GB1009362A - Production of borazoles - Google Patents
Production of borazolesInfo
- Publication number
- GB1009362A GB1009362A GB1560661A GB1560661A GB1009362A GB 1009362 A GB1009362 A GB 1009362A GB 1560661 A GB1560661 A GB 1560661A GB 1560661 A GB1560661 A GB 1560661A GB 1009362 A GB1009362 A GB 1009362A
- Authority
- GB
- United Kingdom
- Prior art keywords
- tris
- alkyl group
- dichloroborazole
- substituted
- aryl
- 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 2,6 - dimethylphenyl Chemical group 0.000 abstract 6
- 239000007983 Tris buffer Substances 0.000 abstract 6
- 125000000217 alkyl group Chemical group 0.000 abstract 6
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 abstract 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- 150000001412 amines Chemical class 0.000 abstract 3
- 125000003118 aryl group Chemical group 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 2
- BGECDVWSWDRFSP-UHFFFAOYSA-N borazine Chemical compound B1NBNBN1 BGECDVWSWDRFSP-UHFFFAOYSA-N 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- 239000000460 chlorine Substances 0.000 abstract 2
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 239000002184 metal Substances 0.000 abstract 2
- LASWLVQCRRCCRB-UHFFFAOYSA-N (2,6-dimethylanilino)boron Chemical compound [B]NC1=C(C)C=CC=C1C LASWLVQCRRCCRB-UHFFFAOYSA-N 0.000 abstract 1
- KXIXHISTUVHOCY-UHFFFAOYSA-N 1-propan-2-ylpiperidine Chemical compound CC(C)N1CCCCC1 KXIXHISTUVHOCY-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 abstract 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 1
- NCFZNDPZLFLFOQ-UHFFFAOYSA-N NC=1C(=NBC=1)N Chemical class NC=1C(=NBC=1)N NCFZNDPZLFLFOQ-UHFFFAOYSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000003282 alkyl amino group Chemical group 0.000 abstract 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Chemical group 0.000 abstract 1
- PQZTVWVYCLIIJY-UHFFFAOYSA-N diethyl(propyl)amine Chemical compound CCCN(CC)CC PQZTVWVYCLIIJY-UHFFFAOYSA-N 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract 1
- VMOWKUTXPNPTEN-UHFFFAOYSA-N n,n-dimethylpropan-2-amine Chemical compound CC(C)N(C)C VMOWKUTXPNPTEN-UHFFFAOYSA-N 0.000 abstract 1
- GNVRJGIVDSQCOP-UHFFFAOYSA-N n-ethyl-n-methylethanamine Chemical compound CCN(C)CC GNVRJGIVDSQCOP-UHFFFAOYSA-N 0.000 abstract 1
- XWCCTMBMQUCLSI-UHFFFAOYSA-N n-ethyl-n-propylpropan-1-amine Chemical compound CCCN(CC)CCC XWCCTMBMQUCLSI-UHFFFAOYSA-N 0.000 abstract 1
- UVBMZKBIZUWTLV-UHFFFAOYSA-N n-methyl-n-propylpropan-1-amine Chemical compound CCCN(C)CCC UVBMZKBIZUWTLV-UHFFFAOYSA-N 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000003107 substituted aryl group Chemical group 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/022—Boron compounds without C-boron linkages
-
- 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/025—Boronic and borinic acid compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
Abstract
The invention comprises borazoles of the formula <FORM:1009362/C2/1> wherein R is a phenyl group substituted at least with a halogen atom or an alkyl group in each of the 2 and 6 positions, or a naphthyl group substituted at least with a halogen atom or an alkyl group in the 2 position; X is a chlorine or bromine atom or a hydroxyl, alkoxy, amino or alkylamino group, and Y is a hydrogen atom or an aryl, or substituted aryl group. b ,b -dihaloborazoles in which X is chlorine or bromine and Y is hydrogen may be made by reacting BX3 with an aminobenzene substituted at least with a halogen or alkyl group in each of the 2 and 6 positions, or with a naphthyl-1-amine substituted at least with a halogen or an alkyl group in the 2 position; or with a salt of said amine, in an inert solvent, and treating the product with triethylamine, di-n-propyl ethylamine, diethylmethylamine, diethyl-n-propylamine, di - n - propylmethylamine, isopropyldimethylamine, or a compound of the formula R1CH(R11)-N(R2)R3, where R2 and R3 are methylene groups forming part of the six-membered heterocyclic ring and R1 is hydrogen or an alkyl group, and R11 is an alkyl group, e.g. N-ethyl piperidine and N-iso-propyl piperidine. The b ,b -dihydroxyborazole may be made by hydrolyzing the b ,b -dihalo compound. The dihaloborazole may be reacted with an alcohol or amine to form b ,b -dialkoxy or diaminoborazoles. The dihydroxy- or dialkylaminoborazoles may be reacted with a metal aryl to produce b ,b -dihydroxy- or -dialkylamino-b -aryl borazoles. A b ,b ,b -triarylborazole may be made by reacting the dihaloborazole with a metal aryl. N,N,N - tris - (2,6 - dimethylphenyl) - b ,b - dihaloborazole may be made from 2,6-dimethylphenylaminoboron dihalide with one of the above amines. Examples describe the preparation of N,N,N-tris-(2,6-dimethylphenyl)-b ,b -dichloroborazole, and the corresponding N,N,N-trisubstituted - b ,b - dihydroxyborazole, b ,b -bis - (dimethylamino) borazole, b ,b - bis - (dimethylamino) b -phenyl borazole, b ,b ,b -triphenyl borazole and b ,b ,b -tris-(p-bromophenyl) borazole; N,N,N - tris - (2,6 - dichlorophenyl)-b ,b - dihydroxyborazole, N,N,N - tris - (2,6 - dibromophenyl) - b ,b - dichloroborazole; N,N,N-tris - (2 - methyl - 6 - chlorophenyl) - b ,b - dichloroborazole; N,N,N - tris - (2,4,6 - trimethylphenyl) - b ,b - dichloroborazole; and N,N,N-tris - (2 - methylnaphthyl - 1 - ) - b ,b - dichloroborazole.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1560661A GB1009362A (en) | 1961-04-29 | 1961-04-29 | Production of borazoles |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1560661A GB1009362A (en) | 1961-04-29 | 1961-04-29 | Production of borazoles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1009362A true GB1009362A (en) | 1965-11-10 |
Family
ID=10062165
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1560661A Expired GB1009362A (en) | 1961-04-29 | 1961-04-29 | Production of borazoles |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1009362A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2014510732A (en) * | 2011-03-18 | 2014-05-01 | ファキュルテ ユニヴェルシテール ノートル−ダム ド ラ ペ | Borazine derivatives |
-
1961
- 1961-04-29 GB GB1560661A patent/GB1009362A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2014510732A (en) * | 2011-03-18 | 2014-05-01 | ファキュルテ ユニヴェルシテール ノートル−ダム ド ラ ペ | Borazine derivatives |
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