(E)-2-Methylcrotonoyl chloride

Base Information

• Chemical Name: (E)-2-Methylcrotonoyl chloride
• CAS No.: 35660-94-7
• Molecular Formula: C5H7ClO
• Molecular Weight: 118.563
• Hs Code.: 2916190090
• European Community (EC) Number: 252-659-0
• DSSTox Substance ID: DTXSID801299929
• Nikkaji Number: J151.262E,J260.662C
• Wikidata: Q76303670
• Mol file: 35660-94-7.mol

Synonyms:Tigloyl Chloride;35660-94-7;(E)-2-Methylcrotonoyl chloride;(E)-2-methylbut-2-enoyl chloride;TIGLOYLCHLORIDE;trans-2-Methyl-2-butenoyl Chloride;EINECS 252-659-0;3-cis-Methyl-methacryloyl chloride;MFCD00800725;49651-33-4;2-methyl-2-butenoyl chloride;SCHEMBL248833;SCHEMBL248834;TUNLYEHIVPWOHK-ONEGZZNKSA-N;DTXSID801299929;(2E)-2-Methyl-2-butenoyl chloride;(2E)-2-methylbut-2-enoyl chloride;(E)-2-Methyl-but-2-enoyl chloride;AKOS025296175;2-Butenoyl chloride, 2-methyl-, (E)-;AS-46999;T1811;EN300-261371;F11166;trans-2-Methyl-2-butenoyl chloride, >=97.0%;InChI=1/C5H7ClO/c1-3-4(2)5(6)7/h3H,1-2H3/b4-3

Chemical Property of (E)-2-Methylcrotonoyl chloride

Chemical Property:

• Refractive Index: n20/D 1.471
• Boiling Point: 147 °C at 760 mmHg
• Flash Point: 44 °C
• PSA: 17.07000
• Density: 1.049 g/cm³
• LogP: 1.71800
• Storage Temp.: Refrigerator
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 118.0185425
• Heavy Atom Count: 7
• Complexity: 105

Purity/Quality:

98%,99%, ^*data from raw suppliers

Tigloyl Chloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 10-23/24/25-34
• Safety Statements: 16-26-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC=C(C)C(=O)Cl
• Isomeric SMILES: C/C=C(\C)/C(=O)Cl
• Uses: Tigloyl Chloride is used in the polymerization of propylene as well as through a Freidel-Crafts reaction for the preparation of permethylindenyl complexes of transition metals. As well, it is primari ly used as a reagent in the enantioselective synthesis of dihydropyrans.

Technology Process of (E)-2-Methylcrotonoyl chloride

There total 9 articles about (E)-2-Methylcrotonoyl chloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

Tiglic acid (80-59-1) → (E)-2-methylbut-2-enoyl chloride (35660-94-7)

Guidance literature:

With thionyl chloride; at 40 ℃; Reflux;

DOI:10.1021/acs.joc.6b01332

Reference yield: 89.0%

Angelic acid (565-63-9) → (Z)-2-methyl-2-butenoyl chloride (35660-94-7,49651-33-4,62529-65-1)

Guidance literature:

With thionyl chloride; Heating / reflux;

Reference yield: 82.0%

2-methylbut-2-enoic acid (13201-46-2) → (E)-2-methylbut-2-enoyl chloride (35660-94-7)

Guidance literature:

With thionyl chloride; for 5h; Reflux;

upstream raw materials:

Tiglic acid

2-hydroxy-2-methylbutyric acid

oxalyl dichloride

2-methylbut-2-enoic acid

Downstream raw materials:

citronellyl tiglate

geranyl tiglate

2-phenylethyl tiglate

2-methyl-1-phenylbut-2-en-1-one

Refernces

• 1、 Balczewski, Piotr,Mikolajczyk, Marian. "An expeditious synthesis of (±)-desepoxy-4,5-didehydromethylenomycin A methyl ester". . p. 1153 - 1154. Retrieved 2000.
• 2、 Tatsukawa, Mari,Punzalan, Louvy Lynn C.,Magpantay, Hilbert D.S.,Villase?or, Irene M.,Concepcion, Gisela P.,Suwanborirux, Khanit,Yokoya, Masashi,Saito, Naoki. "Chemistry of renieramycins. Part 13: Isolation and structure of stabilized renieramycin type derivatives, renieramycins W-Y, from Philippine blue sponge Xestospongia sp., pretreated with potassium cyanide". . p. 7422 - 7428. Retrieved 2012.
• 3、 Yokoya, Masashi,Toyoshima, Ryoko,Suzuki, Toshihiro,Le, Vy H.,Williams, Robert M.,Saito, Naoki. "Stereoselective Total Synthesis of (-)-Renieramycin T". . p. 4039 - 4047. Retrieved 2016.
• 4、 Yokoya, Masashi,Ito, Hiroshi,Saito, Naoki. "Chemistry of renieramycins. Part 11: Total synthesis of (±)-cribrostatin 4". . p. 9185 - 9192. Retrieved 2011.
• 5、 Boyko, Yaroslav D.,Chu, Tiffany,Hergenrother, Paul J.,Huck, Christopher J.,Ning, Shang,Sarlah, David,Shved, Alexander S.,Tonogai, Emily J.,Yang, Cheng. "Erratum: Synthetic Studies on Selective, Proapoptotic Isomalabaricane Triterpenoids Aided by Computational Techniques (J. Am. Chem. Soc. (2021) 143:4 (2138-2155) DOI: 10.1021/jacs.0c12569)". supporting information. p. 12418 - 12418. Retrieved 2021/08/30.
• 6、 Wang, Huai-Wei,Qiao, Yu-Han,Wu, Jia-Xue,Wang, Qiu-Ping,Tian, Meng-Xin,Li, Yong-Fei,Yao, Qing-Xia,Li, Da-Cheng,Dou, Jian-Min,Lu, Yi. "RhIII-Catalyzed C-H (Het)arylation/Vinylation of N-2,6-Difluoroaryl Acrylamides". supporting information. p. 656 - 662. Retrieved 2021/02/01.