13045-13-1

Basic information

• Product Name: 3-Chloro-5-hydroxy-2-pentanone
• Synonyms: 3-Chloro-5-hydroxy-2-pentanone;3-Chloro-4-oxo-1-pentanol
• CAS NO: 13045-13-1
• Molecular Formula: C₅H₉ClO₂
• Molecular Weight: 136.58
• Mol File: 13045-13-1.mol

Chemical Properties

• Boiling Point: 264℃
• Flash Point: 113℃
• Appearance: /
• Density: 1.162
• PKA: 14.52±0.10(Predicted)
• CAS DataBase Reference: 3-Chloro-5-hydroxy-2-pentanone(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Chloro-5-hydroxy-2-pentanone(13045-13-1)
• EPA Substance Registry System: 3-Chloro-5-hydroxy-2-pentanone(13045-13-1)

Safety Data

• Hazardous Substances Data: 13045-13-1(Hazardous Substances Data)

Usage

Uses

3-Chloro-5-Hydroxy-2-pentanone is used to prepare thiothiamine.

Synthetic route

3-acetyl-3-chlorodihydrofuran-2(3H)-one (2986-00-7) → 3-chloro-3-acetylpropanol (13045-13-1)

Conditions	Yield
With acidic ion exchanger; water
With hydrogenchloride In acetic acid Heating;
With hydrogenchloride; water; acetic acid for 18h; Reflux;

3-chloro-5-(3-chloro-2-methyl-tetrahydro-furan-2-yloxy)-pentan-2-one (13045-14-2) → 3-chloro-3-acetylpropanol (13045-13-1)

Conditions	Yield
With water at 60℃;
With water at 60℃;

2-chloro-2-(2-hydroxy-ethyl)-acetoacetic acid ethyl ester → 3-chloro-3-acetylpropanol (13045-13-1)

Conditions	Yield
With sulfuric acid; acetic acid

2-(2-acetoxy-ethyl)-2-chloro-acetoacetic acid ethyl ester (857619-39-7) → 3-chloro-3-acetylpropanol (13045-13-1)

Conditions	Yield
With ethanol; sulfuric acid

4-oxopentyl acetate (5185-97-7) → 3-chloro-3-acetylpropanol (13045-13-1)

Conditions	Yield
With chlorine

4-acetoxy-4-chloro-dihydro-furan-2-one → 3-chloro-3-acetylpropanol (13045-13-1)

Conditions	Yield
With hydrogenchloride

2,3-dichloro-2-methyl-tetrahydro-furan (13045-15-3) + water (7732-18-5) → 3-chloro-3-acetylpropanol (13045-13-1)

hydrogenchloride (7647-01-0) + 3-acetyl-3-chlorodihydrofuran-2(3H)-one (2986-00-7) → 3-chloro-5-(3-chloro-2-methyl-tetrahydro-furan-2-yloxy)-pentan-2-one (13045-14-2) + 3-chloro-3-acetylpropanol (13045-13-1)

2-chloro-2-<2-bromo-ethyl>-acetoacetic acid ethyl ester → 3-chloro-3-acetylpropanol (13045-13-1)

Conditions	Yield
With sulfuric acid; acetic acid

ethanol (64-17-5) + 2-(2-acetoxy-ethyl)-2-chloro-acetoacetic acid ethyl ester (857619-39-7) + 35 percent H2SO4 → 3-chloro-3-acetylpropanol (13045-13-1)

α-chloro-α-acetyl-butyrolactone → 3-chloro-5-(3-chloro-2-methyl-tetrahydro-furan-2-yloxy)-pentan-2-one (13045-14-2) + 3-chloro-3-acetylpropanol (13045-13-1)

Conditions	Yield
With hydrogenchloride
With hydrogenchloride

sulfuryl dichloride (7791-25-5) + 5-Hydroxy-2-pentanone (1071-73-4) → 3-chloro-5-(3-chloro-2-methyl-tetrahydro-furan-2-yloxy)-pentan-2-one (13045-14-2) + 3-chloro-3-acetylpropanol (13045-13-1)

Conditions	Yield
at 0℃;
at 0℃;

5-Hydroxy-2-pentanone (1071-73-4) + water (7732-18-5) + chlorine (7782-50-5) → 3-chloro-5-(3-chloro-2-methyl-tetrahydro-furan-2-yloxy)-pentan-2-one (13045-14-2) + 3-chloro-3-acetylpropanol (13045-13-1)

Conditions	Yield
at 20 - 40℃;
at 20 - 40℃;

pentanol-(5)-one-(2) → 3-chloro-5-(3-chloro-2-methyl-tetrahydro-furan-2-yloxy)-pentan-2-one (13045-14-2) + 3-chloro-3-acetylpropanol (13045-13-1)

Conditions	Yield
With sulfuryl dichloride at 0℃;

