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87-41-2

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87-41-2 Usage

Description

White powder; sweet tonka, coumarin, powdery, coconut, phenolic, lactonic aroma.

Uses

Phthalide may be used in scaffolds for the design of high potency monoamine oxidase (MAO) inhibitors.

Definition

ChEBI: A gamma-lactone that is 1,3-dihydro-2-benzofuran in which the hydrogens at position 1 are replaced by an oxo group.

Aroma threshold values

Low strength odor, Tonka type.

Taste threshold values

Sweet coumarin, coconut, creamy, anisic, green vegetable, floral taste at 100 ppm in water.

Synthesis Reference(s)

Chemistry Letters, 23, p. 1149, 1994The Journal of Organic Chemistry, 68, p. 9423, 2003 DOI: 10.1021/jo0350763Tetrahedron Letters, 7, p. 6097, 1966

Flammability and Explosibility

Notclassified

Pharmacology

Systemic fungicide giving effective preventive control of the rice blast fungus in rice as foliar spray.

Purification Methods

Crystallise phthalide from water (75mL/g) and dry it in air on filter paper. [Beilstein 17/10 V 7.]

Toxicity evaluation

Mammalian toxicology. Oral: Acute oral LD50 for rats and mice >10000 mg/kg. Skin and eye: Acute percutaneous LD50 for rats and mice >10000 mg/kg. Not a shaved skin irritant, eye irritant (rabbits). Inhalation LC50 (4 h) for rats >4.1 mg/L air. NOEL: (2 yr) for rats 2000, mice 100 mg/kg diet.

Check Digit Verification of cas no

The CAS Registry Mumber 87-41-2 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 7 respectively; the second part has 2 digits, 4 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 87-41:
(4*8)+(3*7)+(2*4)+(1*1)=62
62 % 10 = 2
So 87-41-2 is a valid CAS Registry Number.
InChI:InChI=1/C8H6O2/c9-8-7-4-2-1-3-6(7)5-10-8/h1-4H,5H2

87-41-2 Well-known Company Product Price

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  • Alfa Aesar

  • (A15516)  Phthalide, 98+%   

  • 87-41-2

  • 100g

  • 274.0CNY

  • Detail
  • Alfa Aesar

  • (A15516)  Phthalide, 98+%   

  • 87-41-2

  • 500g

  • 1095.0CNY

  • Detail
  • Alfa Aesar

  • (A15516)  Phthalide, 98+%   

  • 87-41-2

  • 2500g

  • 4784.0CNY

  • Detail
  • Aldrich

  • (P39605)  Phthalide  98%

  • 87-41-2

  • P39605-100G

  • 335.79CNY

  • Detail
  • Aldrich

  • (P39605)  Phthalide  98%

  • 87-41-2

  • P39605-500G

  • 1,215.63CNY

  • Detail

87-41-2SDS

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 2-benzofuran-1(3H)-one

1.2 Other means of identification

Product number -
Other names Rabcide

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
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:87-41-2 SDS

87-41-2Synthetic route

phthalyl alcohol
612-14-6

phthalyl alcohol

2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

Conditions
ConditionsYield
With (CH3)5C5*Ir(-OCH2C(C6H5)2NH-) In acetone at 20℃; for 4h;100%
With sodium bromate; hydrogen bromide In acetic acid at 35℃; for 5h;99%
With periodic acid; pyridinium chlorochromate In acetonitrile at 0 - 20℃; for 2h;99%
o-phthalic dicarboxaldehyde
643-79-8

o-phthalic dicarboxaldehyde

2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

Conditions
ConditionsYield
With calcium oxide In benzene at 39.84℃; for 0.25h; Tishchenko reaction;100%
[La2(tBu2pz)6] In benzene-d6 at 21℃; Tishchenko reaction;100%
With [(ImDippN)Th{N(SiMe3)2}3] In benzene-d6 at 20℃; for 6h;100%
carbon monoxide
201230-82-2

carbon monoxide

2-iodobenzyl alcohol
5159-41-1

2-iodobenzyl alcohol

2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

Conditions
ConditionsYield
With potassium carbonate; bis-triphenylphosphine-palladium(II) chloride In N,N-dimethyl-formamide at 60℃; under 760 Torr; for 72h;100%
With N-ethyl-N,N-diisopropylamine; C50H42O2P2Pd2; triphenylphosphine In toluene at 60℃; for 1.66667h; Conversion of starting material;100%
With triethylamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; palladium dichloride In toluene at 80℃; under 760.051 Torr; for 4h;97%
o-xylene
95-47-6

