Methylene Diacetate supplier

Name
METHYLENE DIACETATE, 99
EINECS 200-258-5
CAS No. 628-51-3
Article Data44
CAS DataBase
Density 1.119 g/mL at 25 °C(lit.)
Solubility
Melting Point ?23 °C(lit.)
Formula C₅H₈O₄
Boiling Point 164.5 °C at 760 mmHg
Molecular Weight 132.116
Flash Point 72.6 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols Xi
Synonyms Methanediol,diacetate (6CI,7CI,8CI,9CI);Diacetoxymethane;Methylene diacetate;Methyleneglycol diacetate;NSC 57545;
PSA 52.60000
LogP 0.07010

Synthetic route

: 50-00-0
formaldehyd

: 108-24-7
acetic anhydride

: 628-51-3
diacetoxymethane

Conditions

Conditions	Yield
With solid-phase supported silica chloride at 20℃; for 0.166667h; Neat (no solvent); chemoselective reaction;	90%

: 75-09-2
dichloromethane

: 143314-17-4
1-ethyl-3-methylimidazolium acetate

A: 628-51-3
diacetoxymethane

B: 65039-09-0
1-ethyl-3-methyl-1H-imidazol-3-ium chloride

Conditions

Conditions	Yield
at 50℃; for 16h; Inert atmosphere;	A 86% B n/a

...Expand

: 143314-17-4
1-ethyl-3-methylimidazolium acetate

: 74-95-3
1,1-dibromomethane

A: 628-51-3
diacetoxymethane

B: 65039-08-9
3-ethyl-1-methyl-1H-imidazol-3-ium bromide

Conditions

Conditions	Yield
at 20℃; for 2h; Inert atmosphere;	A 86% B n/a

...Expand

: 50-00-0
formaldehyd

: 503-17-3
dimethylacetylene

A: 628-51-3
diacetoxymethane

B: 108-24-7
acetic anhydride

C: 64-19-7
acetic acid

D: 431-03-8
dimethylglyoxal

Conditions

Conditions	Yield
With ozone In dichloromethane at -100℃;	A 7% B 71% C 17% D 5%

...Expand

: 3088-15-1
4,6-dibenzoylresorcinol

: 109-89-7
diethylamine

A 2-(acetoxymethyl)-4,6-dibenzovlresorcinol: 2-(acetoxymethyl)-4,6-dibenzovlresorcinol

B: 628-51-3
diacetoxymethane

Conditions

Conditions	Yield
With paraformaldehyde In acetic acid	A n/a B 68%

...Expand

: 814-78-8
3-Methyl-3-buten-2-one

A: 628-51-3
diacetoxymethane

B: 108-24-7
acetic anhydride

C: 131250-90-3
meso-3-methyl-3-(3-methyl-1,2,4-trioxolan-3-yl)-1,2,4-trioxolane

D: 64-19-7
acetic acid

Conditions

Conditions	Yield
With ozone In polyethylene at -75℃; for 3.5h;	A n/a B n/a C 9% D n/a

...Expand

: 186581-53-3, 908094-01-9
diazomethane

: 628-51-3
diacetoxymethane

Conditions

Conditions	Yield
With lead(IV) acetate; benzene

: 50-00-0
formaldehyd

: 4082-91-1
bis(acetoxymethyl)ether

A: 628-51-3
diacetoxymethane

B: 4082-92-2
bis-acetoxymethoxy-methane

C: 27969-30-8
1,7-diacetoxy-2,4,6-trioxa-heptane

Conditions

Conditions	Yield
at 140 - 150℃;

...Expand

: 75-11-6
diiodomethane

: 563-63-3
silver(I) acetate

: 628-51-3
diacetoxymethane

: 625-56-9
Chloromethyl acetate

: 127-08-2
potassium acetate

: 628-51-3
diacetoxymethane

: 546-67-8
lead(IV) tetraacetate

: 64-19-7
acetic acid

A: 13831-30-6
acetoxyacetic acid

B: 34557-54-5
methane

C: 628-51-3
diacetoxymethane

D: 15719-64-9, 15719-76-3, 97762-63-5
methylammonium carbonate

Conditions

Conditions	Yield
at 120℃;

