CAS 107-93-7 2-Butenoic acid (HCID 19499)

Overview

2-butenoic acid has been reported in Daucus carota with data available.

Names & identifiers

Preferred name: 2-Butenoic acid
IUPAC: but-2-enoic acid
English name: Crotonic acid
Molecular formula: C4H6O2
Molecular weight: 86.09

Names & synonyms

2-Butenoic acidDTXSID7027544DTXCID507544CHEBI:17217RefChem:1062626but-2-enoic acid503-64-0.alpha.-Crotonic acidCH3CH=CHCOOHFA 4:1UN 2823alpha-butenic acid

Show more names

(E)-But-2-enoic acidCrotonateBUTENOIC ACIDTRANS-CROTONIC ACID(E)-2-BUTENOIC ACID2-Butenoic acid, (E)-FEMA 3908(2E)-2-Butenoic acidNSC 8751

Crotonic acid (NIST)SCHEMBL22034SCHEMBL23398SCHEMBL294338SCHEMBL1007083SCHEMBL7670830SCHEMBL7670833SCHEMBL7677233

Database identifiers

CAS: 107-93-7、3724-65-0
PubChem CID: 19499
DTXSID: DTXSID7027544
ChEMBL: CHEMBL3185203

Properties

Computed structural properties

XLogP: 0.7
Topological polar surface area: 37.3 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 2
Rotatable bonds: 1
Heavy atoms: 6
Formal charge: 0
Complexity: 73.6

Experimental & physicochemical properties

LipidsFatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Unsaturated fatty acids [FA0103]

CosmeticsStabilizing

SpringerMaterials PropertiesDensity

Solubility · 2 items

Slightly soluble in water

Soluble (in ethanol)

Physical Description · 2 items

Dry Powder

Off-white powder; Harsh, pungent, acrylic odour

Physicochemical properties

Melting point: 70 · 70-72 °C (lit.)
Boiling point: 180 · 180-181 °C (lit.)
Density: 1.027 g/mL · 1.027 g/mL at 25 °C (lit.)
bulk density: 543 kg/m3 · 543kg/m3
vapor density: 2.97 · 2.97 (vs air)
vapor pressure: 0.19 mm · 0.19 mm Hg ( 20 °C)
refractive index: 1.4228 · 1.4228
FEMA: 3908 · 3908 | (E)-2-BUTENOIC ACID
Flash point: 190 °F · 190 °F
storage temp.: 30 °C · Store below +30°C.
solubility: 2 O: · H2O: soluble
pka: 4.69 · 4.69(at 25℃)
form: Crystalline Flakes
color: White to light yellow
PH: 3 · 3 (10g/l, H2O, 20℃)
Odor: 1 % · at 1.00 %. milky
Odor Type: milky
explosive limit: 15.1 %, · 15.1%, 171°F
Water Solubility: 94 g/L · 94 g/L (25 ºC)
Merck: 14 · 14,2597
JECFA Number: 1371 · 1371
BRN: 1719943 · 1719943
Henry's Law Constant: 4.1 · 4.1×101 mol/(m3Pa) at 25℃, HSDB (2015)
InChI: 1S/C4H6O2/c1-2-3-4(5)6/h2-3H,1H3,(H,5,6)/b3-2+
InChIKey: LDHQCZJRKDOVOX-NSCUHMNNSA-N
SMILES: [H]\C(C)=C(\[H])C(O)=O
LogP: 0.85 at · 0.85 at 25℃
FDA 21 CFR: 176.18 · 176.180
CAS DataBase Reference: 107 · 107-93-7(CAS DataBase Reference)
EWG's Food Scores: 1 · 1
FDA UNII: 5 WZZ4O5Q · YW5WZZ4O5Q
NIST Chemistry Reference: Crotonic acid(107-93-7)
EPA Substance Registry System: 2 · 2-Butenoic acid, (2E)- (107-93-7)
UNSPSC Code: 12352106 · 12352106
NACRES: 22 · NA.22
Symbol(GHS): 5 · GHS05
Signal word: Danger
Hazard statements: 318 · H318
Precautionary statements: 280 · P280-P305+P351+P338
PPE: 3 · Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
Hazard Codes: C,N,Xi
Risk Statements: 21 · 21/22-34-50/53-36/37/38
Safety Statements: 26 · 26-36/37/39-45-61-37/39
RIDADR: 2823 · UN 2823 8/PG III (CROTONIC ACID, SOLID)
WGK Germany: 3 · 3
RTECS: 2900000 · GQ2900000
Autoignition Temperature: 744 °F · 744 °F
HazardClass: 8 · 8
PackingGroup: III
HS Code: 29161940 · 29161940
Storage Class: 8 A · 8A - Combustible corrosive hazardous materials
Hazard Classifications: 1 · Eye Dam. 1
Toxicity: 50 orally · LD50 orally in rats: 1.0 g/kg (Smyth, Carpenter)
REACH Registrations: Active
Limited Quantities: 5 L · 5.0 L (1.3 gallons) (liquid) or 5.0 kg (11 lbs) (solid)
Excepted Quantities: Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)

