10476-95-6

Basic information

• Product Name: 2-METHYL-2-PROPENE-1,1-DIOL DIACETATE
• Synonyms: 2-METHYL-2-PROPENE-1,1-DIOL DIACETATE;METHACROLEIN DIACETYLACETAL;1-(Acetyloxy)-2-methyl-2-propenyl acetate;1-diol,2-methyl-2-propene-diacetate;1-diol,2-methyl-2-propene-diacetate[qr];2-methyl-2-propene-1,1-diol;2-methyl-2-propene-1,1-dioldiacetate[qr];Acetic acid, 2-methyl-2-propene-1,1-diol diester
• CAS NO: 10476-95-6
• Molecular Formula: C₈H₁₂O₄
• Molecular Weight: 172.18
• EINECS: 233-974-2
• Product Categories: CMLLYL
• Mol File: 10476-95-6.mol
• Article Data: 6

Chemical Properties

• Melting Point: −15 °C(lit.)
• Boiling Point: 191 °C(lit.)
• Flash Point: 182 °F
• Appearance: /
• Density: 1.039 g/mL at 25 °C(lit.)
• Vapor Pressure: 760 mm Hg ( 191 °C)
• Refractive Index: n20/D 1.424(lit.)
• CAS DataBase Reference: 2-METHYL-2-PROPENE-1,1-DIOL DIACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-METHYL-2-PROPENE-1,1-DIOL DIACETATE(10476-95-6)
• EPA Substance Registry System: 2-METHYL-2-PROPENE-1,1-DIOL DIACETATE(10476-95-6)

Safety Data

• Hazard Codes: T+
• Statements: 26/27/28
• Safety Statements: 23-26-27-36/37/39-45
• RIDADR: UN 2810 6.1/PG 1
• WGK Germany: 3
• RTECS: UC9800000
• F: 9-21
• HazardClass: 6.1(a)
• PackingGroup: II
• Hazardous Substances Data: 10476-95-6(Hazardous Substances Data)

Usage

Chemical Properties

Liquid.Slightly soluble in water. Combustible.

Uses

Chemical intermediate, can provide controlled release of methacrolein in acid solution.

General Description

A liquid. Density 1.04 g / cm3; highly toxic.

Reactivity Profile

2-METHYL-2-PROPENE-1,1-DIOL DIACETATE reacts exothermically with acids. Strong oxidizing acids may cause a reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated with basic solutions. Flammable hydrogen may be generated by mixing with alkali metals and hydrides. Reacts readily with mercaptans. Acidic conditions favor breakdown to methacrolein, which is subject to possibly vigorous polymerization.

Fire Hazard

When heated to decomposition, 2-METHYL-2-PROPENE-1,1-DIOL DIACETATE emits acrid smoke and irritating fumes.

Safety Profile

Poison by inhalation, skin contactand intraperitoneal routes. Moderately toxic by ingestion. When heated to decomposition it emitsacrid smoke and irritating fumes.

InChI:InChI=1/C8H12O4/c1-5(2)8(11-6(3)9)12-7(4)10/h8H,1H2,2-4H3

Synthetic route

2-methylpropenal (78-85-3) + acetic anhydride (108-24-7) → methallylidene diacetate (10476-95-6)

Conditions	Yield
phosphorus trichloride at 20℃; for 10h;	88%
With lithium tetrafluoroborate In diethyl ether at 20℃; for 22h;	87%
With boron trifluoride diethyl etherate at -10℃; for 3.3h;	85%

1,3,3-trimethylcyclopropene (3664-56-0) + thallium(III) acetate (2570-63-0) → methallylidene diacetate (10476-95-6)

Conditions	Yield
In dichloromethane

acetic acid (64-19-7) + 1-acetyloxy-2-methylpropene (14478-14-9) → methallylidene diacetate (10476-95-6)

Conditions	Yield
(electrochemical oxidation);

1,2-dimethoxybenzene (91-16-7) + methallylidene diacetate (10476-95-6) → 1-acetoxy-2-methyl-3-(3,4-dimethoxyphenyl)propene (714237-84-0)

Conditions	Yield
zinc(II) chloride at 25 - 26℃; for 1.5h; Product distribution / selectivity;	95.1%
boron trifluoride diethyl etherate at 18 - 23℃; for 2h; Product distribution / selectivity;	94.4%
Stage #1: 1,2-dimethoxybenzene; methallylidene diacetate; boron trifluoride diethyl etherate; titanium tetrachloride at 8 - 12℃; for 1.58333h; Stage #2: With hydrogenchloride In dichloromethane; water for 0.5h; Product distribution / selectivity;	12%
With boron trifluoride diethyl etherate; titanium tetrachloride at 0℃;

methallylidene diacetate (10476-95-6) + methoxybenzene (100-66-3) → 1-acetoxy-2-methyl-3-(4-methoxyphenyl)propene (77104-98-4)

