-carboxylic acid (1H-pyrazol-4-yl)amide

: C36H48N8O3Si

Conditions

Conditions	Yield
With tributylphosphine; diethylazodicarboxylate In tetrahydrofuran at 70℃; for 1h;	75%

: 496-15-1
1-indoline

: 5554-64-3
N,N-dimethyl-3-hydroxy-3-phenylpropylamine

: 915953-59-2
N-[3-(2,3-dihydro-1H-indol-1-yl)-3-phenylpropyl]-N,N-dimethylamine

Conditions

Conditions	Yield
Stage #1: N,N-dimethyl-3-hydroxy-3-phenylpropylamine With methanesulfonyl chloride; triethylamine In acetonitrile at 20℃; for 3h; Stage #2: 1-indoline With potassium carbonate at 20℃; for 14h; Further stages.;	72%

: 5554-64-3
N,N-dimethyl-3-hydroxy-3-phenylpropylamine

: 108-95-2
phenol

: N,N-dimethyl-3-phenoxy-3-phenyl-1-propanamine

Conditions

Conditions	Yield
Stage #1: N,N-dimethyl-3-hydroxy-3-phenylpropylamine With methanesulfonyl chloride; triethylamine In acetonitrile Stage #2: phenol With potassium carbonate In acetonitrile for 65h; Heating;	69%

: 2033-89-8
3,4-dimethoxyphenol

: 5554-64-3
N,N-dimethyl-3-hydroxy-3-phenylpropylamine

: [3-(3,4-dimethoxy-phenoxy)-3-phenyl-propyl]-dimethyl-amine

Conditions

Conditions	Yield
Stage #1: N,N-dimethyl-3-hydroxy-3-phenylpropylamine With methanesulfonyl chloride; triethylamine In acetonitrile at 20℃; for 3h; Stage #2: 3,4-dimethoxyphenol With potassium carbonate In acetonitrile for 16h; Heating;	67%

: 2343-23-9
6-fluoroindoline

: 5554-64-3
N,N-dimethyl-3-hydroxy-3-phenylpropylamine

: 915953-62-7
C19H23N2F

Conditions

Conditions	Yield
Stage #1: N,N-dimethyl-3-hydroxy-3-phenylpropylamine With methanesulfonyl chloride; triethylamine In acetonitrile at 20℃; for 3h; Stage #2: 6-fluoroindoline With potassium carbonate at 20℃; for 14h; Further stages.;	64%

: 5554-64-3
N,N-dimethyl-3-hydroxy-3-phenylpropylamine

: 79130-51-1
3-chloro-N,N-dimethyl-3-phenylpropan-1-amine

Conditions

Conditions	Yield
With methanesulfonyl chloride; triethylamine In dichloromethane at 20℃;	64%

: 5554-64-3
N,N-dimethyl-3-hydroxy-3-phenylpropylamine

: 82830-49-7
2-fluoro-1,4-dimethoxybenzene

: 1342798-05-3
[3-(2,5-dimethoxy-phenoxy)-3-phenylpropyl]dimethylamine

Conditions

Conditions	Yield
Stage #1: N,N-dimethyl-3-hydroxy-3-phenylpropylamine With sodium hydride In dimethyl sulfoxide at 20℃; for 0.5h; Stage #2: 2-fluoro-1,4-dimethoxybenzene In dimethyl sulfoxide at 135 - 140℃; for 4h;	63%

: 41288-96-4
6-chloropyridine-3-ol

: 5554-64-3
N,N-dimethyl-3-hydroxy-3-phenylpropylamine

: 1584114-00-0
3-((6-chloropyridin-3-yl)oxy)-N,N-dimethyl-3-phenylpropan-1-amine

Conditions

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; Mitsunobu Displacement; Inert atmosphere;	60%

