918-00-3

Basic information

• Product Name: 1,1,1-TRICHLOROACETONE
• Synonyms: 1,1,1-TCA;1,1,1-TRICHLOROACETONE;1,1,1-TRICHLORO-2-PROPANONE;1,1,1--trichloro-2-propanon;1,1,1-trichloro-propan-2-one;1,1,1-Trichloropropanone;2-Propanone, 1,1,1-trichloro-;alpha,alpha,alpha-Trichloroacetone
• CAS NO: 918-00-3
• Molecular Formula: C₃H₃Cl₃O
• Molecular Weight: 161.41
• EINECS: 213-063-6
• Mol File: 918-00-3.mol
• Article Data: 12

Chemical Properties

• Melting Point: 9-11℃
• Boiling Point: 134°C
• Flash Point: 64°C
• Appearance: /
• Density: 1.43
• Vapor Pressure: 1.45mmHg at 25°C
• Refractive Index: 1.4580 to 1.4630
• CAS DataBase Reference: 1,1,1-TRICHLOROACETONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1,1-TRICHLOROACETONE(918-00-3)
• EPA Substance Registry System: 1,1,1-TRICHLOROACETONE(918-00-3)

Safety Data

• Hazard Codes: T+:Very toxic
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39
• RTECS: UC3839000
• Hazardous Substances Data: 918-00-3(Hazardous Substances Data)

Synthetic route

1,1,1-trichloropropan-2-ol (76-00-6) → 1,1,1-trichloroacetone (918-00-3)

Conditions	Yield
With sodium dichromate; sulfuric acid In acetic acid for 0.166667h; Ambient temperature;	82%
With potassium dichromate; sulfuric acid
With potassium dichromate; sulfuric acid In water

chloroacetone (78-95-5) → 1,1,1-trichloroacetone (918-00-3)

Conditions	Yield
With sodium hydrogencarbonate; sodium chloride In water at 23 - 25℃; Product distribution; current 11 A;	82%
With sodium hydrogencarbonate; sodium chloride In water at 23 - 25℃; electrochemical (current 11 A);	82%
With chlorine; potassium hydroxide In water at 15 - 20℃; for 6.6h; Reagent/catalyst; Temperature;

1,1-Dichloroacetone (513-88-2) → 1,1,1-trichloroacetone (918-00-3)

Conditions	Yield
With sodium hypochlorite	80%
With sodium hydrogencarbonate; sodium chloride Product distribution; electrochemically;	65%
With sodium hydrogencarbonate; sodium chloride In water electrochemical;	65%
With sodium acetate; chlorine; acetic acid; sodium chloride Reagens 4: Wasser;

acetyl-triphenylgermane (6430-25-7) → hexachloroethane (67-72-1) + 1,1,1-trichloroacetone (918-00-3) + chlorotriphenylgermane (1626-24-0) + acetyl chloride (75-36-5)

Conditions	Yield
With tetrachloromethane In tetrachloromethane Irradiation (UV/VIS); Ph3GeCOMe photolyzed in CCl4;	A 53% B 10% C 78% D 74%

potassium 2,2,2-trichloroacetate (16586-14-4) + acetyl chloride (75-36-5) → 1,1,1-trichloroacetone (918-00-3)

Conditions	Yield
With perhydrodibenzo-18-crown-6 In acetonitrile for 0.16h;	40%
With dibenzo-18-crown-6 In acetonitrile for 0.16h; Product distribution; other reagent; reaction without macrocyclic polyether; other reaction time.;	25%

3H,3H-hexachloro-pentane-2,4-dione + furan-2,3,5(4H)-trione pyridine (1:1) → 1,1,1-trichloroacetone (918-00-3) + trichloroacetic acid (76-03-9)

acetone (67-64-1) → 1,1,1-trichloroacetone (918-00-3)

sodium trichloroacetate (650-51-1) + acetyl chloride (75-36-5) → 1,1,1-trichloroacetone (918-00-3)

methyl magnesium iodide (917-64-6) + Trichloroacetyl chloride (76-02-8) → 1,1,1-trichloroacetone (918-00-3)

