Product Name

  • Name

    Hexachloroacetone

  • EINECS 204-129-5
  • CAS No. 116-16-5
  • Article Data21
  • CAS DataBase
  • Density 1.843 g/cm3
  • Solubility slightly soluble in water
  • Melting Point -3 °C
  • Formula C3Cl6O
  • Boiling Point 203 °C at 760 mmHg
  • Molecular Weight 264.75
  • Flash Point 76.2 °C
  • Transport Information UN 2661 6.1/PG 3
  • Appearance clear colorless to yellowish liquid
  • Safety 24/25-61
  • Risk Codes 22-51/53
  • Molecular Structure Molecular Structure of 116-16-5 (Hexachloroacetone)
  • Hazard Symbols HarmfulXn, DangerousN
  • Synonyms 2-Propanone,hexachloro- (6CI,7CI);1,1,1,3,3,3-Hexachloro-2-propanone;1,1,1,3,3,3-Hexachloropropanone;Bis(trichloromethyl) ketone;HCA;Hexachloro-2-propanone;Hexachloropropanone;NSC 6852;Perchloroacetone;
  • PSA 17.07000
  • LogP 3.29590

Synthetic route

2,2-bis(trichloromethyl)-5-(p-methoxyphenyl)-1,3,4-oxathiazole
73501-03-8

2,2-bis(trichloromethyl)-5-(p-methoxyphenyl)-1,3,4-oxathiazole

dimethyl acetylenedicarboxylate
762-42-5

dimethyl acetylenedicarboxylate

A

1,1,1,3,3,3-hexachloro-propan-2-one
116-16-5

1,1,1,3,3,3-hexachloro-propan-2-one

B

4-methoxybenzonitrile
874-90-8

4-methoxybenzonitrile

C

dimethyl 3-(p-methoxyphenyl)isothiazole-4,5-dicarboxylate
59291-73-5

dimethyl 3-(p-methoxyphenyl)isothiazole-4,5-dicarboxylate

D

S

S

Conditions
ConditionsYield
In 1,3,5-trimethyl-benzene at 161℃; for 0.8h;A 99%
B 8%
C 88%
D n/a
acetone
67-64-1

acetone

1,1,1,3,3,3-hexachloro-propan-2-one
116-16-5

1,1,1,3,3,3-hexachloro-propan-2-one

Conditions
ConditionsYield
With chlorine; pyrographite at 150 - 160℃; for 7h; Temperature; Flow reactor; Industrial scale;98.4%
pentachloro-2-(trimethylsiloxy)propene
87651-34-1

pentachloro-2-(trimethylsiloxy)propene

A

chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

B

1,1,1,3,3,3-hexachloro-propan-2-one
116-16-5

1,1,1,3,3,3-hexachloro-propan-2-one

Conditions
ConditionsYield
With chlorine at 160℃;A 75%
B 51.8%
2,2-bis(trichloromethyl)-5-(p-methoxyphenyl)-1,3,4-oxathiazole
73501-03-8

2,2-bis(trichloromethyl)-5-(p-methoxyphenyl)-1,3,4-oxathiazole

propynoic acid ethyl ester
623-47-2

propynoic acid ethyl ester

A

1,1,1,3,3,3-hexachloro-propan-2-one
116-16-5

1,1,1,3,3,3-hexachloro-propan-2-one

B

ethyl 3-(p-methoxyphenyl)isothiazole-4-carboxylate
76162-57-7

ethyl 3-(p-methoxyphenyl)isothiazole-4-carboxylate

C

ethyl 3-(p-methoxyphenyl)isothiazole-5-carboxylate
76162-58-8

ethyl 3-(p-methoxyphenyl)isothiazole-5-carboxylate

D

4-methoxybenzonitrile
874-90-8

4-methoxybenzonitrile

E

S

S

Conditions
ConditionsYield
In 1,3,5-trimethyl-benzene at 161℃; for 1h;A n/a
B 47%
C 35%
D 16%
E n/a
acetone
67-64-1

acetone

A

1,1,1,3,3,3-hexachloro-propan-2-one
116-16-5

1,1,1,3,3,3-hexachloro-propan-2-one

B

pentachloroacetone
1768-31-6

pentachloroacetone

Conditions
ConditionsYield
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;
chloroacetone
78-95-5

chloroacetone

1,1,1,3,3,3-hexachloro-propan-2-one
116-16-5

1,1,1,3,3,3-hexachloro-propan-2-one

Conditions
ConditionsYield
With chlorine at 50 - 100℃;
glycerol
56-81-5

glycerol

1,1,1,3,3,3-hexachloro-propan-2-one
116-16-5

1,1,1,3,3,3-hexachloro-propan-2-one

Conditions
ConditionsYield
With iodine; chlorine
citric acid
77-92-9

citric acid

1,1,1,3,3,3-hexachloro-propan-2-one
116-16-5

1,1,1,3,3,3-hexachloro-propan-2-one

Conditions
ConditionsYield
With water; chlorine im Sonnenlicht;
2,2-bis(trichloromethyl)-5-(p-methoxyphenyl)-1,3,4-oxathiazole
73501-03-8