o-xylene

A

2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

B

phthalic anhydride
85-44-9

phthalic anhydride

Conditions
ConditionsYield
With oxygen at 340 - 360℃; Product distribution / selectivity;A 0.01%
B 100%
With oxygen at 340 - 360℃;A 0.1%
B 100%
With oxygen at 340 - 360℃;A 0.03%
B 100%
Reaxys ID: 11463934

Reaxys ID: 11463934

A

2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

B

phthalic anhydride
85-44-9

phthalic anhydride

C

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

Conditions
ConditionsYield
With oxygen at 340 - 360℃; Product distribution / selectivity;A 0.01%
B 100%
C 0.02%
With oxygen at 340 - 360℃;A 0.03%
B 100%
C 0.05%
With oxygen at 340 - 360℃;A 0.01%
B 100%
C 0.01%
Reaxys ID: 11463934

Reaxys ID: 11463934

A

2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

B

phthalic anhydride
85-44-9

phthalic anhydride

Conditions
ConditionsYield
With oxygen at 340 - 360℃;A 0.01%
B 100%
With oxygen at 340 - 360℃;A 0.01%
B 100%
Reaxys ID: 11464679

Reaxys ID: 11464679

A

2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

B

phthalic anhydride
85-44-9

phthalic anhydride

C

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

Conditions
ConditionsYield
With oxygen at 354 - 357℃;A 0.2%
B 100%
C 0.15%
Phthaloyl dichloride
88-95-9

Phthaloyl dichloride

2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

Conditions
ConditionsYield
With triethylsilane; iron(III)-acetylacetonate at 60℃; for 0.666667h;99%
With triethylsilane; iron(III)-acetylacetonate at 60℃; for 0.666667h; other catalysts: Co(acac)2, Ni(acac)2; same reaction of iso- and terephthaloyl chloride;99%
With tricyclohexylborane at 300℃; for 2h;11.5%
1,3-dihydroisobenzofuran
496-14-0

1,3-dihydroisobenzofuran

2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

Conditions
ConditionsYield
With chromium(VI) oxide; periodic acid In acetonitrile at 20℃; for 0.25h;99%
With oxygen In dimethyl sulfoxide at 20℃; under 760.051 Torr; for 24h; Irradiation;99%
With tert.-butylhydroperoxide; 0.5C34H18N16(4-)*2H2O*2Cu(1+)*C3H7NO In water at 20℃; for 6h; Reagent/catalyst; Time; Sonication;97%
phthalic anhydride
85-44-9

phthalic anhydride

2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

Conditions
ConditionsYield
With Li(1+)*C12H28AlO3(1-) In tetrahydrofuran; hexane at -78℃; for 1h;98%
With lithium borohydride In tetrahydrofuran for 0.25h;91%
With 4-butanolide; cyclohexane; hydrogen at 180℃; under 30003 Torr; for 4h; Catalytic behavior; Reagent/catalyst; Time; Autoclave;89.6%
1,3-dihydroisobenzofuran
496-14-0

1,3-dihydroisobenzofuran

A

2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

B

1,3-dihydroisobenzofuran-1-ol
59868-79-0

1,3-dihydroisobenzofuran-1-ol

Conditions
ConditionsYield
With cobalt(III) acetylacetonate; oxygen In ethyl acetate at 70℃; for 24h;A 98%
B 1%
7,7a-dihydro-3H-3a,6-epoxyisobenzofuran-1(6H)-one

