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

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

Uses

Used in Polymer and Resin Production:
Pentaerythritol trichlorohydrin is used as a crosslinking agent for enhancing the strength and durability of polymers and resins. Its high reactivity allows it to form strong chemical bonds, improving the overall performance of these materials.
Used in Coatings Industry:
Pentaerythritol trichlorohydrin is used as a key component in the formulation of coatings. It contributes to the development of high-quality coatings with excellent adhesion, durability, and resistance to various environmental factors.
Used in Adhesives and Sealants Industry:
Pentaerythritol trichlorohydrin is used as a vital ingredient in the production of adhesives and sealants. Its ability to form strong chemical bonds ensures the creation of effective bonding and sealing solutions for various applications.
Used in Pharmaceutical Manufacturing:
Pentaerythritol trichlorohydrin is used as an intermediate in the synthesis of various pharmaceuticals. Its versatility in chemical reactions allows for the development of a wide range of medicinal compounds.
Used in Agrochemical Production:
Pentaerythritol trichlorohydrin is utilized as an intermediate in the manufacturing of agrochemicals, such as pesticides and herbicides. Its reactivity and ability to form stable bonds contribute to the effectiveness and longevity of these products.
Used in Flame Retardant Industry:
Pentaerythritol trichlorohydrin is used in the production of flame retardants to enhance the fire resistance of various materials. Its chemical properties allow it to form stable bonds with other compounds, creating effective flame retardant solutions.

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 
• 78-71-7 3,3-bis(chloromethyl)oxetane 
• 110-86-1 pyridine 
• 7719-09-7 thionyl chloride 

Downstream Products

• 78-71-7 3,3-bis(chloromethyl)oxetane 
• 3228-99-7 pentaerythrityl tetrachloride 
• 17831-70-8 3-chloro-2,2-bis(chloromethyl)propionic acid-1 
• 70190-44-2 benzoic acid-(3-chloro-2,2-bis-chloromethyl-propyl ester) 
• 156876-04-9 3,3-Bis(diphenylphosphinomethyl)oxacyclobuyane 
• 534576-23-3 H₂CCHCH₂OCH₂C(CH₂P(C₆H₅)2)3 
• 534576-26-6 (CH₃)3SiCCCH₂OCH₂C(CH₂P(C₆H₅)2)3 
• 528609-01-0 2-{3-diphenylphosphanyl-2,2-bis-[(diphenylphosphanyl)-methyl]-propoxy}-ethanol 
• 156876-05-0 2,2,2-tris-(diphenylphosphinomethyl)ethanol 
• 156876-07-2 Benzoesaeure-2,2,2-tris(diphenylphosphinomethyl)ethylester 
• 137266-59-2 1-benzyl-3,3-bis(chloromethyl)azetidin-2-one 
• 137606-01-0 N-benzyl-3-chloro-2,2-bis(chloromethyl)propanamide 
• 137266-85-4 1-benzyl-3-chloromethylazetidine-3-carboxylic acid ethyl ester 
• 137266-70-7 3,3-Bis-chloromethyl-1-(3,5-dichloro-phenyl)-azetidin-2-one 

Relevant articles and documents

Novel pyrrolopyridine derivatives and its use as HIV inhibitor

The present invention relates to a pyrrolopyridine derivative expressed as chemical formula 1, specifically a compound including a substituent group having an oxatane group in R1, its stereoisomer or racemic body, their pharmaceutically acceptable salts or their solvate, a manufacturing method thereof, and an antivirus composition containing the same as an active ingredient, wherein the compound expressed as chemical formula 1 has excellent selectivity and physiological activity with respect to wild type or resistant HIV-1 and therefore can be used as a remedy for AIDS.

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The synthesis of poly has been performed in four steps.Chlorination of pentaerythritol produced a mixture of halogenated alcohols, which, in an alkaline medium, led to a mixture of hydroxylated and chlorinated oxetanes.Of these, the bis(3-chloromethyl) oxetane (BCMO) was etherified with C6F13C2H4OH via phase-transfer catalysis to yield the mono- and di-substituted fluorinated oxetanes.In a last step, the mono-substituted oxetane was cationically polymerized using BF3*OEt2 as the catalyst, and was characterized by 1H and 13C NMR spectroscopy.Finally, several physical properties have been determined such as the viscosity, glass transition and decomposition temperatures, and surface properties.

A novel rearrangement reaction conversion of 3-(chloromethyl)azetidin-2-ones to azetidine-3-carboxylic acid esters

Transformation of 3-(chloromethyl)azetidin-2-ones to azetidine-3-carboxylic acid esters is described. The readily available 3-(chloromethyl)azetidin-2-ones rearranged in good yields to azetidine-3-carboxylic acid esters on treatment with alkoxides. An alternative ring opening - ring closure procedure is also identified.

Synthesis and Properties of Coronands Incorporating Lariat Sulfide and Sulfoxide Groups

A series of 8-substituted 19-methoxy-17-methyl-3,6,10,13-tetraoxabicyclononodeca-1(19),15,17-trienes has been prepared and their complexations with alkali metal and ammonium cations studied.When the 8-substituent contained sulfide functionality weak complexes formed, but hosts with lariat sulfoxide substituents formed complexes - with greatest specificity for lithium ions.