Triazabicyclodecene (HCID 79873)

이름 및 식별자

우선 이름: Triazabicyclodecene
IUPAC: 3,4,6,7,8,9-hexahydro-2H-pyrimido[1,2-a]pyrimidine
영어명: 1,5,7-Triazabicyclo[4.4.0]dec-5-ene
분자식: C7H13N3
분자량: 139.2

이름 및 동의어

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

이름 더 보기

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

데이터베이스 식별자

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

물성

구조 계산 물성

XLogP: -0.3
극성 표면적: 27.6 Å²
수소 결합 공여자 수: 1
수소 결합 수용자 수: 1
회전 가능 결합 수: 0
무거운 원자 수: 10
형식 전하: 0
복잡도: 153

실험 및 물리화학적 성질

Physical DescriptionLiquid

물리화학적 성질

녹는점: 125 · 125-130 °C(lit.)
끓는 점: 222.3 · 222.3±23.0 °C(Predicted)
밀도: 1.28 · 1.28±0.1 g/cm3(Predicted)
저장 조건: 2 · under inert gas (nitrogen or Argon) at 2–8 °C
용해도: 1 g/15 · 톨루엔: 가용성1 g/15 mL
물리적 상태: powder to crystal
산도 계수 (pKa): 14.47 · 14.47±0.20(Predicted)
색상: 흰색에서 거의 흰색
수용성: 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

화학적 성질

Light yellow crystalline

안전 및 규제

GHS 분류

GHS Classification · 6건

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.

유해성 정보

Regulatory Information · 3건

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%)

규제 정보

Regulatory Information · 3건

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

안전 데이터

wgk: 3
tsca: TSCA listed
ridadr: UN 1759 8/PG 2
HS 번호: 29335990
risk_code: 34
hazard_code: C
safety_code: 26-36/37/39-45-27
포장분류: III
위험 등급: 8
기존화학 물질: 2015-3-6870
F 고인화성물질: 9-21-34
Hazard Classifications: Skin Corr. 1B
스토리지 클래스: 8A - Combustible corrosive hazardous materials

화학 및 산업

용도 및 제조

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

Industry UsesCatalyst

General Manufacturing Information · 2건

Paint and Coating Manufacturing

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

응용 분야 · 3건

개요1,5,7-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].

용도1,5,7-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 설명1,5,7-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.