7,7a-dihydro-3H-3a,6-epoxyisobenzofuran-1(6H)-one

2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

Conditions
ConditionsYield
With methanesulfonic acid; acetic anhydride at 80℃; Temperature; Reagent/catalyst;98%
With sulfuric acid; acetic anhydride at 0 - 80℃; for 1h;
o-carboxybenzaldehyde
119-67-5

o-carboxybenzaldehyde

2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

Conditions
ConditionsYield
With (dipyridylamine)Cp*IrOSO3; hydrogen In water at 130℃; under 3750.38 Torr; for 32h;97%
With formic acid; C20H29ClIrN4(1+)*Cl(1-) In water at 80℃; for 2h; chemoselective reaction;91%
With sodium tetrahydroborate; nickel(II) phthalocyanine In PEG-400 at 20℃; for 0.333333h; chemoselective reaction;87%
With iodine; phosphorous acid In 1,2-dichloro-ethane at 60℃; for 13h; Inert atmosphere; Schlenk technique;86%
Multi-step reaction with 2 steps
1: fluorobenzene / 0.5 h / 46 °C / Microwave irradiation
2: potassium carbonate / fluorobenzene / 0.17 h / 155 °C
View Scheme
2-iodobenzyl alcohol
5159-41-1

2-iodobenzyl alcohol

terephthalaldehyde,
623-27-8

terephthalaldehyde,

2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

Conditions
ConditionsYield
Stage #1: terephthalaldehyde, With palladium 10% on activated carbon; sodium carbonate In isopropyl alcohol at 110℃; for 24h; Inert atmosphere;
Stage #2: 2-iodobenzyl alcohol With triphenylphosphine In 1-methyl-pyrrolidin-2-one; isopropyl alcohol at 100℃; for 24h; Catalytic behavior; Solvent; Temperature; Inert atmosphere;
97%
Stage #1: terephthalaldehyde, With palladium 10% on activated carbon; sodium carbonate In isopropyl alcohol at 120℃; for 24h; Inert atmosphere;
Stage #2: 2-iodobenzyl alcohol With triphenylphosphine In 1-methyl-pyrrolidin-2-one at 100℃; for 24h; Inert atmosphere;
85%
2-hydroxymethyl-benzoic acid hydrazide
51707-35-8

2-hydroxymethyl-benzoic acid hydrazide

2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

Conditions
ConditionsYield
With t-butyldimethylsiyl triflate; N,N-dimethyl-formamide at 20℃; for 20h;97%
2-(bromomethyl)benzoic acid
7115-89-1

2-(bromomethyl)benzoic acid

2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

Conditions
ConditionsYield
Stage #1: 2-(bromomethyl)benzoic acid With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetone for 0.166667h;
Stage #2: With methyl iodide In acetone at 20℃; for 4h;
96%
With cesium fluoride In acetonitrile for 10h; Heating;80%
With sodium hydroxide anschl. Ansaeuern;
In gas at 380℃; Mechanism; Thermodynamic data; Ea(excit.);
benzo[c]thiophene-1,3-dione
5698-59-9

benzo[c]thiophene-1,3-dione

A

2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

B

3-hydroxy-2-thiophthalide

3-hydroxy-2-thiophthalide

Conditions
ConditionsYield
With sodium tetrahydroborate In tetrahydrofuran at 0 - 20℃; for 1.5h;A n/a
B 96%
carbon monoxide
201230-82-2

carbon monoxide

o-bromobenzyl alcohol
18982-54-2

o-bromobenzyl alcohol

2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

Conditions
ConditionsYield
With tetrabutylammomium bromide; dicobalt octacarbonyl In sodium hydroxide; benzene at 65℃; for 2.5h; Irradiation;95%
With potassium carbonate; F-CH2Co(CO)4 In methanol at 25℃;84%
With di-μ-iodobis(tri-t-butylphosphino)dipalladium(l); triethylamine In toluene at 100℃; under 900.09 Torr; for 12h;82 %Chromat.
styrene oxide
96-09-3

styrene oxide

o-bromobenzyl alcohol
18982-54-2

o-bromobenzyl alcohol

2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

Conditions
ConditionsYield
With 5%-palladium/activated carbon; sodium fluoride In 1,4-dioxane at 150℃; for 24h;94%
styrene
292638-84-7

styrene

o-bromobenzyl alcohol
18982-54-2

o-bromobenzyl alcohol

2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

Conditions
ConditionsYield
With 5%-palladium/activated carbon; sodium fluoride; 3-chloro-benzenecarboperoxoic acid In 1,4-dioxane at 150℃; for 24h;94%
4,7-dihyrophthalide
21483-54-5

