JPH01143878A - Production of silicon azide - Google Patents
Production of silicon azideInfo
- Publication number
- JPH01143878A JPH01143878A JP62304739A JP30473987A JPH01143878A JP H01143878 A JPH01143878 A JP H01143878A JP 62304739 A JP62304739 A JP 62304739A JP 30473987 A JP30473987 A JP 30473987A JP H01143878 A JPH01143878 A JP H01143878A
- Authority
- JP
- Japan
- Prior art keywords
- azide
- compound
- alkali metal
- formula
- macroporous polymer
- 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.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 13
- SZJFGTWFLXTOHF-UHFFFAOYSA-N silicon tetraazide Chemical compound [N-]=[N+]=N[Si](N=[N+]=[N-])(N=[N+]=[N-])N=[N+]=[N-] SZJFGTWFLXTOHF-UHFFFAOYSA-N 0.000 title description 4
- -1 silyl halide Chemical class 0.000 claims abstract description 35
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 13
- 229920000642 polymer Polymers 0.000 claims abstract description 11
- 125000003118 aryl group Chemical group 0.000 claims abstract description 7
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 125000005843 halogen group Chemical group 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 239000002904 solvent Substances 0.000 abstract description 12
- 238000006243 chemical reaction Methods 0.000 abstract description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract description 9
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical group [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 abstract description 8
- 150000001875 compounds Chemical class 0.000 abstract description 8
- 229920001429 chelating resin Polymers 0.000 abstract description 5
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 239000003795 chemical substances by application Substances 0.000 abstract description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 abstract description 2
- GUWHRJQTTVADPB-UHFFFAOYSA-N lithium azide Chemical compound [Li+].[N-]=[N+]=[N-] GUWHRJQTTVADPB-UHFFFAOYSA-N 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 239000003513 alkali Substances 0.000 abstract 1
- 150000001540 azides Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 238000000034 method Methods 0.000 description 6
- 239000007787 solid Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- OWFCERFJVIOBHN-UHFFFAOYSA-N [N-]=[N+]=N[SiH](c1ccccc1)c1ccccc1 Chemical compound [N-]=[N+]=N[SiH](c1ccccc1)c1ccccc1 OWFCERFJVIOBHN-UHFFFAOYSA-N 0.000 description 2
- QTBUYFOMOYNJIN-UHFFFAOYSA-N azido(benzhydryl)silane Chemical compound C=1C=CC=CC=1C([SiH2]N=[N+]=[N-])C1=CC=CC=C1 QTBUYFOMOYNJIN-UHFFFAOYSA-N 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- YCITZMJNBYYMJO-UHFFFAOYSA-N chloro(diphenyl)silicon Chemical compound C=1C=CC=CC=1[Si](Cl)C1=CC=CC=C1 YCITZMJNBYYMJO-UHFFFAOYSA-N 0.000 description 1
- OJZNZOXALZKPEA-UHFFFAOYSA-N chloro-methyl-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](Cl)(C)C1=CC=CC=C1 OJZNZOXALZKPEA-UHFFFAOYSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Abstract
Description
【発明の詳細な説明】
産業上の利用分厨
本発明は、ケイ素アジド化合物の製造方法に関する。更
に詳しくは本発明は、−最大
％式％（１）
〔式中Ｒは水素原子、アルキル基、アルケニル基又はア
リール基を示す。ｎは１〜３の整数を示す。〕
で表わされるケイ素アジド化合物の製造方法に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing silicon azide compounds. More specifically, the present invention provides -maximum % formula % (1) [wherein R represents a hydrogen atom, an alkyl group, an alkenyl group, or an aryl group]. n represents an integer of 1 to 3. ] It is related with the manufacturing method of the silicon azide compound represented by these.
従来の技術及びその問題点
上記一般式（１）で表わされるケイ素アジド化合物は、
ヘテロ環化合物の合成やアジ化剤として有用な化合物で
ある。Prior art and its problems The silicon azide compound represented by the above general formula (1) is:
It is a useful compound for the synthesis of heterocyclic compounds and as an azination agent.
