Acetyl ketene supplier | CasNO.674-82-8

Name
Acetyl ketene
EINECS 211-617-1
CAS No. 674-82-8
Article Data28
CAS DataBase
Density 1.10 g/cm³
Solubility soluble in water and organic solvents
Melting Point -7.5 °C
Formula C₄H₄O₂
Boiling Point 127.4 °C at 760 mmHg
Molecular Weight 84.0746
Flash Point 97.9 °C
Transport Information UN 2929 6.1/PG 2
Appearance colorless liquid
Safety 3-36/37-33-24/25-23-16
Risk Codes 10-20-40
Molecular Structure
Hazard Symbols Xn
Synonyms 3-Butenoicacid, 3-hydroxy-, b-lactone (6CI,7CI);4-Methylene-2-oxetanone;Diketene;Ethenone, dimer;Ketene dimer;NSC 93783;
PSA 26.30000
LogP 0.44700

Synthetic route

: bis(triphenylphosphine)-3,3-dimethylnickelacyclobutane

A: 674-82-8
4-methyleneoxetan-2-one

B: 13007-90-4
bis(triphenylphosphine)nickel(0) dicarbonyl

C: 115-11-7
isobutene

Conditions

Conditions	Yield
With carbon monoxide In toluene High Pressure; 5 atm CO, 50°C, 1 h; pptn. of complex;	A 8% B 83% C n/a

...Expand

: 463-51-4
Ketene

: 674-82-8
4-methyleneoxetan-2-one

Conditions

Conditions	Yield
With N,N,N,N,-tetramethylethylenediamine In hexane at -15 - -10℃; for 3.5h;	75%

: 463-51-4
Ketene

: 108-24-7
acetic anhydride

: 674-82-8
4-methyleneoxetan-2-one

: 463-51-4
Ketene

: 925-90-6
ethylmagnesium bromide

: 674-82-8
4-methyleneoxetan-2-one

: 1971-49-9
N-acetylphthalimide

: 674-82-8
4-methyleneoxetan-2-one

Conditions

Conditions	Yield
at 325℃;

: 574-39-0
9-acetylcarbazole

: 674-82-8
4-methyleneoxetan-2-one

Conditions

Conditions	Yield
at 110℃; under 15 Torr;

: 463-51-4
Ketene

: 106-99-0
buta-1,3-diene

A: 674-82-8
4-methyleneoxetan-2-one

B: 66166-61-8
3-vinylcyclobutanone

Conditions

Conditions	Yield
With nitrogen at 100℃;

...Expand

: 121-44-8
triethylamine

: 75-36-5
acetyl chloride

: 674-82-8
4-methyleneoxetan-2-one

Conditions

Conditions	Yield
With diethyl ether

: 75-36-5
acetyl chloride

: 75-50-3
trimethylamine

: 674-82-8
4-methyleneoxetan-2-one

Conditions

Conditions	Yield
With diethyl ether

: 463-51-4
Ketene

: 67-64-1
acetone

: 674-82-8
4-methyleneoxetan-2-one

: 75-09-2
dichloromethane

: 201230-82-2
carbon monoxide

: 674-82-8
4-methyleneoxetan-2-one

Conditions

Conditions	Yield
Pd(PCy3)2(dba) In benzene-d6 at 25℃; under 22501.8 Torr;

: 2415-85-2
3-oxo-N-(p-tolyl)butanamide

A: 674-82-8
4-methyleneoxetan-2-one

B: 106-49-0
p-toluidine

Conditions

Conditions	Yield
In cyclohexane at 25℃; Equilibrium constant;

: 101-92-8
4'-Chloroacetoacetanilide

A: 674-82-8
4-methyleneoxetan-2-one

B: 106-47-8
4-chloro-aniline

Conditions

Conditions	Yield
In cyclohexane at 25℃; Equilibrium constant;

: 38418-24-5
N-(4-bromophenyl)-3-oxobutyramide

A: 674-82-8
4-methyleneoxetan-2-one

B: 106-40-1
4-bromo-aniline

Conditions

Conditions	Yield
In cyclohexane at 25℃; Equilibrium constant;

