3-Methylamino-1-(2-thienyl)-1-propanol supplier

Name
3-Methylamino-1-(2-thienyl)-1-propanol
EINECS 601-437-5
CAS No. 116539-55-0
Article Data48
CAS DataBase
Density 1.128 g/cm³
Solubility
Melting Point 72.0 to 76.0 °C
Formula C₈H₁₃NOS
Boiling Point 294.288 °C at 760 mmHg
Molecular Weight 171.263
Flash Point 131.781 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 2-Thiophenemethanol,a-[2-(methylamino)ethyl]-, (S)-;(1S)-(-)-3-(Methylamino)-1-(thien-2-yl)propan-1-ol;(S)-(-)-3-(N-Methylamino)-1-(2-thienyl)-1-propanol;(S)-3-Methylamino-1-(2-thienyl)-1-propanol;N-Methyl-(S)-(-)-3-Hydroxy-3-(2-thiophen)propylamine;3-Methylamino-1-(2-thienyl)-1-propanol;N-methyl-3-hydroxy-3-(2-thienyl)-3-aminopropane;(S)-3-MethylaMino-1-(thiophene-2-yl)propan-1-ol;
PSA 60.50000
LogP 1.78190

Synthetic route

: 1035456-55-3
C8H13NO2S

: 116539-55-0
(S)-3-methylamino-1-(2-thienyl)-1-propanol

Conditions

Conditions	Yield
Stage #1: C8H13NO2S With acetic acid; zinc In water at 50℃; for 1.5h; Stage #2: With sodium hydroxide In water	100%

: 603959-56-4
(S)-3-hydroxy-N-methyl-3-(thiophen-2-yl)propanamide

: 116539-55-0
(S)-3-methylamino-1-(2-thienyl)-1-propanol

Conditions

Conditions	Yield
With borane-THF In tetrahydrofuran at 20℃; for 4h; Reagent/catalyst;	98%
Stage #1: (S)-3-hydroxy-N-methyl-3-(thiophen-2-yl)propanamide With sodium tetrahydroborate; iodine In tetrahydrofuran at 20℃; for 4.33333h; Heating / reflux; Stage #2: With sodium hydroxide; water In tetrahydrofuran; water; butanone at 64℃; for 0.333333h;	91%
With lithium aluminium tetrahydride In tetrahydrofuran Heating / reflux;	80%

: 74-89-5
methylamine

: 556801-68-4
(S)-3-hydroxy-3-(2-thienyl)propyl methanesulfonate

: 116539-55-0
(S)-3-methylamino-1-(2-thienyl)-1-propanol

Conditions

Conditions	Yield
In tetrahydrofuran; water at 65℃; for 3h;	94%

: N-methyl-3-(thien-2-yl)-3-morpholino-propylamine hydrochloride

: 116539-55-0
(S)-3-methylamino-1-(2-thienyl)-1-propanol

Conditions

Conditions	Yield
With Rh[((S,S)-BenzP*)(cod)]SbF6; hydrogen; caesium carbonate; zinc(II) chloride In methanol at 20℃; under 19001.3 Torr; for 20h; Reagent/catalyst; Solvent; Autoclave; enantioselective reaction;	94%
With hydrogen; potassium carbonate; [Rh{(SC,RP)-duanphos}(norbornadiene)]SbF6 In methanol at 20℃; under 7500.6 Torr; for 12h;	93%
With [Rh((S,S)-QuinoxP*)(cod)]SbF6; potassium tert-butylate; hydrogen; zinc(II) iodide In tetrahydrofuran at 25℃; under 15001.5 Torr; for 12h; Reagent/catalyst; enantioselective reaction;	83%

: 1204210-39-8
(S)-3-(N-trifluoroacetyl-N-methyl)amino-1-(2-thienyl)propan-1-ol

: 116539-55-0
(S)-3-methylamino-1-(2-thienyl)-1-propanol

Conditions

Conditions	Yield
With water; sodium carbonate In methanol at 20℃; for 4h;	94%

: 1146978-94-0
(S)-[3-methoxy(methyl)amino]-1-(2-thienyl)propan-1-ol

: 116539-55-0
(S)-3-methylamino-1-(2-thienyl)-1-propanol

Conditions

Conditions	Yield
With hydrogen; Raney-nickel In methanol at 50℃; for 12h; Autoclave;	90.8%
Raney-nickel In methanol at 50℃; for 12h; Autoclave;

