Conditions | Yield |
---|---|
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
A
tetraphenylethane-1,2-diol
B
acetic anhydride
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
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
A
acetic anhydride
Conditions | Yield |
---|---|
With stannic bromide In dichloromethane for 72h; Product distribution; Ambient temperature; | A n/a B n/a C 90% |
B
acetic anhydride
Conditions | Yield |
---|---|
A n/a B 90% | |
A n/a B 90% |
diphenyltellurium di(acetate)
A
diphenyltellurium dichloride
B
acetic anhydride
Conditions | Yield |
---|---|
With acetyl chloride In chloroform for 5h; Heating; | A 89% B 81% |
acetic acid
N,N,N',N'-tetraethyl-P-(trichloromethyl)phosphonoimidic diamide
A
chloroform
B
N,N,N',N'-tetraethylphosphoric triamide
C
acetic anhydride
Conditions | Yield |
---|---|
In diethyl ether for 3h; Ambient temperature; | A 89% B 51% C n/a |
O-acetyl S,S-diethyl phosphorodithioite
A
diethyl phosphorochloridodithioite
B
acetic anhydride
Conditions | Yield |
---|---|
With acetyl chloride for 0.5h; Ambient temperature; | A 72% B 89% |
O-acetyl S,S-diethyl phosphorodithioite
acetyl chloride
A
diethyl phosphorochloridodithioite
B
acetic anhydride
Conditions | Yield |
---|---|
at 20℃; for 0.5h; | A 72% B 89% |
(Acetoxy)diphenylphosphane
A
acetic anhydride
Conditions | Yield |
---|---|
With tin(IV) chloride In dichloromethane for 72h; Product distribution; Ambient temperature; | A n/a B n/a C 88% |
Conditions | Yield |
---|---|
In diethyl ether; ethyl acetate at 20℃; for 0.25h; | 87% |
O-acetyl-α-hydroxyisobutyric acid
A
diethylacetamide
B
2,3-dimethyl-2,3-butane diol
C
Essigsaeure-2-hydroxy-1,1,2-trimethylpropylester
D
acetic anhydride
Conditions | Yield |
---|---|
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
triethylamine
A
diethylacetamide
B
2,3-dimethyl-2,3-butane diol
C
Essigsaeure-2-hydroxy-1,1,2-trimethylpropylester
D
acetic anhydride
Conditions | Yield |
---|---|
In acetonitrile Ambient temperature; electrolysis; Further byproducts given; | A 47% B 86.8% C 4.7% D n/a |
Conditions | Yield |
---|---|
With dinitrogen tetraoxide In neat (no solvent) byproducts: N2O3; addn. of N2O4 to dry Na acetate;; | A n/a B 85% |
Conditions | Yield |
---|---|
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
O-acetyl S,S-dipropyl phosphorodithioite
A
acetic anhydride
Conditions | Yield |
---|---|
A 82% B 69% | |
at 25℃; Product distribution; various time, with or without acetic acid or pyridine; |
O-acetyl S,S-dipropyl phosphorodithioite
A
acetic anhydride
Conditions | Yield |
---|---|
With Acetyl bromide for 1h; Ambient temperature; | A 82% B 69% |
Conditions | Yield |
---|---|
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
3-diazo-2-butanone
A
1,1'-sulfinylbisbenzene
B
acetic anhydride
C
dimethylglyoxal
Conditions | Yield |
---|---|
With oxygen at -78 - 25℃; Product distribution; Mechanism; TPP as sensitizer; | A 19% B 5% C 76% |
formaldehyd
dimethylacetylene
A
diacetoxymethane
B
acetic anhydride
C
acetic acid
D
dimethylglyoxal
Conditions | Yield |
---|---|
With ozone In dichloromethane at -100℃; | A 7% B 71% C 17% D 5% |
acetoxyacetic acid
acetonitrile
A
formaldehyd
B
acetic anhydride
C
acetic acid
D
Essigsaeure-(diacetylamino)methylester
E
Acetoxyessigsaeure-acetoxymethylester
F
Essigsaeure-methylester
Conditions | Yield |
---|---|
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
carbon monoxide
A
1,1-diacetoxy-1-ethyl methane
B
acetic anhydride
Conditions | Yield |
---|---|
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.; |
Conditions | Yield |
---|---|
In acetone byproducts: (C6H11NH)2CO; at room temp.;; | A n/a B 68% |
Conditions | Yield |
---|---|
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
1-ethoxyacetylene
A
1-ethoxyvinyl acetate
B
acetic anhydride
Conditions | Yield |
---|---|
[ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 In tetrahydrofuran at 40℃; for 15h; | A 65% B n/a |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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
acetic anhydride
2-acetylamino-6-methylpyridine
Conditions | Yield |
---|---|
at 60 - 70℃; for 1.5h; | 100% |
In tetrahydrofuran for 10h; Heating / reflux; Acidic aqueous solution; | 99% |
at 90℃; for 1.5h; | 98% |
Conditions | Yield |
---|---|
at 120℃; for 0.5h; | 100% |
2-(N-methylamino)pyridine
acetic anhydride
2-[(N-acetyl-N-methyl)amino]pyridine
Conditions | Yield |
---|---|
at 70℃; for 4h; | 100% |
With acetic acid |
Conditions | Yield |
---|---|
