3513-81-3

Basic information

• Product Name: 2-Methylene-1,3-propanediol
• Synonyms: 2-METHYLENE-1,3-PROPANEDIOL;3-HYDROXY-2-HYDROXYMETHYL-1-PROPENE;2-methylene-3-propanediol;2-methylenepropane-1,3-diol;1-（4-pyridinyl) acetone;2-METHYLENE-1,3-PROPANEDIOL,97+%;1,3-Propanediol, 2-methylene-;2-(Hydroxymethyl)-2-propene-1-ol
• CAS NO: 3513-81-3
• Molecular Formula: C₄H₈O₂
• Molecular Weight: 88.11
• EINECS: 222-516-7
• Product Categories: Alcohols;Monomers;Polymer Science
• Mol File: 3513-81-3.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 93-95 °C2 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear colorless to pale yellow/Viscous Liquid
• Density: 1.081 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00867mmHg at 25°C
• Refractive Index: n20/D 1.473(lit.)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 14.14±0.10(Predicted)
• BRN: 1737653
• CAS DataBase Reference: 2-Methylene-1,3-propanediol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methylene-1,3-propanediol(3513-81-3)
• EPA Substance Registry System: 2-Methylene-1,3-propanediol(3513-81-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 3513-81-3(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to pale yellow viscous liquid

InChI:InChI=1/C4H8O2/c1-4(2-5)3-6/h5-6H,1-3H2

Synthetic route

1,3-diacetoxy-2-methylenepropane (3775-29-9) → 2-(Hydroxymethyl)allyl alcohol (3513-81-3)

Conditions	Yield
With pyridine; dmap In dichloromethane at 0 - 20℃; for 0.5h;	98%
With potassium hydroxide In methanol at 60℃; under 750.075 Torr; Reagent/catalyst; Inert atmosphere;	97.5%
With hydrogenchloride In ethanol Heating;	65%
With methanol; potassium carbonate at 20℃;

2-methylene-1,3-propane-[bis-(tert-butyl)carbonate] (620161-75-3) → 2-(Hydroxymethyl)allyl alcohol (3513-81-3)

Conditions	Yield
With dmap In tetrahydrofuran Heating;	98%

2-(bromomethyl)-2-(hydroxymethyl)propane-1,3-diol (19184-65-7) → 3,3-bis(hydroxymethyl)oxetane (2754-18-9) + 2-(Hydroxymethyl)allyl alcohol (3513-81-3)

Conditions	Yield
With base	A 70% B 17%
With potassium hydroxide

pentaerythrityl mononitrate (1607-00-7) → 3,3-bis(hydroxymethyl)oxetane (2754-18-9) + 2-(Hydroxymethyl)allyl alcohol (3513-81-3)

Conditions	Yield
With potassium hydroxide In ethanol for 2h; Heating;	A 69% B 8.5%

2-chloromethyl-3-chloroprop-1-ene (1871-57-4) → 2-(Hydroxymethyl)allyl alcohol (3513-81-3)

Conditions	Yield
With water; calcium carbonate for 120h; Heating;	65%
With calcium carbonate
With potassium hydroxide In water for 40h; Heating;
With potassium carbonate In water

2,2-di-hydroxymethylnorborn-5-ene (6707-12-6) → 2-(Hydroxymethyl)allyl alcohol (3513-81-3)

Conditions	Yield
With silicon oil at 235 - 237℃; for 4h;	54%

2-(bromomethyl)-2-(hydroxymethyl)propane-1,3-diol (19184-65-7) → 2-(Hydroxymethyl)allyl alcohol (3513-81-3)

Conditions	Yield
With water; silver(l) oxide
With barium dihydroxide; water

2-hydroxymethyl-propenal (40364-84-9) → 2-(Hydroxymethyl)allyl alcohol (3513-81-3)

Conditions	Yield
With sodium tetrahydroborate In tetrahydrofuran; methanol at 0℃; for 3h; Yield given;
With sodium tetrahydroborate In tetrahydrofuran; methanol Yield given;