2,2-bis(trichloromethyl)-5-(p-methoxyphenyl)-1,3,4-oxathiazole

A

1,1,1,3,3,3-hexachloro-propan-2-one
116-16-5

1,1,1,3,3,3-hexachloro-propan-2-one

B

4-methoxybenzonitrile
874-90-8

4-methoxybenzonitrile

Conditions
ConditionsYield
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.
chlorine
7782-50-5

chlorine

chloroacetone
78-95-5

chloroacetone

1,1,1,3,3,3-hexachloro-propan-2-one
116-16-5

1,1,1,3,3,3-hexachloro-propan-2-one

Conditions
ConditionsYield
at 50 - 100℃;
water
7732-18-5

water

chlorine
7782-50-5

chlorine

citric acid
77-92-9

citric acid

1,1,1,3,3,3-hexachloro-propan-2-one
116-16-5

1,1,1,3,3,3-hexachloro-propan-2-one

Conditions
ConditionsYield
im Sonnenlicht;
hydrogenchloride
7647-01-0

hydrogenchloride

chlorine
7782-50-5

chlorine

acetic acid
64-19-7

acetic acid

acetone
67-64-1

acetone

A

1,1,1,3,3,3-hexachloro-propan-2-one
116-16-5

1,1,1,3,3,3-hexachloro-propan-2-one

B

pentachloroacetone
1768-31-6

pentachloroacetone

Conditions
ConditionsYield
at 20℃; Zusatz von Natriumacetat bei Siedetemperatur;
chlorine
7782-50-5

chlorine

acetic acid
64-19-7

acetic acid

chloroacetone
78-95-5

chloroacetone

A

1,1,1,3,3,3-hexachloro-propan-2-one
116-16-5

1,1,1,3,3,3-hexachloro-propan-2-one

B

pentachloroacetone
1768-31-6

pentachloroacetone

C

decachloro-hexane-2,5-dione
855912-10-6

decachloro-hexane-2,5-dione

Conditions
ConditionsYield
at 160℃; unter Belichtung;
iodine
7553-56-2

iodine

chlorine
7782-50-5

chlorine

glycerol
56-81-5

glycerol

A

1,1,1,3,3,3-hexachloro-propan-2-one
116-16-5

1,1,1,3,3,3-hexachloro-propan-2-one

B

trichlorolactic acid

trichlorolactic acid

C

glycerol chlorohydrin

glycerol chlorohydrin

D

glycerol dichlorohydrin

glycerol dichlorohydrin

Conditions
ConditionsYield
Produkt5:Oxalsaeure;
1,1-Dichloroacetone
513-88-2

1,1-Dichloroacetone

A

1,1,1,3,3,3-hexachloro-propan-2-one
116-16-5

1,1,1,3,3,3-hexachloro-propan-2-one

B

1,1,1-trichloroacetone
918-00-3

1,1,1-trichloroacetone

C

pentachloroacetone
1768-31-6

pentachloroacetone

Conditions
ConditionsYield
With pyridine; chlorine at 70 - 80℃; for 4h;
1,1,3-trichloroacetone
921-03-9

1,1,3-trichloroacetone

A

1,1,1,3,3,3-hexachloro-propan-2-one
116-16-5

1,1,1,3,3,3-hexachloro-propan-2-one

B

pentachloroacetone
1768-31-6

pentachloroacetone

Conditions
ConditionsYield
With pyridine; chlorine at 70 - 80℃;
1,1,1-trichloroacetone
918-00-3

