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814-68-6

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814-68-6 Usage

Chemical Properties

Acryloyl chloride is a highly flammable, polymerizable, and toxic (inhalation), light yellow liquid. A lacrimator.

Uses

Acryloyl chloride is used in the production of plastics. It plays an important role in the preparation of acrylate monomers and polymers. It also acts as a substrate for cross-metathesis. Further, it is utilized in organic synthesis for the introduction of acrylic groups into other compounds.

General Description

A liquid. Boiling point 75°C. Used to make plastics. Polymerization in a closed container can cause pressurization and explosive rupture.

Air & Water Reactions

Polymerizes readily upon exposure to oxygen in the air. Reacts exothermically with water to give hydrochloric acid and acrylic acid.

Reactivity Profile

Acrylyl chloride is incompatible with strong oxidizing agents, alcohols, amines, alkali. Polymerizes readily upon exposure to oxygen. May react vigorously or explosively if mixed with diisopropyl ether or other ethers in the presence of trace amounts of metal salts [J. Haz. Mat., 1981, 4, 291].

Fire Hazard

When heated to decomposition, Acrylyl chloride emits toxic fumes of chlorides. Decomposes in water.

Potential Exposure

May be used as a monomer in preparation of specialty polymers or as a chemical intermediate

Shipping

UN3383 Poisonous Toxic by inhalation liquid, flammable, n.o.s. with an LC50 # 200 mL/m3 and saturated vapor concentration ≥500 LC50, Hazard class: 6.1; Labels: 6.1-Poisonous materials, 3-Flammable liquid, Technical Name Required, Inhalation Hazard Zone A. UN2924 Flammable liquids, corrosive, n.o.s., Hazard Class: 3; Labels: 3-Flammable liquid, 8-Corrosive material, Technical Name Required

Incompatibilities

Use MEHQ (monomethyl ether of hydroquinone) as an inhibitor. Incompatible with oxidizers, polymerizes on contact with oxygen; alcohols, amines, alkalis. Reacts violently with water, releasing hydrochloric acid and acrylic acid. Attacks some metals.

Check Digit Verification of cas no

The CAS Registry Mumber 814-68-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 8,1 and 4 respectively; the second part has 2 digits, 6 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 814-68:
(5*8)+(4*1)+(3*4)+(2*6)+(1*8)=76
76 % 10 = 6
So 814-68-6 is a valid CAS Registry Number.
InChI:InChI=1/C3H3ClO/c1-2-3(4)5/h2H,1H2

814-68-6 Well-known Company Product Price

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  • Alfa Aesar

  • (L10363)  Acryloyl chloride, 96%, stab. with 400ppm phenothiazine   

  • 814-68-6

  • 10g

  • 186.0CNY

  • Detail
  • Alfa Aesar

  • (L10363)  Acryloyl chloride, 96%, stab. with 400ppm phenothiazine   

  • 814-68-6

  • 50g

  • 289.0CNY

  • Detail
  • Alfa Aesar

  • (L10363)  Acryloyl chloride, 96%, stab. with 400ppm phenothiazine   

  • 814-68-6

  • 250g

  • 1063.0CNY

  • Detail

814-68-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name Acrylyl chloride

1.2 Other means of identification

Product number -
Other names 2-Propenoyl chloride

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:814-68-6 SDS

814-68-6Synthetic route

acrylic acid
79-10-7

acrylic acid

acryloyl chloride
814-68-6

acryloyl chloride

Conditions
ConditionsYield
With thionyl chloride In N,N-dimethyl-formamide at 20℃; for 0.0833333h; Reagent/catalyst; Temperature;100%
With thionyl chloride98%
With oxalyl dichloride; N,N-dimethyl-formamide at 20 - 40℃; for 0.166667h; Product distribution / selectivity;96.2%
acrylic acid
79-10-7

acrylic acid

A

acryloyl chloride
814-68-6

acryloyl chloride

B

2-chloropropionyl chloride
625-36-5

2-chloropropionyl chloride

Conditions
ConditionsYield
With thionyl chloride In N,N-dimethyl-formamide at 80℃; under 2068.65 Torr; for 0.416667h; Reagent/catalyst; Pressure;A 4%
B 94%
With trichlorophosphate In N,N-dimethyl-formamide at 80℃; for 0.00833333h; Reagent/catalyst; Temperature;A 91%
B 6%
With thionyl chloride; N,N-dimethyl-formamide In neat (no solvent) at 60℃; for 0.0166667h; Catalytic behavior; Reagent/catalyst; Temperature; Time; Flow reactor;
3-Bromopropionyl chloride
15486-96-1