2,2-Dimethyl-propionic acid 2-(2,2-dimethyl-propionyloxymethyl)-allyl ester (113859-64-6) → 2-(Hydroxymethyl)allyl alcohol (3513-81-3)

Conditions	Yield
With sodium methylate In methanol for 20h; Ambient temperature; Yield given;

2-isopropoxy-4-methylene-[1,2]oxaborolane → 2-(Hydroxymethyl)allyl alcohol (3513-81-3)

Conditions	Yield
With sodium hydroxide; dihydrogen peroxide In water at 20℃; for 2h; Oxidation;

2-(bromomethyl)-2-(hydroxymethyl)propane-1,3-diol (19184-65-7) + water (7732-18-5) + barium oxide → 2-(Hydroxymethyl)allyl alcohol (3513-81-3)

2-(bromomethyl)-2-(hydroxymethyl)propane-1,3-diol (19184-65-7) + water (7732-18-5) + silver oxide → 2-(Hydroxymethyl)allyl alcohol (3513-81-3)

2-(bromomethyl)-2-(hydroxymethyl)propane-1,3-diol (19184-65-7) + ethanolic KOH-solution → 3,3-bis(hydroxymethyl)oxetane (2754-18-9) + 2-(Hydroxymethyl)allyl alcohol (3513-81-3)

Methyltriphenylphosphonium bromide (1779-49-3) + 2,2,-dimethyl-1,3-dioxan-5-one (74181-34-3) → 2-(Hydroxymethyl)allyl alcohol (3513-81-3)

Conditions	Yield
Stage #1: Methyltriphenylphosphonium bromide; 2,2,-dimethyl-1,3-dioxan-5-one With potassium tert-butylate Inert atmosphere; Stage #2: With toluene-4-sulfonic acid In acetone Inert atmosphere;

2-(Hydroxymethyl)allyl alcohol (3513-81-3) + benzyl bromide (100-39-0) → 2-methylenepropane-1,3-bisbenzyl ether (27441-79-8)

Conditions	Yield
With tetra-(n-butyl)ammonium iodide; sodium hydride In N,N-dimethyl-formamide at 40℃;	100%
With sodium hydride In N,N-dimethyl-formamide at 0℃;

2-(Hydroxymethyl)allyl alcohol (3513-81-3) + methyl chloroformate (79-22-1) → 2-{[(methoxycarbonyl)oxy]methyl}allyl methyl carbonate (130667-36-6)

Conditions	Yield
With pyridine In dichloromethane at 0 - 20℃;	100%
With pyridine; dmap In dichloromethane at 20℃; for 24h;	98%

2-(Hydroxymethyl)allyl alcohol (3513-81-3) + tert-butylchlorodiphenylsilane (58479-61-1) → 2-<(tert-butyldiphenylsilyloxy)methyl>prop-2-en-1-ol (177606-51-8)

Conditions	Yield
Stage #1: 2-(Hydroxymethyl)allyl alcohol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 1h; Inert atmosphere; Stage #2: tert-butylchlorodiphenylsilane In tetrahydrofuran; mineral oil at 0 - 20℃; Inert atmosphere; Stage #3: With water In tetrahydrofuran; mineral oil at 0℃; Inert atmosphere;	100%
Stage #1: 2-(Hydroxymethyl)allyl alcohol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 1h; Inert atmosphere; Stage #2: tert-butylchlorodiphenylsilane In tetrahydrofuran; mineral oil at 20℃;	99%
Stage #1: 2-(Hydroxymethyl)allyl alcohol With sodium hydride In tetrahydrofuran at 20℃; for 1.16667h; Stage #2: tert-butylchlorodiphenylsilane In tetrahydrofuran at 20℃; for 16h;	98%

2-(Hydroxymethyl)allyl alcohol (3513-81-3) + di-tert-butyl dicarbonate (24424-99-5) → 2-methylene-1,3-propane-[bis-(tert-butyl)carbonate] (620161-75-3)