従来、ケイ素アジド化合物は、−最大
％式％（２）
〔式中Ｒ及びｎは前記に同じ。Ｘはハロゲン原子を示す
。〕で表わされるシリルハロゲン化物に、アルカリ金属
アジド化合物を反応させて製造されてきたが、この方法
では反応完結にまで２４〜４８時間という長時間を必要
とし、またケイ素アシト化合物の収率も満足できるもの
ではなく、工業的製法としては難点を有している。上記
反応の反応溶媒としてヘキサメチルリン酸トリアミドや
ジメチルホルムアミドを用いて該反応に要する時間を短
縮させる試みもなされている（Ｓ、Ｓ。Conventionally, silicon azide compounds have the formula: -maximum %% (2) [wherein R and n are the same as above. X represents a halogen atom. ] has been produced by reacting an alkali metal azide compound with a silyl halide, but this method requires a long time of 24 to 48 hours to complete the reaction, and the yield of the silicon acyto compound is also not satisfactory. This is not possible, and there are some difficulties as an industrial manufacturing method. Attempts have also been made to shorten the time required for the above reaction by using hexamethylphosphoric triamide or dimethylformamide as a reaction solvent (S, S).
Ｗａｓｈｂｕｒｎｅ、ｅｔ ａｌ、、 Ｊ、Ｏｒｇａｎ
ｏｍｅｔａｌ、Ｃｈｅｍ、、３３．１５３（１９７１）
）が、これは学術文献としての価値を有しているものの
、ケイ素アジド化合物の工業的製造法としては到底利用
できないものである。即ち、前者の溶媒は発ガン性を有
しており環境衛生の点で不適当であり、また後者の溶媒
を用いれば好ましくない副反応が起り、その結果収率が
低下するを避は得ないのである。更に一般式（２）のシ
リルハロゲン化物にアルカリ金属アジド化合物を反応さ
せる従来の方法では、上記一般式（１）においてＲが水
素原子又はアリール基である化合物を合成することは不
可能であった。Washburne, et al., J. Organ
ometal, Chem, 33.153 (1971)
), although it has value as an academic document, it cannot be used as an industrial method for producing silicon azide compounds. That is, the former solvent is carcinogenic and unsuitable in terms of environmental hygiene, and the use of the latter solvent inevitably causes undesirable side reactions, resulting in a decrease in yield. It is. Furthermore, by the conventional method of reacting the silyl halide of general formula (2) with an alkali metal azide compound, it was impossible to synthesize a compound in which R is a hydrogen atom or an aryl group in the above general formula (1). .
本発明の目的は、反応溶媒として安全性が高い慣用の溶
媒を用い、一般式（１）のケイ素アジド化合物を緩和な
温度条件下に且つ短時間で収率よく製造し得る方法を提
供することにある。An object of the present invention is to provide a method for producing a silicon azide compound of general formula (1) in a short time and with good yield under mild temperature conditions using a highly safe and conventional solvent as a reaction solvent. It is in.
本発明の他の一つの目的は、上記一般式（１）において
Ｒが水素原子又はアリール基である化合物を、対応する
一般式（２）のシリルハロゲン化物から製造する方法を
提供することにある。Another object of the present invention is to provide a method for producing a compound in which R is a hydrogen atom or an aryl group in the general formula (1) from the corresponding silyl halide of the general formula (2). .
本発明の方法は、一般式（２）で表わされるシリルハロ
ゲン化物に、マクロポーラスポリマーに担持させたアル
カリ金属アジド化合物を反応させて一般式（１）で表わ
されるケイ素アジド化合物を得ることを特徴とするケイ
素アジド化合物の製造方法である。The method of the present invention is characterized in that a silyl halide represented by general formula (2) is reacted with an alkali metal azide compound supported on a macroporous polymer to obtain a silicon azide compound represented by general formula (1). This is a method for producing a silicon azide compound.