: 5437-98-9
4'-methoxyacetoacetanilide

A: 674-82-8
4-methyleneoxetan-2-one

B: 104-94-9
4-methoxy-aniline

Conditions

Conditions	Yield
In cyclohexane at 25℃; Equilibrium constant;

: 25233-46-9
3-oxo-N-m-tolylbutanamide

A: 674-82-8
4-methyleneoxetan-2-one

B: 108-44-1
1-amino-3-methylbenzene

Conditions

Conditions	Yield
In cyclohexane at 25℃; Equilibrium constant;

: 25233-47-0
N-(3'-methoxyphenyl)-3-oxobutanamide

A: 674-82-8
4-methyleneoxetan-2-one

B: 536-90-3
m-Anisidine

Conditions

Conditions	Yield
In cyclohexane at 25℃; Equilibrium constant;

: 25233-49-2
3'-nitroacetoacetanilide

A: 674-82-8
4-methyleneoxetan-2-one

B: 99-09-2
3-nitro-aniline

Conditions

Conditions	Yield
In cyclohexane at 25℃; Equilibrium constant;

: 2415-87-4
3'-chloroacetoacetanilide

A: 674-82-8
4-methyleneoxetan-2-one

B: 108-42-9
3-chloro-aniline

Conditions

Conditions	Yield
In cyclohexane at 25℃; Equilibrium constant;

: 61579-06-4
N-(3-bromo-phenyl)-3-oxo-butyramide

A: 674-82-8
4-methyleneoxetan-2-one

B: 591-19-5
3-bromoaniline

Conditions

Conditions	Yield
In cyclohexane at 25℃; Equilibrium constant;

: N-(3-cyanophenyl)-3-oxobutanamide

A: 674-82-8
4-methyleneoxetan-2-one

B: 2237-30-1
m-cyanoaniline

Conditions

Conditions	Yield
In cyclohexane at 25℃; Equilibrium constant;

: 102-01-2
N-phenylacetoacetamide

A: 674-82-8
4-methyleneoxetan-2-one

B: 62-53-3
aniline

Conditions

Conditions	Yield
In cyclohexane at 25℃; Equilibrium constant;

: 463-49-0
1,2-propanediene

: 106-51-4
p-benzoquinone

A: 674-82-8
4-methyleneoxetan-2-one

B: 52727-24-9
Spiro<3.5>nona-5,8-dien-2,7-dion

C: 115077-69-5
3-Methylene-1-oxa-spiro[3.5]nona-5,8-dien-7-one

D: 115077-67-3
C15H12O4

Conditions

Conditions	Yield
In trichlorofluoromethane at -25℃; under 760 Torr; for 1h; Irradiation; Laser VIS-irradiation, 455-515 nm;	A n/a B n/a C 146 mg D 6.2 mg

...Expand

: 463-51-4
Ketene

: 75-07-0
acetaldehyde

H3BO3: H3BO3

A: 674-82-8
4-methyleneoxetan-2-one

B: 3068-88-0, 32082-74-9, 36536-46-6, 65058-82-4
4-methyloxetan-2-one

C: 625-33-2
3-penten-2-one

...Expand

: 463-51-4
Ketene

: 75-07-0
acetaldehyde

ZnCl2: ZnCl2

A: 674-82-8
4-methyleneoxetan-2-one

B: 3068-88-0, 32082-74-9, 36536-46-6, 65058-82-4
4-methyloxetan-2-one

C: 625-33-2
3-penten-2-one

...Expand

: 463-51-4
Ketene

: 7664-93-9
sulfuric acid

: 67-64-1
acetone

A: 674-82-8
4-methyleneoxetan-2-one

B: 108-22-5
Isopropenyl acetate

C: 108-24-7
acetic anhydride

D 4-oxo-2.2.6-trimethyl-1.3-dioxime: 4-oxo-2.2.6-trimethyl-1.3-dioxime

Conditions

Conditions	Yield
at 55℃;