3-Bromopropionyl chloride

acryloyl chloride
814-68-6

acryloyl chloride

Conditions
ConditionsYield
With P(MeNCH2CH2)3N In acetonitrile at 25℃; for 0.0833333h;90%
ethyl vinyl ether
109-92-2

ethyl vinyl ether

acryloyl chloride
814-68-6

acryloyl chloride

Conditions
ConditionsYield
Stage #1: ethyl vinyl ether With oxalyl dichloride at 0 - 20℃; for 1h; Inert atmosphere;
Stage #2: at 120℃; for 0.5h; Inert atmosphere;
89%
acrylic acid
79-10-7

acrylic acid

A

C6H7ClO3

C6H7ClO3

B

acryloyl chloride
814-68-6

acryloyl chloride

C

2-chloropropionyl chloride
625-36-5

2-chloropropionyl chloride

Conditions
ConditionsYield
With thionyl chloride In N,N-dimethyl-formamide at 60℃; for 0.0166667h; Reagent/catalyst;A 7%
B 82%
C 11%
phosgene
75-44-5

phosgene

acrylic acid
79-10-7

acrylic acid

acryloyl chloride
814-68-6

acryloyl chloride

Conditions
ConditionsYield
64%
sodium 2-propenoate
7446-81-3

sodium 2-propenoate

acryloyl chloride
814-68-6

acryloyl chloride

Conditions
ConditionsYield
With trichlorophosphate
benzoyl chloride
98-88-4

benzoyl chloride

acrylic acid
79-10-7

acrylic acid

acryloyl chloride
814-68-6

acryloyl chloride

2-chloropropionyl chloride
625-36-5

2-chloropropionyl chloride

acryloyl chloride
814-68-6

acryloyl chloride

Conditions
ConditionsYield
With barium(II) chloride at 180℃;
With fired clay fragments at 140 - 170℃;
With tripentylamine at 80 - 140℃;
With fired clay fragments at 140 - 170℃;
With barium(II) chloride at 180℃;
acrolein
107-02-8

acrolein

acryloyl chloride
814-68-6

acryloyl chloride

Conditions
ConditionsYield
With chlorine at 285 - 320℃;
2-chloropropionyl chloride
625-36-5

2-chloropropionyl chloride

A

chloroethylene
75-01-4

chloroethylene

B

carbon monoxide
201230-82-2

carbon monoxide

C

acryloyl chloride
814-68-6

acryloyl chloride

D

3-chloro-1,2-propenone
204848-50-0

3-chloro-1,2-propenone

E

acetylene
74-86-2

acetylene

Conditions
ConditionsYield
In solid matrix Mechanism; Irradiation;
2-chloropropionyl chloride
625-36-5

2-chloropropionyl chloride

A

chloroethylene
75-01-4

chloroethylene

B

carbon monoxide
201230-82-2

carbon monoxide

C

acryloyl chloride
814-68-6

acryloyl chloride

D

3-Chloro-propen-1-one; hydrochloride

3-Chloro-propen-1-one; hydrochloride

E

acetylene
74-86-2

acetylene

Conditions
ConditionsYield
In solid matrix at -263.2℃; Mechanism; Irradiation;
2-chloropropionyl chloride
625-36-5

2-chloropropionyl chloride

A

chloroethylene
75-01-4

chloroethylene

B

acryloyl chloride
814-68-6

acryloyl chloride

C

3-Chloro-propen-1-one; hydrochloride

3-Chloro-propen-1-one; hydrochloride

D

acetylene
74-86-2

acetylene

Conditions
ConditionsYield
In solid matrix at -263.2℃; Irradiation;
acrylacidic sodium

acrylacidic sodium

acryloyl chloride
814-68-6

acryloyl chloride

Conditions
ConditionsYield
With trichlorophosphate
2-chloropropionyl chloride
625-36-5

2-chloropropionyl chloride

Al2O3

Al2O3

acryloyl chloride
814-68-6

acryloyl chloride

Conditions
ConditionsYield
at 140 - 300℃; durch Leiten des Dampfes;
at 140 - 300℃; durch Leiten des Dampfes;
2-chloropropionyl chloride
625-36-5

