Product Name

  • Name

    1,5-Pentanediol diacrylate

  • EINECS 253-235-8
  • CAS No. 36840-85-4
  • Article Data11
  • CAS DataBase
  • Density 1.024 g/cm3
  • Solubility
  • Melting Point
  • Formula C11H16O4
  • Boiling Point 285.1 °C at 760 mmHg
  • Molecular Weight 212.246
  • Flash Point 134.4 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 36840-85-4 (1,5-Pentanediol diacrylate)
  • Hazard Symbols
  • Synonyms 2-Propenoicacid, 1,5-pentanediyl ester (9CI);1,5-Pentamethylene diacrylate;Pentamethylene diacrylate;CCRIS 7043;AC1L3PPD;AC1Q67HL;KST-1B3820;CID93195;
  • PSA 52.60000
  • LogP 1.61510

Synthetic route

3-Bromopropionic acid
590-92-1

3-Bromopropionic acid

1 ,5-pentanediol
111-29-5

1 ,5-pentanediol

pentamethylene 1,5-diacrylate
36840-85-4

pentamethylene 1,5-diacrylate

Conditions
ConditionsYield
With triethylamine In toluene75%
1 ,5-pentanediol
111-29-5

1 ,5-pentanediol

acryloyl chloride
814-68-6

acryloyl chloride

pentamethylene 1,5-diacrylate
36840-85-4

pentamethylene 1,5-diacrylate

Conditions
ConditionsYield
With triethylamine; 2-hydroxyresorcinol In benzene at 50℃; for 0.5h;61%
With triethylamine In dichloromethane at 0 - 20℃; for 6h; Inert atmosphere;
With triethylamine In dichloromethane at 20℃; Cooling with ice;
pentane-1,5-diyl bis(3-bromopropionate)
53219-90-2

pentane-1,5-diyl bis(3-bromopropionate)

pentamethylene 1,5-diacrylate
36840-85-4

pentamethylene 1,5-diacrylate

Conditions
ConditionsYield
With triethylamine; hydroquinone In benzene Heating;
cisatracurium benzenesulfonate

cisatracurium benzenesulfonate

A

pentamethylene 1,5-diacrylate
36840-85-4

pentamethylene 1,5-diacrylate

B

(R)-laudanosine
85-63-2

(R)-laudanosine

Conditions
ConditionsYield
In phosphate buffer at 37℃; pH=7.4; Kinetics; Further Variations:; pH-values; Elimination; Hofmann;
1 ,5-pentanediol
111-29-5

1 ,5-pentanediol

pentamethylene 1,5-diacrylate
36840-85-4

pentamethylene 1,5-diacrylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: Et3N, benzene-1,4-diol / benzene / Heating
View Scheme
1 ,5-pentanediol
111-29-5

1 ,5-pentanediol

acrylic acid methyl ester
292638-85-8

acrylic acid methyl ester

A

pentamethylene 1,5-diacrylate
36840-85-4

pentamethylene 1,5-diacrylate

B

hydroxypentyl acrylate
57198-94-4

hydroxypentyl acrylate

Conditions
ConditionsYield
With Novozyme 435 In tert-Amyl alcohol at 50℃; for 120h; Inert atmosphere; Molecular sieve; Enzymatic reaction;
...Expand
1 ,5-pentanediol
111-29-5

1 ,5-pentanediol

acrylic acid methyl ester
292638-85-8

acrylic acid methyl ester

pentamethylene 1,5-diacrylate
36840-85-4

pentamethylene 1,5-diacrylate

Conditions
ConditionsYield
toluene-4-sulfonic acid at 90 - 100℃; Inert atmosphere;
pentamethylene 1,5-diacrylate
36840-85-4

pentamethylene 1,5-diacrylate

(R)-tetrahydropapaverine N-acetyl-L-leucine salt

(R)-tetrahydropapaverine N-acetyl-L-leucine salt

oxalic acid
144-62-7

oxalic acid

C53H72N2O12(2+)*C2O4(2-)

C53H72N2O12(2+)*C2O4(2-)

