1,5,7-Triazabicyclo[4.4.0]dec-5-ene

한글명:1,5,7-Triazabicyclo[4.4.0]dec-5-ene

카스 번호5807-14-7

상품명:1,5,7-Triazabicyclo[4.4.0]dec-5-ene

CBNumberCB4390305

분자식C7H13N3

포뮬러 무게139.2

MOL 파일5807-14-7.mol

화학적 성질

녹는점	125-130 °C(lit.)
끓는 점	222.3±23.0 °C(Predicted)
밀도	1.28±0.1 g/cm3(Predicted)
저장 조건	under inert gas (nitrogen or Argon) at 2–8 °C
용해도	톨루엔: 가용성1 g/15 mL
산도 계수 (pKa)	14.47±0.20(Predicted)
물리적 상태	powder to crystal
색상	흰색에서 거의 흰색
수용성	acetonitrile: soluble ethanol: soluble organic solvents: soluble water: soluble
BRN	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 데이터베이스	5807-14-7(CAS DataBase Reference)

위험 및 안전 성명

위험품 표기

위험 카페고리 넘버

안전지침서

26-36/37/39-45-27

유엔번호(UN No.)

UN 1759 8/PG 2

WGK 독일

F 고인화성물질

9-21-34

위험 등급

포장분류

III

HS 번호

29335990

NFPA 704:

	0
3		0

그림문자(GHS)

1,5,7-Triazabicyclo[4.4.0]dec-5-ene 화학적 특성, 용도, 생산

개요
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 N?H 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].
화학적 성질
Light yellow crystalline
용도
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.
일반 설명
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.
Purification Methods
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.]

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