2-chloropropionyl chloride

BaCl2

BaCl2

acryloyl chloride
814-68-6

acryloyl chloride

Conditions
ConditionsYield
at 140 - 300℃; durch Leiten des Dampfes;
at 140 - 300℃; durch Leiten des Dampfes;
acrylic acid
79-10-7

acrylic acid

A

acryloyl chloride
814-68-6

acryloyl chloride

B

HCl

HCl

Conditions
ConditionsYield
With phosphorus pentachloride; hydroquinone
diadamantyl 1,1,3-trimethyl-1,3-acetonedicarboxylate
337967-18-7

diadamantyl 1,1,3-trimethyl-1,3-acetonedicarboxylate

A

adamantan-1-yl propionate
37818-91-0

adamantan-1-yl propionate

B

acryloyl chloride
814-68-6

acryloyl chloride

C

1-adamantyl isobutyrate

1-adamantyl isobutyrate

D

diadamantyl 2,2,3,3-tetramethyl-succinate

diadamantyl 2,2,3,3-tetramethyl-succinate

Conditions
ConditionsYield
In benzene for 4h; Product distribution; Further Variations:; in solvent or solid state; Photolysis;
1H-imidazole
288-32-4

1H-imidazole

ethyl acetate n-hexane

ethyl acetate n-hexane

3-(2-nitro-4-methoxyphenyl)acrylic acid chloride
1416226-15-7

3-(2-nitro-4-methoxyphenyl)acrylic acid chloride

acryloyl chloride
814-68-6

acryloyl chloride

Conditions
ConditionsYield
With hydrogenchloride; triethylamine In water
1H-imidazole
288-32-4

1H-imidazole

ethyl acetate n-hexane

ethyl acetate n-hexane

3-(3-nitro-4-methoxyphenyl)acrylic acid chloride
1416226-16-8

3-(3-nitro-4-methoxyphenyl)acrylic acid chloride

acryloyl chloride
814-68-6

acryloyl chloride

Conditions
ConditionsYield
With hydrogenchloride; triethylamine In water
1H-imidazole
288-32-4

1H-imidazole

ethyl acetate n-hexane

ethyl acetate n-hexane

2-methyl-3-(2-nitro-4-methoxyphenyl)acrylic acid chloride
1416226-17-9

2-methyl-3-(2-nitro-4-methoxyphenyl)acrylic acid chloride

acryloyl chloride
814-68-6

acryloyl chloride

Conditions
ConditionsYield
With hydrogenchloride; triethylamine In water
1H-imidazole
288-32-4

1H-imidazole

ethyl acetate n-hexane

ethyl acetate n-hexane

2-methyl-3-(3-nitro-4-methoxyphenyl)acrylic acid chloride
1416226-18-0

2-methyl-3-(3-nitro-4-methoxyphenyl)acrylic acid chloride

acryloyl chloride
814-68-6

acryloyl chloride

Conditions
ConditionsYield
With hydrogenchloride; triethylamine In water
1H-imidazole
288-32-4

1H-imidazole

ethyl acetate n-hexane

ethyl acetate n-hexane

2-methyl-3-(4-methoxyphenyl)acrylic acid chloride
109830-34-4

2-methyl-3-(4-methoxyphenyl)acrylic acid chloride

acryloyl chloride
814-68-6

acryloyl chloride

Conditions
ConditionsYield
With hydrogenchloride; triethylamine In water
1H-imidazole
288-32-4

1H-imidazole

ethyl acetate n-hexane

ethyl acetate n-hexane

p-methoxycinnamoyl chloride
42996-84-9, 34446-64-5

p-methoxycinnamoyl chloride

acryloyl chloride
814-68-6

acryloyl chloride

Conditions
ConditionsYield
With hydrogenchloride; triethylamine In water
morpholine
110-91-8

morpholine

ethyl acetate n-hexane

ethyl acetate n-hexane

p-methoxycinnamoyl chloride
42996-84-9, 34446-64-5

p-methoxycinnamoyl chloride

acryloyl chloride
814-68-6

acryloyl chloride

Conditions
ConditionsYield
With hydrogenchloride; triethylamine In water
piperidine
110-89-4