Conditions
ConditionsYield
Stage #1: pentamethylene 1,5-diacrylate; (R)-tetrahydropapaverine N-acetyl-L-leucine salt With acetic acid; sodium hydroxide In water; toluene at 55 - 70℃; for 4h; pH=10;
Stage #2: oxalic acid In acetone		85.1%
...Expand
pentamethylene 1,5-diacrylate
36840-85-4

pentamethylene 1,5-diacrylate

Ethyl nipecotate
71962-74-8

Ethyl nipecotate

N,N-4,10-dioxa-3,11-dioxotridecylene-1,13-diyl-bis(3-ethoxycarbonylpiperidine)
145487-64-5

N,N-4,10-dioxa-3,11-dioxotridecylene-1,13-diyl-bis(3-ethoxycarbonylpiperidine)

Conditions
ConditionsYield
With acetic acid at 70℃; for 16.5h;84%
pentamethylene 1,5-diacrylate
36840-85-4

pentamethylene 1,5-diacrylate

oxalic acid
144-62-7

oxalic acid

(-) N-norlaudanosine
50896-90-7

(-) N-norlaudanosine

C51H66N2O12*2C2H2O4

C51H66N2O12*2C2H2O4

Conditions
ConditionsYield
Stage #1: (-) N-norlaudanosine With sodium hydroxide In water; toluene at 55℃; pH=10;
Stage #2: pentamethylene 1,5-diacrylate With acetic acid In water; toluene at 70℃; for 4h;
Stage #3: oxalic acid In acetone		80.4%
...Expand
morpholine
110-91-8

morpholine

pentamethylene 1,5-diacrylate
36840-85-4

pentamethylene 1,5-diacrylate

N,N-4,10-dioxa-3,11-dioxotridecylene-1,13-diyl-bis-morpholine
145487-62-3

N,N-4,10-dioxa-3,11-dioxotridecylene-1,13-diyl-bis-morpholine

Conditions
ConditionsYield
With acetic acid at 70℃; for 16.5h;80%
piperidine
110-89-4

piperidine

pentamethylene 1,5-diacrylate
36840-85-4

pentamethylene 1,5-diacrylate

N,N-4,10-dioxa-3,11-dioxotridecylene-1,13-diyl-bis-piperidine
145487-58-7

N,N-4,10-dioxa-3,11-dioxotridecylene-1,13-diyl-bis-piperidine

Conditions
ConditionsYield
With acetic acid at 70℃; for 16.5h;79%
hexamethylene imine
111-49-9

hexamethylene imine

pentamethylene 1,5-diacrylate
36840-85-4

pentamethylene 1,5-diacrylate

N,N-4,10-dioxa-3,11-dioxotridecylene-1,13-diyl-bis-homopiperidine
145487-60-1

N,N-4,10-dioxa-3,11-dioxotridecylene-1,13-diyl-bis-homopiperidine

Conditions
ConditionsYield
With acetic acid at 70℃; for 16.5h;75%
3-hydroxypiperazine
6859-99-0

3-hydroxypiperazine

pentamethylene 1,5-diacrylate
36840-85-4

pentamethylene 1,5-diacrylate

N,N-4,10-dioxa-3,11-dioxotridecylene-1,13-diyl-bis(3-hydroxypiperidine)
145487-74-7

N,N-4,10-dioxa-3,11-dioxotridecylene-1,13-diyl-bis(3-hydroxypiperidine)

Conditions
ConditionsYield
With acetic acid at 70℃; for 16.5h;72%
methyl 2-bromo-2-deoxy-3,4,5,7-tetra-O-benzyl-α-D-arabino-hept-2-enoseptanoside
946416-33-7

methyl 2-bromo-2-deoxy-3,4,5,7-tetra-O-benzyl-α-D-arabino-hept-2-enoseptanoside

pentamethylene 1,5-diacrylate
36840-85-4

pentamethylene 1,5-diacrylate

methyl 2-deoxy-2-C-(3-((5-(acryloyloxy)pentyl)oxy)-3-oxoprop-1-en-1-yl)-3,4,5,7-tetra-O-benzyl-α-D-arabino-hept-2-enoseptanoside

methyl 2-deoxy-2-C-(3-((5-(acryloyloxy)pentyl)oxy)-3-oxoprop-1-en-1-yl)-3,4,5,7-tetra-O-benzyl-α-D-arabino-hept-2-enoseptanoside