上記一般式（１）及び（２）において、Ｒで示されるア
ルキル基にはメチル基、エチル基、ブチル基等が、アル
ケニル基にはビニル基等が、アリール基にはフェニル基
等がそれぞれ包含される。In the above general formulas (1) and (2), the alkyl group represented by R includes a methyl group, ethyl group, butyl group, etc., the alkenyl group includes a vinyl group, etc., and the aryl group includes a phenyl group, etc. be done.
またＸで示されるハロゲン原子には塩素原子、臭素原子
、沃素原子等が包含される。Further, the halogen atom represented by X includes a chlorine atom, a bromine atom, an iodine atom, and the like.
本発明では、マクロポーラスポリマーに担持させたアル
カリ金属アジド化合物を使用することを必須とする。In the present invention, it is essential to use an alkali metal azide compound supported on a macroporous polymer.
マクロポーラスポリマーとしては、従来公知のものを広
く使用でき、例えばアンバーライトＸＡＤ−２、アンバ
ーライトＸＡＤ−４［いずれもローム アンド ハース
社製〕、ダイヤイオンＨＰシリーズ〔三菱化成社製〕等
を挙げることができる。また、アルカリ金属アジド化合
物としては、例えばナトリウムアジド、リチウムアジド
等を挙げることができる。アルカリ金属アジド化合物の
担持量としては、特に制限がなく広い範囲内で適宜選択
が可能であるが、マクロポーラスポリマー１００ｇ当り
通常０．１〜１．０モル程度、好ましくは０．２〜０．
５モル程度とするのがよい。As the macroporous polymer, a wide variety of conventionally known ones can be used, such as Amberlite XAD-2, Amberlite XAD-4 [both manufactured by Rohm and Haas], and Diaion HP series [manufactured by Mitsubishi Kasei Corporation]. be able to. Examples of the alkali metal azide compounds include sodium azide and lithium azide. The amount of the alkali metal azide compound supported is not particularly limited and can be appropriately selected within a wide range, but it is usually about 0.1 to 1.0 mol, preferably 0.2 to 0.0 mol per 100 g of macroporous polymer.
The amount is preferably about 5 moles.
アルカリ金属アジド化合物が担持されたマクロポーラス
ポリマーは、容易に製造され得る。Macroporous polymers supported with alkali metal azide compounds can be easily produced.
アルカリ金属アジド化合物が担持されたマクロポーラス
ポリマーの使用量としては、特に制限がなく広い範囲内
で適宜選択し得るが、通常原料である一般式（２）のシ
リルハロゲン化物中のハロゲン原子１モル当り、アルカ
リ金属アジド化合物が１〜４モル程度、好ましくは１〜
２モル程度となるような割合で上記ポリマーを使用する
のがよい。The amount of the macroporous polymer on which the alkali metal azide compound is supported is not particularly limited and can be appropriately selected within a wide range. 1 to 4 moles of the alkali metal azide compound, preferably 1 to 4 moles per
The above polymers are preferably used in a proportion of about 2 moles.
本発明の反応は、通常溶媒中で行なわれる。使用される
溶媒としては、例えばアセトニトリル等の極性非プロト
ン性溶媒、ベンゼン、トルエン、キシレン等の芳香族炭
化水素類、ヘキサン等の脂肪族炭化水素類、デカリン等
の脂環式炭化水素類、ジクロロメタン等のハロゲン化炭
化水素類、テトラヒドロフラン等のエーテル類等を例示
できる。The reaction of the present invention is usually carried out in a solvent. Examples of solvents used include polar aprotic solvents such as acetonitrile, aromatic hydrocarbons such as benzene, toluene, and xylene, aliphatic hydrocarbons such as hexane, alicyclic hydrocarbons such as decalin, and dichloromethane. Examples include halogenated hydrocarbons such as, ethers such as tetrahydrofuran, and the like.
これらの中でもアセトニトリルが特に好適である。Among these, acetonitrile is particularly preferred.
