Product Name

  • Name

    Crotonic anhydride

  • EINECS 210-807-1
  • CAS No. 623-68-7
  • Article Data24
  • CAS DataBase
  • Density 1.038 g/cm3
  • Solubility
  • Melting Point 72oC
  • Formula C8H10O3
  • Boiling Point 247 °C at 760 mmHg
  • Molecular Weight 154.166
  • Flash Point 106.1 °C
  • Transport Information
  • Appearance
  • Safety 26-36/37/39-45
  • Risk Codes 34
  • Molecular Structure Molecular Structure of 623-68-7 (Crotonic anhydride)
  • Hazard Symbols CorrosiveC
  • Synonyms 2-Butenoicacid, anhydride (9CI);Crotonic anhydride (6CI,7CI,8CI);2-Butenoic anhydride;Crotonic acid anhydride;NSC 97397;Crotonic Anhydride;
  • PSA 43.37000
  • LogP 1.20840

Synthetic route

(E)-but-2-enoic acid
107-93-7

(E)-but-2-enoic acid

trans-crotonic anhydride
623-68-7

trans-crotonic anhydride

Conditions
ConditionsYield
With 2-chloro-1,3-dimethylimidazolinium chloride; triethylamine In dichloromethane at 20℃; for 18h; Acylation;96%
With dicyclohexyl-carbodiimide
4-methyleneoxetan-2-one
674-82-8

4-methyleneoxetan-2-one

2-butenoic acid
3724-65-0

2-butenoic acid

trans-crotonic anhydride
623-68-7

trans-crotonic anhydride

Conditions
ConditionsYield
With 1,4-dioxane at 70 - 80℃; folgendes Destillieren des Reaktionsgemisches;
2-butenoic acid
3724-65-0

2-butenoic acid

trans-crotonic anhydride
623-68-7

trans-crotonic anhydride

Conditions
ConditionsYield
With acetic anhydride
(E)-but-2-enoic acid
107-93-7

(E)-but-2-enoic acid

ethynyl methyl ether
6443-91-0

ethynyl methyl ether

trans-crotonic anhydride
623-68-7

trans-crotonic anhydride

Conditions
ConditionsYield
With dichloromethane; mercury(II) oxide
crotonyl chloride
10487-71-5

crotonyl chloride

triethylamine
121-44-8

triethylamine

benzene
71-43-2

benzene

trans-crotonic anhydride
623-68-7

trans-crotonic anhydride

diethyl ether
60-29-7

diethyl ether

(E)-but-2-enoic acid
107-93-7

(E)-but-2-enoic acid

1-ethoxyacetylene
927-80-0

1-ethoxyacetylene

trans-crotonic anhydride
623-68-7

trans-crotonic anhydride

(E)-but-2-enoic acid
107-93-7

(E)-but-2-enoic acid

1-ethoxyacetylene
927-80-0

1-ethoxyacetylene

trans-crotonic anhydride
623-68-7

trans-crotonic anhydride

Conditions
ConditionsYield
With diethyl ether
crotonaldehyde
123-73-9

crotonaldehyde

trans-crotonic anhydride
623-68-7

trans-crotonic anhydride

Conditions
ConditionsYield
With oxygen; cobalt(II) acetate; acetic acid at 30℃; unter leichtem Ueberdruck;
With oxygen; copper (I) acetate; acetic acid at 30℃; unter leichtem Ueberdruck;
With oxygen; manganese(II) acetate; acetic acid at 30℃; unter leichtem Ueberdruck;
With oxygen; acetic acid at 30℃; in Gegenwart einer Mischung von Wismut-,Kobalt- und Kupferpulver;
trans-chrotonyl chloride
625-35-4, 3488-22-0, 10487-71-5

trans-chrotonyl chloride

crotonate of sodium

crotonate of sodium

trans-crotonic anhydride
623-68-7

trans-crotonic anhydride

sodium crotonate

sodium crotonate

trans-crotonic anhydride
623-68-7

trans-crotonic anhydride

Conditions
ConditionsYield
With thionyl chloride; Petroleum ether
trans-crotonic anhydride
623-68-7

