GB1270047A - Aryl phosphonic and phosphonous acid derivatives - Google Patents
Aryl phosphonic and phosphonous acid derivativesInfo
- Publication number
- GB1270047A GB1270047A GB2953470A GB2953470A GB1270047A GB 1270047 A GB1270047 A GB 1270047A GB 2953470 A GB2953470 A GB 2953470A GB 2953470 A GB2953470 A GB 2953470A GB 1270047 A GB1270047 A GB 1270047A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- aralkyl
- compounds
- alkoxy
- prepared
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- -1 Aryl phosphonic Chemical compound 0.000 title abstract 5
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 title abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 5
- 125000003545 alkoxy group Chemical group 0.000 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 125000004104 aryloxy group Chemical group 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 150000002431 hydrogen Chemical class 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 150000002989 phenols Chemical class 0.000 abstract 2
- NREOJSOKYCQCKQ-UHFFFAOYSA-N 2-bromo-4-(4-fluorophenyl)phenol Chemical compound C1=C(Br)C(O)=CC=C1C1=CC=C(F)C=C1 NREOJSOKYCQCKQ-UHFFFAOYSA-N 0.000 abstract 1
- VADKRMSMGWJZCF-UHFFFAOYSA-N 2-bromophenol Chemical class OC1=CC=CC=C1Br VADKRMSMGWJZCF-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 230000002411 adverse Effects 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000002877 alkyl aryl group Chemical group 0.000 abstract 1
- 150000001347 alkyl bromides Chemical class 0.000 abstract 1
- 150000005215 alkyl ethers Chemical class 0.000 abstract 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 229940121363 anti-inflammatory agent Drugs 0.000 abstract 1
- 239000002260 anti-inflammatory agent Substances 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 150000001768 cations Chemical class 0.000 abstract 1
- ITVPBBDAZKBMRP-UHFFFAOYSA-N chloro-dioxido-oxo-$l^{5}-phosphane;hydron Chemical compound OP(O)(Cl)=O ITVPBBDAZKBMRP-UHFFFAOYSA-N 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- LWNLXVXSCCLRRZ-UHFFFAOYSA-N dichlorophosphane Chemical class ClPCl LWNLXVXSCCLRRZ-UHFFFAOYSA-N 0.000 abstract 1
- 150000002170 ethers Chemical class 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 239000011777 magnesium Substances 0.000 abstract 1
- 229910052749 magnesium Inorganic materials 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- NQRYGPXAYYDKJB-UHFFFAOYSA-N phenyl hydrogen phosphonate Chemical class OP(=O)OC1=CC=CC=C1 NQRYGPXAYYDKJB-UHFFFAOYSA-N 0.000 abstract 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 abstract 1
- 230000001766 physiological effect Effects 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000003396 thiol group Chemical class [H]S* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/48—Phosphonous acids [RP(OH)2] including [RHP(=O)(OH)]; Thiophosphonous acids including [RP(SH)2], [RHP(=S)(SH)]; Derivatives thereof
- C07F9/4883—Amides or esteramides thereof, e.g. RP(NR'2)2 or RP(XR')(NR''2) (X = O, S)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/13—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups
- C07C205/20—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups having nitro groups and hydroxy groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/13—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups
- C07C205/26—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups and being further substituted by halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3834—Aromatic acids (P-C aromatic linkage)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/44—Amides thereof
- C07F9/4403—Amides thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4419—Amides of aromatic acids (P-C aromatic linkage)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/48—Phosphonous acids [RP(OH)2] including [RHP(=O)(OH)]; Thiophosphonous acids including [RP(SH)2], [RHP(=S)(SH)]; Derivatives thereof
- C07F9/4808—Phosphonous acids [RP(OH)2] including [RHP(=O)(OH)]; Thiophosphonous acids including [RP(SH)2], [RHP(=S)(SH)]; Derivatives thereof the acid moiety containing a substituent or structure which is considered as characteristic