...Expand

: 625-56-9
Chloromethyl acetate

: 64-19-7
acetic acid

: 628-51-3
diacetoxymethane

Conditions

Conditions	Yield
With silver(l) oxide In diethyl ether

: 50-00-0
formaldehyd

: 75-36-5
acetyl chloride

: 628-51-3
diacetoxymethane

Conditions

Conditions	Yield
With zinc(II) chloride

: 110-88-3
1,3,5-Trioxan

: 64-19-7
acetic acid

: 628-51-3
diacetoxymethane

Conditions

Conditions	Yield
With acetic anhydride for 15h; Ambient temperature;	4 % Spectr.

: 814-78-8
3-Methyl-3-buten-2-one

A: 628-51-3
diacetoxymethane

B: 108-24-7
acetic anhydride

C: 64-19-7
acetic acid

D: 431-03-8
dimethylglyoxal

Conditions

Conditions	Yield
With ozone In dichloromethane-d2 at -78℃; Title compound not separated from byproducts;	A 2 % Spectr. B 60 % Spectr. C 15 % Spectr. D 9 % Spectr.

...Expand

: 814-78-8
3-Methyl-3-buten-2-one

A: 628-51-3
diacetoxymethane

B: 108-24-7
acetic anhydride

C: 131250-90-3
meso-3-methyl-3-(3-methyl-1,2,4-trioxolan-3-yl)-1,2,4-trioxolane

D: 431-03-8
dimethylglyoxal

Conditions

Conditions	Yield
With ozone In polyethylene at -75℃; for 4h; Further byproducts given;	A 6 % Spectr. B 58 % Spectr. C 8 % Spectr. D 1 % Spectr.

...Expand

: 114988-54-4
4-propenyl-1,3-dioxane, E-isomer

: 108-24-7
acetic anhydride

A: 628-51-3
diacetoxymethane

B: 114988-56-6
1,5-diacetoxy-3-hexene

C: 114628-86-3
1,3-diacetoxy-4-hexene

Conditions

Conditions	Yield
With sulfuric acid at 65 - 75℃; for 2.5h; Title compound not separated from byproducts;	A 2.0 g B n/a C n/a

...Expand

: 108-24-7
acetic anhydride

: 75-05-8
acetonitrile

A: 64-18-6
formic acid

B: 628-51-3
diacetoxymethane

Conditions

Conditions	Yield
With oxygen In N,N-dimethyl-formamide Product distribution; electrolysis;	A 0.04 % Chromat. B 0.14 % Chromat.

...Expand

: 108-24-7
acetic anhydride

: 75-05-8
acetonitrile

: 628-51-3
diacetoxymethane

Conditions

Conditions	Yield
With tetrabutylammomium bromide; oxygen In N,N-dimethyl-formamide Hg cathode, Pt anode, -1.0 V vs SCE; Yield given;

: 116-11-0
2-Methoxypropene

: 431-03-8
dimethylglyoxal

A: 628-51-3
diacetoxymethane

B: 108-24-7
acetic anhydride

C: 131250-90-3
meso-3-methyl-3-(3-methyl-1,2,4-trioxolan-3-yl)-1,2,4-trioxolane

Conditions

Conditions	Yield
With ozone In pentane at -78℃;	A 22 % Spectr. B 39 % Spectr. C 12 % Spectr.

...Expand

: 7664-93-9
sulfuric acid

: 108-24-7
acetic anhydride

formaldehyde gas: formaldehyde gas

: 628-51-3
diacetoxymethane

...Expand

: 7664-93-9
sulfuric acid

: 108-24-7
acetic anhydride

polyoxymethylene: polyoxymethylene

: 628-51-3
diacetoxymethane

Conditions

Conditions	Yield
bei Siedetemperatur;

...Expand

: 108-24-7
acetic anhydride

polyoxymethylene: polyoxymethylene

ZnCl2: ZnCl2

A: 628-51-3
diacetoxymethane

B: 4082-91-1
bis(acetoxymethyl)ether

Conditions

Conditions	Yield
at 130℃;

