2,2-bis(trichloromethyl)-5-(p-methoxyphenyl)-1,3,4-oxathiazole
dimethyl acetylenedicarboxylate
A
1,1,1,3,3,3-hexachloro-propan-2-one
B
4-methoxybenzonitrile
C
dimethyl 3-(p-methoxyphenyl)isothiazole-4,5-dicarboxylate
Conditions | Yield |
---|---|
In 1,3,5-trimethyl-benzene at 161℃; for 0.8h; | A 99% B 8% C 88% D n/a |
Conditions | Yield |
---|---|
With chlorine; pyrographite at 150 - 160℃; for 7h; Temperature; Flow reactor; Industrial scale; | 98.4% |
pentachloro-2-(trimethylsiloxy)propene
A
chloro-trimethyl-silane
B
1,1,1,3,3,3-hexachloro-propan-2-one
Conditions | Yield |
---|---|
With chlorine at 160℃; | A 75% B 51.8% |
2,2-bis(trichloromethyl)-5-(p-methoxyphenyl)-1,3,4-oxathiazole
propynoic acid ethyl ester
A
1,1,1,3,3,3-hexachloro-propan-2-one
B
ethyl 3-(p-methoxyphenyl)isothiazole-4-carboxylate
C
ethyl 3-(p-methoxyphenyl)isothiazole-5-carboxylate
D
4-methoxybenzonitrile
Conditions | Yield |
---|---|
In 1,3,5-trimethyl-benzene at 161℃; for 1h; | A n/a B 47% C 35% D 16% E n/a |
Conditions | Yield |
---|---|
With N-benzyl-N,N,N-triethylammonium chloride; chlorine at 40 - 70℃; | A 8% B 43% |
With chlorine an der Sonne; | |
With acetic acid beim Chlorieren anfangs in Gegenwart von wenig HCl bei Raumtemperatur, spaeter in Gegenwart von Natriumacetat bei Siedetemperatur; |
Conditions | Yield |
---|---|
With chlorine at 50 - 100℃; |
Conditions | Yield |
---|---|
With iodine; chlorine |
Conditions | Yield |
---|---|
With water; chlorine im Sonnenlicht; |
2,2-bis(trichloromethyl)-5-(p-methoxyphenyl)-1,3,4-oxathiazole
A
1,1,1,3,3,3-hexachloro-propan-2-one
B
4-methoxybenzonitrile
Conditions | Yield |
---|---|
In 1,3,5-trimethyl-benzene for 1h; Heating; other oxathiazoles also thermolised, also in the presence of dipolarophiles; | A 99 % Chromat. B 98 % Chromat. |
Conditions | Yield |
---|---|
at 50 - 100℃; |
Conditions | Yield |
---|---|
im Sonnenlicht; |
hydrogenchloride
chlorine
acetic acid
acetone
A
1,1,1,3,3,3-hexachloro-propan-2-one
B
pentachloroacetone
Conditions | Yield |
---|---|
at 20℃; Zusatz von Natriumacetat bei Siedetemperatur; |
chlorine
acetic acid
chloroacetone
A
1,1,1,3,3,3-hexachloro-propan-2-one
B
pentachloroacetone
C
decachloro-hexane-2,5-dione
Conditions | Yield |
---|---|
at 160℃; unter Belichtung; |
Conditions | Yield |
---|---|
Produkt5:Oxalsaeure; |
1,1-Dichloroacetone
A
1,1,1,3,3,3-hexachloro-propan-2-one
B
1,1,1-trichloroacetone
C
pentachloroacetone
Conditions | Yield |
---|---|
With pyridine; chlorine at 70 - 80℃; for 4h; |
1,1,3-trichloroacetone
A
1,1,1,3,3,3-hexachloro-propan-2-one
B
pentachloroacetone
Conditions | Yield |
---|---|
With pyridine; chlorine at 70 - 80℃; |
Conditions | Yield |
---|---|
With pyridine; chlorine at 120 - 125℃; |
chloroacetone
A
