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108-24-7

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108-24-7 Usage

Safety Profile

Moderately toxic by inhalation,ingestion, and skin contact. A skin and severe eye irritant. A flammable liquid. A fire and explosion hazard whenexposed to heat or flame. Potentially explosive reactionswith barium peroxide, boric acid, chromium trioxide

Check Digit Verification of cas no

The CAS Registry Mumber 108-24-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 8 respectively; the second part has 2 digits, 2 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 108-24:
(5*1)+(4*0)+(3*8)+(2*2)+(1*4)=37
37 % 10 = 7
So 108-24-7 is a valid CAS Registry Number.
InChI:InChI=1/C4H6O3/c1-3(5)7-4(2)6/h1-2H3

108-24-7SDS

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 Acetic anhydride

1.2 Other means of identification

Product number -
Other names Acetic acid, anhydride

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Intermediates
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:108-24-7 SDS

108-24-7Synthetic route

silver(I) acetate
563-63-3

silver(I) acetate

A

acetic anhydride
108-24-7

acetic anhydride

B

silver(l) oxide
20667-12-3

silver(l) oxide

Conditions
ConditionsYield
In neat (no solvent) byproducts: Ag, CO2; 300-400°C, quartz-tube, Ar-atmosphere (1atm.), exclusion of H2O;;A 93%
B 96%
In neat (no solvent) calculation of change of free enthalpy during thermic decompn.;;
α-acetoxy-α-phenylbenzeneacetic acid
3808-00-2

α-acetoxy-α-phenylbenzeneacetic acid

A

tetraphenylethane-1,2-diol
464-72-2

tetraphenylethane-1,2-diol

B

acetic anhydride
108-24-7

acetic anhydride

Conditions
ConditionsYield
With triethylamine In acetonitrile Ambient temperature; electrolysis;A 93%
B n/a
With triethylamine In acetonitrile Product distribution; Ambient temperature; electrolysis;A 93%
B n/a
acetic acid
64-19-7

acetic acid

acetic anhydride
108-24-7

acetic anhydride

Conditions
ConditionsYield
With PEG-1000; sulfated zirconia at 40℃; for 2h; neat (no solvent);90%
With thionyl chloride In dichloromethane at 22 - 25℃; for 0.0833333h;88.8%
With diammonium phosphate at 725℃; under 195.02 Torr; Reagent/catalyst; Pyrolysis;48.8%
(Acetoxy)diphenylphosphane
65988-98-9

(Acetoxy)diphenylphosphane

A

acetic anhydride
108-24-7

acetic anhydride

B

complex of tetraphenyldiphosphine with tin tetrabromide

complex of tetraphenyldiphosphine with tin tetrabromide

C

complex of bis(diphenyldiphosphinic) anhydride with tin tetrabromide

complex of bis(diphenyldiphosphinic) anhydride with tin tetrabromide

Conditions
ConditionsYield
With stannic bromide In dichloromethane for 72h; Product distribution; Ambient temperature;A n/a
B n/a
C 90%
6-(4-aminophenyl)-1,3-dihydro-5-methyl-2H-imidazo[4,5-b]pyridin-2-one hydrochloride

6-(4-aminophenyl)-1,3-dihydro-5-methyl-2H-imidazo[4,5-b]pyridin-2-one hydrochloride

A

6-[4-(Acetylamino)phenyl]-1,3-dihydro-5-methyl-2H-imidazo[4,5-b]pyridin-2-one

6-[4-(Acetylamino)phenyl]-1,3-dihydro-5-methyl-2H-imidazo[4,5-b]pyridin-2-one

B

acetic anhydride
108-24-7

acetic anhydride

Conditions
ConditionsYield
A n/a
B 90%
A n/a
B 90%
diphenyltellurium di(acetate)
39652-00-1

diphenyltellurium di(acetate)

A

diphenyltellurium dichloride
1206-36-6

diphenyltellurium dichloride

B

acetic anhydride
108-24-7

acetic anhydride

Conditions
ConditionsYield
With acetyl chloride In chloroform for 5h; Heating;A 89%
B 81%
acetic acid
64-19-7

acetic acid

N,N,N',N'-tetraethyl-P-(trichloromethyl)phosphonoimidic diamide
77339-54-9

N,N,N',N'-tetraethyl-P-(trichloromethyl)phosphonoimidic diamide

A

chloroform
67-66-3

chloroform

B

N,N,N',N'-tetraethylphosphoric triamide
38590-11-3

N,N,N',N'-tetraethylphosphoric triamide

C

acetic anhydride
108-24-7

acetic anhydride

Conditions
ConditionsYield
In diethyl ether for 3h; Ambient temperature;A 89%
B 51%
C n/a
O-acetyl S,S-diethyl phosphorodithioite
84103-76-4

O-acetyl S,S-diethyl phosphorodithioite

A

diethyl phosphorochloridodithioite
1486-42-6

diethyl phosphorochloridodithioite

B

acetic anhydride
108-24-7

acetic anhydride

Conditions
ConditionsYield
With acetyl chloride for 0.5h; Ambient temperature;A 72%
B 89%
O-acetyl S,S-diethyl phosphorodithioite
84103-76-4

O-acetyl S,S-diethyl phosphorodithioite

acetyl chloride
75-36-5

acetyl chloride

A

diethyl phosphorochloridodithioite
1486-42-6

diethyl phosphorochloridodithioite

B

acetic anhydride
108-24-7

acetic anhydride

Conditions
ConditionsYield
at 20℃; for 0.5h;A 72%
B 89%
(Acetoxy)diphenylphosphane
65988-98-9

(Acetoxy)diphenylphosphane

A

acetic anhydride
108-24-7

acetic anhydride

B

complex of tetraphenyldiphosphine with tin tetrachloride

complex of tetraphenyldiphosphine with tin tetrachloride

C

complex of bis(diphenyldiphosphinic) anhydride with tin tetrachloride

complex of bis(diphenyldiphosphinic) anhydride with tin tetrachloride

Conditions
ConditionsYield
With tin(IV) chloride In dichloromethane for 72h; Product distribution; Ambient temperature;A n/a
B n/a
C 88%
N-{5-[2-(4-benzo[d]isothiazol-3-yl-piperazin-1-yl)-ethyl]-1,1,3,3-tetramethyl-indan-2-yl}-N-methylacetamide

