1,8-Diazabicyclo(5.4.0)undec-7-ene (HCID 81184)

名称と識別子

優先名称: 1,8-Diazabicyclo(5.4.0)undec-7-ene
IUPAC: 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine
現地名: 1,8-ジアザビシクロ[5.4.0]-7-ウンデセン
英語名: DBU
分子式: C9H16N2
分子量: 152.24

名称と別名

6674-22-21,8-Diazabicyclo[5.4.0]undec-7-ene1,8-Diazabicyclo(5.4.0)undec-7-enePyrimido[1,2-a]azepine, 2,3,4,6,7,8,9,10-octahydro-DTXSID2049424H1ILJ6IBUXAMICURE DBUEDABCO DBUNSC-111184DTXCID1029384ALCANPOUDRE DBU 70-3KGNSC-230466

名称をさらに表示

1,8-ジアザビシクロ[5.4.0]-7-ウンデセン2,3,4,6,7,8,9,10-オクタヒドロピリミド[1,2-a]アゼピン1,5-ジアザビシクロ[5.4.0]ウンデカ-5-エン1,8-ジアザビシクロ[5.4.0]ウンデカン-7-エン1,8-ジアザビシクロ[5.4.0]ウンデカ-7-エンDBU1,8-ジアザビシクロ〔5.4.0〕ウンデカ-7-エン1,8-ジアザビシクロ-5．4．0-ウンデカ-7-エン１，８ジアザビシクロ［５，４，０］ウンデセン７1,8‐ジアザビシクロ[5.4.0]ウンデカ‐7‐エン1.0MOL/L 1,8-ジアザビシクロ[5.4.0]ウンデカ-7-エン・テトラヒドロフラン溶液1,8-ジアザビシクロ[5.4.0]ウンデス-7-エン1,8-ジアザビシクロ[5.4.0]ウンデス-7-エン, 99%DBU2,3,4,6,7,8,9,10-OCTAHYDROPYRIMIDO[1,2-A]AZEPINEDiazabicycloundecene1,5-DIAZABICYCLO(5,4,0)UNDEC-5-ENE1,8-DIAZABICYCLO[5,4,0]-7-UNDECENE1,8-Diazabicyclo[5.4.0]undecane-7-ene1,8-DiazabicycL1,8-DIAZABICYCLO[5.4.0]UNDEC-7-ENE (DBU)

1,8-DIAZA-7-BICYCLO(5.4.0)UNDECENEPyrimido(1,2-a)azepine, 2,3,4,6,7,8,9,10-octahydro-1,8-diazabicyclo(5.4.0]undec-7-ene1,8-Diazabicyclo[5.4.0}undec-7-ene1,8-diazabicyclo{5.4.0]undec-7-eneRefChem:737341,8-DBU229-713-7

データベース識別子

CAS: 6674-22-2
PubChem CID: 81184
DTXSID: DTXSID2049424
ChEMBL: CHEMBL1489129
UNII: H1ILJ6IBUX
EC Number: 229-713-7
Nikkaji: J39.656G

物性

構造計算による物性

XLogP: 1.4
極性表面積: 15.6 Å²
水素結合供与体数: 0
水素結合受容体数: 1
回転可能結合数: 0
重原子数: 11
形式電荷: 0
複雑度: 163

実験および物理化学的性質

Chemical ClassesNitrogen Compounds -> Other Nitrogen Compounds

LogP1.38

Density1.018 @25 °C

Vapor Pressure · 2 件

0.05 [mmHg]

5.3 [mm Hg] @37.700000000000003 °C

Physical Description · 2 件

Liquid; Dry Powder

Light yellow liquid with unpleasant odor; [MSDSonline]

Ionization Efficiency · 6 件

Positive

4.24

2.7

Agilent XCT

Electrospray ionization

formic acid (5.3nM)

物理化学的性質

融点: -70 °C · -70 °C
沸点: 80 · 80-83 °C0.6 mm Hg(lit.)
比重(密度): 1.019 g/mL · 1.019 g/mL at 20 °C(lit.)
蒸気圧: 5.3 mm · 5.3 mm Hg ( 37.7 °C)
屈折率: 20 · n20/D 1.523
闪点: 230 °F · >230 °F
貯蔵温度: 30 °C · Store below +30°C.
溶解性: 溶ける
酸解離定数(Pka): 13.28 · 13.28±0.20(Predicted)
外見: 液体
色: 無色透明～薄黄色
臭い (Odor): 不快
PH: 12.8 · 12.8 (10g/l, H2O, 20℃)
爆発限界(explosive limit): 1.1 · 1.1-6.5%(V)
水溶解度: 溶ける
BRN: 508906 · 508906
安定性: 安定。強酸化剤、酸、酸塩化物、酸無水物とは相容れない。
InChI: 1S/C9H16N2/c1-2-5-9-10-6-4-8-11(9)7-3-1/h1-8H2
InChIKey: GQHTUMJGOHRCHB-UHFFFAOYSA-N
SMILES: C1CCN2CCCN=C2CC1
CAS データベース: 6674 · 6674-22-2(CAS DataBase Reference)
NISTの化学物質情報: 1 · 1,8-diazabicyclo [5.4.0]undec-7-ene(6674-22-2)
EPAの化学物質情報: 1 · Pyrimido[1,2-a]azepine, 2,3,4,6,7,8,9,10-octahydro- (6674-22-2)

化学的性質

化学的特性Colorless to yellow liquid

安全と法規制

GHS分類

GHS Classification · 5 件

This chemical does not meet GHS hazard criteria for 6.2% (48 of 776) of reports.