1,1,1-trichloroacetone

1,1,1,3,3,3-hexachloro-propan-2-one
116-16-5

1,1,1,3,3,3-hexachloro-propan-2-one

Conditions
ConditionsYield
With pyridine; chlorine at 120 - 125℃;
chloroacetone
78-95-5

chloroacetone

A

1,1,1,3,3,3-hexachloro-propan-2-one
116-16-5

1,1,1,3,3,3-hexachloro-propan-2-one

B

1,1,1-trichloroacetone
918-00-3

1,1,1-trichloroacetone

C

pentachloroacetone
1768-31-6

pentachloroacetone

Conditions
ConditionsYield
With pyridine; chlorine at 70 - 80℃; for 7.75h;
1,1,1,3,3,3-hexachloro-propan-2-one
116-16-5

1,1,1,3,3,3-hexachloro-propan-2-one

1,1,1,3,3,3-hexachloro-propan-2-ol
6188-63-2

1,1,1,3,3,3-hexachloro-propan-2-ol

Conditions
ConditionsYield
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
116-16-5

1,1,1,3,3,3-hexachloro-propan-2-one

Triphenylmethylamin
5824-40-8

Triphenylmethylamin

trityl isocyanate
4737-21-7

trityl isocyanate

Conditions
ConditionsYield
With triethylamine In dichloromethane for 2h; Ambient temperature;100%
1,1,1,3,3,3-hexachloro-propan-2-one
116-16-5

1,1,1,3,3,3-hexachloro-propan-2-one

isopropylamine
75-31-0

isopropylamine

A

chloroform
67-66-3

chloroform

B

N-Isopropyl-2,2,2-trichloroacetamide
23144-67-4

N-Isopropyl-2,2,2-trichloroacetamide

Conditions
ConditionsYield
In hexaneA n/a
B 100%
1,1,1,3,3,3-hexachloro-propan-2-one
116-16-5

1,1,1,3,3,3-hexachloro-propan-2-one

N-butylamine
109-73-9

N-butylamine

A

chloroform
67-66-3

chloroform

B

trichloro-acetic acid butylamide
31464-96-7

trichloro-acetic acid butylamide

Conditions
ConditionsYield
In hexaneA n/a
B 100%
1,1,1,3,3,3-hexachloro-propan-2-one
116-16-5

1,1,1,3,3,3-hexachloro-propan-2-one

(1R,9R,12S)-12-Hydroxymethyl-1,5-dimethyl-8-oxa-tricyclo[7.2.1.02,7]dodeca-2(7),4-dien-12-ol

(1R,9R,12S)-12-Hydroxymethyl-1,5-dimethyl-8-oxa-tricyclo[7.2.1.02,7]dodeca-2(7),4-dien-12-ol

C15H18O4

C15H18O4

Conditions
ConditionsYield
With triethylamine In dichloromethane for 1h; Ambient temperature;100%
1,1,1,3,3,3-hexachloro-propan-2-one
116-16-5

1,1,1,3,3,3-hexachloro-propan-2-one

2-amino-5-iodobenzoic acid
5326-47-6

2-amino-5-iodobenzoic acid

5-iodoisatoic anhydride
116027-10-2

5-iodoisatoic anhydride

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane; water at 20℃; for 0.166667h;100%
1,1,1,3,3,3-hexachloro-propan-2-one
116-16-5

1,1,1,3,3,3-hexachloro-propan-2-one

tributyltin methoxide
1067-52-3

tributyltin methoxide

tributyl-trichloromethyl-stannane
5764-62-5

tributyl-trichloromethyl-stannane

Conditions
ConditionsYield
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
116-16-5

1,1,1,3,3,3-hexachloro-propan-2-one

tributyltin methoxide
1067-52-3

tributyltin methoxide

1.1.1.3.3.3-Hexachlor-2-methoxy-2--propan
14630-19-4

1.1.1.3.3.3-Hexachlor-2-methoxy-2--propan

Conditions
ConditionsYield
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
116-16-5

1,1,1,3,3,3-hexachloro-propan-2-one

N-Trimethylstannyldiphenylmethylenamin
34982-42-8

N-Trimethylstannyldiphenylmethylenamin

(C4H9)3SnOC(CCl3)2NC(C6H5)2
34982-57-5

(C4H9)3SnOC(CCl3)2NC(C6H5)2

Conditions
ConditionsYield
100%
100%
1,1,1,3,3,3-hexachloro-propan-2-one
116-16-5

1,1,1,3,3,3-hexachloro-propan-2-one

N-ethyl-N-(3-nitropyridine-2-yl)-1H-pyrrol-1-amine
332379-50-7

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
332379-61-0

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
ConditionsYield
In dichloromethane at 20℃; for 4h;99%
1,1,1,3,3,3-hexachloro-propan-2-one
116-16-5

