921-03-9

Basic information

• Product Name: 1,1,3-Trichloroacetone
• Synonyms: 1,1,3-trichloro-2-propanon;1,1,3-TRICHLORO-2-PROPANONE;1,1,3-TRICHLOROACETONE;1,1,3-TCA;1,1,3-TRICHLOROACETONE, WACKER QUALITY;2-Propanone, 1,1,3-trichloro-;1,1,3-TRICHLOROPROPANONE
• CAS NO: 921-03-9
• Molecular Formula: C₃H₃Cl₃O
• Molecular Weight: 161.41
• EINECS: 213-063-6
• Mol File: 921-03-9.mol
• Article Data: 12

Chemical Properties

• Melting Point: 9-11 °C(lit.)
• Boiling Point: 88-90 °C76 mm Hg(lit.)
• Flash Point: 80
• Appearance: colorless liquid
• Density: 1.512 g/mL at 20 °C(lit.)
• Vapor Pressure: 30-350Pa at 20-50℃
• Refractive Index: n20/D 1.491
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility: Chloroform, Methanol
• BRN: 1746647
• CAS DataBase Reference: 1,1,3-Trichloroacetone(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1,3-Trichloroacetone(921-03-9)
• EPA Substance Registry System: 1,1,3-Trichloroacetone(921-03-9)

Safety Data

• Hazard Codes: T+,N
• Statements: 25-26-34-50/53-68-21
• Safety Statements: 26-36/37/39-45-60-61-28
• RIDADR: UN 3390 6.1/PG 1
• WGK Germany: 3
• RTECS: UC3840000
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 921-03-9(Hazardous Substances Data)

Usage

Description

1,1,3-Trichloroacetone is direct-acting mutagens in the Ames/Salmonella assay. It is precursor for the generation of 1,3-dihalo oxyallyl intermediates, which undergo [4 + 3] cycloadditions with a host of 1,3-diene systems.

Uses

Different sources of media describe the Uses of 921-03-9 differently. You can refer to the following data:
1. 1,1,3-Trichloroacetone was used in base-induced solvolyses of [3.2.1]Bicyclic α,α′-dichloro ketones.
2. 1,1,3-Trichloroacetone is a reagent used to synthesize chlorinated 5-hydroxy-4-methyl-2(5H)-furanones and mucochloric acid. In addition, it can also be used to synthesize (+)-Phorbol. Phorbol derivatives are important for biomedical research and capable of stimulating T-cell activation, proliferation and cytokine production.

Safety Profile

Poison by inhalation. Corrosiveand lachrymator. Mutation data reported. Combustibleliquid. When heated to decomposition it emits toxic fumesof Clí.

Synthetic route

acetone (67-64-1) → 1,1,3-trichloroacetone (921-03-9)

Conditions	Yield
Stage #1: acetone With 2-isopropylaniline for 1h; Reflux; Stage #2: With chlorine; sodium hydroxide at 60℃; under 3000.3 Torr; pH=8; Reagent/catalyst; Temperature; pH-value;	85%
Stage #1: acetone With 4,4'-bipyridine; chlorine In chlorobenzene at 20 - 30℃; for 2h; Stage #2: With 7,7',8,8'-tetracyanoquinodimethane In chlorobenzene at 50 - 60℃; for 5h; Reagent/catalyst;	83.2%
With chlorine at 30℃; Temperature;	48.1%
With nickel dichloride at 70℃; bei der Chlorierung;

Chloroiodomethane (593-71-5) + ethyl 1,1-dichloroacetate (535-15-9) → 1,1,3-trichloroacetone (921-03-9)

Conditions	Yield
With methyllithium; lithium bromide In tetrahydrofuran; diethyl ether at -78℃; for 0.333333h;	50%
1) tetrahydrofuran, diethyl ether, -78 deg C, 10 min, 2) water; Yield given. Multistep reaction;

diazomethane (186581-53-3, 908094-01-9) + dichloroacethyl chloride (79-36-7) + diethyl ether (60-29-7) → 1,1,3-trichloroacetone (921-03-9)