1,1,1,3,3,3-hexachloro-propan-2-one
B
1,1,1-trichloroacetone
C
pentachloroacetone
Conditions | Yield |
---|---|
With pyridine; chlorine at 70 - 80℃; for 7.75h; |
Conditions | Yield |
---|---|
With N,N'-hexamethylenebis(1-benzyl-3-carbamoyl-1,4-dihydropyridine) In dichloromethane at 25℃; Rate constant; other reagents, solvents; | 100% |
With N,N'-hexamethylenebis(1-benzyl-3-carbamoyl-1,4-dihydropyridine) In dichloromethane at 25℃; Kinetics; var. of reagent, solvent; | 100% |
With 1,2-dimethyl-1,4-dihydropyridine; zinc(II) iodide In cyclohexane at 20℃; for 24h; | 100% |
1,1,1,3,3,3-hexachloro-propan-2-one
Triphenylmethylamin
trityl isocyanate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane for 2h; Ambient temperature; | 100% |
1,1,1,3,3,3-hexachloro-propan-2-one
isopropylamine
A
chloroform
B
N-Isopropyl-2,2,2-trichloroacetamide
Conditions | Yield |
---|---|
In hexane | A n/a B 100% |
1,1,1,3,3,3-hexachloro-propan-2-one
N-butylamine
A
chloroform
B
trichloro-acetic acid butylamide
Conditions | Yield |
---|---|
In hexane | A n/a B 100% |
1,1,1,3,3,3-hexachloro-propan-2-one
Conditions | Yield |
---|---|
With triethylamine In dichloromethane for 1h; Ambient temperature; | 100% |
1,1,1,3,3,3-hexachloro-propan-2-one
2-amino-5-iodobenzoic acid
5-iodoisatoic anhydride
Conditions | Yield |
---|---|
With hydrogenchloride In 1,4-dioxane; water at 20℃; for 0.166667h; | 100% |
1,1,1,3,3,3-hexachloro-propan-2-one
tributyltin methoxide
tributyl-trichloromethyl-stannane
Conditions | Yield |
---|---|
byproducts: CCl3COOCH3; 1:1.1; 33°C / 7 d and 55°C / 4 h; | 100% |
byproducts: Cl3CCOOCH3; 55°C, 4 h;; | |
byproducts: Cl3CCOOCH3; 55°C, 4 h;; |
1,1,1,3,3,3-hexachloro-propan-2-one
tributyltin methoxide
1.1.1.3.3.3-Hexachlor-2-methoxy-2--propan
Conditions | Yield |
---|---|
In tetrachloromethane 1:1; | 100% |
In neat (no solvent) addn. of tributyltin alkoxide to ketone (1:1 mole ratio) at 33°C; proved by NMR; | 100% |
In neat (no solvent) addn. of tributyltin alkoxide to ketone (1:1 mole ratio) at 33°C; proved by NMR; | 100% |
1,1,1,3,3,3-hexachloro-propan-2-one
N-Trimethylstannyldiphenylmethylenamin
(C4H9)3SnOC(CCl3)2NC(C6H5)2
Conditions | Yield |
---|---|
100% | |
100% |
1,1,1,3,3,3-hexachloro-propan-2-one
N-ethyl-N-(3-nitropyridine-2-yl)-1H-pyrrol-1-amine
N,N'-bis[[N-ethyl-N-(pyrrol-1-yl)]-2-amino-pyridin-3-yl]urea[1,2-b][1,2,5]benzotriazepin-11-one
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 4h; | 99% |
1,1,1,3,3,3-hexachloro-propan-2-one
2,2,3,3-tetrafluoropropanol
A
chloroform
B
bis(2,2,3,3-tetrafluoropropyl) carbonate
Conditions | Yield |
---|---|
With potassium fluoride; zirconium(IV) oxide at 140℃; for 10h; Product distribution / selectivity; pressure tight reactor; | A 99% B 99% |