1,1,1,3,3,3-hexachloro-propan-2-one

2,2,3,3-tetrafluoropropanol
76-37-9

2,2,3,3-tetrafluoropropanol

A

chloroform
67-66-3

chloroform

B

bis(2,2,3,3-tetrafluoropropyl) carbonate
1422-70-4

bis(2,2,3,3-tetrafluoropropyl) carbonate

Conditions
ConditionsYield
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
116-16-5

1,1,1,3,3,3-hexachloro-propan-2-one

2,2,2-trifluoroethanol
75-89-8

2,2,2-trifluoroethanol

A

chloroform
67-66-3

chloroform

B

bis(2,2,2-trifluoroethyl) carbonate
1513-87-7

bis(2,2,2-trifluoroethyl) carbonate

Conditions
ConditionsYield
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
116-16-5

1,1,1,3,3,3-hexachloro-propan-2-one

N-benzyl-2-(phenylethynyl)-4-(trifluoromethyl)aniline

N-benzyl-2-(phenylethynyl)-4-(trifluoromethyl)aniline

benzyl[2-(phenylethynyl)-4-(trifluoromethyl)phenyl]carbamic chloride

benzyl[2-(phenylethynyl)-4-(trifluoromethyl)phenyl]carbamic chloride

Conditions
ConditionsYield
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%
1,1,1,3,3,3-hexachloro-propan-2-one
116-16-5

1,1,1,3,3,3-hexachloro-propan-2-one

trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

3,3,3-Trichloro-2-trichloromethyl-2-trimethylsilanyloxy-propionitrile

3,3,3-Trichloro-2-trichloromethyl-2-trimethylsilanyloxy-propionitrile

Conditions
ConditionsYield
aluminium trichloride at 40 - 50℃; for 1h;98%
1,1,1,3,3,3-hexachloro-propan-2-one
116-16-5

1,1,1,3,3,3-hexachloro-propan-2-one

N-benzyl-5-methyl-2-(phenylethynyl)aniline
1380395-17-4

N-benzyl-5-methyl-2-(phenylethynyl)aniline

benzyl[5-methyl-2-(phenylethynyl)phenyl]carbamic chloride

benzyl[5-methyl-2-(phenylethynyl)phenyl]carbamic chloride

Conditions
ConditionsYield
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
116-16-5

1,1,1,3,3,3-hexachloro-propan-2-one

1-amino-2-propene
107-11-9

1-amino-2-propene

A

chloroform
67-66-3

chloroform

B

2,2,2-trichloro-N-(2-propenyl)acetamide
39089-56-0

2,2,2-trichloro-N-(2-propenyl)acetamide

Conditions
ConditionsYield
In hexane for 0.5h;A n/a
B 97%
1,1,1,3,3,3-hexachloro-propan-2-one
116-16-5

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
694526-76-6

(1R,2'R,1''R)-(4-methoxyphenyl){1-[1'-(1''-phenylethyl)aziridin-2'-yl]-1-[pentyl]methyl}amine

(4S,5R,1'R)-4-chloromethyl-1-(4-methoxyphenyl)-5-phenyl-3-(1'-phenylethyl)imidazolidin-2-one

(4S,5R,1'R)-4-chloromethyl-1-(4-methoxyphenyl)-5-phenyl-3-(1'-phenylethyl)imidazolidin-2-one

Conditions
ConditionsYield
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
116-16-5

1,1,1,3,3,3-hexachloro-propan-2-one

2,2,3,3-tetrafluoropropanol
76-37-9

2,2,3,3-tetrafluoropropanol

bis(2,2,3,3-tetrafluoropropyl) carbonate
1422-70-4

bis(2,2,3,3-tetrafluoropropyl) carbonate

Conditions
ConditionsYield
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
methanol
67-56-1

methanol

1,1,1,3,3,3-hexachloro-propan-2-one
116-16-5

1,1,1,3,3,3-hexachloro-propan-2-one

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

Conditions
ConditionsYield
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
116-16-5

1,1,1,3,3,3-hexachloro-propan-2-one

methyl 3-(benzylamino)-4-(phenylethynyl)benzoate

methyl 3-(benzylamino)-4-(phenylethynyl)benzoate

methyl 3-[benzyl(chlorocarbonyl)amino]-4-(phenylethynyl)benzoate

methyl 3-[benzyl(chlorocarbonyl)amino]-4-(phenylethynyl)benzoate

Conditions
ConditionsYield
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%
potassium cyanide

potassium cyanide

sodium cyanide
773837-37-9

sodium cyanide

1,1,1,3,3,3-hexachloro-propan-2-one
116-16-5

1,1,1,3,3,3-hexachloro-propan-2-one

16-methylene-4-androstene-3,17-dione
80108-48-1

16-methylene-4-androstene-3,17-dione

C22H29NO

C22H29NO

Conditions
ConditionsYield
With potassium carbonate; sodium hydroxide In water; acetone at 36℃; for 22h;96.05%
1,1,1,3,3,3-hexachloro-propan-2-one
116-16-5

