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66171-50-4 Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 104, p. 1428, 1982 DOI: 10.1021/ja00369a049Organic Syntheses, Coll. Vol. 4, p. 532, 1963

Check Digit Verification of cas no

The CAS Registry Mumber 66171-50-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,6,1,7 and 1 respectively; the second part has 2 digits, 5 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 66171-50:
(7*6)+(6*6)+(5*1)+(4*7)+(3*1)+(2*5)+(1*0)=124
124 % 10 = 4
So 66171-50-4 is a valid CAS Registry Number.
InChI:InChI=1/C7H7NO3/c1-11-7(10)5-2-3-6(9)8-4-5/h2-4H,1H3,(H,8,9)

66171-50-4SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Methyl 6-hydroxynicotinate

1.2 Other means of identification

Product number -
Other names METHYL 6-OXO-1,6-DIHYDRO-3-PYRIDINECARBOXYLATE

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:66171-50-4 SDS

66171-50-4Synthetic route

methanol
67-56-1

methanol

6-hydroxy-3-pyridinecarboxylic acid
5006-66-6

6-hydroxy-3-pyridinecarboxylic acid

methyl 6-hydroxynicotinate
66171-50-4

methyl 6-hydroxynicotinate

Conditions
ConditionsYield
With sulfuric acid at 65 - 70℃; for 3h;99%
With sulfuric acid for 18h; Reflux;85%
With sulfuric acid In water at 20℃; for 20h; Reflux;82%
6-hydroxy-3-pyridinecarboxylic acid
5006-66-6

6-hydroxy-3-pyridinecarboxylic acid

diazomethyl-trimethyl-silane
18107-18-1

diazomethyl-trimethyl-silane

methyl 6-hydroxynicotinate
66171-50-4

methyl 6-hydroxynicotinate

Conditions
ConditionsYield
In methanol; hexane; benzene for 2h; Ambient temperature;95%
In methanol; hexane; benzene95%
In methanol; benzene for 2h; Ambient temperature;91%
In methanol; benzene at 20℃; for 4.08333h; Product distribution / selectivity;84.9%
6-hydroxy-3-pyridinecarboxylic acid
5006-66-6

6-hydroxy-3-pyridinecarboxylic acid

A

methyl 6-hydroxynicotinate
66171-50-4

methyl 6-hydroxynicotinate

B

6-hydroxynicotinamide

6-hydroxynicotinamide

Conditions
ConditionsYield
With sulfuric acid In methanol; dichloromethaneA n/a
B 90%
methyl coumalate
6018-41-3

methyl coumalate

methyl 6-hydroxynicotinate
66171-50-4

methyl 6-hydroxynicotinate

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,1,1,3,3,3-hexamethyl-disilazane In acetonitrile at 20℃; for 48h; Inert atmosphere; Schlenk technique;70%
6-methoxy-nicotinic acid methyl ester
26218-80-4

6-methoxy-nicotinic acid methyl ester

methyl 6-hydroxynicotinate
66171-50-4

methyl 6-hydroxynicotinate

Conditions
ConditionsYield
With hexamethyldisilathiane; sodium methylate In various solvent(s) at 110℃; for 18h;40%
6-hydroxy-3-pyridinecarboxylic acid
5006-66-6

6-hydroxy-3-pyridinecarboxylic acid

methyl 6-hydroxynicotinate
66171-50-4

methyl 6-hydroxynicotinate

Conditions
ConditionsYield
With thionyl chloride behandeln des Produkts mit Methylalkohol;
With sulfuric acid In methanol
With hydrogenchloride In water
6-hydroxy-3-pyridinecarboxylic acid
5006-66-6

6-hydroxy-3-pyridinecarboxylic acid

oxalyl dichloride
79-37-8

oxalyl dichloride

methyl 6-hydroxynicotinate
66171-50-4

methyl 6-hydroxynicotinate

Conditions
ConditionsYield
In dichloromethane; ethyl acetate; N,N-dimethyl-formamide2.74 g (25%)
5-bromopyridin-2-ol
13466-38-1