Conditions
ConditionsYield
With palladium diacetate; caesium carbonate In 1,4-dioxane at 98℃; for 72h; Heck reaction; Inert atmosphere;60%
pentamethylene 1,5-diacrylate
36840-85-4

pentamethylene 1,5-diacrylate

A

Oxirane-2-carboxylic acid 5-acryloyloxy-pentyl ester

Oxirane-2-carboxylic acid 5-acryloyloxy-pentyl ester

B

1,2,12,13-diepoxy-4,10-dioxa-3,11-dioxotridecane
145487-77-0

1,2,12,13-diepoxy-4,10-dioxa-3,11-dioxotridecane

Conditions
ConditionsYield
With disodium hydrogenphosphate; dihydrogen peroxide; trifluoroacetic anhydride In dichloromethane at 42℃; for 3h; Yield given;A n/a
B 55%
With disodium hydrogenphosphate; dihydrogen peroxide; trifluoroacetic anhydride In dichloromethane at 42℃; for 3h;A n/a
B 55%
1,2,3,4-tetrahydro-6,7-dimethoxy-1<2-(3,4-dimethoxyphenyl)ethyl>isoquinoline
65899-28-7

1,2,3,4-tetrahydro-6,7-dimethoxy-1<2-(3,4-dimethoxyphenyl)ethyl>isoquinoline

pentamethylene 1,5-diacrylate
36840-85-4

pentamethylene 1,5-diacrylate

1,13-bis-<1,2,3,4-tetrahydro-6,7-dimethoxy-1-<2-(3,4-dimethoxyphenyl)ethyl>-isoquinolin-2-yl>-4,10-dioxa-3,11-dioxotridecane dioxalate
81182-05-0

1,13-bis-<1,2,3,4-tetrahydro-6,7-dimethoxy-1-<2-(3,4-dimethoxyphenyl)ethyl>-isoquinolin-2-yl>-4,10-dioxa-3,11-dioxotridecane dioxalate

Conditions
ConditionsYield
In benzene for 48h; Heating;53%
pentamethylene 1,5-diacrylate
36840-85-4

pentamethylene 1,5-diacrylate

1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride
6429-04-5

1,2,3,4-tetrahydro-1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline hydrochloride

pentamethylene bis(1-(3,4-dimethoxybenzyl)-3,4-dihydro-6,7-dimethoxy-1H-isoquinoline-2-propionate) dioxalate
64228-78-0, 64493-10-3, 83285-74-9, 96687-52-4, 96687-53-5, 110817-20-4

pentamethylene bis(1-(3,4-dimethoxybenzyl)-3,4-dihydro-6,7-dimethoxy-1H-isoquinoline-2-propionate) dioxalate

Conditions
ConditionsYield
In benzene for 48h; Heating;51%
pentamethylene 1,5-diacrylate
36840-85-4

pentamethylene 1,5-diacrylate

5-[(3,4-dimethoxyphenyl)methyl]-5,6,7,8-tetrahydro-1,3-dioxolo[4,5-g]isoquinoline
19918-74-2

5-[(3,4-dimethoxyphenyl)methyl]-5,6,7,8-tetrahydro-1,3-dioxolo[4,5-g]isoquinoline

3-[5-(3,4-Dimethoxy-benzyl)-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-6-yl]-propionic acid 5-{3-[5-(3,4-dimethoxy-benzyl)-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-6-yl]-propionyloxy}-pentyl ester; compound with oxalic acid
81165-50-6

3-[5-(3,4-Dimethoxy-benzyl)-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-6-yl]-propionic acid 5-{3-[5-(3,4-dimethoxy-benzyl)-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-6-yl]-propionyloxy}-pentyl ester; compound with oxalic acid

Conditions
ConditionsYield
In benzene for 48h; Heating;39%
pentamethylene 1,5-diacrylate
36840-85-4

pentamethylene 1,5-diacrylate

ethyl pipecolate
15862-72-3

ethyl pipecolate

N,N-4,10-dioxa-3,11-dioxotridecylene-1,13-diyl-bis(2-ethoxycarbonylpiperidine)
145487-71-4

N,N-4,10-dioxa-3,11-dioxotridecylene-1,13-diyl-bis(2-ethoxycarbonylpiperidine)