trans-crotonic anhydride

methyl 2-O-benzyl-4,6-di-O-methyl-α-D-mannopyranoside
366801-82-3

methyl 2-O-benzyl-4,6-di-O-methyl-α-D-mannopyranoside

methyl 2-O-benzyl-3-O-crotonyl-4,6-di-O-methyl-α-D-mannopyranoside
366801-85-6

methyl 2-O-benzyl-3-O-crotonyl-4,6-di-O-methyl-α-D-mannopyranoside

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane for 16h;100%
trans-crotonic anhydride
623-68-7

trans-crotonic anhydride

polymer, product of radical polymerization, loading of chiral auxiliary 2.42 mmol/g, Mn=5800, Mw=7000 (GPC, polystyrene standards); monomer(S): styrene; (4S)-4-{4-[(4-vinylbenzyl)oxy]benzyl}-1,3-oxazolidin-2-one

polymer, product of radical polymerization, loading of chiral auxiliary 2.42 mmol/g, Mn=5800, Mw=7000 (GPC, polystyrene standards); monomer(S): styrene; (4S)-4-{4-[(4-vinylbenzyl)oxy]benzyl}-1,3-oxazolidin-2-one

polymer, loading of chiral auxiliary 2.42 mmol/g, Mn=7500, Mw=10000 (GPC, polystyrene standards); monomer(s): styrene; (4S)-4-{4-[(4-vinylbenzyl)oxy]benzyl}-1,3-oxazolidin-2-one; trans-crotonic anhydride

polymer, loading of chiral auxiliary 2.42 mmol/g, Mn=7500, Mw=10000 (GPC, polystyrene standards); monomer(s): styrene; (4S)-4-{4-[(4-vinylbenzyl)oxy]benzyl}-1,3-oxazolidin-2-one; trans-crotonic anhydride

Conditions
ConditionsYield
With dmap; triethylamine In tetrahydrofuran at 70℃; for 48h;100%
methyl 6-deoxy-2,3-bis-O-(phenylmethyl)-α-D-glucopyranoside
56750-58-4

methyl 6-deoxy-2,3-bis-O-(phenylmethyl)-α-D-glucopyranoside

trans-crotonic anhydride
623-68-7

trans-crotonic anhydride

methyl 2,3-di-O-benzyl-4-O-crotonyl-6-deoxy-α-D-glucopyranoside
250687-53-7

methyl 2,3-di-O-benzyl-4-O-crotonyl-6-deoxy-α-D-glucopyranoside

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane for 20.5h;99%
trans-crotonic anhydride
623-68-7

trans-crotonic anhydride

methyl 2,4,6-tri-O-benzyl-α-D-galactopyranoside
55697-50-2

methyl 2,4,6-tri-O-benzyl-α-D-galactopyranoside

methyl 2,4,6-tri-O-benzyl-3-O-crotonyl-α-D-galactopyranoside

methyl 2,4,6-tri-O-benzyl-3-O-crotonyl-α-D-galactopyranoside

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane for 120h;98%
trans-crotonic anhydride
623-68-7

trans-crotonic anhydride

methyl-2,3-di-O-benzyl-6-O-(4-toluenesulfonyl)-α-D-glucopyranoside
54522-57-5

methyl-2,3-di-O-benzyl-6-O-(4-toluenesulfonyl)-α-D-glucopyranoside

methyl 2,3-di-O-benzyl-4-O-crotonyl-6-O-p-toluenesulfonyl-α-D-glucopyranoside
366801-70-9

methyl 2,3-di-O-benzyl-4-O-crotonyl-6-O-p-toluenesulfonyl-α-D-glucopyranoside

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane for 23h;98%
trans-crotonic anhydride
623-68-7