1,1,1,3,3,3-hexachloro-propan-2-one
2,2,2-trifluoroethanol
A
chloroform
B
bis(2,2,2-trifluoroethyl) carbonate
Conditions | Yield |
---|---|
With potassium fluoride; zirconium(IV) oxide at 140℃; for 10h; pressure tight reactor; | A 99% B 99% |
1,1,1,3,3,3-hexachloro-propan-2-one
Conditions | Yield |
---|---|
Stage #1: 1,1,1,3,3,3-hexachloro-propan-2-one With pyridine In dichloromethane at -78℃; Inert atmosphere; Stage #2: N-benzyl-2-(phenylethynyl)-4-(trifluoromethyl)aniline In dichloromethane at -78 - 20℃; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
aluminium trichloride at 40 - 50℃; for 1h; | 98% |
1,1,1,3,3,3-hexachloro-propan-2-one
N-benzyl-5-methyl-2-(phenylethynyl)aniline
Conditions | Yield |
---|---|
Stage #1: 1,1,1,3,3,3-hexachloro-propan-2-one With pyridine In dichloromethane at -78℃; Inert atmosphere; Stage #2: N-benzyl-5-methyl-2-(phenylethynyl)aniline In dichloromethane at -78 - 20℃; Inert atmosphere; | 98% |
1,1,1,3,3,3-hexachloro-propan-2-one
1-amino-2-propene
A
chloroform
B
2,2,2-trichloro-N-(2-propenyl)acetamide
Conditions | Yield |
---|---|
In hexane for 0.5h; | A n/a B 97% |
1,1,1,3,3,3-hexachloro-propan-2-one
(1R,2'R,1''R)-(4-methoxyphenyl){1-[1'-(1''-phenylethyl)aziridin-2'-yl]-1-[pentyl]methyl}amine
Conditions | Yield |
---|---|
Stage #1: (1R,2'R,1''R)-(4-methoxyphenyl){1-[1'-(1''-phenylethyl)aziridin-2'-yl]-1-[pentyl]methyl}amine With sodium hydride In tetrahydrofuran at -10℃; for 1h; Stage #2: 1,1,1,3,3,3-hexachloro-propan-2-one In tetrahydrofuran at -78℃; for 2h; | 97% |
Stage #1: (1R,2'R,1''R)-(4-methoxyphenyl){1-[1'-(1''-phenylethyl)aziridin-2'-yl]-1-[pentyl]methyl}amine With sodium hydride In tetrahydrofuran at -10℃; for 1h; Stage #2: 1,1,1,3,3,3-hexachloro-propan-2-one In tetrahydrofuran at -10℃; for 2h; | 97% |
1,1,1,3,3,3-hexachloro-propan-2-one
2,2,3,3-tetrafluoropropanol
bis(2,2,3,3-tetrafluoropropyl) carbonate
Conditions | Yield |
---|---|
Stage #1: 2,2,3,3-tetrafluoropropanol With Tetraethylene glycol dimethyl ether; potassium carbonate at 10 - 30℃; Stage #2: 1,1,1,3,3,3-hexachloro-propan-2-one at 30 - 70℃; Reagent/catalyst; | 97% |
With potassium fluoride at 100℃; for 10h; | 100 g |
Conditions | Yield |
---|---|
Stage #1: methanol With Tetraethylene glycol dimethyl ether; potassium carbonate at 10 - 30℃; Stage #2: 1,1,1,3,3,3-hexachloro-propan-2-one at 30 - 75℃; Reagent/catalyst; | 97% |
1,1,1,3,3,3-hexachloro-propan-2-one
Conditions | Yield |
---|---|
Stage #1: 1,1,1,3,3,3-hexachloro-propan-2-one With pyridine In dichloromethane at -78℃; Inert atmosphere; Stage #2: methyl 3-(benzylamino)-4-(phenylethynyl)benzoate In dichloromethane at -78 - 20℃; Inert atmosphere; | 97% |
sodium cyanide
1,1,1,3,3,3-hexachloro-propan-2-one
16-methylene-4-androstene-3,17-dione
