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Cas Database

10097-84-4

10097-84-4

10097-84-4

Identification

  • Product Name:Tetrahydropalmatine

  • CAS Number: 10097-84-4

  • EINECS:1592732-453-0

  • Molecular Weight:355.434

  • Molecular Formula: C21H25NO4

  • HS Code:29339900

  • Mol File:10097-84-4.mol

Synonyms:Rotundine;5,8,13,13a-Tetrahydro-2,3,9,10-tetramethoxy-6H-dibenzo[a,g] quinolizine;

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Chemical Properties

  • Appearance/Colour:light yellow powder crystal

  • Boiling Point: 482.9 °C at 760 mmHg

  • Flash Point:138.7 °C

  • Density: 1.23 g/cm3

  • Solubility:Chloroform (Slightly), Methanol (Slightly)

  • Storage Temp.:Hygroscopic, Refrigerator, under inert atmosphere

  • Vapor Pressure: 1.76E-09mmHg at 25°C

  • Refractive Index: 1.608

  • PSA: 40.16000

  • LogP: 3.31440

Safety information and MSDS view more

  • Signal Word:no data available

  • Hazard Statement:no data available

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price view more

  • Manufacture/Brand
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  • Manufacture/Brand:Usbiological
  • Product Description:Tetrahydropalmatine
  • Packaging:20mg
  • Price:$ 263
  • Delivery:In stock
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  • Manufacture/Brand:JR MediChem
  • Product Description:Rotundine(NewProduct) 98%(HPLC)
  • Packaging:100mg
  • Price:$ 108
  • Delivery:In stock
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  • Manufacture/Brand:DC Chemicals
  • Product Description:Rotundine >98%,StandardReferencesGrade
  • Packaging:20 mg
  • Price:$ 280
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  • Manufacture/Brand:Biorbyt Ltd
  • Product Description:Rotundine >98%,Standard References Grade
  • Packaging:20 mg
  • Price:$ 569.5
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  • Manufacture/Brand:Biorbyt Ltd
  • Product Description:Rotundine 98%
  • Packaging:100 mg
  • Price:$ 255
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  • Manufacture/Brand:Biorbyt Ltd
  • Product Description:Rotundine 98%
  • Packaging:20 mg
  • Price:$ 207.4
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  • Manufacture/Brand:Arctom
  • Product Description:Rotundine ≥98%
  • Packaging:20mg
  • Price:$ 30
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  • Manufacture/Brand:American Custom Chemicals Corporation
  • Product Description:ROTUNDINE 95.00%
  • Packaging:1G
  • Price:$ 1686.3
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  • Manufacture/Brand:American Custom Chemicals Corporation
  • Product Description:ROTUNDINE 95.00%
  • Packaging:100MG
  • Price:$ 716.1
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Relevant articles and documentsAll total 10 Articles be found

Studies on the alkaloids of Menispermaceous plants. 233. Alkaloids of Tinomiscium petiolare Miers

Tomita,Furutawa

, p. 881 - 882 (1967)

-

-

Schmutz

, p. 335,342 (1959)

-

Method for synthesizing tetrahydroberberine and derivatives thereof

-

Paragraph 0094-0099, (2021/07/08)

The invention provides a method for synthesizing tetrahydroberberine and derivatives thereof. Specifically, in the presence of an iridium metal catalyst precursor, a chiral diphosphine ligand, an acid and a halogen-containing additive, in a hydrogen atmosphere, a compound (II) is subjected to an asymmetric catalytic hydrogenation reaction in an organic solvent so as to prepare the compound (I).

Asymmetric synthesis of (S)-(-)-tetrahydropalmatine and (S)-(-)-canadine via a sulfinyl-directed Pictet-Spengler cyclization

Mastranzo, Virginia M.,Olivares Romero, José Luis,Yuste, Francisco,Ortiz, Benjamín,Sánchez-Obregón, Rubén,García Ruano, José L.

, p. 1266 - 1271 (2012/02/15)

(S)-(-)-Tetrahydropalmatine 2 and (S)-(-)-canadine 4 were synthesized in three steps from (S)-6, in 33% and 34% overall yield, respectively. Thus, condensation of the (S)-(E)-sulfinylimines 10 and 11 with the carbanion derived from (S)-6 gave the tetrahydroisoquinolines 12 and 13, respectively, which upon TFA induced N-desulfinylation, and subsequent microwave assisted Pictet-Spengler cyclization effected both cyclization and C-desulfinylation producing (S)-(-)-tetrahydropalmatine 2 and (S)-(-)-canadine 4 in optically pure form.