trans-crotonic anhydride

methyl 2,3-di-O-pivaloyl-6-O-p-toluenesulfonyl-α-D-glucopyranoside
366801-67-4

methyl 2,3-di-O-pivaloyl-6-O-p-toluenesulfonyl-α-D-glucopyranoside

methyl 4-O-crotonyl-2,3-di-O-pivaloyl-6-O-p-toluenesulfonyl-α-D-glucopyranoside
366801-69-6

methyl 4-O-crotonyl-2,3-di-O-pivaloyl-6-O-p-toluenesulfonyl-α-D-glucopyranoside

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane for 23h;98%
trans-crotonic anhydride
623-68-7

trans-crotonic anhydride

(S)-4-Benzyl-2-oxazolidinone
90719-32-7

(S)-4-Benzyl-2-oxazolidinone

(4S)-3-((E)-2-butenoyl)-4-benzyl-2-oxazolidinone
90719-30-5

(4S)-3-((E)-2-butenoyl)-4-benzyl-2-oxazolidinone

Conditions
ConditionsYield
With triethylamine; lithium chloride In tetrahydrofuran at -15 - 20℃; for 12h;97%
With triethylamine; lithium chloride In tetrahydrofuran for 4h; Ambient temperature;88%
methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside
19488-48-3

methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside

trans-crotonic anhydride
623-68-7

trans-crotonic anhydride

methyl 2,3,6-tri-O-benzyl-4-O-crotonyl-α-D-glucopyranoside

methyl 2,3,6-tri-O-benzyl-4-O-crotonyl-α-D-glucopyranoside

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane for 21h;97%
trans-crotonic anhydride
623-68-7

trans-crotonic anhydride

(1S,2R)-1,2-diphenylethane-1,2-diol
579-43-1

(1S,2R)-1,2-diphenylethane-1,2-diol

meso-hydrobenzoin mono-trans-crotonate

meso-hydrobenzoin mono-trans-crotonate

Conditions
ConditionsYield
With ytterbium(III) chloride In tetrahydrofuran97%
trans-crotonic anhydride
623-68-7

trans-crotonic anhydride

5-(2-((4S,6R)-6-((2S,3S)-3-(benzyloxy)-2-hydroxybutyl)-2,2-diisopropyl-1,3,2-dioxasilinan-4-yl)propan-2-yl)furan-2-carbaldehyde
1352481-42-5

5-(2-((4S,6R)-6-((2S,3S)-3-(benzyloxy)-2-hydroxybutyl)-2,2-diisopropyl-1,3,2-dioxasilinan-4-yl)propan-2-yl)furan-2-carbaldehyde

(E)-((2S,3S)-3-(benzyloxy)-1-((4R,6S)-6-(2-(5-formylfuran-2-yl)propan-2-yl)-2,2-diisopropyl-1,3,2-dioxasilinan-4-yl)butan-2-yl) but-2-enoate
1352481-43-6

(E)-((2S,3S)-3-(benzyloxy)-1-((4R,6S)-6-(2-(5-formylfuran-2-yl)propan-2-yl)-2,2-diisopropyl-1,3,2-dioxasilinan-4-yl)butan-2-yl) but-2-enoate

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 0℃; for 4h; Inert atmosphere;97%
2-[2-((tert-butyldimethylsilanyloxy)methyl)phenyl]propan-1-ol
942062-83-1

2-[2-((tert-butyldimethylsilanyloxy)methyl)phenyl]propan-1-ol

trans-crotonic anhydride
623-68-7

trans-crotonic anhydride

but-2-enoic acid 2-[2-((tert-butyldimethylsilanyloxy)methyl)phenyl]propyl ester
942062-84-2

but-2-enoic acid 2-[2-((tert-butyldimethylsilanyloxy)methyl)phenyl]propyl ester

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 0℃; for 4h;96%
trans-crotonic anhydride
623-68-7

trans-crotonic anhydride

1-adamanthanol
768-95-6

1-adamanthanol

1-Adamantyl crotonate
134690-47-4

1-Adamantyl crotonate

Conditions
ConditionsYield
Acidic catalyst In cyclohexane Heating;95%
trans-crotonic anhydride
623-68-7