...Expand

: 463-51-4
Ketene

: 67-64-1
acetone

ZnCl2: ZnCl2

A: 674-82-8
4-methyleneoxetan-2-one

B: 108-22-5
Isopropenyl acetate

C: 108-24-7
acetic anhydride

D 4-oxo-2.2.6-trimethyl-1.3-dioxime: 4-oxo-2.2.6-trimethyl-1.3-dioxime

Conditions

Conditions	Yield
at 100℃;

...Expand

: 463-51-4
Ketene

: 7732-18-5
water

A: 674-82-8
4-methyleneoxetan-2-one

B: 67-64-1
acetone

...Expand

: 112-16-3
n-dodecanoyl chloride

: 121-44-8
triethylamine

: 75-36-5
acetyl chloride

A: 674-82-8
4-methyleneoxetan-2-one

B dimer(ic) decylketene: dimer(ic) decylketene

C mixed diketene C14H24O2: mixed diketene C14H24O2

...Expand

: 674-82-8
4-methyleneoxetan-2-one

: 100-46-9
benzylamine

: 882-36-0
N-benzyl-3-oxobutanamide

Conditions

Conditions	Yield
In dichloromethane at 0 - 20℃;	100%
In dichloromethane at 0 - 20℃;	100%
In dichloromethane at 0 - 20℃;	100%

: 674-82-8
4-methyleneoxetan-2-one

: 108-01-0
2-(N,N-dimethylamino)ethanol

: 6131-49-3
acetoacetic acid 2-dimethylamino-ethyl ester

Conditions

Conditions	Yield
With dmap In tetrahydrofuran at 65℃; for 0.5h;	100%
at 70 - 71℃; for 5h;	99%
With triethylamine at 95℃; for 3h;	84%

: 674-82-8
4-methyleneoxetan-2-one

: 4360-51-4
cinnamylamine

: 26226-10-8
3-oxo-N-(3-phenyl-2-propen-1-yl) butylamide

Conditions

Conditions	Yield
With triethylamine In toluene at 70℃; for 3h;	100%
In diethyl ether

: 674-82-8
4-methyleneoxetan-2-one

: 109-89-7
diethylamine

: 2235-46-3
N,N-diethyl-3-oxobutanamide

Conditions

Conditions	Yield
In tetrahydrofuran at 0℃; Inert atmosphere;	100%
In tetrahydrofuran at 0℃; for 0.0833333h; Inert atmosphere;	100%
With triethylamine In methanol; toluene at 0℃; for 2h;	95%

: 674-82-8
4-methyleneoxetan-2-one

: 108-93-0
cyclohexanol

: 6947-02-0
cyclohexyl 3-oxobutanoate

Conditions

Conditions	Yield
With sodium acetate In tetrahydrofuran for 2h; Reflux;	100%
With triethylamine In chloroform for 10h; Ambient temperature;	96.7%
With triethylamine
With dmap

: 110-89-4
piperidine

: 674-82-8
4-methyleneoxetan-2-one

: 1128-87-6
1-(piperidin-1-yl)-butane-1,3-dione

Conditions

Conditions	Yield
In tetrahydrofuran at 20℃;	100%
for 2h; Yield given;
In toluene at 100℃; for 1h;
In tert-butyl methyl ether at -5 - 0℃; for 1h;	49.55 g

: 674-82-8
4-methyleneoxetan-2-one

: 2033-24-1
cycl-isopropylidene malonate

: 84257-12-5
2,2-dimethyl-5-(1-hydroxy-3-oxobutylidene)-1,3-dioxane-4,6-dione

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 2h;	100%
Stage #1: 4-methyleneoxetan-2-one; cycl-isopropylidene malonate With triethylamine In dichloromethane at 0 - 20℃; for 2h; Stage #2: With hydrogenchloride In dichloromethane; water	100%
With triethylamine In dichloromethane at 20℃;	100%

: 674-82-8
4-methyleneoxetan-2-one

: 74-93-1
methylthiol

: 108615-97-0
4-Methylsulfanylmethyl-oxetan-2-one

Conditions

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In diethyl ether for 2h; Ambient temperature; Irradiation;	100%