Process route upstream and downstream products

Process route

2,3,9,10-tetramethoxy-5,8-dihydro-6H-isoquinolino[3,2-α]isoquinoline
26067-60-7

2,3,9,10-tetramethoxy-5,8-dihydro-6H-isoquinolino[3,2-α]isoquinoline

tetrahydropalmatine
483-14-7,2934-97-6,3520-14-7,10097-84-4,84-38-8

tetrahydropalmatine

Conditions
Conditions Yield
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; (R,R)-1,1'-bis{(R)-4,5-dihydro-3H-dinaphtho[1,2-c:2',1'-e]-phosphepino}ferrocene; hydrogen; acetic acid; potassium bromide; In dichloromethane; at 25 ℃; for 72h; under 60804.1 Torr; enantioselective reaction; Inert atmosphere;
95%
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; hydrogen; 1,1'-bis{(S)-4,5-dihydro-3H-binaphtho[1,2-C:2',1'-e]phosphino}ferrocene; acetic acid; potassium bromide; In dichloromethane; at 20 ℃; for 100h; under 45603.1 Torr; Autoclave;
94%
formaldehyd
50-00-0,30525-89-4,61233-19-0

formaldehyd

(1S)-1-[3,4-dimethoxy-2-(S)-p-tolylsulfinyl]benzyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
1356336-76-9

(1S)-1-[3,4-dimethoxy-2-(S)-p-tolylsulfinyl]benzyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

tetrahydropalmatine
483-14-7,2934-97-6,3520-14-7,10097-84-4,84-38-8

tetrahydropalmatine

Conditions
Conditions Yield
formaldehyd; (1S)-1-[3,4-dimethoxy-2-(S)-p-tolylsulfinyl]benzyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline; With trifluoroacetic acid; In toluene; at 140 ℃; for 0.5h; Microwave irradiation;
With sodium hydroxide; In water; pH=8;
56%
C<sub>21</sub>H<sub>26</sub>ClNO<sub>4</sub>

C21H26ClNO4

tetrahydropalmatine
483-14-7,2934-97-6,3520-14-7,10097-84-4,84-38-8

tetrahydropalmatine

Conditions
Conditions Yield
With sodium hydrogencarbonate; In dichloromethane; at 20 ℃; for 1.5h;
247 mg
(13aS)-2,3,9,10-tetramethoxy-5,8,13,13a-tetrahydro-6H-dibenzo[a,g]quinolizin-5-ol
870282-81-8

(13aS)-2,3,9,10-tetramethoxy-5,8,13,13a-tetrahydro-6H-dibenzo[a,g]quinolizin-5-ol

tetrahydropalmatine
483-14-7,2934-97-6,3520-14-7,10097-84-4,84-38-8

tetrahydropalmatine

Conditions
Conditions Yield
With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; at -78 - 20 ℃; for 19h;
92%
[1-(3,4-dimethoxyphenyl)-meth-(1E)-ylidene]-((2R)-2-methoxymethylpyrrolidin-1-yl)-amine
870282-77-2

[1-(3,4-dimethoxyphenyl)-meth-(1E)-ylidene]-((2R)-2-methoxymethylpyrrolidin-1-yl)-amine

tetrahydropalmatine
483-14-7,2934-97-6,3520-14-7,10097-84-4,84-38-8

tetrahydropalmatine

Conditions
Conditions Yield
Multi-step reaction with 5 steps
1.1: s-BuLi; TMEDA / diethyl ether; tetrahydrofuran; hexane / -78 - -40 °C
1.2: 54 percent / trimethylaluminum / various solvents / 17 h / -40 °C
2.1: BH3*THF / tetrahydrofuran / 4 h / Heating
2.2: 83 percent / aqueous HCl / tetrahydrofuran / 0.02 h / Heating
3.1: 94 percent / methanol / 22 h / Heating
4.1: TFAA; TFA / toluene / 15 h / Heating
5.1: Raney nickel W2; hydrogen / ethanol / 22 h / Heating
With borane-THF; N,N,N,N,-tetramethylethylenediamine; Raney nickel W2; hydrogen; sec.-butyllithium; trifluoroacetic acid; trifluoroacetic anhydride; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; toluene; 3.1: Michael reaction / 4.1: Pummerer reaction;
Multi-step reaction with 5 steps
1.1: s-BuLi; TMEDA / diethyl ether; tetrahydrofuran; hexane / -78 - -40 °C
1.2: 54 percent / trimethylaluminum / various solvents / 17 h / -40 °C
2.1: BH3*THF / tetrahydrofuran / 4 h / Heating
2.2: 83 percent / aqueous HCl / tetrahydrofuran / 0.02 h / Heating
3.1: 64 percent / K2CO3; KI / dimethylformamide / 24 h / 110 °C
4.1: 83 percent / aqueous HCl / acetone / 0 - 20 °C
5.1: 92 percent / BF3*OEt2; Et3SiH / CH2Cl2 / 19 h / -78 - 20 °C
With hydrogenchloride; triethylsilane; borane-THF; N,N,N,N,-tetramethylethylenediamine; boron trifluoride diethyl etherate; sec.-butyllithium; potassium carbonate; potassium iodide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; 4.1: Pomeranz-Fritsch reaction;
(3S)-3-(3,4-dimethoxyphenyl)-7,8-dimethoxy-1,2,3,4-tetrahydroisoquinoline
870282-79-4