5-bromopyridin-2-ol

methanol
67-56-1

methanol

carbon monoxide
201230-82-2

carbon monoxide

methyl 6-hydroxynicotinate
66171-50-4

methyl 6-hydroxynicotinate

Conditions
ConditionsYield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine at 100℃; under 3750.38 Torr; for 90h; Autoclave; Large scale;24 kg
methyl 6-hydroxynicotinate
66171-50-4

methyl 6-hydroxynicotinate

methyl 5-bromo-6-hydroxypyridine-3-carboxylate
381247-99-0

methyl 5-bromo-6-hydroxypyridine-3-carboxylate

Conditions
ConditionsYield
Stage #1: methyl 6-hydroxynicotinate With bromine; acetic acid at 60℃;
Stage #2: With sodium hydrogencarbonate; sodium hydroxide at 18 - 26℃; pH=~ 7;
100%
methyl 6-hydroxynicotinate
66171-50-4

methyl 6-hydroxynicotinate

N-(4-chloromethyl-2,3-difluoro-benzyl)-acetamide

N-(4-chloromethyl-2,3-difluoro-benzyl)-acetamide

1-[4-(acetylamino-methyl)-2,3-difluoro-benzyl]-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid methyl ester

1-[4-(acetylamino-methyl)-2,3-difluoro-benzyl]-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid methyl ester

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 35℃; for 3h;99%
methyl 6-hydroxynicotinate
66171-50-4

methyl 6-hydroxynicotinate

2-(dimethyl(oxo)-λ6-sulfaneylidene)-1-phenylethan-1-one
20718-17-6

2-(dimethyl(oxo)-λ6-sulfaneylidene)-1-phenylethan-1-one

methyl 6-oxo-1-(2-oxo-2-phenylethyl)-1,6-dihydropyridine-3-carboxylate

methyl 6-oxo-1-(2-oxo-2-phenylethyl)-1,6-dihydropyridine-3-carboxylate

Conditions
ConditionsYield
With pentamethylcyclopentadienyl bis(triphenylphosphine)ruthenium(II) chloride In dichloromethane at 60℃; for 4h; Sealed tube; Inert atmosphere;96%
methyl 6-hydroxynicotinate
66171-50-4

methyl 6-hydroxynicotinate

2-(bromomethyl)pyridine hydrobromide
31106-82-8

2-(bromomethyl)pyridine hydrobromide

methyl 6-(pyridin-2-ylmethoxy)nicotinate
1126367-44-9

methyl 6-(pyridin-2-ylmethoxy)nicotinate

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 18 - 25℃;95%
methyl 6-hydroxynicotinate
66171-50-4

methyl 6-hydroxynicotinate

ethyl iodide
75-03-6

ethyl iodide

methyl 1-ethyl-6-oxo-1,6-dihydropyridine-3-carboxylate
74925-38-5

methyl 1-ethyl-6-oxo-1,6-dihydropyridine-3-carboxylate

Conditions
ConditionsYield
In dichloromethane; acetonitrile Product distribution / selectivity;91.3%
With potassium carbonate In acetonitrile at 80℃; for 16h; Solvent; Temperature;73%
With potassium carbonate In acetonitrile at 80℃; for 16h; Solvent; Temperature;73%
methyl 6-hydroxynicotinate
66171-50-4

methyl 6-hydroxynicotinate

2,2-difluoro-2-(fluorosulfonyl)acetic acid
1717-59-5

2,2-difluoro-2-(fluorosulfonyl)acetic acid

methyl 6-(difluoromethoxy)nicotinate

methyl 6-(difluoromethoxy)nicotinate

Conditions
ConditionsYield
Stage #1: methyl 6-hydroxynicotinate With sodium hydride In acetonitrile at 20℃; for 0.5h;
Stage #2: 2,2-difluoro-2-(fluorosulfonyl)acetic acid In acetonitrile at 25℃; for 2h;
85.4%
Stage #1: methyl 6-hydroxynicotinate With sodium hydride In acetonitrile; mineral oil at 20℃; for 0.5h; Inert atmosphere;
Stage #2: 2,2-difluoro-2-(fluorosulfonyl)acetic acid In acetonitrile; mineral oil at 20℃; for 0.5h; Inert atmosphere;
73%
methyl 6-hydroxynicotinate
66171-50-4

methyl 6-hydroxynicotinate

ethyl iodide
75-03-6

ethyl iodide

methyl 6-ethoxynicotinate
74357-22-5

methyl 6-ethoxynicotinate

Conditions
ConditionsYield
With silver carbonate In benzene at 25℃; for 96h;85%
methyl 6-hydroxynicotinate
66171-50-4

methyl 6-hydroxynicotinate

N-((5-(bromomethyl)pyridin-2-yl)methyl)acetamide

N-((5-(bromomethyl)pyridin-2-yl)methyl)acetamide

methyl 1-((6-(acetamidomethyl)pyridin-3-yl)methyl)-6-oxo-1,6-dihydropyridine-3-carboxylate

methyl 1-((6-(acetamidomethyl)pyridin-3-yl)methyl)-6-oxo-1,6-dihydropyridine-3-carboxylate