- C07F9/4841—Aromatic acids or derivatives (P-C aromatic linkage)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1,270,047. Substituted phenyl phosphonates and phosphonites; phenols and ethers thereof. MERCK & CO. Inc. 18 June, 1970 [25 June, 1969; 20 April, 1970], No. 29534/70. Headings C2C and C2P. The invention comprises compounds of the Formulµ I and II where [Ar] is an aromatic grouping optionally substituted at one or more positions by halogen, alkyl, alkenyl, haloalkyl, hydroxy, alkoxy, nitro, amino, mono- or dialkylamino, mercapto, alkylthio, alkylsulphonyl or sulphamoyl, R<SP>1</SP> and R<SP>11</SP> are each hydroxy, alkoxy, aryloxy, aralkoxy, -OM, -NR 3 R 4 or an N-attached heterocyclic ring, or R<SP>1</SP> or R<SP>11</SP> together form a cycloalkylidene ring, M is the cation of a base which will not have an adverse physiological effect in the body, R 3 and R 4 are hydrogen, alkyl, cycloalkyl, aryl or aralkyl and R 2 is hydrogen, alkyl, aralkyl or acyl. Compounds of Formula II in which R<SP>1</SP> and R<SP>11</SP> are alkoxy, aryloxy, aralkoxy, -NR 3 R 4 or an N-attached heterocyclic ring and in which R 2 is alkyl or aralkyl may be prepared by reacting a suitable 5-aryl-2-alkoxy or aralkoxyphenyl magnesium halide with a suitable phosphorochloridate or bromidate. The free acids and salts and the 2-hydroxy and 2- acyloxy derivatives may be obtained from these compounds by conventional procedures. The free acid may be converted to a dichloro compound by reaction with PCl 5 , and this may then be converted to a diamide by reaction with ammonia or an amine. Compounds of the Formula I may be prepared in a similar manner. The compounds of Formulµ I and II may be used as anti-inflammatory agents in pharmaceutical applications. Dichlorophosphines of the Formula III where R 2 is alkyl or alkaryl may be prepared by reacting phosphorus trichloride with a corresponding dialkyl phosphonite. 2 - Bromo, 4 - ([Ar] - R) - substituted phenols such as 4-(p-fluorophenyl)-2-bromophenol may be prepared by reacting bromine with the corresponding phenol. The bromophenols may be converted to the corresponding aralkyl or alkyl ethers by reaction with an aralkyl or alkyl bromide.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US83666569A | 1969-06-25 | 1969-06-25 | |
| US3032470A | 1970-04-20 | 1970-04-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1270047A true GB1270047A (en) | 1972-04-12 |
Family
ID=26705918
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2953470A Expired GB1270047A (en) | 1969-06-25 | 1970-06-18 | Aryl phosphonic and phosphonous acid derivatives |
Country Status (4)
| Country | Link |
|---|---|
| CH (1) | CH551451A (en) |
| FR (1) | FR2053018B1 (en) |
| GB (1) | GB1270047A (en) |
| NL (1) | NL7008634A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2131023A (en) * | 1982-11-25 | 1984-06-13 | Ricoh Kk | Stilbene derivatives and electrophotographic photoconductors containing them |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4322375A (en) * | 1979-02-06 | 1982-03-30 | Ciba-Geigy Corporation | 2-Substituted 5-phenoxyphenylphosphonic acid derivatives |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1495608A (en) * | 1965-08-12 | 1967-09-22 | Monsanto Co | Process for preparing phosphoroamidates, new products and hydraulic fluids thus obtained |
-
1970
- 1970-06-12 NL NL7008634A patent/NL7008634A/xx unknown
- 1970-06-18 GB GB2953470A patent/GB1270047A/en not_active Expired
- 1970-06-22 CH CH942570A patent/CH551451A/en not_active IP Right Cessation
- 1970-06-24 FR FR7023331A patent/FR2053018B1/fr not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2131023A (en) * | 1982-11-25 | 1984-06-13 | Ricoh Kk | Stilbene derivatives and electrophotographic photoconductors containing them |
Also Published As
| Publication number | Publication date |
|---|---|
| CH551451A (en) | 1974-07-15 |
| NL7008634A (en) | 1970-12-29 |
| FR2053018A1 (en) | 1971-04-16 |
| FR2053018B1 (en) | 1974-05-24 |
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