N-{5-[2-(4-benzo[d]isothiazol-3-yl-piperazin-1-yl)-ethyl]-1,1,3,3-tetramethyl-indan-2-yl}-N-methylacetamide

methanesulfonic acid
75-75-2

methanesulfonic acid

acetic anhydride
108-24-7

acetic anhydride

Conditions
ConditionsYield
In diethyl ether; ethyl acetate at 20℃; for 0.25h;87%
O-acetyl-α-hydroxyisobutyric acid
15805-98-8

O-acetyl-α-hydroxyisobutyric acid

A

diethylacetamide
685-91-6

diethylacetamide

B

2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

C

Essigsaeure-2-hydroxy-1,1,2-trimethylpropylester
20127-81-5

Essigsaeure-2-hydroxy-1,1,2-trimethylpropylester

D

acetic anhydride
108-24-7

acetic anhydride

Conditions
ConditionsYield
With triethylamine In acetonitrile Ambient temperature; electrolysis; Further byproducts given;A 47%
B 86.8%
C 4.7%
D n/a
O-acetyl-α-hydroxyisobutyric acid
15805-98-8

O-acetyl-α-hydroxyisobutyric acid

triethylamine
121-44-8

triethylamine

A

diethylacetamide
685-91-6

diethylacetamide

B

2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

C

Essigsaeure-2-hydroxy-1,1,2-trimethylpropylester
20127-81-5

Essigsaeure-2-hydroxy-1,1,2-trimethylpropylester

D

acetic anhydride
108-24-7

acetic anhydride

Conditions
ConditionsYield
In acetonitrile Ambient temperature; electrolysis; Further byproducts given;A 47%
B 86.8%
C 4.7%
D n/a
sodium acetate
127-09-3

sodium acetate

A

sodium nitrate
7631-99-4

sodium nitrate

B

acetic anhydride
108-24-7

acetic anhydride

Conditions
ConditionsYield
With dinitrogen tetraoxide In neat (no solvent) byproducts: N2O3; addn. of N2O4 to dry Na acetate;;A n/a
B 85%
4-isopropylbiphenyl
7116-95-2

4-isopropylbiphenyl

A

4-Phenylphenol
92-69-3

4-Phenylphenol

B

acetic anhydride
108-24-7

acetic anhydride

Conditions
ConditionsYield
Stage #1: 4-isopropylbiphenyl With oxygen at 100℃; under 760.051 Torr; for 7h;
Stage #2: With sulfuric acid In acetone at 56℃; for 0.0833333h; Further stages.;
A 84%
B n/a
Acetyl bromide
506-96-7

Acetyl bromide

O-acetyl S,S-dipropyl phosphorodithioite
84103-77-5

O-acetyl S,S-dipropyl phosphorodithioite

A

acetic anhydride
108-24-7

acetic anhydride

B

dipropyl phosphorobromidodithioite

dipropyl phosphorobromidodithioite

Conditions
ConditionsYield
A 82%
B 69%
at 25℃; Product distribution; various time, with or without acetic acid or pyridine;
O-acetyl S,S-dipropyl phosphorodithioite
84103-77-5

O-acetyl S,S-dipropyl phosphorodithioite

A

acetic anhydride
108-24-7

acetic anhydride

B

dipropyl phosphorobromidodithioite

dipropyl phosphorobromidodithioite

Conditions
ConditionsYield
With Acetyl bromide for 1h; Ambient temperature;A 82%
B 69%
acetaldehyde
75-07-0

acetaldehyde

acetic anhydride
108-24-7

acetic anhydride

Conditions
ConditionsYield
With air; supported Pd/ZrO2 catalyst at 120℃; under 760.051 Torr;80%
With oxygen bei kurzer Verweilzeit unter Druck, vorteilhaft in Gegenwart von Metallsalzen, und sofortige Abtrennung von gleichzeitig entstandenem Wasser nach verschiedenen Verfahren erhalten;
With ozone bei kurzer Verweilzeit unter Druck, vorteilhaft in Gegenwart von Metallsalzen, und sofortige Abtrennung von gleichzeitig entstandenen Wasser nach verschiedenen Verfahren erhalten;
With oxygen bei kurzer Verweilzeit unter Druck, vorteilhaft in Gegenwart von Metallsalzen, und sofortige Abtrennung von gleichzeitig entstandenem Wasser nach verschiedenen Verfahren erhalten;
With ozone bei kurzer Verweilzeit unter Druck, vorteilhaft in Gegenwart von Metallsalzen, und sofortige Abtrennung von gleichzeitig entstandenen Wasser nach verschiedenen Verfahren erhalten;
diphenyl sulfide
139-66-2

diphenyl sulfide

3-diazo-2-butanone
14088-58-5

3-diazo-2-butanone

A

1,1'-sulfinylbisbenzene
945-51-7

1,1'-sulfinylbisbenzene

B

acetic anhydride
108-24-7

acetic anhydride

C

dimethylglyoxal
431-03-8

dimethylglyoxal

Conditions
ConditionsYield
With oxygen at -78 - 25℃; Product distribution; Mechanism; TPP as sensitizer;A 19%
B 5%
C 76%
formaldehyd
50-00-0

formaldehyd

dimethylacetylene
503-17-3

dimethylacetylene

A

diacetoxymethane
628-51-3

diacetoxymethane

B

acetic anhydride
108-24-7

acetic anhydride

C

acetic acid
64-19-7

acetic acid

D

dimethylglyoxal
431-03-8

dimethylglyoxal

Conditions
ConditionsYield
With ozone In dichloromethane at -100℃;A 7%
B 71%
C 17%
D 5%
acetoxyacetic acid
13831-30-6

