A NEW SYNTHESIS FOR 3-CHLORO-2,2',4,4',6,6'-HEXANITROBIPHENYL, PIPICL

Dacons, Joseph C.; Kamlet, Mortimer J.

A NEW SYNTHESIS FOR 3-CHLORO-2,2',4,4',6,6'-HEXANITROBIPHENYL, PIPICL

Active / Technical Report | Accession Number: AD0370133 | Open PDF

Abstract:

3-Chloro-2,2,4,4,6,6-hexanitrobiphenyl, PIPICL, was prepared by a three-step procedure from picryl chloride and m-chloro- or m-bromoanisole. The first step involved the formation of m-picrylanisole by means of a mixed Ullmann reaction. Using 90 nitric acid and 30 oleum, the picrylanisole was nitrated to 3-methoxy-2,2,4,4,6,6-hexanitrobiphenyl which was in turn converted to PIPICL by treatment with pyridine and phosphorus oxychloride. When m- bromoanisole was used in the Ullmann reaction, the overall yield for the three steps was about 59. The use of m-chloroanisole resulted in a lower yield in the first step and an overall yield of about 52. Several variations in procedure are given for the preparation of m-picrylanisole.

Author(s):

Dacons, Joseph C. ; Kamlet, Mortimer J.

Author Organization(s):

NAVAL ORDNANCE LAB WHITE OAK MD

Descriptive Note:

Technical rept.,

Supplementary Note:

DOI: 10.21236/AD0370133

Pagination:

0022

Security Markings

DOCUMENT & CONTEXTUAL SUMMARY

Distribution:

Approved For Public Release

Distribution Statement:

Approved For Public Release; Distribution Unlimited.

RECORD

Collection: TR

Identifying Numbers

Report Number(s):

NOLTR-65-215

Monitor Series:

NAVWEPS

Subject Terms

Joint Capability Areas:

JCA_3.2_Engagement; JCA_3_Force Application; JCA_3.2.1_Kinetic Means; JCA_5_Command and Control; JCA_6.4.1_Secure Information Exchange; JCA_5.5.2_Task; JCA_5.5_Direct; JCA_6.4_Information Assurance; JCA_6_Net Centric

Modernization Areas:

Cyber; Fully Networked C3

Communities of Interest:

Weapons Technologies

Descriptor(s):

*EXPLOSIVES, REACTION KINETICS, PHYSICAL PROPERTIES, SYNTHESIS(CHEMISTRY), CRYSTALLIZATION, PURIFICATION, CHLORIDES, ETHERS, CHLORINATION, BROMIDES, NITRATES, NITRATION, BIPHENYL, THIN LAYER CHROMATOGRAPHY

Field(s)/Group(s):

Organic Chemistry, Ammunition and Explosives

Keyword(s):

BROMINE ORGANIC COMPOUNDS, PICRYL CHLORIDE

Report Date:

1966 Jan 18