2-Methylene-1,3-propanediol supplier

Name
2-Methylene-1,3-propanediol
EINECS 222-516-7
CAS No. 3513-81-3
Article Data22
CAS DataBase
Density 1.043 g/cm³
Solubility
Melting Point
Formula C₄H₈O₂
Boiling Point 236.203 °C at 760 mmHg
Molecular Weight 88.1063
Flash Point 98.573 °C
Transport Information
Appearance clear colorless to pale yellow viscous liquid
Safety 26-36
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 2-Methylidenepropane-1,3-diol;
PSA 40.46000
LogP -0.47280

Synthetic route

: 3775-29-9
1,3-diacetoxy-2-methylenepropane

: 3513-81-3
2-(Hydroxymethyl)allyl alcohol

Conditions

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℃;

: 620161-75-3
2-methylene-1,3-propane-[bis-(tert-butyl)carbonate]

: 3513-81-3
2-(Hydroxymethyl)allyl alcohol

Conditions

Conditions	Yield
With dmap In tetrahydrofuran Heating;	98%

: 19184-65-7
2-(bromomethyl)-2-(hydroxymethyl)propane-1,3-diol

A: 2754-18-9
3,3-bis(hydroxymethyl)oxetane

B: 3513-81-3
2-(Hydroxymethyl)allyl alcohol

Conditions

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

: 1607-00-7
pentaerythrityl mononitrate

A: 2754-18-9
3,3-bis(hydroxymethyl)oxetane

B: 3513-81-3
2-(Hydroxymethyl)allyl alcohol

Conditions

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

: 1871-57-4
2-chloromethyl-3-chloroprop-1-ene

: 3513-81-3
2-(Hydroxymethyl)allyl alcohol

Conditions

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

: 6707-12-6
2,2-di-hydroxymethylnorborn-5-ene

: 3513-81-3
2-(Hydroxymethyl)allyl alcohol

Conditions

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

: 19184-65-7
2-(bromomethyl)-2-(hydroxymethyl)propane-1,3-diol

: 3513-81-3
2-(Hydroxymethyl)allyl alcohol

Conditions

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

: 40364-84-9
2-hydroxymethyl-propenal

: 3513-81-3
2-(Hydroxymethyl)allyl alcohol

Conditions

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

: 113859-64-6
2,2-Dimethyl-propionic acid 2-(2,2-dimethyl-propionyloxymethyl)-allyl ester

: 3513-81-3
2-(Hydroxymethyl)allyl alcohol

Conditions

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

: 2-isopropoxy-4-methylene-[1,2]oxaborolane

: 3513-81-3
2-(Hydroxymethyl)allyl alcohol

Conditions

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

: 19184-65-7
2-(bromomethyl)-2-(hydroxymethyl)propane-1,3-diol

: 7732-18-5
water

barium oxide: barium oxide

: 3513-81-3
2-(Hydroxymethyl)allyl alcohol

...Expand

: 19184-65-7
2-(bromomethyl)-2-(hydroxymethyl)propane-1,3-diol

: 7732-18-5
water

silver oxide: silver oxide

: 3513-81-3
2-(Hydroxymethyl)allyl alcohol

...Expand

: 19184-65-7
2-(bromomethyl)-2-(hydroxymethyl)propane-1,3-diol

ethanolic KOH-solution: ethanolic KOH-solution

A: 2754-18-9
3,3-bis(hydroxymethyl)oxetane

B: 3513-81-3
2-(Hydroxymethyl)allyl alcohol

...Expand

: 1779-49-3
Methyltriphenylphosphonium bromide

: 74181-34-3
2,2,-dimethyl-1,3-dioxan-5-one

: 3513-81-3
2-(Hydroxymethyl)allyl alcohol

Conditions

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;

: 3513-81-3
2-(Hydroxymethyl)allyl alcohol

: 100-39-0
benzyl bromide

: 27441-79-8
2-methylenepropane-1,3-bisbenzyl ether

Conditions

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℃;

: 3513-81-3
2-(Hydroxymethyl)allyl alcohol

: 79-22-1
methyl chloroformate

: 130667-36-6
2-{[(methoxycarbonyl)oxy]methyl}allyl methyl carbonate

Conditions

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

: 3513-81-3
2-(Hydroxymethyl)allyl alcohol

: 58479-61-1
tert-butylchlorodiphenylsilane

: 177606-51-8
2-<(tert-butyldiphenylsilyloxy)methyl>prop-2-en-1-ol

Conditions

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%

: 3513-81-3
2-(Hydroxymethyl)allyl alcohol

: 24424-99-5
di-tert-butyl dicarbonate

: 620161-75-3
2-methylene-1,3-propane-[bis-(tert-butyl)carbonate]