3-acetyl-2-oxo-4,5-dihydrofuran (517-23-7) → 3-chloro-3-acetylpropanol (13045-13-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 89 percent / SO2Cl2 2: HCl / acetic acid / Heating View Scheme
Multi-step reaction with 2 steps 1: sulfuryl dichloride / 25 h / -10 - 20 °C / Inert atmosphere 2: hydrogenchloride; water; acetic acid / 18 h / Reflux View Scheme

2-(2-hydroxy-ethyl)-acetoacetic acid ethyl ester (86351-01-1) → 3-chloro-3-acetylpropanol (13045-13-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: SO2Cl2 / 0 - 25 °C 2: glacial acetic acid; H2SO4 View Scheme

carbon disulfide (75-15-0) + 3-chloro-3-acetylpropanol (13045-13-1) + 2-(1,1-dimethylethyl)-benzenamine (6310-21-0) → 3-(2-tert-butylphenyl)-1,3-dihydro-5-(2-hydroxyethyl)-4-methyl-2H-thiazole-2-thione

Conditions	Yield
Stage #1: carbon disulfide; 2-(1,1-dimethylethyl)-benzenamine With sodium hydroxide In dimethyl sulfoxide at 20℃; for 1h; Stage #2: 3-chloro-3-acetylpropanol In 1,4-dioxane; dimethyl sulfoxide at 20℃; for 1h; Stage #3: With hydrogenchloride In ethanol at 20℃; for 2.5h; Further stages.;	49%

1-acetylthiosemicarbazide (2302-88-7) + 3-chloro-3-acetylpropanol (13045-13-1) → acetic acid-{N'-[5-(2-hydroxy-ethyl)-4-methyl-thiazol-2-yl]-hydrazide}

Conditions	Yield
With ethanol

5-(aminomethyl)-2-methylpyrimidin-4-amine (95-02-3) + carbon oxide sulfide (463-58-1) + 3-chloro-3-acetylpropanol (13045-13-1) → 3-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-4-hydroxy-5-(2-hydroxy-ethyl)-4-methyl-thiazolidin-2-one

Conditions	Yield
With potassium hydroxide; ammonium hydroxide

4-Amino-2-methyl-5-thioformamidomethylpyrimidin (31375-20-9) + 3-chloro-3-acetylpropanol (13045-13-1) → Aneurin (70-16-6)

Conditions	Yield
With pyridine hydrochloride

diethyl ether (60-29-7) + 3-chloro-3-acetylpropanol (13045-13-1) + thiocarboxamide (115-08-2) → 5-hydroxyethyl-4-methylthiazole (137-00-8)

3-chloro-3-acetylpropanol (13045-13-1) + ethanol (64-17-5) + thiocarboxamide (115-08-2) → 5-hydroxyethyl-4-methylthiazole (137-00-8)

3-chloro-3-acetylpropanol (13045-13-1) + thiocarboxamide (115-08-2) → 5-hydroxyethyl-4-methylthiazole (137-00-8)

Conditions	Yield
With α-picoline; ethyl acetate
With diethyl ether
With pyridine; ethyl acetate
With ethanol

3-chloro-3-acetylpropanol (13045-13-1) + O-benzoylthiolactamide (4917-74-2) → 2-[2-(1-benzoyloxy-ethyl)-4-methyl-thiazol-5-yl]-ethanol (100956-45-4)

3-chloro-3-acetylpropanol (13045-13-1) + sodium ethanolate (141-52-6) → 5-(3-chloro-2-methyl-tetrahydro-[2]furyloxy)-3-methylsulfanyl-pentan-2-one (105583-24-2) + 5-hydroxy-3-methylsulfanyl-pentan-2-one (99115-98-7)

Conditions	Yield
With ethanol; hydrogen sulfide Behandeln des Reaktionsgemisches mit Diazomethan in Aether;

3-chloro-3-acetylpropanol (13045-13-1) + ammonium dithiocarbamate (513-74-6) → 5-(2-hydroxy-ethyl)-4-methyl-3H-thiazole-2-thione (1124-01-2)

Conditions	Yield
With water

3-chloro-3-acetylpropanol (13045-13-1) + ammonium dithiocarbamate (513-74-6) → 4-hydroxy-5-(2-hydroxy-ethyl)-4-methyl-thiazolidine-2-thione (408340-34-1)

Conditions	Yield
With water

3-chloro-3-acetylpropanol (13045-13-1) → 2,3-dichloro-2-methyl-tetrahydro-furan (13045-15-3)

Conditions	Yield
With hydrogenchloride

3-chloro-3-acetylpropanol (13045-13-1) → 3-chloro-5-(3-chloro-2-methyl-tetrahydro-furan-2-yloxy)-pentan-2-one (13045-14-2)