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
acetic anhydride
3,4-furan dimethanol diacetate
Conditions | Yield |
---|---|
With pyridine | 100% |
With sodium acetate | |
With pyridine |
Conditions | Yield |
---|---|
for 15h; | 100% |
With triethylamine for 0.5h; | 90% |
With hydrogenchloride for 0.25h; Heating; | 79.9% |
Conditions | Yield |
---|---|
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
acetic anhydride
N-acetyl-6-aminobenzothiazole
Conditions | Yield |
---|---|
With pyridine at 20℃; | 100% |
With silica-supported boric acid In neat (no solvent) at 50℃; for 1h; | 96% |
Conditions | Yield |
---|---|
for 15h; Acetylation; Heating; | 100% |
Reflux; | 99% |
at 138℃; for 5h; | 95% |
3-bromo-9H-carbazole
acetic anhydride
1-(3-bromo-9H-carbazol-9-yl)ethan-1-one
Conditions | Yield |
---|---|
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
acetic anhydride
4-methylumbelliferyl acetate
Conditions | Yield |
---|---|
With pyridine; dmap | 100% |
With sodium hydroxide for 0.0125h; microwave irradiation; | 99% |
With SiO2-supported Co(II) Salen complex catalyst at 50℃; for 0.75h; | 99% |
Conditions | Yield |
---|---|
With sulfuric acid for 4h; | 100% |
With sulfuric acid |
5-chloro-7-iodoquinolin-8-ol
acetic anhydride
5-chloro-7-iodoquinolin-8-yl ethanoate
Conditions | Yield |
---|---|
With pyridine at 60℃; for 0.0833333h; | 100% |
at 150℃; for 5h; | 94% |
With pyridine |
methyl 3,4-O-isopropylideneshikimate
acetic anhydride
(3aR,7R,7aS)-methyl 7-acetoxy-2,2-dimethyl-3a,6,7,7atetrahydrobenzo[d][1,3]dioxole-5-carboxylate
Conditions | Yield |
---|---|
With dmap In dichloromethane for 2h; Ambient temperature; | 100% |
With pyridine at 20℃; for 1h; | 100% |
With pyridine |
phenylmethyl 1-piperazinecarboxylate
acetic anhydride
Conditions | Yield |
---|---|
With pyridine at 20℃; for 18h; | 100% |
With benzene | |
With pyridine at 20℃; for 18h; |
4',5,7-trihydroxy-8-methoxyisoflavone
acetic anhydride
5,7-diacetoxy-3-(4-acetoxy-phenyl)-8-methoxy-chromen-4-one
Conditions | Yield |
---|---|
With pyridine | 100% |
With pyridine |
quercetol
acetic anhydride
3,5,7-triacetoxy-2-(3,4-diacetoxy-phenyl)-chromen-4-one
Conditions | Yield |
---|---|
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
acetic anhydride
1-(5-O-Acetyl-2,3-O-isopropylidene-β-D-ribofuranosyl)uracil
Conditions | Yield |
---|---|
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 pyridine | 61% |
With pyridine |
3,4-methylenedioxyphenylethylamine
acetic anhydride
N-[2-(3,4-methylenedioxyphenyl)ethyl]acetamide
Conditions | Yield |
---|---|
In toluene at 20℃; | 100% |
Conditions | Yield |
---|---|
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
acetic anhydride
(E)-3-<2-(acetyloxy)phenyl>-2-propenoic acid
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
at 60℃; for 1h; Inert atmosphere; | 100% |
at 0 - 60℃; for 3.5h; | 78% |
at 50℃; Fraktionierung im Vakuum; |
Conditions | Yield |
---|---|
With sulfuric acid In water at 0 - 100℃; for 0.5h; Temperature; Reagent/catalyst; Solvent; | 100% |
With hydrogenchloride; acetic acid |
Conditions | Yield |
---|---|
With sulfuric acid for 0.5h; Ambient temperature; | 100% |
With sulfuric acid | |
With sodium acetate |
alpha-D-mannopyranoside
acetic anhydride
per-O-acetyl-α-D-mannopyranose
Conditions | Yield |
---|---|
With pyridine; dmap | 100% |
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% |
Conditions | Yield |
---|---|
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
acetic anhydride
N-(1,2,3,4-tetrahydro-1-naphthyl)acetamide
Conditions | Yield |
---|---|
In dichloromethane at 0 - 25℃; for 1h; | 100% |
Conditions | Yield |
---|---|
With pyridine at 100℃; for 15h; | 100% |
at 20℃; for 0.666667h; | 100% |
With pyridine at 25℃; for 12h; | 100% |
Molecular Structure:
Molecular Formula: C4H6O3
Molecular Weight: 102.09
IUPAC Name: Acetyl acetate
Synonyms of Acetic anhydride (CAS NO.108-24-7): Acetanhydride ; Acetic acid, anhydride ; Acetic oxide ; Acetyl acetate ; Anhydride acetique ; Anidride acetica ; Essigsaeureanhydrid ; Acetic acid, 1,1'-anhydride
CAS NO: 108-24-7
EINECS: 203-564-8
H bond acceptors: 3
H bond donors: 0
Freely Rotating Bonds: 2
Polar Surface Area: 43.37 Å2
Index of Refraction: 1.386
Molar Refractivity: 22.38 cm3
Molar Volume: 95.1 cm3
Surface Tension: 29.1 dyne/cm
Density: 1.072 g/cm3
Flash Point: 54.4 °C
Enthalpy of Vaporization: 37.83 kJ/mol
Boiling Point: 141.1 °C at 760 mmHg
Vapour Pressure: 5.94 mmHg at 25°C
Melting Point: -73.1 °C
Storage temp: Store at RT.