Conditions

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%

: 108-05-4
vinyl acetate

: 3513-81-3
2-(Hydroxymethyl)allyl alcohol

: 3775-29-9
1,3-diacetoxy-2-methylenepropane

Conditions

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

: 3513-81-3
2-(Hydroxymethyl)allyl alcohol

: 108-24-7
acetic anhydride

: 3775-29-9
1,3-diacetoxy-2-methylenepropane

Conditions

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

: 2426-02-0
3,4,5,6-Tetrahydrophthalic anhydride

: 3513-81-3
2-(Hydroxymethyl)allyl alcohol

: 3a-hydroxymethyl-1-oxo-hexahydro-2-oxa-cyclopenta<1,4>cyclobuta<1,2>benzene-4a-carboxylic acid

Conditions

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

: 3513-81-3
2-(Hydroxymethyl)allyl alcohol

: 2163-42-0
2-methyl-1.3-propanediol

Conditions

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

: 3513-81-3
2-(Hydroxymethyl)allyl alcohol

: 340184-54-5
(2-hydroxymethyl-oxiranyl)-methanol

Conditions

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

: 3513-81-3
2-(Hydroxymethyl)allyl alcohol

: 100-52-7
benzaldehyde

: 71370-00-8
(+/-)-3-methylene-1,5-diphenylpentanediol

Conditions

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

: 3513-81-3
2-(Hydroxymethyl)allyl alcohol

: 15424-14-3
N-phenylbenzohydrazonoyl chloride

: (3-hydroxymethyl-2,5-diphenyl-3,4-dihydro-2H-pyrazol-3-yl)methanol

Conditions

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

: 3513-81-3
2-(Hydroxymethyl)allyl alcohol

: 79-22-1
methyl chloroformate

: 3775-29-9
1,3-diacetoxy-2-methylenepropane

Conditions

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

: 3513-81-3
2-(Hydroxymethyl)allyl alcohol

: 123-11-5
4-methoxy-benzaldehyde

: 168321-65-1
2-(4-methoxyphenyl)-5-methylene-[1,3]dioxane

Conditions

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

: 1871-57-4
2-chloromethyl-3-chloroprop-1-ene

: 3513-81-3
2-(Hydroxymethyl)allyl alcohol

: 71370-00-8
(+/-)-3-methylene-1,5-diphenylpentanediol

Conditions

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

: 3513-81-3
2-(Hydroxymethyl)allyl alcohol

: 18162-48-6
tert-butyldimethylsilyl chloride

: 116700-73-3
2-(tert-butyl-dimethyl-silanyloxymethyl)-prop-2-en-1-ol

Conditions

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%

: 591-50-4
iodobenzene

: 3513-81-3
2-(Hydroxymethyl)allyl alcohol

: 99186-23-9
2-benzylidene-1,3-propanediol

Conditions

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

: 3513-81-3
2-(Hydroxymethyl)allyl alcohol

: 108-94-1
cyclohexanone

: 3290-73-1
3-methylene-1,5-dioxa-spiro[5.5]undecane

Conditions

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

: 3513-81-3
2-(Hydroxymethyl)allyl alcohol

: 548482-49-1
5-methylene-1,3,2-dioxathiane 2-oxide

Conditions

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;

: 3513-81-3
2-(Hydroxymethyl)allyl alcohol

: 18880-00-7
1-(bromomethyl)-4-(1,1-dimethylethyl)benzene

: 1360903-27-0
2-(((4-(tert-butyl)benzyl)oxy)methyl)prop-2-en-1-ol

Conditions

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%

: 13154-24-0
triisopropylsilyl chloride

: 3513-81-3
2-(Hydroxymethyl)allyl alcohol

: 852235-21-3
2-methylidene-3-(triisopropylsilyloxy)-propan-1-ol

Conditions

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

: 3513-81-3
2-(Hydroxymethyl)allyl alcohol

: 40277-63-2
4-methoxy-N'-phenylbenzohydrazonoyl chloride

: [3-hydroxymethyl-5-(4-methoxyphenyl)-2-phenyl-3,4-dihydro-2H-pyrazol-3-yl]methanol

