Palmatine chloride supplier | CasNO.10605-02-4

Name
Palmatine chloride
EINECS
CAS No. 10605-02-4
Article Data7
CAS DataBase
Density 1.25g/cm³
Solubility
Melting Point 205℃
Formula C₂₁H₂₂ClNO₄
Boiling Point 611.8°C at 760 mmHg
Molecular Weight 387.863
Flash Point 184.1°C
Transport Information
Appearance
Safety 24/45
Risk Codes 20/22-36/38
Molecular Structure
Hazard Symbols
Synonyms Dibenzo(a,g)quinolizinium, 5,6-dihydro-2,3,9,10-tetramethoxy-, chloride;Palmatine chloride(6CI,7CI);Fibrauretin;
PSA 40.80000
LogP 0.38880

Synthetic route

: 2-[2-(6,7-dimethoxyisoquinolin-3-yl)-4,5-dimethoxyphenyl]ethanol

: 10605-02-4
palmatine chloride

Conditions

Conditions	Yield
With methanesulfonyl chloride; triethylamine In dichloromethane at 20℃; for 6h;	92%
With tetrachloromethane; triphenylphosphine In dichloromethane at 27 - 30℃; for 24h; Inert atmosphere;	70%

: 2-(2-(2-(1,3-dioxolan-2-yl)-3,4-dimethoxyphenyl)acetyl)-4,5-dimethoxyphenethyl pivalate

: 10605-02-4
palmatine chloride

Conditions

Conditions	Yield
Stage #1: 2-(2-(2-(1,3-dioxolan-2-yl)-3,4-dimethoxyphenyl)acetyl)-4,5-dimethoxyphenethyl pivalate With ammonium chloride In ethanol; water at 90 - 110℃; for 56h; Stage #2: With sodium hydroxide In water for 0.0833333h;	88%
With ammonium chloride In ethanol; water at 90 - 110℃; for 66h; Inert atmosphere;

: 80-48-8
methyl p-toluene sulfonate

: 2,3-dihydroxy-9,10-dimethoxy-5,6-dihydro-isoquino[3,2-a]isoquinolinylium chloride

: 10605-02-4
palmatine chloride

Conditions

Conditions	Yield
Stage #1: methyl p-toluene sulfonate; 2,3-dihydroxy-9,10-dimethoxy-5,6-dihydro-isoquino[3,2-a]isoquinolinylium chloride With potassium carbonate In acetonitrile at 80℃; for 12h; Green chemistry; Stage #2: Reagent/catalyst; Solvent; Temperature; Green chemistry;	80%

: 77-78-1
dimethyl sulfate

: 2,3-dihydroxy-9,10-dimethoxy-5,6-dihydro-isoquino[3,2-a]isoquinolinylium chloride

: 10605-02-4
palmatine chloride

Conditions

Conditions	Yield
With potassium carbonate In methanol at 60℃; for 6h;	75%

: 2,3-dihydroxyberberine methanesulfonate

: 616-38-6
carbonic acid dimethyl ester

: 10605-02-4
palmatine chloride

Conditions

Conditions	Yield
Stage #1: 2,3-dihydroxyberberine methanesulfonate; carbonic acid dimethyl ester With caesium carbonate In N,N-dimethyl-formamide at 140℃; for 8h; Stage #2: With hydrogenchloride In water for 0.5h; Solvent; Reagent/catalyst;	73.5%

: 2,3-dihydroxy-9,10-dimethoxy-5,6-dihydro-isoquino[3,2-a]isoquinolinylium chloride

: 74-88-4
methyl iodide

: 10605-02-4
palmatine chloride

Conditions

Conditions	Yield
With sodium hydroxide In methanol at 25℃; for 6h;	60%

: 2-{[2-(2-hydroxyethyl)-4,5-dimethoxyphenyl]ethynyl}-4,5-dimethoxybenzaldehyde

: 10605-02-4
palmatine chloride

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: silver nitrate; ammonium acetate / tert-butyl alcohol / 14 h / 27 - 30 °C / Inert atmosphere 2: triphenylphosphine; tetrachloromethane / dichloromethane / 24 h / 27 - 30 °C / Inert atmosphere View Scheme