Water Solubility: REACTS
Sensitive: Moisture Sensitive
Stability: Stability Flammable. Incompatible with strong oxidizing agents, water, strong bases, alcohols.
Appearance: Colorless liquid
Product Categories of Acetic anhydride (CAS NO.108-24-7): Pharmaceutical Intermediates;Biochemistry;Reagents for Oligosaccharide Synthesis;Chemistry;Acylation ReagentsDerivatization Reagents GC;AminesDerivatization Reagents;GC Derivatization Reagents, by Application;Acylation ReagentsDerivatization Reagents;Analytical/Chromatography;Derivatization Reagents;Derivatization Reagents GC;Reagents for Acylation;ACS GradeOrganic Building Blocks;Carbonyl Compounds;Carboxylic Acid Anhydrides;Essential Chemicals;Routine Reagents;A-B, Puriss p.a. ACSDerivatization Reagents;Analytical Reagents for General Use;Derivatization Reagents HPLC;Puriss p.a. ACS;UV-VIS;A-B, Puriss p.a. ACSAnalytical/Chromatography;Reagent Plus;Alkaline β-eliminationFatty Acids;AnhydridesDeglycosylation Strategies;Reagent GradeProtein Modification;Reagents for lysine modification;Chemical Deglycosylation;Deglycosylation Strategies;HydrazinolysisEssential Chemicals;Saturated fatty acids and derivatives;Specific Amino Acid Modification
Acetic anhydride (CAS NO.108-24-7) is mainly used for acetylations leading to commercially significant materials. It is mainly used for the conversion of cellulose to cellulose acetate, which is a component of photographic film and other coated materials. For the same reason it is used in the production of aspirin, acetylsalicylic acid, which is prepared by the acetylation of salicylic acid. It is also used as a wood preservative via autoclave impregnation to make a longer lasting timber. In starch industry, Acetic anydride is a common acetylation compound, used for the production of modified starches.
Acetic anhydride (CAS NO.108-24-7) may be produced by three different methods.
The first procedure involves the in situ production from acetaldehyde of peracetic acid, which in turn reacts with more acetaldehyde to yield the anhydride.
CH3CH=O + O2 → CH3C(=O)OH
CH3C(=O)OH + CH3C=O → CH3C(=O)O(O=)CCH3 + H2O
In the preferred process, acetic acid (or acetone) is pyrolyzed to ketene, which reacts with acetic acid to form acetic anhydride.
CH3C(=O)OH → CH2=C=O + H2O
CH2=C=O + CH3C(=O)OH → CH3C(=O)O(O=)CCH3
Another process to make acetic anhydride involves carbon monoxide insertion into methyl acetate.
CH3C(=O)OCH3 → CH3C(=O)O(O=)CCH3
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
rabbit | LD50 | skin | 4mL/kg (4mL/kg) | Union Carbide Data Sheet. Vol. 8/7/1963, | |
rat | LC50 | inhalation | 1000ppm/4H (1000ppm) | "Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 607, 1969. | |
rat | LD50 | oral | 1780mg/kg (1780mg/kg) | AMA Archives of Industrial Hygiene and Occupational Medicine. Vol. 4, Pg. 119, 1951. |
Hazard Codes: C,Xn,F,Xi
Risk Statements: 10-11-19-34-41-37/38-20/21/22
R10: Flammable.
R11: Highly flammable.
R19: May form explosive peroxides.
R34: Causes burns.
R41: Risk of serious damage to the eyes.
R37/38: Irritating to respiratory system and skin.
R20/21/22: Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 26-16-33-45-36/37/39
S16: Keep away from sources of ignition.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S33: Take precautionary measures against static discharges.
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.
RIDADR: UN 2924 3/PG 2
WGK Germany: 3
RTECS: AK1925000
F: 21
HazardClass: 8
PackingGroup: II
HS Code: 29152400
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