Conditions | Yield |
---|---|
With potassium carbonate; sodium hydroxide In water; acetone at 36℃; for 22h; | 96.05% |
1,1,1,3,3,3-hexachloro-propan-2-one
ethanolamine
A
chloroform
B
2,2,2-trichloro-N-(2-hydroxyethyl)acetamide
Conditions | Yield |
---|---|
In hexane for 0.5h; | A n/a B 96% |
1,1,1,3,3,3-hexachloro-propan-2-one
(1S,2'R,1''R)-(4-methoxyphenyl){1-[1'-(1''-phenylethyl)aziridin-2'-yl]pentyl}amine
Conditions | Yield |
---|---|
Stage #1: (1S,2'R,1''R)-(4-methoxyphenyl){1-[1'-(1''-phenylethyl)aziridin-2'-yl]pentyl}amine With sodium hydride In tetrahydrofuran at -10℃; for 1h; Stage #2: 1,1,1,3,3,3-hexachloro-propan-2-one In tetrahydrofuran at -78℃; for 2h; | 96% |
Stage #1: (1S,2'R,1''R)-(4-methoxyphenyl){1-[1'-(1''-phenylethyl)aziridin-2'-yl]pentyl}amine With sodium hydride In tetrahydrofuran at -10℃; for 1h; Stage #2: 1,1,1,3,3,3-hexachloro-propan-2-one In tetrahydrofuran at -10℃; for 2h; | 83% |
1,1,1,3,3,3-hexachloro-propan-2-one
(1R,2'R,1''R)-(4-methoxyphenyl){1-[1'-(1''-phenylethyl)aziridin-2'-yl]pentyl}amine
Conditions | Yield |
---|---|
Stage #1: (1R,2'R,1''R)-(4-methoxyphenyl){1-[1'-(1''-phenylethyl)aziridin-2'-yl]pentyl}amine With sodium hydride In tetrahydrofuran at -10℃; for 1h; Stage #2: 1,1,1,3,3,3-hexachloro-propan-2-one In tetrahydrofuran at -78℃; for 2h; | 96% |
Stage #1: (1R,2'R,1''R)-(4-methoxyphenyl){1-[1'-(1''-phenylethyl)aziridin-2'-yl]pentyl}amine With sodium hydride In tetrahydrofuran at -10℃; for 1h; Stage #2: 1,1,1,3,3,3-hexachloro-propan-2-one In tetrahydrofuran at -10℃; for 2h; | 96% |
1,1,1,3,3,3-hexachloro-propan-2-one
N-benzyl-4-methyl-2-(phenylethynyl)phenylamine
Conditions | Yield |
---|---|
Stage #1: 1,1,1,3,3,3-hexachloro-propan-2-one With pyridine In dichloromethane at -78℃; Inert atmosphere; Stage #2: N-benzyl-4-methyl-2-(phenylethynyl)phenylamine In dichloromethane at -78 - 20℃; Inert atmosphere; | 96% |
1,1,1,3,3,3-hexachloro-propan-2-one
N-benzyl-2-((4-(trifluoromethyl)phenyl)ethynyl)aniline
Conditions | Yield |
---|---|
Stage #1: 1,1,1,3,3,3-hexachloro-propan-2-one With pyridine In dichloromethane at -78℃; Inert atmosphere; Stage #2: N-benzyl-2-((4-(trifluoromethyl)phenyl)ethynyl)aniline In dichloromethane at -78 - 20℃; Inert atmosphere; | 96% |
sodium cyanide
1,1,1,3,3,3-hexachloro-propan-2-one
16-methylene-4-androstene-3,17-dione
2-hydroxy-2-methylpropanenitrile
Conditions | Yield |
---|---|
With sodium carbonate; sodium hydroxide In ethanol; water at 40℃; for 22h; | 95.77% |
1,1,1,3,3,3-hexachloro-propan-2-one
16-methylene-4-androstene-3,17-dione
2-hydroxy-2-methylpropanenitrile
Conditions | Yield |
---|---|
With potassium carbonate In water; isopropyl alcohol at 32℃; for 22h; | 95.72% |
Reported in EPA TSCA Inventory.