4,7-dihyrophthalide

2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

Conditions
ConditionsYield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In toluene for 14h; Ambient temperature;92%
ethanol
64-17-5

ethanol

o-bromobenzyl alcohol
18982-54-2

o-bromobenzyl alcohol

2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

Conditions
ConditionsYield
With dmap; palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In toluene at 90℃; for 0.5h; Microwave irradiation;92%
phthalyl alcohol
612-14-6

phthalyl alcohol

A

2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

B

butanedial
638-37-9

butanedial

Conditions
ConditionsYield
With 1-methyl-1H-imidazole; [2,2]bipyridinyl; tetrakis(acetonitrile)copper(I) trifluoromethanesulfonate; 9-azabicyclo<3.3.1>nonane-N-oxyl In acetonitrile at 22℃; for 2h;A 92%
B 8%
Diethyl phthalate
84-66-2

Diethyl phthalate

A

2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

B

phthalyl alcohol
612-14-6

phthalyl alcohol

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol; tert-butyl alcohol Heating;A 9%
B 91%
With sodium tetrahydroborate In methanol; tert-butyl alcohol Heating;A 8%
B 91%
With diisobutylaluminium hydride In dichloromethane; toluene at -30 - 20℃; for 1h; Inert atmosphere; regioselective reaction;A 68%
B 10%
With diisobutylaluminium hydride In dichloromethane; toluene at -30 - 20℃; for 1h; Temperature; Inert atmosphere; regioselective reaction;A 30%
B 60%
2-(hydroxymethyl)benzoic acid
612-20-4

2-(hydroxymethyl)benzoic acid

2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

Conditions
ConditionsYield
With oxygen In water at 80℃; for 12h; Reagent/catalyst; Sealed tube;90%
With copper(II) oxide; zinc In water at 250℃; for 2h;17%
With water
2-[(Diisopropoxy-methyl-silanyl)-methyl]-benzoic acid methyl ester
85719-69-3

2-[(Diisopropoxy-methyl-silanyl)-methyl]-benzoic acid methyl ester

2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

Conditions
ConditionsYield
With peracetic acid; potassium fluoride In N,N-dimethyl-formamide for 18h; Ambient temperature;90%
benzoic acid
65-85-0

benzoic acid

1,2-dibromomethane
74-95-3

1,2-dibromomethane

2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

Conditions
ConditionsYield
With dipotassium hydrogenphosphate; palladium diacetate at 140℃; for 36h;90%
With dipotassium hydrogenphosphate; palladium diacetate at 130℃; for 36h;87%
With palladium diacetate for 36h; Alkaline conditions; Heating;
(2-methoxyphenyl)methanol
612-16-8

(2-methoxyphenyl)methanol

2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

Conditions
ConditionsYield
With tungsten(VI) oxide monohydrate; dihydrogen peroxide In water; tert-butyl alcohol at 80℃; for 24h;90%
3-chloro-1(3H)-isobenzofuranone
6295-21-2

3-chloro-1(3H)-isobenzofuranone

2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

Conditions
ConditionsYield
With triethylamine; nickel In tetrahydrofuran89%
With hydrogen In Pt on charcoal; 5,5-dimethyl-1,3-cyclohexadiene
With sodium acetate; palladium In acetic acid
o-phthalic dicarboxaldehyde
643-79-8

o-phthalic dicarboxaldehyde

phenylboronic acid
98-80-6

phenylboronic acid

A

2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

B

3-phenylphthalide
5398-11-8

3-phenylphthalide

Conditions
ConditionsYield
With potassium carbonate; 1,2-bis-(diphenylphosphino)ethane; cobalt(II) iodide In tetrahydrofuran at 80℃; for 12h; Inert atmosphere;A 10%
B 89%
With 1,10-Phenanthroline; potassium carbonate; cobalt(II) chloride In acetonitrile at 80℃; for 12h; Inert atmosphere;A 65%
B 36%
2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

methylmagnesium bromide
75-16-1

methylmagnesium bromide

α,α-dimethyl-o-xylene α,α'-diol
55549-01-4

α,α-dimethyl-o-xylene α,α'-diol

Conditions
ConditionsYield
at -78 - 20℃;100%
In tetrahydrofuran; diethyl ether at 30℃; for 12.5h;88%
unter Wasserabgabe entsteht 1.1-Dimethyl-phthalan;
2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

