1,8-디아자비사이클로[5.4.0]운덴센-7

한글명:1,8-디아자비사이클로[5.4.0]운덴센-7

카스 번호6674-22-2

상품명:DBU

CBNumberCB6368038

분자식C9H16N2

포뮬러 무게152.24

MOL 파일6674-22-2.mol

동의어(한글)

1,8-다이아자바이사이클로(5.4.0)언덱-7-엔

1,8-디아자비사이클로[5.4.0]운데크-7-엔

1,8-디아자비사이클로[5.4.0]운덴센-7

화학적 성질

녹는점	-70 °C
끓는 점	80-83 °C0.6 mm Hg(lit.)
밀도	1.019 g/mL at 20 °C(lit.)
증기압	5.3 mm Hg ( 37.7 °C)
굴절률	n20/D 1.523
인화점	>230 °F
저장 조건	Store below +30°C.
용해도	쉽게 용해됨
물리적 상태	액체
산도 계수 (pKa)	13.28±0.20(Predicted)
색상	무색투명~연황색
수소이온지수(pH)	12.8 (10g/l, H2O, 20℃)
냄새	불쾌한 냄새
pH 범위	12.8 at 10 g/l at 20 °C
폭발한계	1.1-6.5%(V)
수용성	녹는
감도	Air Sensitive
BRN	508906
안정성	안정적인. 강한 산화제, 산, 산 염화물, 산 무수물과 호환되지 않습니다.
InChIKey	GQHTUMJGOHRCHB-UHFFFAOYSA-N
CAS 데이터베이스	6674-22-2(CAS DataBase Reference)
NIST	1,8-diazabicyclo [5.4.0]undec-7-ene(6674-22-2)
EPA	Pyrimido[1,2-a]azepine, 2,3,4,6,7,8,9,10-octahydro- (6674-22-2)

위험 및 안전 성명

위험품 표기

C,F

위험 카페고리 넘버

22-34-52/53-35-40-37-19-11-67

안전지침서

26-36/37/39-45-61-27-16

유엔번호(UN No.)

UN 3267 8/PG 2

WGK 독일

F 고인화성물질

자연 발화 온도

260 °C

TSCA

Yes

위험 등급

포장분류

HS 번호

29339930

독성

LD50 orally in Rabbit: 215 - 681 mg/kg

NFPA 704:

	1
3		0

그림문자(GHS)

1,8-디아자비사이클로[5.4.0]운덴센-7 MSDS

1,8-디아자비사이클로[5.4.0]운덴센-7 화학적 특성, 용도, 생산

개요
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.
화학적 성질
Colorless to yellow liquid
출처
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.
용도
DBU may be used:
2. as catalyst for carboxylic acid esterification with dimethyl carbonate
4. in the synthesis of duocarmycin and CC-1065 analogs
6. as catalyst in aza-Michael addition and Knovenegal condensation reaction
8. as 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)
10. in a new synthesis of the ABCD ring system of Camptothecin
12. DBU 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.
14. Used in a new synthesis of the ABCD ring system of Camptothecin.
일반 설명
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Synthesis
The synthesis of DBU is as follows:As a base, sodium hydroxide was used at a concentration of 25% by weight and 2.3 times molar equivalent. A stirrer was placed in a 100 mL screw tube, and 11.5 g (50 mmol) of DBU hydrochloride, 8.5 g of toluene and 18.5 g (116 mmol) of 25% sodium hydroxide aqueous solution were charged at room temperature. It was placed on a magnetic stirrer and mixed for 1 hour with stirring. The mixture was separated with a 100 mL separatory funnel to obtain 18.8 g of the upper layer containing DBU and 18.4 g of the lower layer of the aqueous layer. The upper layer portion was analyzed by gas chromatography and contained 31.9% by weight of DBU, and the yield was 6.0 g (39.4 mmol) in a yield of 78.8%.
Purification Methods
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.]

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