Danger

H290 (18.3%): May be corrosive to metals [Warning Corrosive to Metals]

P234, P260, P264, P264+P265, P270, P273, P280, P301+P316, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P330, P362+P364, P363, P390, P405, P406, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 776 reports by companies from 26 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Regulatory Information · 4 件

Chemical: Pyrimido[1,2-a]azepine, 2,3,4,6,7,8,9,10-octahydro-

Pyrimido[1,2-a]azepine, 2,3,4,6,7,8,9,10-octahydro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Pyrimido[1,2-a]azepine, 2,3,4,6,7,8,9,10-octahydro- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 19-03-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/10251

1,8-Diazabicyclo[5.4.0]undec-7-ene: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryHarmful after ingestion; Corrosive to skin; Can cause chemical pneumonitis; [MSDSonline]

Hazard Classes and CategoriesMet. Corr. 1 (18.3%)

安全と保護具

Protective Action Criteria (PAC) · 3 件

1.2 [mg/m3]

13 [mg/m3]

79 [mg/m3]

毒性情報

Adverse EffectsDermatotoxin - Skin burns.

安全データ

F: 34
wgk: 2
tsca: TSCA listed
ridadr: UN 3267 8/PG 2
毒性: LD50 orally in Rabbit: 215 - 681 mg/kg
hs_code: 29339930
risk_code: 22-34-52/53-35-40-37-19-11-67
化審法: (5)-1117
消防法: 危-4-3-III
hazard_code: C,F
safety_code: 26-36/37/39-45-61-27-16
hazard_class: 8
packing_group: II
自然発火温度: 260 °C
Hazard Classifications: Acute Tox. 3 OralAquatic Chronic 3Eye Dam. 1Met. Corr. 1Skin Corr. 1B
ストレージクラス: 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials

化学と産業

用途と製造

UsesUsed as a catalyst in the production of polyurethanes; [Ullmann]

U.S. Production2023: 400,000 - <550,000 lb

Consumer UsesNot Known or Reasonably Ascertainable

Industry UsesOther

General Manufacturing Information · 2 件

Plastics Material and Resin Manufacturing

Pyrimido[1,2-a]azepine, 2,3,4,6,7,8,9,10-octahydro-: ACTIVE

応用分野 · 6 件

解説1,8-ジアザビシクロ[5.4.0]-7-ウンデセンジアザビシクロウンデセン．略称DBU．ε-カプロラクタムとアクリロニトリルとの反応により生成する．沸点80～83 ℃(80 Pa)．1.018．1.5219．ハロゲン化アルカンに等モル量のDBUを加えると脱ハロゲン化水素が起こりアルケンが生成する．この反応の収率は，類似の1,5-ジアザビシクロ[4.3.0]-5-ノネン(DBN)を用いた場合より高く，ピリジン，キノリンなどの通常の第三級アミンでは満足な結果は得にくい．DBUは活性C-Hをもつ化合物のハロゲン化アルキルによるジアルキル化反応や，クネベナーゲル反応に用いられる．

用途有機合成(和光試薬時報Vol.63 No.2,p.26(1995))。

説明DBU is a bicyclic amidine base. It is non-nucleophilic, sterically hindered, tertiary amine base in organic chemistry. It is reported to be superior to amine catalyst in Baylis-Hillman reaction.It promotes the methylation reaction of phenols, indoles and benzimidazoles with dimethyl carbonate under mild conditions.

天然物の起源Although all commercially available DBU is produced synthetically, it may also be isolated from the sea sponge Niphates digitalis.The biosynthesis of DBU has been proposed to begin with 1,6-hexanedial and 1,3-diaminopropane.

使用DBU may be used:as catalyst for carboxylic acid esterification with dimethyl carbonatein the synthesis of duocarmycin and CC-1065 analogsas catalyst in aza-Michael addition and Knovenegal condensation reactionas base for dehalogenation of halogenated Diels-Alder adducts and the resulting activated 2,4-dienones were subjected to regio- and stereo-directed Michael additions, using Yamamoto′s reagent (CH3Cu · BF3)in a new synthesis of the ABCD ring system of CamptothecinDBU may be used as an catalyst for the dissolution and activation of cellulose by a reversible reaction of its hydroxyl groups with carbon dioxide. This dissolved cellulose system can be derivatized to form cellulose mixed esters.Used in a new synthesis of the ABCD ring system of Camptothecin.

一般的な説明We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product has been enhanced for catalytic efficiency. Click here for more information.

調製方法 · 1 件

純化方法Fractionally distil DBU under vacuum. Also purify it by chromatography on Kieselgel and eluting with CHCl3/EtOH/25% aqueous NH3 (15:5:2) and checking by IR and MS. [Oediger et al. Chem Ber 99 2012 1962, Angew Chem, Int Ed Engl 6 76 1967, Guggisberg et al. Helv Chim Acta 61 1057 1978, Beilstein 23/5 V 271.]