813-99-0

Basic information

• Product Name: PENTAERYTHRITOL TRICHLOROHYDRIN
• Synonyms: PENTAERYTHRITOL TRICHLOROHYDRIN;2,2-bis(chloromethyl)-3-chloro-1-propanol;3- CHLORO-2,2-BIS(CHLOROMETHYL)-1-PROPANOL;3-CHLORO-2,2-DICHLOROMETHYLPROPANOL;Pentaerythrityl trichlorohydrin;3-Chloro-2,2-bis(chloromethyl)propan-1-ol;1-Propanol,3-chloro-2,2-bis(chloromethyl)-
• CAS NO: 813-99-0
• Molecular Formula: C₅H₉Cl₃O
• Molecular Weight: 191.48
• Mol File: 813-99-0.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 274.39°C (rough estimate)
• Flash Point: 145.4 °C
• Appearance: /
• Density: 1.4096 (rough estimate)
• Vapor Pressure: 3.38E-05mmHg at 25°C
• Refractive Index: 1.5300 (estimate)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: PENTAERYTHRITOL TRICHLOROHYDRIN(CAS DataBase Reference)
• NIST Chemistry Reference: PENTAERYTHRITOL TRICHLOROHYDRIN(813-99-0)
• EPA Substance Registry System: PENTAERYTHRITOL TRICHLOROHYDRIN(813-99-0)

Safety Data

• Hazardous Substances Data: 813-99-0(Hazardous Substances Data)

Usage

General Description

Pentaerythritol trichlorohydrin is a chemical compound that is used primarily as a crosslinking agent in the production of polymers and resins. It is a versatile building block in the synthesis of various specialty chemicals and products, including coatings, adhesives, and sealants. Pentaerythritol trichlorohydrin is also used as an intermediate in the manufacturing of pharmaceuticals, agrochemicals, and flame retardants. It is known for its high reactivity and ability to form strong chemical bonds, making it a valuable component in a wide range of industrial and commercial applications. However, due to its potential hazards to human health and the environment, proper handling and safety measures are essential when working with this compound.

InChI:InChI=1/C5H9Cl3O/c6-1-5(2-7,3-8)4-9/h9H,1-4H2

Synthetic route

Pentaerythritol (115-77-5) → 3-chloro-(2,2-chloromethyl)propan-1-ol (813-99-0)

Conditions	Yield
With pyridine; thionyl chloride at 65 - 130℃; for 22h;	73%
With pyridine; thionyl chloride	50%
With hydrogenchloride; formic acid; benzene at 160℃;

Pentaerythritol (115-77-5) → 2,2-bis(chloromethyl)-1,3-propanediol (2209-86-1) + 3-chloro-(2,2-chloromethyl)propan-1-ol (813-99-0)

Conditions	Yield
With hydrogenchloride at 185℃;
With pyridine; thionyl chloride anfangs unter Eiskuehlung,dann bei Siedetemperatur;

acetic acid-(3-chloro-2,2-bis-chloromethyl-propyl ester) (13103-49-6) → 3-chloro-(2,2-chloromethyl)propan-1-ol (813-99-0)

Conditions	Yield
With sodium hydroxide
With hydrogenchloride

3-chloro-2,2-bis-chloromethyl-propionic acid methyl ester (856808-46-3) → 3-chloro-(2,2-chloromethyl)propan-1-ol (813-99-0)

Conditions	Yield
With lithium aluminium tetrahydride; diethyl ether

3,3-bis(chloromethyl)oxetane (78-71-7) → 3-chloro-(2,2-chloromethyl)propan-1-ol (813-99-0)

Conditions	Yield
With diethylaluminium chloride

Pentaerythritol (115-77-5) → 2,2-bis(chloromethyl)-1,3-propanediol (2209-86-1) + pentaerythrityl tetrachloride (3228-99-7) + 3-chloro-(2,2-chloromethyl)propan-1-ol (813-99-0)

Conditions	Yield
With pyridine; thionyl chloride for 14h; Heating; Yield given. Yields of byproduct given;

Pentaerythritol (115-77-5) → pentaerythrityl tetrachloride (3228-99-7) + 3-chloro-(2,2-chloromethyl)propan-1-ol (813-99-0)

