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3724-65-0

Basic Information
CAS No.: 3724-65-0
Name: trans-Crotonic acid
Article Data: 129
Molecular Structure:
Molecular Structure of 3724-65-0 (trans-Crotonic acid)
Formula: C4H6O2
Molecular Weight: 86.0904
Synonyms: Crotonic acid;3-Methylacrylic acid;Acrylic acid, 3-methyl-;Kyselina krotonova;alpha-Butenoic acid;But-2-enoic acid;
EINECS: 203-533-9
Density: 1.04 g/cm3
Melting Point: 70-72 °C(lit.)
Boiling Point: 176.974 °C at 760 mmHg
Flash Point: 81.555 °C
Solubility: soluble in water, acetone and ethanol
Appearance: Off-white powder with harsh, pungent and acrylic odour
Hazard Symbols: CorrosiveC
Risk Codes: 21/22-34
Safety: 26-36/37/39-45
Transport Information: UN 2823 8/PG 3
PSA: 37.30000
LogP: 0.64710
Synthetic route
4786-20-3

but-2-enenitrile

3724-65-0

2-butenoic acid

Conditions
ConditionsYield
enzyme from Synechocystis sp. PCC 6803 In phosphate buffer at 30℃; for 12h; pH=7.2;98%
201230-82-2

carbon monoxide

107-18-6

allyl alcohol

3724-65-0

2-butenoic acid

Conditions
ConditionsYield
1,4-di(diphenylphosphino)-butane; bis(dibenzylideneacetone)-palladium(0) In 1,2-dimethoxyethane at 190℃; under 30400 Torr; for 48h;93%
123-73-9

crotonaldehyde

3724-65-0

2-butenoic acid

Conditions
ConditionsYield
With tert.-butylhydroperoxide; ammonium cerium (IV) nitrate In water; acetonitrile at 20℃; for 20h; Kinetics; Concentration; chemoselective reaction;92%
With (bipyH2)-CrOCl5 In dichloromethane at 28 - 30℃; for 0.5h;90%
With tert.-butylhydroperoxide; Ammonium iron sulfate In water; dimethyl sulfoxide at 80℃; for 4h; chemoselective reaction;90%
6117-91-5

(E/Z)-2-buten-1-ol

3724-65-0

2-butenoic acid

Conditions
ConditionsYield
With tert.-butylhydroperoxide; ammonium cerium (IV) nitrate In water; acetonitrile at 20℃; for 31h; chemoselective reaction;90%
With tert.-butylhydroperoxide; copper(ll) bromide In water; dimethyl sulfoxide for 24h; Inert atmosphere; Reflux; chemoselective reaction;89%
With sodium hydroxide; hexacyanoferrate(III); sodium ruthenate(VI) In water Thermodynamic data; Kinetics; Mechanism;
With oxygen In toluene at 100℃; under 750.075 Torr; for 0.5h; Catalytic behavior; Reagent/catalyst;
With oxygen In toluene at 80℃; under 750.075 Torr; Catalytic behavior;
600-30-6

2,3-dibromobutanoic acid

3724-65-0

2-butenoic acid

Conditions
ConditionsYield
With sodium hydroxide; sodium tetrahydroborate; 1,2-di(thiophen-2-yl)ditelluride In ethanol; water Ambient temperature;75%
10544-63-5

ethyl crotonate

3724-65-0

2-butenoic acid

Conditions
ConditionsYield
With Dowex-50 In water for 12h; Heating;65%
With sodium hydroxide In methanol; dichloromethane at 20℃; for 0.25h;
625-33-2

3-penten-2-one

3724-65-0

2-butenoic acid

Conditions
ConditionsYield
With Oxone; trifluoroacetic acid In 1,4-dioxane for 10h; Reflux; Green chemistry;58%
10487-71-5

crotonyl chloride

A

3724-65-0

2-butenoic acid

B

84273-03-0

Shikonin Crotonate

Conditions
ConditionsYield
for 12h;A n/a
B 45%
141079-81-4

(R)-3-(Tolylthio)butyric acid

A

3724-65-0

2-butenoic acid

B

141096-33-5

(R)-3-((R)-Toluene-4-sulfinyl)-butyric acid

C

110968-84-8

(R)-3-((S)-Toluene-4-sulfinyl)-butyric acid

Conditions
ConditionsYield
With dihydrogen peroxide In acetone 1.) 0 deg C, 2 h, 2.) rt, 20 h;A 2%
B 45%
C 23.5%
115395-14-7