acetoxyacetic acid

acetonitrile
75-05-8

acetonitrile

A

formaldehyd
50-00-0

formaldehyd

B

acetic anhydride
108-24-7

acetic anhydride

C

acetic acid
64-19-7

acetic acid

D

Essigsaeure-(diacetylamino)methylester
84785-16-0

Essigsaeure-(diacetylamino)methylester

E

Acetoxyessigsaeure-acetoxymethylester
84785-15-9

Acetoxyessigsaeure-acetoxymethylester

F

Essigsaeure-methylester
84785-17-1

Essigsaeure-methylester

Conditions
ConditionsYield
With triethylamine Mechanism; Product distribution; Ambient temperature; electrolysis;A 70%
B n/a
C n/a
D 4.8%
E 4.2%
F 5.5%
acetic acid methyl ester
79-20-9

acetic acid methyl ester

carbon monoxide
201230-82-2

carbon monoxide

A

1,1-diacetoxy-1-ethyl methane
33931-80-5

1,1-diacetoxy-1-ethyl methane

B

acetic anhydride
108-24-7

acetic anhydride

Conditions
ConditionsYield
With tributylphosphine; hydrogen; methyl iodide; acetylacetonatodicarbonylrhodium(l); palladium diacetate In acetic acid at 160℃; under 147102 Torr; for 4h;A 68.1%
B 5.3%
With tributylphosphine; hydrogen; methyl iodide; acetylacetonatodicarbonylrhodium(l); palladium diacetate In acetic acid at 160℃; under 152000 Torr; for 4h; Product distribution; The effect of mixed transition metal catalysts and the effect of various bases was investigated.;
silver(I) acetate
563-63-3

silver(I) acetate

1,3-dicyclohexylthiourea
1212-29-9

1,3-dicyclohexylthiourea

A

silver sulfide

silver sulfide

B

acetic anhydride
108-24-7

acetic anhydride

Conditions
ConditionsYield
In acetone byproducts: (C6H11NH)2CO; at room temp.;;A n/a
B 68%
ethyl acetate
141-78-6

ethyl acetate

A

acetic anhydride
108-24-7

acetic anhydride

B

acetic acid
64-19-7

acetic acid

Conditions
ConditionsYield
With chlorine at 51.84℃; under 730 Torr; Irradiation; chamber system;A 20%
B 66%
With chlorine at -24.16℃; under 730 Torr; Irradiation; chamber system;A 61%
B 26%
acetic acid
64-19-7

acetic acid

1-ethoxyacetylene
927-80-0

1-ethoxyacetylene

A

1-ethoxyvinyl acetate
5177-66-2

1-ethoxyvinyl acetate

B

acetic anhydride
108-24-7

acetic anhydride

Conditions
ConditionsYield
[ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 In tetrahydrofuran at 40℃; for 15h;A 65%
B n/a
piperidine
110-89-4

piperidine

acetic anhydride
108-24-7

acetic anhydride

1-piperidin-1-yl-ethanone
618-42-8

1-piperidin-1-yl-ethanone

Conditions
ConditionsYield
With pyridine; aluminum oxide at 95 - 97℃; for 2h; microwave irradiation;100%
In dichloromethane at 0 - 20℃; for 15h;100%
With tris(pentafluorophenyl)borate In neat (no solvent) at 20℃; for 0.0166667h; Green chemistry;97%
2-aminopyridine
504-29-0

2-aminopyridine

acetic anhydride
108-24-7

acetic anhydride

N-(2-pyridyl)acetamide
5231-96-9

N-(2-pyridyl)acetamide

Conditions
ConditionsYield
With pyridine In DMF (N,N-dimethyl-formamide) at 0 - 20℃;100%
With pyridine at 0 - 20℃;100%
With supported L-pyrrolidine-2-carboxylic acid-4-hydrogen sulfate on Silica Gel at 20℃; for 0.8h; Green chemistry;91%
2-Amino-6-methylpyridine
1824-81-3

2-Amino-6-methylpyridine

acetic anhydride
108-24-7

acetic anhydride

2-acetylamino-6-methylpyridine
5327-33-3

2-acetylamino-6-methylpyridine

Conditions
ConditionsYield
at 60 - 70℃; for 1.5h;100%
In tetrahydrofuran for 10h; Heating / reflux; Acidic aqueous solution;99%
at 90℃; for 1.5h;98%
5-Hydroxy-2-methylpyridine
1121-78-4

5-Hydroxy-2-methylpyridine

acetic anhydride
108-24-7

acetic anhydride

2-methyl-5-acetoxypyridine
4842-89-1

2-methyl-5-acetoxypyridine

Conditions
ConditionsYield
at 120℃; for 0.5h;100%
2-(N-methylamino)pyridine
4597-87-9

2-(N-methylamino)pyridine

acetic anhydride
108-24-7

acetic anhydride

2-[(N-acetyl-N-methyl)amino]pyridine
61996-35-8

2-[(N-acetyl-N-methyl)amino]pyridine

Conditions
ConditionsYield
at 70℃; for 4h;100%
With acetic acid
benzoimidazole
51-17-2

benzoimidazole

acetic anhydride
108-24-7

acetic anhydride

1-acetylbenzimidazole
18773-95-0

1-acetylbenzimidazole

Conditions
ConditionsYield
With acetic acid at 140℃; for 0.5h;100%
With N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate In acetonitrile at 20℃; for 0.25h; Acetylation;63%
3,4-bis(hydroxymethyl)furan
14496-24-3

3,4-bis(hydroxymethyl)furan

acetic anhydride
108-24-7

acetic anhydride

3,4-furan dimethanol diacetate
30614-73-4

3,4-furan dimethanol diacetate

Conditions
ConditionsYield
With pyridine100%
With sodium acetate
With pyridine
1-hydroxy-pyrrolidine-2,5-dione
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

acetic anhydride
108-24-7

acetic anhydride

N-acetoxysuccinimide
14464-29-0

N-acetoxysuccinimide

Conditions
ConditionsYield
for 15h;100%
With triethylamine for 0.5h;90%
With hydrogenchloride for 0.25h; Heating;79.9%
7-Indolol
2380-84-9

