Triazabicyclodecene (HCID 79873)

名称と識別子

優先名称: Triazabicyclodecene
IUPAC: 3,4,6,7,8,9-hexahydro-2H-pyrimido[1,2-a]pyrimidine
現地名: 1,5,7-トリアザビシクロ[4.4.0]デカン-5-エン
英語名: 1,5,7-Triazabicyclo[4.4.0]dec-5-ene
分子式: C7H13N3
分子量: 139.2

名称と別名

TriazabicyclodeceneKAF7GN82TMTBD compoundRefChem:9333185807-14-71,5,7-Triazabicyclo[4.4.0]dec-5-ene1,3,4,6,7,8-Hexahydro-2H-pyrimido[1,2-a]pyrimidineHhpp2,3,4,6,7,8-Hexahydro-1H-pyrimido[1,2-a]pyrimidine3,4,6,7,8,9-hexahydro-2H-pyrimido[1,2-a]pyrimidine1,3,4,6,7,8-Hexahydro-2H-pyrimido(1,2-a)pyrimidineMFCD00043003

名称をさらに表示

1,5,7-トリアザビシクロ[4.4.0]デカン-5-エン1,2,3,5,6,7-ヘキサヒドロ-4H-1,4a,8-トリアザナフタレン1,2,3,6,7,8-ヘキサヒドロ-4H-ピリミド[1,2-a]ピリミジン1,3,4,6,7,8-ヘキサヒドロ-2H-ピリミド[1,2-a]ピリミジン1,2,3,4,4a,5,6,7-オクタヒドロ-1,4a,8-トリアザナフタレン1,2,3,4,6,7-ヘキサヒドロ-8H-ピリミド[1,2-a]ピリミジン3,4,6,7,8,9-ヘキサヒドロ-2H-ピリミド[1,2-a]ピリミジン1,3:2,3-ジプロパノグアニジン1,2:1,3-ジプロパノグアニジン1,2,3,4,7,8-ヘキサヒドロ-6H-ピリミド[1,2-a]ピリミジン2,3,4,6,7,8-ヘキサヒドロ-1H-ピリミド[1,2-a]ピリミジン1,5,7-トリアザビシクロ[4.4.0]デカ-5-エンSTRATOSPHERES™PL-TBD(1,3,5-トリアザビシクロデカ-5-エン)樹脂2,6,10-トリアザビシクロ[4.4.0]デカ1(10)-エン1H,2H,3H,4H,6H,7H,8H-[1,3]ジアジノ[1,2-a]ピリミジン1,5,7-トリアザビシクロ[4.4.0]デカ-6-エン4a-アザ-1,2,3,4,4a,5,6,7-オクタヒドロ1,8-ナフチリジン2,6,10-トリアザビシクロ[4.4.0]デカ-1-エン1,5,7-トリアザビシクロ[4.4.0]デカン-6-エンTBD1,5,7-TriazabicycL1,5,7-Triazabicylo[4.4.0]dec-5-ene129727

2H-Pyrimido[1,2-a]pyrimidine, 1,3,4,6,7,8-hexahydro-1,5,7-triazabicyclo(4.4.0)dec-5-ene1H,2H,3H,4H,6H,7H,8H-[1,3]diazino[1,2-a]pyrimidine2H-Pyrimido(1,2-a)pyrimidine, 1,3,4,6,7,8-hexahydro-1,5,7-triazabicyclo [4.4.0]dec-5-ene5,6,7,8-tetrahydro-1H,2H,3H,4H-pyrimidino[1,2-a]1,3-diazaperhydroineTBD; 1,3,4,6,7,8-Hexahydro-2H-pyrimido[1,2-a]pyrimidine; 1,5,7-Triazabicyclo[4.4.0]deca-5-ene; 1,5,9-Triazabicyclo[4.4.0]dec-9-ene; 2,3,4,6,7,8-Hexahydro-1H-pyrimido[1,2-a]pyrimidine;EINECS 227-367-1

データベース識別子

CAS: 5807-14-7
PubChem CID: 79873
DTXSID: DTXSID10206793
ChEBI: CHEBI:94622
UNII: KAF7GN82TM
EC Number: 227-367-1
Nikkaji: J218.068E

物性

構造計算による物性

XLogP: -0.3
極性表面積: 27.6 Å²
水素結合供与体数: 1
水素結合受容体数: 1
回転可能結合数: 0
重原子数: 10
形式電荷: 0
複雑度: 153

実験および物理化学的性質

Physical DescriptionLiquid

物理化学的性質

融点: 125 · 125-130 °C(lit.)
沸点: 222.3 · 222.3±23.0 °C(Predicted)
比重(密度): 1.28 · 1.28±0.1 g/cm3(Predicted)
貯蔵温度: 2 · under inert gas (nitrogen or Argon) at 2–8 °C
溶解性: 1 g/15mL · トルエン：可溶1g/15mL
外見: powder to crystal
酸解離定数(Pka): 14.47 · 14.47±0.20(Predicted)
色: White to Almost white
水溶解度: acetonitrile: solubleethanol: solubleorganic solvents: solublewater: soluble
BRN: 3242 · 3242
InChI: InChI=1S/C7H13N3/c1-3-8-7-9-4-2-6-10(7)5-1/h1-6H2,(H,8,9)
InChIKey: FVKFHMNJTHKMRX-UHFFFAOYSA-N
SMILES: C12=NCCCN1CCCN2
CAS データベース: 5807 · 5807-14-7(CAS DataBase Reference)

化学的性質

化学的特性Light yellow crystalline

安全と法規制

GHS分類

GHS Classification · 6 件

This chemical does not meet GHS hazard criteria for 27.7% (18 of 65) of reports.