Conditions	Yield
at -10℃; bei der Behandlung des Reaktionsprodukts mit aether. HCl;

diazomethane (186581-53-3, 908094-01-9) + dichloroacethyl chloride (79-36-7) → 1,1,3-trichloroacetone (921-03-9)

Conditions	Yield
With diethyl ether Behandeln des Reaktionsgemisches mit aether.HCl bei -10grad;

chloroacetone (78-95-5) → 1,1,3-trichloroacetone (921-03-9)

Conditions	Yield
With chlorine at 30 - 40℃;
With chlorine at 40℃; under 750.075 Torr; for 10h; Product distribution / selectivity;

1-Chloro-2-propanol (127-00-4) → 1,1,3-trichloroacetone (921-03-9)

Conditions	Yield
With chlorine at 100℃; Irradiation.mit UV-Licht;

propylene glycol (57-55-6) → 1,1,3-trichloroacetone (921-03-9)

Conditions	Yield
With chlorine Irradiation;

1,3-Dichloro-2-propanol (96-23-1) → 1,1,3-trichloroacetone (921-03-9) + 1,3-Dichloroacetone (534-07-6)

Conditions	Yield
With ruthenium(IV) oxide; sodium chloride In water; ethyl acetate at 5℃; Product distribution; other organic solvents;	A 1 % Chromat. B 62 % Chromat.

pentachloroacetone (1768-31-6) + (methyloxycarbonylmethyl)triphenylphosphonium bromide (1779-58-4) → 1,1,3-trichloroacetone (921-03-9) + methyl 3-(dichloromethyl)-4,4-dichlorocrotonate (97055-33-9)

Conditions	Yield
With triethylamine Product distribution; Mechanism; multistep reaction: 1.) THF, 24 h, room t., 2.) THF, 24 h reactions with var. chlorinated propanones under var. conditions;

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℃;

acetone (67-64-1) + NiCl2 → 1,1-Dichloroacetone (513-88-2) + 1,1,3-trichloroacetone (921-03-9) + chloroacetone (78-95-5) + 1,3-Dichloroacetone (534-07-6)

Conditions	Yield
at 70℃;

3-bromo-1,1-dichloro-propan-2-one → 1,1,3-trichloroacetone (921-03-9)

Conditions	Yield
With ethanol; mercury dichloride

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

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;

chloroacetone (78-95-5) → 1,1-Dichloroacetone (513-88-2) + 1,1,3-trichloroacetone (921-03-9) + 1,3-Dichloroacetone (534-07-6)

Conditions	Yield
With hydrogenchloride; platinum on carbon In water at 95 - 100℃; for 17h; Product distribution / selectivity;
With toluene-4-sulfonic acid; platinum on carbon In water at 95 - 100℃; for 17h; Product distribution / selectivity;
With toluene-4-sulfonic acid; lithium chloride; platinum on carbon In water at 95 - 100℃; for 17h; Product distribution / selectivity;

chloroacetone (78-95-5) → 1,1-Dichloroacetone (513-88-2) + 1,1,3-trichloroacetone (921-03-9) + 1,3-Dichloroacetone (534-07-6) + acetone (67-64-1)

Conditions	Yield
dihydrogen hexachloroplatinate In water at 95 - 100℃; for 17h; Product distribution / selectivity;
mercury dichloride In water at 95 - 100℃; for 17h; Product distribution / selectivity;
cobalt(II) chloride In water at 95 - 100℃; for 17h; Product distribution / selectivity;

1,3-Dichloroacetone (534-07-6) → 1,1,3-trichloroacetone (921-03-9)

Conditions	Yield
With chlorine; iron at 45 - 55℃; for 3h;	36.96 g

2-aminopyridine (504-29-0) + 1,1,3-trichloroacetone (921-03-9) → 2-(dichloromethyl)-2,3-dihydroimidazo[1,2-a]pyridin-2-ol hydrochloride