: 674-82-8
4-methyleneoxetan-2-one

: 109-79-5
1-butanethiol

: 72749-29-2
4-(n-Butylthiomethyl)oxetan-2-on

Conditions

Conditions	Yield
In diethyl ether at 0℃; for 0.5h;	100%
With sulfuric acid In diethyl ether for 2h; Ambient temperature;	72%
In diethyl ether at 0 - 5℃;

: 674-82-8
4-methyleneoxetan-2-one

: 111-88-6
Octanethiol

: 108615-99-2
4-Octylsulfanylmethyl-oxetan-2-one

Conditions

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In Petroleum ether at 25℃; for 1h;	100%

: 674-82-8
4-methyleneoxetan-2-one

: 2516-33-8
Cyclopropylmethanol

: 86780-84-9
cyclopropylmethyl 3-oxobutanoate

Conditions

Conditions	Yield
With triethylamine In chloroform for 10h; Ambient temperature;	100%
With sodium hydride at 70 - 80℃; for 2h;	93%
With sodium acetate for 16h; Ambient temperature;

: 674-82-8
4-methyleneoxetan-2-one

: 2216-51-5
(-)-menthol

: 59557-05-0
(L)-menthyl 3-oxobutyrate

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 3h;	100%
With sodium acetate In acetonitrile for 2h; Heating;	96%
With triethylamine In acetone for 2h; Heating;	92%

: 674-82-8
4-methyleneoxetan-2-one

: 4503-58-6
benzyl 2-(2-ethoxy-2-ethoxyethyl)-1-hydrazinecarboxylate

: 98381-06-7
benzyl 2-acetoacetyl-2-(ethoxycarbonylmethyl)hydrazine-1-carboxylate

Conditions

Conditions	Yield
With triethylamine In benzene for 16h; Heating;	100%
In benzene Yield given;

: 674-82-8
4-methyleneoxetan-2-one

: 4490-81-7
isopropoxyamine hydrochloride

: 133146-80-2
N-Isopropoxy-3-oxo-butyramide

Conditions

Conditions	Yield
With triethylamine In methanol; toluene at 0 - 5℃; for 0.5h;	100%

: 674-82-8
4-methyleneoxetan-2-one

: 65253-04-5
(-)-8-phenylmenthol

: 90358-31-9
(+)-(1R,2S,5R)-8-phenylmenthyl 3-oxobutanoate

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 3h;	100%
With triethylamine In acetone for 3h; Heating;	95%
With sodium acetate In chloroform for 1h; Heating;	85.9%
With sodium acetate In tetrahydrofuran for 2h; Heating;

: 674-82-8
4-methyleneoxetan-2-one

: 116308-40-8
2-<4-(4-benzhydryl-1-piperazinyl)phenyl>ethyl alcohol

: 116308-41-9
2-<4-(4-benzhydryl-1-piperazinyl)phenyl>ethyl acetoacetate

Conditions

Conditions	Yield
With dmap In tetrahydrofuran 1) ice-salt cooling, 30 min, 2) r.t.;	100%

: 674-82-8
4-methyleneoxetan-2-one

: 64-04-0
phenethylamine

: 2044-66-8
3-oxo-N-(2-phenylethyl)butanamide

Conditions

Conditions	Yield
In diethyl ether Reflux;	100%
In diethyl ether for 3h; Heating / reflux;	93%
In methanol at 0℃; Inert atmosphere;	46%
In methanol for 3h; Ambient temperature;
In methanol at 0℃; Inert atmosphere;

: 674-82-8
4-methyleneoxetan-2-one

: 81790-27-4
methyl 3-<(benzyloxy)amino>-2-propionate

: 81790-28-5
3-[Benzyloxy-(3-oxo-butyryl)-amino]-2-(4-benzyloxy-phenyl)-propionic acid methyl ester

