Heptafluorobutyranilide

Base Information

• Chemical Name: Heptafluorobutyranilide
• CAS No.: 336-61-8
• Molecular Formula: C10H6 F7 N O
• Molecular Weight: 289.153
• Hs Code.: 2924299090
• NSC Number: 404378
• UNII: FH26UK9AJK
• DSSTox Substance ID: DTXSID50187299
• Nikkaji Number: J55.500B
• Wikidata: Q83058954
• Mol file: 336-61-8.mol

Synonyms:Heptafluorobutyranilide;336-61-8;AI 3-18011;2,2,3,3,4,4,4-heptafluoro-N-phenylbutanamide;AI3-18011;Butyranilide, 2,2,3,3,4,4,4-heptafluoro-;FH26UK9AJK;NSC 404378;NSC-404378;BRN 2751596;Butanamide, 2,2,3,3,4,4,4-heptafluoro-N-phenyl-;alpha,alpha,beta,beta,gamma,gamma,gamma-Heptafluorobutyranilide;BUTYRANILIDE, alpha,alpha,beta,beta,gamma,gamma,gamma-HEPTAFLUORO-;4-12-00-00388 (Beilstein Handbook Reference);Butanamide, 2,2,3,3,4,4,4-heptafluoro-N-phenyl- (9CI);NSC404378;starbld0007507;UNII-FH26UK9AJK;WLN: FXFFXFFXFFVMR;C10H6F7NO;Aniline, N-heptafluorobutyryl-;SCHEMBL8846991;DTXSID50187299;C10-H6-F7-N-O;AKOS003625974;LS-47773;Butyranilide,2,3,3,4,4,4-heptafluoro-;FT-0669119;Butanamide,2,3,3,4,4,4-heptafluoro-N-phenyl-;N-Phenyl-2,2,3,3,4,4,4-heptafluorobutanamide;2,2,3,3,4,4,4-HEPTAFLUOROBUTYRANILIDE;J-019287;Butyranilide,.alpha.,.beta.,.beta.,.gamma.,.gamma.,.gamma.-heptafluoro-;Butyranilide, .alpha.,.alpha.,.beta.,.beta.,.gamma.,.gamma.,.gamma.-heptafluoro-

Chemical Property of Heptafluorobutyranilide

Chemical Property:

• Vapor Pressure: 0.0141mmHg at 25°C
• Boiling Point: 257.9°Cat760mmHg
• Flash Point: 109.8°C
• PSA: 29.10000
• Density: 1.491g/cm³
• LogP: 3.53100
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 3
• Exact Mass: 289.03376095
• Heavy Atom Count: 19
• Complexity: 333

Purity/Quality:

98%min ^*data from raw suppliers

Heptafluorobutyranilide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)NC(=O)C(C(C(F)(F)F)(F)F)(F)F
• Uses: Heptafluorobutyranilide (cas# 336-61-8) is a compound useful in organic synthesis.

Technology Process of Heptafluorobutyranilide

There total 7 articles about Heptafluorobutyranilide 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: 18.0%

perfluorobutanesulfonyl azide (65245-26-3) + nitrobenzene (98-95-3,26969-40-4) → perfluoro-n-butane sulfonamide (30334-69-1) + 2,2,3,3,4,4,4-heptafluoro-N-phenylbutanamide (336-61-8)

Guidance literature:

at 120 ℃; for 48h; Inert atmosphere; Neat (no solvent);

DOI:10.1016/j.tet.2011.05.027

Reference yield:

N-(perfluorobutyl)-N-phenylhydroxylamine → 2,2,3,3,4,4,4-heptafluoro-N-phenylbutanamide (336-61-8)

Guidance literature:

With hydrogenchloride; water; acetic acid; zinc; In ethyl acetate; at 65 ℃; for 2h;

DOI:10.1021/acs.orglett.0c00768

Reference yield:

Nitrosobenzene (586-96-9) → 2,2,3,3,4,4,4-heptafluoro-N-phenylbutanamide (336-61-8)

Guidance literature:

Multi-step reaction with 2 steps

1: copper(II) perchlorate hexahydrate; hydroquinone; tert.-butylhydroperoxide / water; ethyl acetate / 1 h / 20 °C

2: acetic acid; water; hydrogenchloride; zinc / ethyl acetate / 2 h / 65 °C

With hydrogenchloride; tert.-butylhydroperoxide; copper(II) perchlorate hexahydrate; water; acetic acid; hydroquinone; zinc; In water; ethyl acetate;

DOI:10.1021/acs.orglett.0c00768

upstream raw materials:

perfluorobutyryl fluoride

aniline

heptafluorobutyryl chloride

heptafluorobutyryl bromide

Downstream raw materials:

4-methoxy-N-phenylbenzamide

N-(1H,1H-heptafluoro-butyl)-aniline

2,2,3,3,4,4,4-heptafluoro-N-phenylbutanethioamide

Refernces

• 1、 Deliaval, Marie,Selander, Nicklas,Van Der Werf, Angela,Zheng, Zhiyao. "Synthesis of Fluorinated Amide Derivatives via a Radical N-Perfluoroalkylation-Defluorination Pathway". supporting information. . Retrieved 2020/04/02.