methylamine
74-89-5

methylamine

2-methylisoindolin-1-one
5342-91-6

2-methylisoindolin-1-one

Conditions
ConditionsYield
In water at 220℃; under 114000 Torr; for 4h;100%
With ethanol at 220℃;
In 5,5-dimethyl-1,3-cyclohexadiene
2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

phthalyl alcohol
612-14-6

phthalyl alcohol

Conditions
ConditionsYield
With sodium aluminum tetrahydride In tetrahydrofuran at 0℃; for 0.25h;100%
With dimethyl zinc(II); sodium hydride In tetrahydrofuran at 0℃; for 6h;100%
With lithium aluminium tetrahydride In tetrahydrofuran at 25℃; under 760.051 Torr; for 16h; Inert atmosphere;99%
2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

phenylmethanethiol
100-53-8

phenylmethanethiol

2-<(Benzylthio)methyl>benzoic acid
1218-59-3

2-<(Benzylthio)methyl>benzoic acid

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide; mineral oil for 45h; Reflux;100%
With sodium hydride In N,N-dimethyl-formamide for 24h; Heating;99%
58%
With sodium ethanolate In ethanol
methanol
67-56-1

methanol

2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

o-(chloromethyl)benzoic acid methyl ester
34040-62-5

o-(chloromethyl)benzoic acid methyl ester

Conditions
ConditionsYield
Stage #1: 2-benzofuran-1(3H)-one With boron trifluoride diethyl etherate; N-benzyl-N,N,N-triethylammonium chloride In xylene at 100℃;
Stage #2: With thionyl chloride In xylene at 100 - 132℃; for 3h;
Stage #3: methanol at 50 - 60℃; for 2h;
100%
Stage #1: 2-benzofuran-1(3H)-one With chloro(triphenyl)phosphonium chloride at 180℃; for 2h;
Stage #2: methanol With pyridine for 1h;
With pyridine; dichlorotriphenylphosphorane at 180℃;
2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

lithium 3-oxo-1,3-dihydroisobenzofuran-1-carboxylate

lithium 3-oxo-1,3-dihydroisobenzofuran-1-carboxylate

Conditions
ConditionsYield
In tetrahydrofuran; hexane100%
2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

2,6-difluorobenzaldehyde
437-81-0

2,6-difluorobenzaldehyde

2-(2,6-difluorophenyl)-1,3-dioxoindane

2-(2,6-difluorophenyl)-1,3-dioxoindane

Conditions
ConditionsYield
With sodium methylate In methanol for 2h; Reflux;100%
2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

methylamine
74-89-5

methylamine

2-(hydroxymethyl)-N-methylbenzamide
39976-03-9

2-(hydroxymethyl)-N-methylbenzamide

Conditions
ConditionsYield
In methanol for 36h;99.5%
2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

p-methoxybenzyl chloride
824-94-2

p-methoxybenzyl chloride

4-methoxybenzyl 2-(hydroxymethyl)benzoate

4-methoxybenzyl 2-(hydroxymethyl)benzoate

Conditions
ConditionsYield
Stage #1: 2-benzofuran-1(3H)-one With sodium hydroxide In water at 20℃; for 3h;
Stage #2: p-methoxybenzyl chloride In N,N-dimethyl-formamide at 80℃; for 1h;
99%
Stage #1: 2-benzofuran-1(3H)-one With water; sodium hydroxide In tetrahydrofuran at 20℃; for 3h;
Stage #2: p-methoxybenzyl chloride In N,N-dimethyl-formamide at 80℃; for 1h;
2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

1,2-bis(((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)oxy)methyl)benzene

1,2-bis(((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)oxy)methyl)benzene

