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476-70-0

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476-70-0 Usage

Uses

Different sources of media describe the Uses of 476-70-0 differently. You can refer to the following data:
1. antineoplastic
2. boldine is attributed with strong anti-oxidant properties. It has also demonstrated an ability to protect against uVB rays. Boldine is a constituent of the boldo plant (Peumus boldus Mol.) native to Chile, and is found in the plant’s leaves and bark.

Check Digit Verification of cas no

The CAS Registry Mumber 476-70-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,7 and 6 respectively; the second part has 2 digits, 7 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 476-70:
(5*4)+(4*7)+(3*6)+(2*7)+(1*0)=80
80 % 10 = 0
So 476-70-0 is a valid CAS Registry Number.
InChI:InChI=1/C19H21NO4/c1-20-5-4-10-7-15(22)19(24-3)18-12-9-16(23-2)14(21)8-11(12)6-13(20)17(10)18/h7-9,13,21-22H,4-6H2,1-3H3

476-70-0 Well-known Company Product Price

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  • Sigma-Aldrich

  • (Y0000434)  Boldine  European Pharmacopoeia (EP) Reference Standard

  • 476-70-0

  • Y0000434

  • 1,880.19CNY

  • Detail

476-70-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name (6aS)-1,10-dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-2,9-diol

1.2 Other means of identification

Product number -
Other names Boldine chloroform

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:476-70-0 SDS

476-70-0Synthetic route

formaldehyd
50-00-0

formaldehyd

formic acid
64-18-6

formic acid

(+)-laurolitsine

(+)-laurolitsine

boldine
476-70-0

boldine

Conditions
ConditionsYield
With water
5-Chloro-1-phenyltetrazole
14210-25-4

5-Chloro-1-phenyltetrazole

boldine
476-70-0

boldine

2,9-O,O-bis(1-phenyl-1H-tetrazol-5-yl)boldine
65979-75-1

2,9-O,O-bis(1-phenyl-1H-tetrazol-5-yl)boldine

Conditions
ConditionsYield
With potassium carbonate In acetonitrile for 24h; Heating / reflux;96%
With potassium carbonate; potassium iodide In acetonitrile at 90℃; for 24h;80%
phenyltrimethylammonium chloride
138-24-9

phenyltrimethylammonium chloride

boldine
476-70-0

boldine

glaucine
475-81-0

glaucine

Conditions
ConditionsYield
With potassium tert-butylate In N,N-dimethyl-formamide at 90℃; for 16h;87%
2-iodo-propane
75-30-9

2-iodo-propane

boldine
476-70-0

boldine

2,9-diisopropyloxy-1,10-dimethoxy-N-methylaporphine

2,9-diisopropyloxy-1,10-dimethoxy-N-methylaporphine

Conditions
ConditionsYield
With potassium carbonate In ethanol at 70℃; for 9h;75%
boldine
476-70-0

boldine

(+)-Predicentrine
20051-87-0, 517-65-7

(+)-Predicentrine

Conditions
ConditionsYield
In diethyl ether at 20℃; for 24h;65%
boldine
476-70-0

boldine

A

3,8-Dibromoboldine
63955-80-6

3,8-Dibromoboldine

B

3-bromoboldine

3-bromoboldine

Conditions
ConditionsYield
With bromine; acetic acid In chloroform at 20℃; Bromination;A 64%
B 9%
With N-Bromosuccinimide; trifluoroacetic acid In chloroform at 20℃; for 1h; Bromination;A 54%
B 13%
boldine
476-70-0

boldine

(S)-8-NO-boldine
352670-72-5

(S)-8-NO-boldine

Conditions
ConditionsYield
With sodium nitrite In acetic acid at 20℃; for 1h;64%
trifluoroacetic acid
76-05-1

trifluoroacetic acid

boldine
476-70-0

boldine

methyl iodide
74-88-4

methyl iodide

A

N-methylsecoboldine trifluoroacetate
1346153-51-2

N-methylsecoboldine trifluoroacetate

B

N,N-dimethylsecoboldine trifluoroacetate
1346153-52-3

N,N-dimethylsecoboldine trifluoroacetate

C

N-methylboldine trifluoroacetate
1346153-50-1

N-methylboldine trifluoroacetate

Conditions
ConditionsYield
Stage #1: boldine; methyl iodide In methanol; acetonitrile at 20℃; for 6h;
Stage #2: trifluoroacetic acid In methanol; water; acetonitrile for 1h;
A 7%
B 3%
C 51%
boldine
476-70-0

boldine

A

3-chloroboldine

3-chloroboldine

B

(S)-3,8-Dichloroboldine

(S)-3,8-Dichloroboldine

Conditions
ConditionsYield
With N-chloro-succinimide; trifluoroacetic acid In chloroform at 22℃; for 1h; Chlorination;A 48%
B 19%
boldine
476-70-0

boldine

3-iodoboldine

3-iodoboldine

Conditions
ConditionsYield
With N-iodo-succinimide; trifluoroacetic acid In chloroform at 20℃; for 2h; Iodination;47%
N,N-phenylbistrifluoromethane-sulfonimide
37595-74-7

N,N-phenylbistrifluoromethane-sulfonimide

phenyltrimethylammonium chloride
138-24-9

phenyltrimethylammonium chloride

boldine
476-70-0

boldine

A

(S)-1,2,10-trimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-9-yl-trifluoro-methanesulfonate

