4-Pentenoic anhydride

Base Information

• Chemical Name: 4-Pentenoic anhydride
• CAS No.: 63521-92-6
• Molecular Formula: C10H14O3
• Molecular Weight: 182.219
• Hs Code.: 2916199590
• DSSTox Substance ID: DTXSID50369912
• Nikkaji Number: J1.690.841J
• Wikidata: Q82157193
• Mol file: 63521-92-6.mol

Synonyms:4-Pentenoic anhydride;63521-92-6;pent-4-enoic anhydride;Pent-4-enoyl Pent-4-enoate;pent-4-enoicanhydride;SCHEMBL16236;4-Pentenoic anhydride, 98%;Bis(4-pentenoic acid)anhydride;2,6-Dichlorophenoxy)Acetic Acid;DTXSID50369912;NEDHQDYBHYNBIF-UHFFFAOYSA-N;AKOS025213518

Chemical Property of 4-Pentenoic anhydride

Chemical Property:

• Vapor Pressure: 0.0737mmHg at 25°C
• Refractive Index: n20/D 1.447(lit.)
• Boiling Point: 78-81oC0.4 mm Hg(lit.)
• Flash Point: 230 °F
• PSA: 43.37000
• Density: 0.997 g/mL at 25oC(lit.)
• LogP: 1.98860
• Storage Temp.: Refrigerator (+4°C)
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 8
• Exact Mass: 182.094294304
• Heavy Atom Count: 13
• Complexity: 184

Purity/Quality:

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

Pent-4-enoic anhydride 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C=CCCC(=O)OC(=O)CCC=C
• Uses: N-protecting reagent for amino acids and amino sugars removal under deprotecting conditions MOISTURE SENSITIVE 4-Pentenoic anhydride may be used:In the preparation of glucose functionalized (co)polymers.As a monomer in the preparation of cross-linked polyanhydrides.For the preparation of polymers with pendant vinyl or acetylene.

Technology Process of 4-Pentenoic anhydride

There total 2 articles about 4-Pentenoic anhydride 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: 98.0%

pent-4-enoic acid (591-80-0) → 4-pentenoic anhydride (63521-92-6)

Guidance literature:

With dicyclohexyl-carbodiimide; In dichloromethane; Inert atmosphere;

DOI:10.1021/acs.biomac.5b00911

Reference yield: 93.0%

pent-4-enoic acid (591-80-0) + pent-4-enoyl chloride (39716-58-0) → 4-pentenoic anhydride (63521-92-6)

Guidance literature:

With pyridine; In dichloromethane; for 0.5h; Ambient temperature;

DOI:10.1021/jo00129a036

Reference yield: 100.0%

4-pentenoic anhydride (63521-92-6) + 2,3,4,6-tetra-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol (69567-11-9,76738-52-8,126836-30-4) → 2,3,4,6-tetra-O-benzyl-N-pent-4'-enoyl-1-deoxynojirimycin (929619-01-2)

Guidance literature:

With pyridine; at 20 ℃; for 3h;

DOI:10.1021/jo061280p

upstream raw materials:

pent-4-enoic acid

pent-4-enoyl chloride

Downstream raw materials:

1-((2S,6S)-2,6-Bis-benzyloxymethyl-piperidin-1-yl)-pent-4-en-1-one

(2R,6R)-2,6-bis((benzyloxy)methyl)-1-(4'-pentenoyl)piperidine

N-Pent-4-enoyl-L-proline benzyl ester

Refernces

• 1、 Mccallum, Terry,Barriault, Louis. "Light-enabled synthesis of anhydrides and amides". . p. 2874 - 2878. Retrieved 2015/03/30.
• 2、 Madsen, Robert,Roberts, Carmichael,Fraser-Reid, Bert. "The Pent-4-enoyl Group: A Novel Amine-Protecting Group That Is Readily Cleaved under Mild Conditions". . p. 7920 - 7926. Retrieved 2007/10/03.