: 5554-64-3
N,N-dimethyl-3-hydroxy-3-phenylpropylamine

: 552866-98-5
2,3-dihydro-4-fluoro-1H-indole

: 915953-60-5
C19H23N2F

Conditions

Conditions	Yield
Stage #1: N,N-dimethyl-3-hydroxy-3-phenylpropylamine With methanesulfonyl chloride; triethylamine In acetonitrile at 20℃; for 3h; Stage #2: 2,3-dihydro-4-fluoro-1H-indole With potassium carbonate at 20℃; for 14h; Further stages.;	51%

: 2343-22-8
5-fluoroindoline

: 5554-64-3
N,N-dimethyl-3-hydroxy-3-phenylpropylamine

: 915953-61-6
C19H23N2F

Conditions

Conditions	Yield
Stage #1: N,N-dimethyl-3-hydroxy-3-phenylpropylamine With methanesulfonyl chloride; triethylamine In acetonitrile at 20℃; for 3h; Stage #2: 5-fluoroindoline With potassium carbonate at 20℃; for 14h; Further stages.;	49%

: 769966-04-3
2,3-dihydro-7-fluoro-1H-indole

: 5554-64-3
N,N-dimethyl-3-hydroxy-3-phenylpropylamine

: 915953-63-8
C19H23N2F

Conditions

Conditions	Yield
Stage #1: N,N-dimethyl-3-hydroxy-3-phenylpropylamine With methanesulfonyl chloride; triethylamine In acetonitrile at 20℃; for 3h; Stage #2: 2,3-dihydro-7-fluoro-1H-indole With potassium carbonate at 20℃; for 14h; Further stages.;	47%

: 150-19-6
O-methylresorcine

: 5554-64-3
N,N-dimethyl-3-hydroxy-3-phenylpropylamine

: 57226-14-9
[3-(3-methoxy-phenoxy)-3-phenyl-propyl]-dimethyl-amine

Conditions

Conditions	Yield
With PS-PPh3; dibenzyl azodicarboxylate In dichloromethane at 20℃; for 20h; Mitsunobu reaction;	47%

: 943830-74-8
4-fluorobenzo[1,3]dioxolane

: 5554-64-3
N,N-dimethyl-3-hydroxy-3-phenylpropylamine

: 144-62-7
oxalic acid

: 3-[(benzo[d][1,3]dioxolan-4-yl)oxy]-N,N-dimethyl-3-phenylpropylamine oxalate

Conditions

Conditions	Yield
Stage #1: 4-fluorobenzo[1,3]dioxolane; N,N-dimethyl-3-hydroxy-3-phenylpropylamine With potassium hydroxide In dimethyl sulfoxide at 85℃; for 4h; Stage #2: oxalic acid	47%

...Expand

: 5554-64-3
N,N-dimethyl-3-hydroxy-3-phenylpropylamine

: 150-76-5
4-methoxy-phenol

: N,N-dimethyl-3-(4-methoxy-phenyloxy)-3-phenyl-propanamine

Conditions

Conditions	Yield
Stage #1: N,N-dimethyl-3-hydroxy-3-phenylpropylamine With methanesulfonyl chloride; triethylamine In acetonitrile at 20℃; for 3h; Stage #2: 4-methoxy-phenol With potassium carbonate In acetonitrile for 16h; Heating;	46%

: 402-45-9
4-hydroxybenzotrifluoride

: 5554-64-3
N,N-dimethyl-3-hydroxy-3-phenylpropylamine

: 56225-81-1
N,N-dimethyl-3-phenyl-3-(4-(trifluoromethyl)phenoxy)-1-propylamine

Conditions

Conditions	Yield
Stage #1: N,N-dimethyl-3-hydroxy-3-phenylpropylamine With methanesulfonyl chloride; triethylamine In acetonitrile at 20℃; for 3h; Stage #2: 4-hydroxybenzotrifluoride With potassium carbonate In acetonitrile for 16h; Heating;	35%