Conditions	Yield
In tetrahydrofuran at 20 - 70℃; for 16.5h;	100%

5-chloro-2-pyridylamine (1072-98-6) + 1,1,3-trichloroacetone (921-03-9) → 6-chloro-2-(dichloromethyl)-2,3-dihydroimidazo[1,2-a]pyridin-2-ol hydrochloride

Conditions	Yield
In tetrahydrofuran at 20 - 70℃; for 16.5h;	100%

C15H26O4Si + 1,1,3-trichloroacetone (921-03-9) → C18H30O5Si

Conditions	Yield
Stage #1: C15H26O4Si; 1,1,3-trichloroacetone With 2,2,2-trifluoroethanol; triethylamine Stage #2: With zinc In methanol Further stages.;	98%

2-aminopyridine (504-29-0) + 1,1,3-trichloroacetone (921-03-9) → imidazo[1,2-a]pyridine-2-carbaldehyde (118000-43-4) + 2-dichloromethylimidazo<1,2-a>pyridine (143982-35-8) + 2-diethoxymethylimidazo[1,2-a]pyridine (143982-36-9)

Conditions	Yield
In 1,2-dimethoxyethane for 4h; Ambient temperature;	A 5% B 90% C 5%

1,1,3-trichloroacetone (921-03-9) + 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
With sodium metabisulfite at 20 - 30℃; for 2h; Temperature; Ionic liquid;	83.2%
With sodium metabisulfite; sodium acetate at 45℃; for 3h; Temperature;	46.2%

2-aminopyrimidine (109-12-6) + 1,1,3-trichloroacetone (921-03-9) → C7H7Cl2N3O*ClH

Conditions	Yield
In tetrahydrofuran at 20 - 70℃; for 16.5h;	83%

2-aminopyridine (504-29-0) + 1,1,3-trichloroacetone (921-03-9) → imidazo[1,2-a]pyridine-2-carbaldehyde (118000-43-4)

Conditions	Yield
Stage #1: 2-aminopyridine; 1,1,3-trichloroacetone In tetrahydrofuran at 25℃; for 10h; Chichibabin Amination; Stage #2: With calcium carbonate In water at 100℃; for 1h;	82%

1,1,3-trichloroacetone (921-03-9) + N-(4-aminobenzoyl)-L-glutamic acid (4271-30-1) + 2,4,5-triamino-6-hydroxypyrimidine sulfate (35011-47-3) → (S)-2-(4-(((2-amino-4-hydroxypteridin-6-yl)methyl)amino)benzamido)pentanedioic acid (59-30-3)

Conditions	Yield
With sodium hydroxide at 55℃; for 9h; pH=3;	80%
Stage #1: 1,1,3-trichloroacetone; 2,4,5-triamino-6-hydroxypyrimidine sulfate With sodium metabisulfite In methanol; water for 0.5h; Large scale; Stage #2: N-(4-aminobenzoyl)-L-glutamic acid With sodium hydroxide In methanol; water at 40 - 45℃; for 6h; pH=3 - 3.5; Solvent; Large scale;	69.7%

1,1,3-trichloroacetone (921-03-9) + tert-butyl (furan-3-ylmethoxy)dimethylsilane (89861-06-3) → C14H24O3Si

Conditions	Yield
Stage #1: 1,1,3-trichloroacetone; tert-butyl (furan-3-ylmethoxy)dimethylsilane With sodium In 2,2,2-trifluoroethanol Stage #2: With zinc/copper couple In methanol	76%

1,1,3-trichloroacetone (921-03-9) + potassium ethyl xanthogenate (140-89-6) → C6H8Cl2O2S2

Conditions	Yield
In diethyl ether at -10 - -5℃; Inert atmosphere;	76%

1,1,3-trichloroacetone (921-03-9) + C10H13N3O3S → C13H14ClN3O4S

Conditions	Yield
With sodium acetate for 2h; Hantzsch Thiazole Synthesis; Reflux;	76%

1,1,3-trichloroacetone (921-03-9) + 4,5,6-trimethoxy-9-oxa-1-aza-cyclopenta[a]acenaphthylene (338730-12-4) → 16-aza-10,11,12-trimethoxy-18-oxapentacyclo[7.7.1.12,6.02,8.013,17]octadeca-1(16),7,9(10),11,13(17),14-hexaen-4-one (338730-21-5)