Conditions	Yield
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In dichloromethane; water at 15 - 30℃; for 7 - 8h;	100%
tetra(n-butyl)ammonium hydrogensulfate In dichloromethane; water at 15 - 30℃; for 10.5 - 13h;	100%
With dmap Heating;	89%

vinyl acetate (108-05-4) + 2-(Hydroxymethyl)allyl alcohol (3513-81-3) → 1,3-diacetoxy-2-methylenepropane (3775-29-9)

Conditions	Yield
With Candida antarctica lipase B In dichloromethane at 20℃; for 24h; Enzymatic reaction;	100%

2-(Hydroxymethyl)allyl alcohol (3513-81-3) + acetic anhydride (108-24-7) → 1,3-diacetoxy-2-methylenepropane (3775-29-9)

Conditions	Yield
With pyridine; dmap In dichloromethane at 0℃; for 0.5h;	98%
With pyridine; dmap In dichloromethane at 20℃; for 24h;	95%
With pyridine

3,4,5,6-Tetrahydrophthalic anhydride (2426-02-0) + 2-(Hydroxymethyl)allyl alcohol (3513-81-3) → 3a-hydroxymethyl-1-oxo-hexahydro-2-oxa-cyclopenta<1,4>cyclobuta<1,2>benzene-4a-carboxylic acid

Conditions	Yield
In acetonitrile for 4h; Irradiation;	97%

2-(Hydroxymethyl)allyl alcohol (3513-81-3) → 2-methyl-1.3-propanediol (2163-42-0)

Conditions	Yield
With hydrogen at 60℃; under 15001.5 Torr;	97%

2-(Hydroxymethyl)allyl alcohol (3513-81-3) → (2-hydroxymethyl-oxiranyl)-methanol (340184-54-5)

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 4h;	96%

2-(Hydroxymethyl)allyl alcohol (3513-81-3) + benzaldehyde (100-52-7) → (+/-)-3-methylene-1,5-diphenylpentanediol (71370-00-8)

Conditions	Yield
With tin(ll) chloride In various solvent(s) at 50℃; for 15h;	95%

2-(Hydroxymethyl)allyl alcohol (3513-81-3) + N-phenylbenzohydrazonoyl chloride (15424-14-3) → (3-hydroxymethyl-2,5-diphenyl-3,4-dihydro-2H-pyrazol-3-yl)methanol

Conditions	Yield
With triethylamine In dichloromethane; water at 20℃; for 10h; Reagent/catalyst; Huisgen Cycloaddition;	95%

2-(Hydroxymethyl)allyl alcohol (3513-81-3) + methyl chloroformate (79-22-1) → 1,3-diacetoxy-2-methylenepropane (3775-29-9)

Conditions	Yield
With pyridine; dmap In dichloromethane at 25℃; for 24h;	94%

2-(Hydroxymethyl)allyl alcohol (3513-81-3) + 4-methoxy-benzaldehyde (123-11-5) → 2-(4-methoxyphenyl)-5-methylene-[1,3]dioxane (168321-65-1)

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 3h; Heating;	93%

2-chloromethyl-3-chloroprop-1-ene (1871-57-4) + 2-(Hydroxymethyl)allyl alcohol (3513-81-3) → (+/-)-3-methylene-1,5-diphenylpentanediol (71370-00-8)

Conditions	Yield
With tin(ll) chloride; bis(benzonitrile)palladium(II) dichloride In N,N-dimethyl-formamide for 72h; Ambient temperature;	92%

2-(Hydroxymethyl)allyl alcohol (3513-81-3) + tert-butyldimethylsilyl chloride (18162-48-6) → 2-(tert-butyl-dimethyl-silanyloxymethyl)-prop-2-en-1-ol (116700-73-3)