(S)-1,2,10-trimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-9-yl-trifluoro-methanesulfonate

B

predicentrine triflate

predicentrine triflate

Conditions
ConditionsYield
Stage #1: phenyltrimethylammonium chloride; boldine With potassium tert-butylate In N,N-dimethyl-formamide at 90℃; for 12h;
Stage #2: N,N-phenylbistrifluoromethane-sulfonimide With TEA; potassium carbonate In dichloromethane for 72h; Further stages.;
A 36%
B 38%
boldine
476-70-0

boldine

3-Bromoboldine

3-Bromoboldine

Conditions
ConditionsYield
With N-Bromosuccinimide In trifluoroacetic acid at 20℃; for 3h;35.9%
methanol
67-56-1

methanol

boldine
476-70-0

boldine

A

(+)-Predicentrine
20051-87-0, 517-65-7

(+)-Predicentrine

B

N-methyllaurotetanine
2169-44-0

N-methyllaurotetanine

C

glaucine
475-81-0

glaucine

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; Inert atmosphere;A n/a
B n/a
C 26%
boldine
476-70-0

boldine

(S)-1,10-Dimethoxy-6-methyl-6-oxy-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-2,9-diol
104385-34-4

(S)-1,10-Dimethoxy-6-methyl-6-oxy-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-2,9-diol

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In chloroform for 2h; Heating;20%
boldine
476-70-0

boldine

(+)-<3,8-3H2>boldine

(+)-<3,8-3H2>boldine

Conditions
ConditionsYield
With tritium oxide; potassium tert-butylate at 100℃; for 110h; sealed tube;
pivaloyl chloride
3282-30-2

pivaloyl chloride

boldine
476-70-0

boldine

2,9-O,O'-dipivaloylboldine

2,9-O,O'-dipivaloylboldine

boldine
476-70-0

boldine

A

(+)-Predicentrine
20051-87-0, 517-65-7

(+)-Predicentrine

B

glaucine
475-81-0

glaucine

Conditions
ConditionsYield
In methanol; diethyl ether
phenyltrimethylammonium iodide
98-04-4

phenyltrimethylammonium iodide

boldine
476-70-0

boldine

A

(+)-Predicentrine
20051-87-0, 517-65-7

(+)-Predicentrine

B

glaucine
475-81-0

glaucine

allyl bromide
106-95-6

allyl bromide

boldine
476-70-0

boldine

N-allylsecoboldine

N-allylsecoboldine

Conditions
ConditionsYield
Heating;
In N,N-dimethyl-formamide at 100 - 110℃; for 2h;
In N,N-dimethyl-formamide at 100 - 110℃; for 2h;
phenyltrimethylammonium chloride
138-24-9

phenyltrimethylammonium chloride

boldine
476-70-0

boldine

A

(+)-Predicentrine
20051-87-0, 517-65-7

(+)-Predicentrine

B

N-methyllaurotetanine
2169-44-0

N-methyllaurotetanine

Conditions
ConditionsYield
With potassium tert-butylate In N,N-dimethyl-formamide at 90℃; for 12h; Title compound not separated from byproducts.;
boldine
476-70-0

boldine

acetic acid 7-acetoxy-1-[2-(allyl-methyl-amino)-ethyl]-4,6-dimethoxy-phenanthren-3-yl ester

acetic acid 7-acetoxy-1-[2-(allyl-methyl-amino)-ethyl]-4,6-dimethoxy-phenanthren-3-yl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Heating
2: pyridine
View Scheme
boldine
476-70-0

boldine

3-chloro-1,2,9,10-tetramethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline

3-chloro-1,2,9,10-tetramethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: methanol; diethyl ether
2: 24 percent / N-chlorosuccinimide; trifluoroacetic acid / 2 h / 20 °C
View Scheme
boldine
476-70-0

boldine

3-iodo-1,9,10-trimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-2-ol

3-iodo-1,9,10-trimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-2-ol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: methanol; diethyl ether
2: 49 percent / N-iodosuccinimide; trifluoroacetic acid / 2 h / 20 °C
View Scheme
boldine
476-70-0

boldine

3-iodo-1,2,9,10-tetramethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline

3-iodo-1,2,9,10-tetramethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: methanol; diethyl ether
2: 26 percent / N-iodosuccinimide; trifluoroacetic acid / 2 h / 20 °C
View Scheme
boldine
476-70-0

boldine

(S)-3,8-Dichloroglaucine

(S)-3,8-Dichloroglaucine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: methanol; diethyl ether
2: 27 percent / N-chlorosuccinimide; trifluoroacetic acid / 2 h / 20 °C
View Scheme
boldine
476-70-0

boldine

3,8-dibromo-1,9,10-trimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-2-ol

3,8-dibromo-1,9,10-trimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-2-ol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: methanol; diethyl ether
2: 24 percent / N-bromosuccinimide; trifluoroacetic acid / 2 h / 20 °C
View Scheme
boldine
476-70-0

boldine

3-bromopredicentrine
87167-04-2

3-bromopredicentrine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: methanol; diethyl ether
2: 55 percent / N-bromosuccinimide; trifluoroacetic acid / 2 h / 20 °C
View Scheme
boldine
476-70-0

boldine

3,8-dibromoglaucine
121387-31-3

3,8-dibromoglaucine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: methanol; diethyl ether
2: 47 percent / N-bromosuccinimide; trifluoroacetic acid / 2 h / 20 °C
View Scheme
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