trans-crotonic anhydride

1,3-dimethyl-5-adamantanol
707-37-9

1,3-dimethyl-5-adamantanol

3,5-Dimethyl-1-adamantyl crotonate
134690-48-5

3,5-Dimethyl-1-adamantyl crotonate

Conditions
ConditionsYield
Acidic catalyst In cyclohexane Heating;95%
trans-crotonic anhydride
623-68-7

trans-crotonic anhydride

(1R,2R,3S,4R)-3-O-tert-Butyldimethylsilyl-1,2-O-cyclohexylidene-5-hydroxymethyl-5-cyclohexen-1,2,3,4-tetraol
128044-91-7

(1R,2R,3S,4R)-3-O-tert-Butyldimethylsilyl-1,2-O-cyclohexylidene-5-hydroxymethyl-5-cyclohexen-1,2,3,4-tetraol

(1R,2R,3S,4R)-3-O-tert-Butyldimethylsilyl-5-crotonyloxymethyl-1,2-O-cyclohexylidene-5-cyclohexen-1,2,3,4-tetraol
128044-92-8

(1R,2R,3S,4R)-3-O-tert-Butyldimethylsilyl-5-crotonyloxymethyl-1,2-O-cyclohexylidene-5-cyclohexen-1,2,3,4-tetraol

Conditions
ConditionsYield
With pyridine; dmap In dichloromethane95%
With pyridine; dmap In dichloromethane for 12h; Ambient temperature;95%
trans-crotonic anhydride
623-68-7

trans-crotonic anhydride

methyl 6-deoxy-2,3-di-O-methyl-α-D-glucopyranoside
62853-52-5

methyl 6-deoxy-2,3-di-O-methyl-α-D-glucopyranoside

methyl 4-O-crotonyl-6-deoxy-2,3-di-O-methyl-α-D-glucopyranoside
250687-55-9

methyl 4-O-crotonyl-6-deoxy-2,3-di-O-methyl-α-D-glucopyranoside

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane for 13h;95%
trans-crotonic anhydride
623-68-7

trans-crotonic anhydride

(S)-4-benzyl-5,5-dimethyloxazolidin-2-one
168297-85-6

(S)-4-benzyl-5,5-dimethyloxazolidin-2-one

(S)-3-((E)-but-2-enoyl)-4-benzyl-5,5-dimethyloxazolidin-2-one
618436-90-1

(S)-3-((E)-but-2-enoyl)-4-benzyl-5,5-dimethyloxazolidin-2-one

Conditions
ConditionsYield
With triethylamine; lithium chloride In tetrahydrofuran at -78 - 20℃; for 12h;94%
trans-crotonic anhydride
623-68-7

trans-crotonic anhydride

6-(piperazin-1-yl)pyridine-3-carbonitrile dihydrochloride

6-(piperazin-1-yl)pyridine-3-carbonitrile dihydrochloride

6-[4-[(2E)-but-2-enoyl]piperazin-1-yl]pyridine-3-carbonitrile

6-[4-[(2E)-but-2-enoyl]piperazin-1-yl]pyridine-3-carbonitrile

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20 - 30℃; for 1h;94%
trans-crotonic anhydride
623-68-7

trans-crotonic anhydride

methyl 6-deoxy-2,3-di-O-pivaloyl-α-D-glucopyranoside
366801-72-1

methyl 6-deoxy-2,3-di-O-pivaloyl-α-D-glucopyranoside

methyl 4-O-crotonyl-6-deoxy-2,3-di-O-pivaloyl-α-D-glucopyranoside
250687-54-8

methyl 4-O-crotonyl-6-deoxy-2,3-di-O-pivaloyl-α-D-glucopyranoside

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane for 19h;93%
methyl 2,3,4-tri-O-benzyl-D-glucopyranoside
53008-65-4