(3S)-3-(3,4-dimethoxyphenyl)-7,8-dimethoxy-1,2,3,4-tetrahydroisoquinoline

tetrahydropalmatine
483-14-7,2934-97-6,3520-14-7,10097-84-4,84-38-8

tetrahydropalmatine

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: 94 percent / methanol / 22 h / Heating
2: TFAA; TFA / toluene / 15 h / Heating
3: Raney nickel W2; hydrogen / ethanol / 22 h / Heating
With Raney nickel W2; hydrogen; trifluoroacetic acid; trifluoroacetic anhydride; In methanol; ethanol; toluene; 1: Michael reaction / 2: Pummerer reaction;
Multi-step reaction with 3 steps
1: 64 percent / K2CO3; KI / dimethylformamide / 24 h / 110 °C
2: 83 percent / aqueous HCl / acetone / 0 - 20 °C
3: 92 percent / BF3*OEt2; Et3SiH / CH2Cl2 / 19 h / -78 - 20 °C
With hydrogenchloride; triethylsilane; boron trifluoride diethyl etherate; potassium carbonate; potassium iodide; In dichloromethane; N,N-dimethyl-formamide; acetone; 2: Pomeranz-Fritsch reaction;
(3S)-3-(3,4-dimethoxyphenyl)-7,8-dimethoxy-2-((2R)-2-methoxymethylpyrrolidin-1-yl)-3,4-dihydro-2H-isoquinolin-1-one
870282-78-3

(3S)-3-(3,4-dimethoxyphenyl)-7,8-dimethoxy-2-((2R)-2-methoxymethylpyrrolidin-1-yl)-3,4-dihydro-2H-isoquinolin-1-one

tetrahydropalmatine
483-14-7,2934-97-6,3520-14-7,10097-84-4,84-38-8

tetrahydropalmatine

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1.1: BH3*THF / tetrahydrofuran / 4 h / Heating
1.2: 83 percent / aqueous HCl / tetrahydrofuran / 0.02 h / Heating
2.1: 94 percent / methanol / 22 h / Heating
3.1: TFAA; TFA / toluene / 15 h / Heating
4.1: Raney nickel W2; hydrogen / ethanol / 22 h / Heating
With borane-THF; Raney nickel W2; hydrogen; trifluoroacetic acid; trifluoroacetic anhydride; In tetrahydrofuran; methanol; ethanol; toluene; 2.1: Michael reaction / 3.1: Pummerer reaction;
Multi-step reaction with 4 steps
1.1: BH3*THF / tetrahydrofuran / 4 h / Heating
1.2: 83 percent / aqueous HCl / tetrahydrofuran / 0.02 h / Heating
2.1: 64 percent / K2CO3; KI / dimethylformamide / 24 h / 110 °C
3.1: 83 percent / aqueous HCl / acetone / 0 - 20 °C
4.1: 92 percent / BF3*OEt2; Et3SiH / CH2Cl2 / 19 h / -78 - 20 °C
With hydrogenchloride; triethylsilane; borane-THF; boron trifluoride diethyl etherate; potassium carbonate; potassium iodide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone; 3.1: Pomeranz-Fritsch reaction;
N,N-diethyl-2,3-dimethoxy-6-methyl-benzamide
70945-99-2