7-Indolol

acetic anhydride
108-24-7

acetic anhydride

1H-indol-7-yl acetate
5526-13-6

1H-indol-7-yl acetate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 16h; Inert atmosphere;100%
With pyridine
With dmap; potassium carbonate at 100℃; for 6h; Yield given;
1,3-benzothiazol-6-amine
533-30-2

1,3-benzothiazol-6-amine

acetic anhydride
108-24-7

acetic anhydride

N-acetyl-6-aminobenzothiazole
58249-63-1

N-acetyl-6-aminobenzothiazole

Conditions
ConditionsYield
With pyridine at 20℃;100%
With silica-supported boric acid In neat (no solvent) at 50℃; for 1h;96%
2-methyl-8-quinolinol
826-81-3

2-methyl-8-quinolinol

acetic anhydride
108-24-7

acetic anhydride

2‐methyl‐8‐acetoxyquinoline
27037-61-2

2‐methyl‐8‐acetoxyquinoline

Conditions
ConditionsYield
for 15h; Acetylation; Heating;100%
Reflux;99%
at 138℃; for 5h;95%
3-bromo-9H-carbazole
1592-95-6

3-bromo-9H-carbazole

acetic anhydride
108-24-7

acetic anhydride

1-(3-bromo-9H-carbazol-9-yl)ethan-1-one
177775-86-9

1-(3-bromo-9H-carbazol-9-yl)ethan-1-one

Conditions
ConditionsYield
With sulfuric acid Reflux;100%
With triethylamine In dichloromethane at 20℃; for 22h;100%
With boron trifluoride diethyl etherate Reflux;98%
7-hydroxy-4-methyl-chromen-2-one
90-33-5, 79566-13-5

7-hydroxy-4-methyl-chromen-2-one

acetic anhydride
108-24-7

acetic anhydride

4-methylumbelliferyl acetate
2747-05-9

4-methylumbelliferyl acetate

Conditions
ConditionsYield
With pyridine; dmap100%
With sodium hydroxide for 0.0125h; microwave irradiation;99%
With SiO2-supported Co(II) Salen complex catalyst at 50℃; for 0.75h;99%
4-hydroxydibenzofuran
19261-06-4

4-hydroxydibenzofuran

acetic anhydride
108-24-7

acetic anhydride

4-acetoxydibenzofuran
101762-27-0

4-acetoxydibenzofuran

Conditions
ConditionsYield
With sulfuric acid for 4h;100%
With sulfuric acid
5-chloro-7-iodoquinolin-8-ol
130-26-7

5-chloro-7-iodoquinolin-8-ol

acetic anhydride
108-24-7

acetic anhydride

5-chloro-7-iodoquinolin-8-yl ethanoate
27037-46-3

5-chloro-7-iodoquinolin-8-yl ethanoate

Conditions
ConditionsYield
With pyridine at 60℃; for 0.0833333h;100%
at 150℃; for 5h;94%
With pyridine
methyl 3,4-O-isopropylideneshikimate
88165-26-8

methyl 3,4-O-isopropylideneshikimate

acetic anhydride
108-24-7

acetic anhydride

(3aR,7R,7aS)-methyl 7-acetoxy-2,2-dimethyl-3a,6,7,7atetrahydrobenzo[d][1,3]dioxole-5-carboxylate
143308-74-1

(3aR,7R,7aS)-methyl 7-acetoxy-2,2-dimethyl-3a,6,7,7atetrahydrobenzo[d][1,3]dioxole-5-carboxylate

Conditions
ConditionsYield
With dmap In dichloromethane for 2h; Ambient temperature;100%
With pyridine at 20℃; for 1h;100%
With pyridine
phenylmethyl 1-piperazinecarboxylate
31166-44-6

phenylmethyl 1-piperazinecarboxylate

acetic anhydride
108-24-7

acetic anhydride

4-acetyl-1-benzyloxycarbonylpiperazine

4-acetyl-1-benzyloxycarbonylpiperazine

Conditions
ConditionsYield
With pyridine at 20℃; for 18h;100%
With benzene
With pyridine at 20℃; for 18h;
4',5,7-trihydroxy-8-methoxyisoflavone
13111-57-4

4',5,7-trihydroxy-8-methoxyisoflavone

acetic anhydride
108-24-7

acetic anhydride

5,7-diacetoxy-3-(4-acetoxy-phenyl)-8-methoxy-chromen-4-one
27181-88-0

5,7-diacetoxy-3-(4-acetoxy-phenyl)-8-methoxy-chromen-4-one

Conditions
ConditionsYield
With pyridine100%
With pyridine
quercetol
117-39-5

quercetol

acetic anhydride
108-24-7

acetic anhydride

3,5,7-triacetoxy-2-(3,4-diacetoxy-phenyl)-chromen-4-one
1064-06-8

3,5,7-triacetoxy-2-(3,4-diacetoxy-phenyl)-chromen-4-one

Conditions
ConditionsYield
With pyridine at 130 - 140℃;100%
With pyridine at 140 - 145℃; for 4h;97.5%
With pyridine at 70℃; for 6h;95%
2',3'-O-isopropylideneuridine
362-43-6

2',3'-O-isopropylideneuridine

acetic anhydride
108-24-7

acetic anhydride

1-(5-O-Acetyl-2,3-O-isopropylidene-β-D-ribofuranosyl)uracil
15922-23-3

1-(5-O-Acetyl-2,3-O-isopropylidene-β-D-ribofuranosyl)uracil

Conditions
ConditionsYield
With triethylamine In dichloromethane for 0.0833333h; Ambient temperature;100%
With iron(III) sulfate at 20℃; for 3h;99%
molecular sieve; potassium chloride at 100℃; for 1.5h;96%
In pyridine61%
With pyridine
3,4-methylenedioxyphenylethylamine
1484-85-1