Conditions	Yield
Stage #1: 2-(Hydroxymethyl)allyl alcohol With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 0.75h; Inert atmosphere; Stage #2: tert-butyldimethylsilyl chloride In tetrahydrofuran; mineral oil at 20℃; for 2h; Inert atmosphere;	92%
Stage #1: 2-(Hydroxymethyl)allyl alcohol With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; Inert atmosphere; Stage #2: tert-butyldimethylsilyl chloride In tetrahydrofuran; mineral oil at 20℃; for 1h; Inert atmosphere;	92%
With sodium hydride In tetrahydrofuran	91%

iodobenzene (591-50-4) + 2-(Hydroxymethyl)allyl alcohol (3513-81-3) → 2-benzylidene-1,3-propanediol (99186-23-9)

Conditions	Yield
With palladium diacetate; tributylphosphine; potassium carbonate In N,N-dimethyl-formamide at 80℃; for 1h;	91%

2-(Hydroxymethyl)allyl alcohol (3513-81-3) + cyclohexanone (108-94-1) → 3-methylene-1,5-dioxa-spiro[5.5]undecane (3290-73-1)

Conditions	Yield
With toluene-4-sulfonic acid In benzene for 4h; Condensation;	91%

2-(Hydroxymethyl)allyl alcohol (3513-81-3) → 5-methylene-1,3,2-dioxathiane 2-oxide (548482-49-1)

Conditions	Yield
With thionyl chloride In tetrachloromethane at 0℃; for 0.75h;	91%
With thionyl chloride In tetrachloromethane at 0℃; for 0.75h; Inert atmosphere;	90.63%
With thionyl chloride In tetrachloromethane at 0℃; for 0.833333h;	86%
With thionyl chloride In tetrachloromethane at 0℃; for 0.75h; Inert atmosphere;	9.63%
With thionyl chloride In dichloromethane at 0℃; for 0.75h; Inert atmosphere;

2-(Hydroxymethyl)allyl alcohol (3513-81-3) + 1-(bromomethyl)-4-(1,1-dimethylethyl)benzene (18880-00-7) → 2-(((4-(tert-butyl)benzyl)oxy)methyl)prop-2-en-1-ol (1360903-27-0)

Conditions	Yield
Stage #1: 2-(Hydroxymethyl)allyl alcohol With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; Inert atmosphere; Stage #2: 1-(bromomethyl)-4-(1,1-dimethylethyl)benzene With tetra-(n-butyl)ammonium iodide In tetrahydrofuran; mineral oil at 0 - 20℃; Inert atmosphere;	91%

triisopropylsilyl chloride (13154-24-0) + 2-(Hydroxymethyl)allyl alcohol (3513-81-3) → 2-methylidene-3-(triisopropylsilyloxy)-propan-1-ol (852235-21-3)

Conditions	Yield
With sodium hydride In tetrahydrofuran	90%
Stage #1: 2-(Hydroxymethyl)allyl alcohol With sodium hydride In tetrahydrofuran; mineral oil for 0.0833333h; Stage #2: triisopropylsilyl chloride In tetrahydrofuran; mineral oil for 3.08333h; Stage #3: With ammonium chloride In diethyl ether; water

2-(Hydroxymethyl)allyl alcohol (3513-81-3) + 4-methoxy-N'-phenylbenzohydrazonoyl chloride (40277-63-2) → [3-hydroxymethyl-5-(4-methoxyphenyl)-2-phenyl-3,4-dihydro-2H-pyrazol-3-yl]methanol

Conditions	Yield
With triethylamine In dichloromethane; water at 20℃; for 11h; Reagent/catalyst; Huisgen Cycloaddition;	89%

2-(Hydroxymethyl)allyl alcohol (3513-81-3) + ethyl 2-((N-(2,4,6-trichlorophenyl)sulfamoyl)amino)acetate (1354438-71-3) → ethyl 2-(4-methylene-1,1-dioxido-6-(2,4,6-trichlorophenyl)-1,2,6-thiadiazinan-2-yl)acetate (1354438-87-1)

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at -20 - 20℃; for 5h; Inert atmosphere;	89%

4-acetoxy azetidinone (28562-53-0) + 2-(Hydroxymethyl)allyl alcohol (3513-81-3) → 4-<(3-hydroxy-2-methylenepropyl)oxy>-2-azetidinone (109975-85-1)