: 597581-29-8
((S)-3-Hydroxy-3-thiophen-2-yl-propyl)-carbamic acid ethyl ester

: 116539-55-0
(S)-3-methylamino-1-(2-thienyl)-1-propanol

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran for 1.5h; Heating;	88%

: salt of (S)-(-)-3-N-methylamino-1-(2-thienyl)-1-propanol and (-)-2,3:4,6-di-O-isopropylidene-2-keto-L-gulonic acid

: 116539-55-0
(S)-3-methylamino-1-(2-thienyl)-1-propanol

Conditions

Conditions	Yield
With sodium hydroxide In dichloromethane; water for 0.25h; Product distribution / selectivity;	87%

: 164071-56-1
(S)-3-chloro-1-(thiophen-2-yl)propan-1-ol

: 74-89-5
methylamine

: 116539-55-0
(S)-3-methylamino-1-(2-thienyl)-1-propanol

Conditions

Conditions	Yield
With chloro-trimethyl-silane In methanol; water at 80℃; for 8h; Reagent/catalyst;	85%

: 654062-24-5
(S)-3-methyl-6-(2-thienyl)-1,3-oxazinan-2-one

: 116539-55-0
(S)-3-methylamino-1-(2-thienyl)-1-propanol

Conditions

Conditions	Yield
With water; lithium hydroxide In methanol for 8h; Reflux;	84%

: C12H17NO5S

: 116539-55-0
(S)-3-methylamino-1-(2-thienyl)-1-propanol

Conditions

Conditions	Yield
With methanol; potassium hydroxide at 75℃; for 4h;	83%

: 625853-22-7
phenyl (S)-N-[3-acetoxy-3-(thien-2-yl)propyl]-N-methylcarbamate

: 116539-55-0
(S)-3-methylamino-1-(2-thienyl)-1-propanol

Conditions

Conditions	Yield
With methanol; potassium hydroxide at 75℃; for 4h;	83%

: 164071-58-3
S-(-)-3-iodo-1-(2-thienyl)-1-propanol

: 74-89-5
methylamine

: 116539-55-0
(S)-3-methylamino-1-(2-thienyl)-1-propanol

Conditions

Conditions	Yield
In tetrahydrofuran; water at 25℃; for 12h; Inert atmosphere;	80%
In tetrahydrofuran; water for 6h; Ambient temperature;	71.5%
In tetrahydrofuran; water at 20℃; for 18h;	71%
In tetrahydrofuran
In tetrahydrofuran; water at 20℃; for 18h;

: 1337865-86-7
3-(N-methyl-N-benzylamino)-1-(2-thienyl)-2-propen-1-one

: 116539-55-0
(S)-3-methylamino-1-(2-thienyl)-1-propanol

Conditions

Conditions	Yield
With potassium tert-butylate; hydrogen; [(R)-Binap RuCl2 (R)-DAIPEN] In isopropyl alcohol at 80℃; under 7500.75 Torr; for 16h; Inert atmosphere;	80%

: 132335-44-5
(S)-3-dimethylamino-1-(2-thienyl)propan-1-ol

: 543-27-1
isobutyl chloroformate

: 116539-55-0
(S)-3-methylamino-1-(2-thienyl)-1-propanol

Conditions

Conditions	Yield
Stage #1: (S)-3-dimethylamino-1-(2-thienyl)propan-1-ol; isobutyl chloroformate With triethylamine In toluene at 20 - 30℃; for 6h; Stage #2: With potassium hydroxide In methanol at 75℃; for 3.5h; Heating / reflux;	79.6%

: 39145-15-8
3-methylamino-1-thiophen-2-yl-propenone

: 116539-55-0
(S)-3-methylamino-1-(2-thienyl)-1-propanol

Conditions

Conditions	Yield
With hydrogen; potassium carbonate; ruthenium(II) chloride In isopropyl alcohol at 30℃; under 18751.9 Torr; for 18h;	79.2%

: 74-89-5
methylamine

: 591727-36-5
(S)-1-hydroxy-3-(thiophen-2-yl)propanenitrile

: 116539-55-0
(S)-3-methylamino-1-(2-thienyl)-1-propanol

Conditions

Conditions	Yield
With hydrogen; nickel In methanol; water at 65℃; under 37503.8 Torr; for 24h; Product distribution / selectivity;	79%
With hydrogen; 5%-palladium/activated carbon In methanol; water at 60℃; under 75007.5 Torr; for 24h; Product distribution / selectivity;	74%