3,4-methylenedioxyphenylethylamine

acetic anhydride
108-24-7

acetic anhydride

N-[2-(3,4-methylenedioxyphenyl)ethyl]acetamide
58026-25-8

N-[2-(3,4-methylenedioxyphenyl)ethyl]acetamide

Conditions
ConditionsYield
In toluene at 20℃;100%
orcinol
504-15-4

orcinol

acetic anhydride
108-24-7

acetic anhydride

5-methylbenzene-1,3-diyl diacetate
20982-28-9

5-methylbenzene-1,3-diyl diacetate

Conditions
ConditionsYield
dmap at 100℃; for 2.5h;100%
With tin(IV) tetraphenylporphyrin perchlorate at 20℃; for 0.0833333h;99%
With triethylamine In dichloromethane at 0 - 20℃; for 60h;94%
o-Coumaric acid
614-60-8

o-Coumaric acid

acetic anhydride
108-24-7

acetic anhydride

(E)-3-<2-(acetyloxy)phenyl>-2-propenoic acid
16189-10-9

(E)-3-<2-(acetyloxy)phenyl>-2-propenoic acid

Conditions
ConditionsYield
With dmap; triethylamine In tetrahydrofuran for 2h; Ambient temperature;100%
With sulfuric acid at 0℃;65%
With triethylamine In tetrahydrofuran at 0 - 30℃; for 1h; Inert atmosphere;38%
formic acid
64-18-6

formic acid

acetic anhydride
108-24-7

acetic anhydride

Acetic formic anhydride
2258-42-6

Acetic formic anhydride

Conditions
ConditionsYield
at 60℃; for 1h; Inert atmosphere;100%
at 0 - 60℃; for 3.5h;78%
at 50℃; Fraktionierung im Vakuum;
LACTIC ACID
849585-22-4

LACTIC ACID

acetic anhydride
108-24-7

acetic anhydride

2-acetoxypropionic acid
535-17-1

2-acetoxypropionic acid

Conditions
ConditionsYield
With sulfuric acid In water at 0 - 100℃; for 0.5h; Temperature; Reagent/catalyst; Solvent;100%
With hydrogenchloride; acetic acid
Chrysophanol
481-74-3

Chrysophanol

acetic anhydride
108-24-7

acetic anhydride

1,8-diacetoxy-3-methyl-anthraquinone
18713-45-6

1,8-diacetoxy-3-methyl-anthraquinone

Conditions
ConditionsYield
With sulfuric acid for 0.5h; Ambient temperature;100%
With sulfuric acid
With sodium acetate
alpha-D-mannopyranoside
7296-15-3

alpha-D-mannopyranoside

acetic anhydride
108-24-7

acetic anhydride

per-O-acetyl-α-D-mannopyranose
4163-65-9

per-O-acetyl-α-D-mannopyranose

Conditions
ConditionsYield
With pyridine; dmap100%
With sodium acetate Reflux;99%
With indium(III) triflate at 0℃; for 1h; Product distribution; Further Variations:; Reagents; Temperatures; reaction time; reaction conditions (microwave irradiation);96%
4-nitro-phenol
100-02-7

4-nitro-phenol

acetic anhydride
108-24-7

acetic anhydride

4-nitrophenol acetate
830-03-5

4-nitrophenol acetate

Conditions
ConditionsYield
K5 In acetonitrile at 20℃; for 0.333333h;100%
With SBA-15-Ph-Pr-SO3H at 20℃; for 0.833333h;100%
With magnesium(II) perchlorate at 20℃; for 1.5h;99%
1,2,3,4-tetrahydronaphthalen-1-amine
2217-40-5

1,2,3,4-tetrahydronaphthalen-1-amine

acetic anhydride
108-24-7

acetic anhydride

N-(1,2,3,4-tetrahydro-1-naphthyl)acetamide
42071-43-2

N-(1,2,3,4-tetrahydro-1-naphthyl)acetamide

Conditions
ConditionsYield
In dichloromethane at 0 - 25℃; for 1h;100%
p-cresol
106-44-5

p-cresol

acetic anhydride
108-24-7

acetic anhydride

1-acetoxy-4-methylbenzene
140-39-6

1-acetoxy-4-methylbenzene

Conditions
ConditionsYield
With pyridine at 100℃; for 15h;100%
at 20℃; for 0.666667h;100%
With pyridine at 25℃; for 12h;100%

108-24-7Relevant articles and documents

Carbonylation of methyl acetate in the presence of polymeric rhodium-containing catalysts

Kolesnichenko, N. V.,Batov, A. E.,Markova, N. A.,Slivinsky, E. V.

, p. 259 - 262 (2002)

New catalytic systems based on RhCL3 and polymeric nitrogen- and oxygen-containing supports were proposed for the carbonylation of methyl acetate to acetic anhydride. The catalytic systems possess a high activity typical of homogeneous catalysts. The high activity is retained upon the repeated use of the catalyst separated from the reaction products. The nitrogen-containing polymers of the chitosan type serve as cocatalysts. In their presence, the induction period disappears, and the catalytically active species are stabilized, thus enabling the replacement of expensive LiI for cheaper salts of this metal.

Concerted General Acid Catalysis in the Reaction of Acetate Ion with Water-soluble Carbodi-imide

Ibrahim, Ibrahim T.,Williams, Andrew

, p. 25 - 27 (1980)

An intermediate, identified as an O-acetylisourea, is observed spectroscopically in the reaction of a water-soluble carbodi-imide with acetate buffers; a stepwise mechanism for intermediate formation as currently accepted is excluded by the observation of general acid catalysis, while acetate ion attack on carbodi-imide is concerted with proton transfer, and monoanions of dicarboxylic acids react with carbodi-imide with intramolecular concerted proton transfer.

-

Adkins,Thompson

, p. 2242 (1949)

-

Selectivity Behavior in Hydrocarbonylation of Methyl Acetate Using Homogeneous Rh Complex Catalyst

Kelkar, A. A.,Chaudhari, R. V.