Conditions
ConditionsYield
With potassium carbonate In acetone Reflux;85%
methyl 6-hydroxynicotinate
66171-50-4

methyl 6-hydroxynicotinate

6-hydroxynicotinic acid hydrazide
134531-63-8

6-hydroxynicotinic acid hydrazide

Conditions
ConditionsYield
With hydrazine In ethanol for 1h; Heating;82%
methyl 6-hydroxynicotinate
66171-50-4

methyl 6-hydroxynicotinate

3-(3-phenylpropyl-2-yn-1-ylidene)-2,4-pentanedione
67082-95-5

3-(3-phenylpropyl-2-yn-1-ylidene)-2,4-pentanedione

methyl (S)-1-((4-acetyl-5-methylfuran-2-yl)(phenyl)methyl)-6-oxo-1,6-dihydropyridine-3-carboxylate

methyl (S)-1-((4-acetyl-5-methylfuran-2-yl)(phenyl)methyl)-6-oxo-1,6-dihydropyridine-3-carboxylate

Conditions
ConditionsYield
With dirhodium(II) tetrakis[N-tetrafluorophthaloyl-(S)-tert-leucinate] In diethyl ether; Cyclopentane at 0℃; for 72h; Inert atmosphere; Molecular sieve; enantioselective reaction;82%
methyl 6-hydroxynicotinate
66171-50-4

methyl 6-hydroxynicotinate

6-hydroxy-5-iodonicotinic acid methyl ester
885950-46-9

6-hydroxy-5-iodonicotinic acid methyl ester

Conditions
ConditionsYield
With N-iodo-succinimide In N,N-dimethyl-formamide at 70℃; for 3h;81%
With N-iodo-succinimide In N,N-dimethyl-formamide at 70℃; for 3h;81%
With N-iodo-succinimide In methanol at 50℃; for 1h;
With N-iodo-succinimide In methanol for 2h; Reflux; Large scale;53.26 kg
N,N-phenylbistrifluoromethane-sulfonimide
37595-74-7

N,N-phenylbistrifluoromethane-sulfonimide

methyl 6-hydroxynicotinate
66171-50-4

methyl 6-hydroxynicotinate

methyl 2-<(trifluoromethyl)sulfonyl>pyridine-5-carboxylate
163276-23-1

methyl 2-<(trifluoromethyl)sulfonyl>pyridine-5-carboxylate

Conditions
ConditionsYield
With triethylamine In dichloromethane for 48h; Ambient temperature;80%
With triethylamine In dichloromethane for 48h; Ambient temperature;68%
methyl 6-hydroxynicotinate
66171-50-4

methyl 6-hydroxynicotinate

2-Nitrobenzenesulfonyl chloride
1694-92-4

2-Nitrobenzenesulfonyl chloride

methyl 1-[(2-nitrophenyl)sulfonyl]-6-oxo-1,6-dihydropyridine-3-carboxylate
864812-33-9

methyl 1-[(2-nitrophenyl)sulfonyl]-6-oxo-1,6-dihydropyridine-3-carboxylate

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at -78 - 40℃; for 20.75h;80%
methyl 6-hydroxynicotinate
66171-50-4

methyl 6-hydroxynicotinate

[1-(2-Hydroxyethyl)-1H-pyrrol-2-yl](4-methylphenyl)methanone
620621-44-5

[1-(2-Hydroxyethyl)-1H-pyrrol-2-yl](4-methylphenyl)methanone

Methyl 6-{2-[2-(4-methylbenzoyl)-1H-pyrrol-1-yl]ethoxy}nicotinate
840503-18-6

Methyl 6-{2-[2-(4-methylbenzoyl)-1H-pyrrol-1-yl]ethoxy}nicotinate

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran; toluene at 0 - 20℃; for 110h;74%
methyl 6-hydroxynicotinate
66171-50-4

methyl 6-hydroxynicotinate

(4-bromomethyl-2,3-difluoro-phenyl)-methanol

(4-bromomethyl-2,3-difluoro-phenyl)-methanol

1-(2,3-difluoro-4-hydroxymethyl-benzyl)-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid methyl ester

1-(2,3-difluoro-4-hydroxymethyl-benzyl)-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid methyl ester