piperidine

ethyl acetate n-hexane

ethyl acetate n-hexane

3-(2-nitro-4-methoxyphenyl)acrylic acid chloride
1416226-15-7

3-(2-nitro-4-methoxyphenyl)acrylic acid chloride

acryloyl chloride
814-68-6

acryloyl chloride

Conditions
ConditionsYield
With hydrogenchloride; triethylamine In water
ethyl acetate n-hexane

ethyl acetate n-hexane

3-(2-nitro-4-methoxyphenyl)acrylic acid chloride
1416226-15-7

3-(2-nitro-4-methoxyphenyl)acrylic acid chloride

diethylamine
109-89-7

diethylamine

acryloyl chloride
814-68-6

acryloyl chloride

Conditions
ConditionsYield
With hydrogenchloride; triethylamine In water
piperidine
110-89-4

piperidine

ethyl acetate n-hexane

ethyl acetate n-hexane

3-(3-nitro-4-methoxyphenyl)acrylic acid chloride
1416226-16-8

3-(3-nitro-4-methoxyphenyl)acrylic acid chloride

acryloyl chloride
814-68-6

acryloyl chloride

Conditions
ConditionsYield
With hydrogenchloride; triethylamine In water
bis((furan-2-yl)methyl)amine
18240-50-1

bis((furan-2-yl)methyl)amine

acryloyl chloride
814-68-6

acryloyl chloride

N,N-bis(2-furanylmethyl)propenamide
121328-25-4

N,N-bis(2-furanylmethyl)propenamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at -78 - 25℃;100%
Stanolone
521-18-6

Stanolone

acryloyl chloride
814-68-6

acryloyl chloride

Acrylic acid (5S,8R,9S,10S,13S,14S,17S)-10,13-dimethyl-3-oxo-hexadecahydro-cyclopenta[a]phenanthren-17-yl ester
27953-69-1

Acrylic acid (5S,8R,9S,10S,13S,14S,17S)-10,13-dimethyl-3-oxo-hexadecahydro-cyclopenta[a]phenanthren-17-yl ester

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 1h;100%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃;100%
With triethylamine In chloroform at 25℃; for 0.25h;90%
(4R,5S)-1,5-dimethyl-4-phenylimidazolidin-2-one
92841-65-1

(4R,5S)-1,5-dimethyl-4-phenylimidazolidin-2-one

acryloyl chloride
814-68-6

acryloyl chloride

(4R,5S)-1,5-dimethyl-4-phenyl-3-(2-propenoyl)-2-imidazolidinone
139109-23-2

(4R,5S)-1,5-dimethyl-4-phenyl-3-(2-propenoyl)-2-imidazolidinone

Conditions
ConditionsYield
With 2,3-Dimethylaniline100%
With 1,4-diaza-bicyclo[2.2.2]octane; copper; copper(l) chloride In tetrahydrofuran Ambient temperature;98%
Stage #1: (4R,5S)-1,5-dimethyl-4-phenylimidazolidin-2-one With 1,4-diaza-bicyclo[2.2.2]octane; copper; copper(l) chloride In tetrahydrofuran at 20℃; for 0.25h; deprotonation;
Stage #2: acryloyl chloride In tetrahydrofuran Substitution;
98%
With N-ethyl-N,N-diisopropylamine; copper(l) chloride In dichloromethane for 2h; Heating;97%
(S,S,S)-1,3,5-tris(α-methylbenzyl)-1,3,5-hexahydrotriazine
131968-96-2

(S,S,S)-1,3,5-tris(α-methylbenzyl)-1,3,5-hexahydrotriazine

acryloyl chloride
814-68-6

acryloyl chloride

N-(S)-phenylethyl-N-chloromethylacrylamide
131968-97-3

N-(S)-phenylethyl-N-chloromethylacrylamide

Conditions
ConditionsYield
In dichloromethane at 0℃; for 0.166667h;100%
In dichloromethane at 0℃; for 0.333333h;
3-(2-Aminoethylthio)propyl-L-glycero-α-D-manno-heptopyranosid hydrochloride
135284-16-1

3-(2-Aminoethylthio)propyl-L-glycero-α-D-manno-heptopyranosid hydrochloride

acryloyl chloride
814-68-6

acryloyl chloride

3-<2-(Acrylamido)ethylthio>propyl-L-glycero-α-D-manno-heptopyranosid
135284-19-4

3-<2-(Acrylamido)ethylthio>propyl-L-glycero-α-D-manno-heptopyranosid

Conditions
ConditionsYield
With triethylamine In 1,4-dioxane; methanol; water at 0℃; for 0.25h; pH ca. 9;100%
1,2;4,5-di-O-isopropylidene-β-D-(-)-fructopyranose
25018-67-1