Conditions
ConditionsYield
With ToMMgMe at 24.84℃; for 1h;99%
With C12H36MgN2Si4 In neat (no solvent) at 20℃; for 0.25h; Catalytic behavior; Reagent/catalyst; Solvent; Inert atmosphere; Schlenk technique;99%
With C42H50Mg2N4 In neat (no solvent) at 25℃; for 1h; Glovebox; Schlenk technique; Inert atmosphere;99 %Spectr.
2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

tert-Butoxybis(dimethylamino)methane
5815-08-7

tert-Butoxybis(dimethylamino)methane

3-isobenzofuran-1(3H)-one
89968-08-1

3-isobenzofuran-1(3H)-one

Conditions
ConditionsYield
at 135℃; for 0.5h;98%
2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

tetra(n-butyl)ammonium hydroxide
2052-49-5

tetra(n-butyl)ammonium hydroxide

tetra-n-butylammonium 2-(hydroxymethyl)benzoate
93612-81-8

tetra-n-butylammonium 2-(hydroxymethyl)benzoate

Conditions
ConditionsYield
for 0.5h;98%
With water for 1.5h; Heating;39 g
In water for 1.5h; Heating;
2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

butyraldehyde
123-72-8

butyraldehyde

3-hydroxybutyl phthalide
168288-19-5

3-hydroxybutyl phthalide

Conditions
ConditionsYield
Stage #1: 2-benzofuran-1(3H)-one With lithium diisopropyl amide In tetrahydrofuran at -78℃;
Stage #2: butyraldehyde In tetrahydrofuran
98%
With lithium diisopropyl amide 1.) THF, -78 deg C, 10 min, 2.) THF, -78 deg C, 1-2 h; Yield given. Multistep reaction;
2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

N-butylamine
109-73-9

N-butylamine

N-butyl-2-hydroxymethylbenzamide
39976-06-2

N-butyl-2-hydroxymethylbenzamide

Conditions
ConditionsYield
In neat (no solvent) at 40℃; for 3h;98%
2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

α-carboxy-α'-hydroxy-o-xylene sodium salt

α-carboxy-α'-hydroxy-o-xylene sodium salt

Conditions
ConditionsYield
With sodium hydroxide In water for 2h; Reflux;98%
2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

3-Bromophthalide
6940-49-4

3-Bromophthalide

Conditions
ConditionsYield
With N-Bromosuccinimide In tetrachloromethane97%
With N-Bromosuccinimide In tetrachloromethane for 0.666667h; Bromination; Irradiation;94%
With N-Bromosuccinimide In tetrachloromethane for 0.666667h; Irradiation;94%
2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

1,3-dihydroisobenzofuran-1-ol
59868-79-0

1,3-dihydroisobenzofuran-1-ol

Conditions
ConditionsYield
With diisobutylaluminium hydride In hexane; dichloromethane at -78℃; for 1.5h;97%
With diisobutylaluminium hydride91%
With diisobutylaluminium hydride In dichloromethane at -78℃;70%

87-41-2Relevant articles and documents

Acid-tolerant intermetallic cobalt-nickel silicides as noble metal-like catalysts for selective hydrogenation of phthalic anhydride to phthalide

Zhang, Liangliang,Chen, Xiao,Chen, Yujing,Peng, Zhijian,Liang, Changhai

, p. 1108 - 1116 (2019)

Chemoselective hydrogenation of phthalic anhydride is regarded as the most promising route for producing downstream high-performance phthalide. A series of intermetallic cobalt-nickel silicide catalysts embedded in a carbon matrix (CoxNi2-xSi@C) with acid-tolerance prepared by microwave-assisted chemical vapor deposition have been investigated in this reaction system. Activity measurements show a remarkable positive synergistic effect, forming a volcano-shaped plot over the nominal Co metal fraction for CoxNi2-xSi@C catalysts with a peak at x = 1.5, which corresponds to a 4.5-fold enhancement of the yield of phthalide over Co2Si@C and a 2.0-fold enhancement over the Ni2Si@C monometallic silicide catalysts, which can be correlated with the interaction of cobalt-nickel and metal-silicon bonds. In addition, the cobalt-rich bimetallic silicide exhibits an equal activity to the reference noble metal catalysts (Au, Pd, and Pt) and a significantly higher activity than transition metal catalysts. Moreover, the bimetallic silicide as an intermetallic compound catalyst has demonstrated robust acid corrosion resistance compared to the corresponding metal catalysts.

Catalytic enantioselective intramolecular Tishchenko reaction ofmeso-dialdehyde: synthesis of (S)-cedarmycins

Ismiyarto,Kishi, Nobuki,Adachi, Yuki,Jiang, Rui,Doi, Takahiro,Zhou, Da-Yang,Asano, Kaori,Obora, Yasushi,Suzuki, Takayoshi,Sasai, Hiroaki,Suzuki, Takeyuki

, p. 11606 - 11609 (2021)

The first successful example of a catalytic enantioselective intramolecular Tishchenko reaction of ameso-dialdehyde in the presence of a chiral iridium complex is described. Chiral lactones were obtained in good yields with up to 91% ee. The obtained enantioenriched lactones were utilized for the first synthesis of (S)-cedarmycins A and B.