N,N-diethyl-2,3-dimethoxy-6-methyl-benzamide

tetrahydropalmatine
483-14-7,2934-97-6,3520-14-7,10097-84-4,84-38-8

tetrahydropalmatine

Conditions
Conditions Yield
Multi-step reaction with 5 steps
1.1: s-BuLi; TMEDA / diethyl ether; tetrahydrofuran; hexane / -78 - -40 °C
1.2: 54 percent / trimethylaluminum / various solvents / 17 h / -40 °C
2.1: BH3*THF / tetrahydrofuran / 4 h / Heating
2.2: 83 percent / aqueous HCl / tetrahydrofuran / 0.02 h / Heating
3.1: 94 percent / methanol / 22 h / Heating
4.1: TFAA; TFA / toluene / 15 h / Heating
5.1: Raney nickel W2; hydrogen / ethanol / 22 h / Heating
With borane-THF; N,N,N,N,-tetramethylethylenediamine; Raney nickel W2; hydrogen; sec.-butyllithium; trifluoroacetic acid; trifluoroacetic anhydride; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; toluene; 3.1: Michael reaction / 4.1: Pummerer reaction;
Multi-step reaction with 5 steps
1.1: s-BuLi; TMEDA / diethyl ether; tetrahydrofuran; hexane / -78 - -40 °C
1.2: 54 percent / trimethylaluminum / various solvents / 17 h / -40 °C
2.1: BH3*THF / tetrahydrofuran / 4 h / Heating
2.2: 83 percent / aqueous HCl / tetrahydrofuran / 0.02 h / Heating
3.1: 64 percent / K2CO3; KI / dimethylformamide / 24 h / 110 °C
4.1: 83 percent / aqueous HCl / acetone / 0 - 20 °C
5.1: 92 percent / BF3*OEt2; Et3SiH / CH2Cl2 / 19 h / -78 - 20 °C
With hydrogenchloride; triethylsilane; borane-THF; N,N,N,N,-tetramethylethylenediamine; boron trifluoride diethyl etherate; sec.-butyllithium; potassium carbonate; potassium iodide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; 4.1: Pomeranz-Fritsch reaction;
3,4-dimethoxy-benzaldehyde
120-14-9

3,4-dimethoxy-benzaldehyde

tetrahydropalmatine
483-14-7,2934-97-6,3520-14-7,10097-84-4,84-38-8

tetrahydropalmatine

Conditions
Conditions Yield
Multi-step reaction with 6 steps
1.1: 100 percent / diethyl ether / 0 - 20 °C
2.1: s-BuLi; TMEDA / diethyl ether; tetrahydrofuran; hexane / -78 - -40 °C
2.2: 54 percent / trimethylaluminum / various solvents / 17 h / -40 °C
3.1: BH3*THF / tetrahydrofuran / 4 h / Heating
3.2: 83 percent / aqueous HCl / tetrahydrofuran / 0.02 h / Heating
4.1: 94 percent / methanol / 22 h / Heating
5.1: TFAA; TFA / toluene / 15 h / Heating
6.1: Raney nickel W2; hydrogen / ethanol / 22 h / Heating
With borane-THF; N,N,N,N,-tetramethylethylenediamine; Raney nickel W2; hydrogen; sec.-butyllithium; trifluoroacetic acid; trifluoroacetic anhydride; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; toluene; 4.1: Michael reaction / 5.1: Pummerer reaction;
Multi-step reaction with 6 steps
1.1: 100 percent / diethyl ether / 0 - 20 °C
2.1: s-BuLi; TMEDA / diethyl ether; tetrahydrofuran; hexane / -78 - -40 °C
2.2: 54 percent / trimethylaluminum / various solvents / 17 h / -40 °C
3.1: BH3*THF / tetrahydrofuran / 4 h / Heating
3.2: 83 percent / aqueous HCl / tetrahydrofuran / 0.02 h / Heating
4.1: 64 percent / K2CO3; KI / dimethylformamide / 24 h / 110 °C
5.1: 83 percent / aqueous HCl / acetone / 0 - 20 °C
6.1: 92 percent / BF3*OEt2; Et3SiH / CH2Cl2 / 19 h / -78 - 20 °C
With hydrogenchloride; triethylsilane; borane-THF; N,N,N,N,-tetramethylethylenediamine; boron trifluoride diethyl etherate; sec.-butyllithium; potassium carbonate; potassium iodide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; 5.1: Pomeranz-Fritsch reaction;
1,2,3,4-tetrahydro-6,7-dimethoxy-1-<2-((((1-dimethylethyl)dimethylsilyl)oxy)methyl)-3,4-dimethoxbenzyl>isoquinoline

1,2,3,4-tetrahydro-6,7-dimethoxy-1-<2-((((1-dimethylethyl)dimethylsilyl)oxy)methyl)-3,4-dimethoxbenzyl>isoquinoline

tetrahydropalmatine
483-14-7,2934-97-6,3520-14-7,10097-84-4,84-38-8

tetrahydropalmatine

Conditions
Conditions Yield
With bromine; triphenylphosphine; In dichloromethane; for 14h; Yield given; Ambient temperature;

10097-84-4 Upstream products

10097-84-4 Downstream products

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