(R)-3-(Phenylthio)buttersaeure

A

3724-65-0

2-butenoic acid

B

141096-32-4

(R)-3-<(R)-Phenylsulfinyl>butyric acid

C

115395-15-8

(R)-3-<(S)-Phenylsulfinyl>butyric acid

Conditions
ConditionsYield
With dihydrogen peroxide In acetone 1.) 0 deg C, 2 h, 2.) rt, 20 h;A 3%
B 39%
C 11%
With dihydrogen peroxide In acetone 1.) 0 deg C, 2 h, 2.) rt, 20 h;A 2%
B 11%
C 11%
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  • 3724-65-0   C4H6O2     Crotonic acid

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Specification

The Crotonic Acid, with the CAS registry number 3724-65-0, is also known as 3-Methylacrylic acid. It belongs to the product category of Pharmaceutical Intermediates. Its EINECS number is 203-533-9. This chemical's molecular formula is C4H6O2 and molecular weight is 86.09. What's more, its systematic name is Crotonic Acid. Its classification code is Skin / Eye Irritant. It is stable at common pressure and temperature, and it should be sealed and stored in a cool, ventilated and dry place. Moreover, it should be protected from light. This chemical is mainly used as fungicide, surface coating, plasticizer, pharmaceutical intermediate, pesticide intermediate and other organic chemical intermediate, and it is also used as raw materials for preparation of polyvinyl acetate coating.

Physical properties of Crotonic Acid are: (1)ACD/LogP: 0.658; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.12; (4)ACD/LogD (pH 7.4): -1.91; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 9.06; (8)ACD/KOC (pH 7.4): 1.00; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 37.3 Å2; (13)Index of Refraction: 1.449; (14)Molar Refractivity: 22.203 cm3; (15)Molar Volume: 82.803 cm3; (16)Polarizability: 8.802×10-24cm3; (17)Surface Tension: 34.24 dyne/cm; (18)Density: 1.04 g/cm3; (19)Flash Point: 81.555 °C; (20)Enthalpy of Vaporization: 45.568 kJ/mol; (21)Boiling Point: 176.974 °C at 760 mmHg; (22)Vapour Pressure: 0.505 mmHg at 25°C.

Preparation of Crotonic Acid: this chemical can be prepared by but-2-enoic acid ethyl ester by heating. This reaction will need reagent Dowex-50 and solvent H2O with the reaction time of 12 hours. The yield is about 65%.

Crotonic Acid can be prepared by but-2-enoic acid ethyl ester by heating

Uses of Crotonic Acid: it can be used to produce 3-methylsulfanyl-butyric acid at the temperature of 90 °C. It will need reagent 30% aq. KOH with the reaction time of 2 hours. The yield is about 91%.

Crotonic Acid can be used to produce 3-methylsulfanyl-butyric acid at the temperature of 90 °C

When you are using this chemical, please be cautious about it as the following:
This chemical is harmful in contact with skin and if swallowed and can cause burns. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need to wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, you must seek medical advice immediately (show the label where possible).

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(O)C=CC
(2)Std. InChI: InChI=1S/C4H6O2/c1-2-3-4(5)6/h2-3H,1H3,(H,5,6)
(3)Std. InChIKey: LDHQCZJRKDOVOX-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 skin 200mg/kg (200mg/kg)   "Patty's Industrial Hygiene and Toxicology," 3rd rev. ed., Clayton, G.D., and F.E. Clayton, eds., New York, John Wiley & Sons, Inc., 1978-82. Vol. 3 originally pub. in 1979; pub. as 2n rev. ed. in 1985.Vol. 2C, Pg. 4953, 1982.
mouse LD50 intraperitoneal 25mg/kg (25mg/kg)   "Patty's Industrial Hygiene and Toxicology," 3rd rev. ed., Clayton, G.D., and F.E. Clayton, eds., New York, John Wiley & Sons, Inc., 1978-82. Vol. 3 originally pub. in 1979; pub. as 2n rev. ed. in 1985.Vol. 2C, Pg. 4953, 1982.
mouse LD50 oral 4800mg/kg (4800mg/kg)   Biochemical Journal. Vol. 34, Pg. 1196, 1940.
mouse LD50 subcutaneous 3590mg/kg (3590mg/kg)   Journal of Pharmacy and Pharmacology. Vol. 21, Pg. 85, 1969.
rabbit LD50 skin 600mg/kg (600mg/kg)   "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 309, 1986.
rat LD50 oral 1gm/kg (1000mg/kg)   Journal of Industrial Hygiene and Toxicology. Vol. 26, Pg. 269, 1944.

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