...Expand

: 7664-93-9
sulfuric acid

: 108-24-7
acetic anhydride

polyoxymethylene: polyoxymethylene

A: 628-51-3
diacetoxymethane

B: 4082-91-1
bis(acetoxymethyl)ether

C formaldehyde bis-acetoxymethyl-acetal: formaldehyde bis-acetoxymethyl-acetal

Conditions

Conditions	Yield
at 200℃;

...Expand

: 50-00-0
formaldehyd

: 7664-93-9
sulfuric acid

: 108-24-7
acetic anhydride

: 628-51-3
diacetoxymethane

...Expand

: 50-00-0
formaldehyd

: 7664-93-9
sulfuric acid

: 108-24-7
acetic anhydride

polyoxymethylene: polyoxymethylene

: 628-51-3
diacetoxymethane

Conditions

Conditions	Yield
bei Siedetemperatur;

...Expand

: 75-11-6
diiodomethane

: 64-19-7
acetic acid

acetate_of silver: acetate_of silver

: 628-51-3
diacetoxymethane

Conditions

Conditions	Yield
at 100℃;

...Expand

: 108-24-7
acetic anhydride

formaldehyde gas: formaldehyde gas

: 628-51-3
diacetoxymethane

Conditions

Conditions	Yield
With sulfuric acid

: 108-24-7
acetic anhydride

polyoxymethylene: polyoxymethylene

: 628-51-3
diacetoxymethane

Conditions

Conditions	Yield
With sulfuric acid bei Siedetemperatur;

: 628-51-3
diacetoxymethane

: N-(2-Benzenesulfonylamino-ethyl)-4-methyl-benzenesulfonamide

: 1-Benzenesulfonyl-3-(toluene-4-sulfonyl)-imidazolidine

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In acetic acid at 80℃; for 1h;	95%

: 628-51-3
diacetoxymethane

: 87751-69-7
rac-(E)-1,3-diphenyl-3-acetoxy-prop-1-ene

: 95071-02-6, 96482-67-6, 131065-36-6, 148553-10-0, 96482-64-3
dimethyl 2-[(E)-(S)-1,3-diphenylallyl]-malonate

Conditions

Conditions	Yield
With N,O-bis-(trimethylsilyl)-acetamide; (1R,2S)-2-dimethylamino-1-(ferrocenylthio)-1-phenylpropane; potassium acetate In dichloromethane at 20℃; for 20h;	88%

: 628-51-3
diacetoxymethane

: 108-24-7
acetic anhydride

: 50-00-0
formaldehyd

Conditions

Conditions	Yield
With solid-phase supported silica chloride In methanol at 20℃; for 0.5h;	88%

: 628-51-3
diacetoxymethane

: 87751-69-7
rac-(E)-1,3-diphenyl-3-acetoxy-prop-1-ene

: 95071-02-6, 96482-64-3, 131065-36-6, 148553-10-0, 96482-67-6
(R)-methyl 2-carbomethoxy-3,5-diphenylpent-4-enoate

Conditions

Conditions	Yield
With N,O-bis-(trimethylsilyl)-acetamide; (S)-2-benzylideneamino)-1-(ferrocenylthio)-3-methylbutane; potassium acetate In dichloromethane at 20℃; for 90h;	85%

: 1073-67-2
4-vinylbenzyl chloride

: 628-51-3
diacetoxymethane

: (+/-)-3-chloro-3-(4-chlorophenyl)propan-1-ol

Conditions

Conditions	Yield
With boron trifluoride at -78 - 20℃; Prins reaction;	84%

: 628-51-3
diacetoxymethane

: 13361-34-7
2'-ethylhexyl cyanoacetate

: 2-ethylhexyl α-cyanoacrylate

Conditions

Conditions	Yield
With piperazine; dodecylbenzene-sulphonic acid at 120 - 130℃; for 2h;	84%