: (S)-3-(N-ethoxycarbonyl-N-methyl)amino-1-ethoxycarbonyloxy-(2-thienyl)propane

: 116539-55-0
(S)-3-methylamino-1-(2-thienyl)-1-propanol

Conditions

Conditions	Yield
With sodium hydroxide In ethanol; water at 82℃; for 3h;	74.6%

: N-methyl-3-(thien-2-yl)-3-morpholino-propylamine hydrochloride

A: 116539-55-0
(S)-3-methylamino-1-(2-thienyl)-1-propanol

B: 116539-57-2
(R)-3-(methylamino)-1-(thiophen-2-yl)propan-1-ol

Conditions

Conditions	Yield
With lithium aluminium tetrahydride Product distribution / selectivity;	A 74% B n/a
With hydrogen; sodium methylate; bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; (S)-(-)-(6,6’-dimethoxybiphenyl-2,2’-diyl)bis(diphenylphosphine) In methanol at 30 - 50℃; under 22502.3 Torr; for 24h; Product distribution / selectivity;	A 12.7 - 20.4 %Chromat. B n/a
With hydrogen; sodium methylate; ethyl acetoacetate; [(12aS)-6,7-dihudrodibenzo[e,g][1,4]dioxocin-1,12-diyl]bis[diphenylphosphine]; bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate In methanol at 50℃; under 22502.3 Torr; for 24h; Product distribution / selectivity;	A 6.2 %Chromat. B n/a
With hydrogen; [(12aS)-6,7-dihudrodibenzo[e,g][1,4]dioxocin-1,12-diyl]bis[diphenylphosphine]; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 In methanol at 50℃; under 22502.3 Torr; for 24h; Product distribution / selectivity;	A 11.6 %Chromat. B n/a
With hydrogen; [(12aS)-6,7-dihudrodibenzo[e,g][1,4]dioxocin-1,12-diyl]bis[diphenylphosphine]; bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate In methanol at 50℃; under 22502.3 Torr; for 24h; Product distribution / selectivity;	A 4 %Chromat. B n/a

: (S)-3-N-methylammonio-1-(2-thienyl)-1-propanol 2,3:4,6-di-O-isopropylidene-2-keto-L-gulonate

: 116539-55-0
(S)-3-methylamino-1-(2-thienyl)-1-propanol

Conditions

Conditions	Yield
With potassium hydroxide In water	70%
With sodium carbonate In water for 0.25h;	61%
With sodium hydroxide In water

: 625853-14-7
(S)-N-(3-hydroxy-3-(thiophen-2-yl)propyl)-N-methylacetamide

: 116539-55-0
(S)-3-methylamino-1-(2-thienyl)-1-propanol

Conditions

Conditions	Yield
With potassium hydroxide In methanol at 70℃; for 2h;	68%

: (S)-MMAA (S)-mandelic acid monohydrate

: 116539-55-0
(S)-3-methylamino-1-(2-thienyl)-1-propanol

Conditions

Conditions	Yield
With sodium hydroxide In water; iso-butanol	66%

: C9H13NO2S

: 116539-55-0
(S)-3-methylamino-1-(2-thienyl)-1-propanol

Conditions

Conditions	Yield
With bis-[(trifluoroacetoxy)iodo]benzene In water; acetonitrile for 4h; Reflux;	54%

: 3-N-methylamino-1-(2-thienyl)-1-propanone methanesulphonate

: 116539-55-0
(S)-3-methylamino-1-(2-thienyl)-1-propanol

Conditions

Conditions	Yield
With formic acid; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; triethylamine; N-[(1S,2S)-2-amino-1,2-diphenylethyl]-4-methylbenzenesulfonamide In methanol at 40 - 45℃; for 2h; Time; Reagent/catalyst;	48%

: N-methyl-3-(thien-2-yl)-3-morpholino-propylamine hydrochloride

: 7480-35-5, 13286-59-4, 74165-73-4, 126456-43-7, 136030-00-7, 140632-19-5, 140632-20-8
(1S,2R)-1-amino-2-indanol

A: 116539-55-0
(S)-3-methylamino-1-(2-thienyl)-1-propanol

B: 116539-57-2
(R)-3-(methylamino)-1-(thiophen-2-yl)propan-1-ol

Conditions

Conditions	Yield
With sodium hydroxide; (p-cymene)-ruthenium(II) chloride dimer In isopropyl alcohol at 20 - 85℃; for 5h;	A 39% B n/a