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃;70%
methyl 6-hydroxynicotinate
66171-50-4

methyl 6-hydroxynicotinate

methanesulfonic acid 2-[2-(4-chloro-phenyl)-2,4,5,6-tetrahydro-cyclopentapyrazol-3-yl]-2-cyclohexyl-ethyl ester
1335213-36-9

methanesulfonic acid 2-[2-(4-chloro-phenyl)-2,4,5,6-tetrahydro-cyclopentapyrazol-3-yl]-2-cyclohexyl-ethyl ester

6-{2-[2-(4-chloro-phenyl)-2,4,5,6-tetrahydro-cyclopentapyrazol-3-yl]-2-cyclohexyl-ethoxy}-nicotinic acid methyl ester
1335213-37-0

6-{2-[2-(4-chloro-phenyl)-2,4,5,6-tetrahydro-cyclopentapyrazol-3-yl]-2-cyclohexyl-ethoxy}-nicotinic acid methyl ester

Conditions
ConditionsYield
Stage #1: methyl 6-hydroxynicotinate With potassium carbonate In N,N-dimethyl-formamide at 0℃; for 0.25h;
Stage #2: methanesulfonic acid 2-[2-(4-chloro-phenyl)-2,4,5,6-tetrahydro-cyclopentapyrazol-3-yl]-2-cyclohexyl-ethyl ester In N,N-dimethyl-formamide at 0 - 100℃; for 12h; Sealed tube;
67%
Stage #1: methyl 6-hydroxynicotinate With potassium carbonate In N,N-dimethyl-formamide at 0℃; for 0.25h;
Stage #2: methanesulfonic acid 2-[2-(4-chloro-phenyl)-2,4,5,6-tetrahydro-cyclopentapyrazol-3-yl]-2-cyclohexyl-ethyl ester In N,N-dimethyl-formamide at 0 - 100℃; for 12h; Sealed tube;
67%
bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]
12354-84-6, 12354-85-7

bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]

methyl 6-hydroxynicotinate
66171-50-4

methyl 6-hydroxynicotinate

[(pentamethylcyclopentadienyl)Ir(5-methoxycarbonyl-2-pyridonate)Cl]

[(pentamethylcyclopentadienyl)Ir(5-methoxycarbonyl-2-pyridonate)Cl]

Conditions
ConditionsYield
Stage #1: methyl 6-hydroxynicotinate With sodium ethanolate In ethanol at 20℃; for 0.5h; Inert atmosphere; Schlenk technique;
Stage #2: bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] In dichloromethane at 5℃; Inert atmosphere; Schlenk technique;
56%
methyl 6-hydroxynicotinate
66171-50-4

methyl 6-hydroxynicotinate

N-(4-(chloromethyl)benzyl)acetamide
223512-41-2

N-(4-(chloromethyl)benzyl)acetamide

1-[4-(acetylamino-methyl)-benzyl]-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid methyl ester

1-[4-(acetylamino-methyl)-benzyl]-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid methyl ester

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 3h;53%
methyl 6-hydroxynicotinate
66171-50-4

methyl 6-hydroxynicotinate

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

A

methyl 1-[(4-methylphenyl)sulfonyl]-6-oxo-1,6-dihydropyridine-3-carboxylate
325489-16-5

methyl 1-[(4-methylphenyl)sulfonyl]-6-oxo-1,6-dihydropyridine-3-carboxylate

B

methyl 6-[(4-methylphenyl)sulfonyloxy]pyridine-3-carboxylate

methyl 6-[(4-methylphenyl)sulfonyloxy]pyridine-3-carboxylate

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane Reflux;A 31%
B 51%
2-iodo-propane
75-30-9

2-iodo-propane

methyl 6-hydroxynicotinate
66171-50-4

methyl 6-hydroxynicotinate

methyl 6-oxo-1-(propan-2-yl)-1,6-dihydropyridine-3-carboxylate

methyl 6-oxo-1-(propan-2-yl)-1,6-dihydropyridine-3-carboxylate

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 80℃; for 16h;51%
With potassium carbonate In acetonitrile at 80℃; for 16h;51%
methyl 6-hydroxynicotinate
66171-50-4

methyl 6-hydroxynicotinate

bromoacetic acid methyl ester
96-32-2

bromoacetic acid methyl ester

1-((methoxycarbonyl)methyl)-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid methyl ester
939751-69-6

1-((methoxycarbonyl)methyl)-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid methyl ester