: 628-51-3
diacetoxymethane

: 52688-08-1
2-octyl cyanoacetate

: 2-octyl α-cyanoacrylate

Conditions

Conditions	Yield
With N,N-dimethylmethyleneammonium ion; dodecylbenzene-sulphonic acid at 120 - 130℃; for 2h;	83%

: 292638-84-7
styrene

: 628-51-3
diacetoxymethane

: (+/-)-3-bromo-3-phenylpropan-1-ol

Conditions

Conditions	Yield
With boron trifluoride; tetrabutylammomium bromide at -78 - 20℃;	82%

: 628-51-3
diacetoxymethane

: 590-97-6
acetoxymethyl bromide

Conditions

Conditions	Yield
With trimethylsilyl bromide; zinc(II) chloride Ambient temperature;	81%

: 292638-84-7
styrene

: 628-51-3
diacetoxymethane

: 18775-64-9
(+/-)-3-chloro-3-phenylpropan-1-ol

Conditions

Conditions	Yield
With boron trifluoride at -78 - 20℃; Prins reaction;	79%

: 405-99-2
para-fluorostyrene

: 628-51-3
diacetoxymethane

: (+/-)-3-chloro-3-(4-fluorophenyl)propan-1-ol

Conditions

Conditions	Yield
With boron trifluoride at -78 - 20℃; Prins reaction;	79%

: 2039-82-9
1-bromo-4-ethenyl-benzene

: 628-51-3
diacetoxymethane

: 908260-10-6, 219745-24-1
(+/-)-3-chloro-3-(4-bromophenyl)propan-1-ol

Conditions

Conditions	Yield
With boron trifluoride at -78 - 20℃; Prins reaction;	79%

: 628-51-3
diacetoxymethane

: 350-51-6
3-fluorostyrene

: 3-chloro-3-(3-fluorophenyl)propan-1-ol

Conditions

Conditions	Yield
With boron trifluoride at -78 - 20℃; Prins reaction;	76%

: 622-97-9
1-ethenyl-4-methylbenzene

: 628-51-3
diacetoxymethane

: 219745-20-7
3-chloro-3-p-tolylpropan-1-ol

Conditions

Conditions	Yield
With boron trifluoride at -78 - 20℃; Prins reaction;	71%

: 628-51-3
diacetoxymethane

: 75750-46-8
cyanoacetic acid 6-(2-cyanoacetoxy)hexyl ester

: 1,6-hexanediol-bis(2-cyanoacrylate)

Conditions

Conditions	Yield
With 2,2'-dihydroxy-5,5'-dimethyl-3,3'-di-tert-burtyl-1,1'-diphenylmethane; dodecylbenzene-sulphonic acid; (RS)-2-methylpiperazine at 110℃; for 2h;	71%

: 628-51-3
diacetoxymethane

: 71888-58-9
cyanoacetic acid octadecyl ester

: octadecyl cyanoacrylate

Conditions

Conditions	Yield
With 1,3,5-trimethyl-1,3,5-triazacyclohexane; 2,6-di-tert-butyl-4-methyl-phenol; dodecylbenzene-sulphonic acid at 125℃;	70%

: 628-51-3
diacetoxymethane

: 644-33-7
N,N'-ethanediyl-bis-benzamide

: 49738-18-3
1,3-dibenzoyl-imidazolidine

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In acetic acid at 80℃; for 3h;	67%

: 628-51-3
diacetoxymethane

: cyanoacetoxymethyltrimethylsilane

: (α-cyanoacryloyloxymethyl)trimethylsilane

Conditions

Conditions	Yield
With dodecylbenzene-sulphonic acid; (RS)-2-methylpiperazine at 120 - 130℃; for 2h;	66%

: 628-51-3
diacetoxymethane

: 87057-52-1
2-But-3-enyl-2-(5-hydroxy-4-oxo-4H-pyran-2-ylmethyl)-malonic acid dimethyl ester

: 87057-59-8
(1R,6R,8S)-10-Acetoxy-9-oxo-12-oxa-tricyclo[6.3.1.01,6]dodec-10-ene-3,3-dicarboxylic acid dimethyl ester