: 81878-15-1
4-(3-piperidin-1-yl-propoxy)-phenol

: 5554-64-3
N,N-dimethyl-3-hydroxy-3-phenylpropylamine

: dimethyl-{3-phenyl-3-[4-(3-piperidin-1-yl-propoxy)-phenoxy]-propyl}-amine

Conditions

Conditions	Yield
With PS-PPh3; dibenzyl azodicarboxylate In dichloromethane at 20℃; for 20h; Mitsunobu reaction;	10%

: 5554-64-3
N,N-dimethyl-3-hydroxy-3-phenylpropylamine

: 2902-98-9
2-chloro-2,2-diphenylacetyl chloride

: 801171-59-5
benzilic acid-(3-dimethylamino-1-phenyl-propyl ester)

Conditions

Conditions	Yield
With diethyl ether Erhitzen des Reaktionsprodukts mit Wasser;

: 5554-64-3
N,N-dimethyl-3-hydroxy-3-phenylpropylamine

: 25314-81-2
benzoic acid-(3-dimethylamino-1-phenyl-propyl ester)

Conditions

Conditions	Yield
With benzoyl chloride In 1,4-dioxane at 25 - 50℃; Kinetics;

: 5554-64-3
N,N-dimethyl-3-hydroxy-3-phenylpropylamine

: 98-88-4
benzoyl chloride

: 25314-81-2
benzoic acid-(3-dimethylamino-1-phenyl-propyl ester)

Conditions

Conditions	Yield
In benzene

: 5554-64-3
N,N-dimethyl-3-hydroxy-3-phenylpropylamine

: 74-88-4
methyl iodide

: 24221-52-1
3-Hydroxy-3-phenylpropyltrimethylammoniumiodid

Conditions

Conditions	Yield
In ethanol for 0.666667h; Heating; Yield given;

: 5554-64-3
N,N-dimethyl-3-hydroxy-3-phenylpropylamine

: 611-71-2
(R)-Mandelic Acid

: (R)-3-Dimethylamino-1-phenyl-propan-1-ol; compound with (R)-hydroxy-phenyl-acetic acid

Conditions

Conditions	Yield
In ethyl acetate 77 deg C, 1 h and -15 deg C, 1 h; Yield given;

Benzenemethanol,α-[2-(dimethylamino)ethyl]- Specification

The Benzenemethanol, α-[2-(dimethylamino)ethyl]-, with the CAS registry number 5554-64-3, is also known as 1-Phenyl-3-(dimethylamino)-1-propanol. This chemical's molecular formula is C₁₁H₁₇NO and molecular weight is 179.258780. What's more, its IUPAC name is 3-(Dimethylamino)-1-phenylpropan-1-ol.

Physical properties about Benzenemethanol, α-[2-(dimethylamino)ethyl]- are: (1)ACD/LogP: 1.29; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1.67; (4)ACD/LogD (pH 7.4): -0.35; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 2.75; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 12.47 Å²; (13)Index of Refraction: 1.532; (14)Molar Refractivity: 54.95 cm³; (15)Molar Volume: 177.2 cm³; (16)Polarizability: 21.78×10^-24 cm³; (17)Surface Tension: 39.4 dyne/cm; (18)Density: 1.011 g/cm³; (19)Flash Point: 99.8 °C; (20)Enthalpy of Vaporization: 55.28 kJ/mol; (21)Boiling Point: 284.4 °C at 760 mmHg; (22)Vapour Pressure: 0.0014 mmHg at 25 °C.

You can still convert the following datas into molecular structure:
(1) SMILES: OC(c1ccccc1)CCN(C)C
(2) InChI: InChI=1/C11H17NO/c1-12(2)9-8-11(13)10-6-4-3-5-7-10/h3-7,11,13H,8-9H2,1-2H3
(3) InChIKey: VELGOYBSKBKQFF-UHFFFAOYAB

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intraperitoneal	200mg/kg (200mg/kg)		National Technical Information Service. Vol. AD277-689,

Product Name

3-dimethylamino-1-phenyl-propan-1-ol

Synthetic route

Benzenemethanol,α-[2-(dimethylamino)ethyl]- Specification

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