...Expand

: 116539-56-1
3-(methylamino)-1-(thiophen-2-yl)propan-1-ol

A: 116539-55-0
(S)-3-methylamino-1-(2-thienyl)-1-propanol

B: 116539-57-2
(R)-3-(methylamino)-1-(thiophen-2-yl)propan-1-ol

Conditions

Conditions	Yield
With (S)-Mandelic acid In water at 29 - 50℃;	A 27% B n/a
With diethylamine In ethanol; n-heptane Resolution of racemate;

: 919530-17-9
(2S,6S)-2-[(S)-1-triisopropylsilyloxyethyl]-3-methyl-6-(thiophen-2-yl)-1,3-oxazinane

: 116539-55-0
(S)-3-methylamino-1-(2-thienyl)-1-propanol

Conditions

Conditions	Yield
With hydrogenchloride In tetrahydrofuran; water at 20℃; for 4h;

: 919530-12-4
(2S,6S)-2-[(S)-1-triisopropylsilyloxyethyl]-6-(thiophen-2-yl)-[1,3]oxazinan-4-one

: 116539-55-0
(S)-3-methylamino-1-(2-thienyl)-1-propanol

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: LiHMDS / tetrahydrofuran / 0 - 20 °C 2: Ph2SiH2 / RhH(CO)(PPh3)3 / tetrahydrofuran / 15 h / 20 °C 3: HCl / H2O; tetrahydrofuran / 4 h / 20 °C View Scheme

: 919530-14-6
(2S,6S)-N-methyl-2-[(S)-1-triisopropylsilyloxyethyl]-6-(thiophen-2-yl)-[1,3]oxazinan-4-one

: 116539-55-0
(S)-3-methylamino-1-(2-thienyl)-1-propanol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: Ph2SiH2 / RhH(CO)(PPh3)3 / tetrahydrofuran / 15 h / 20 °C 2: HCl / H2O; tetrahydrofuran / 4 h / 20 °C View Scheme

: 98-03-3
thiophene-2-carbaldehyde

polymer-bound-N-(3-(4-bromophenyl)-3-oxopropanamide): polymer-bound-N-(3-(4-bromophenyl)-3-oxopropanamide)

: 116539-55-0
(S)-3-methylamino-1-(2-thienyl)-1-propanol

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 36 percent / BF3*Et2O / CH2Cl2 / -78 - 20 °C 2: aluminum amalgam / propan-2-ol 3: LiHMDS / tetrahydrofuran / 0 - 20 °C 4: Ph2SiH2 / RhH(CO)(PPh3)3 / tetrahydrofuran / 15 h / 20 °C 5: HCl / H2O; tetrahydrofuran / 4 h / 20 °C View Scheme

: 321-38-0
1-Fluoronaphthalene

: 116539-55-0
(S)-3-methylamino-1-(2-thienyl)-1-propanol

: 136434-34-9
duloxetine hydrochloride

Conditions

Conditions	Yield
Stage #1: 1-Fluoronaphthalene; (S)-3-methylamino-1-(2-thienyl)-1-propanol With sodium hydride In paraffin oil (nujol); dimethyl sulfoxide at 20 - 50℃; Stage #2: With hydrogenchloride; acetic acid In Isopropyl acetate at 0 - 15℃; for 5h;	93%
Stage #1: (S)-3-methylamino-1-(2-thienyl)-1-propanol With sodium hydride In dimethyl sulfoxide at 20 - 35℃; Stage #2: 1-Fluoronaphthalene In dimethyl sulfoxide at 45 - 50℃; for 30h; Stage #3: With hydrogenchloride In water; dimethyl sulfoxide; toluene pH=4 - 5; Solvent;

: 321-38-0
1-Fluoronaphthalene

: 116539-55-0
(S)-3-methylamino-1-(2-thienyl)-1-propanol

: 116539-58-3, 116539-59-4, 116539-60-7, 116817-13-1
Duloxetine

Conditions

Conditions	Yield
With potassium tert-butylate In dimethyl sulfoxide at 60℃; for 8h;	90%
With potassium tert-butylate In dimethyl sulfoxide at 60℃; for 8h;	90%
With sodium hydride In dimethyl sulfoxide for 8h;	81%