: 2-acetyl-4,5-dimethoxyphenethyl pivalate

: 2-(6-bromo-2,3-dimethoxyphenyl)-1,3-dioxolane

: 10605-02-4
palmatine chloride

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: caesium carbonate; bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) / tetrahydrofuran / 18 h / 90 °C / Inert atmosphere 2: ammonium chloride / water; ethanol / 66 h / 90 - 110 °C / Inert atmosphere View Scheme

: 633-65-8
berberine chloride

: 10605-02-4
palmatine chloride

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: trifluorormethanesulfonic acid / 5,5-dimethyl-1,3-cyclohexadiene / 0.5 h / 25 °C 1.2: 0 °C 1.3: anion-exchange resin (Cl-) 2.1: potassium carbonate / acetonitrile / 12 h / 80 °C / Green chemistry 2.2: anion-exchange resin (Cl-) / Green chemistry View Scheme
Multi-step reaction with 2 steps 1.1: trifluorormethanesulfonic acid / 5,5-dimethyl-1,3-cyclohexadiene / 0.5 h / 25 °C 1.2: 0 °C 1.3: anion-exchange resin (Cl-) 2.1: potassium carbonate / methanol / 6 h / 60 °C View Scheme

: 4393-09-3
2,3-dimethoxybenzyl amine

: 10605-02-4
palmatine chloride

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: C14H22O4Rh / water / 24 h / 100 °C / Sealed tube; Green chemistry 2.1: bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] / 2 h / 100 °C 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 3.2: 1 h / 20 °C View Scheme

: 1-(3,4-dimethoxyphenyl)-2-(dimethyl(oxo)-λ6-sulfanylidene)ethan-1-one

: 10605-02-4
palmatine chloride

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: C14H22O4Rh / water / 24 h / 100 °C / Sealed tube; Green chemistry 2.1: bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] / 2 h / 100 °C 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 3.2: 1 h / 20 °C View Scheme

: 3535-37-3
3,4-dimethoxybenzoic acid chloride

: 10605-02-4
palmatine chloride

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: potassium tert-butylate / tetrahydrofuran / 2 h / 20 °C / Reflux 1.2: 3 h / 0 - 20 °C 2.1: C14H22O4Rh / water / 24 h / 100 °C / Sealed tube; Green chemistry 3.1: bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] / 2 h / 100 °C 4.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 4.2: 1 h / 20 °C View Scheme

: 67-66-3
chloroform

: 10605-02-4
palmatine chloride

: 50932-23-5
8-trichloromethyl-7,8-dihydropalmatine

Conditions

Conditions	Yield
With ammonium hydroxide for 24h;	100%
With ammonium hydroxide at 20℃; for 24h;	74.9%

: 10605-02-4
palmatine chloride

: C17H14NO4(1+)*Br(1-)

Conditions

Conditions	Yield
With hydrogen bromide Heating;	100%

: 109-97-7
pyrrole

: 10605-02-4
palmatine chloride

: 1106994-66-4
8-(pyrrol-1-yl)-7,8-dihydropalmatine

Conditions

Conditions	Yield
Stage #1: pyrrole With sodium hydride In tetrahydrofuran Sonication; Inert atmosphere; Stage #2: palmatine chloride In tetrahydrofuran at 20℃; for 5h; Inert atmosphere;	98%

: 10605-02-4
palmatine chloride

: 16705-04-7
Palmatrubine hydrochloride

Conditions

Conditions	Yield
at 180℃; Microwave irradiation;	95%
Stage #1: palmatine chloride at 195℃; for 0.25h; Stage #2: With hydrogenchloride In ethanol at 20℃; for 1h;	94%
Stage #1: palmatine chloride at 195 - 210℃; Stage #2: With hydrogenchloride In ethanol; water	86%

: 67-56-1
methanol

: 10605-02-4
palmatine chloride

: 60229-93-8
8-methoxy-7,8-dihydropalmatine

Conditions

Conditions	Yield
With sodium methylate for 24h;	90%

: 288-32-4
1H-imidazole

: 10605-02-4
palmatine chloride

: 1106994-78-8
8-(imidazol-1-yl)-7,8-dihydropalmatine

Conditions

Conditions	Yield
Stage #1: 1H-imidazole With sodium hydride In tetrahydrofuran Sonication; Inert atmosphere; Stage #2: palmatine chloride In tetrahydrofuran at 20℃; for 17.5h; Inert atmosphere;	88%