Conditions
ConditionsYield
With acetic acid at 70℃; for 16.5h;34%
pentamethylene 1,5-diacrylate
36840-85-4

pentamethylene 1,5-diacrylate

2.6-dimethylpiperidine
504-03-0

2.6-dimethylpiperidine

N,N-4,10-dioxa-3,11-dioxotridecylene-1,13-diyl-bis-2,6-dimethylpiperidine

N,N-4,10-dioxa-3,11-dioxotridecylene-1,13-diyl-bis-2,6-dimethylpiperidine

Conditions
ConditionsYield
With acetic acid at 70℃; for 16.5h;12%
pentamethylene 1,5-diacrylate
36840-85-4

pentamethylene 1,5-diacrylate

phlomisoic acid methyl ester
1122507-27-0

phlomisoic acid methyl ester

C32H44O7
1515848-83-5

C32H44O7

Conditions
ConditionsYield
With oxygen; copper diacetate; palladium diacetate; p-benzoquinone In diethyl ether; propionic acid at 40℃; for 80h; stereoselective reaction;10%
pentamethylene 1,5-diacrylate
36840-85-4

pentamethylene 1,5-diacrylate

piperidin-2-ylmethanol
3433-37-2

piperidin-2-ylmethanol

N,N-4,10-dioxa-3,11-dioxotridecylene-1,13-diyl-bis(2-hydroxymethylpiperidine)

N,N-4,10-dioxa-3,11-dioxotridecylene-1,13-diyl-bis(2-hydroxymethylpiperidine)

Conditions
ConditionsYield
With acetic acid at 70℃; for 16.5h;
pentamethylene 1,5-diacrylate
36840-85-4

pentamethylene 1,5-diacrylate

S-(-)-Norlaudanosine
4747-98-2

S-(-)-Norlaudanosine

(S)-(+)-1-tetrahydropapaverin-2'-yl-4,10-dioxa-3,11-dioxotridec-12-ene
96648-37-2

(S)-(+)-1-tetrahydropapaverin-2'-yl-4,10-dioxa-3,11-dioxotridec-12-ene

Conditions
ConditionsYield
With acetic acid at 70℃; for 4h;71 % Chromat.
pentamethylene 1,5-diacrylate
36840-85-4

pentamethylene 1,5-diacrylate

S-(-)-Norlaudanosine
4747-98-2

S-(-)-Norlaudanosine

N,N'-4,10-dioxa-3,11-dioxotridecylene-1,13-diyl-bis-(S)-(+)-tetrahydropapaverine
64228-85-9

N,N'-4,10-dioxa-3,11-dioxotridecylene-1,13-diyl-bis-(S)-(+)-tetrahydropapaverine

Conditions
ConditionsYield
With acetic acid at 70℃; Yield given;
pentamethylene 1,5-diacrylate
36840-85-4

pentamethylene 1,5-diacrylate

(-) N-norlaudanosine
50896-90-7

(-) N-norlaudanosine

N,N'-4,10-dioxa-3,11-dioxotridecylene-1,13-diyl-bis-(R)-(-)-tetrahydropapaverine
64228-84-8

N,N'-4,10-dioxa-3,11-dioxotridecylene-1,13-diyl-bis-(R)-(-)-tetrahydropapaverine

Conditions
ConditionsYield
With acetic acid at 70℃; for 4h; Yield given;
pentamethylene 1,5-diacrylate
36840-85-4

pentamethylene 1,5-diacrylate

(RS)/meso-N,N'-4,10-dioxa-3,11-dioxotridecylene-1,13-diyl-bis-tetrahydropapaverine
64493-09-0

(RS)/meso-N,N'-4,10-dioxa-3,11-dioxotridecylene-1,13-diyl-bis-tetrahydropapaverine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 71 percent Chromat. / glacial acetic acid / 4 h / 70 °C
2: benzene / Heating
View Scheme
pentamethylene 1,5-diacrylate
36840-85-4

pentamethylene 1,5-diacrylate

C51H64N2O12(2+)*2I(1-)
64229-27-2

C51H64N2O12(2+)*2I(1-)