Conditions	Yield
Stage #1: 1,1,3-trichloroacetone; 4,5,6-trimethoxy-9-oxa-1-aza-cyclopenta[a]acenaphthylene With 2,2,2-trifluoroethanol; triethylamine at 20℃; for 72h; Foehlisch cycloaddition; Stage #2: With ammonium chloride; zinc In methanol at 20℃; for 10h; sonication; Further stages.;	73%

1,1,3-trichloroacetone (921-03-9) → 1,1,3,3-tetrachloropropanone (632-21-3) + pentachloroacetone (1768-31-6)

Conditions	Yield
With sulfuryl dichloride; N-benzyl-N,N,N-triethylammonium chloride at 55℃; for 168h;	A 72% B n/a

2-Amino-6-bromopyridine (19798-81-3) + 1,1,3-trichloroacetone (921-03-9) → 5-bromoimidazo[1,2-a]pyridine-2-carbaldehyde (878197-68-3)

Conditions	Yield
Stage #1: 2-Amino-6-bromopyridine; 1,1,3-trichloroacetone In 1,2-dimethoxyethane at 25 - 65℃; Inert atmosphere; Large scale reaction; Stage #2: With hydrogenchloride In 1,2-dimethoxyethane; water at 75℃; Large scale reaction; Stage #3: With sodium hydroxide In 1,2-dimethoxyethane at 10℃; pH=8; Large scale reaction;	72%
In 1,2-dimethoxyethane at 25 - 65℃; for 2 - 4h; Product distribution / selectivity;	72%
Stage #1: 2-Amino-6-bromopyridine; 1,1,3-trichloroacetone In 1,2-dimethoxyethane at 70℃; for 15h; Stage #2: In ethanol for 7h; Heating / reflux; Stage #3: With calcium carbonate In water for 1.5h; Product distribution / selectivity; Heating / reflux;	50%

1,1,3-trichloroacetone (921-03-9) + C5H7BrN2 → 5-bromoimidazo[1,2-a]pyridine-2-carbaldehyde (878197-68-3)

Conditions	Yield
With hydrogenchloride In 1,2-dimethoxyethane; water at 10 - 75℃;	72%

2-aminopyridine (504-29-0) + 1,1,3-trichloroacetone (921-03-9) → 2-dichloromethylimidazo<1,2-a>pyridine (143982-35-8)

Conditions	Yield
Stage #1: 2-aminopyridine; 1,1,3-trichloroacetone In 1,2-dimethoxyethane at 20℃; for 4h; Stage #2: In ethanol for 12h; Heating;	71%
In 1,2-dimethoxyethane; ethanol for 4h; Reflux;	5.2 g

1,1,3-trichloroacetone (921-03-9) + C15H15N3O3S → C18H16ClN3O4S

Conditions	Yield
With sodium acetate for 0.666667h; Hantzsch Thiazole Synthesis; Reflux;	71%

2-aminopyridine-3-carboxylic acid ethyl ester (13362-26-0) + 1,1,3-trichloroacetone (921-03-9) → ethyl 2-(dichloromethyl)imidazo[1,2-a]pyridine-8-carboxylate (1033434-43-3)

Conditions	Yield
In 1,2-dimethoxyethane at 20℃;	70%

2-aminopyridine-3-carboxylic acid ethyl ester (13362-26-0) + ethanol (64-17-5) + 1,1,3-trichloroacetone (921-03-9) → ethyl 2-(dichloromethyl)imidazo[1,2-a]pyridine-8-carboxylate (1033434-43-3) + ethyl 2-(diethoxymethyl)imidazo[1,2-a]pyridine-8-carboxylate (1033434-44-4)

Conditions	Yield
Stage #1: 2-aminopyridine-3-carboxylic acid ethyl ester; 1,1,3-trichloroacetone In 1,2-dimethoxyethane at 20℃; for 76h; Inert atmosphere; Stage #2: ethanol for 18h; Inert atmosphere; Reflux; Stage #3: With sodium hydrogencarbonate In water	A 70% B 4%