1,1,1,3,3,3-hexachloro-propan-2-one

ethanolamine
141-43-5

ethanolamine

A

chloroform
67-66-3

chloroform

B

2,2,2-trichloro-N-(2-hydroxyethyl)acetamide
35234-31-2

2,2,2-trichloro-N-(2-hydroxyethyl)acetamide

Conditions
ConditionsYield
In hexane for 0.5h;A n/a
B 96%
1,1,1,3,3,3-hexachloro-propan-2-one
116-16-5

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
867171-99-1

(1S,2'R,1''R)-(4-methoxyphenyl){1-[1'-(1''-phenylethyl)aziridin-2'-yl]pentyl}amine

(4S,5S,1'R)-5-n-butyl-4-chloromethyl-1-(4-methoxyphenyl)-3-(1'-phenylethyl)imidazolidin-2-one

(4S,5S,1'R)-5-n-butyl-4-chloromethyl-1-(4-methoxyphenyl)-3-(1'-phenylethyl)imidazolidin-2-one

Conditions
ConditionsYield
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
116-16-5

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
694526-75-5

(1R,2'R,1''R)-(4-methoxyphenyl){1-[1'-(1''-phenylethyl)aziridin-2'-yl]pentyl}amine

(4S,5R,1'R)-5-n-butyl-4-chloromethyl-1-(4-methoxyphenyl)-3-(1'-phenylethyl)imidazolidin-2-one

(4S,5R,1'R)-5-n-butyl-4-chloromethyl-1-(4-methoxyphenyl)-3-(1'-phenylethyl)imidazolidin-2-one

Conditions
ConditionsYield
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
116-16-5

1,1,1,3,3,3-hexachloro-propan-2-one

N-benzyl-4-methyl-2-(phenylethynyl)phenylamine
1380395-15-2

N-benzyl-4-methyl-2-(phenylethynyl)phenylamine

benzyl[4-methyl-2-(phenylethynyl)phenyl]carbamic chloride

benzyl[4-methyl-2-(phenylethynyl)phenyl]carbamic chloride

Conditions
ConditionsYield
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
116-16-5

1,1,1,3,3,3-hexachloro-propan-2-one

N-benzyl-2-((4-(trifluoromethyl)phenyl)ethynyl)aniline
1616706-99-0

N-benzyl-2-((4-(trifluoromethyl)phenyl)ethynyl)aniline

ethyl 4-({2-[benzyl(chlorocarbonyl)amino]phenyl}ethynyl)benzoate

ethyl 4-({2-[benzyl(chlorocarbonyl)amino]phenyl}ethynyl)benzoate

Conditions
ConditionsYield
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
773837-37-9

sodium cyanide

1,1,1,3,3,3-hexachloro-propan-2-one
116-16-5

1,1,1,3,3,3-hexachloro-propan-2-one

16-methylene-4-androstene-3,17-dione
80108-48-1

16-methylene-4-androstene-3,17-dione

2-hydroxy-2-methylpropanenitrile
75-86-5

2-hydroxy-2-methylpropanenitrile

C22H29NO

C22H29NO

Conditions
ConditionsYield
With sodium carbonate; sodium hydroxide In ethanol; water at 40℃; for 22h;95.77%
potassium cyanide

potassium cyanide

1,1,1,3,3,3-hexachloro-propan-2-one
116-16-5

1,1,1,3,3,3-hexachloro-propan-2-one

16-methylene-4-androstene-3,17-dione
80108-48-1

16-methylene-4-androstene-3,17-dione

2-hydroxy-2-methylpropanenitrile
75-86-5

2-hydroxy-2-methylpropanenitrile

C22H29NO

C22H29NO

Conditions
ConditionsYield
With potassium carbonate In water; isopropyl alcohol at 32℃; for 22h;95.72%

Hexachloroacetone Consensus Reports

Reported in EPA TSCA Inventory.

Hexachloroacetone Standards and Recommendations

DOT Classification:  6.1; Label: KEEP AWAY FROM FOOD

Hexachloroacetone Specification

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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