Conditions

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

: 3513-81-3
2-(Hydroxymethyl)allyl alcohol

: 1354438-71-3
ethyl 2-((N-(2,4,6-trichlorophenyl)sulfamoyl)amino)acetate

: 1354438-87-1
ethyl 2-(4-methylene-1,1-dioxido-6-(2,4,6-trichlorophenyl)-1,2,6-thiadiazinan-2-yl)acetate

Conditions

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

: 28562-53-0
4-acetoxy azetidinone

: 3513-81-3
2-(Hydroxymethyl)allyl alcohol

: 109975-85-1
4-<(3-hydroxy-2-methylenepropyl)oxy>-2-azetidinone

Conditions

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

: 3513-81-3
2-(Hydroxymethyl)allyl alcohol

: 2935-90-2
Methyl 3-mercaptopropionate

: methyl 3-((3-hydroxy-2-(hydroxymethyl)propyl)thio)propanoate

Conditions

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

: 3513-81-3
2-(Hydroxymethyl)allyl alcohol

: 98-88-4
benzoyl chloride

: 2-(hydroxymethyl)allyl benzoate

Conditions

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

: 3513-81-3
2-(Hydroxymethyl)allyl alcohol

: 4885-03-4
dichlorodiphenoxymethane

: 55849-58-6
3,9-dimethylene-1,5,7,11-tetraoxaspiro [5.5] undecane

Conditions

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

: 3513-81-3
2-(Hydroxymethyl)allyl alcohol

: 108-24-7
acetic anhydride

: 57859-50-4
2-(acetoxymethyl)prop-2-en-1-ol

Conditions

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℃;

: 3513-81-3
2-(Hydroxymethyl)allyl alcohol

: 32315-10-9
bis(trichloromethyl) carbonate

: 3775-32-4
2-methylidenetrimethylene carbonate

Conditions

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.

2-Methylene-1,3-propanediol Specification

The 2-Methylene-1,3-propanediol, with the CAS registry number 3513-81-3, is also known as 1,3-Propanediol, 2-methylene-. It belongs to the product categories of Alcohols; Monomers; Polymer Science. Its EINECS registry number is 222-516-7. This chemical's molecular formula is C₄H₈O₂ and molecular weight is 88.11. What's more, its IUPAC name is called 2-Methylidenepropane-1,3-diol.

Physical properties about 2-Methylene-1,3-propanediol are: (1)ACD/LogP: -0.669; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.67; (4)ACD/LogD (pH 7.4): -0.67; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 10.31; (8)ACD/KOC (pH 7.4): 10.31; (9)#H bond acceptors: 2; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 40.46 Å²; (13)Index of Refraction: 1.462; (14)Molar Refractivity: 23.218 cm³; (15)Molar Volume: 84.469 cm³; (16)Polarizability: 9.204×10^-24cm³; (17)Surface Tension: 38.159 dyne/cm; (18)Density: 1.043 g/cm³; (19)Flash Point: 98.573 °C; (20)Enthalpy of Vaporization: 54.976 kJ/mol; (21)Boiling Point: 236.203 °C at 760 mmHg; (22)Vapour Pressure: 0.0090 mmHg at 25 °C.

Preparation of 2-Methylene-1,3-propanediol: this chemical can be prepared by 3-chloro-2-chloromethyl-propene. The reaction occurs with reagents H₂O, CaCO₃ and other condition of heating for 5 days. The yield is 65 %.

2-Methylene-1,3-propanediol can be prepared by 3-chloro-2-chloromethyl-propene.

Uses of 2-Methylene-1,3-propanediol: it is used to produce other chemicals. For example, it can react with 4-acetoxy-azetidin-2-one to get 4-(2-hydroxymethyl-allyloxy)-azetidin-2-one. This reaction needs reagent Zn(OAc)₂*2H₂O, solvent benzene and other condition of heating for 1 hour. The yield is 86 %.

2-Methylene-1,3-propanediol can react with 4-acetoxy-azetidin-2-one to get 4-(2-hydroxymethyl-allyloxy)-azetidin-2-one.

When you are dealing with this chemical, you should be very careful. This chemical may cause inflammation to the skin or other mucous membranes. And it is irritating to eyes, respiratory system and skin. Therefore, you should wear suitable protective clothing. In case of contacting with eyes, you should rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1) SMILES: OC/C(=C)CO
(2) InChI: InChI=1S/C4H8O2/c1-4(2-5)3-6/h5-6H,1-3H2
(3) InChIKey: JFFYKITVXPZLQS-UHFFFAOYSA-N

Product Name

2-Methylene-1,3-propanediol

Synthetic route

2-Methylene-1,3-propanediol Specification

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