Safety & regulation

Hazard information

Regulatory Information · 3 items

Chemical: 2-Butenoic acid

2-Butenoic acid is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Butenoic acid are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Crotonic acid: Does not have an individual approval but may be used under an appropriate group standard

Safety data

PPE: Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
wgk: 3
rtecs: GQ2900000
ridadr: UN 3472 8/PG III (CROTONIC ACID, LIQUID)
hs_code: 29161940
Toxicity: LD50 orally in rats: 1.0 g/kg (Smyth, Carpenter)
risk_code: 21/22-34-50/53-36/37/38
Signal word: Danger
Symbol(GHS): GHS05
hazard_code: C,N,Xi
safety_code: 26-36/37/39-45-61-37/39
hazard_class: 8
Storage Class: 8A - Combustible corrosive hazardous materials
packing_group: III
Hazard statements: H318
Limited Quantities: 5.0 L (1.3 gallons) (liquid) or 5.0 kg (11 lbs) (solid)
Excepted Quantities: Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
REACH Registrations: Active
Hazard Classifications: Eye Dam. 1
Autoignition Temperature: 744 °F
Precautionary statements: P280-P305+P351+P338

Chemistry & industry

Uses & manufacturing

U.S. Production2023: 224,869 lb

Consumer UsesDye

Industry UsesMonomers

Use Classification · 2 items

Flavoring Agents -> JECFA Flavorings Index

Cosmetics -> Stabilizing

General Manufacturing Information · 2 items

All Other Basic Organic Chemical Manufacturing

2-Butenoic acid: ACTIVE

Applications

Usestrans-Crotonic acid is used in the copolymerization of crotonic acid hydrogel systems by using gamma-rays. The crosslinked copolymeric crotonic acid hydrogels release fertilizers and drugs that help to prevent environmental pollution.

General DescriptionCrotonic acid undergoes esterification with butan-2-ol by following second order reaction kinetics.

Preparation methods

Preparation(E)-2-Butenoic acid may be formed by oxidation of crotonaldehyde, 2-butenal. If (Z)-butenoic acid is heated at 180°C, it is converted to (E)-2-butenoid acid.

Upstream & downstream products

Upstream raw materials

Downstream products

3-Phenylbutyric acid DL-3-Hydroxybutyric acid monosodium salt Crotamiton DL-3-Hydroxybutyric acid sodium salt 4-Bromocrotonic acid beta-Methyllevulinic acid 2,3-Dibromobutyric acid 3-Mercaptobutyric acid DL-3-Aminobutyric acid 2-Butenoic acid, cyclohexyl ester, (2E)-HEPTYL-CROTONATE HEXYLCROTONATE

Suppliers101 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

杭州布朗生物医药科技有限公司15967138206

河北立业化学制品有限公司0310-6697998 13930001710 · [email protected]

Additional notes

DefinitionChEBI: Crotonic acid is a but-2-enoic acid with a trans- double bond at C-2. It has been isolated from Daucus carota. It has a role as a plant metabolite. It is a conjugate acid of a crotonate.

Related reactions

26 records

New reaction record

HRID 40892As reactantuspto-grants-2013_09

HRID 44926As reactantuspto-grants-2013_09

HRID 64323As reactantuspto-grants-2016_09

HRID 136333As reactantTraining data from https://doi.org/10.1039/C8SC04228D (9/10)

HRID 285988As reactantTraining data from https://doi.org/10.1039/C8SC04228D (8/10)

HRID 287622As reactantTraining data from https://doi.org/10.1039/C8SC04228D (8/10)

HRID 682015As reactantTraining data from https://doi.org/10.1039/C8SC04228D (3/10)

HRID 689693As reactantTraining data from https://doi.org/10.1039/C8SC04228D (3/10)

Compound notes

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Basic information