: 98-09-9
benzenesulfonyl chloride

: 116539-55-0
(S)-3-methylamino-1-(2-thienyl)-1-propanol

: N-[3S-hydroxy-3-(thiophen-2-yl)propyl]-N-methylbenzenesulfonamide

Conditions

Conditions	Yield
With pyridine In dichloromethane at 0 - 20℃; for 14h;	90%

: 1073-06-9
3-fluorobromobenzene

: 116539-55-0
(S)-3-methylamino-1-(2-thienyl)-1-propanol

: (S)-3-(3-bromophenoxy)-N-methyl-3-(thiophen-2-yl)propan-1-amine

Conditions

Conditions	Yield
Stage #1: (S)-3-methylamino-1-(2-thienyl)-1-propanol With sodium hydride In N,N-dimethyl acetamide; mineral oil at 20℃; for 0.5h; Stage #2: 3-fluorobromobenzene In N,N-dimethyl acetamide; mineral oil at 90℃; for 3h;	90%
Stage #1: (S)-3-methylamino-1-(2-thienyl)-1-propanol With sodium hydride In N,N-dimethyl acetamide; mineral oil at 20℃; for 0.5h; Stage #2: 3-fluorobromobenzene In N,N-dimethyl acetamide; mineral oil at 90℃; for 3h;

: 3144-16-9
(1S)-10-camphorsulfonic acid

: 116539-55-0
(S)-3-methylamino-1-(2-thienyl)-1-propanol

: (S)-3-methylamino-1-thiophen-2-yl-propan-1-ol 1-(S)-(7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl)-methanesulfonate

Conditions

Conditions	Yield
In ethanol; ethyl acetate at 30 - 50℃; for 0.916667h; Product distribution / selectivity;	89%

: 104-15-4
toluene-4-sulfonic acid

: 116539-55-0
(S)-3-methylamino-1-(2-thienyl)-1-propanol

: (S)-(-)-3-N-methylamino-1-(2-thienyl)-1-propanol p-toluenesulfonate

Conditions

Conditions	Yield
In methanol; dichloromethane at 25℃; for 1h; Product distribution / selectivity;	60%

: 96013-76-2
4-[2-(tert-butyldimethylsilyloxy)ethyl]phenol

: 116539-55-0
(S)-3-methylamino-1-(2-thienyl)-1-propanol

: 1615654-56-2
(R)-3-[4-[2-(tert-butyldimethylsilyloxy)ethyl]phenoxy]-N-methyl-3-(thiophen-2-yl)propan-1-amine

Conditions

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In ethyl acetate; toluene	52%
With triphenylphosphine; diethylazodicarboxylate In toluene at 20℃; for 18h;	52%

3-Methylamino-1-(2-thienyl)-1-propanol Specification

The 3-Methylamino-1-(2-thienyl)-1-propanol, with the CAS registry number 116539-55-0, has the systematic name of (1S)-3-(methylamino)-1-(thiophen-2-yl)propan-1-ol. And the molecular formula of the chemical is C₈H₁₃NOS.

The characteristics of this chemical are as followings: (1)ACD/LogP: 0.32; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -3; (4)ACD/LogD (pH 7.4): -3; (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): 1; (9)#H bond acceptors: 2; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 60.5 Å²; (13)Index of Refraction: 1.553; (14)Molar Refractivity: 48.585 cm³; (15)Molar Volume: 151.814 cm³; (16)Polarizability: 19.261×10^-24cm³; (17)Surface Tension: 43.53 dyne/cm; (18)Density: 1.128 g/cm³; (19)Flash Point: 131.781 °C; (20)Enthalpy of Vaporization: 56.385 kJ/mol; (21)Boiling Point: 294.288 °C at 760 mmHg; (22)Vapour Pressure: 0.001 mmHg at 25°C.

Addtionally, the following datas could be converted into the molecular structure:
(1)SMILES: O[C@H](c1sccc1)CCNC
(2)InChI: InChI=1/C8H13NOS/c1-9-5-4-7(10)8-3-2-6-11-8/h2-3,6-7,9-10H,4-5H2,1H3/t7-/m0/s1
(3)InChIKey: YEJVVFOJMOHFRL-ZETCQYMHBE

Product Name

3-Methylamino-1-(2-thienyl)-1-propanol

Synthetic route

3-Methylamino-1-(2-thienyl)-1-propanol Specification

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