Danger

H314 (72.3%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]

P260, P264, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P363, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 65 reports by companies from 6 notifications to the ECHA C&L Inventory.；Reported as not meeting GHS hazard criteria per 18 of 65 reports by companies.；There are 5 notifications provided by 47 of 65 reports by companies with hazard statement code(s).；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

危険有害性情報

Regulatory Information · 3 件

2H-Pyrimido[1,2-a]pyrimidine, 1,3,4,6,7,8-hexahydro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2H-Pyrimido[1,2-a]pyrimidine, 1,3,4,6,7,8-hexahydro- 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)

PMN - indicates a commenced PMN (Pre-Manufacture Notices) substance.

Status: Active Update: 05-12-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/25177

Hazard Classes and CategoriesSkin Corr. 1A (72.3%)

法規制情報

Regulatory Information · 3 件

2H-Pyrimido[1,2-a]pyrimidine, 1,3,4,6,7,8-hexahydro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2H-Pyrimido[1,2-a]pyrimidine, 1,3,4,6,7,8-hexahydro- 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)

PMN - indicates a commenced PMN (Pre-Manufacture Notices) substance.

Status: Active Update: 05-12-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/25177

安全データ

F: 9-21-34
wgk: 3
tsca: TSCA listed
ridadr: UN 1759 8/PG 2
hs_code: 29335990
risk_code: 34
hazard_code: C
safety_code: 26-36/37/39-45-27
hazard_class: 8
packing_group: III
Hazard Classifications: Skin Corr. 1B
ストレージクラス: 8A - Combustible corrosive hazardous materials

化学と産業

用途と製造

U.S. Production2023: 31,845 lb；2022: <50,000 lb；2021: <50,000 lb；2020: <50,000 lb

Industry UsesCatalyst

General Manufacturing Information · 2 件

Paint and Coating Manufacturing

2H-Pyrimido[1,2-a]pyrimidine, 1,3,4,6,7,8-hexahydro-: ACTIVE

応用分野 · 3 件

説明1,5,7-Triazabicyclo[4.4.0]dec-5-ene (TBD) is a bicyclic guanidine that has found extensive application in organic chemistry, notably as a powerful catalyst for polymer synthesis and recycling, CO2 utilization, and carboxylic acid derivative synthesis. Bearing both a nucleophilic nitrogen and an electrophilic NH group, TBD is a multifunctional reagent. It can serve as an organic superbase, an acyl transfer reagent, and a hydrogen bonding activator. It is an excellent catalyst for Michael and Michael-type reactions. The readily available organocatalyst 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) was used for the rapid synthesis of 3-hydroxyisoindolin-1-ones from 3-alkylidenephthalides[1-2].

使用1,5,7-Triazabicyclo[4.4.0]dec-5-ene may be used as organocatalyst for aminolysis of esters. It may be used as catalyst for direct addition of P(O)-H bonds (dialkyl phosphites and diphenyl phosphonite) across various activated alkenes. Polymer supported 1,5,7-triazabicyclo[4.4.0]dec-5-ene (PTBD) was used as a base and a reagent scavenger for the synthesis of aryl ethers from phenols and alkyl or aryl halides.

一般的な説明1,5,7-Triazabicyclo[4.4.0]dec-5-ene, a bicyclic guanidine base, has been found to be an excellent catalyst for Michael and Michael-type reactions. It forms 1:1 complex with lasalocid acid and crystal structure of the complex has been studied by X-ray diffraction, FT-IR spectroscopy and 1H NMR.

調製方法 · 1 件

純化方法1,5,7-Triazabicyclo[4.4.0]dec-5-ene crystallises from Et2O but readily forms white crystals of the carbonate. It is a strong base (see pK, i.e. about 100 times more basic than tetramethylguanidine). The picrate has m 220.5-222o (from EtOH). It forms the 5-nitro derivative m 14.5-160o that gives a 5-nitro nitrate salt m 100-101o (from EtOH/Et2O) and a 5-nitro picrate m 144-145o (from H2O) [McKay & Kreling Can J Chem 35 1438 1957, Schwesinger Chimia 39 369 1985, Hilpert et al. J Chem Soc, Chem Commun 1401 1983, Kamfen & Eschenmoser Helv Chim Acta 72 185 1989]. [Beilstein 26 III/IV 60.]