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80-59-1

Basic Information
CAS No.: 80-59-1
Name: 2-Butenoic acid,2-methyl-, (2E)-
Molecular Structure:
Molecular Structure of 80-59-1 (2-Butenoic acid,2-methyl-, (2E)-)
Formula: C5H8O2
Molecular Weight: 100.12
Synonyms: 2-Butenoicacid, 2-methyl-, (E)-;Crotonic acid, 2-methyl-, (E)- (8CI);Tiglic acid(6CI,7CI);(E)-2-Methyl-2-butenoic acid;(E)-a-Methylcrotonic acid;Cevadic acid;NSC 44235;NSC 8999;trans-2,3-Dimethylacrylic acid;trans-2-Methyl-2-butenoic acid;trans-a,b-Dimethylacrylic acid;
EINECS: 201-295-0
Density: 1.01 g/cm3
Melting Point: 61-64 °C(lit.)
Boiling Point: 198.499 °C at 760 mmHg
Flash Point: 95.95 °C
Solubility: Easily soluble in hot water; soluble in ethanol and aether; slightly soluble in cold water
Appearance: white to beige crystalline powder and chunks
Hazard Symbols: CorrosiveC,IrritantXi
Risk Codes: 34-36/37/38
Safety: 26-36/37/39-45-24/25-27
Transport Information: UN 3261 8/PG 2
PSA: 37.30000
LogP: 1.03720
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Specification

The Tiglic acid, with the CAS registry number 80-59-1, is also known as trans-2,3-Dimethylacrylic acid. It belongs to the product categories of Aromatic Cinnamic Acids, Esters and Derivatives. Its EINECS number is 201-295-0. This chemical's molecular formula is C5H8O2 and molecular weight is 100.12. What's more, its systematic name is (2E)-2-Methyl-2-butenoic acid. Its classification code is Skin / Eye Irritant. This chemical should be sealed and stored in a cool place. It is used as demulsifying agent and pharmaceutical intermediates. This substance is a volatile and crystallizable substance with a sweet, warm spicy odour. It is used in making perfumes and flavoring agents. The salts and esters of tiglic acid are called tiglates.

Physical properties of Tiglic acid are: (1)ACD/LogP: 1.076; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.49; (4)ACD/LogD (pH 7.4): -1.27; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 23.70; (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: 1.451; (14)Molar Refractivity: 26.678 cm3; (15)Molar Volume: 99.111 cm3; (16)Polarizability: 10.576×10-24cm3; (17)Surface Tension: 32.29 dyne/cm; (18)Density: 1.01 g/cm3; (19)Flash Point: 95.95 °C; (20)Enthalpy of Vaporization: 47.913 kJ/mol; (21)Boiling Point: 198.499 °C at 760 mmHg; (22)Vapour Pressure: 0.15 mmHg at 25°C.

Preparation: this chemical can be prepared by 2-ethyl-acrylic acid at the temperature of 230 °C. This reaction will need reagent water with the reaction time of 3 hours. The yield is about 62%.

Tiglic acid can be prepared by 2-ethyl-acrylic acid at the temperature of 230 °C

Uses of Tiglic acid: it can be used to produce (E)-2-methyl-but-2-enoic acid methyl ester by heating. It will need reagent conc. H2SO4 with the reaction time of 24 hours. The yield is about 70%.

Tiglic acid can be used to produce (E)-2-methyl-but-2-enoic acid methyl ester by heating

When you are using this chemical, please be cautious about it as the following:
This chemical can cause burns. It is irritating to eyes, respiratory system and skin. You should take off immediately all contaminated clothing. 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 and avoid contact with skin and eyes. In case of accident or if you feel unwell, you should 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(=C/C)C
(2)Std. InChI: InChI=1S/C5H8O2/c1-3-4(2)5(6)7/h3H,1-2H3,(H,6,7)/b4-3+
(3)Std. InChIKey: UIERETOOQGIECD-ONEGZZNKSA-N

The toxicity data is as follows:  

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rabbit LD50 skin > 5gm/kg (5000mg/kg)   Food and Chemical Toxicology. Vol. 20, Pg. 837, 1982.
rat LD50 oral > 5gm/kg (5000mg/kg)   Food and Chemical Toxicology. Vol. 20, Pg. 837, 1982.