1,2;4,5-di-O-isopropylidene-β-D-(-)-fructopyranose

acryloyl chloride
814-68-6

acryloyl chloride

3-O-acryloyl-1,2;4,5-di-O-isopropylidene-β-D-(-)-fructopyranose
122444-93-3

3-O-acryloyl-1,2;4,5-di-O-isopropylidene-β-D-(-)-fructopyranose

Conditions
ConditionsYield
With pyridine In acetonitrile at 20℃;100%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 6h; Acylation;80%
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 96h; Ambient temperature;74%
With sodium hydride 1.) ligroin, 80 deg C, 1 h, 2.) -30 deg C to 65 deg C; Yield given. Multistep reaction;
acryloyl chloride
814-68-6

acryloyl chloride

2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-O-[p-(n-decanamido)benzyl]-β-D-glucopyranoside
210423-90-8

2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-O-[p-(n-decanamido)benzyl]-β-D-glucopyranoside

Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-(4-acryloylamino-benzyloxy)-tetrahydro-pyran-4-yl ester
158979-47-6

Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-(4-acryloylamino-benzyloxy)-tetrahydro-pyran-4-yl ester

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran; methanol at 0℃; for 2h;100%
With triethylamine In methanol pH 9; Yield given;
N-butylamine
109-73-9

N-butylamine

acryloyl chloride
814-68-6

acryloyl chloride

N-butylacrylamide
2565-18-6

N-butylacrylamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 1.5h;100%
With triethylamine In dichloromethane at 0 - 20℃; for 12h;88%
With triethylamine In dichloromethane at 0 - 20℃;87%
acryloyl chloride
814-68-6

acryloyl chloride

(2S,4S,5R)-5-((2S,3R)-1-Allyl-3-methoxy-4-oxo-azetidin-2-yl)-2-methyl-pyrrolidine-2,4-dicarboxylic acid dimethyl ester
353494-39-0

(2S,4S,5R)-5-((2S,3R)-1-Allyl-3-methoxy-4-oxo-azetidin-2-yl)-2-methyl-pyrrolidine-2,4-dicarboxylic acid dimethyl ester

(2S,4S,5R)-1-Acryloyl-5-((2S,3R)-1-allyl-3-methoxy-4-oxo-azetidin-2-yl)-2-methyl-pyrrolidine-2,4-dicarboxylic acid dimethyl ester
353494-49-2

(2S,4S,5R)-1-Acryloyl-5-((2S,3R)-1-allyl-3-methoxy-4-oxo-azetidin-2-yl)-2-methyl-pyrrolidine-2,4-dicarboxylic acid dimethyl ester

Conditions
ConditionsYield
With triethylamine100%
With triethylamine In dichloromethane at 0℃; for 3h;100%
acryloyl chloride
814-68-6

acryloyl chloride

O-2,4-dimethoxybenzyl-N-2,4,6-trimethoxybenzyl hydroxylamine
215607-30-0

O-2,4-dimethoxybenzyl-N-2,4,6-trimethoxybenzyl hydroxylamine

N-(2,4,6-trimethoxybenzyl)-O-(2,4-dimethoxybenzyl)acrylic hydroxamate

N-(2,4,6-trimethoxybenzyl)-O-(2,4-dimethoxybenzyl)acrylic hydroxamate

Conditions
ConditionsYield
With 4-methyl-morpholine In dichloromethane100%
acryloyl chloride
814-68-6

acryloyl chloride

6-(3-hydroxypropyl)-2,2'-bipyridine

6-(3-hydroxypropyl)-2,2'-bipyridine

3-(2,2'-bipyridin-6-yl)propyl acrylate

3-(2,2'-bipyridin-6-yl)propyl acrylate

Conditions
ConditionsYield
at 20℃;100%
acryloyl chloride
814-68-6

acryloyl chloride

(2S,4S,5R)-5-((2S,3R)-1-Allyl-3-methoxy-4-oxo-azetidin-2-yl)-pyrrolidine-2,4-dicarboxylic acid dimethyl ester
502147-52-6