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 39 percent / benzene / 48 h / Heating
2: 80 percent / acetonitrile / 48 h / Ambient temperature
View Scheme
pentamethylene 1,5-diacrylate
36840-85-4

pentamethylene 1,5-diacrylate

C65H70Cl4N2O16
145487-93-0

C65H70Cl4N2O16

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 55 percent / 85percent H2O2, trifluoroacetic anhydride, Na2HPO4 / CH2Cl2 / 3 h / 42 °C
2: 81 percent / propan-2-ol / 48 h / 50 °C
3: 72 percent / CHCl3 / 17 h / 50 °C
View Scheme
pentamethylene 1,5-diacrylate
36840-85-4

pentamethylene 1,5-diacrylate

C65H70Cl4N2O16
145487-92-9

C65H70Cl4N2O16

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 55 percent / 85percent H2O2, trifluoroacetic anhydride, Na2HPO4 / CH2Cl2 / 3 h / 42 °C
2: 81 percent / propan-2-ol / 48 h / 50 °C
3: 52 percent / CHCl3 / 17 h / 50 °C
View Scheme
pentamethylene 1,5-diacrylate
36840-85-4

pentamethylene 1,5-diacrylate

C67H72F6N2O16
145487-95-2

C67H72F6N2O16

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 55 percent / 85percent H2O2, trifluoroacetic anhydride, Na2HPO4 / CH2Cl2 / 3 h / 42 °C
2: 81 percent / propan-2-ol / 48 h / 50 °C
3: 71 percent / CHCl3 / 17 h / 50 °C
View Scheme
pentamethylene 1,5-diacrylate
36840-85-4

pentamethylene 1,5-diacrylate

C71H86N2O20
145487-91-8

C71H86N2O20

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 55 percent / 85percent H2O2, trifluoroacetic anhydride, Na2HPO4 / CH2Cl2 / 3 h / 42 °C
2: 81 percent / propan-2-ol / 48 h / 50 °C
3: 80 percent / CHCl3 / 17 h / 50 °C
View Scheme

1,5-Pentanediol diacrylate Specification

The 1,5-Pentanediol diacrylate with CAS registry number of 36840-85-4 is also known as Pentamethylene diacrylate. The IUPAC name is 5-Prop-2-enoyloxypentyl prop-2-enoate. It belongs to product categories of Monomer. Its EINECS registry number is 253-235-8. In addition, the formula is C11H16O4 and the molecular weight is 212.24.

Physical properties about 1,5-Pentanediol diacrylate are: (1)ACD/LogP: 2.43; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.43; (4)ACD/LogD (pH 7.4): 2.43; (5)ACD/BCF (pH 5.5): 41.04; (6)ACD/BCF (pH 7.4): 41.04; (7)ACD/KOC (pH 5.5): 496.97; (8)ACD/KOC (pH 7.4): 496.97; (9)#H bond acceptors: 4; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 10; (12)Index of Refraction: 1.452; (13)Molar Refractivity: 56.01 cm3; (14)Molar Volume: 207.2 cm3; (15)Surface Tension: 33.1 dyne/cm; (16)Density: 1.024 g/cm3; (17)Flash Point: 134.4 °C; (18)Enthalpy of Vaporization: 52.42 kJ/mol; (19)Boiling Point: 285.1 °C at 760 mmHg; (20)Vapour Pressure: 0.00285 mmHg at 25 °C.

Preparation of 1,5-Pentanediol diacrylate: it is prepared by reaction of acryloyl chloride with pentane-1,5-diol. The reaction needs reagent triethylamine, pyrogallol and solvent benzene at the temperature of 50 °C for 30 minutes. The yield is about 61%.

1,5-Pentanediol diacrylate is prepared by reaction of acryloyl chloride with pentane-1,5-diol.

Uses of 1,5-Pentanediol diacrylate: it is used to produce 3-piperidin-1-yl-propionic acid 5-(3-piperidin-1-yl-propionyloxy)-pentyl ester by reaction with piperidine. The reaction occurs with reagent glacial acetic acid at 70 °C for 16.5 hours. The yield is about 79%.

1,5-Pentanediol diacrylate is used to produce 3-piperidin-1-yl-propionic acid 5-(3-piperidin-1-yl-propionyloxy)-pentyl ester by reaction with piperidine.

You can still convert the following datas into molecular structure:
1. Canonical SMILES: C=CC(=O)OCCCCCOC(=O)C=C
2. InChI: InChI=1S/C11H16O4/c1-3-10(12)14-8-6-5-7-9-15-11(13)4-2/h3-4H,1-2,5-9H2
3. InChIKey: XAMCLRBWHRRBCN-UHFFFAOYSA-N

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