, p. 334 - 343 (1995)

Hydrocarbonylation of methyl acetate using various homogeneous transition metal complex catalysts has been studied.It was observed that Rh(CO)Cl(PPh3)2 was the most active and selective catalyst for ethylidene diacetate synthesis.The effect of the catalyst, methyl acetate, and methyl iodide concentrations; temperature; and partial pressures of CO, H2, and various transition metal complexes as co-catalysts on the selectivity behavior has been studied.Palladium complexes were found to enhance the selectivity of ethylidene diacetate substantially.Catalyst concentration, partial pressures of CO and H2, and temperature also influence the selectivity pattern substantially.On the basis of these results, a possible reaction mechanism is discussed.

Technological features of the reaction of α-tocopherol acetylation

Bulychev

, p. 331 - 332 (1998)

-

-

Kremann,Roesler

, p. 359 (1922)

-

TRIOXABICYCLO PENTANE IH PHOTOSENSITIZED OXYGENATION OF 2-DIAZO-3-BUTANONE

Ando, Wataru,Miyazaki, Hajime,Ito, Kenji,Auchi, Daikan

, p. 555 - 556 (1982)

Photosensitized oxygenation of 2-diazo-3-butanone at -78 deg C in CH2Cl2 gave trioxabicyclo pentane which has a long enough life time to allow chemical and spectroscopic characterization.

Adsorption of ethanoic acid on zeolites NaY and HY

Pope, Christopher G.

, p. 3647 - 3651 (1996)

The enthalpy and entropy of adsorption of ethanoic acid by the zeolite HY do not appear to be strongly influenced by the geometric constraints of the pore system. These results, which were predicted previously, contrast with those on H-ZSM-5. A companion examination of adsorption by NaY was complicated by chemical reactions which produced small amounts of ethanoate ions, water, ethanoic anhydride and methane. These products were not observed on HY. The intensity of FTIR absorption bands in the frequency range 1850-1250 cm-1, which resulted from adsorption of ethanoic acid on NaY, depended strongly on adsorbed molecule concentration and were time dependent. Spectra were simpler, and less intense at the same surface concentration on HY.

-

Anderson

, p. 2371 (1952)

-

FORMATION OF ACETIC ANHYDRIDE BY CARBONYLATION OF METHYL ACETATE

Mamyan, V. A.,Sominskii, S. D.,Pirozhkov, S. D.,Barsegyan, V. L.,Vardanyan, V. D.,Lapidus, A. L.

, p. 2095 - 2098 (1985)

-

Mass Spectra and Pyrolyses of Some Vinylene Carbonates

Breitbeil, Fred W.,Skrobot, Angeline A.

, p. 702 - 704 (1982)

The mass spectra of a series of 1,3-dioxol-2-ones were examined for evidence of oxirenes in the fragmentation process.The M-cation radical-CO2 (oxirene or isomers) fragment was observed in six of eight samples.Four major pathways explain the mass spectra: M-cation radical-CO2-CO, M-cation radical-C2O3, M-cation radical-C2O2R and M-cation radical-CO-CO2.Metastable peaks support this.Similar pathways on pyrolysis were sought and observed.At 800 deg C and pressure of 1.5-4 mm, 1,3-dioxol-2-ones 1-3 and 5-7 were pyrolyzed in a stream of helium.The major products were, respectively, ketene (R1=R2=H), propene (R1=R2=CH3), fluorene (R1=R2=C6H5), ethene (R1=H, R2=CH3), stilbene (R1=H, R2=C6H5), and styrene (R1=CH3, R2=C6H5).Apparently the 1,3-dioxol-2-ones lose CO2 and CO successively to produce a carbene which either rearranges or dimerizes.

-

Fleming,Philippides

, p. 2426 (1970)

-

Ctc-[Pt(NH3)2(cinnamate)(valproate)Cl2] is a highly potent and low-toxic triple action anticancer prodrug

Li, Yang,Shi, Shan,Zhang, Shurong,Gan, Zongjie,Wang, Xin,Zhao, Xudong,Zhu, Yijian,Cao, Meiting,Wang, Xiaoyue,Li, Wei

, p. 11180 - 11188 (2021)

Pt(iv) prodrugs have gained tremendous attention due to their indisputable advantages compared to cisplatin. Herein, new Pt(iv) derivatives with cinnamic acid at the first axial position, and inhibitor of matrix metalloproteinases-2 and-9, histone deacetylase, cyclooxygenase or pyruvate dehydrogenase at the second axial position are constructed to develop multi-action prodrugs. We demonstrate that Pt(iv) prodrugs are reducible and have superior antiproliferative activity with IC50 values at submicromolar concentrations. Notably, Pt(iv) prodrugs exhibit highly potent anti-tumour activity in an in vivo breast cancer model. Our results support the view that a triple-action Pt(iv) prodrug acts via a synergistic mechanism, which involves the effects of CDDP and the effects of axial moieties, thus jointly leading to the death of tumour cells. These findings provide a practical strategy for the rational design of more effective Pt(iv) prodrugs to efficiently kill tumour cells by enhancing their cellular accumulation and tuning their canonical mechanism.

Stromnova, T. A.,Vargaftik, M. N.,Moiseev, I. I.

, (1983)

87. Novel aplysinopsin-type alkaloids from scleractinian corals of the family Dendrophylliidae of the Mediterranean and the Philippines. Configurational-assignment criteria, stereospecific synthesis, and photoisomerization

Guella,Mancini,Zibrowius,Pietra

, p. 773 - 782 (1988)

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Dicarboxylic Acids Link Proton Transfer Across a Liquid Membrane to the Synthesis of Acyl Phosphates. A Model for P-Type H(+)-ATPases

Colton, Ian J.,Kazlauskas, Romas J.