本発明の反応は、通常室温〜６０℃程度の低温で好適に
進行し、一般に０．５〜６時間程度の短時間で該反応は
完結する。The reaction of the present invention normally proceeds suitably at a low temperature of about room temperature to 60°C, and is generally completed in a short time of about 0.5 to 6 hours.
上記反応終了後、固体骨を濾過し、ジクロロメタン等の
溶媒で固体を洗浄後、該溶媒を留去し蒸留することによ
り目的化合物を単離、精製することができる。After the above reaction is completed, the solid bone is filtered, the solid is washed with a solvent such as dichloromethane, and the target compound can be isolated and purified by distilling off the solvent.
発明の効果
本発明の方法では、温和な反応温度下で、しかも短時間
で目的とする一般式（１）のケイ素アジド化合物を収率
よく製造し得る。また本発明の方法で使用される溶媒は
、いずれも入手容易で安全性の高いものである。更に本
発明の方法では、上記一般式（１）においてＲが水素原
子又はアリール基である化合物を、対応する一般式（２
）のシリルハロゲン化物から容易に製造することができ
る。従って、本発明の方法は、一般式（１）のケイ素ア
ジド化合物の工業的製造法として極めて好適なものであ
る。Effects of the Invention According to the method of the present invention, the desired silicon azide compound of general formula (1) can be produced in good yield at a mild reaction temperature and in a short time. Further, all the solvents used in the method of the present invention are easily available and highly safe. Furthermore, in the method of the present invention, a compound in which R in the above general formula (1) is a hydrogen atom or an aryl group is converted into a compound of the corresponding general formula (2).
) can be easily produced from the silyl halide of Therefore, the method of the present invention is extremely suitable as an industrial method for producing the silicon azide compound of general formula (1).
実 施 例 以下に実施例を掲げて本発明をより一層明らかにする。Example Examples are given below to further clarify the present invention.
実施例１
アンバーライトＸＡＤ−４（８，６ｇ）に担持させたナ
トリウムアジド（３０ミリモル）、ジフェニルメチルク
ロロシラン（１５ミリモル）及びジクロロメタン（４０
１１１１２）の混合物を４０℃で５時間攪拌した。この
反応液をガスクロマトグラフィーで定量した結果、ジフ
ェニルメチルシリルアジドの生成率は９８％以上であっ
た。固形分を濾過後、固形分をジクロロメタン（６０ｍ
１２）で洗浄した。溶媒を留去後、減圧蒸留によりジフ
ェニルメチルシリルアジド３．１８ｇ（収率８９％）を
得た。沸点：９６〜９８℃／ ０ 、 ２ ｍｍＨｇ実
施例２
アンバーライトＸＡＤ−４（８，６ｇ）に担持させたナ
トリウムアジド（３０ミリモル）、ジフェニルクロロシ
ラン（３，２８ｇ、１５ミリモル）及びジクロロメタン
（４０１１１Ｑ）の混合物を４０℃で５時間攪拌した。Example 1 Sodium azide (30 mmol), diphenylmethylchlorosilane (15 mmol) and dichloromethane (40 mmol) supported on Amberlite XAD-4 (8.6 g)
11112) was stirred at 40°C for 5 hours. As a result of quantifying this reaction solution by gas chromatography, the production rate of diphenylmethylsilyl azide was 98% or more. After filtering the solid content, the solid content was dissolved in dichloromethane (60 m
12). After distilling off the solvent, 3.18 g (yield: 89%) of diphenylmethylsilyl azide was obtained by distillation under reduced pressure. Boiling point: 96-98 °C / 0,2 mmHg Example 2 Sodium azide (30 mmol), diphenylchlorosilane (3,28 g, 15 mmol) and dichloromethane (40111Q) supported on Amberlite XAD-4 (8,6 g) The mixture was stirred at 40°C for 5 hours.