Conditions	Yield
In diethyl ether

Trichloroacetyl chloride (76-02-8) + diethyl malonate (105-53-3) → 1,1,1-trichloroacetone (918-00-3)

Conditions	Yield
(i) EtOH, benzene, (ii) propanoic acid, H2SO4; Multistep reaction;

tetrachloromethane (56-23-5) + 5,5-dicyclopropyl-2-methoxy-2-methyl-Δ3-1,3,4-oxadiazoline (86310-10-3) → chloroform (67-66-3) + acetic acid methyl ester (79-20-9) + 1,1,1-trichloroacetone (918-00-3) + 1,4-dichloro-1-cyclopropylbut-1-ene (86310-12-5) + 1,1,1,2-tetrachloro-2,2-dicyclopropylethane (86310-11-4) + (Z)-1,4,7-Trichloro-5-trichloromethyl-hept-3-ene (86310-13-6)

Conditions	Yield
Mechanism; Heating;	A 10 % Chromat. B 88 % Chromat. C 3 % Chromat. D 7 % Chromat. E n/a F 26 % Chromat.

tetrachloromethane (56-23-5) + dimethylglyoxal (431-03-8) → 1,1,1-trichloroacetone (918-00-3) + butane-2,3-dione (enol form) (73623-81-1) + acetyl chloride (75-36-5) + acetone (67-64-1)

Conditions	Yield
In various solvent(s) Product distribution; Irradiation;

acetone (67-64-1) → 1,1-Dichloroacetone (513-88-2) + 1,1,1-trichloroacetone (918-00-3)

Conditions	Yield
With chlorine In N,N-dimethyl-formamide at 50℃; for 2h; Product distribution; other chlorination agent;	A 95 % Chromat. B 5 % Chromat.

C4H6Cl3O → methyl radical (2229-07-4) + trichloromethyl radical (3170-80-7) + 1,1,1-trichloroacetone (918-00-3) + acetone (67-64-1)

Conditions	Yield
In tetrachloromethane Rate constant; Heating;

chlorine (7782-50-5) + chloroacetone (78-95-5) → 1,1,3-trichloroacetone (921-03-9) + 1,1,1-trichloroacetone (918-00-3)

Conditions	Yield
at 30 - 40℃;

2.4.4-trimethyl-2-trichloromethyl-1.3-dioxolone-(5) → 1,1,1-trichloroacetone (918-00-3)

Conditions	Yield
With hydrogenchloride; acetic acid Hydrolysis;

1,1-Dichloroacetone (513-88-2) + chlorine (7782-50-5) → 1,1,3-trichloroacetone (921-03-9) + 1,1,1-trichloroacetone (918-00-3)

citraconic acid (498-23-7) + water (7732-18-5) + chlorine (7782-50-5) → β-chloromethacrylic acid (6625-00-9) + 1,1,1-trichloroacetone (918-00-3) + α,β,β-trichloro-isobutyric acid (10027-62-0) + 3-chloro-2-hydroxy-2-methyl-succinic acid

Conditions	Yield
citraconsaeures Natrium reagiert;

methylzinc iodide (18815-73-1) + Trichloroacetyl chloride (76-02-8) → 1,1,1-trichloroacetone (918-00-3) + trichloroacetic acid-<β.β.β-trichloro-tert-butyl ester>

1,1-Dichloroacetone (513-88-2) → 1,1,1,3,3,3-hexachloro-propan-2-one (116-16-5) + 1,1,1-trichloroacetone (918-00-3) + pentachloroacetone (1768-31-6)

Conditions	Yield
With pyridine; chlorine at 70 - 80℃; for 4h;

chloroacetone (78-95-5) → 1,1,1,3,3,3-hexachloro-propan-2-one (116-16-5) + 1,1,1-trichloroacetone (918-00-3) + pentachloroacetone (1768-31-6)