Conditions	Yield
under 1 Torr; Destillation;
under 1 Torr; Destillation;

3-chloro-3-acetylpropanol (13045-13-1) → 3, 5-dichloro-2-pentanone (58371-98-5) + 3-chloro-3-(2-hydroxy-ethyl)-pentane-2,4-dione

Conditions	Yield
With acetyl chloride zuletzt bei 100grad;

3-chloro-3-acetylpropanol (13045-13-1) + acetic anhydride (108-24-7) → 3-chloro-3-(2-hydroxy-ethyl)-pentane-2,4-dione

3-chloro-3-acetylpropanol (13045-13-1) + acetic anhydride (108-24-7) → 5-Acetoxy-3-chloropentan-2-one (13051-49-5)

3-chloro-3-acetylpropanol (13045-13-1) + formamide (77287-34-4, 77287-35-5, 60100-09-6) → 5-hydroxyethyl-4-methylthiazole (137-00-8)

Conditions	Yield
With tetraphosphorus decasulfide; toluene
With tetraphosphorus decasulfide; toluene

3-chloro-3-acetylpropanol (13045-13-1) + acetyl chloride (75-36-5) → 3, 5-dichloro-2-pentanone (58371-98-5) + 3-chloro-3-(2-hydroxy-ethyl)-pentane-2,4-dione

3-chloro-3-acetylpropanol (13045-13-1) + acetyl chloride (75-36-5) → 3-chloro-3-(2-hydroxy-ethyl)-pentane-2,4-dione

3-chloro-3-acetylpropanol (13045-13-1) + acetyl chloride (75-36-5) → 5-Acetoxy-3-chloropentan-2-one (13051-49-5)

Conditions	Yield
With pyridine at 0℃;

3-chloro-3-acetylpropanol (13045-13-1) + thiourea (17356-08-0) → 2-amino-5-(2-hydroxyethyl)-4-methylthiazole (1820-94-6)

3-chloro-3-acetylpropanol (13045-13-1) + dithiooxamide (79-40-3) → 2,2'-(4,4'-dimethyl-[2,2']bithiazolyl-5,5'-diyl)-bis-ethanol (553-22-0)

4-methylphenylglyoxal (1075-47-4) + 5-(aminomethyl)-2-methylpyrimidin-4-amine (95-02-3) + 3-chloro-3-acetylpropanol (13045-13-1) → [3-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-3a-methyl-hexahydro-furo[2,3-d]thiazol-2-yl]-p-tolyl-methanone (16019-01-5)

Conditions	Yield
(i) aq. NaOH, H2S, (ii) /BRN= 126861/, (iii) /BRN= 1099518/, EtOH; Multistep reaction;

4-methylphenylglyoxal (1075-47-4) + 5-(aminomethyl)-2-methylpyrimidin-4-amine (95-02-3) + 3-chloro-3-acetylpropanol (13045-13-1) → [9-(2-hydroxy-ethyl)-2,9a-dimethyl-5,9,9a,10-tetrahydro-pyrimido[4,5-d]thiazolo[3,4-a]pyrimidin-7-yl]-p-tolyl-methanone (16019-02-6) + [3-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-3a-methyl-hexahydro-furo[2,3-d]thiazol-2-yl]-p-tolyl-methanone (16019-01-5)

Conditions	Yield
(i) aq. NaOH, H2S, (ii) /BRN= 126861/, (iii) /BRN= 1099518/, EtOH; Multistep reaction;

4-bromophenylglyoxal (5195-29-9) + 5-(aminomethyl)-2-methylpyrimidin-4-amine (95-02-3) + 3-chloro-3-acetylpropanol (13045-13-1) → (4-bromo-phenyl)-[9-(2-hydroxy-ethyl)-2,9a-dimethyl-5,9,9a,10-tetrahydro-pyrimido[4,5-d]thiazolo[3,4-a]pyrimidin-7-yl]-methanone (16019-00-4) + [3-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-3a-methyl-hexahydro-furo[2,3-d]thiazol-2-yl]-(4-bromo-phenyl)-methanone (16018-99-8)

Conditions	Yield
(i) aq. NaOH, EtOH, (ii) /BRN= 126861/, (iii) /BRN= 1100018/, EtOH; Multistep reaction;
(i) aq. NaOH, H2S, (ii) /BRN= 126861/, (iii) /BRN= 1100018/, EtOH; Multistep reaction;

5-(aminomethyl)-2-methylpyrimidin-4-amine (95-02-3) + 3-chloro-3-acetylpropanol (13045-13-1) + phenylglyoxal hydrate (1074-12-0) → [9-(2-hydroxy-ethyl)-2,9a-dimethyl-5,9,9a,10-tetrahydro-pyrimido[4,5-d]thiazolo[3,4-a]pyrimidin-7-yl]-phenyl-methanone (16018-98-7) + [3-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-3a-methyl-hexahydro-furo[2,3-d]thiazol-2-yl]-phenyl-methanone (24912-08-1)