Conditions	Yield
ytterbium(III) triflate at 38 - 40℃; for 3h; Product distribution / selectivity;	94.2%
boron trifluoride diethyl etherate at 24 - 25℃; for 1.03333h; Product distribution / selectivity;	93.4%
copper(II) bis(trifluoromethanesulfonate) at 38 - 40℃; for 3h; Product distribution / selectivity;	92.7%
With titanium tetrachloride at -10℃; for 3.5h; Friedel-Crafts Alkylation; regioselective reaction;

Methylenedioxybenzene (274-09-9) + methallylidene diacetate (10476-95-6) → (1E/Z)-acetic acid 3-(1,3-benzodioxol-5-yl)-2-methylprop-1-enyl ester

Conditions	Yield
ytterbium(III) chloride at 39 - 40℃; for 3h; Product distribution / selectivity;	93.1%
tin(IV) chloride at 38 - 40℃; for 3h; Product distribution / selectivity;	88.5%
tin(II) trifluoromethanesulfonate at 38 - 40℃; for 3h; Product distribution / selectivity;	87.6%

methallylidene diacetate (10476-95-6) + methyl 3,4-dihydro-2(2H)-naphthalenone-1-carboxylate (31202-23-0) → 1-((E)-3-Acetoxy-2-methyl-allyl)-2-oxo-1,2,3,4-tetrahydro-naphthalene-1-carboxylic acid methyl ester (141077-82-9)

Conditions	Yield
With benzenesulfonamide; palladium diacetate; triphenylphosphine In toluene for 29h; Heating;	86%

benzo-1,4-dioxane (493-09-4) + methallylidene diacetate (10476-95-6) → 1-acetoxy-2-methyl-3-(3,4-ethylenedioxyphenyl)propene

Conditions	Yield
boron trifluoride diethyl etherate at 24℃; for 2h; Product distribution / selectivity;	78.2%

methallylidene diacetate (10476-95-6) + 8-oxo-1,4-dioxa-spiro[4.5]decane-7-carboxylic acid methyl ester (52506-21-5) → C14H20O6 + C16H22O7

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium diacetate; triphenylphosphine In 1,4-dioxane for 16h; Heating;	A 18% B 51%

methallylidene diacetate (10476-95-6) + 2-Carbomethoxy-4-methylenecyclohexanone (141077-81-8) → 1-((E)-3-Acetoxy-2-methyl-allyl)-5-methylene-2-oxo-cyclohexanecarboxylic acid methyl ester (141077-85-2)

Conditions	Yield
With benzenesulfonamide; palladium diacetate; triphenylphosphine In 1,4-dioxane for 16h; Heating;	48%

methallylidene diacetate (10476-95-6) + 4-chloro-aniline (106-47-8) → 6-chloro-3-methylquinoline (97041-62-8)

Conditions	Yield
With hydrogenchloride In 1,4-dioxane; water at 100 - 120℃; for 7.5h;	47%
With sulfuric acid; orthoarsenic acid

syn-benzaldehyde oxime (932-90-1, 622-31-1, 140461-24-1, 140461-25-2, 622-32-2) + methallylidene diacetate (10476-95-6) → acetic acid acetoxy-(5-methyl-3-phenyl-4,5-dihydroisoxazol-5-yl)methyl ester

Conditions	Yield
Stage #1: syn-benzaldehyde oxime With N-hydroxyiminoyl chloride In dichloromethane; N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: methallylidene diacetate With triethylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 39h;	35%

8-amino quinoline (578-66-5) + methallylidene diacetate (10476-95-6) → 3-methyl-1,10-phenanthroline (17044-07-4)

Conditions	Yield
With arsenic(V) oxide; sulfuric acid at 100 - 140℃;

6-methyl-8-aminoquinoline (68420-93-9) + methallylidene diacetate (10476-95-6) → 3,5-dimethyl-[1,10]phenanthroline

Conditions	Yield
With arsenic(V) oxide; sulfuric acid

3-methyl-[8]quinolylamine (3393-71-3) + methallylidene diacetate (10476-95-6) → 2,9-dimethyl-1,10-phenanthroline (3002-80-0)

Conditions	Yield
With arsenic(V) oxide; sulfuric acid

4-methyl-8-aminoquinoline (62748-01-0) + methallylidene diacetate (10476-95-6) → 3,7-dimethyl-[1,10]phenanthroline (107919-97-1)