Conditions	Yield
With pyridine; chlorine at 70 - 80℃; for 7.75h;

acetone (67-64-1) → 1,1-Dichloroacetone (513-88-2) + 1,1,3-trichloroacetone (921-03-9) + 1,1,1-trichloroacetone (918-00-3)

Conditions	Yield
With hydrogenchloride; chlorine at 20 - 80℃; for 8.5h;

(2S)-2-(6-methoxy(2-naphthyl))propanoic acid (22204-53-1) → chloral hydrate (302-17-0) + chloroform (67-66-3) + 1,1-Dichloroacetone (513-88-2) + 1,1,1-trichloroacetone (918-00-3)

Conditions	Yield
With chlorine In aq. phosphate buffer pH=7; Kinetics; pH-value; UV-irradiation;

3-phenyl-propionaldehyde (104-53-0) + 1,1,1-trichloroacetone (918-00-3) → 3-chloro-6-phenylhex-3(Z)-en-2-one

Conditions	Yield
With chromium dichloride; hydrogen; magnesium bromide; Pd/C (10percent) In tetrahydrofuran at 20℃; for 0.5h;	99%

1,1,1-trichloroacetone (918-00-3) + benzaldehyde (100-52-7) → (Z)-2-Chloro-1-phenyl-1-buten-3-one (53973-14-1, 148470-37-5, 119856-19-8)

Conditions	Yield
With chromium dichloride; hydrogen; magnesium bromide; Pd/C (10percent) In tetrahydrofuran at 20℃; for 0.5h;	99%

1,1,1-trichloroacetone (918-00-3) + phenylhydrazine (100-63-0) → 1-acetyl-2-phenylhydrazine (114-83-0)

Conditions	Yield
With triethylamine In acetonitrile for 8h; Heating;	98%

1,1,1-trichloroacetone (918-00-3) + ethylenediamine (107-15-3) → N,N'-diacetylethylenediamine (871-78-3)

Conditions	Yield
In hexane at 25℃;	97%

1,1,1-trichloroacetone (918-00-3) + isocyanoacetic acid methyl ester (39687-95-1) → (4R,5R)-5-Methyl-5-trichloromethyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester

Conditions	Yield
With triethylamine; copper(l) chloride In 1,2-dichloro-ethane at 18 - 23℃; for 0.5h;	95%
With triethylamine; copper(l) chloride In 1,2-dichloro-ethane for 0.5h; Ambient temperature;	95%

1,1,1-trichloroacetone (918-00-3) + acrylonitrile (107-13-1) → 2,4,4-Trichloro-5-oxo-hexanenitrile

Conditions	Yield
With copper(l) chloride at 110℃; for 12h;	90%

1,1,1-trichloroacetone (918-00-3) + N-butylamine (109-73-9) → N-butylacetamide (1119-49-9)

Conditions	Yield
In hexane at 25℃;	88%

1,1,1-trichloroacetone (918-00-3) + benzaldehyde (100-52-7) → 3,3-dichloro-4-hydroxy-4-phenyl-butan-2-one

Conditions	Yield
With chromium dichloride; hydrogen; magnesium bromide; Pd/C (10percent) In tetrahydrofuran at 0℃; for 12h;	87%

morpholine (110-91-8) + 1,1,1-trichloroacetone (918-00-3) → 4-acetylmorpholine (1696-20-4)

Conditions	Yield
In hexane at 25℃;	86%

propylamine (107-10-8) + 1,1,1-trichloroacetone (918-00-3) → n-propylacetamide (5331-48-6)

Conditions	Yield
In hexane at 25℃;	85%

1,1,1-trichloroacetone (918-00-3) + N-phenylmethanesulfonamide (1197-22-4) → N-(methylsulfonyl)-N-phenylacetamide (3700-65-0)

Conditions	Yield
With Aliquat 336; sodium carbonate In acetonitrile at 80℃; for 2h;	85%