Conditions	Yield
(i) aq. NaOH, H2S, EtOH, (ii) /BRN= 126861/, (iii) /BRN= 1854721/; Multistep reaction;

Upstream product

• 2986-00-7 3-acetyl-3-chlorodihydrofuran-2(3H)-one 
• 13045-14-2 3-chloro-5-(3-chloro-2-methyl-tetrahydro-furan-2-yloxy)-pentan-2-one 
• 857619-39-7 2-(2-acetoxy-ethyl)-2-chloro-acetoacetic acid ethyl ester 
• 5185-97-7 4-oxopentyl acetate 
• 13045-15-3 2,3-dichloro-2-methyl-tetrahydro-furan 
• 7732-18-5 water 
• 7647-01-0 hydrogenchloride 
• 64-17-5 ethanol 
• 7791-25-5 sulfuryl dichloride 
• 1071-73-4 5-Hydroxy-2-pentanone 
• 7782-50-5 chlorine 
• 517-23-7 3-acetyl-2-oxo-4,5-dihydrofuran 
• 86351-01-1 2-(2-hydroxy-ethyl)-acetoacetic acid ethyl ester 
• 135366-64-2 α-acetyl-α-hydroxy-γ-butyrolactone 

Downstream Products

• 137-00-8 5-hydroxyethyl-4-methylthiazole 
• 100956-45-4 2-[2-(1-benzoyloxy-ethyl)-4-methyl-thiazol-5-yl]-ethanol 
• 1124-01-2 5-(2-hydroxy-ethyl)-4-methyl-3H-thiazole-2-thione 
• 58371-98-5 3, 5-dichloro-2-pentanone 
• 13051-49-5 5-Acetoxy-3-chloropentan-2-one 
• 1820-94-6 2-amino-5-(2-hydroxyethyl)-4-methylthiazole 
• 16019-01-5 [3-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-3a-methyl-hexahydro-furo[2,3-d]thiazol-2-yl]-p-tolyl-methanone 
• 16019-02-6 [9-(2-hydroxy-ethyl)-2,9a-dimethyl-5,9,9a,10-tetrahydro-pyrimido[4,5-d]thiazolo[3,4-a]pyrimidin-7-yl]-p-tolyl-methanone 
• 16019-00-4 (4-bromo-phenyl)-[9-(2-hydroxy-ethyl)-2,9a-dimethyl-5,9,9a,10-tetrahydro-pyrimido[4,5-d]thiazolo[3,4-a]pyrimidin-7-yl]-methanone 
• 16018-99-8 [3-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-3a-methyl-hexahydro-furo[2,3-d]thiazol-2-yl]-(4-bromo-phenyl)-methanone 
• 16018-98-7 [9-(2-hydroxy-ethyl)-2,9a-dimethyl-5,9,9a,10-tetrahydro-pyrimido[4,5-d]thiazolo[3,4-a]pyrimidin-7-yl]-phenyl-methanone 
• 24912-08-1 [3-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-3a-methyl-hexahydro-furo[2,3-d]thiazol-2-yl]-phenyl-methanone 
• 27350-86-3 (4-chloro-phenyl)-[3-(2-methyl-6-oxo-1,6-dihydro-pyrimidin-5-ylmethyl)-3a-methyl-hexahydro-furo[2,3-d]thiazol-2-yl]-methanone 
• 100126-57-6 3-chloro-5-hydroxy-pentan-2-one-(2,4-dinitro-phenylhydrazone) 

Relevant articles and documents

Synthesis of 3-deazathiamine

An efficient ten-step synthesis of deazathiamine is described. The synthesis starts from commercially available α-acetyl-γ-butyrolactone and proceeds via deamination of the key aminothiophene 6. The Gewald synthesis of thiophenes is shown to give a mixture of isomeric products with the unsymmetric ketone used here and so a modified procedure giving a single isomer is developed.

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The present invention discloses a green synthesis method of vitamin B1 intermediates, in the presence of a catalyst α - acetyl - γ - butyrolactone under aerobic conditions, reacted in a solvent, to form α - hydroxyacetyl - γ - butyrolactone, and then into the reaction system into hydrogen chloride, in turn substitution reaction and water decarboxyl reaction, to generate vitamin B1 intermediates, i.e., 3-chloro-5-hydroxy-2-pentanone, the catalyst comprises copper salt Lewis acid The method of synthesizing 3-chloro-5-hydroxy-2-pentanone of the present invention can be more environmentally friendly, the equipment corrosive is small and has a higher yield, and can be carried out in one pot, the operation is simpler, the production cost is lower, and it is more suitable for industrial applications.

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