methyl 2,3,4-tri-O-benzyl-D-glucopyranoside

trans-crotonic anhydride
623-68-7

trans-crotonic anhydride

methyl 2,3,4-tri-O-benzyl-6-O-crotonyl-α-D-glucopyranoside

methyl 2,3,4-tri-O-benzyl-6-O-crotonyl-α-D-glucopyranoside

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane for 18h;92%
trans-crotonic anhydride
623-68-7

trans-crotonic anhydride

methyl 2,3-di-O-benzyl-6-O-pivaloyl-α-D-glucopyranoside
184715-41-1

methyl 2,3-di-O-benzyl-6-O-pivaloyl-α-D-glucopyranoside

methyl 2,3-di-O-benzyl-4-O-crotonyl-6-O-pivaloyl-α-D-glucopyranoside
250687-57-1

methyl 2,3-di-O-benzyl-4-O-crotonyl-6-O-pivaloyl-α-D-glucopyranoside

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane for 7h;92%
dimethylenecyclourethane
497-25-6

dimethylenecyclourethane

trans-crotonic anhydride
623-68-7

trans-crotonic anhydride

3-((E)-but-2-enoyl)oxazolidin-2-one
109299-92-5

3-((E)-but-2-enoyl)oxazolidin-2-one

Conditions
ConditionsYield
With triethylamine; lithium chloride In tetrahydrofuran92%
trans-crotonic anhydride
623-68-7

trans-crotonic anhydride

10-trans crotonyl-10-desacetylbaccatin III

10-trans crotonyl-10-desacetylbaccatin III

Conditions
ConditionsYield
With cerium(III) chloride In tetrahydrofuran at 25℃; for 20h; Under N2;91%
cerium(III) chloride In tetrahydrofuran at 25℃; for 20h;91%
trans-crotonic anhydride
623-68-7

trans-crotonic anhydride

(E)-N-(4-(3-hydroxyhexa-1,5-dien-1-yl)phenyl)nicotinamide

(E)-N-(4-(3-hydroxyhexa-1,5-dien-1-yl)phenyl)nicotinamide

(E)-1-(4-(nicotinamido)phenyl)hexa-1,5-dien-3-yl (E)-but-2-enoate

(E)-1-(4-(nicotinamido)phenyl)hexa-1,5-dien-3-yl (E)-but-2-enoate

Conditions
ConditionsYield
Stage #1: (E)-N-(4-(3-hydroxyhexa-1,5-dien-1-yl)phenyl)nicotinamide With dmap; triethylamine In dichloromethane at 0℃;
Stage #2: trans-crotonic anhydride In dichloromethane at 0 - 20℃; for 3h;
90%
trans-crotonic anhydride
623-68-7

trans-crotonic anhydride

trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

benzaldehyde
100-52-7

benzaldehyde

(E)-But-2-enoic acid cyano-phenyl-methyl ester

(E)-But-2-enoic acid cyano-phenyl-methyl ester

Conditions
ConditionsYield
Stage #1: trimethylsilyl cyanide; benzaldehyde; iron(III) chloride In nitromethane at 0℃; for 0.5h;
Stage #2: trans-crotonic anhydride In nitromethane at 20℃; for 3h;
89%
trans-crotonic anhydride
623-68-7

trans-crotonic anhydride

carbon monoxide
201230-82-2

carbon monoxide

2-bromoaniline
615-36-1

2-bromoaniline

(E)-2-(prop-1-en-1-yl)-4H-benzo[d][1,3]oxazin-4-one
1217821-56-1

(E)-2-(prop-1-en-1-yl)-4H-benzo[d][1,3]oxazin-4-one

Conditions
ConditionsYield
With potassium tetrachloropalladate(II); N-ethyl-N,N-diisopropylamine; catacxium A In toluene at 100℃; under 1500.15 Torr; for 16h; Autoclave;88%
trans-crotonic anhydride
623-68-7

trans-crotonic anhydride

ethyl 3-((4R,5R)-5-((3S,4R,E)-4-((tert-butyldimethylsilyl)oxy)-3-hydroxypent- 1-en-1-yl)-2,2-dimethyl-1,3-dioxolan-4-yl)propanoate

ethyl 3-((4R,5R)-5-((3S,4R,E)-4-((tert-butyldimethylsilyl)oxy)-3-hydroxypent- 1-en-1-yl)-2,2-dimethyl-1,3-dioxolan-4-yl)propanoate