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 40℃; for 18h;48%
methyl 6-hydroxynicotinate
66171-50-4

methyl 6-hydroxynicotinate

N-[2-(bromomethyl)-3-fluoro-allyl]carbamic acid tert-butyl ester

N-[2-(bromomethyl)-3-fluoro-allyl]carbamic acid tert-butyl ester

A

6-[(E)-2-[(tert-butoxycarbonylamino)methyl]-3-fluoro-propenyloxy]pyridine-3-carboxylic acid methyl ester

6-[(E)-2-[(tert-butoxycarbonylamino)methyl]-3-fluoro-propenyloxy]pyridine-3-carboxylic acid methyl ester

B

6-[(Z)-2-[(tert-butoxycarbonylamino)methyl]-3-fluoro-propenyloxy]pyridine-3-carboxylic acid methyl ester

6-[(Z)-2-[(tert-butoxycarbonylamino)methyl]-3-fluoro-propenyloxy]pyridine-3-carboxylic acid methyl ester

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 24h;A 48%
B 17%
methyl 6-hydroxynicotinate
66171-50-4

methyl 6-hydroxynicotinate

(3R,5S,6R,7R,8S,9S,10S,13R,14S,17R)-6-ethyl-17-((2R)-4-iodobutan-2-yl)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthrene-3,7-diyl diformate

(3R,5S,6R,7R,8S,9S,10S,13R,14S,17R)-6-ethyl-17-((2R)-4-iodobutan-2-yl)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthrene-3,7-diyl diformate

C34H49NO7

C34H49NO7

Conditions
ConditionsYield
With silver carbonate In chloroform at 60℃; for 72h;47.9%
methyl 6-hydroxynicotinate
66171-50-4

methyl 6-hydroxynicotinate

methyl 2-(bromomethyl)propenoate
4224-69-5

methyl 2-(bromomethyl)propenoate

1-(2-methoxycarbonyl-allyl)-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid methyl ester
1243279-10-8

1-(2-methoxycarbonyl-allyl)-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid methyl ester

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 40℃; for 18h;44%
methyl 6-hydroxynicotinate
66171-50-4

methyl 6-hydroxynicotinate

(3-phenyl-5-(trifluoromethyl)isoxazol-4-yl)methanol
1159600-63-1

(3-phenyl-5-(trifluoromethyl)isoxazol-4-yl)methanol

6-(3-phenyl-5-trifluoromethyl-isoxazol-4-ylmethoxy)-nicotinic acid methyl ester
1159600-61-9

6-(3-phenyl-5-trifluoromethyl-isoxazol-4-ylmethoxy)-nicotinic acid methyl ester

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20 - 50℃; for 2h;42%

66171-50-4Relevant articles and documents

A Diels-Alder Route to Pyridone and Piperidone Derivatives

Sainte, Francy,Serckx-Poncin, Beatrice,Hesbain-Frisque, Anne-Marie,Ghosez, Leon

, p. 1428 - 1430 (1982)

-

A new method using 1,3,5-triazine as an umpolung hydrogen cyanide equivalent toward the syntheses of isoquinolinone and 2-pyridone derivatives

Hayashida, Joji,Yoshida, Shinya

supporting information, p. 3876 - 3879 (2018/10/02)

An investigation of Hermecz and Hartenstein's cyclization methods was conducted. Overcoming the limited substrate scope allowed the expansion of the synthetic application of 1,3,5-triazine as an umpolung hydrogen cyanide equivalent. The reaction proceeded under mild conditions to provide various isoquinolinone and 2-pyridone derivatives with excellent yields.

Preparation method of 2-chloro-5-cyano nitrogen-containing six-membered heterocyclic compound

-

Paragraph 0069; 0070; 0071; 0072, (2019/01/08)

The invention provides a preparation method of a 2-chloro-5-cyano nitrogen-containing six-membered heterocyclic compound. The method comprises the following steps: using a 2-hydroxy-5-bromine nitrogen-containing six-membered heterocyclic compound as a raw material, under existence of a catalyst, in atmosphere of carbon monoxide gas, using methanol as a solvent, and performing a coupling reaction to obtain a methyl 2-hydroxyl nitrogen-containing six-membered heterocyclic ring-5-carboxylate, and sequentially performing an aminolysis reaction, a chlorination reaction with phosphorus oxychloride,and an oxidation reaction to obtain the 2-chloro-5-cyano nitrogen-containing six-membered heterocyclic compound. The preparation method has the advantages of short route and easily available raw material, a post-processing method is simple, no column chromatography is required after each reaction, the reaction product can be purified only by washing and extraction of a solvent, amplification is realized, industrial production is carried out, the method accords with environmental protection requirements, and has important value for actual production.

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