: 10605-02-4
palmatine chloride

: 81290-20-2
(trifluoromethyl)trimethylsilane

: (±)-8-trifluoromethyldihydropalmatine

Conditions

Conditions	Yield
With cesium fluoride In dichloromethane at 40℃; for 48h;	86.1%

: 10605-02-4
palmatine chloride

: 26067-60-7
dihydropalmatine

Conditions

Conditions	Yield
With methanol; sodium tetrahydroborate; potassium carbonate at 20℃; for 3h;	81.1%
With sodium tetrahydroborate; potassium carbonate; sodium hydroxide In methanol at 20℃; for 3h;	79%
With sodium tetrahydroborate; potassium carbonate; sodium hydroxide In methanol at 20℃; for 3h;	79%
With methanol; sodium tetrahydroborate; potassium carbonate Reflux;	54%

: 288-88-0
1,2,4-Triazole

: 10605-02-4
palmatine chloride

: 1106994-81-3
8-(1,2,4-triazol-1-yl)-7,8-dihydropalmatine

Conditions

Conditions	Yield
Stage #1: 1,2,4-Triazole With sodium hydride In tetrahydrofuran Sonication; Inert atmosphere; Stage #2: palmatine chloride In tetrahydrofuran at 20℃; for 17.5h; Inert atmosphere;	74%

: 10075-50-0
5-bromo-1H-indole

: 10605-02-4
palmatine chloride

: 1407154-42-0
8-(5-bromoindol-1-yl)-7,8-dihydropalmatine

Conditions

Conditions	Yield
Stage #1: 5-bromo-1H-indole With sodium hydride In tetrahydrofuran for 0.25h; Inert atmosphere; Sonication; Stage #2: palmatine chloride In tetrahydrofuran at 20℃; Inert atmosphere;	73%

: 288-13-1
NH-pyrazole

: 10605-02-4
palmatine chloride

: 1106994-75-5
8-(pyrazol-1-yl)-7,8-dihydropalmatine

Conditions

Conditions	Yield
Stage #1: NH-pyrazole With sodium hydride In tetrahydrofuran Sonication; Inert atmosphere; Stage #2: palmatine chloride In tetrahydrofuran at 20℃; for 3h; Inert atmosphere;	63%

: 131543-46-9
Glyoxal

: 10605-02-4
palmatine chloride

: C23H22NO4(1+)*Cl(1-)

Conditions

Conditions	Yield
Stage #1: palmatine chloride With sodium tetrahydroborate; potassium carbonate; sodium hydroxide In methanol at 20℃; for 3h; Stage #2: Glyoxal With acetic acid In acetonitrile for 6h; Reflux; Stage #3: With hydrogenchloride In methanol; water at 20℃; for 24h;	62%

: 124-41-4
sodium methylate

: 10605-02-4
palmatine chloride

: 112435-30-0
5,6-dihydro-2,3,8,9-10-pentamethoxydibenzoquinolizinium-13-olate

Conditions

Conditions	Yield
With oxygen; rose bengal In methanol at 0℃; for 0.333333h; Irradiation;	60%

: 10605-02-4
palmatine chloride

: 16176-68-4
palmatrubine

Conditions

Conditions	Yield
at 190℃; under 10 - 15 Torr; for 7h;	59%

: 10605-02-4
palmatine chloride

: 2393-23-9
4-methoxy-benzylamine

: 2,3,10‐trimethoxy‐9‐p‐methoxybenzylaminoprotopalmatine chloride

Conditions

Conditions	Yield
at 110℃; for 6h;	57%

: 10605-02-4
palmatine chloride

: 67-64-1
acetone

: 38699-74-0
(±)-8-acetonyldihydropalmatine

Conditions

Conditions	Yield
With sodium hydroxide In water at 20℃; for 3h;	54.9%
With sodium hydroxide In water for 0.5h;