(2S,4S,5R)-5-((2S,3R)-1-Allyl-3-methoxy-4-oxo-azetidin-2-yl)-pyrrolidine-2,4-dicarboxylic acid dimethyl ester

(2S,4S,5R)-1-Acryloyl-5-((2S,3R)-1-allyl-3-methoxy-4-oxo-azetidin-2-yl)-pyrrolidine-2,4-dicarboxylic acid dimethyl ester
502147-54-8

(2S,4S,5R)-1-Acryloyl-5-((2S,3R)-1-allyl-3-methoxy-4-oxo-azetidin-2-yl)-pyrrolidine-2,4-dicarboxylic acid dimethyl ester

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0℃; for 3h;100%
(1S,2R)-(+)-N-methylephedrine
42151-56-4

(1S,2R)-(+)-N-methylephedrine

acryloyl chloride
814-68-6

acryloyl chloride

(1S,2R)-N-methylephedrinyl acrylate
187600-79-9

(1S,2R)-N-methylephedrinyl acrylate

Conditions
ConditionsYield
With triethylamine In diethyl ether at 0 - 20℃; for 2h;100%
acryloyl chloride
814-68-6

acryloyl chloride

(R)-4-[2,2'-bis(tert-butyldimethylsilyloxy)-1,1'-binaphth-6-yl]butan-1-ol

(R)-4-[2,2'-bis(tert-butyldimethylsilyloxy)-1,1'-binaphth-6-yl]butan-1-ol

acrylic acid 4-[2,2'-bis-(tert-butyl-dimethyl-silanyloxy)-[1,1']binaphthalenyl-6-yl]-butyl ester

acrylic acid 4-[2,2'-bis-(tert-butyl-dimethyl-silanyloxy)-[1,1']binaphthalenyl-6-yl]-butyl ester

Conditions
ConditionsYield
In tetrahydrofuran at 0℃; for 0.5h;100%
acryloyl chloride
814-68-6

acryloyl chloride

(Z)-3-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-phenyl-ethylamino]-but-2-enoic acid methyl ester
725250-70-4

(Z)-3-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-phenyl-ethylamino]-but-2-enoic acid methyl ester

1-[2-(tert-butyl-dimethyl-silanyloxy)-(1S)-phenyl-ethyl]-2-methyl-6-oxo-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid methyl ester
595582-03-9

1-[2-(tert-butyl-dimethyl-silanyloxy)-(1S)-phenyl-ethyl]-2-methyl-6-oxo-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid methyl ester

Conditions
ConditionsYield
In tetrahydrofuran at 0℃; for 0.25h;100%
In tetrahydrofuran
2-[2-(3,4-Dimethoxy-phenyl)-ethylamino]-cyclohex-1-enecarboxylic acid ethyl ester
77638-67-6

2-[2-(3,4-Dimethoxy-phenyl)-ethylamino]-cyclohex-1-enecarboxylic acid ethyl ester

acryloyl chloride
814-68-6

acryloyl chloride

1-[2-(3,4-dimethoxy-phenyl)-ethyl]-2-oxo-1,3,4,5,6,7-hexahydro-2H-quinoline-4a-carboxylic acid ethyl ester

1-[2-(3,4-dimethoxy-phenyl)-ethyl]-2-oxo-1,3,4,5,6,7-hexahydro-2H-quinoline-4a-carboxylic acid ethyl ester

Conditions
ConditionsYield
In 1,4-dioxane at 60℃; for 1.5h;100%
acryloyl chloride
814-68-6

acryloyl chloride

(Z)-3-[2-(3,4-Dimethoxy-phenyl)-ethylamino]-but-2-enoic acid ethyl ester
604763-51-1

(Z)-3-[2-(3,4-Dimethoxy-phenyl)-ethylamino]-but-2-enoic acid ethyl ester

1-[2-(3,4-dimethoxy-phenyl)-ethyl]-2-methyl-6-oxo-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid ethyl ester

1-[2-(3,4-dimethoxy-phenyl)-ethyl]-2-methyl-6-oxo-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid ethyl ester

Conditions
ConditionsYield
In tetrahydrofuran100%
acryloyl chloride
814-68-6

acryloyl chloride

(Z)-3-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-phenyl-ethylamino]-5-[1,3]dioxolan-2-yl-pent-2-enoic acid methyl ester
725250-76-0