Conditions	Yield
With arsenic(V) oxide; sulfuric acid

8-amino-6-chloroquinoline (5470-75-7) + methallylidene diacetate (10476-95-6) → 5-chloro-3-methyl-[1,10]phenanthroline

Conditions	Yield
With sulfuric acid; orthoarsenic acid at 100 - 140℃;

3,4-dimethyl-[8]quinolylamine (3393-72-4) + methallylidene diacetate (10476-95-6) → 3,4,8-trimethyl-[1,10]phenanthroline (3248-06-4)

Conditions	Yield
With arsenic(V) oxide; sulfuric acid

3,5,6-trimethyl-[8]quinolylamine (3376-14-5) + methallylidene diacetate (10476-95-6) → 3,5,6,8-tetramethyl-1,10-phenanthroline (2747-15-1)

Conditions	Yield
With arsenic(V) oxide; sulfuric acid at 100 - 140℃;

3,4,6-trimethyl-[8]quinolylamine (860194-22-5) + methallylidene diacetate (10476-95-6) → 3,4,6,8-tetramethyl-[1,10]phenanthroline

Conditions	Yield
With arsenic(V) oxide; sulfuric acid at 100 - 140℃;

Upstream product

• 64-19-7 acetic acid 
• 14478-14-9 1-acetyloxy-2-methylpropene 
• 3664-56-0 1,3,3-trimethylcyclopropene 
• 2570-63-0 thallium(III) acetate 
• 78-85-3 2-methylpropenal 
• 108-24-7 acetic anhydride 

Downstream Products

• 97041-62-8 6-chloro-3-methylquinoline 
• 2801-32-3 3-methyl-8-nitroquinoline 
• 141077-83-0 1-((E)-3-Acetoxy-2-methyl-allyl)-5-methyl-2-oxo-cyclohexanecarboxylic acid methyl ester 
• 141077-85-2 1-((E)-3-Acetoxy-2-methyl-allyl)-5-methylene-2-oxo-cyclohexanecarboxylic acid methyl ester 
• 77104-98-4 1-acetoxy-2-methyl-3-(4-methoxyphenyl)propene 
• 6022-59-9 3-(4-(sec-butyl)phenyl)-2-methylpropanal 
• 6839-77-6 Acetat v. 2-Methyl-3-<4-isopropyl-phenyl>-propen-(1)-ol-(1) 
• 103-95-7 cyclamenaldehyde 
• 6502-20-1 α-methyl-o-isopropylhydroxycinnamaldehyde 
• 36207-16-6 3-(4-ethylphenyl)-2-methylpropanal 
• 41496-43-9 2-methyl-3-(4-methylphenyl)propanal 
• 57918-84-0 C₁₁H₁₄O 

Relevant articles and documents

Phosphorus Trichloride as Catalyst in the Preparation of 1,1-Diacetates from Aldehydes

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Method for preparing anethol propionaldehyde by anisole

The invention relates to the technical field of organic synthesis, in particular to a method for preparing anethoxyl propionaldehyde by anisole, which comprises anisole and 2 - methylallyl diacetate or anisole. 2 - Methacrolein and acetic anhydride were added to the reaction vessel to catalyze the reaction. Then 1 - acetoxy -2 - methyl -3 - (4 - methoxyphenyl) propylene was added to a reaction vessel carrying an alcoholic solvent and an ester exchange catalyst to carry out an ester exchange reaction. The method solves the problems that the cost of anisic aldehyde or anisaldehyde in the product is high due to the expensive price of anisaldehyde or anethol in the prior art, and anisole is synthesized into anethol propionaldehyde. The synthetic anisanylpropanal has a sufficiently high purity. Can be used for perfumery.

2-METHYL-3-(3,4-METHYLENEDIOXYPHENYL)PROPANAL, AND METHOD FOR PRODUCTION THEREOF

Disclosed are: (1) a method for producing 2-methyl-3-(3,4-methylenedioxyphenyl)propanal, which comprises the step of providing a reaction mixture containing 1-acetoxy-2-methyl-3-(3,4-methylenedioxyphenyl)-1-propene by a process for reacting 1,2-methylenedioxybenzene with 2-methyl-3,3-diacetoxypropene or a process for reacting 1,2-methylenedioxybenzene, methacrolein and acetic anhydride with one another; subjecting the reaction mixture to hydrolysis or transesterification with an alcohol to provide a reaction mixture containing 2-methyl-3-(3,4-methylenedioxyphenyl)propanal; and purifying by distilling the reaction mixture, wherein a high boiling point compound contained in the reaction mixture is removed by a specific procedure; and (2) 2-methyl-3-(3,4-methylenedioxyphenyl)-propanal produced by the method, which has an acetic acid content of a less than 40 ppm, is useful as a perfume, and has a high purity.