この反応液をガスクロマトグラフィーで定量した結果、
ジフェニルシリルアジドの生成率は約１００％であった
。以下実施例１と同様に処理して、ジフェニルシリルア
ジドを得た。As a result of quantifying this reaction solution by gas chromatography,
The production rate of diphenylsilyl azide was about 100%. Thereafter, the same treatment as in Example 1 was carried out to obtain diphenylsilyl azide.
下記第１表に示すシリルハロゲン化物及び溶媒を使用し
、所定温度下に所定時間反応させる以外は、上記実施例
１と同様にして、対応するケイ素アジド化合物を得た。A corresponding silicon azide compound was obtained in the same manner as in Example 1 above, except that the silyl halide and solvent shown in Table 1 below were used and the reaction was carried out at a predetermined temperature for a predetermined time.
ケイ素アジド化合物の生成率を調べたところ、いずれの
場合も９８％以上であった。When the production rate of the silicon azide compound was examined, it was 98% or more in all cases.
Claims (1)
リール基を示す。ｎは１〜３の整数を示す。Ｘはハロゲ
ン原子を示す。〕 で表わされるシリルハロゲン化物に、マクロポーラスポ
リマーに担持させたアルカリ金属アジド化合物を反応さ
せて一般式 Ｒ＿４＿−＿ｎＳｉ（Ｎ＿３）＿ｎ 〔式中Ｒ及びｎは前記に同じ。〕 で表わされるケイ素アジド化合物を得ることを特徴とす
るケイ素アジド化合物の製造方法。(1) General formula R_4_-_nSi(X)_n [In the formula, R represents a hydrogen atom, an alkyl group, an alkenyl group, or an aryl group. n represents an integer of 1 to 3. X represents a halogen atom. ] The silyl halide represented by the formula is reacted with an alkali metal azide compound supported on a macroporous polymer to form the general formula R_4_-_nSi(N_3)_n [wherein R and n are the same as above. ] A method for producing a silicon azide compound, which comprises obtaining a silicon azide compound represented by:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62304739A JP2654516B2 (en) | 1987-12-01 | 1987-12-01 | Method for producing silicon azide compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62304739A JP2654516B2 (en) | 1987-12-01 | 1987-12-01 | Method for producing silicon azide compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01143878A true JPH01143878A (en) | 1989-06-06 |
| JP2654516B2 JP2654516B2 (en) | 1997-09-17 |
Family
ID=17936631
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62304739A Expired - Lifetime JP2654516B2 (en) | 1987-12-01 | 1987-12-01 | Method for producing silicon azide compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2654516B2 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003102002A1 (en) * | 2002-05-31 | 2003-12-11 | Humboldt-Universität Zu Berlin | Silicon polyazides and a method for their production |
| WO2008144937A1 (en) * | 2007-05-30 | 2008-12-04 | Mcmaster University | Automated solid phase analytical derivatization |
| US7781603B2 (en) | 2004-09-30 | 2010-08-24 | Toyo Boseki Kabushiki Kaisha | Method for producing trimethylsilyl azide |
| JP2013116878A (en) * | 2011-10-31 | 2013-06-13 | Toyobo Co Ltd | Method for recovering solvent in production of trimethylsilyl azide |
-
1987
- 1987-12-01 JP JP62304739A patent/JP2654516B2/en not_active Expired - Lifetime
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003102002A1 (en) * | 2002-05-31 | 2003-12-11 | Humboldt-Universität Zu Berlin | Silicon polyazides and a method for their production |
| US7781603B2 (en) | 2004-09-30 | 2010-08-24 | Toyo Boseki Kabushiki Kaisha | Method for producing trimethylsilyl azide |
| WO2008144937A1 (en) * | 2007-05-30 | 2008-12-04 | Mcmaster University | Automated solid phase analytical derivatization |
| JP2013116878A (en) * | 2011-10-31 | 2013-06-13 | Toyobo Co Ltd | Method for recovering solvent in production of trimethylsilyl azide |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2654516B2 (en) | 1997-09-17 |
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