, p. 3626 - 3635 (1994)

H(+)-ATPases are ion pumps that link proton transfer across cell membranes to the synthesis or hydrolysis of ATP.A current research goal is to understand the molecular-level mechanism of this linking.We present a chemical model that mimics some features of H(+)-ATPases by linking proton transfer across a liquid membrane to the synthesis of acyl phosphates using carboxylic acid anhydride intermediates.Citraconic acid (cis-2-methyl-2-butenedioic acid) accelerated the transfer of protons from a pH 0.3 solution across a chloroform liquid membrane to a pH 10 solution.The mechanism involved spontaneous formation of a small amount of citraconic anhydride (0.6percent) in the pH 0.3 layer.This anhydride partitioned into the chloroform layer and diffused to the pH 10 layer, where it hydrolyzed, generating two protons.When the pH 10 layer contained phosphate (1.0 M), some of the citraconic anhydride reacted with phosphate to form citraconyl phosphate, 5.0percent yield.In separate experiments, we confirmed that citraconyl phosphate had high phosphoryl donor potential by reacting it with morpholine to form a phosphoramidate (11.5percent yield) or with fluoride to form fluorophosphonate (32percent yield).To demonstrate the link between an acyl phosphate and a proton gradient in the reverse direction, we used succinyl phosphate, whose hydrolysis occurs in two steps: formation of succinic anhydride, which consumes protons, followed by hydrolysis of succinic anhydride, which releases protons.We generated a pH gradient by carrying out these two steps in separate solutions.Hydrolysis of succinyl phosphate (3.9 mmol) at pH 6.00 started with a increase in pH to 6.16 (0.59 mmol of H(+) consumed) caused by the formation of succinic anhydride.We extracted this anhydride with dichloromethane and transferred it to a separate solution at pH 6.05.Hydrolysis of the anhydride released protons (0.36 mmol), decreasing the pH to 5.23.Our model suggests that H(+)-ATPases could use acyl phosphates and carboxylic acid anhydride intermediates to link proton transfer to ATP synthesis or hydrolysis.

Electrophilic Substitution of Polycyclic Fluoranthene Hydrocarbons

Minabe, Masahiro,Cho, Bongsup P.,Harvey, Ronald G.

, p. 3809 - 3812 (1989)

The first systematic study of the sites of electrophilic substitution (acylation and/or bromination) of polycyclic fluoranthene hydrocarbons is described.The hydrocarbons studied include indenopyrene (1), benzaceanthrylene (2), benzacephenanthrylene (3), and indenochrysene (4).Compounds 1-4 all undergo bromination regioselectively in a single site.The latter are determined by conversion of the bromo derivatives to monodeuterio analogues by metal exchange with butyllithium and analysis of their high-resolution 1H and 13C NMR spectra in comparison with those of the parent hydrocarbons.This method is potentially generally applicable to determination of the sites of substitution of other complex polycyclic hydrocarbon ring systems.Acylation of 1 is shown to take place in the same site as bromination, i.e., the 12-position.For 2 and 4, substitution occurs in the 8- and 5-positions, respectively, in good agreement with theoretical prediction by the DEWAR-PI method based on the relative energies of the Wheland intermediates for substitution at various ring positions.However, for 1 and 3 the principal sites of bromination observed experimentally are the 12- and 1-positions, respectively, which do not accord with theoretical prediction of the 3,5- and 8-positions, respectively.In the latter cases, the observed sites of bromination are only slightly less favorable energetically than the theoretically calculated sites and are probably within the limit of accuracy of the calculations.

-

Kirshenbaum et al.

, p. 3141,3143 (1953)

-

Linear-reactor-infrared-matrix and Microwave Spectroscopy of the cis-2-Butene Gas-phase Ozonolysis

Kuehne, Heinz,Forster, Martin,Hulliger, Juerg,Ruprecht, Heidi,Bauder, Alfred,Guenthard, Hans-Heinrich

, p. 1971 - 1999 (1980)

Investigation of the formation of complex products in the gas-phase ozonolysis of cis-2-butene by linear-reactor-infrared-matrix and linear-reactor-microwave spectroscopy is reported.The following species have been unequivocally detected: secondary 2-butene ozonide, acetic acid, peracetic acid, glycolaldehyde, dimethyl ketene, the simple mixed anhydrides of formic and acetic acid, 2,3-epoxy-butane and 2-butanone, besides polyatomic products alredy known.In contrast, the primery ozonide has been detectable neither by LR.-MW. nor by LR.-IR.Observation of both stereoisomeric epoxides and kinetic modelling are used to support the intermediate formation of the O'Neal-Blumstein radical CH3CH(O2)CH(O)CH3 and the existence of a reaction channel in which the two carbon atoms of the C,C double bond of the olefin remain connected.As the dominant reaction path a mechanism with a Criegee type split into methyldioxirane (ethylidene peroxide) and acetaldehyde is considered and subsequently proposed to explain formation of many complex products by either unimolecular or bimolecular processes of the peroxide.For the reactions considered, thermochemical estimates of reaction enthalpies and activation data are included.Kinetic modelling for a partial reaction mechanism involving at least two different paths of decay of the O'Neal-Blumstein biradical into Criegee-type intermediates and the 2,3-epoxy-butanes is discussed.

Oxidation of ethyl ether on borate glass: Chemiluminescence, mechanism, and development of a sensitive gas sensor

Hu, Jing,Xu, Kailai,Jia, Yunzhen,Lv, Yi,Li, Yubao,Hou, Xiandeng

, p. 7964 - 7969 (2008)

A gas sensor was developed by using the chemiluminescence (CL) emission from the oxidation of ethyl ether by oxygen in the air on the surface of borate glass. Theoretical calculation, together with experimental investigation, revealed the main CL reactions: ethyl ether is first oxidized to acetaldehyde and then to acetic acid, during which main luminous intermediates such as CH3CO? are generated and emit light with a peak at 493 nm. At a reaction temperature of 245°C, the overall maximal emission was found at around 460 nm, and the linear range of the CL intensity versus the concentration of ethyl ether was 0.12-51.7 μg mL-1 (R = 0.999, n = 7) with a limit of detection (3σ) of 0.04 μg mL-1. Interference from foreign substances including alcohol (methanol, ethanol and isopropanol), acetone, ethyl acetate, n-hexane, cyclohexane, dichloromethane, or ether (n-butyl ether, tetrahydrofuran, propylene oxide, isopropyl ether and methyl tert-butyl ether) was not significant except a minimal signal from n-butyl ether (a simple, sensitive and selective gas sensor for the determination of trace ethyl ether.