1,1,3-trichloroacetone (921-03-9) + 1-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl) ethan-1-one N-ethyl thiosemicarbazone → C14H16ClN3O4S

Conditions	Yield
With sodium acetate for 1h; Hantzsch Thiazole Synthesis; Reflux;	66%

1,1,3-trichloroacetone (921-03-9) + 6-fluoro-pyridin-2-ylamine (1597-32-6) → 2-(dichloromethyl)-5-fluoroimidazo[1,2-a]pyridine (878197-91-2)

Conditions	Yield
In 1,2-dimethoxyethane at 85℃; for 15h;	65%
In 1,2-dimethoxyethane at 85℃; for 15h;	65%
In 1,2-dimethoxyethane at 85℃; for 15h; Product distribution / selectivity;	65%
In 1,2-dimethoxyethane at 85℃; for 15h;	65%
In 1,2-dimethoxyethane at 80℃; for 12h;	63%

1,1,3-trichloroacetone (921-03-9) + potassium O-neopentyl xanthate → C9H14Cl2O2S2

Conditions	Yield
In diethyl ether at -10 - -5℃; Inert atmosphere;	62%

2-Amino-3-bromopyridine (13534-99-1) + 1,1,3-trichloroacetone (921-03-9) → C8H5BrN2O (1194375-12-6)

Conditions	Yield
Stage #1: 2-Amino-3-bromopyridine; 1,1,3-trichloroacetone In 1,2-dimethoxyethane at 40 - 80℃; Stage #2: With N-ethyl-N,N-diisopropylamine In 1,2-dimethoxyethane at 80℃; for 60h; Stage #3: With calcium carbonate In water at 90℃; for 1h;	56%

1,1,3-trichloroacetone (921-03-9) + 4-(furan-3'-yl)butan-1-ol (90812-87-6) → 6-(4-hydroxy-butyl)-8-oxa-bicyclo[3.2.1]oct-6-en-3-one (619297-74-4)

Conditions	Yield
Stage #1: 1,1,3-trichloroacetone; 4-(furan-3'-yl)butan-1-ol With sodium 2,2,2-trifluoroethanolate In 2,2,2-trifluoroethanol at 0 - 20℃; for 72h; Stage #2: With copper(I) bromide; zinc In methanol at 20℃; for 48h;	54%

1,1,3-trichloroacetone (921-03-9) + sodium 2,2,2-trifluoroethanolate (420-87-1) + cyclopenta-1,3-diene (542-92-7) → 2,2-bis(2,2,2-trifluoroethoxy)bicyclo[3.2.1]oct-6-en-3-one

Conditions	Yield
Stage #1: 1,1,3-trichloroacetone; cyclopenta-1,3-diene In 2,2,2-trifluoroethanol at 0 - 20℃; for 1h; Stage #2: sodium 2,2,2-trifluoroethanolate In 2,2,2-trifluoroethanol for 10h; Heating;	53%

3,6-difluoropyridin-2-amine (944799-22-8) + 1,1,3-trichloroacetone (921-03-9) → 2-(dichloromethyl)-5,8-difluoroimidazo[1,2-a]pyridine (944799-23-9)

Conditions	Yield
In 1,4-dioxane at 50 - 100℃; for 120h;	52%

2-Aminopyrazine (5049-61-6) + 1,1,3-trichloroacetone (921-03-9) → 1,1-Dichloro-3-(pyrazin-2-ylamino)-propan-2-one

Conditions	Yield
In 1,2-dimethoxyethane for 3h; Heating;	47%

1,1,3-trichloroacetone (921-03-9) + C20H28O3 → C23H32O4 + C23H32O4

Conditions	Yield
Stage #1: 1,1,3-trichloroacetone; C20H28O3 With triethylamine In 1,1,1,3,3,3-hexafluoroisopropaol at 20℃; for 48h; Cooling with ice; Stage #2: With copper; ammonium chloride; zinc In methanol	A 46% B 47%