1,1,1-trichloroacetone (918-00-3) + isopropylamine (75-31-0) → N-isopropylacetamide (1118-69-0)

Conditions	Yield
In hexane at 25℃;	85%

1,1,1-trichloroacetone (918-00-3) + benzylamine (100-46-9) → N-(phenylmethyl)acetamide (588-46-5)

Conditions	Yield
In hexane at 25℃;	85%
With aniline In chloroform compatitive reaction with aniline; reaction condition: 1) 5 - 10 deg C, 30 min; 2) 25 deg C, 1 h;	80%

1,1,1-trichloroacetone (918-00-3) → (R)-1,1,1-trichloropropan-2-ol

Conditions	Yield
With Noyori's catalyst In formic acid; triethylamine at 28℃; for 17h; Reagent/catalyst; Inert atmosphere;	85%

SEC-BUTYLAMINE (33966-50-6) + 1,1,1-trichloroacetone (918-00-3) → N-(2-butyl)ethanamide (1189-05-5)

Conditions	Yield
In hexane at 25℃;	82%

3-phenyl-propionaldehyde (104-53-0) + 1,1,1-trichloroacetone (918-00-3) → 3,3-dichloro-4-hydroxy-6-phenyl-hexan-2-one

Conditions	Yield
With chromium dichloride; hydrogen; magnesium bromide; Pd/C (10percent) In tetrahydrofuran at 0℃; for 12h;	82%

1,1,1-trichloroacetone (918-00-3) → 1,1,1-trichloro-2-sulfanylpropan-2-ol (1082905-88-1)

Conditions	Yield
With hydrogenchloride; hydrogen sulfide In methanol at -50℃;	81%

1,1,1-trichloroacetone (918-00-3) + 1-(2-nitro-4,5-dimethoxyphenyl)-2-aminopropane hydrochloride → N-[2-(4,5-Dimethoxy-2-nitro-phenyl)-1-methyl-ethyl]-acetamide

Conditions	Yield
With triethylamine In acetonitrile at 25℃; for 1h;	80%

1,1,1-trichloroacetone (918-00-3) → methyl-2,2,2-trichloroacetimidate (79894-70-5)

Conditions	Yield
With pyridine; hydroxylamine In ethanol	80%

1,1,1-trichloroacetone (918-00-3) + aniline (62-53-3) → Acetanilid (103-84-4)

Conditions	Yield
With triethylamine In hexane Heating;	80%

1,1,1-trichloroacetone (918-00-3) + p-Nitrobenzoyl-L-(+)-glutamic acid (6758-40-3) + 2,4-diamino-5-nitroso-6-hydroxypyrimidine (2387-48-6) → folate (59-30-3)

Conditions	Yield
Stage #1: p-Nitrobenzoyl-L-(+)-glutamic acid; 2,4-diamino6-hydroxy-5-nitroso pyrimidine With hydrogen In water at 82℃; under 6000.6 Torr; Stage #2: 1,1,1-trichloroacetone With sodium metabisulfite; sodium hydroxide In water at 45℃; pH=4.5; pH-value; Pressure; Temperature;	80%

1,1,1-trichloroacetone (918-00-3) + N-(4-aminobenzoyl)-L-glutamic acid (4271-30-1) + 2,4,5-triamino-6-hydroxypyrimidine sulfate (35011-47-3) → folate (59-30-3)

Conditions	Yield
Stage #1: 1,1,1-trichloroacetone; N-(4-aminobenzoyl)-L-glutamic acid With sodium acetate; sodium sulfite In acetic acid at 43℃; for 0.5h; Stage #2: 2,4,5-triamino-6-hydroxypyrimidine sulfate In acetic acid at 38℃; for 5h;	75.5%

piperidine (110-89-4) + 1,1,1-trichloroacetone (918-00-3) → 1-piperidin-1-yl-ethanone (618-42-8)