Conditions	Yield
With zinc diacetate In benzene for 1h; Heating;	86%

2-(Hydroxymethyl)allyl alcohol (3513-81-3) + Methyl 3-mercaptopropionate (2935-90-2) → methyl 3-((3-hydroxy-2-(hydroxymethyl)propyl)thio)propanoate

Conditions	Yield
With 2,2-dimethoxy-2-phenylacetophenone In acetonitrile at 20℃; for 0.5h; UV-irradiation;	86%

2-(Hydroxymethyl)allyl alcohol (3513-81-3) + benzoyl chloride (98-88-4) → 2-(hydroxymethyl)allyl benzoate

Conditions	Yield
With triethylamine In acetonitrile at 0 - 20℃; for 3h;	86%

2-(Hydroxymethyl)allyl alcohol (3513-81-3) + dichlorodiphenoxymethane (4885-03-4) → 3,9-dimethylene-1,5,7,11-tetraoxaspiro [5.5] undecane (55849-58-6)

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 1h;	85%

2-(Hydroxymethyl)allyl alcohol (3513-81-3) + acetic anhydride (108-24-7) → 2-(acetoxymethyl)prop-2-en-1-ol (57859-50-4)

Conditions	Yield
With pyridine; dmap In dichloromethane at 20℃; for 16h;	85%
With dmap; triethylamine	80%
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere;	30%
With triethylamine In dichloromethane at 0 - 20℃; for 5h;
With lanthanum(III) nitrate hexahydrate at 20℃;

2-(Hydroxymethyl)allyl alcohol (3513-81-3) + bis(trichloromethyl) carbonate (32315-10-9) → 2-methylidenetrimethylene carbonate (3775-32-4)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 2.5h; Inert atmosphere;	85%
With pyridine In tetrahydrofuran at 20℃; for 8h;	24 %Spectr.

Upstream product

• 19184-65-7 2-(bromomethyl)-2-(hydroxymethyl)propane-1,3-diol 
• 3775-29-9 1,3-diacetoxy-2-methylenepropane 
• 6707-12-6 2,2-di-hydroxymethylnorborn-5-ene 
• 40364-84-9 2-hydroxymethyl-propenal 
• 113859-64-6 2,2-Dimethyl-propionic acid 2-(2,2-dimethyl-propionyloxymethyl)-allyl ester 
• 7732-18-5 water 
• 620161-75-3 2-methylene-1,3-propane-[bis-(tert-butyl)carbonate] 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 74181-34-3 2,2,-dimethyl-1,3-dioxan-5-one 
• 1607-00-7 pentaerythrityl mononitrate 
• 1871-57-4 2-chloromethyl-3-chloroprop-1-ene 

Downstream Products

• 3775-29-9 1,3-diacetoxy-2-methylenepropane 
• 99186-23-9 2-benzylidenepropane-1,3-diol 
• 96694-06-3 1,2-Bis<4-phenyl-2-butanol-1-yl>ethene 
• 181366-97-2 2-Methylene-6-phenyl-hexane-1,4-diol 
• 78-85-3 2-methylpropenal 
• 412944-65-1 5-methylene-2-phenoxy-[1,3,2]dioxaphosphinane 2-oxide 
• 5491-03-2 2-[(dibenzylamino)methyl]prop-2-en-1-ol 
• 168321-65-1 2-(4-methoxyphenyl)-5-methylene-[1,3]dioxane 
• 177606-51-8 2-<(tert-butyldiphenylsilyloxy)methyl>prop-2-en-1-ol 
• 849442-28-0 2-(4-trifluoromethoxy-phenoxymethyl)-prop-2-en-1-ol 
• 1058138-82-1 1-(4-methoxyphenyl)-4-methylene-2-(4-hydroxyphenyl)pyrrolidine 
• 1058138-80-9 1,2-bis(4-methoxyphenyl)-4-methylenepyrrolidine 
• 94956-94-2 4-methylene-1,2-diphenylpyrrolidine 
• 1058138-78-5 1-(4-methoxyphenyl)-4-methylene-2-phenylpyrrolidine 

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