Atmospheric chemistry of two biodiesel model compounds: Methyl propionate and ethyl acetate

Andersen, Vibeke F.,Berhanu, Tesfaye A.,Nilsson, Elna J. K.,Jorgensen, Solvejg,Nielsen, Ole John,Wallington, Timothy J.,Johnson, Matthew S.

, p. 8906 - 8919 (2011)

The atmospheric chemistry of two C4H8O2 isomers (methyl propionate and ethyl acetate) was investigated. With relative rate techniques in 980 mbar of air at 293 K the following rate constants were determined: k(C2H5C(O)OCH3 + Cl) = (1.57 ± 0.23) × 10-11, k(C2H5C(O) OCH3 + OH) = (9.25 ± 1.27) × 10-13, k(CH 3C(O)OC2H5 + Cl) = (1.76 ± 0.22) × 10-11, and k(CH3C(O)OC2H5 + OH) = (1.54 ± 0.22) × 10-12 cm3 molecule -1 s-1. The chlorine atom initiated oxidation of methyl propionate in 930 mbar of N2/O2 diluent (with, and without, NOx) gave methyl pyruvate, propionic acid, acetaldehyde, formic acid, and formaldehyde as products. In experiments conducted in N 2 diluent the formation of CH3CHClC(O)OCH3 and CH3CCl2C(O)OCH3 was observed. From the observed product yields we conclude that the branching ratios for reaction of chlorine atoms with the CH3-, -CH2-, and -OCH3 groups are 9 ± 2%, respectively. The chlorine atom initiated oxidation of ethyl acetate in N2/O 2 diluent gave acetic acid, acetic acid anhydride, acetic formic anhydride, formaldehyde, and, in the presence of NOx, PAN. From the yield of these products we conclude that at least 41 ± 6% of the reaction of chlorine atoms with ethyl acetate occurs at the -CH2- group. The rate constants and branching ratios for reactions of OH radicals with methyl propionate and ethyl acetate were investigated theoretically using transition state theory. The stationary points along the oxidation pathways were optimized at the CCSD(T)/cc-pVTZ//BHandHLYP/aug-cc-pVTZ level of theory. The reaction of OH radicals with ethyl acetate was computed to occur essentially exclusively (~99%) at the -CH2- group. In contrast, both methyl groups and the -CH2- group contribute appreciably in the reaction of OH with methyl propionate. Decomposition via the α-ester rearrangement (to give C2H5C(O)OH and a HCO radical) and reaction with O 2 (to give CH3CH2C(O)OC(O)H) are competing atmospheric fates of the alkoxy radical CH3CH2C(O)OCH 2O. Chemical activation of CH3CH2C(O)OCH 2O radicals formed in the reaction of the corresponding peroxy radical with NO favors the α-ester rearrangement.

Ozonolyses of acetylenes revisited

Griesbaum, Karl,Dong, Yuxiang

, p. 575 - 577 (1997)

-

-

Karrer,Hohl

, p. 1933 (1949)

-

A transesterification-acetalization catalytic tandem process for the functionalization of glycerol: The pivotal role of isopropenyl acetate

Calmanti, Roberto,Perosa, Alvise,Rigo, Davide,Selva, Maurizio

supporting information, p. 5487 - 5496 (2020/09/23)

At 30 °C, in the presence of Amberlyst-15 as a catalyst, a tandem sequence was implemented by which a pool of innocuous reactants (isopropenyl acetate, acetic acid and acetone) allowed upgrading of glycerol through selective acetylation and acetalization processes. The study provided evidence for the occurrence of multiple concomitant reactions. Isopropenyl acetate acted as a transesterification agent to provide glyceryl esters, and it was concurrently subjected to an acidolysis reaction promoted by AcOH. Both these transformations co-generated acetone which converted glycerol into the corresponding acetals, while acidolysis sourced also acetic anhydride that acted as an acetylation reactant. However, tuning of conditions, mostly by changing the reactant molar ratio and optimizing the reaction time, was successful to steer the set of all reactions towards the synthesis of either a 1?:?1 mixture of acetal acetates (97% of which was solketal acetate) and triacetin, or acetal acetates in up to 91% yield, at complete conversion of glycerol. To the best of our knowledge, a one-pot protocol with such a degree of control on the functionalization of glycerol via transesterification and acetalization reactions has not been previously reported. The procedure was also easily reproduced on a gram scale, thereby proving its efficiency for preparative purposes. Finally, the design of experiments with isotopically labelled reagents, particularly d4-acetic acid and d6-acetone, helped to estimate the contribution of different reaction partners (iPAc/AcOH/acetone) to the formation of final products. This journal is

Production of acetic anhydride

-

Paragraph 0067-0069, (2017/06/27)

An object is to provide a method for producing a ketene derivative that decreases the consumption quantity of phosphorus compounds, and the discharge quantity of the phosphorus compounds into the environment. A method for producing a ketene derivative includes a step (i) of conducting thermal decomposition reaction of acetic acid in a presence of a phosphorus-containing catalyst in a reactor to produce a thermal decomposition gas containing ketene, a step (ii) of cooling the thermal decomposition gas to be separated into a gaseous component containing ketene, and a condensed liquid containing a phosphorus compound (a), and a step (iii) of causing the ketene to react with a different organic compound to produce a ketene derivative. The step (i) includes conducting the thermal decomposition reaction while supplying, into the reactor, the condensed liquid containing the phosphorus compound (a) or a concentrated liquid of the condensed liquid.