: 10605-02-4
palmatine chloride

: 140-75-0
para-fluorobenzylamine

: 2,3,10‐trimethoxy‐9‐p‐fluorobenzylaminoprotopalmatine chloride

Conditions

Conditions	Yield
at 110℃; for 7h;	54%

: 15861-24-2
1H-indole-5-carbonitrile

: 10605-02-4
palmatine chloride

: 1407154-43-1
8-(5-cyanoindol-1-yl)-7,8-dihydropalmatine

Conditions

Conditions	Yield
Stage #1: 1H-indole-5-carbonitrile With sodium hydride In tetrahydrofuran for 0.25h; Inert atmosphere; Sonication; Stage #2: palmatine chloride In tetrahydrofuran at 20℃; Inert atmosphere;	53%

: 271-63-6
7-Azaindole

: 10605-02-4
palmatine chloride

: 1407154-44-2
8-(7-azaindol-1-yl)-7,8-dihydropalmatine

Conditions

Conditions	Yield
Stage #1: 7-Azaindole With sodium hydride In tetrahydrofuran for 0.25h; Inert atmosphere; Sonication; Stage #2: palmatine chloride In tetrahydrofuran at 20℃; Inert atmosphere;	52%

: 20781-20-8
2,4-Dimethoxybenzylamine

: 10605-02-4
palmatine chloride

: 2,3,10‐trimethoxy‐9‐o,p‐dimethoxybenzylaminoprotopalmatine chloride

Conditions

Conditions	Yield
at 110℃; for 6h;	52%

: 10605-02-4
palmatine chloride

: 104-84-7
para-methylbenzylamine

: 2,3,10‐trimethoxy‐9‐p‐methylbenzylaminoprotopalmatine chloride

Conditions

Conditions	Yield
at 110℃; for 4h;	48%

: 3959-07-7
4-Bromobenzylamine

: 10605-02-4
palmatine chloride

: 2,3,10‐trimethoxy‐9‐p‐bromobenzylaminoprotopalmatine chloride

Conditions

Conditions	Yield
at 110℃; for 7h;	44%

: 10605-02-4
palmatine chloride

: 100-81-2
3-methyl-benzenemethanamine

: 2,3,10‐trimethoxy‐9‐m‐methylbenzylaminoprotopalmatine chloride

Conditions

Conditions	Yield
at 110℃; for 4h;	43%

: 10605-02-4
palmatine chloride

: 100-46-9
benzylamine

: 2,3,10‐trimethoxy‐9‐benzylaminoprotopalmatine chloride

Conditions

Conditions	Yield
at 110℃; for 6h;	41%

Palmatine chloride Specification

The Palmatine chloride, with CAS registry number 10605-02-4, has the systematic name of 2,3,9,10-tetramethoxy-5,6-dihydroisoquino[3,2-a]isoquinolinium chloride. This chemical has the related registry number of 3486-67-7 (Parent). And this chemical should be stored in cool, dry place.

Physical properties of Palmatine chloride: (1)ACD/LogP: -1.12; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1.12; (4)ACD/LogD (pH 7.4): -1.12; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 5.88; (8)ACD/KOC (pH 7.4): 5.88; (9)#H bond acceptors: 5; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 40.8 Å².

Uses of Palmatine chloride: it can be used to produce 5,6-dihydro-2,3,8,9-10-pentamethoxydibenzo[a,g]quinolizinium-13-olate. This reaction will need reagents 1 % rose bengal, oxygen and solvent methanol. The reaction time is 20 min with reaction temperature of 0 ℃. The yield is about 60%.

You can still convert the following datas into molecular structure:
(1)SMILES: [Cl-].O(c4cc3c2cc1ccc(OC)c(OC)c1c[n+]2CCc3cc4OC)C
(2)InChI: InChI=1/C21H22NO4.ClH/c1-23-18-6-5-13-9-17-15-11-20(25-3)19(24-2)10-14(15)7-8-22(17)12-16(13)21(18)26-4;/h5-6,9-12H,7-8H2,1-4H3;1H/q+1;/p-1
(3)InChIKey: RLQYRXCUPVKSAW-REWHXWOFAH
(4)Std. InChI: InChI=1S/C21H22NO4.ClH/c1-23-18-6-5-13-9-17-15-11-20(25-3)19(24-2)10-14(15)7-8-22(17)12-16(13)21(18)26-4;/h5-6,9-12H,7-8H2,1-4H3;1H/q+1;/p-1
(5)Std. InChIKey: RLQYRXCUPVKSAW-UHFFFAOYSA-M

Product Name

Palmatine chloride

Synthetic route

Palmatine chloride Specification

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