Upstream product

• 127-00-4 1-Chloro-2-propanol 
• 78-95-5 chloroacetone 
• 534-07-6 1,3-Dichloroacetone 
• 67-64-1 acetone 
• 513-88-2 1,1-Dichloroacetone 
• 7782-50-5 chlorine 
• 1768-31-6 pentachloroacetone 
• 1779-58-4 (methyloxycarbonylmethyl)triphenylphosphonium bromide 
• 593-71-5 Chloroiodomethane 
• 535-15-9 ethyl 1,1-dichloroacetate 
• 96-23-1 1,3-Dichloro-2-propanol 
• 57-55-6 propylene glycol 
• 186581-53-3 diazomethane 
• 79-36-7 dichloroacethyl chloride 

Downstream Products

• 59-30-3 folic acid 
• 1197040-29-1 phenyl isocyanate 
• 143982-35-8 2-dichloromethylimidazo<1,2-a>pyridine 
• 59-30-3 (S)-2-(4-(((2-amino-4-hydroxypteridin-6-yl)methyl)amino)benzamido)pentanedioic acid 
• 118000-43-4 imidazo[1,2-a]pyridine-2-carbaldehyde 
• 878197-68-3 5-bromoimidazo[1,2-a]pyridine-2-carbaldehyde 
• 59-30-3 folate 
• 1194375-12-6 8-bromoimidazo[1,2-a]pyridine-2-carbaldehyde 
• 878197-67-2 5-fluoroimidazo[1,2-a]pyridine-2-carbaldehyde 
• 878197-91-2 2-(dichloromethyl)-5-fluoroimidazo[1,2-a]pyridine 
• 632-21-3 1,1,3,3-tetrachloropropanone 
• 1768-31-6 pentachloroacetone 
• 116-16-5 1,1,1,3,3,3-hexachloro-propan-2-one 
• 874527-17-0 1-chloro-4-(α,β,β,β'-tetrachloro-isopropyl)-benzene 

Relevant articles and documents

High-selectivity synthetic method for 1,1,3-trichloroacetone

The invention discloses a high-selectivity synthetic method for 1,1,3-trichloroacetone. The high-selectivity synthetic method includes the specific following steps that (1) 2-hydrocarbyl aniline and acetone are reacted to generate imine, chlorine is led for acetone chlorination, and meanwhile the pH of reaction liquid is kept with a sodium hydroxide solution; (2) after the chlorination reaction is completed, the pH value of the reaction liquid is adjusted by adjusting the adding quantity of the sodium hydroxide solution, imine is decomposed accordingly, 1,1,3-ichloroacetone and 2-alkyl aniline are obtained, filtering is carried out, and generated salt is removed; (3) filtered liquid is subjected to pressure reduction fractional distillation, and concentrated liquid after fractional distillation is the high-concentration-and-purity 1,1,3-trichloroacetone. By means of the high-selectivity synthetic method for the 1,1,3-trichloroacetone, the synthetic selectivity of the 1,1,3-trichloroacetone is effectively improved, the yield of a product is further increased, and the quality of the product is further improved; meanwhile, the device requirements are low, the safety factor is high, and the discharging amount of waste liquid is greatly reduced.

Preparing method for 1,1,3-trichloroacetone

The invention relates to a preparing method for 1,1,3-trichloroacetone. The preparing method comprises the following process steps that firstly, acetone and methyl alcohol serve as raw materials, an intermediate product 1,3-dichloroacetone dimethyl carbinol is obtained through chlorine chlorination preparation, a crude 1,1,3-trichloroacetone product is obtained through methyl alcohol stripping and deep chlorination, and a pure product is obtained through rectification. According to an improvement of the preparing mehtod, 1,3-dichloroacetone dimethyl carbinol easy to separate is prepared firstly from acetone, by-products 1,1-dichloroacetone and 1,1,1-trichloroacetone are separated out, then carbonyl is reduced through the method of introducing chlorine, new substances cannot be introduced, the purity of the end product1,1,3-trichloroacetone is high, and the total yield through the three-step reaction is high.