Conditions	Yield
With pyridine; thionyl chloride at 120 - 130℃; Yield given. Yields of byproduct given;
With pyridine; thionyl chloride at 65 - 95℃;

pyridine (110-86-1) + thionyl chloride (7719-09-7) + Pentaerythritol (115-77-5) → 2,2-bis(chloromethyl)-1,3-propanediol (2209-86-1) + pentaerythrityl tetrachloride (3228-99-7) + 3-chloro-(2,2-chloromethyl)propan-1-ol (813-99-0) + pentaerythritol chlorohydrin

Conditions	Yield
anfangs unter Eiskuehlung, dann bei Siedetemperatur;

3-chloro-(2,2-chloromethyl)propan-1-ol (813-99-0) + allyl bromide (106-95-6) → 3-(3-chloro-2,2-bis-chloromethyl-propoxy)-propene (534576-22-2)

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide at 60℃;	82%

3-chloro-(2,2-chloromethyl)propan-1-ol (813-99-0) → 3,3-bis(chloromethyl)oxetane (78-71-7)

Conditions	Yield
With potassium hydroxide In ethanol for 72h; Heating / reflux;	80%
With potassium hydroxide In ethanol for 0.5h; Reflux;	74%
With potassium hydroxide

2-(2-bromoethoxy)tetrahydropyran (17739-45-6, 59146-56-4) + 3-chloro-(2,2-chloromethyl)propan-1-ol (813-99-0) → 2-[2-(3-chloro-2,2-bis-chloromethyl-propoxy)-ethoxy]-tetrahydro-pyran (528609-00-9)

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide at 60℃; for 2h;	73%

3-chloro-(2,2-chloromethyl)propan-1-ol (813-99-0) + 5H-benzo[b]phosphindole (244-87-1) → 3,3-Bis(5-dibenzophospholylmethyl)oxetan

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran 1.) 23 deg C, 30 min, 2.) reflux, 2 h;	69%

3-chloro-(2,2-chloromethyl)propan-1-ol (813-99-0) + 4-(2-[4-(5,7-dimethoxy-4-oxo-3,4-dihydroquinazolin-2-yl)-2,6-dimethylphenoxy]butyl)-4-oxo-2-acetaminobutyric acid → 3-chloro-2,2-di(chloromethyl)propyl 4-(2-[4-(5,7-dimethoxy-4-oxo-3,4-dihydroquinazolin-2-yl)-2,6-dimethylphenoxy]butyl)-4-oxo-2-acetaminobutyrate

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 24h;	65%

3-chloro-(2,2-chloromethyl)propan-1-ol (813-99-0) + 3-bromo-1-(trimethylsilyl)-1-propyne (38002-45-8) → 3-(3-chloro-2,2-bis-chloromethyl-propoxy)-propyne (534576-24-4)

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide at 70℃;	62%

3-chloro-(2,2-chloromethyl)propan-1-ol (813-99-0) + phenylglyoxal hydrate (1074-12-0) → 2,2-Bis-(3-chloro-2,2-bis-chloromethyl-propoxy)-1-phenyl-ethanone

Conditions	Yield
With sulfuric acid In benzene Heating;	54%

3-chloro-(2,2-chloromethyl)propan-1-ol (813-99-0) → pentaerythrityl tetrachloride (3228-99-7)

Conditions	Yield
With phosphorus pentachloride at 150℃;
With phosphorus trichloride

3-chloro-(2,2-chloromethyl)propan-1-ol (813-99-0) → 1-bromo-3-chloro-2,2-bis-chloromethyl-propane

Conditions	Yield
With phosphorus tribromide at 170℃;

3-chloro-(2,2-chloromethyl)propan-1-ol (813-99-0) → 3-chloro-2,2-bis(chloromethyl)propionic acid-1 (17831-70-8)

Conditions	Yield
With nitric acid
With nitric acid
With nitric acid

3-chloro-(2,2-chloromethyl)propan-1-ol (813-99-0) + acetic anhydride (108-24-7) → acetic acid-(3-chloro-2,2-bis-chloromethyl-propyl ester) (13103-49-6)

Conditions	Yield
With pyridine

3-chloro-(2,2-chloromethyl)propan-1-ol (813-99-0) + benzoyl chloride (98-88-4) → benzoic acid-(3-chloro-2,2-bis-chloromethyl-propyl ester) (70190-44-2)

3-ethoxyprop-1-ene (557-31-3) + 3-chloro-(2,2-chloromethyl)propan-1-ol (813-99-0) → 1-chloro-2,2-bis-chloromethyl-3-(1-chloromethyl-2-ethoxy-ethoxy)-propane (60545-52-0)