-

Harrison et al.

, p. 5793 (1970)

-

-

Hamaguchi,Ibata

, p. 287 (1976)

-

Strong base catalysis of sulfated mesoporous alumina for the Tishchenko reaction in supercritical carbon dioxide

Seki, Tsunetake,Onaka, Makoto

, p. 262 - 263 (2005)

Heterogeneous strong base catalysis for the Tishchenko reaction in acidic scCO2 solvent has been realized with mesoporous alumina modified with SO42-, while a conventional solid base like CaO showed almost no catalytic performance in scCO2. Copyright

An efficient carbonylation of aryl halides catalysed by palladium complexes with phosphite ligands in supercritical carbon dioxide

Kayaki, Yoshihito,Noguchi, Yushi,Iwasa, Seiji,Ikariya, Takao,Noyori, Ryoji

, p. 1235 - 1236 (1999)

The carbonylation of aryl halides catalysed by CO2 soluble Pd complexes with trialkyl or triaryl phosphite ligands proceeds rapidly in scCO2, in which the rate of the reaction is higher than those attained in solution phase reactions.

(Diacetoxyiodo)benzene-mediated oxygenation of benzylic C(sp3)-H bonds with N-hydroxyamides at room temperature

Qian, Peng-Cheng,Liu, Yu,Song, Ren-Jie,Hu, Ming,Yang, Xu-Heng,Xiang, Jian-Nan,Li, Jin-Heng

, p. 1680 - 1684 (2015)

A new, metal-free method for the formation of C(sp3)-O bonds was established by PhI(OAc)2-mediated oxygenation of benzylic C(sp3)-H bonds with N-hydroxyamides at room temperature, in which the C(sp3)-H oxidation is activated by a polyflurophenylamide group.

Sodium organoaluminate containing bidentate pyrrolyl ligand: Synthesis, structure, and catalytic activity for the Tishchenko reaction

Liu, Yu,Guo, Zhiqiang,Wang, Yakong

, (2021/05/26)

An novel sodium organoaluminate containing bidentate pyrrolyl ligand [C4H3NH(2-CH2NHtBu)] was efficiently synthesized and characterized by X-ray crystallography. The molecular structure shows it is a monodimensional infinite chain structures with linear arrangements. Its basic repeat unit comprises the Al atom bonded to two deprotonated pyrrole rings and Na atom coordinated to of nitrogen atoms of –NtBu fragment, which undergoes further to coordinates a pyrrolyl ring of an adjacent molecule in a ?2-fasion. Furthermore, this sodium organoaluminate exhibited high catalytic activities for Tishchenko reaction.

Covalent Organic Frameworks toward Diverse Photocatalytic Aerobic Oxidations

Liu, Shuyang,Tian, Miao,Bu, Xiubin,Tian, Hua,Yang, Xiaobo

supporting information, p. 7738 - 7744 (2021/05/07)

Photoactive two-dimensional covalent organic frameworks (2D-COFs) have become promising heterogenous photocatalysts in visible-light-driven organic transformations. Herein, a visible-light-driven selective aerobic oxidation of various small organic molecules by using 2D-COFs as the photocatalyst was developed. In this protocol, due to the remarkable photocatalytic capability of hydrazone-based 2D-COF-1 on molecular oxygen activation, a wide range of amides, quinolones, heterocyclic compounds, and sulfoxides were obtained with high efficiency and excellent functional group tolerance under very mild reaction conditions. Furthermore, benefiting from the inherent advantage of heterogenous photocatalysis, prominent sustainability and easy photocatalyst recyclability, a drug molecule (modafinil) and an oxidized mustard gas simulant (2-chloroethyl ethyl sulfoxide) were selectively and easily obtained in scale-up reactions. Mechanistic investigations were conducted using radical quenching experiments and in situ ESR spectroscopy, all corroborating the proposed role of 2D-COF-1 in photocatalytic cycle.

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