(Z)-3-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-phenyl-ethylamino]-5-[1,3]dioxolan-2-yl-pent-2-enoic acid methyl ester

1-[2-(tert-butyl-dimethyl-silanyloxy)-(1S)-phenyl-ethyl]-2-(2-[1,3]dioxolan-2-yl-ethyl)-6-oxo-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid methyl ester

1-[2-(tert-butyl-dimethyl-silanyloxy)-(1S)-phenyl-ethyl]-2-(2-[1,3]dioxolan-2-yl-ethyl)-6-oxo-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid methyl ester

Conditions
ConditionsYield
In tetrahydrofuran at 0℃; for 0.25h;100%
acryloyl chloride
814-68-6

acryloyl chloride

(Z)-3-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-phenyl-ethylamino]-6-[1,3]dioxolan-2-yl-hex-2-enoic acid methyl ester
725250-73-7

(Z)-3-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-phenyl-ethylamino]-6-[1,3]dioxolan-2-yl-hex-2-enoic acid methyl ester

1-[2-(tert-butyl-dimethyl-silanyloxy)-1-phenyl-ethyl]-2-(3-[1,3]dioxolan-2-yl-propyl)-6-oxo-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid methyl ester
725250-78-2

1-[2-(tert-butyl-dimethyl-silanyloxy)-1-phenyl-ethyl]-2-(3-[1,3]dioxolan-2-yl-propyl)-6-oxo-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid methyl ester

Conditions
ConditionsYield
In tetrahydrofuran at 0℃; for 0.25h;100%
C22H30O9

C22H30O9

acryloyl chloride
814-68-6

acryloyl chloride

C25H32O10

C25H32O10

Conditions
ConditionsYield
With N-isopropylethylamine In tetrahydrofuran at 20℃;100%
With N-ethyl-N,N-diisopropylamine100%
1-vinyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
129137-67-3

1-vinyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

acryloyl chloride
814-68-6

acryloyl chloride

1-(6,7-dimethoxy-1-vinyl-3,4-dihydro-1H-isoquinolin-2-yl)propenone

1-(6,7-dimethoxy-1-vinyl-3,4-dihydro-1H-isoquinolin-2-yl)propenone

Conditions
ConditionsYield
With 2,6-dimethylpyridine In dichloromethane at 0℃; for 1h;100%
acryloyl chloride
814-68-6

acryloyl chloride

(R)-1-[(4-methoxybenzyl)oxy]pent-4-en-2-ol
194342-84-2

(R)-1-[(4-methoxybenzyl)oxy]pent-4-en-2-ol

Acrylic acid (R)-1-(4-methoxy-benzyloxymethyl)-but-3-enyl ester
909570-85-0

Acrylic acid (R)-1-(4-methoxy-benzyloxymethyl)-but-3-enyl ester

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 1h;100%
With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 12h;91%
acryloyl chloride
814-68-6

acryloyl chloride

dibenzylamine
103-49-1

dibenzylamine

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at -78 - 20℃; for 1.33333h;100%
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at -78 - 20℃; for 1.33333h;100%
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0℃; for 2h;83%
4-fluoroaniline

4-fluoroaniline

N-(4-fluorophenyl)acrylamide
60252-77-9

N-(4-fluorophenyl)acrylamide

Conditions
ConditionsYield
With sodium hydrogencarbonate; triethylamine In tetrahydrofuran100%
With triethylamine In ethyl acetate at 0 - 20℃; for 2h; Inert atmosphere;92%
With triethylamine In dichloromethane at 0 - 20℃; for 12h;66%
N,N',N"-trimethyl-3-hydroxypropylammonium salt

N,N',N"-trimethyl-3-hydroxypropylammonium salt

acryloyl chloride
814-68-6

acryloyl chloride

ammonium acrylate
10604-69-0

ammonium acrylate

Conditions
ConditionsYield
potassium carbonate In acetonitrile100%
acryloyl chloride
814-68-6

acryloyl chloride

(para-bromophenyl)-2-propenoate
50663-21-3

(para-bromophenyl)-2-propenoate

Conditions
ConditionsYield
Stage #1: 4-bromo-phenol With sodium hydride In tetrahydrofuran at 0℃; for 0.25h;
Stage #2: acryloyl chloride In tetrahydrofuran at 0℃; for 0.25h;
100%
C17H31NO5
937204-25-6