Conditions

Conditions	Yield
With dmap; triethylamine In tetrahydrofuran 1.) -78 deg C, 30 min, 2.) 0 deg C, 30 min;	100%

: 674-82-8
4-methyleneoxetan-2-one

: 70491-75-7
(S)-methyl 5,5-dimethyl-1,3-thiazolidine-4-carboxylate

: 153823-10-0
methyl (4S)-5,5-dimethyl-3-(3-oxobutanoyl)thiazolidine-4-carboxylate

Conditions

Conditions	Yield
With triethylamine In dichloromethane for 15h; Heating;	100%

: 674-82-8
4-methyleneoxetan-2-one

: 775-15-5
1-benzyl-3-pyrrolidinol

: 71863-54-2
1-benzyl-3-acetoacetyloxypyrrolidine

Conditions

Conditions	Yield
at 70 - 80℃; for 1h;	100%

: 674-82-8
4-methyleneoxetan-2-one

: 14813-01-5
1-benzyl-3-hydroxypiperidine

: 85387-34-4
1-benzylpiperidin-3-yl acetoacetate

Conditions

Conditions	Yield
With triethylamine In chloroform for 10h; Ambient temperature;	100%

: 674-82-8
4-methyleneoxetan-2-one

: (1R,2R,3R)-3-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-cyclohexanol

: 3-Oxo-butyric acid (1R,2S,3R)-3-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-cyclohexyl ester

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran for 9h; Ambient temperature;	100%

: 674-82-8
4-methyleneoxetan-2-one

: 38552-68-0
3,5-dimethyl-hexa-1,4-dien-3-ol

: 664343-03-7
3-oxo-butyric acid 1,3-dimethyl-1-vinyl-but-2-enyl ester

Conditions

Conditions	Yield
With dmap In diethyl ether at 23℃;	100%

: 674-82-8
4-methyleneoxetan-2-one

: 14742-26-8
[13C]methanol

: [13C]methyl 3-oxobutanoate

Conditions

Conditions	Yield
With triethylamine In dichloromethane for 2h; Heating;	100%

: 674-82-8
4-methyleneoxetan-2-one

: 100-36-7
N,N-diethylethylenediamine

: 590424-03-6
N-(2-(diethylamino)ethyl)-3-oxobutanamide

Conditions

Conditions	Yield
In various solvent(s)	100%
In dichloromethane at 0 - 20℃; for 0.5h;	100%
In tert-butyl methyl ether at 0 - 20℃;	93%

: 674-82-8
4-methyleneoxetan-2-one

: 4335-60-8, 4360-51-4, 4226-59-9
(E)-cinnamylamine

: 3-oxo-N-(3-phenyl-2-propen-1-yl)-butylamide

Conditions

Conditions	Yield
With triethylamine In toluene at 70℃; for 3h;	100%
With triethylamine In toluene

: 674-82-8
4-methyleneoxetan-2-one

: 89639-64-5, 3216-44-2
(E)-3-(thien-2-yl)prop-2-en-1-ol

: (E)-3-thiophen-2-ylprop-2-en-1-yl 3-oxobutanoate

Conditions

Conditions	Yield
With triethylamine In toluene at 70℃; for 1.5h;	100%
With dmap In tetrahydrofuran at 0℃; for 2h; Inert atmosphere;	80%

: 674-82-8
4-methyleneoxetan-2-one

: (E)-3-(4-pyridyl)allyl acetoacetate

Conditions

Conditions	Yield
With triethylamine In toluene at 70℃; for 2h;	100%

: 674-82-8
4-methyleneoxetan-2-one

: 1191252-04-6
C31H39NOSi

: 1191252-05-7
C35H43NO3Si

Conditions

Conditions	Yield
In tetrahydrofuran at 20℃; for 2.5h; Inert atmosphere;	100%

: 674-82-8
4-methyleneoxetan-2-one

: 1517-69-7
(R)-1-phenylethanol

: 123261-65-4
(R)-1-phenylethyl acetoacetate

Conditions

Conditions	Yield
With dmap In tetrahydrofuran at 20℃;	100%

Acetyl ketene Consensus Reports

Reported in EPA TSCA Inventory.