(3S,4R,E)-4-((tert-butyldimethylsilyl)oxy)-1-((4R,5R)-5-(3-ethoxy-3-oxopropyl)- 2,2-dimethyl-1,3-dioxolan-4-yl)pent-1-en-3-yl (E)-but-2-enoate

(3S,4R,E)-4-((tert-butyldimethylsilyl)oxy)-1-((4R,5R)-5-(3-ethoxy-3-oxopropyl)- 2,2-dimethyl-1,3-dioxolan-4-yl)pent-1-en-3-yl (E)-but-2-enoate

Conditions
ConditionsYield
With dmap In pyridine at 20℃; for 5h;88%
trans-crotonic anhydride
623-68-7

trans-crotonic anhydride

(2R)-bornane-10,2-sultam
94594-90-8

(2R)-bornane-10,2-sultam

(1S)-N-crotyl-2,10-camphorsultam
94668-55-0

(1S)-N-crotyl-2,10-camphorsultam

Conditions
ConditionsYield
With triethylamine; lithium chloride In tetrahydrofuran for 4h; Ambient temperature;87%
(4S,5R)-4-benzyl-5-(1'H,1'H,2'H,2'H-perfluorooctyl)-oxazolidin-2-one
857637-92-4

(4S,5R)-4-benzyl-5-(1'H,1'H,2'H,2'H-perfluorooctyl)-oxazolidin-2-one

trans-crotonic anhydride
623-68-7

trans-crotonic anhydride

(E)-(4S,5R)-4-benzyl-3-(2'-butenoyl)-5-(1'H,1'H,2'H,2'H-perfluorooctyl)-2-oxazolidinone
857637-81-1

(E)-(4S,5R)-4-benzyl-3-(2'-butenoyl)-5-(1'H,1'H,2'H,2'H-perfluorooctyl)-2-oxazolidinone

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; lithium chloride In tetrahydrofuran for 24h; Heating;87%

Crotonic Anhydride Chemical Properties

Chemistry informtion about Crotonic Anhydride (CAS NO.623-68-7) is:
IUPAC Name: [(E)-But-2-Enoyl] (E)-But-2-Enoate
Synonyms: 2-Butenoicacid,Anhydride ; Anhydridkyselinykrotonove ; Crotonicacidanhydride ; Crotonic Anhydride ; 2-Butenoic Anhydride ; Trans-2-Butenoic Anhydride ; 2-Butensureanhydrid ; Crotonsaeureanhydrid
Product Categories: Pharmaceutical Intermediates
MF: C8H10O3
MW: 154.16
EINECS: 210-807-1 
Density: 1.038 g/cm3
Flash Point: 106.1 °C
Boiling Point: 247 °C at 760 mmHg
Vapour Pressure: 0.0263 mmHg at 25°C 
Enthalpy of Vaporization: 48.41 kJ/mol
Refractive Index: n20/D 1.473(lit.)
Following is the molecular structure of Crotonic Anhydride (CAS NO.623-68-7) is:

Crotonic Anhydride Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rat LD50 oral 2830mg/kg (2830mg/kg)   American Industrial Hygiene Association Journal. Vol. 23, Pg. 95, 1962.

Crotonic Anhydride Consensus Reports

Reported in EPA TSCA Inventory.

Crotonic Anhydride Safety Profile

Moderately toxic by ingestion. A skin irritant. When heated to decomposition it emits acrid smoke and irritating fumes.
Hazard Codes:
CorrosiveC
Risk Statements:
R34:Causes burns.
Safety Statements:
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
RIDADR: UN 3265 8/PG 3
WGK Germany: 3
RTECS: GQ6125000
HazardClass: 8
PackingGroup III

Crotonic Anhydride Specification

To protect yourself, you can put on faceshields, full-face respirator (US), gloves, goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter.

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