C17H31NO5

acryloyl chloride
814-68-6

acryloyl chloride

C20H33NO6
937204-26-7

C20H33NO6

Conditions
ConditionsYield
With dmap; N-ethyl-N,N-diisopropylamine In dichloromethane at -78 - 20℃; for 12h;100%
1,2;4,5-di-O-isopropylidene-β-D-(-)-fructopyranose
25018-67-1

1,2;4,5-di-O-isopropylidene-β-D-(-)-fructopyranose

acryloyl chloride
814-68-6

acryloyl chloride

1-O-acryloyl-2,3;4,5-di-O-isopropylidene-β-D-(-)-fructopyranose
122444-91-1

1-O-acryloyl-2,3;4,5-di-O-isopropylidene-β-D-(-)-fructopyranose

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane In acetonitrile at 20℃;100%
(3-acryloyloxypropyl)trimethylammonium bis(trifluoromethylsulfonyl)imide

(3-acryloyloxypropyl)trimethylammonium bis(trifluoromethylsulfonyl)imide

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 18 - 22℃; for 2h;100%
With potassium carbonate In acetonitrile at 80℃; Inert atmosphere;98%
With potassium carbonate In acetonitrile at 80℃; for 3h;90%

814-68-6Relevant articles and documents

The molecular design of photo-curable and high-strength benzoxazine for 3D printing

Lu, Yong,Ng, Kok Wei Joseph,Chen, Hui,Chen, Xuelong,Lim, Song Kiat Jacob,Yan, Weili,Hu, Xiao

supporting information, p. 3375 - 3378 (2021/04/07)

Low viscosity photo-curable benzoxazines (BZs) are designed and synthesized for use in stereolithography 3D printing. An initial investigation shows that the thermally polymerized polybenzoxazines (PBZs) have remarkably highTg(264 °C) and flexural modulus (4.91 GPa) values. Subsequently, the formulated photoprintable resins are employed for use in high-resolution projection micro-stereolithography (PμSL) printing. Complex PBZ 3D structures can be achieved from the as-printed objects after they are thermally treated. These findings advance the design of BZ monomers for photopolymerization-based 3D printing and offer a method for the efficient fabrication of high-performance thermosets for various demanding engineering applications.

Synthesis and Biological Evaluation of Celastrol Derivatives with Improved Cytotoxic Selectivity and Antitumor Activities

Feng, Jia-Hao,He, Qi-Wei,Hou, Ji-Qin,Hu, Xiao-Long,Long, Huan,Wang, Bao-Lin,Wang, Hao,Wang, Quan,Wang, Rong,Ye, Wen-Cai,Zhang, Li-Xin,Zhang, Xiao-Qi

, p. 1954 - 1966 (2021/07/20)

Cdc37 associates kinase clients to Hsp90 and promotes the development of cancers. Celastrol, a natural friedelane triterpenoid, can disrupt the Hsp90-Cdc37 interaction to provide antitumor effects. In this study, 31 new celastrol derivatives, 2a - 2d , 3a - 3g , and 4a - 4t , were designed and synthesized, and their Hsp90-Cdc37 disruption activities and antiproliferative activities against cancer cells were evaluated. Among these compounds, 4f , with the highest tumor cell selectivity (15.4-fold), potent Hsp90-Cdc37 disruption activity (IC50= 1.9 μM), and antiproliferative activity against MDA-MB-231 cells (IC50= 0.2 μM), was selected as the lead compound. Further studies demonstrated 4f has strong antitumor activities both in vitro and in vivo through disrupting the Hsp90-Cdc37 interaction and inhibiting angiogenesis. In addition, 4f exhibited less toxicity than celastrol and showed a good pharmacokinetics profile in vivo. These findings suggest that 4f may be a promising candidate for development of new cancer therapies.

An efficient approach for the synthesis of new (±)-coixspirolactams

Nascimento, Vinicius R.,Suenaga, Melissa L. S.,Andrade, Leandro H.

supporting information, p. 5458 - 5465 (2020/08/03)

Coixspirolactams, spiro[oxindole-γ-lactones], are found in adlay seeds and exhibit anticancer activity. A novel synthetic methodology was developed to enable an easy access to (±)-coixspirolactam A and a large number of new coixspirolactams in excellent overall yields. The exquisite exploitation of formamide reactivity was essential for the construction of oxindole and lactone scaffolds. This journal is

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