Acetyl ketene Standards and Recommendations

DOT Classification: 3; Label: Flammable Liquid, Poison

Acetyl ketene Specification

The Ketene dimer with CAS registry number of 674-82-8 is also known as 2-Oxetanone, 4-methylene-. The IUPAC name is 4-Methylideneoxetan-2-one. It belongs to product categories of Pharmaceutical Intermediates; Aromatic amine products. Its EINECS registry number is 211-617-1. In addition, the formula is C₄H₄O₂and the molecular weight is 84.07. This chemical is a colorless liquid and should be stored in sealed containers in cool, dry place and away from oxidizing agents, acids, bases and amines.

Physical properties about Ketene dimer are: (1)ACD/LogP: 0.27; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.27; (4)ACD/LogD (pH 7.4): 0.27; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 33.28; (8)ACD/KOC (pH 7.4): 33.28; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Index of Refraction: 1.449; (13)Molar Refractivity: 19.91 cm³; (14)Molar Volume: 74.1 cm³; (15)Surface Tension: 28.5 dyne/cm; (16)Density: 1.13 g/cm³; (17)Flash Point: 97.9 °C; (18)Enthalpy of Vaporization: 36.8 kJ/mol; (19)Boiling Point: 127.4 °C at 760 mmHg; (20)Vapour Pressure: 11.1 mmHg at 25 °C.

Preparation of Ketene dimer: it is prepared by thermal decomposition by acetic acid, acetone, acetic anhydride and acetate. Acetic pyrolysises at 750-780 °C in the presence of triethyl phosphate to get ketene, then polymerizes at 8-10 °C to get the product.

CH₃COOH→CH₂CO→C₄H₄O₂

Uses of Ketene dimer: it is used to produce N-acetoacetyl-N'-cyclohexylsulfamide by reaction with cyclohexyl-sulfamide. The reaction occurs with reagent aq.NaOH at ambient temperature for 2 hours. The yield is about 36%. This chemical is also used as raw materials of fine chemicals, dyes, pharmaceuticals, pesticides, food and feed additives, additives and others.

Ketene dimer is used to produce N-acetoacetyl-N'-cyclohexylsulfamide by reaction with cyclohexyl-sulfamide.

When you are using this chemical, please be cautious about it. As a chemical, it is flammable and harmful by inhalation. There is limited evidence of a carcinogenic effect. During using it, wear suitable protective clothing and gloves. Avoid contact with skin and eyes. What's more, take precautionary measures against static discharges and do not breathe gas/fumes/vapour/spray. After using it, keep it in a cool place and keep away from sources of ignition.

You can still convert the following datas into molecular structure:
1. Canonical SMILES: C=C1CC(=O)O1
2. InChI: InChI=1S/C4H4O2/c1-3-2-4(5)6-3/h1-2H2
3. InChIKey: WASQWSOJHCZDFK-UHFFFAOYSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Source
guinea pig	LC50	inhalation	3gm/m³/2H (3000mg/m³)	"Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 301, 1986.
guinea pig	LDLo	skin	10mL/kg (10mL/kg)	Kodak Company Reports. Vol. 21MAY1971,
mouse	LDLo	oral	800mg/kg (800mg/kg)	Kodak Company Reports. Vol. 21MAY1971,
rabbit	LD50	skin	2830uL/kg (2.83mL/kg)	Toxicology and Applied Pharmacology. Vol. 28, Pg. 313, 1974.
rat	LCLo	inhalation	20000ppm/1H (20000ppm)	Industrial Hygiene Foundation of America, Chemical and Toxicological Series, Bulletin. Vol. 6, Pg. 1, 1967.
rat	LD50	oral	560uL/kg (0.56mL/kg)	Toxicology and Applied Pharmacology. Vol. 28, Pg. 313, 1974.

Product Name

Acetyl ketene

Synthetic route

Acetyl ketene Consensus Reports

Acetyl ketene Standards and Recommendations

Acetyl ketene Specification

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