Conditions	Yield
In hexane at 25℃;	75%

1,1,1-trichloroacetone (918-00-3) + 1-(2-nitro-4,5-methylenedioxyphenyl)-2-aminopropane hydrochloride → N-[1-Methyl-2-(6-nitro-benzo[1,3]dioxol-5-yl)-ethyl]-acetamide

Conditions	Yield
With triethylamine In acetonitrile at 25℃; for 1h;	75%

1,1,1-trichloroacetone (918-00-3) + (Z)-1-(trimethylsiloxy)-1-decene (51425-58-2) → 2-(2,2,2-trichloro-1-hydroxy-1-methyl-ethyl)-decanal

Conditions	Yield
Stage #1: (Z)-1-(trimethylsiloxy)-1-decene With methyllithium In tetrahydrofuran at 0℃; for 0.5h; Metallation; Stage #2: With tetrabutoxytitanium In tetrahydrofuran at 0℃; for 0.5h; complexation; Stage #3: 1,1,1-trichloroacetone In tetrahydrofuran at 0℃; for 1h; Condensation;	72%

1,1,1-trichloroacetone (918-00-3) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → (E)-3-dimethylamino-1,1,1-trichloro-3-buten-2-one (1010796-56-1)

Conditions	Yield
With boron trifluoride diethyl etherate In toluene at 110℃; for 24h;	68%

Upstream product

• 76-00-6 1,1,1-trichloropropan-2-ol 
• 513-88-2 1,1-Dichloroacetone 
• 67-64-1 acetone 
• 650-51-1 sodium trichloroacetate 
• 75-36-5 acetyl chloride 
• 917-64-6 methyl magnesium iodide 
• 76-02-8 trifluoroacetyl chloride 
• 105-53-3 diethyl malonate 
• 56-23-5 tetrachloromethane 
• 86310-10-3 5,5-dicyclopropyl-2-methoxy-2-methyl-Δ³-1,3,4-oxadiazoline 
• 7782-50-5 chlorine 
• 78-95-5 chloroacetone 
• 6430-25-7 acetyl-triphenylgermane 
• 22204-53-1 (2S)-2-(6-methoxy(2-naphthyl))propanoic acid 

Downstream Products

• 16387-26-1 2-methyl-2-trichloromethyl-oxirane 
• 35898-90-9 (2,2,2-trichloro-1-hydroxy-1-methyl-ethyl)-phosphonic acid dimethyl ester 
• 40806-08-4 2,2-Dichlor-1-methylvinyl-diethylphosphat 
• 60-35-5 acetamide 
• 67-66-3 chloroform 
• 109-60-4 1-Propyl acetate 
• 64-19-7 acetic acid 
• 3700-65-0 N-(methylsulfonyl)-N-phenylacetamide 
• 1118-69-0 N-isopropylacetamide 
• 871-78-3 N,N'-diacetylethylenediamine 
• 103-84-4 Acetanilid 
• 75-44-5 phosgene 
• 124-38-9 carbon dioxide 
• 201230-82-2 carbon monoxide 

Relevant articles and documents

1,1,1-trichloroacetone preparation method

The invention provides a 1,1,1-trichloroacetone preparation method, which comprises the following steps: 1, adding monochloroacetone and an alkaline compound into a large amount of an aqueous solutionwithout other organic solvents; 2, forming an aqueous solution or a turbid liquid from the alkaline compound in water while stirring; 3, introducing chlorine gas while stirring until the solution isclear; and 4, in the whole reaction process, controlling the temperature at 0-25 DEG C. According to the invention, the method is simple in process, convenient to operate, high in yield and convenientfor industrial production, and can effectively control the acetone chlorination position, so that the generation of byproducts such as 1,1,3-trichloroacetone, tetrachloroacetone, pentachloroacetone and the like is reduced, and the purity of the prepared product is high and can reach more than 85% without further purification.

A critical examination of the preparation of polychlorinated acetones

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STUDY OF THE ELECTROCHEMICAL CHLORINATION OF ACETONE

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