Conditions

Conditions	Yield
at 110℃; for 48h;	65%

: 100-80-1
3-methylstyrene

: 628-51-3
diacetoxymethane

: 219745-19-4
3-chloro-3-m-tolylpropan-1-ol

Conditions

Conditions	Yield
With boron trifluoride at -78 - 20℃; Prins reaction;	63%

: 628-51-3
diacetoxymethane

: 2039-85-2
3-Chlorostyrene

: 3-chloro-3-(3-chlorophenyl)propan-1-ol

Conditions

Conditions	Yield
With boron trifluoride at -78 - 20℃; Prins reaction;	62%

: 628-51-3
diacetoxymethane

: 2039-86-3
3-bromostyrene

: 3-(3-bromophenyl)-3-chloropropan-1-ol

Conditions

Conditions	Yield
With boron trifluoride at -78 - 20℃; Prins reaction;	59%

: 628-51-3
diacetoxymethane

: 2039-88-5
2-bromostyrene

: (+/-)-3-chloro-3-(2-bromophenyl)propan-1-ol

Conditions

Conditions	Yield
With boron trifluoride at -78 - 20℃; Prins reaction;	47%

: 628-51-3
diacetoxymethane

: 394-46-7
2-fluorostyrene

: (+/-)-3-chloro-3-(2-fluorophenyl)propan-1-ol

Conditions

Conditions	Yield
With boron trifluoride at -78 - 20℃; Prins reaction;	45%

: 628-51-3
diacetoxymethane

: 2039-87-4
2-chlorostyrene

: 3-chloro-3-(2-chlorophenyl)propan-1-ol

Conditions

Conditions	Yield
With boron trifluoride at -78 - 20℃; Prins reaction;	44%

Methylene Diacetate Specification

The Methylene Diacetate is an organic compound with the formula C₅H₈O₄. The IUPAC name of this chemical is Acetyloxymethyl acetate. With the CAS registry number 628-51-3, it is also named as Diacetoxymethane. Besides, its molecular weight is 132.11462.

Physical properties about Methylene Diacetate are: (1)ACD/LogP: -0.308; (2)ACD/LogD (pH 5.5): -0.31; (3)ACD/LogD (pH 7.4): -0.31; (4)ACD/BCF (pH 5.5): 1.00; (5)ACD/BCF (pH 7.4): 1.00; (6)ACD/KOC (pH 5.5): 16.19; (7)ACD/KOC (pH 7.4): 16.19; (8)#H bond acceptors: 4; (9)#Freely Rotating Bonds: 4; (10)Index of Refraction: 1.402; (11)Molar Refractivity: 28.763 cm³; (12)Molar Volume: 118.034 cm³; (13)Polarizability: 11.403 10-24cm³; (14)Surface Tension: 31.9130001068115 dyne/cm; (15)Density: 1.119 g/cm³; (16)Flash Point: 72.624 °C; (17)Enthalpy of Vaporization: 40.102 kJ/mol; (18)Boiling Point: 164.499 °C at 760 mmHg; (19)Vapour Pressure: 1.96099996566772 mmHg at 25°C

Preparation of Methylene Diacetate: This chemical can be prepared by But-2-yne and Formaldehyde. This reaction will need reagent O₃ and solvent CH₂Cl₂. The reaction temperature of -100 °C. The yield is about 7%.

Methanediol,1,1-diacetate can be obtained by But-2-yne and Formaldehyde

Uses of Methylene Diacetate: It can be used to produce Acetoxy-bromo-methane. It will need reagents ZnCl₂; (CH₃)₃SiBr. The yield is about 81%.

Methanediol,1,1-diacetate can be used to produce Acetoxy-bromo-methane

You can still convert the following datas into molecular structure:
(1)InChI=1S/C5H8O4/c1-4(6)8-3-9-5(2)7/h3H2,1-2H3;
(2)InChIKey=BPGDAMSIGCZZLK-UHFFFAOYSA-N;
(3)SmilesC(OCOC(C)=O)(C)=O;

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intravenous	178mg/kg (178mg/kg)		U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#00030,

Product Name

METHYLENE DIACETATE, 99

Synthetic route

Methylene Diacetate Specification

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