Conditions	Yield
With chlorine In chloroform

methylallylether (627-40-7) + 3-chloro-(2,2-chloromethyl)propan-1-ol (813-99-0) → 1-chloro-2,2-bis-chloromethyl-3-(1-chloromethyl-2-methoxy-ethoxy)-propane (60545-51-9)

Conditions	Yield
With chlorine In chloroform

3-chloro-(2,2-chloromethyl)propan-1-ol (813-99-0) → phosphorochloridous acid bis-(3-chloro-2,2-bis-chloromethyl-propyl) ester (22864-51-3)

Conditions	Yield
With phosphorus trichloride

3-chloro-(2,2-chloromethyl)propan-1-ol (813-99-0) → phosphorodichloridous acid 3-chloro-2,2-bis-chloromethyl-propyl ester (22864-50-2)

Conditions	Yield
With phosphorus trichloride

3-chloro-(2,2-chloromethyl)propan-1-ol (813-99-0) → 3-Chlor-2,2-bis-chlormethyl-propylphosphonsaeure-bis-(3-chlor-2,2-bis-chlormethyl-propylester) (22864-52-4)

Conditions	Yield
With phosphorus trichloride

3-chloro-(2,2-chloromethyl)propan-1-ol (813-99-0) + allyl bromide (106-95-6) → 1-(2-bromo-1-chloromethyl-ethoxy)-3-chloro-2,2-bis-chloromethyl-propane (60564-36-5)

Conditions	Yield
With chlorine In chloroform

3-chloro-(2,2-chloromethyl)propan-1-ol (813-99-0) + 3-chloroprop-1-ene (107-05-1) → 1-chloro-3-(2-chloro-1-chloromethyl-ethoxy)-2,2-bis-chloromethyl-propane (60545-50-8)

Conditions	Yield
With chlorine In chloroform

3-chloro-(2,2-chloromethyl)propan-1-ol (813-99-0) + diphenylphosphane (829-85-6) → 3,3-Bis(diphenylphosphinomethyl)oxacyclobuyane (156876-04-9)

Conditions	Yield
With potassium tert-butylate 1.) THF, 0 deg C, 20 min, 2.) THF, a) 23 deg C, 30 min, b) reflux, 30 min; Yield given. Multistep reaction;

Upstream product

• 115-77-5 Pentaerythritol 
• 13103-49-6 acetic acid-(3-chloro-2,2-bis-chloromethyl-propyl ester) 
• 856808-46-3 3-chloro-2,2-bis-chloromethyl-propionic acid methyl ester 
• 110-86-1 pyridine 
• 7719-09-7 thionyl chloride 
• 78-71-7 3,3-bis(chloromethyl)oxetane 

Downstream Products

• 1224-69-7 3,3-bis-phenoxymethyl-oxetane 
• 2831-90-5 α,α,α-tris(hydroxymethyl)acetic acid 
• 137266-98-9 1-(3,5-Bis-trifluoromethyl-phenyl)-3-chloromethyl-azetidine-3-carboxylic acid ethyl ester 
• 137606-13-4 N-(3,5-Bis-trifluoromethyl-phenyl)-3-chloro-2,2-bis-chloromethyl-propionamide 
• 137266-71-8 1-(3,5-Bis-trifluoromethyl-phenyl)-3,3-bis-chloromethyl-azetidin-2-one 
• 137266-99-0 3-Chloromethyl-1-(3,5-dichloro-phenyl)-azetidine-3-carboxylic acid propyl ester 
• 137267-00-6 3-Chloromethyl-1-(3,5-dichloro-phenyl)-azetidine-3-carboxylic acid isopropyl ester 
• 137266-97-8 3-Chloromethyl-1-(3,5-dichloro-phenyl)-azetidine-3-carboxylic acid ethyl ester 
• 137606-12-3 3-Chloro-2,2-bis-chloromethyl-N-(3,5-dichloro-phenyl)-propionamide 
• 137266-70-7 3,3-Bis-chloromethyl-1-(3,5-dichloro-phenyl)-azetidin-2-one 
• 137266-85-4 1-benzyl-3-chloromethylazetidine-3-carboxylic acid ethyl ester 
• 137606-01-0 N-benzyl-3-chloro-2,2-bis(chloromethyl)propanamide 
• 137266-59-2 1-benzyl-3,3-bis(chloromethyl)azetidin-2-one 
• 156876-07-2 Benzoesaeure-2,2,2-tris(diphenylphosphinomethyl)ethylester 

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