DOT Classification: 6.1; Label: KEEP AWAY FROM FOOD
The IUPAC name of Hexachloroacetone is 1,1,1,3,3,3-hexachloropropan-2-one. With the CAS registry number 116-16-5 and EINECS 204-129-5, it is also named as Bis(trichloromethyl) ketone. The product's categories are Pharmaceutical Intermediates; Organics. It is clear colorless to yellowish liquid which is highly toxic. When heated to decomposition it emits toxic fumes of Cl−. So the storage environment should be well-ventilated, low-temperature and dry. Keep Hexachloroacetone separate from raw materials of food.
The other characteristics of this product can be summarized as: (1)ACD/LogP: 8.39; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 8.39; (4)ACD/LogD (pH 7.4): 8.39; (5)#H bond acceptors: 1; (6)#H bond donors: 0; (7)#Freely Rotating Bonds: 0; (8)Polar Surface Area: 17.07 Å2; (9)Index of Refraction: 1.539; (10)Molar Refractivity: 45 cm3; (11)Molar Volume: 143.5 cm3; (12)Polarizability: 17.84×10-24 cm3; (13)Surface Tension: 47.7 dyne/cm; (14)Enthalpy of Vaporization: 43.92 kJ/mol; (15)Vapour Pressure: 0.284 mmHg at 25°C; (16)Exact Mass: 263.805081; (17)MonoIsotopic Mass: 261.808031; (18)Topological Polar Surface Area: 17.1; (19)Heavy Atom Count: 10; (20)Complexity: 124.
Uses of Hexachloroacetone: It is mainly used as a pesticide. For the use of hexachloroacetone in the preparation of a novel insect repellent see Perkow reaction. What's more, it can react with 4-methyl-aniline to get 2,2,2-trichloro-N-p-tolyl-acetamide. This reaction needs solvent CHCl3 by heating. The reaction time is 3 hours. The yield is 78%.
When you are using this chemical, please be cautious about it as the following:
It is not only harmful if swallowed, but also toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. So people should avoid contact with skin and eyes. Avoid release to the environment. Refer to special instructions / safety data sheets.
People can use the following data to convert to the molecule structure.
1. Smiles:C(C(C(Cl)(Cl)Cl)=O)(Cl)(Cl)Cl
2. InChI:InChI=1/C3Cl6O/c4-2(5,6)1(10)3(7,8)9
The following are the toxicity data which has been tested.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
dog | LD50 | oral | 700mg/kg (700mg/kg) | Pesticide Chemicals Official Compendium, Association of the American Pesticide Control Officials, Inc., 1966. Vol. -, Pg. 580, 1966. | |
mouse | LC50 | inhalation | 920mg/m3/2H (920mg/m3) | "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 72, 1982. | |
rabbit | LD50 | skin | 2980mg/kg (2980mg/kg) | "Wirksubstanzen der Pflanzenschutz und Schadlingsbekampfungsmittel," Perkow, W., Berlin, Verlag Paul Parey, 1971-1976Vol. -, Pg. -, 1971/1976. | |
rat | LC50 | inhalation | 360ppm/6H (360ppm) | BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: CHRONIC PULMONARY EDEMA | Toxicology and Applied Pharmacology. Vol. 7, Pg. 592, 1965. |
rat | LD50 | oral | 240mg/kg (240mg/kg) | "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 72, 1982. |
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